DE1570871A1 - Verfahren zur Herstellung stickstoffhaltiger Massen,welche als Zusaetze in Kohlenwasserstoffoelen brauchbar sind - Google Patents
Verfahren zur Herstellung stickstoffhaltiger Massen,welche als Zusaetze in Kohlenwasserstoffoelen brauchbar sindInfo
- Publication number
- DE1570871A1 DE1570871A1 DE1965L0050105 DEL0050105A DE1570871A1 DE 1570871 A1 DE1570871 A1 DE 1570871A1 DE 1965L0050105 DE1965L0050105 DE 1965L0050105 DE L0050105 A DEL0050105 A DE L0050105A DE 1570871 A1 DE1570871 A1 DE 1570871A1
- Authority
- DE
- Germany
- Prior art keywords
- equivalents
- substituted
- hydrocarbon
- product
- equivalent
- 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
Links
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
- C07D207/408—Radicals containing only hydrogen and carbon atoms attached to ring carbon atoms
- C07D207/412—Acyclic radicals containing more than six carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/54—Preparation of carboxylic acid anhydrides
- C07C51/567—Preparation of carboxylic acid anhydrides by reactions not involving carboxylic acid anhydride groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07G—COMPOUNDS OF UNKNOWN CONSTITUTION
- C07G99/00—Subject matter not provided for in other groups of this subclass
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/18—Introducing halogen atoms or halogen-containing groups
- C08F8/20—Halogenation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
-
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- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
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Description
PATJi-! !ANWALT
Münrten-Pasing, AQiUs-Bs.-nnuer-SbaBe 262
THE LUBHIZOL CO1IPOIiATION, Box 3057, Euclid Station,
Cleveland 17, Ohio, USA
Verfahren zur Herstellung stickstoffhaltiger Hassen, welche als Zusätze in Kohlenwasserstoffölen
brauchbar eind
USA-Priorität vom 2. Harz 1964 aus der USA-Patentanmeldung Nr. 343 760.
Biese Erfindung bezieht sich auf substituierte Polyamine und auf Verfahren zur Herstellung derselben. Die erfindungsgemäseen substituierten Polyamine sind brauchbar als Antiversohleissmittel, Antirostmittel, Insektizide, Weichmacher,
Reinigungsmittel usw. Sie sind besonders brauchbar als Zusätze in Schniermittelaubereitungen, Brennstoffen, Kohlenwasserstoffölen und Kraftübertragungifluesigkeiten.
009809/1602
SAD
Bei der Rezeptur von ScUraiermittelBubereitungen zum Gebrauch
in Verbremiungskraftiaasohinen, bei Transmissionenf Getrieben
usw. hat man sich mit der Verschlechterung von Schmierölen» insbesondere Mineralölen sehr befasst. Die Verschlechterung
des Öls führt zur Bildung von Produkten, welche gegenüber
den Hetaliflachen, mit denen das Ul in Berührung kouat,
korrodierend wirken. Sie Verschlechterung führt auch zur Bildung von Produkten, welche sich unter Bildung schlamm-
und lackuhnlioher Ablagerungen zusammenballen. Diese. Ablagerungen verursachen ein Steckenbleiben der sioh bewegenden
Netallteile und behindern deren freie Beweglichkeit· Sie sind eine Hauptursache von Fehlleistungen und vorzeitiger Betriebe-Störung der Vorrichtung, welche das öl schmiert.
Es ist bekannt, dues Wasser eine Übliche Verunreinigung Ib
Kurbelgehäuseschmiermittel eines Motors ist. Es kann aus der Zersetzung des Schmieröle stammen, oder aus der Verbrennungekammer als durohgeblaaenea Produkt des Verbrennen·
dee Brennstoffs kommen. Die Anwesenheit Ton !fässer im Schmiermittel scheint die Ablagerung eine· mayonnaieeähnllchen
Sohlammes zu fördern. Dieser Sohlatarfcyp let starker an beanstanden, weil er an Metalloberflüchen sah anhaftet und
durch ölfilter nioht entfernt wird. Wenn der Motor unter
eolohen Bedingungen gefahren wird, dame die Temperatur de·
009809/1602
KurbelgehäusesehmierinittelB fortwährend hoch ist, so wird
aas Wasaer etwa so schnell entfernt wie <s sich ansammelt
und es bildet sich nur eine sehr kleine Menge des mayonnaise
ähnlichen Schlammes. Wenn andererseits die Temperatur des
KurbelgshäuaeschmiermittelB abwechselnd hoch und niedrig
bzw ο übereinstimmend niedrig ist, so sammelt sich Wasser an
und eine wesentliche Menge des mayonnaiseähnlichenSchlauunes
wird im Motor abgeschieden.
Hohe Arbeitstemperaturen sind kennzeichnend für einen Motor, welcher durchweg bei relativ hoher Geschwindigkeit, und
fortwährend für lange Zeitdauer lüuft. Wo jedoch ein Kraftfahrzeug
in erster Linie für Ausfahrten auf kurze Entfernungen gebraucht wird, wie sie im Stadtverkehr und für Fahrten von
zu Hause zur Arbeit kennzeichnend sind, erfolgt ein bemerkenswerter
Teil des Arbeitene, bevor der Motor seine optimal hohe Temperatur erreicht hat· Es wird so eine ideale Umgebung
für die Ansammlung von Wasser im Schmiermittel erzielt» Bei dieser Arbeitsweise ist das Problem mayonnaiseähnlichen
Schlamms besondere störend« Der Lösung des Problems ist man durch die Verwendung von Heinigungemitteln wie
Metallphenolaten und -sulfonaten im Schmiermittel nähergekommen,
von denen bekannt ist, dass sie zur Herabsetzung von Ablagerungen in Motoren wirksam sind, welche in erster
009809/1602
SAD ORIGINAL
Linie bei hohen Temperaturen arbeiten. Unglücklicherweise
Bind solche bekannten Reinigungsmittel nicht besondere wirksam eur Lösung der Probleme» welche mit dem Arbeiten
bei niedriger Temperatur in Verbindung stehen» insbesondere soloher Probleme, welche in Verbindung mit Kurbelgehäuseschmiermitteln in Noeohlnen auftreten, welohe bsi niedrigen
oder abweohoelnd hohen und niedrigen Temperaturen gefahren
werden.
Es ist demgemase ein Hauptssiel dieser Erfindung, neuartige
Kassen au schaffen. Es ist auch ein Ziel 4er Erfindung,
Maeaen su schaffen, welohe but Verwendung al· Zueätse
(Additives) in Kohlenwasserstoffölen ausgebildet sind«
Auoh ist ein Brfindungssiel die Schaffung von Massen, welohe
in Sohmiermittelaubereitungen als Reinigungemittel (Detergents)
wirksam sind· Es ist sin weiteres Erfindungesiel» neuartige
Massen au sohaffen, welohe wirksame Dispersionsmittel in
8ohniemittelsubereitungen sind, die zum Gebrauoh in Motoren
beabsichtigt sind, welohe bei niedrigen oder abweohselnd
bsi hohen und niedrigen Temperaturen gefahren werden, S* iet
ein anderes Ziel der Erfindung, verbesserte Sphmiermittelsubereitungen su sohaffen» Weiteres Erfindungesiel ist die
Schaffung verbesserter Brennstoffsubereitungen.
009809/1602 BAD
Diese und andere Ziele werden erfindungsgemäss erreicht
durch die Schaffung eines Verfahrens zur Herstellung einer stickstoffhaltigen Masse, wobei sich das Verfahren dadurch
kennzeichnet, dass man eine kohlenwasserstoffsubstituiertet
bernsteinsäurebildende Verbindung mit mindestens etwa 50 aliphatischen Kohlenstoffatomen im Kohlenwasserstoffsubstituent,
mit mindestens etwa 0,5 Äquivalenten eines Alkylenamins, und zumindest etwa 0,1 Äquivalent eines
Alkenylcyanids zur Reaktion bringt»
Zu den Alkenylamine^ von welchen die erfindungsgemässen
Produkte sich ableiten, zählen hauptsächlich diejenigen» welche meistenteils mit der Formelϊ
A-N(Alkylen-N)„H
I i n
A A
I i n
A A
übereinstimmen, in welcher η eine ganze Zahl, vorzugsweise
weniger als etwa 10 ist, A ein Wasserstoffradikal bedeutet
oder im wesentlichen ein Kohlenwasserstoff mit vorzugsweise bis zu etwa 30 Kohlenstoffatomen ist, und das Alkylenradikal
vorzugsweise ein niederes Alkylenradikal mit weniger als etwa 8 Kohlenstoffatomen bedeutet. 2Su den Alkylenaminen
zahlen hauptsächlich Methylenamine, Äthylenamine, Butylen-
009809/1602
amine, Propylenamine, Pentylenamine, Hexylenamin, Heptylen~
amine, Octylenamine, andere Polymethylenamine und auch die
cyclischen und die höheren Homologen solcher Amine wie Piperazine und arainoalkyleubstituierte Piperazine. Spezielle
Beispiele hiervon sind: Äthylendiamin, Triäthylentetramin,
Propylendiamin, Becamethylendiamin, Octamethylendiamln,
Di(Heptamethylen)triamin, Tr!propylen-tetramin, Tetraäthylenpentamin, Trimethylen-diamin, Pentaäthylen-hexamin, Di(TrI-methylen)triarain, 2-Heptyl-3-(2-aminopropyl)imidazolin,
4-Methyl-imidazolin, 1.3-bie(2-Aminoäthyl)imidazolinf
Pyrimidin, 1-(2-Aminopropyl)piperazin, 1.4-biö(2-Aminoäthyl)-piperazin und 2-Methyl-1-(2-aminobutyl)piperazin. Huhere
Homologe, wie sie durch Kondensieren von 2 oder mehreren der oben veranschaulichten Alkylenamine erhalten werden,
sind ebenfalls brauchbar.
Sie Xthylenamine sind besonders brauchbar. Sie sind eingehend beschrieben unter dem Titel "Ethylene Amines" in
"Enoyolopedia of Chemical Technology" Kirk und Othmer,
Band 5, Seiten 898 bis 905, Intersoienoe Publishers,
Hew York (1950). Solche Verbindungen werden an sweokaäesigsten
durch Umsetzung eines Alkylenohloride mit Ammoniak bereitet.
Die Reaktion führt zur Bildung etwas komplexer Gemische von
009800/1602
Alkylenaminen, einschliesalich cyclischer !Condensationsprodukte
wie Piperazine?!« Diese Geraische finden beim er»
findungsgemässen Verfahren Anwendung. Andererseits können
auch ganz befriedigende Produkte durch die Verwendung reiner Alkylenamine erzielt werden. Ein besondere brauchbares
Alkylenamin hinsichtlich Wirtschaftlichkeit als auch Wirksamkeit der daraus abgeleiteten Produkts ist ein Gemisch
von Äthylenarainen, welchen durch die Umeetsung von Xthylenchlorid
und Ammoniak hergestellt* wird und eine Zusammen»
setzung aufweist, welche derjenigen des 'Tetraäthylθnpentataine
entsprichtο
Hydroxyalkylsubstituierte Alkylenamine, d.h. Alkylenamine
mit einem oder mehreren Hydroxyalkylsubetituenten an den
Stickstoffatomen, sind ebenfalle zum Gebrauch beabsichtigt«
Die hydroxyalkylsubstituierten Alkylenamine sind vorzugsweise
diejenigen, in welchen die Alkylgruppe eine niedere Alky!gruppe ist, d.h* eine solche mit weniger als etwa
6 Kohlenstoffatomen· Zu Beispielen solcher Amine zählen N-(2-Hydroxyäthyl)athylendiarain, H.N·-bis{2-Hydroxyäthyl)-ethylendiamin,
1-(2-Hydroxyäthyl)piperazin4 mit Hydroxypropyl
monosubatituiertes Diäthylentriamin, 1.4-bis(2-Hydroxypropyl)piperazin,
mit Hydroxypropyl disubstltuiertee Tetraäthylenpentamin,
N-(3-Hydroxypropyl)tetramethylendiamin und
009809/1602
BAD ORIGINAL
2-Heptadecyl-1-(2-hydroxyäthyl)imidazolin.
Höhere Homologen, wie sie durch Kondensation der oben
veranschaulichten Alkylenamine oder hydroxyalkylsubstituierten
Alkylenimine durch Aminoradikale oder durch Hydroxyradikale
erhalten werden, sind ebenfalle brauchbar. Die Kondensation durch Aminoradikale führt zu einem höteren Amin unter Bntfernung von Ammoniak und die Kondensation duröh Hydroxyrakikale führt zu Produkten, welche Ätherbindungen enthalten»
einhergehend mit der Entfernung von Wasser.
Zu den im obigen Verfahren verwendeten, durch im wesentlichen
Kohlenwasserstoff substituierten* bernateinaäurebildenden
Verbindungen zählen die Bernsteinsäuren, -anhydride, -halogenide und -ester. Ein wichtiger Gesichtspunkt der
Erfindung ist die Grosse des im wesentlichen aus Kohlenwasserstoff bestehenden Subetituenten an der bemsteinstturebildenden Verbindung. So sind ale innerhalb des Rahmens
der Erfindung liegend, nur die substituierten bernsteinsäure bild end en Verbindungen beabsichtigt, welche aindetens
etwa 50 aliphatische Kohlenetoffatome in dem im wesentlichen
einen Kohlenwasserstoff ausmachenden Subetituenten aufweisen. Diese untere Grenze gründet sioh nicht nur auf eine Betrachtung der öllöeliohkeit der substituierten Polyamine,
oosiomiel
sondern auch auf die Wirksamkeit solcher Verbindungen bei der Anwendung, welche diese Erfindung beabsichtigt.
Der im wesentlichen einen Kohlenwasserstoff ausmachende Substituent derSuccinverbindung kann polare Gruppen enthalten,
vorausgesetzt jedoch, dass die polaren Gruppen nicht in Mengen anwesend sind, welche genügend gross sind, um den
Kohlenwasserstoffcharakter des Substituenten bemerkenswert zu verändernc Beispiele der polaren Gruppen sind Chlor,
Brom, Keto, Äther, Aldehyd, Nitro usw. Die obere Grenze hinsichtlich des Anteile solcher polarer Gruppen im
Substituenten beträgt etwa 10$, bezogen auf das Gewicht
des Kohlenwasserstoffanteile des Substituenten.
Zu Quellen des im wesentlichen einen Kohlenwasserstoff ausmachenden Substituenten zählen hauptsächlich die hochmolekularen,
im wesentlichen gesättigten Erdölfraktionea und im wesentlichen gesättigten Olefinpolymeren, insbesondere
Polymere von Monoolefinen mit 2 bis 50 Kohlenstoffatomen. Die besonders brauchbaren Polymeren sind die Polymeren von
1-Monoolefinen wie Äthylen, Propen, 1-Buten., Iaobuten,
1-Hexen, 1-Octen, 2~Methyl-1-hepten¥ 3-Cyclohexyl-1-buten
und 2~Methyl-5-propyl-1-hexen. Polymere mittlerer Olefine,
d.h. von Olefinen, in welchen die olefinische Bindung nicht in Endstellung steht, sind ebenfalle brauchbar. Sie werden
veranschaulicht durch 2-Buten, 3-Penten und 4-Octen.
Auch die Mischpolymeren der Olefine wie den oben veranschaulichten mit anderen mischpolymerieierbaren olefinischen
Substanzen wie aromatischen Olefinen, cyclischen Olefinen und Polyolefinen, sind brauchbar. Zu solchen Mischpolymeren
zählen beispielsweise diejenigen, welche hergestellt wurden durch Polymerisieren von Isobuten mit Styrol, Isobuten mit
Butadien, Propen mit Isopren, Äthylen mit Piperylen, Isobuten mit Chloropren, Isobuten mit p-Methylstyrol,
1-Hexen mit 1.3-Hexadien, 1-Octen mit 1-Hexen, 1-Hepten
mit 1-Penten, 3-Methyl-1-buten mit 1-Octen, 3.3-Dimethy1-1-penten mit 1-Hexen, Isobuten mit Styrol und Piperylen
usw.
Sie relativen Mengenanteile der Monoolefine au den anderen' Monomeren in den Mischpolymeren beeinflussen die Stabilität
und die öllöelichkeit der von solchen Mischpolymeren .abgeleiteten Endprodukte. Saher sollten aus Gründen der öllöelichkeit und Stabilität, die zur Verwendung in dieser
Erfindung vorgesehenen Mischpolymeren im wesentlichen
aliphatisch und im wesentlichen gesättigt sein, d.h. sie
BAD
sollten mindestens etwa 8C, vorzugsweise niindestena etwa
95 Gewe^S an Einheiten enthalten, welche sich von den
aliphatischen Monoolefinen ableiten und nicht mehr ale etwa
5$ an olefinischen Blmiungen, bezogen auf die Gesaratanzahl
der Kohlenstoff-an-Koh** anstoff-Kovalentbindungen. In den
meisten Fällen sollte der Prozentgehalt an olefinischen
Bindungen geringer sein als etwa 2$ der GesamtanzaliX an
Kohlenstoff-Kohlenetoff-Kovalentbindungen«
Zu spezifischen Beispielen solcher Miechpolymerer zählen
das Copolymere von (auf das Gewicht bezogen) 95$ Isobuten
mit 5# Styrol, das Terpolymere von 98$ Isobuten mit I^
Piperylen und t$ Chloropren, das !Üerpolymere von 95$ Isobuten
mit 2$ 1-Buten und 3$ 1-Hexen, das Terpolymere von 80$
Isobuten mit 20$ 1-Penten und 2O# 1-Octan, das Copolymere
von 80$ 1-Hexen und 20$ 1-Hepten, das Terpolymere von 90$
Isobuten mit 2$ Gyclohexen und 8$ Propen, und das Copolymere
von 8O?6 Äthylen und 20$ Propen«.
Eine andere Quelle des im wesentlichen Kohlenwasserstoff ausmachenden Radikals umfasst gesättigte aliphatische
Kohlenwasserstoffe wie hochraffinierte, hochmolekulare,
farblose Paraffinöle oder synthetische Alkane, wie sie durch
009809/1602
sad
Hydrierung der oben veranschaulichten hochmolekularen Olefinpolymeren oder hochmolekularen olefinischen Substanzen
gewonnen werden.
Sie Verwendung von Olefinpolymeren mit einem Molekulargewicht von etwa 750 bis 3000 ist bevorzugt. Es wurde gefunden, dass höhermolekulare Olefinpolymere mit Molekulargewichten von etwa 10 000 bis etwa 100 000 oder höher, den
Endprodukten der Erfindung auch visJcoeitätsindexverbeseernde
Eigenschaften verleihen. Die Verwendung eoloher höhermolekularen Olefinpolymeren ist oft erwUneoht.
Die in obigem Verfahren brauchbaren berneteinsäurebildenden
Verbindungen sind vorzugsweise im wesentlichen kohlenwasserstoff substituierte Bernsteineäuren und Anhydride· Diese
Suocinverbindungen sind leicht zugänglich aus der Reaktion von Maleinsäureanhydrid mit einea hochmolekularen Olefin
oder einem chlorierten Kohlenwasserstoff wie dem oben beschriebenen Olefinpolymeren. Die Reaktion besteht in dem
tolossen Erhitzen der beiden Reaktionsteilnehmer 1>ei einer
Temperatur von etwa 100 bis etwa 2000C* Das Produkt aus
einer solchen Reaktion 1st ein AUcenylberneteinskureanhydrid.
Die Alkeny!gruppe kann su einer Alkylgrupp· hydriert werden.
000109/1*02 «AD ORIGINAL
Das Anhydrid kann durch Behandlung mit Wasser oder Dampf
zu der entsprechenden Säure hydrolysiert werden» Durch Reaktion mit beispielsweise Phoaphorhalogenid, Phenolen
oder Alkoholen, können sowohl das Anhydrid als auch die Säure zu dem entsprechenden Säurehalogenid oder Ester umgewandelt
werden.
Anstelle der Olefine oder chlorierten Kohlenwasserstoffe kann man in der oben veranschaulichten Reaktion zur Herstellung
der Suooinverbindungen andere Kohlenwasserstoffe verwenden, welche einen aktivierenden polaren Substituenten
enthalten, d.ho einen Substituenten, welcher in der Lage ist, das Kohlenwasserstoffmolekül in Bezug auf die Reaktion
mit Maleinsäure oder Maleinsäureanhydrid zu aktivieren» Solche polaren Substituenten können veranschaulicht werden
durch Sulfid-, Disulfid-, Nitro-, Mercaptan-, Brom-,
Keton- oder Aldehydradikale. Zu Beispielen solcher polarsubstituierter
Kohlenwasserstoffe zählen Polypropensulfld,
Di-Polyisobuten-disulfid, nitriertes Mineralöl, Di-PoIyäthylen-sulfid,
bromiertee Polyäthylen uew. Zu einer anderen Methode» welche zur Herstellung der Berneteinaäuren
und -anhydride brauchbar 1st, gehört die Reaktion von Itaoonsäure mit einem hochmolekularen Olefin oder einem
pOlarsubstitulerten Kohlenwasserstoff bei einer Temperatur,
009809/1*02
welche gewöhnlich innerhalb dea Bereiches von etwa
bis etwa 20O0C liegt.
Die Säurehalogenide der Bernsteinsäuren können bereitet werden durch die Reaktion der Säuren oder ihrer Anhydride
mit einem Halogenierungemittel wie Phosphortribromid,
Phoephorpentaohlorid oder Thionylchlorid. Sie Seter
solcher Säuren können einfach hergestellt werden durch die Umsetzung der Säuren oder ihrer Anhydride mit eines
Alkohol oder einer phenolischen Verbindung wie Methanol,
Äthanol, Ootadeoanol, Cyclohexanol/ Phenol, Naphthol,
Octylphenol usw. Die Veresterung wird gewöhnlich gefördert
durch die Verwendung eines alkalischen Katalysator· wie Natriumhydroxyd oder Natriumalkoxyd, oder eines sauren
Katalysators wie Schwefelsäure. Sie Natur des alkoholischen oder phenolisohen Anteils de· Eeterradikale
scheint geringen Einfluss auf die Brauchbarkeit eines solchen Esters als Reaktionateilnehmer In oben beschriebene!
Verfahren zu haben.
Die la erflndungsgemässen Verfuhren brauchbaren Altonyloyanlde sind vorzugsweise dl· Vinyloyanide gemäss der
Strukturforaelt
R<
H1
ORIGINAL
009809/1602
in welcher R1 und R2 Wasserstoff- oder Kohlenwasserstoffj
iidlkalfi sind. Besonders brauchbar sind die Tinylcyanide,
in welchen die beiden R^-Eadikale je !faserstoff oder eiüv
Alky!gruppe mit bis zu etwa 12 Kohlenstoffatomen sind und
das Rg-Radikal Wasserstoff oder eine niedere Alkyigru^pte
mit bis zu etwa 6 Kohlenstoffatomen ist* Zu Beispielen solcher Vinylcyanide- zählen Vinylcyanid (d.h. Acrylnitril),
1-Methyl-vinylcyanid, 1-Butylvinyl-cyanid, ί-Hexylvinylcyanid,
i-Cyclohexylvinyl-eyanid, 1-tert.-Butylvinylcyanid
und 1-Iso.propylvinyl-eyanid. Zu anderen hler brauchbaren
Vinyleyaniden zählen 2-Methylvinyl-cyanid (d.h. Crotonnitril),
2-Dodecylvinyl-cyanid, 2.2·-Didodecylvinyl-cyanid,
2-Cyclopentylyinyl-cyanid, 2~0otyl2- methylvinyl-cyanid,
2-Deoyl-2-hexylvinyl-cyanid, und 2-tert.-Pentylvinylcyanid
·
Alkenylcyanide, in welchen die Oyanidgruppe von der olefinischen
Gruppe durch eine oder mehrere Methylenradikale getrennt ist, sind ebenfalls im erfindungsgemäsaen Verfahren
brauchbar. Beispiele hierfür sind 3-Hexenyl-cyanid,
2-Octenyl-cyanid usw. Auch sind brauchbar die arylsubstituier
ten Alkenylcyanide wie 1-Phenylvinyl-cyanid, 2-Phenylvinyl-cyanid,
1-Tolylvinyl-cyanid, oder 2-Phenethylvinylcyanid.
009809/1602
BAD
Das erfindungsgemässe Verfahren kann auegeführt werden,
indem man den Succinreaktionateilnehmer, das Alkylenamin
und das Alkenylcyanid vermischt und das Gemisch bei der gewünschten Reaktionstemperatur erhitzt. Man kann auoh
den Succinreaktioneteilnehmer zuerst mit dem Alkylenanin
und dann mit dem Alkenylcyanid umsetzen. Die bevorzugte Art der Ausführung des Verfahrens besteht darin, dass man
zuerst das Alkylenamin mit dem Alkenylcyanid unter Bildung
eines Zwischenproduktes umsetzt, und man dann das Zwischenprodukt mit dem Suocinreaktlonsteilnehmer reagieren läset.
Die Temperatur, bei welcher das erfindungsgemässe Verfahren
gewöhnlich '
ausgeführt werden kann, schwankt/von etwa 80 bis 250 C oder höher. Eine niedere Temperatur kann in einigen Fällen
angewendet werden, z.B. wo eine relativ reaktionsfähige Bernsteinsäure bzw. -anhydrid angewandt wird. Die obere
Temperaturgrenze ist der Zersetzungspunkt des Reaktionsgemisches. Das Verfahren wird vorzugsweise in Anwesenheit
eineβ Verdünnungsmittels bzw. Lösungsmittels wie Benzol,
Naphtha, Toluol, Chlorbenzol oder Dioxan ausgeführt. Mineralöl ist als Lösungsmittel besondere brauohbar.
Die bein Verfahren zu verwendenden relativen Hengen der Reaktionsteilnehmer sind derart, dass für jedes Äquivalent
des Succinreaktioneteilnehmers mindestens etwa 0,5 Äquivalent
009109/1602
**O ORigiNal
des Alkylenamins■und zumindest etwa 0,1 Äquivalente des
Alkenylcyanids vorhanden sein sollten. Vorzugsweise werden
1 bis 5 Äquivalente des Alkylenarains und 0,5 bis 4 Äquivalente des Alkenylcyanids je Äquivalent des Succinreaktions·
teilnehmers verwendet. Es können auch mehr Alkylenamin oder Alkenyloyanid angewandt werden. Sie obere Grenze der Mengen
dieser Reaktionsteilnehmer hängt in groasem Ausmass von der
Anzahl Aminogruppen in der Molekularstruktur des Alkylenamins ab. Gewöhnlich werden nicht mehr als je 2 Mol des
Alkylenamins und des Alkenyloyanids pro Äquivalent des Suoeinreaktionsteilnehmers verwendet. Bs sei bemerkt, dass
sich das Äquivalentgewicht des Sucoinreaktionsteilnehmers
auf die Anzahl der carbonsüurebildenden Radikale in einem
Molekül, das Äquivalentgewicht des Alkylenamins auf die Anzahl Aminogruppen in einem Molekül, und das Äquivalentgewicht des Alkenylcyanids auf die Anzahl der Qlefin-
BAD
-well
Windungen in einem Molekül gründet. So besitzt eine
kohlenwasserstoffsubstituierte Bernsteinsäure oder -anhydrid mit einer Succlngruppe in der molekularen
Struktur zwei Äquivalente je MoI9 ein Alkylenpentamin
5 Äquivalente je Mol, und ein Vinylcyanid weist 1 Äquivalent je Mol auf.
Die chemische Konstitution der stickstoffhaltigen Produkt·
des erfindungsgemässen Verfahrene ist nicht gans bekannt.
Bekannt ist jedoch, dass das Stickstoffatom der Aminogruppen vom Alkylenamin direkt an das Succinradikal angegliedert
i3t und sich ein acyliortes Amin alt Bindungen
1S
bildet, welche durch ein Amid, Imid, Amidin oder ein Salz
dargestellt werden. Daa Produkt weist gewöhnlich ein Gemisch
solcher Bindungen auf. Ba iat auch bekannt, dass die Reaktion
des Allcenylcyanids gewöhnlich die olefinische Gruppe umfasst,
welche in dessen molekularer Struktur anwesend ist» Es wird angenommen, dass eine solche Reaktion in der
Addition einer Arainogruppe des Alkylenamins oder des acylierten Amins an die olefinische Gruppe des Alkenylcyanids
besteht« Die Oyanidgruppe des Alkenylcyanids scheint nicht direkt in die Reaktion einbezogen zu sein, wenngleich
sie in einigen Fällen mit einer Aminogruppe des Alkylenamins oder acylierten Amins kombiniert sein kann. In jedem Falle
iat das Verfahrensprodukt, ohne Rücksicht auf die in seiner
molekularen Struktur vorhandenen relativen BindungsantoilV, <
für die Zwecke dieser Erfindung brauchbar«,
Es sei bemerkt, dass die Bildung eines acylierten Amins, welches vorwiegend eine Amid- oder eine -salzbindung.
zwischen dem Carboxylradikal des Succinreaktionsteilnehmers
»
und der Aminogruppe des Alkylenamins aufweist, 1 Äquivalent jedes der beiden Reaktionsteilnehmer umfasst, und dass die Bildung eines acylierten Amins mit vorzugsweise Imidbindungen 2 Äquivalente des Succinreaktionsteilnehmere und 1 Äquivalent des Alkylenamins umfasst. Andererseite umfasst die
und der Aminogruppe des Alkylenamins aufweist, 1 Äquivalent jedes der beiden Reaktionsteilnehmer umfasst, und dass die Bildung eines acylierten Amins mit vorzugsweise Imidbindungen 2 Äquivalente des Succinreaktionsteilnehmere und 1 Äquivalent des Alkylenamins umfasst. Andererseite umfasst die
00980S/16C? gAD original
X*
Bildung eines aoylierten Amine wie Imidazolin mit vorwiegend Amidinbindungen, 1 Äquivalent dee Succinreaktionsteilnehmers und 2 Äquivalente der Alkylenamine. Die ohemieche Konstitution des Produktes des erfindungageaäseen
Verfahrens hängt daher bis zu gewissem Auamaee von den relativen Mengenverhältnissen der im Verfahren verwendeten
Reaktionsteilnehmer ab. Auch neigt eine relativ niedrige Reaktionstemperatur wie beispielsweise unterhalb 10O0C
zur Förderung der Salzbildung, wohingegen eine relativ
hohe Reactionstemperatur wie oberhalb 1000O dazu neigt,
die Bildung von Imiden oder Amiden zu fördern. Eine noch höhere Temperatur, wie 2000C oder höher, neigt zur Förderung
der Bildung von Imidazolinen oder polymeren linearen Amidine^
Sie folgenden Beispiele veranschaulichen dae erfindungsgemässe Verfahren:
Se wird ein polyiaobuteneubstituiertes Bernsteinsäureanhydrid bereitet, indem man chlorierte« Polyisobuten
mit Maleinsäureanhydrid (20£iger molarer Übersohuea) bei
2000C umsetzt. Das Polyieobutenylradikal besitzt ein
mittleres Molekulargewicht von 850 und man findet» dass dae sich ergebende substituierte Bernsteinsäureanhydrid
*AD
001109/1602
eine Säurezahl von. 113 (entsprechend einem Äquivalentgewicht von 500) aufweist. Ein Gemisch aus 500g (1 Äquivalent) dieses substituierten Bernsteinsäureanhydrids,
189g (5 Äquivalente) Tetraäthylen-pentamin und 67g (1 Äquivalent) Crοtonsäurenitril wird bei Raumtemperatur bereitet,
mit 200Og Mineralöl vermischt, und dann für 7 Stunden bei 100 bis 2000C erhitzt. Bas Produkt ist eine öllsöung der
gewünschten stickstoffhaltigen Masse der Erfindung.
Bs wird ein cyanäthylsubQtituiertes Äthylenamin bereitet,
indem man 212g Acrylnitril mit 216g eines Äthylenamingemieohes, welches aus 75 Gew.^ Triäthylentetramin und
25 Gew.jS Diäthylentriamin besteht, bei Raumtemperatur
vermischt, das Gemisch 5 Stunden bei 110 bis 1300C erhitzt, und dann auf 125°C/3Omm arhitst« Zu einem Gemisch
aus 111Og des polyisobutensubatituierten Bernsteinsäureanhydrid β yon Beispiel 1 und 825g Mineralöl, setzt man
bei 60°0 tropfenweise 143g des obigen cyanäthyleubstituierten Äthylenaraine (mit eine« Stickstoff gehalt von
y hinzu. Dae Gemisch wird für 5 Stunden bei 150 bis
1600C erhitzt, während man es mit Stickstoff säubert.
Insgesamt werden 6cnr Wasser durch Destillation entfernt.
Der Rückstand besitzt einen Stickstoffgehalt von 1,66$.
ÖAD CiväiiÄ
Zu 330 Teilen (auf das Gewicht bezogen) (8 Äquivalente) eineβ handelsüblichen Äthylenamingemisohes mit einen
Stickstoffgehalt von 34£ und einer mittleren Zusammensetzung, welche im wesentlichen derjenigen von Tetraäthylenpentamin entspricht, setzt Man bei 40 bis 5O0C innerhalb
eines Zeitraumes von 4 Stunden 318 Teile (6 Äquivalente)
Acrylnitril hinzu. Ea tritt ein· exotherme Reaktion ein.
Ba* Gemisch wird für 2 Stunden bei 50 bis 550C, und für
2 Stunden bei der Rückflusstemperatur (110 bis 1150C)
erhitet. Dann wird es für 2 Stunden bei 125 bis 1300O
mit Stickstoff geblasen. Der Rückstand, 644 Teile, wird au 2235 Teilen Mineralöl hinzugesetzt, und die Masse wird
bei 70 bis 800C mit 2970 Teilen (5,3 Äquivalente) dee
polyiBobutenaubstituierten Bernsteinsäureanhydride von Beispiel 1 (mit einer Säuresahl von 100) vermischt, und
das Gemisch wird tür 3 Stunden bei 1500C erhitst und für
5 8tunden bei 150 bis 1550C alt Stickstoff geblasen, wobei
27 Teile Wasser abdeetillieren. Der Rückstand wird alt
•Ibm mtrlerhilfsmittel vermischt und filtriert. Da«
filtrat (5580 Teile, 96* der theoretieohen Ausbeute) iet
eine 38,5*ige OllOsung dee stickstoffhaltigen Produkt··
und bssitst einen Stickstoffgehalt von
Al
Zu 1020g (25 Äquivalente) eines handelsüblichen Äthylenamingemisches
mit einer mittleren Zusammensetzung, welche derjenigen
von Tetraäthylenpentamin entspricht, und mit einem
Stickstoffgehalt von 34,39», setzt man bei 22 bis 6O0C tropfenweise
1325g (25 Äquivalente) Acrylnitril hinzu. Es findet eine exotherme Reaktion statt. Die Reaktionsmasse wird während des
Zusatzes durch äusoere Kühlung bei 22 bis 600O gehalten und
dann wird sie für 2 Stunden bei 280G, für 3,25 Stunden bei
108 bis 1150C, und dann auf 1300C/26mm erhitzt. Der Rückstand,
2196g, ist ein Zwischenprodukt mit einem Stickstoffgehalt von 29,7$. Eine Portion (624g) des Zwischenproduktes und Mineralöl
(1456g) werden in einen Reaktionskolben gebracht und auf 1000C erhitzt. Zu diesem Gemisch setzt man in 4,25 Stunden
bei 120 bis 1350C 1456g Mineralöl und 3808g (7 Äquivalente;
entsprechend 1 Äquivalent je Äquivalent des Äthylenamins im
Zwischenprodukt) des polyisobutensubstituierten Bernsteinsäureanhydrids mit einer Säurezahl von 103, hergestellt wie in
Beispiel 1 beschrieben, hinzu. Das sich ergebende Gemisch wird in 5 Stunden auf 1500C erhitzt und für 3 Stunden bei
dieser Temperatur mit Stickstoff geblasen. Es wird mit einem
Filtrierhilfsmittel gemischt und filtriert. Das FiItrat, 6945g (95,4$ der theoretischen Ausbeute), ist eine 40$ige
öllsöung der gewünschten stickstoffhaltigen Masse der Erfindung
009809/1602 BÄD original
und besitzt einen Stickstoffgehalt von 2,2ji.
Ee wird ein Alkylenamin-Aikenylcyanid-Zwisohenprodukt erhaltenf
indem man 106Og (20 Äquivalente) Aorylnitril und 1632g {40 Äquivalente) des handelsüblichen Äthyleharain^emisohes von Beisp.4
bei 45 bis 550C miecht (wobei Kühlen von aussen erforderlich
ist» um den Temperaturbereich einzuhalten)» das»Gemisch für
1 Stunde bei 400C bewegt und es für 2 Stunden bei 110 bis 12O0C
und dann bei 120°C/18.nia erhitzt, um flüchtige Komponenten abzudestillieren. Der Rückstand ist das gewünschte Zwischenprodukt
mit einem Stickstoffgehalt von 30,8$. Bine Portion (716g) des
Zwischenproduktes wird bei 66 bis 830C tropfenweise zu einem
Gemisch aus 2853g Mineralöl und 3626g (7 Äquivalente) entsprechend 1 Äquivalent je 1,5 Äquivalente des Äthylenamins im
Zwischenprodukt) des polyisobutensubstltuierten Bernateineäureanhydrids mit einer Säurezahl von 107 und hergestellt« wie in
Beispiel 1 beschrieben, hinzugesetzt. Das sich ergebend· Gemisch wird auf 145 bis 1560C erhitzt und dann bei dieser Temperatur
3 Stunden mit Stickstoff geblasen· Man mischt es mit einem Filtrierhilfsmittel und filtriert. Sas Piltrat, 6693g» 1st
eine 40£ige öllösung des gewünschten Produktes und besitzt
einen Stickstoffgehalt von 2
001109/1102
as
Es wird, wie in Beispiel 5 beschrieben» ein Alkylenamin-Alkenylcyanid-Zwiaehenprodukt
aus einem Reaktionsgemisch von 3f1 Äquivalenten des handelsüblichen Äthylenamingemisches
von Beispiel 4 und 1 Äquivalent Acrylnitril erhalten. Ein Gemisch aus 3264g (6 Äquivalente) des polyisobutensubstituierten
Bernsteinsäureanhydrida mit einer Säurezahl von 105 und
wie in Beispiel 1 beschrieben hergestellt, 3100g Mineralöl und 691g (12 Äquivalente vom Äthylenarain) des Amin-Oyanid-Zwischenprodukte3
wird bei 110 bis 1150Q bereitet, 3 Stunden
bei 150 bis 1530C mit Stickstoff geblasen, mit einem Filtrierhilfsmittel
gemischt und filtriert. Das Filtrat, 6704g» ist eine 44,3$ige Mineralöllosung des gewünschten Produktes
und besitzt einen Stickstoffgehalt von 2,95*·
ο
Bs wird bei 120 C ein Gemisch aus 3264g (6 Äquivalente) dea polyisobuteneubetituiortoii Beinsteinsäureanhydride vom Beispiel 6, 2574g Mineralöl» und 651g (12 Äquivalente des Äthylenamina) einea Alkylenamin-Aikonyloyanid-Zwiecnenprodulrtee (gewonnen durch ümeetaung von 4,1 Äquivalente» des handele« üblichen Ätkylenamlngemieohee voa Beiepi*l .4 und 1 Äquivalent Acrylnitril) bereitet. Daß Gemisch wird dann 3 Stunde» bei 150 bin 1570C art* Stickf'-off geblasen^ ült eine® F
Bs wird bei 120 C ein Gemisch aus 3264g (6 Äquivalente) dea polyisobuteneubetituiortoii Beinsteinsäureanhydride vom Beispiel 6, 2574g Mineralöl» und 651g (12 Äquivalente des Äthylenamina) einea Alkylenamin-Aikonyloyanid-Zwiecnenprodulrtee (gewonnen durch ümeetaung von 4,1 Äquivalente» des handele« üblichen Ätkylenamlngemieohee voa Beiepi*l .4 und 1 Äquivalent Acrylnitril) bereitet. Daß Gemisch wird dann 3 Stunde» bei 150 bin 1570C art* Stickf'-off geblasen^ ült eine® F
BAD ORlG1NAL
hilfsmittel gemischt und filtriert. Dae Piltrat (6166g,
96# der theoretischen Ausbeute) ist eine 4O£ige öllöeung
des gewünschten Produktes und hat einen Stickstoffgehalt ▼on 3,1#.
Es wird bei 115 bis 12O0C ein Gemisch aus 3808g (7 Äquivalente
des polyisobutensubs-tituierten Bernsteinsäureanhydride von
Beispiel 6, 2740g Mineralöl, und 365g (5,22 Äquivalente des
Äthylenamins) eines Zwischenproduktes (gewonnen durch die Umsetzung von 2 Äquivalenten des handelsüblichen Äthylenamingeinieches
von Beispiel 4 und 1 Äquivalent Acrylnitril) bereitet. Bas Gemisch wird 3 Stunden bei 150 bis 153°C alt
Stickstoff geblasen, mit einem Filtrierhilfemit Lei geaisoht
und filtriert. Das Piltrat, 6563g, ist eine 4O£lge öllöeung
des gewünschten Produktes und besitzt einen Stickstoffgehalt ▼on 1,53*·
E» wird ein aoyliertes Aainawieohenprodukt erhalten, indea
MB 1 Äquivalent dee polyieobutensubatituierUn BerneWin-
saurtanhydrids von Beispiel 1 und 2 Äquivalente 4e« luuMlel^-
ttUleten Äthylenaeingeeieohes von Beispiel 4 bei 150 M.·
1700O uMetzt. Ein Gemisch aus 265g (5 Äquivmleat·) Aoryl-
nitril und 553Og (10 Äquivalente des Äthylenaein») *Ιώβτ
009109/1602
4O?iigen öllöeung des acylierten. Aminzwischenproduktes, wird
1 Stunde bei Rückflusstemperatur (105 bis 1450G) erhitzt.
Das Gemisch wird dann 3 Stunden bei 1450C erhitzt, auf 10O0O
abgekühlt und auf 118°0/18mra erhitzt. Es wird mit 144g Mineralöl gemischt, wobei sich eine 40#ige öllöaung des gewünschten
Produktes bildet. Sie Lösung hat einen Stickstoffgehalt von '3,35*.
Ea wird ein acyliertes Aminzwischenprodukt erhalten, indem
man bei 150 bis 170°C 1 Äquivalent des polyisobutensubstituierten Bernsteinsäureanhydrids von Beispiel 1 und 1,5
Äquivalente des handelsüblichen Äthylenamingemiachea von
Beispiel 4 umsetzt. Eine 4O#ige öllösung des Zwischenproduktes
besitzt einen Stickstoffgehalt von 2$. Bin Gemisch
aus 424g (8 Äquivalente) Acrylnitril und 5600g (8 Äquivalente des Äthylenamins) einer 4Q#igen Mineralöllösung des acylierten
Aminzwischenproduktes, wird 5 Stunden bei der Bückfluss~
temperatur (94 bis 1180O) erhitzt. Das Gemisch wird dann
auf 128°C/12mm erhitzt, wobei 238g Acrylnitril abdestillieren.
Der Rückstand wird mit 103g Mineralöl verdünnt Und bildet eine 40#ige Öl lösung des gewünschten Produktes <, Die Lösung
besitzt einen Stickstoffgehalt von 2,1
ßAD
009609/1602
it
Es wird ein acyliertes Aminzwischenprodukt erhalten, indem
man 4 Äquivalente des polyisobutensubstituierten Bernsteinsäureanhydride von Beispiel 1 und 3 Äquivalente des handelsüblichen Äthylenamingemieches von Beispiel 4 bei etwa 150
bis 1700C umsetzt. Eine 4O#ige öllösung des Zwischenproduktes hat einen Stickstoffgehalt von 1,14#. Ein Gemisch
aus 7368g (6 Äquivalente des Äthylenamins) des aoylierten Aminewiechenproduktee und 159g (3 Äquivalente) Acrylnitril
wird für 1,25 Stunden bei der Rückflueatemperatur von 1250G
bis 1450C, für 3 Stunden bei 1450C, und dann bei 125°C/18am
erhitzt, wobei 107g Acrylnitril abdestillieren. Per Rückstand wird mit 35g Mineralöl verdünnt und bildet eine 40#ige
Ollusung des gewüneohten Produktes mit einem Stickstoffgehalt von 1,34*.
Be wird eine polyisobutensubstitulerte Bernsteinsäure hergestelltt indem man das substituierte Bernsteinsäureanhydrid
von Beispiel 1 mit Dampf hydrolysiert. Bei 25 bis 600O bereitet man ein Gemisch aus 1 Äquivalent der Bernsteinsäure,
2 Äquivalenten Hexamethylendiamin, und 1 Äquivalent 1-Methylvinyloyanid (^-Methyl-acrylnitril). Das Gemisch wird auf
10O0O erhitet und tür 7 Stunden bei dieser Temperatur ge-
001109/1602
halten» Es wird dann mit einem gleichen Volumen Mineralöl
vermischt und bei 1QG°ö/1mm erhitzt, um flüchtige Komponenten absudestillieren» Der Rückstand wird filtrierte
Das Filtrat ist eine Mineralöllösung des gewünschten
Produktes.
Es wird ein Seaisoh su?<
2 Äquivalenten A^yiaudiaain,
0,2 Äquivalent 2.2-DinsetLjiTinyl-ovanid, und 1 Äquivalent
eines mit Polypropen vom Molekulargewicht 3000 substituierten
Bernsteinsäureanhydride mit ainer Säurezahl von 90 bereitet»
ο indem man die Reaktioneteilnehmer bei 25 bis 80 C sorgfältig
mischt« Das Gemieoh wted dann bei 1500O erhitzt* mit
gleichen Volumen Min$r&13l vermischt and hai diesai1
peratur 5 Stunden mit Stickstoff geblasen* Ber Rüe
wird filtriert»
Bs wird ein Alkylenamin«Alk8nylsya,nid-2';ndsohi3iip3rc»iIi&t saielt,
indem man 1 Äquivalent Irinethylondiaiaia "yji4 0s1
Äquivalent Acpylnitril bei 25 bia !>0σδ niecht una ctäe
Gemisch 2 Stunden bsi TO0G erhitat» 3>us 2
wird dann ait 1 Äquivalent emüb nit PoIv?
Molekulargewicht 900 c ; ;Ht,:,tu:ti,',-v-i?; Βε^Λ3
mit aitier Säureäun'l, v^.·., 60 v
Ö 0 ti
20O0C erhitzt und mit einem gleichen Volumen Mineralöl
vermischt und bei dieser Temperatur 2 Stünden mit Stickstoff
geblasen. Der Rückstand wird filtriert·
*ine 75?tige MineralBllttsung eines mit Polyisobuten rom
Molekulargewicht 60 000 substituierten Bernateinsäur·-
anhydride mit einer Säurezahl von 50 (1 Äquivalent) wird au einem Alkylenamin-Alkenyloyanid-Zwischenprodukt hinzugesetzt, welches man erhält» indem man 2 Äquivalent·
I-Aminoäthylpiperazin und 0,5 Äquivalente Acrylnitril bei
50 bis 1200C zur Reaktion bringt. Das sich ergebend· Oesdeeh
wird 5 Stunden bsi 150 bis 25O0C mit Stickstoff geblasen
und dann filtriert.
Es wird ein Alkylenamiil-Alkenyloyunld-Zwiechenprodukt erhalten, indem man 2 Äquivalente N-Octadecyl-propylendiamin
und 1 Äquivalent 1.2.2-TriUthylvinyl-cyanid bei 25 bis
1200O zur Reaktion bringt· Zu diesem Zwischenprodukt seist
man 1 Äquivalent einer 60jtigen Hineralöllöeung eines Beraeteinsäureanhydride mit einer Säurezahl von 100, welches
substituiert ist mit einem Isobuten-Styrol-Copolymeren
(Oewiohtsverhältnis von Isobuten zu Stjfßl *η*5) eines
00*109/1602
Molekulargewichts von 1500, Dae sick ergebende Gemisch wird
6 Stunden bei 150 bis 18O0O mit Stickstoff geblasen und
filtriert*
Eu 1 Äquivalent 1~Methyl-2-äodecylviiiyl<»cyaniü aetzt man
bei 25 bis 500C 1 Äquivalent Octamethylendiamin hinsu.
Zu diesem Reaktionsgemiacla werden dann 0,5 Äquivalente einer
9Ö$igen Mineralöllösung eines Bernateinsüureanhydrids mit
einer Süurezahl von 60 hinzugesetzt, welches mit einem
laobuten-Piperylen-Oopolyaieren (molares Verhältnis von
Isobuten zu Piperylen 98t2) vom Molekulargewicht 1000
substituiert ist. Das sich ergebende Gemisch wird 8 Stunden bei 120 bis 1800O erhitzt und filtriei-t.
Beiepiel 18
Sine 6O$ige Mineralöllöaung dea polyiaobutensubatituiertea
Bernsteinsäureanhydrids von Beiapiel 1 (1 Äquivalent) wird innerhalb eines Zeitraumea von 2 Stunden bei 50 bis 750O
tropfenweise zu einem Gemisch aua 8 Äquivalenten Heptaäthylen-octamin
und 0,2 Äquivalenten 1~Hexylvinyl~eyanid
hinzu^usetzt. Das sich ergebende Gemisch wird 3 Stunden
bei 140 bia 22O0C erhitzt und dann filtriert.
009809/1603
- Ίή -
Si« hauptsächliche Brauchbarkeit der erfindungsgOTiässen
Maeeen ist diejenige als Zusätze in Kohlenwaaeerstoffzubereitungen und Schmiermitteln, um deren Detergenteigenechaften zu verbessern und um deren Neigung aur Bildung
gefährlicher Ablagerungen zu vermindern. Beispiele von Kohlenwasserstoffen und Schmiermitteln, in welohen die
erfindungagemässen Massen brauchbar sind, sind Benzine,
Brennöle für Brenner, Schneidöle, hydraulische Flüssigkeiten und Schmieröle. Die Schmieröle können synthetischen, tierischen, pflanzlichen oder mineralischen Ursprungs sein.
Mineralschmieröle veraen wegen ihrer Verfügbarkeit, allgemeinen VortrefilichJkeit und niedrigen Kosten bevorzugt.
PUr bestimmte Anwendungen können öle, welche einer d«r
anderen drei Gruppen angehören, bevorzugt sein. Beispielsweise werden synthetische Polyesteröle wie Didodecyladipat
und Di-2-Octylsebacat cft als Schmiermittel für Düsenmaschinen bevorzugt. Gewöhnlich sind die bevorzugten
Schmieröle flüsoi-e Öle im Viakositätsbereich von etwa
40 Saybolt Universal Seconds bei 360C bis etwa 200 Saybolt
universal Second» bei 99°C.
BIe Koncentration der erflndun£Sg»*ä##en Massen «ls
Ul Schmiermitteln bewegt eioÄ e#wöhnlich tob epm 0>t
etwa 10 eew.?C. Die optimalen Kofaamtratienen tür
•ffUt/ftf 2
besondere Anwendung hängen in grossem Auamass von der
Betriebsart ab, welcher das Schmiermittel unterworfen ist. Beispielsweise können Schmiermittel zur Verwendung
in Benzinmotoren etwa 0,5 bis etwa 5$ des Additives ent-
» halten, wohingegen Schmiermittelzubereitungen zum Gebrauch in Getrieben und Dieselmotoren so viel wie 10$ oder sogar
noch mehr des Zusatzes enthalten können. Benzine oder Brennstoff öle für Brenner können so wenig wie 0,0019S
der erfindungsgemässen Masse enthalten.
Die erfindungsgemässen Massen sind besonders in Schmiermitteln brauchbar, welche der Verunreinigung durch Wasser
unterliegen können, wie sie in Motoren wie Verbrennungakraftmaschinen
von Autos und Lastwagen vorliegen« In solchen Motoren besitzen aschelose Detergents enthaltende
Schmiermittel oft eine Neigung, das Hosten von Metallteilen zu verursachen. Die erfindungsgemäsaen Massen sind insofern
einzigartig» als sie nicht- nur den Schmiermitteln
Detergenteigenschaften verleihen, sondern auch wirksam
sind, das Rosten der zu schmierenden Metallteile zu verhindern·
Die Wirksamkeit der erfindungsgemässen Massen, oxydationsinhibierende,
korrosionsinhibierende und reinigende Eigenschaften zu verleihen, wird durch die Ergebnisse aus einen
009109/1602
3AD ORIGINAL
Test veranschaulicht, bei welchem eine 350cm -Probe eines
Schmiermittels, welches 1,5 Gew.5» des zu testenden Zusatzes
enthält, für eine spezielle Zeitdauer bei 1490C in einem
5 x 38 cm-Borsilikatrohr erhitzt wird. Eine 35 x 149m·-
Tafel aus Stahl SAS 1020 ist in das Schmiermittel eingetaucht. Durch das Schmiermittel läsat man mit einer Geschwindigkeit von 10 Litern je Stunde Luft perlen· Die
oxydierte Probe wird auf 490O gekühlt, mit 0,5 Gew.36 Wasser
homogenisiert und bei Raumtemperatur stehengelassen. Sie Probe wird unter leicht vermindertem Druok
durch zwei Schichten Whätman-Pilterpapier Hr. 1 filtriert.
Der Niederschlag wird mit Naphtha gewaschen, getrocknet und gewogen. Die Menge des Schlanimniedereohlagee (ausgedrückt in Milligramm je 100 Kubikzentimeter des Schmiermittels) ist ein Merkmal für die Fähigkeit des Zusatzes,
die Bildung gefährlicher Ablagerungen im Schmiermittel zu· verhindern. Je grosser das Gewicht des Niederschlages,
um so weniger wirksam ist also der Zusatz. Bas GrundOl
des Schmiermittels ist ein herkömmlich raffiniertes Mineralöl des mittleren Kontinents mit einer Viskosität von 180
bis 200 Saybolt Universal Seconds bei 380C. Sie Ergebnisse
des Tests sind nachstehend in Tabelle I gezeigtt
00.109/1.02
aiii
Getesteter | Zusatz | Beisp. 4 | Testsseit (std.) |
Testergebnis ? mg Schlamm/1OOcnr Schmiermittel |
Keiner | Beiap. 5 | 96 | 800-1000 | |
Keiner | Beisp. 6 | 144 | 1800-2000 | |
Produkt | von | Beispο 7 |
96
144 |
5,3
7,9 |
Produkt | von | Beiapo 9 |
96
144 |
3,5
6,0 |
Produkt | von | 96 | 3 | |
Produkt | von | 96 | 3,4 | |
Produkt | von | 96 | 2,6 | |
Die rostinhibierende Eigenschaft der erfindungsgemässen Massen
wird durch einen Rosttest nach der modifizierten ASTM-Arbeitsweise B 665-54 gezeigt. Dieser Test besteht in dem Eintauchen
eines Stahlstabes in 300cnr eines Testschmiermittels, welches 5cnr "angesäuertes" Wasser enthält (angesäuert durch Auflösen
von 10g Eisessig und konzentrierter Schwefelsäure ie Liter Lösung),
Bewegen des Schmiermittels bei 600C, Entfernen des Stabes und
dessen Reinigen durch Eintauchen in Benzol und Aceton, Trocknen des Stabes, Überziehen des Stabes mit einem klaren Lack zur
Rostfixierung, und Sichten des Stabes auf Rosten«, Die Neigung
des Schmiermittels, Rost zu verursachen, wird auf einer Skala von 0 bis 10 bewertet, wobei 0 schweres Rosten auf der gesamten
001109/1602
SAD OFUGINAL
3t
Staboberflache bedeutet, und 10 keinen Rost bedeutet· Das Grund·
öl dee Te8tschmiermittela ist ein Mineralöl dee mittleren
Kontinente mit einer Viskosität von 207 Saybolt Universal Seconds bei 380C und einem Viakositäteindex yon 98. Ee enthält
4,5$ (auf das Volumen bezogen) einea Polyaorylaäuroeatere ale
viakoaltäeindexverbeaaerndea Mittel, 0,25^ einea Polyacrylsäure·
eetera als den Stookpunkt herabaetzendee Mittel, \$>
einea Zinkdialkyldithiophoaphatzuaatzea und 5# der erfindungagenäeeen
Hasee. Die Testergebnieae sind nachstehend in Tabelle Il geseigt:
Teatergebnie, Getesteter Zuaatz Bewertung
1 Äquivalent des polyieobutensubetitu-
ierten Bernsteinsäureanhydride von Beiep«1
und 1 Äquivalent dea Xthylenamingemiechea
von Beispiel 3 0
009·09/1602
Die Brauchbarkeit der diapergierenden Zusätze der Erfindung
wird gezeigt durch die Ergebnisse und die Auswertung einer modifizierten Version des Maschinenteste CRC-EX-3 (gewöhnlich
dauert dieser Maschinenteat 96 Stunden; die modifizierte
Version dauert 44 Stunden)ο Dieser Teat ist auf dem Gebiet der Schmierung als ein wichtiger Teat anerkannt, durch
welchen Schmiermittel zur Verwendung unter leichten Betriebsbedingungen ausgewertet werden können. Bei diesem
besonderen Teat wird ein Schmiermittel im Kurbelgehäuse
Haschine/ einer 1954er Sechazylinder-Chevrolet Powerglide 144 Stunden
unter wiederkehrenden zyklischen Bedingungen verwendet. Jeder Zyklus besteht aua folgendem: (A) 2 Stunden bei einer
Haachinengeschwindigkeit von 500 + 25 U/min unter Belastung
O bei einer Ölsumpftemperatur von 38 bis 520O und einem
Luft-Brennstoff-Verhältnis von 10:1j (B) 2 Stunden bei
einer Maschinengeschwindigkeit von 2500 + 25 U/min unter einer Belastung von 40 Bremspferdestärken bei einer Ölsumpftemperatur
von 71 bis 770C und einem Luft-Brennstoff-Verhältnis
von 16:1; (0) 2 Stunden bei einer Maschinenge achwind igke it von 2500 + 25 U/min unter einer Belastung
von 40 Bremapferdestärken bei einer ölsumpftemperatur
von 116 bis 1210C und einem Luft-Brennstoff-Verhältnis
von 16:1,
- BAD
009809/1602
Yi -
Am Ende des Tests wird die Maschine auseinandergenommen und auf Schlamm und Verlackung gemäse eines Bewertungssystems gesiohtet, welches sioh gründet auf: (1) da* Ausmass der Kolbenringanfüllung, (2) die Menge an in der
Maschine gebildetem Schlamm (auf einer Skala von 80 bis O9
wobei 80 keinen Schlamm angibt und 0 extrem schweren Schlamm angibt), und (3) die Gesamtmenge an Ablagerungen in der
Maschine, d.h. von in der. Maschine gebildetem Schlamm und
Lack (auf einer Skala von 100 bis 0, wobei 100 kein· Ablagerungen angibt und O extrem schwere Ablagerungen anzeigt).
Sie Wirksamkeit der erfindungsgemässen Massen ale Schmiermittelzusätze wird durch die folgenden Ergebnisse gezeigt:
Testsohmiermittel (Gew.*)
* Ring-Füllung
A. Schmiermittel, enthaltend 0,4ΐ£ dee Reaktionsproduktes des polyiaobutensubstltuierten Bernsteinsäureanhydrids von Beisp.1
(1 Äquivalent), einem Amingemisoh (1 Äquivalent), bestehend aus 7596 Triäthylentetramin und 25* Diäthylentriamin, und Acrylnitril
(0,67 Äquivalente)
Sohlt
bewertung
Bewertung der tsamtfcblaieei
75,4
92,8
001109/1102
Die erfindungsgemässen Massen sind in Schmiermitteln brauchbar,
in welchen andere Zusätze anwesend sind wie ergänzende
Detergents des aachehaltigen Typs, viskositätsindexver·
bessernde Mittel, den Stockpunkt herabsetzende Mittel, Antischaummittel, Höchstdruckmittel, rostinhibierende Mittel,
oxydationshemmende Mittel, und korrosionainhibierende Mittel.
Diese Zusätze können im Schmiermittel in Konzentrationen anwesend sein, welche sich von 0,1 bis etwa 20 Gew.$ bewegen.
Beispiele aschehaltiger Reinigungsmittel sind öllösliche neutrale und basische Salze von Alkali- oder Erdalkalimetallen mit Sulfonsäuren, Carbonsäuren oder organischen"
phosphorhaltigen Säuren, welche sich durch mindestens eine
direkte Kohlenstoff-Phosphor-Bindung auszeichnen, beispielsweise solche, welche durch Behandlung eines Olefinpolymeren
(beispielsweise Polyisobuten mit einem Molekulargewicht von
1000) mit einem Phoaphorieruntismittel wie PhosphortriChlorid,
Phosphorheptasulfid, Phosphorpentasulfid, Phosphortrichlorid
und Schwefel, weieser Phosphor und Schwefelhalogenid, oder Phoaphorthiochlorid hergestellt werden. Die am üblichsten
verwendeten Salze solcher Säuren sind die Salze des Natriums, Kaliums, Lithiums, Calciums, Magnesiums, Strontiums, und
Bariums <>
009609/1602 sad original
JtO
Der Auedruok "baaieohee SaIs*1 bezeichnet die Me tall salze,
in welchen das Metall in atöchiometrisch grosseren Mengen
vorhanden iat als das organische Säureradikal. Zu den gewöhnlich angewendeten Methoden eur Herateilung der basischen
Salze gehört das Erhitzen einer Mineralöllösung einer Säure mit einem atöchiometriaohen Überschuss eines metallhaltigen
Neutraliaierungsmittela wie Metalloxyd, -hydroxyd, -earborat,
-bicarbonat oder -sulfid bei einer Temperatur'von etwa 50cC
und daa Filtrieren der sich ergebende Masse. Die Anwendung eines "Förderers" bei der Neutralisation zur Unterstützung
der Einverleibung eines groaeen MetallUberachussea ist ebenfalls bekannt. Zu'Beispielen von Verbindungen, welche als
Förderer brauchbar sind, zählen phenolisohe Substanzen
wie Phenol, Naphtholv Alkylphenol, Thiophenol, geschwefeltes
Alkylphenol und Kondenaationeprodukte von Formaldehyd mit
einer phenolischen Substanz; Alkohole wie Methanol, 2-Propanol, Octylalkohol, Gellosolve, Carbitol, Äthylenglyool,
Stearylalkohol und Gyclohexylalkohol; Amine wie Anilin, Phenylendiamine Phenothiazin, Phenyl-fl-naphthylamin und
Dodecylamin. Eine besonders wirksame Methode zur Herstellung der basischen Salze besteht in dem Vermischen einer Säure
mit einem Überschuss eines basisohen Erdalkalimetallneutralieierungsmittels, einer phenolischen Förderverbindung
009609/1602 BAD
und einer kleinen Menge Wasser und dem "Carbonisieren" (Versetzen mit Kohlensäure) des Gemisches bei einer erhöhten
Temperatur wie 60 bis 20O0C.
Bin ergänzendes ascheloaes Detergent kann in den Schmiermittelzubereitungen
ebenfalle verwendet werden. Es ist vorzugsweise ein acyliertee Polyamin, wie es in der USA-Patentanmeldung
Kr. 802 667 vom 30. März 1959 beschrieben ist. Bas acylierte Polyarain kann gebildet werden durch die Um
setzung einer hochmolekularen» kohlenwasserstoffsubstituierten
Bernsteinsäure oder deren Anhydrid, d.h. einer Succinverbindung, welche mindestens etwa 50 aliphatische Kohlenstoffatome
im Kohlenwasserstoffsubstituenten aufweist, mit zumindest etwa 0,5 Äquivalent eines Alkylenpolyamins wie
Äthylendiarain oder eines Polyäthylenpolyamins· Besonders
brauchbar in den erfindungsgemössen Schmiermittelzubs*-
reitungen ist ein acyliertes Polyamin, welches man gewinnt,
indem man bei 100 bis 25O0C ein mit Polyisobuten rom Molekulargewicht
von etwa 700 bis 5000 substituiertes Bernsteinsäureanhydrid und etwa eine äquivalente Menge eines PoIyäthylenpolyamins
mit 2 bis etwa 8 Aminogruppen erhitzt.
Beispiele von Höchstdruckmitteln, kor^osionsinhibierenden
Mitteln und oxydationsheumenden Mitteln sind: chlorierte
000609/1002
-Affe
aliphatische Kohlenwasserstoffe wie chloriertes Wache;
organische Sulfide und Polysulfide wie Benzyldisulfid,
bis-(Chlorbenzyl)disulfid, Dlbutyl-tetrasulfid, gesohwefeltes
Spermöl, gesohwefelter Methyleeter der ölsäure, geschwefeltes
Alkylphenol, gesohwefeltes Dipenten und geschwefeltes Terpenj
phosphorgeschwefelte Kohlenwasserstoffe wie das Reaktioneprodukt eines Phosphorsulfids mit Terpentin oder Methyl»
oleät; Beter phosphoriger Säuren einschliesslich in der
Hauptsaohe von ^kohlenwasserstoff- und Trikohlenwasser-8toffphosphiten wie Mbutylphosphit, Diheptylphospnlt,
Dioyolohexylphosphlt, Pentylphenylphoaphit, Dipentylphenylphosphit, Tridecylphosphit, Distearylphosphit, Dieethylnaphthylphosphit, Oleyl-4-pentylphenylphosphit, mit Polypropylen vom Molekulargewicht 500 substituiertes Phenylphosphit, mit Isobutyl zweifach substituiertes Phenylphosphit; Metallthiooarbamate wie Zink-diootyl-dithlooarbamat
und Barium-heptylphenyl-dithiooarbamat; Bithiophosphate von
Metallen der Gruppe II wie Zink-dioyclohexyl-dithiophosphat,
Zink-dioctyldithiophoephat, Barlum-di(heptylphenyl)dithiophosphat, Cadmium-dinonyl-dithiophosphat, und Zinksais
einer Dithiophoephoreäure, welche durch die Reaktion von
Phosphorpentaeulfid mit einem äquimolaren Gemisch von Isopropylalkohol und n-Hexylalkohol hergeeteilt wurde.
001109/1602 °AD
Die folgenden Beispiele veranschaulichen die Schmifc rmittel«
zubereitungen dieser Erfindung, wobei sich alle Prozentangaben auf das Gewicht beziehen:
MineralBohmieröl SAE 20 mit einem Gehalt an 0,5$ der Masse
von Beispiel 1.
Mineralaohmieröl SÄE 30 mit einem Gehalt an 0,75?' der Hasse
von Beispiel 2 und 0,1$ Phosphor als Bariumsalz der Di-n-Nonyldithiophosphorsäure.
MineralBchmieröl SAE 30 mit einem Gehalt an 5$ der Masse
von Beispiel 5» 0,1$ Phosphor als Zinksalz eines Gemisches
äquimolarer Mengen von Di-Isopropyl-dithiophosphorsäure
und Di-n-Decyl-dithiophosphorsaure, und 2,5$ Sulfataache
ale basisches Bariumreinigungsmittel, welches hergestellt wurde durch Carbonisieren eines Gemisches aus Mineralöl,
Barium-didodecylbenzolsulfonat und 1,5 Mol Bariumhydroxyd
in Gegenwart einer kleinen Menge Wasser und 0,7 Mol Octylphenol
als Förderer, bei 0
00S809/16Q2 BAD
J*
Mineralsohmierbl SAE 10W-30 mit einem Gehalt an 6£ der
Hasse von Beispiel 6, O,O75# Phosphor als Zink-di-n-octyldithiophosphat und 5# des Bariumsalze8 einer sauren Masse,
welche bereitet wurde durch Umsetzen von 1000 Teilen eines Polyisobutene eines Molekulargewichtes von 60 000 mit 100
Teilen Fhosphorpentasulfid bei 2000C, und Hydrolysieren des
Produktes mit Dampf bei 1500C.
Mineralschmieröl SAE 20 mit einem Gehalt an 35* eines acylierten Polyamine, welchee man erhält, indem man bei 150 bis
2000C ein Äquivalent eines mit Polyisobuten vom Molekulargewicht 1000 substituierten Bernsteinsäureanhydride und
1 Äquivalent eines Äthylamingemisches mit einer mittleren
Zusammensetzung, welche dem Tetraäthylenpentamin entspricht, erhitzt, 1?S Zink~dioctyl-dithiophosphat und 2# der Masse
von Beispiel 1.
Es ist ersichtlich, dass nach der angewandten Method· but
Herstellung der "kohlenwasserstoffsubstituierten, berneteinsaurebildenden Verbindung", eine einzelne Kohlenwasserstoffgruppe an zwei oder mehrere Suocingruppen angegliedert sein
kann. Der Ausdruck "kohlenwasserstoffsubstituierte, bernstein-
009609/1602
aäureblldende Verbindung11 eoll hler Verbindungen dieser
Art in eich einsohlieeaen.
- Patentanspruch· -
009109/1*02 BAÜ
Claims (1)
- Patentansprüche1.) Verfahren zur Herstellung stickstoffhaltiger Hassen, dadurch gekennzeichnet, dass man eine kohlenwasserstoff -substituierte, berneteinsUurebildende Verbindung Bit Mindestens etwa 50 aliphatischen Kohlenstoffatomen im Kohlenwasserstoffsubstituenten, mit mindestens etwa 0,5 Äquivalenten eines Alkylenamins und zumindest etwa 0,1 Äquivalenten eines Alkenyloyanids zur Reaktion bringt·2.) Verfahren nach Ansprach 1, daduroh gekennseiohnet, dass das Alkylenamin ein Xthylenamln ist.3·) Verfahren nach Anspruch 1, dadaroh gekennseiohnet, dass das. Alkylenamin ein Polyathylen-polyamin ist·4·) Verfahren nach Anspruch 1, dadurch gekennseiohnet, dass die kohlenwasserstoffsubstituierte, bernsteinsaurebildende Verbindung ein öleflnpolyasreubstituiertte Bernsteinsäureanhydrid ist.5·) Verfahren nach Anspruch 1, dadurch.gekennseiohnet, dass dis kohlenwasserstoffsubstituiertet beraeteineäure-OOIiOS/1102bildende Verbindung ein polyisobutenaubstituiertes Bernsteinsäureanhydrid iSt O6.) Verfahren nach Anspruch 1, dadurch gekennzeichnet, dass dae Alkenylcyanid ein Vinylcyanid iat.7o) Verfahren nach Anspruch 1, daduroh gekennzeichnet, dase das Alkenylcyanid Acrylnitril ist»8·) Verfahren zur Herstellung stickstoffhaltiger Hassen, dadurch gekennzeichnet, dass man ein isobutenpolymersubstituiertes Bernsteinsäureanhydrid, in welchem der iBobutenpolymeraubstituent ein Molekulargewicht von etwa 750 bis 5000 aufweist} mit mindestens etwa 0,5 Äquivalenten eines Äthylenarains und zumindest etwa 0,1 Äquivalent eines Vinylcyanids zur Reaktion bringt09.) Verfahren nach Anspruch 8, dadurch gekennzeichnet, dass das Äthylenamin ein Polyäthylen-polyamin ist.10.) Verfahren nach Anspruch 8, dadurch gekennzeichnet, dass das Äthylenamin Tetraäthylen-pentamin ist.BAD009809/160211.) Verfahren naoh Anspruch 8, dadurch gekennzeichnet, dass der iBobutenpolymersubstituent eine Polyieobutenyl*- gruppe mit einem Molekulargewicht Ton etwa 1000 ist.12.) Verfahren nach Anepruoh 8, dadurch gekennselehnet, daas dae Vinyloyanid Acrylnitril ist. ,13.) Verfahren zur Herstellung stickstoffhaltiger Massen» dadurch gekenneeiehnet, dass man ein polyieobuteneubetitulertee Bernsteinsäureanhydrid, in welohem der Polyiso- butensubstltuent ein Molekulargewicht ron etwa 750 bis 5000 aufweist, alt mindestens etwa 0,5 »bis 5 Äquivalenten eines Polyäthylen-polyanins und etwa O95 bis 4 Äquivalenten Acrylnitril but Reaktion bringt.14·) Verfahren nach Anepruoh 13, dadurch gekennzeichnet, dass das Polyäthylen-polyeain eine mittlere Zusanaeneetsung beeitzt, weiche derjenigen des Tetraäthylen-penta-■ine entspricht.15·) Verfahren zur Herstellung stickstoffhaltiger flaaeen, dadaroh gekennzeichnet, does man ein polyieobutensubetituiertee Bernsteinsäureanhydrid, in welchem der Polylsobutensubetituent ein Molekulargewicht von etwa 1000 besitst,001109/1602nit etwa 1 bis 2 Äquivalenten eines Polyäthylen-polyamins einer mittleren Zusammensetzung, welche derjenigen von Tetraäthylen-pentamin entspricht, und mit etwa 0,5 bis 2 Äquivalenten Acrylnitril zur Reaktion bringt.16.) Produkt dee Verfahrens nach Anspruch 1· 17·) Produkt des Verfahrens nach Anspruch 15·18.) Schmiermittelzubereitung» bestehend aus b«w. enthaltend einen überwiegenden Anteil eines Schmieröls und einen untergeordneten Anteil des Produktes des Verfahrene nach Anspruch 1.19.) Scnmieraittelzubereltungi bestehend aus b*w. enthaltend einen überwiegenden Anteil eines Schmieröle und einen untergeordneten Anteil des Produktes des Verfahrene nach Anspruch 15.BAD00*109/1*02
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US80266759 US3172892A (en) | 1959-03-30 | 1959-03-30 | Reaction product of high molecular weight succinic acids and succinic anhydrides with an ethylene poly- amine |
US12680961 US3219666A (en) | 1959-03-30 | 1961-07-21 | Derivatives of succinic acids and nitrogen compounds |
US348760A US3278550A (en) | 1959-03-30 | 1964-03-02 | Reaction products of a hydrocarbonsubstituted succinic acid-producing compound, an amine and an alkenyl cyanide |
US40261764A | 1964-10-08 | 1964-10-08 | |
US468948A US3341542A (en) | 1959-03-30 | 1965-07-01 | Oil soluble acrylated nitrogen compounds having a polar acyl, acylimidoyl or acyloxy group with a nitrogen atom attached directly thereto |
Publications (1)
Publication Number | Publication Date |
---|---|
DE1570871A1 true DE1570871A1 (de) | 1970-02-26 |
Family
ID=27537768
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DENDAT1248643D Pending DE1248643B (de) | 1959-03-30 | Verfahren zur Herstellung von öllöslichen aeylierten Aminen | |
DE19601794292D Pending DE1794292B1 (de) | 1959-03-30 | 1960-01-07 | Schmiermittel auf Mineralschmieroelbasis |
DE1965L0050105 Pending DE1570871A1 (de) | 1959-03-30 | 1965-03-02 | Verfahren zur Herstellung stickstoffhaltiger Massen,welche als Zusaetze in Kohlenwasserstoffoelen brauchbar sind |
Family Applications Before (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DENDAT1248643D Pending DE1248643B (de) | 1959-03-30 | Verfahren zur Herstellung von öllöslichen aeylierten Aminen | |
DE19601794292D Pending DE1794292B1 (de) | 1959-03-30 | 1960-01-07 | Schmiermittel auf Mineralschmieroelbasis |
Country Status (5)
Country | Link |
---|---|
US (4) | US3172892A (de) |
DE (3) | DE1794292B1 (de) |
FR (1) | FR1432851A (de) |
GB (1) | GB922831A (de) |
NL (1) | NL6502540A (de) |
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Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2490744A (en) * | 1947-02-08 | 1949-12-06 | Socony Vacuum Oil Co Inc | Antirust agent |
US2604451A (en) * | 1948-09-16 | 1952-07-22 | Gulf Research Development Co | Mineral oil compositions |
US2638450A (en) * | 1950-01-17 | 1953-05-12 | Socony Vacuum Oil Co Inc | Reaction products of nu-alkylated polyalkylenepolyamines and alkenyl succinic acid anhydrides |
US2833757A (en) * | 1953-10-12 | 1958-05-06 | Atlas Powder Co | N-cyanoalkyl hexityl amines |
US3004987A (en) * | 1957-08-15 | 1961-10-17 | Monsanto Chemicals | Acyclic substituted succinic anhydride condensed with diamines |
NL255193A (de) * | 1959-08-24 | |||
NL255194A (de) * | 1959-08-24 | |||
NL255251A (de) * | 1959-08-28 | |||
US3029250A (en) * | 1959-09-03 | 1962-04-10 | Monsanto Chemicals | Succinimide compounds |
-
0
- DE DENDAT1248643D patent/DE1248643B/de active Pending
-
1959
- 1959-03-30 US US80266759 patent/US3172892A/en not_active Expired - Lifetime
- 1959-12-23 GB GB43717/59A patent/GB922831A/en not_active Expired
-
1960
- 1960-01-07 DE DE19601794292D patent/DE1794292B1/de active Pending
-
1961
- 1961-07-21 US US12680961 patent/US3219666A/en not_active Expired - Lifetime
-
1964
- 1964-03-02 US US348760A patent/US3278550A/en not_active Expired - Lifetime
-
1965
- 1965-03-01 FR FR7499A patent/FR1432851A/fr not_active Expired
- 1965-03-01 NL NL6502540A patent/NL6502540A/xx unknown
- 1965-03-02 DE DE1965L0050105 patent/DE1570871A1/de active Pending
- 1965-07-01 US US468948A patent/US3341542A/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
US3341542A (en) | 1967-09-12 |
US3172892A (en) | 1965-03-09 |
GB922831A (en) | 1963-04-03 |
FR1432851A (fr) | 1966-03-25 |
NL6502540A (de) | 1965-09-03 |
US3219666A (en) | 1965-11-23 |
DE1248643B (de) | 1967-08-31 |
DE1794292B1 (de) | 1970-07-23 |
US3278550A (en) | 1966-10-11 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
SH | Request for examination between 03.10.1968 and 22.04.1971 |