DE1284014B - Schmieroel - Google Patents

Schmieroel

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Publication number
DE1284014B
DE1284014B DEM61680A DEM0061680A DE1284014B DE 1284014 B DE1284014 B DE 1284014B DE M61680 A DEM61680 A DE M61680A DE M0061680 A DEM0061680 A DE M0061680A DE 1284014 B DE1284014 B DE 1284014B
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Germany
Prior art keywords
ketone
methyl
polybutenyl
succinimido
product
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
DEM61680A
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English (en)
Inventor
Davis James Bradley
Anzenberger Joseph Francis
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.)
Monsanto Co
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Monsanto Co
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Publication date
Application filed by Monsanto Co filed Critical Monsanto Co
Publication of DE1284014B publication Critical patent/DE1284014B/de
Pending legal-status Critical Current

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  • Chemical & Material Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Lubricants (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Pyrrole Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Description

Alkenylbernsteinsäureimide sind als Schmierölzusätze hinreichend bekannt. Sie haben jedoch den Nachteil, daß sie zur Bildung ölunlöslicher Oxydationsprodukte neigen, die störende Ablagerungen, beispielsweise in Verbrennungsmotoren, verursachen. Es wurde gefunden, daß dieser Nachteil beseitigt wird, wenn man einem Schmieröl ein l-Polyalkenylsuccinimidoimidazolidin der Formel
O
Il 		S. f CH2- -NH I
R-CH Il
— Cn 		\
N —
/
/
CH; 1 Ϊ
O
-CH-
R1
H2C-
— CH2 — CH — N
R1
R1
-CH
C-R2
R3
worin R ein Olefinpolymerisat mit einem Molekulargewicht von 500 bis 2500 und χ eine ganze Zahl von 0 bis 3 ist und, wenn η = 1, R1 Wasserstoff und/oder einen niederen Alkylrest bedeutet, R2 und R3 Wasserstoff, Alkyl, Alkenyl und/oder Haloalkyl und, wenn η = 2, R2 nur Wasserstoff und/oder niederes Alkyl und R3 Alkylen oder Alkenylen von 1 bis 16 Kohlenstoffatomen ist, zusetzt.
Die Imidazoline werden hergestellt durch Umsetzen
(a) eines Alkenylbernsteinsäureanhydrids oder der Säure derselben,
(b) eines Polyäthylenamins, dargestellt durch die Struktur
H2N
ptt /"1U TvTU CU ,
35
CH — NH — CH2 — CH-NH2 R1 Rj
und
(c) einer Carbonyl enthaltenden Verbindung, d. h. eines Aldehyds oder Ketons, dargestellt durch die Struktur
oder eines Dialdehyds oder Diketons, dargestellt durch die Struktur
O O
V^ £-1 K^
1x4
rc
worin R, R1, R2, R3, R4, χ und Z die gleiche Bedeutung haben. Die verwendeten Molverhältnisse von (a): (b): (c) können ungefähr 1:1:1, um mono-Imidazolidine herzustellen, und ungefähr 2:.2:1, um bis-Imidazolidine herzustellen, haben. Normalerweise werden (b) und (c) umgesetzt, um ein Zwischenproduktimidazolidin herzustellen, welches mit (a) umgesetzt wird, um die Verbindungen dieser Erfindung herzustellen. Um ein .Reaktionsmedium zu schaffen und das Entfernen des Wassers der Reaktion zu erleichtern, kann ein Kohlenwasserstofflösungsmittel, z.B. Toluol oder Xylol, verwendet werden.
Ebenso kann ein mineralisches öl als Reaktionsmedium entweder allein oder zusammen mit einem Kohlenwasserstofflösungsmittel verwendet werden. Geeignete Temperaturen zur Herstellung von Imidazolidinen bei atmosphärischem Druck liegen im Bereich von 100 bis 175° C, und es kann im Falle eines Mineralölreaktionsmediums Vakuum verwendet werden, um unter ungefähr den gleichen Temperaturen zu arbeiten.
Die Alkenylbernsteinsäureanhydride werden nach den üblichen Methoden hergestellt.
Polyäthylenamine sind z. B. Diäthylentriamin, Di-(methyläthylen) - triamin, Triäthylentetramin, Tri-(methyläthylen)-tetramin, Tri-(äthyläthylen)-tetramin, Tetraäthylenpentamin und Pentaäthylenhexamin.
Carbonyl und Dicarbonyl enthaltende Verbindungen sind z. B.
Aldehyde, wie Formaldehyd, Acetaldehyd, Propionaldehyd, n-Butyraldehyd, Isobutyraldehyd, η - Valeraldehyd, Isovaleraldehyd, Pivaldehyd, alpha - Methylbutyraldehyd, Caproaldehyd, tert. Butylacetaldehyd, Heptaldehyd, Pelagonaldehyd,Nonaldehyd, Capraldehyd, Lauraldehyd, Tridecanal, Myristaldehyd, Pentadecanal, Palmitaldehyd, Heptodecanal, Stearaldehyd; substituierte Aldehyde, wie Chloracetaldehyd, Chloral, Butylchloral, Trifluoracetaldehyd, Aldol, 2-Hydroxypropionaldehyd; ungesättigte Aldehyde, wie Methacrolein, Acrolein, Crotonaldehyd, 3-Butenal, 3- und 4-Pentenal, 3-, 4- und 5-Hexenal, 4-Octenal, 2-Äthyl-3-hexenal, 3-Decenal, wobei solche, in denen die ungesättigte Stelle nicht in 2-, 3-Stellung ist, oft bevorzugt werden;
Ketone, wie Aceton, Methyl-äthyl-keton, Methylpropyl-keton, Methyl-isopropyl-keton, Methylbutyl-keton, Methyl-isobutyl-keton, Methylsek. butyl - keton, Methyl - tert. butyl - keton, Methyl - cyclobutyl - keton, Methyl - neopentylketon, Methyl-tert.amyl-keton, Methyl-n-amylketon, Methyl - hexyl - keton, Methyl - cyclohexyl-keton, Methyl-n-heptyl-keton, Methyln-octyl-keton, Methyl-nonyl-keton, Methyldecyl-keton, Diäthyl-keton, Di-n-propyl-keton, Diisopropyl - keton, Äthyl - isopropyl - keton, Äthyl - η - propyl - keton, Äthyl - tert. butyl - keton, Äthyl - η - butyl - keton, tert. Butyl - isopropylketon, η - Propyl - isopropyl - keton, η - Propyltert.butyl-keton, Diisobutyl-keton, 2-Decanon; substituierte Ketone, wie 3- und 4-Methyl-2-hexanon, 3,4 - Dimethyl - 2 - pentanon, 3 - Äthyl-2-pentanon; ungesättigte Ketone, wie Allylaceton,
2- und 3-Methyl-l-penten-4-on, l-Hepten-4-on, 3-Methyl-l-hexen-S-on, 5-Methyl-5-hexen-2-on; oder
a) Aldehyde, wie Glyoxal, Malonaldehyd, Succinaldehyd, Glutaraldehyd, Adipaldehyd, Pimelaldehyd, Suberaldehyd, Azelaldehyd, Sebacaldehyd, Brassaldehyd, Brassylaldehyd, Rocellaldehyd; ungesättigte di-Aldehyde, wie Malealdehyd, Glutaconaldehyd;
b) Ketone, wie Diacetyl, Acetylaceton, Acetonylaceton, 2,3-Hexandion, 2,4-Heptandion, 3-Methyl-2,4-hexandion, 2,5-Hexandion, 2,3-Octandion.
Ein detailliertes allgemeines Herstellungsverfahren der Imidazolidine dieser Erfindung verläuft wie folgt:
Beispiel 1
In einem Reaktionskolben wurden 23,3 g Tetraäthylenpentamin (0,1234 Mol) und ungefähr 80 ml
Toluol eingebracht. Unter Rühren wurden dann 8,9 g n-Butyraldehyd (0,1234 Mol) langsam eingebracht und das sich ergebende Gemisch am Rückfluß ungefähr 2 Stunden erhitzt, wobei das durch die Reaktion gebildete Wasser entfernt wurde.
Nach Abkühlen wurden 169 Teile (0,1234MoI) eines Polybutenylbernsteinsäureanhydrids (Alkenylrest mit einem Durchschnittsmolekulargewicht von ungefähr 980) in 100-ml Toluol langsam eingebracht, und das Gemisch wurde am Rückfluß ungefähr 2 Stunden unter Entfernung des Wassers erhitzt.
Das Toluol wurde im Vakuum abgestreift, 1 - [8 - (Polybutenylbernsteinimido) - 3,6 - diazaoctyl]-2-propylimidazolidin blieben zurück.
In der Tabelle I bedeutet:.
DETA = Diäthylentriamin,
TETA = Triäthylentetramin und
TEPA = Tetraäthylenpentamin.
Tabelle I
Alkenylanteil des Polyäthylen- Carbonyl enthaltende Molar
verhältnis		 Produkt
Bei- Alkenylbernsteinsäure-
anhydrids (a)		 amin (b) Verbindung (c) (a):(b):(c)
spiel (Molekulargewicht der
Alkenylgruppe) TEPA Formaldehyd 1:1:1 1 -[8-(Polybutenylsuccinimido)-
Polybutenyl (980) 3,6-diazaoctyl]-imidazolidin
TEPA Acetaldehyd 1:1:1 1 -[8-(Polybutenylsuccinimido)-
3 Polybutenyl (980) 3,6-diazaoctyl]-2-methyl-
imidazolidin
TEPA Isodecylaldehyd 1:1:1 1 -[8-(Polybutenylsuccinimido)-
4 Polybutenyl (980) 3,6-diazaoctyl]-2-nonyl-
imidazolidin
DETA Glutaraldehyd 2:2:1 Trimethylen-bis-[l -(8-(poly-
5 Polybutenyl (1190) butenylsuccinimido)-3,6-diaza-
octyl)-2-imidazolidin]
TEPA Aceton 1:1:1 1 -[8-(Polybutenylsuccinimido)-
6 Polybuteny] (980) 3,6-diazaoctyl]-2-dimethyl-
imidazolidin
TEPA Cyclohexanon 1:1:1 1 -[8-(Polybutenylsuccinimido)-
7 Polybutenyl (980) 3,6-diazaoctyl]-1,4-diazaspiro-
[4,,5]-decan
DETA Acetylaceton 2:2:1 2,2'-Methylen-bis-[l-((8-poly-
8 Polybutenyl (980) butenylsuccinimido)-3,6-diaza-
octyl)-imidazolidin]
DETA Glutaraldehyd 2:2:1 Trimethylen-bis-[l-(2-(poly-
9 Polybutenyl (1315) butenylsuccinimido)-äthyl)-
2-imidazolidin]
TEPA n-Butyraldehyd 1:1:1 1 -[8-(Polybutenylsuccinimido)-
10 Polybutenyl (1315) 3,6-diazaoctyl]-2-propyl-
imidazolidin
DETA n-Butyraldehyd 1:1:1 1 -[2-(Polybutenylsuccinimido)-
11 Polybutenyl (980) äthyl]-2-propylimidazolidin
DETA 2-Propenal 1:1:1 1 -[2-(Polybutenylsuccinimido)-
12 Polybutenyl (980) äthyl]-2-vinylimidazolidin
TETA 2-Methyl-2-pro- 1:1:1 1 -[5-(Polybutenylsuccinimido)-
13 Polybutenyl (980) penal 3-azapentyl]-2-(/3-allyl)-
imidazolidin
TEPA 2-Butenal 1:1:1 1 -[8-(Polybutenylsuccinimido)-
14 Polybutenyl (980) 3,6-diazaoctyl]-2-propenyl-
imidazoüdin
Als Basisschmieröle werden natürliche oder synthetische öle verwendet.
Die Imidazolidine und bis-Imidazolidine dieser Erfindung werden diesen Schmierölen in Mengen von 0,05 bis 25 Gewichtsprozent zugesetzt.
Die Wirksamkeit der Imidazolidine dieser Erfindung, welche Niedertemperatur - Reinigungseigenschaften verleihen, wird durch die Ergebnisse eines Reinigungsversuchs erläutert, der in der Literatur als »Lackablagerungstest« bezeichnet wird und darin to besteht, daß abgebrannte Gasolindämpfe durch eine Probe einer Zubereitung in einem geeigneten Behälter unter Kontrollbedingungen durchgeleitet werden, wonach die Probe in einem Ofen gealtert wird. Die Ablagerungsmenge wird dann durch Auswaschen des Öls mit Hexan bestimmt. Eine Kontrollzubereitung wird in gleicher Weise behandelt. Die Menge der vorhandenen Ablagerungen, wenn das Untersuchungsreinigungsmittel verwendet wird, im Vergleich zu der Menge der Ablagerungen, die vorhanden sind, wenn kein Reinigungsmittel verwendet wird, wird als Prozent der Ablagerungsverringerung aufgezeigt. Bei Verwenden des oben angegebenen Versuchs wurden die in der untenstehenden Tabelle II dargestellten Ergebnisse erhalten.
Tabelle II
R-CH CS
CH.-C-
Additiv . Gewichts Lackablagerungs
test prozentuale
prozent Verringerung
Produkt von Beispiel 1 ... 2 100
Produkt von Beispiel 2 ... 2 92
Produkt von Beispiel 3 ... 2 94
Produkt von Beispiel 4... 2 100
Produkt von Beispiel 5 ... 2 69
Produkt von Beispiel 6 ... 2 90
Produkt von Beispiel 7 ... 2 94
Produkt von Beispiel 8... 2 98
Produkt von Beispiel 9 ... 2 69
Produkt von Beispiel 10 .. 1 99
Produkt von Beispiel 11.. 2 98

Claims (1)

  1. Patentanspruch:
    Schmieröl, gekennzeichnet durch einen Gehall an l-Polyalkenylsuccinimidoimidazolidin der Formel
    N —
    CH2
    -CH-NH H2C-
    -CH2-CH-N
    R1
    C-
    R1 CH
    R2
    R3
    worin R ein Olefinpolymerisat mit einem Molekulargewicht von 500 bis 2500 und .v eine ganze Zahl von 0 bis 3 ist und, wenn η = 1. R1 Wasserstoff und oder einen niederen Alkylrest bedeutet.
    R2 und R3 Wasserstoff, Alkyl, Alkenyl und/oder Haloalkyl und, wenn η = 2, R2 nur Wasserstoff und'oder niederes Alkyl und R3 Alkylen oder Alkenylen von 1 bis 16 Kohlenstoffatomen ist.
DEM61680A 1963-07-22 1964-07-10 Schmieroel Pending DE1284014B (de)

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US29648963A 1963-07-22 1963-07-22
US312292A US3280034A (en) 1963-07-22 1963-09-30 Alkenylsuccinimido alkyl-substituted imidazolidines and related materials

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Families Citing this family (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3415750A (en) * 1963-10-04 1968-12-10 Monsanto Co Imidazolines having polyalkenylsuccinimido-containing substituents
US3497334A (en) * 1963-12-16 1970-02-24 Mobil Oil Corp Liquid hydrocarbon combustion fuels
US3390086A (en) * 1964-12-29 1968-06-25 Exxon Research Engineering Co Sulfur containing ashless disperant
US3369021A (en) * 1966-03-07 1968-02-13 Lubrizol Corp Preparation of lubricant additives with reduced odor
US3445386A (en) * 1967-01-13 1969-05-20 Mobil Oil Corp Detergent compositions
US4579675A (en) * 1983-11-09 1986-04-01 Texaco Inc. N-substituted enaminones and oleaginous compositions containing same
US4906252A (en) * 1987-05-18 1990-03-06 Exxon Chemical Patents Inc. Polyolefinic succinimide polyamine alkyl acetoacetate adducts as dispersants in fuel oil compositions
US4839071A (en) * 1987-05-18 1989-06-13 Exxon Chemical Patents Inc. Polyolefinic succinimide polyamine alkyl acetoacetate adducts as dispersants in lubricating oil compositions
US4839073A (en) * 1987-05-18 1989-06-13 Exxon Chemical Patents Inc. Polyolefinic succinimide polyamine alkyl acetoacetate and substituted acetate adducts as compatibilizer additives in lubricating oil compositions
CA1339530C (en) * 1987-05-18 1997-11-04 Antonio Gutierrez Polyolefinic succinimide polyamine alkyl acetoacetate adduct dispersants
US4839072A (en) * 1987-05-18 1989-06-13 Exxon Chemical Patents Inc. Polyolefinic succinimide polyamine alkyl acetoacetate adducts
US4839070A (en) * 1987-05-18 1989-06-13 Exxon Chemical Patents Inc. Polyolefinic succinimide polyamine alkyl acetoacetate adduct dispersants
US5158696A (en) * 1989-01-30 1992-10-27 Exxon Chemical Patents Inc. Oil soluble dispersant additives modified with bis-keto/thioketo compounds
US5273668A (en) * 1989-01-30 1993-12-28 Exxon Chemical Patents Inc. Oil soluble dispersant additives modified with bis-keto/thioketo compounds
GB8911732D0 (en) 1989-05-22 1989-07-05 Ethyl Petroleum Additives Ltd Lubricant compositions
US5646098A (en) * 1990-07-23 1997-07-08 Exxon Chemical Patents Inc Carbonyl containing compounds and their derivatives as multi-functional fuel and lube additives
US5643859A (en) * 1992-12-17 1997-07-01 Exxon Chemical Patents Inc. Derivatives of polyamines with one primary amine and secondary of tertiary amines
IL107810A0 (en) * 1992-12-17 1994-02-27 Exxon Chemical Patents Inc Functionalized polymers and processes for the preparation thereof
US5650536A (en) * 1992-12-17 1997-07-22 Exxon Chemical Patents Inc. Continuous process for production of functionalized olefins
US5646332A (en) * 1992-12-17 1997-07-08 Exxon Chemical Patents Inc. Batch Koch carbonylation process
US5767046A (en) * 1994-06-17 1998-06-16 Exxon Chemical Company Functionalized additives useful in two-cycle engines
US6043199A (en) * 1997-08-26 2000-03-28 Exxon Research And Engineering Co. Corrosion inhibiting additive combination for turbine oils
EP1143744B1 (de) * 2000-03-17 2008-09-24 Hitachi, Ltd. Bildanzeigevorrichtung
US7947636B2 (en) 2004-02-27 2011-05-24 Afton Chemical Corporation Power transmission fluids
US7563314B2 (en) * 2005-11-30 2009-07-21 Xerox Corporation Ink carriers containing nanoparticles, phase change inks including same and methods for making same
US7655084B2 (en) * 2005-12-12 2010-02-02 Xerox Corporation Carbon black inks and method for making same
US7786209B2 (en) * 2006-10-27 2010-08-31 Xerox Corporation Nanostructured particles, phase change inks including same and methods for making same
US20080098930A1 (en) * 2006-11-01 2008-05-01 Xerox Corporation Colorant dispersant
US8123344B2 (en) * 2008-08-04 2012-02-28 Xerox Corporation Ink carriers containing surface modified nanoparticles, phase change inks including same, and methods for making same
US8029861B2 (en) * 2008-09-23 2011-10-04 Xerox Corporation Ink carriers containing low viscosity functionalized waxes, phase change inks including same, and methods for making same
US8177897B2 (en) * 2008-11-17 2012-05-15 Xerox Corporation Phase change inks containing graphene-based carbon allotrope colorants

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1254094A (fr) * 1960-03-29 1961-02-17 Lubrizol Corp Additifs exempts de métaux pour lubrifiants
FR1265085A (fr) * 1959-08-24 1961-06-23 California Research Corp Compositions d'huiles lubrifiantes renfermant des n-dialkylaminoalkyl alkényl succinimides

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2877179A (en) * 1956-03-26 1959-03-10 Cities Service Res & Dev Co Composition for and method of inhibiting corrosion of metals
FR1265086A (fr) * 1959-08-24 1961-06-23 California Research Corp Compositions d'huiles lubrifiantes renfermant des alkényl succinimides de la tétraéthylène pentamine
US3131150A (en) * 1961-04-12 1964-04-28 California Research Corp Lubricating oil compositions containing n-substituted alkenyl succinimides in combination with polyamines
US3087936A (en) * 1961-08-18 1963-04-30 Lubrizol Corp Reaction product of an aliphatic olefinpolymer-succinic acid producing compound with an amine and reacting the resulting product with a boron compound

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1265085A (fr) * 1959-08-24 1961-06-23 California Research Corp Compositions d'huiles lubrifiantes renfermant des n-dialkylaminoalkyl alkényl succinimides
FR1254094A (fr) * 1960-03-29 1961-02-17 Lubrizol Corp Additifs exempts de métaux pour lubrifiants

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BE650770A (de) 1964-11-16
US3280034A (en) 1966-10-18

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