DE1520879A1 - Alkyl- oder alkenylsubstituiertes aliphatisches Polyamin - Google Patents
Alkyl- oder alkenylsubstituiertes aliphatisches PolyaminInfo
- Publication number
- DE1520879A1 DE1520879A1 DE1964S0092408 DES0092408A DE1520879A1 DE 1520879 A1 DE1520879 A1 DE 1520879A1 DE 1964S0092408 DE1964S0092408 DE 1964S0092408 DE S0092408 A DES0092408 A DE S0092408A DE 1520879 A1 DE1520879 A1 DE 1520879A1
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- polyamine
- alkenyl
- oil
- alkenyl group
- 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.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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
- C10M133/54—Amines
-
- 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
- C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/40—Fatty vegetable or animal oils
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/40—Fatty vegetable or animal oils
- C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/26—Amines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/022—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amino group
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/046—Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
-
- 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
- C10N2070/00—Specific manufacturing methods for lubricant compositions
- C10N2070/02—Concentrating of additives
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F02—COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
- F02B—INTERNAL-COMBUSTION PISTON ENGINES; COMBUSTION ENGINES IN GENERAL
- F02B3/00—Engines characterised by air compression and subsequent fuel addition
- F02B3/06—Engines characterised by air compression and subsequent fuel addition with compression ignition
Landscapes
- 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)
Description
DR. ELISABETH JUNG, DR. VOLKER VOSSIUS, DIPL.-ING. GERHARD COLDEWEY
..6. Mai 1369
P 5865 (J /we)
SHELL INTERKAOJIONALE RESEARCH MAATSCHAPPIJ N0V0,
Ben Haag, Niederlande
H Alkyl- oder alkenylsubstituiertes aliphatisches Polyamin "
Priorität: 2„ August 1963 / Niederlande Anmelde~Nr.: 296 139
Die vorliegende Erfindung bezieht sich auf ein alkyl- oder alkenylsubstituiertes
aliphatisohes Polyamin, welches insbesondere als ein keine Asche bildender Schraierölzusatzstoff geeignet
ist.
Sie Schmierölzusatzstoffe können eingeteilt werden in eine Gruppe
aus Substanzen, welche Metallatome enthalten» beispielsweise Metallseifen von öllöslichen organischen Säuren, und in ein·
Gruppe von Verbindungen, die keine Metallatorae enthalten· Bits·
zuletzt genannte Gruppe von Zusatzstoffen weist statt der Metallatome eine polare organische Gruppe im Molekül auf, der ale 41·
909.840/1521 BAD ORIGINAL
Eigenschaft, aia Zusatzstoffe au wirken, verdanken. Vertreter ·
dieses speziellen 'fyps von Zusatzstoffen aind z.B. tertiäre
Amine mit einer sinzigen langkettigen Alkylgruppe von 10 bis 24
Kohlenstoffatomen und-mit 2 .kurzkettigen Alkylgruppen, welche
in der US «Patentschrift 2 476 271 beschrieben werden und welche
man als Antioxydationsmittel einsetzt„
Die vorliegende Erfindimg, bezieht sich nun auf neue Verbindungen!
welche einem Schmieröl reinigende Eigenschaften verleihen und außerdem in unter niedriger Belastung laufenden Motoren die
Sohlammbildung verhindern*
Das erfindungsgemäiäe alkyl» oder alkenylsubstituierte aliphatische
Polyamin ist dadurch gekennzeichnet, daß es mindestens eine
Alkyl- oder Alkenylgruppe mit mindestens 50 Kohlenstoffatomen an ein Stickstoffatom gebunden enthält«
Die neuen Zusatzstoffe gemäß der Erfindung verdanken ihre reinigenden Eigenschaften zum feil der polaren Gruppe und zum Teil
der langkettigen Alkyl- oder Alkenylgruppe, welohe eine räuraiiohe
Abstoßung anderer Sohmutsteilchen bewirkt, nachdem ein
Molekül des Zusatzstoffes mit der polaren Gruppe von einem Sohmutzteilohen oder dergleiohen adsorbiert worden ist.
Sie Alkyl- oder Alkenylgruppen können sioh von geradkettigen
oder verzweigtkettigen Alkanen odor Alkentn ableiten, die auch
aromatisch« oder oyoloaliphatlsohe Substituenten aufweisen kun~
und «β kann eioh dabei um von Olefinpolymerieaten oder
909840/152t ·, + j
IAD ORIGINAL
fr r -
-mleahpolynterisaten abgeleitete Truppen handeln, die auch eine
Doppelbindung enthalten können,
Beispiele für niehteubstituierte Alkenyl- und Alkylgruppen sind
Polyäthylengruppen, Polypropylengruppen, Polybütylen- und Polyieobutylengruppen
sowie die entsprechenden Gruppen ohne Doppelbindungen C
Obwohl vorzugsweise ein Polyamin mit einer Alkyl- oder Alkenylgruppe von 60 bis 150 Kohlenstoffatomen und insbesondere ein
Polyamin mit einer Alkyl- oder Alkenyigruppe von 80 bis 120
Kohlenstoffatomen im Rahmen <3er Erfindung verwendet wird, eignen
eich auch Polyamine mit einer Alkyl-· oder Alkenylgruppe mit
einer größeren Anzahl von Kohle net; of fat omen» ζ. B, von 500 Kohlenstoffatomen,
alB Sohfflierölzusatzstoffe.
Bei den die Alkyl- oder Alkenylgruppe baw« -gruppen tragenden
Polyaminen handelt ea sich um ein Piamin oder ein höheres Arain»
beispielsweiße um ein Diarain aus der Verbindungsreihe, welche mit 1,2-Diaminöraethan, 1,2-Dlaninopropan und 1,3-Dlaminopropan
beginnt, oder um ein Polyalkylenpolyamin, wie Polyäthylenpolyamin
und Polypropylenpolyaminc
Bei den die Alkyl- oder Alkenylgruppe tragenden Polyaminen kann
es sich auch um ein cyclisches Polyamin handeln, wie sie beispielsweise gebildet werden, wenn man aliphatisch^ Polyamine
mit durch Xthyleng:-"uppen ge tonnten Stickstoff atomen in Gegenwert von FiiXogenwaeserstoif, wie H(Il, erhitzte
909840/1521
Vorzugsweise liegt· ein Polyamin zugrunde, welches wenigstens
3 Stickstoffatome enthält, insbesondere ein entsprechendes Polyamin
aus der Reihe der Polyäthylenpolyamine oder ein Polyamin, welches daraus durch firhitzen in. Gegenwart von HCl erhalten
wird«
Beispiele für im Rahmen der Erfindung geeignete Alkenylpolyäthylenpolyamine
sind Polyisobutenyldiäthylentriamin, PoIyisobutenyltriäthylentetramin
und Polyisobutenyltetraäthylenpentamin, wobei die Polyisobutenylgruppen 80 bis 120 Kohlen-Stoffatome
enthalten.
Die erfindungsgemäösn Zusatzstoffe können, beispielsweise durch
Alkylieren aliphatischer Polyamine hergestellt werden. So kann
man ein Polyamin mit einem Alkyl- oder Alkenylhalogenid umsetzen. Bei der Bildung des alkylierten Polyamine wird gleichzeitig
der entsprechende Halogenwasserstoff freigesetzt, der z.B. in Form eines Salzes mit dem überschüssigen, als Ausgangsmaterial
eingesetzten Polyamin entfernt wird. Während dieser Umsetzung zwischen einem Alkyl- oder Alkenylhalogenid und den stark basischen
Polyaminen kann als Nebenreaktion eine Dehalogenierung
des Alkyl- oder Alkenylhalogenids eintreten, so daß als Nebenprodukte
Kohlenwasserstoffe gebildet werden. Die Entfernung dieser Kohlenwasserstoffe aus dem Sndprodukt ist aber nicht
unbedingt erforderlich.
Gemäß einer bevorzugten AusfUhrung3fom für die Herstellung der
neuen Zusatzstoffe geht raan von einem Alken mit einer endstän
909840/1521 BAD ORIGINAL
digen Doppelbindung aus, dessen Kohlenetoff atom in beta-Stellung
eine Methylgruppe trägt· Bei der Chlorierung mit der theoretisch
benötigten Menge an Chlor bildet sich ein alpha-Polyieobutylallylchlorid
und beta-PolyißObutylmethallylchlorid, während
gleichzeitig HCl abgespalten wird· Außerdem entsteht infolge von Nebenreaktionen eine gewisse Menge der entsprechenden Di~
Chlorverbindung. Mit dem so erhaltenen Chlorierungsprodukt wird
dann das Polyamin zu dem entsprechenden Alkenylpolyamin umge~
setztο Als Ausgangsmaterial dient beispielsweise Polyisobutylen,
welohes in einem inerten Lösungsmittel bei Zimmertemperatur mit der theoretischen Menge an Chlor behandelt wird, worauf das entstehende
Polyisobutenylchlorid mit Tetraäthylenpentamin au Poly*··
iBobutenyltetrafithylenpentaiain bzw, zu Dipolyisobutenyltetraäthylenpentamin
umgesetzt wird.
Die erfindungsgemäßen Sohmlerölzusatzatoffe stellen ausgezeichnete
Dispergierungsmittel dar und sie verleihen den Schmier-v*
ölen, denen sie einverleibt werden, sehr befriedigende Eigenschaften. Als Sohmierölbasis können Mineralschmieröle der verschiedensten
Viskositätsgrade sowie synthetische Schmieröle oder ein mit einem fetten öl verschnittenes Schmieröl, eingesetzt
werden. Der Zusatzstoff kann dem Schmieröl als solcher
oder in Form eines Konzentrates beigemischt werden, welches man beispielsweise erhält, indem nan den Zusatzstoff mit einer kleinen
Menge öl vermischt. Die Konzentration des Zusatzstoffes in dem öl kann innerhalb eines weiten Bereiches variieren· Im allgemeinen
wird die gewünschte reinigende Wirkung bereite eraitlt,
wenn man dem Schmieröl den Zusatzstoff in Mengen «wischen 0,1
909840/ 1 521
* » Λ β
und 10 Gew.«=# zuraischt, doch kann es in besonderen Fällen auch
erforderlich sein» größere föenge als die vorstehend erwähnten Konzentrationen anzuwenden, beispielsweise wenn daa Sohmieröl
in Dieselmotoren eingesetzt werden soll» welohe zu einer starken Verschmutzung neigen,,
Die erfindungsgemäßen Zusatzstoffe können auch in Kombination
mit anderen bekannten Zusatzstoffen angewendet werden» z.B. mit Antioxydationsmitteln, Reinigungsmitteln» Verbesserungsmitteln
für den Viskositätsindex, Antikorrosionsmittel^ Antisohaummitteln,
Mitteln aur Verbesserung der Schmierwirkung und mit Substanzen, wie sie üblicherweise Schmierölen zugesetzt
werden«
Die Erfindung wird durch das nachstehende Beispiel näher erläutert?
Herstellung von Polyisobutenyltetraäthylenpentamin:
a) Ein Polyisobutylen mit einem Molgewicht von 1 250 wurde in einer Konzentration von 40 Gew.~# in Tetrachlorkohlenstoff aufgelöst.
Haoh dem Zusatz eines Jodkristalls wurde Chlor bei Zimmertemperatur
so lange in die Lösung eingeleitet, bis die Farbe derselben verblaQte. Anschließend wurde das Lösungsmittel im
Vakuum verdampft, wobei gleichseitig das gebildete gasförmige
HOl entfernt wurde* 33er verbleibende Rückstand enthielt nooh
4,2 Gew.-# Chlor,
903040/1621 BAD original
( t
r t ' r
et et
1») Sas eo erhaltene Polyiaobutenylohlorid wurde 6 Stunden, lang
unter Rühren mit der vierfachen Menge Te-traäthylenpentomin auf
180° erhitzt. Neon dem Abkühlen wurde das Reaktioneprodukt in
Pentan aufgenommen und bis ssur Chlorfreiheit mit Wasser gewaschen·
Anschließend wurde das Lösungsmittel abgedampft· Der verbleibende Rückstand enthielt 2,5 Gew.-?C Stickstoff und
0,23 ötw,-# Chlorο
Diener Zusatzstoff vurde in einem Einzylinder Gardner-Die selfactor
und In einem Einzylinder Petter-Benzinmotor geprüft. Der
Zusatzstoff lag in der fertigen Sohmieröllösung in einer Konsentration
von 1,5 Gew.-S^ vor. Als Schiaierölbasie wurde ein
Lösungsmittel-raffiniertes, paraffin!sehef Schraieröldestillat
verwendet. Die Viskosität defl BasisölB betrug bei dem Petter-Teet
7,2 öS (98,9°) und bei dsia Gardner-Test 11,5 öS (98,9°)·
Wassergekühlter, Einzylinder Viertaktmotor? Zylinderbohrung:
108 mm; Hubhöhe: 152,4· mm; Hubvolumen: 1,4 1; Leistung ι 11 PS
bei 1200 Umdrehungen pro Minute; Testdauer* 17 Stunden; Treibstoff: ein Gasöl mit einem Schwefelgehalt von 0,9 Gew·-^; Temperatur
des Kühlwassers: 80°-
Bei dieBern Motorversuch wurde die Kolbenverschmutzung bewertet·
Wassergekühlter, EinaylincLer Viertaktmotor; Zylinderbohrungί
85 mm; Hubhöhe: 82,5 mm; Hubvolumen: 468 al; Kompressionsver-
9 0 9 8 k 0 / 1 5 2 1 bad original
hältnis: 10,0:1; Leistung: 3,5 PS boi 1500 Umdrehungen pro Minute;
Testdauer: 48 Stunden; als Treibstoff vrarde ein Motorbenzin
mit einen Zusatz von 0,32 ml TEL pro Liter (61,4-8 Gew.-fS Bleitetraäthyl, 18,81 Gew.-# Dichloröthan, 17,86 Gew.-^ Dibromäthan,
restliohe Bestandteile: farbstoff und Kerosin) sowie einem Sohwefelgehalt
von 0,05 Gew.-■■$>
verwendet. Die Temperatur dee Kühlwassers für den Zylinder betrug 80°, desjenigen für die Kühlung des
Steuerungsdeokels 24°<>
Bei diesem Test wurden die Kolbenver-· schmutzung und die Sohlaiainbildung bewertet»
Die Ergebnisse der beiden Kotorenprüfungen sind in der nachstehenden
Tabelle zusammengefaßt, in die zum Vergleich auch Versuch· mit dem Basisschmieröl ohne Zusatzstoff aufgenommen worden
sind.
Gardner-Dieselmotor, Kolbenreinheit (10 β rein)
Petter-Benzinmotor Schlamm« Kolbenbildung
reinheit (10 m rein)
Baaisöl +
1,5 Gew.-f/
Additiv
1,5 Gew.-f/
Additiv
Basisöl
9,3
4,4
8,8
5,9
7,5 5,1,
90984Ö/1521
BAD
Claims (5)
1) Alkyl- oder alkenylsubstituiertee allphatieohee Polyamin,
dadurch gekennzeichnet, daß es mindesten» eine Alkyl- oder
Alkenylgruppe mit mindesten· 50 Kohlenstoffatomen an ein
Stickstoffatom gebunden enthält·
2) Polyamln nach Anspruoh 1, dadurch gekennzeichnett dal t» eine
Alkyl- oder Alkenylgruppe alt 60 bis 150 Kohlenstoffatomen
enthält.
3} Polyamin naoh Anspruoh Z, dadurch gekanneelchnet, das es eine
Alkyl- oder eine Alkenylgruppe alt 80 bit 120 Kohlenetoffatomen
enthält·
4) Polyamin nach Anspruch 1-3» dadttroh gekennzeichnet, däü e·
3 oder mehr Sticketoffatone enthält«
5) Polyamin naoh Anspruch 1-4» dadurch fekenxuMlohnet, dai es
sloh um ein PolyieobutenylpolyAthylenpolyamin handelt.
BAD ORIGINAL
90dB40/U21
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NL296139 | 1963-08-02 |
Publications (3)
Publication Number | Publication Date |
---|---|
DE1520879A1 true DE1520879A1 (de) | 1969-10-02 |
DE1520879B2 DE1520879B2 (de) | 1978-08-03 |
DE1520879C3 DE1520879C3 (de) | 1979-04-05 |
Family
ID=19754926
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE1520879A Expired DE1520879C3 (de) | 1963-08-02 | 1964-07-31 | Verfahren zur Herstellung von alkyl- oder alkenylsubstituierten aliphatischen mehrwertigen Aminen |
Country Status (5)
Country | Link |
---|---|
US (1) | US3275554A (de) |
BE (1) | BE747590Q (de) |
DE (1) | DE1520879C3 (de) |
GB (1) | GB1004411A (de) |
NL (2) | NL137371C (de) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2040270A1 (de) * | 1970-04-23 | 1971-11-04 | Chevron Res | Verfahren zur Herstellung Polyolefin-substituierter Amine |
Families Citing this family (451)
Publication number | Priority date | Publication date | Assignee | Title |
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Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2267205A (en) * | 1938-08-04 | 1941-12-23 | Monsanto Chemicals | Detergent |
DE1049522B (de) * | 1956-05-04 | 1959-07-02 | Godfrey L. Cabot, Inc., Boston, Mass. (V. St. A.) | Wasserbeständiges Hochtemperaturschmierfett |
US3008993A (en) * | 1957-02-14 | 1961-11-14 | Monsanto Chemicals | Alkenyl polyamines |
NL262417A (de) * | 1960-03-15 |
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0
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- NL NL137371D patent/NL137371C/xx active
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1964
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- 1964-07-31 DE DE1520879A patent/DE1520879C3/de not_active Expired
- 1964-08-04 GB GB31384/64A patent/GB1004411A/en not_active Expired
-
1970
- 1970-03-19 BE BE747590A patent/BE747590Q/xx not_active IP Right Cessation
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2040270A1 (de) * | 1970-04-23 | 1971-11-04 | Chevron Res | Verfahren zur Herstellung Polyolefin-substituierter Amine |
Also Published As
Publication number | Publication date |
---|---|
NL296139A (de) | |
NL137371C (de) | |
DE1520879B2 (de) | 1978-08-03 |
US3275554A (en) | 1966-09-27 |
BE747590Q (fr) | 1970-08-31 |
GB1004411A (en) | 1965-09-15 |
DE1520879C3 (de) | 1979-04-05 |
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