EP0400870B1 - Multifunktionaler Viskositätsindexverbesserer, hergestellt aus Polyamin, welcher eine primäre und mindestens eine sekundäre Amino-Gruppe enthält und der verbesserte viskometrische Eigenschaften bei niedrigen Temperaturen aufweist - Google Patents

Multifunktionaler Viskositätsindexverbesserer, hergestellt aus Polyamin, welcher eine primäre und mindestens eine sekundäre Amino-Gruppe enthält und der verbesserte viskometrische Eigenschaften bei niedrigen Temperaturen aufweist Download PDF

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EP0400870B1
EP0400870B1 EP90305567A EP90305567A EP0400870B1 EP 0400870 B1 EP0400870 B1 EP 0400870B1 EP 90305567 A EP90305567 A EP 90305567A EP 90305567 A EP90305567 A EP 90305567A EP 0400870 B1 EP0400870 B1 EP 0400870B1
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copolymer
ethylene
composition according
grafted
weight
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EP0400870A1 (de
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Antonio Gutierrez
David Yen-Lung Chung
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ExxonMobil Chemical Patents Inc
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/22Organic compounds containing nitrogen
    • C10L1/234Macromolecular compounds
    • C10L1/236Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof
    • C10L1/2364Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof homo- or copolymers derived from unsaturated compounds containing amide and/or imide groups
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    • C10M149/00Lubricating compositions characterised by the additive being a macromolecular compound containing nitrogen
    • C10M149/02Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M149/06Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amido or imido group
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    • C10M151/00Lubricating compositions characterised by the additive being a macromolecular compound containing sulfur, selenium or tellurium
    • C10M151/02Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
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    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2205/00Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
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    • C10M2205/00Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M2205/00Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
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    • C10M2205/022Ethene
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    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
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    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2215/042Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
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    • C10M2215/26Amines
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    • C10M2217/00Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/02Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/024Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amido or imido group
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    • C10M2217/00Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/04Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/046Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
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    • C10M2217/00Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/06Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
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    • C10M2221/00Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2221/02Macromolecular compounds obtained by reactions of monomers involving only carbon-to-carbon unsaturated bonds
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    • C10M2221/00Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2221/04Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2221/043Polyoxyalkylene ethers with a thioether group
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    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2070/00Specific manufacturing methods for lubricant compositions
    • C10N2070/02Concentrating of additives

Definitions

  • French published application No. 2423530 grafts maleic anhydride on an ethylene-propylene copolymer with maleic anhydride at 150° to 210°C followed by reaction with an amine having one primary or secondary group.
  • the low crystallinity copolymer segments comprise from about 90 to 10 wt.%, preferably from about 80 to 15 wt.%, and more preferably from about 65 to 35 wt.%, of the total copolymer chain, and contain an average ethylene content of from about 20 to 53 wt.%, preferably from about 30 to 50 wt.%, and more preferably from about 35 to 50 wt.%.
  • the copolymers will contain at least one crystallizable segment rich in methylene units (hereinafter called an "M" segment) and at least one low crystallinity ethylene-alpha-olefin copolymer segment (hereinafter called a "T" segment).
  • the copolymers may be therefore illustrated by copolymers selected from the group consisting of copolymer chain structures having the following segment sequences: wherein M and T are defined above, M 1 and M 2 can be the same or different and are each M segments, T and T 2 can be the same or different and are each T segments, x is an integer of from 1 to 3 and y is an integer of 1 to 3.
  • the Intra-CD of copolymer in accordance with the present invention is such that at least two portions of an individual intramolecularly heterogeneous chain, each portion comprising at least 5 weight percent of the chain, differ in composition from one another by at least 7 weight percent ethylene. Unless otherwise indicated, this property of Intra-CD as referred to herein is based upon at least two 5 weight percent portions of copolymer chain.
  • the Intra-CD of copolymer in accordance with the present invention can be such that at least two portions of copolymer chain differ by at least 10 weight percent ethylene. Differences of at least 20 weight percent, as well as, of at least 40 weight percent ethylene are also considered to be in accordance with the present invention.
  • the molecular weight distribution is very narrow, as characterized by at least one of a ratio of M w /M n of less than 2 and a ratio of M z /M w of less than 1.8.
  • MWD molecular weight distribution
  • the preferred copolymers have MwfMn less than about 1.5, with less than about 1.25 being most preferred.
  • the preferred M z /M w is less than about 1.5, with less than about 1.2 being most preferred.
  • copolymers of the instant invention may be produced by polymerization of a reaction mixture comprised of catalyst, ethylene and at least one additional alpha-olefin monomer, wherein the amounts of monomer, and preferably ethylene, is varied during the course of the polymerization in a controlled manner as will be hereinafter described. Solution polymerizations are preferred.
  • the composition of the catalyst used to produce alpha-olefin copolymers has a profound effect on copolymer product properties such as compositional dispersity and MWD.
  • the catalyst utilized in practicing processes in accordance with the present invention should be such as to yield essentially one active catalyst species in the reaction mixture. More specifically, it should yield one primary active catalyst species which provides for substantially all of the polymerization reaction. Additional active catalyst species could provide as much as 35% (weight) of the total copolymer. Preferably, they should account for about 10% or less of the copolymer.
  • the essentially one active species should provide for at least 65% of the total copolymer produced, preferably for at least 90% thereof.
  • the extent to which a catalyst species contributes to the polymerization can be readily determined using the below-described techniques for characterizing catalyst according to the number of active catalyst species.
  • Polymerizations in accordance with the present invention should be conducted in such a manner and under conditions sufficient to initiate propagation of essentially all copolymer chains simultaneously. This can be accomplished by utilizing the process steps and conditions described below.
  • the Intra-CD of the copolymer is such that at least two portions of an individual intramolecularly heterogeneous chain, each portion comprising at least 5 weight percent of said chain, differ in composition from one another by at least 7 weight percent ethylene.
  • the Intra-CD can be such that at least two portions of copolymer chain differ by at least 10 weight percent ethylene. Differences of at least 20 weight percent, as well as, 40 weight percent ethylene are also considered to be in accordance with the present invention.
  • Such unsaturated mono- and dicarboxylic acids, or anhydrides and thereof include fumaric acid, itaconic acid, maleic acid, maleic anhydride, chloromaleic anhydride, acrylic acid, methacrylic acid, crotonic acid, cinnamic acid, methyl acrylate, ethyl acrylate, methyl methacrylate, etc.
  • the grafting conditions are those which are effective to yield a graft copolymer which contains an ethylene copolymer backbone having substantially the same or similar MWD distribution as the ethylene copolymer reactant.
  • substantially the same or similar MWD is meant a MWD which is about 10% or less different from the MWD of the ungrafted ethylene-alpha-olefin copolymer, i.e., the difference between the MWD of ungrafted ethylene-alpha-olefin copolymer and grafted ethylene-alpha-olefin copolymer is about 10% or less.
  • the resultant grafted copolymer contains the residue of the ethylene copolymer as the backbone and the residue of the ethylenically unsaturated grafting material as the grafted moiety.
  • residues is meant the respective moieties produced by and remaining after the grafting process or reaction.
  • the ethylenically unsaturated grafting material may be maleic anhydride
  • succinic anhydride moiety that is grafted or attached to the ethylene copolymer backbone.
  • this succinic anhydride moiety is referred to herein as the residue of the ethylenically unsaturated grafting material, i.e., residue of maleic anhydride.
  • polyamines contain from 2 to about 7 nitrogens, from 7 (8 if an oxygen or sulfur is present) to about 80 carbons, and optionally a sulfur or oxygen atom.
  • polyamines include polyamines represented by the formula wherein:
  • This reaction can be conducted in a polar or non-polar solvent, e.g., xylene, toluene, benzene, and the like, and is preferably conducted in the presence of a mineral or synthetic lubricating oil.
  • a polar or non-polar solvent e.g., xylene, toluene, benzene, and the like, and is preferably conducted in the presence of a mineral or synthetic lubricating oil.
  • carboxylic acid component and the polyamine may be prereacted, and this prereacted carboxylic acid component/polyamine may then be coreacted with the carboxylic acid material grafted ethylene copolymer to form the nitrogen containing carboxylic acid material grafted ethylene copolymer of the instant invention.
  • olefin polymer and the dicarboxylic acid or derivative may be simply heated together as disclosed in U.S. Patents 3,361,673 and 3,401,118 to cause a thermal "enen" reaction to take place.
  • the olefin polymer can be first halogenated, for example, chlorinated or brominated to about 1 to 8 wt. %, preferably 3 to 7 wt.
  • a minor amount, e.g. 0.01 up to 49 wt %, preferably 0.05 to 25 wt. %, based on the weight of the total composition, of the V.I. inprover-dispersants produced in accordance with this invention can be incorporated into a major amount of an oleaginous material, such as a lubricating oil or hydrocarbon fuel, depending upon whether one is forming finished products or additive concentrates.
  • an oleaginous material such as a lubricating oil or hydrocarbon fuel, depending upon whether one is forming finished products or additive concentrates.
  • derivatized copolymer concentrations are usually within the range of about 0.01 to 25 wt %, of the total composition.
  • compositions when containing these conventional additives are typically blended into the base oil in amounts which are effective to provide their normal attendant function.
  • Representative effective amounts of such additives are illustrated as follows:
  • weight percents expressed herein are based on active ingredient (a.i.) content of the additive, and/or upon the total weight of any additive-package, or formulation which will be the sum of the a.i. weight of each additive plus the weight of total oil or diluent.
  • the Mwand M n of the grafted copolymer are 101,000 M w and 87,000 M n .
  • the M w /M n of this grafted copolymer is 1.16, while the M z /M w is 1.137.

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  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Lubricants (AREA)

Claims (31)

1. Zusammensetzung, die das Reaktionsprodukt von
(i)
(a) einem Copolymer aus Ethylen und mindestens einem weiteren a-Olefinmonomer, wobei das Copolymer intramolekular heterogene Copolymerketten umfaßt, die mindestens ein kristallisierbares Segment aus Methyleneinheiten und mindestens ein Ethylen-a-Olefin-Copolymersegment mit niedriger Kristallinität enthalten, wobei das mindestens eine kristallisierbare Segment mindestens 10 Gew.% der Copolymerkette ausmacht und mindestens 57 Gew.% Ethylen enthält, wobei das Segment mit niedriger Kristallinität nicht mehr als 53 Gew.% Ethylen enthält und wobei das Copolymer eine Molekulargewichtsverteilung besitzt, die durch mindestens eines der Verhältnisse Mw/Mn von weniger als 2 und Mz/Mw von weniger als 1,8 gekennzeichnet ist, und wobei mindestens zwei Anteile einer individuellen, intramolekular heterogenen Kette, von denen jeder Anteil mindestens 5 Gew.% der Kette ausmacht, sich in der Zusammensetzung um mindestens 7 Gew.% Ethylen voneinander unterscheiden, wobei das Copolymer mit
(b) ethylenisch einfach ungesättigtem Carbonsäurematerial mit 1 bis 2 Carbonsäuregruppen oder einer Anhydridgruppe gepfropft ist, um gepfropftes Ethylencopolymer zu bilden, wobei die Molekulargewichtsverteilung des resultierenden gepfropften Copolymers innerhalb von 10 % oder weniger der Molekulargewichtsverteilung des Ethylencopolymers (i)(a) ist, und
(ii) mindestens einem Polyamin umfaßt, das nur eine primäre Aminogruppe und mindestens eine sekundäre Aminogruppe enthält.
2. Zusammensetzung nach Anspruch 1, bei der das Copolymer (i)(a) eine solche intermolekulare Dispersität der Zusammensetzung aufweist, daß 95 Gew.% der Copolymerketten eine Zusammensetzung aufweisen, die sich um 15 Gew.% oder weniger von der durchschnittlichen Ethylenzusammensetzung unterscheidet.
3. Zusammensetzung nach Anspruch 2, bei der die intermolekulare Dispersität der Zusammensetzung des Copolymers (i)(a) eine solche ist, daß 95 Gew.% der Copolymerketten eine Zusammensetzung aufweisen, die sich um 13 Gew.% oder weniger von der durchschnittlichen Ethylenzusammensetzung unterscheidet.
4. Zusammensetzung nach Anspruch 3, bei der die intermolekulare Dispersität der Zusammensetzung des Copolymers (i)(a) eine solche ist, daß 95 Gew.% der Copolymerketten eine Zusammensetzung aufweisen, die sich um 10 Gew.% oder weniger von der durchschnittlichen Ethylenzusammensetzung unterscheidet.
5. Zusammensetzung nach einem der Ansprüche 1 bis 4, bei der das Segment mit niedriger Kristallinität von dem Copolymer (i)(a) 20 bis 53 Gew.% Ethylen umfaßt.
6. Zusammensetzung nach Anspruch 5, bei der das Segment mit niedriger Kristallinität von dem Copolymer (i)(a) 30 bis 50 Gew.% Ethylen umfaßt.
7. Zusammensetzung nach einem der Ansprüche 1 bis 6, bei der das kristallisierbare Segment mindestens 57 Gew.% Ethylen umfaßt.
8. Zusammensetzung nach einem der Ansprüche 1 bis 7, bei der das Copolymer (i)(a) einen minimalen Gesamtethylengehalt von 20 %, bezogen auf das Gewicht, besitzt.
9. Zusammensetzung nach einem derAnsprüche 1 bis 8, bei der das Copolymer(i)(a) durch ein durchschnittliches Molekulargewicht (Gewichtsmittel) von 20 000 bis 250 000 gekennzeichnet ist.
10. Zusammensetzung nach einem der Ansprüche 1 bis 9, bei der das Copolymer (i)(a) eine Molekulargewichtsverteilung aufweist, die durch mindestens eines der Verhältnisse Mw/Mn von weniger als 1,5 und Mz/Mw von weniger als 1,5 gekennzeichnet ist.
11. Zusammensetzung nach Anspruch 10, bei der das Copolymer (i)(a) eine Molekulargewichtsverteilung aufweist, die durch mindestens eines der verhältnisse Mw/Mn von weniger als 1,25 und Mz/Mw von weniger als 1,2 gekennzeichnet ist.
12. Zusammensetzung nach einem derAnsprüche 1 bis 11, bei der die Kettensegmentsequenzen des Copolymers (i)(a) durch mindestens eine der Strukturen
Figure imgb0056
Figure imgb0057
Figure imgb0058
gekennzeichnet sind, in denen x und y jeweils ganze Zahlen von 1 bis 3 sind, M das kristallisierbare Segment umfaßt, T das Segment mit niedriger Kristallinität umfaßt, M1 und M2 gleich oder verschieden sind und jeweils ein M-Segment umfassen, und T1 und T2 gleich oder verschieden sind und jeweils ein T-Segment umfassen.
13. Zusammensetzung nach Anspruch 12, bei der die Kettensegmentsequenzen des Copolymers (i)(a) durch Struktur 11 gekennzeichnet sind und x gleich 1 ist.
14. Zusammensetzung nach Anspruch 12 oder 13, bei der die Segmente T1 und T2 in dem Copolymer (i)(a) im wesentlichen das gleiche durchschnittliche Molekulargewicht (Gewichtsmittel) besitzen.
15. Zusammensetzung nach Anspruch 14, bei der in dem Copolymer (i)(a) die Summe der durchschnittlichen Molekulargewichte (Gewichtsmittel) der Segmente T1 und T2 im wesentlichen gleich dem durchschnittlichen Molekulargewicht (Gewichtsmittel) des M-Segments ist.
16. Zusammensetzung nach einem der Ansprüche 1 bis 15, bei der das einfach ungesättigte Carbonsäurematerial (i)(b) ausgewählt ist aus der Gruppe bestehend aus einfach ungesättigtem C4- bis C10-Dicarbonsäurematerial, einfach ungesättigtem C3- bis C10-Monocarbonsäurematerial und Mischungen daraus.
17. Zusammensetzung nach Anspruch 16, bei der das einfach ungesättigte C4- bis C10-Dicarbonsäurematerial ausgewählt ist aus der Gruppe bestehend aus Maleinsäureanhydrid, Maleinsäure und Mischungen daraus.
18. Zusammensetzung nach Anspruch 17, bei der das einfach ungesättigte C4- bis C10-Dicarbonsäurematerial Maleinsäureanhydrid ist.
19. Zusammensetzung nach einem der Ansprüche 1 bis 18, bei der das Polyamin 1 primäre Aminogruppe, 1 bis 6 sekundäre Aminogruppen und 7 bis 80 Kohlenstoffatome enthält.
20. Zusammensetzung nach einem der Ansprüche 1 bis 19, bei der das Polyamin außerdem ein Schwefel-oder Sauerstoffatom enthält.
21. Zusammensetzung nach einem der Ansprüche 1 bis 20, bei dem das Polyamin der Formel
Figure imgb0059
entspricht, in der
R1 ein zweiwertiger Kohlenwasserstoffrest mit 1 bis etwa 6 Kohlenstoffatomen ist,
R2 ein zweiwertiger Kohlenwasserstoffrest mit 1 bis etwa 6 Kohlenstoffatomen ist,
R3 ein Kohlenwasserstoffrest mit 1 bis etwa 40 Kohlenstoffatomen ist;
A Sauerstoff oder Schwefel ist:
y 0 oder 1 ist und
z einen Wert von 1 bis 6 besitzt.
22. Zusammensetzung nach Anspruch 21, bei der R1 und R2 Alkylen sind und R3 Alkyl ist.
23. Zusammensetzung nach Anspruch 22, bei der R1 und R2 unabhängig Alkylen mit 2 bis 4 Kohlenstoffatomen sind und R3 Alkyl mit 5 bis 30 Kohlenstoffatomen ist.
24. Materialzusammensetzung nach Anspruch 23, bei der R1 und R2 Propylen sind und R3 Alkyl mit 10 bis 20 Kohlenstoffatomen ist.
25. Zusammensetzung nach einem der Ansprüche 1 bis 24, die das Reaktionsprodukt von (i), (ii) und (iii) einer C50- bis C4oo-kohlenwasserstoffsubstituierten Carbonsäurekomponente mit 1 bis 2 Carbonsäuregruppen oder einer Anhydridgruppe umfaßt.
26. Zusammensetzung nach Anspruch 25, bei der die C50- bis C4oo-kohlenwasserstoffsubstituierte Carbonsäurekomponente (iii) C50- bis C4oo-kohlenwasserstoffsubstituierte C4- bis C10-Dicarbonsäure oder -anhydrid umfaßt.
27. Zusammensetzung nach Anspruch 26, bei der die C50- bis C4oo-kohlenwasserstoffsubstituierte Dicarbonsäure oder das entsprechende Anhydrid ausgewählt ist aus C50- bis C4oo-kohlenwasserstoffsubstituierter Bernsteinsäure, C50- bis C4oo-kohlenwasserstoffsubstituiertem Bernsteinsäureanhydrid oder Mischungen daraus.
28. Zusammensetzung nach Anspruch 27, bei der das C50- bis C4oo-kohlenwasserstoffsubstituierte Bernsteinsäureanhydrid polybutenylsubstituiertes Bernsteinsäureanhydrid umfaßt.
29. Ölige Zusammensetzung, die
(i) öliges Material und
(ii) eine Zusammensetzung gemäß einem der Ansprüche 1 bis 28 umfaßt.
30. Zusammensetzung nach Anspruch 29, bei der (i) Schmieröl ist.
31. Zusammensetzung nach Anspruch 29, die 0,001 bis 20 Gew.% (ii) enthält.
EP90305567A 1989-05-30 1990-05-22 Multifunktionaler Viskositätsindexverbesserer, hergestellt aus Polyamin, welcher eine primäre und mindestens eine sekundäre Amino-Gruppe enthält und der verbesserte viskometrische Eigenschaften bei niedrigen Temperaturen aufweist Expired - Lifetime EP0400870B1 (de)

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US4505834A (en) * 1980-10-27 1985-03-19 Edwin Cooper, Inc. Lubricating oil compositions containing graft copolymer as viscosity index improver-dispersant
US4517104A (en) * 1981-05-06 1985-05-14 Exxon Research & Engineering Co. Ethylene copolymer viscosity index improver-dispersant additive useful in oil compositions
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AU5598790A (en) 1990-12-06
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CA2015058A1 (en) 1990-11-30
BR9002547A (pt) 1991-08-13
AU628979B2 (en) 1992-09-24
DE69003171T2 (de) 1994-01-05
CA2015058C (en) 1999-05-04

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