EP0400874B1 - Multifunktionale viskositätsindexmodifizierende Additive, hergestellt aus Amidoaminen - Google Patents

Multifunktionale viskositätsindexmodifizierende Additive, hergestellt aus Amidoaminen Download PDF

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Publication number
EP0400874B1
EP0400874B1 EP90305579A EP90305579A EP0400874B1 EP 0400874 B1 EP0400874 B1 EP 0400874B1 EP 90305579 A EP90305579 A EP 90305579A EP 90305579 A EP90305579 A EP 90305579A EP 0400874 B1 EP0400874 B1 EP 0400874B1
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EP
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Prior art keywords
composition according
acid
amine
ethylene
anhydride
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Expired - Lifetime
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EP90305579A
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English (en)
French (fr)
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EP0400874A1 (de
Inventor
Antonio Gutierrez
Robert Dean Lundberg
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ExxonMobil Chemical Patents Inc
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Exxon Chemical Patents Inc
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    • C10M149/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M149/06—Macromolecular 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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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/083—Dibenzyl sulfide
    • 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/085—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing carboxyl groups; Derivatives thereof
    • 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
    • C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium 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
    • C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2221/02—Macromolecular compounds obtained by reactions of monomers involving only 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
    • C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2221/04—Macromolecular compounds 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
    • C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2221/04—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2221/041—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds involving sulfurisation of macromolecular compounds, e.g. polyolefins
    • 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
    • C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2221/04—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2221/043—Polyoxyalkylene ethers with a thioether 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
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • 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

Definitions

  • U.S. Pat. No. 3,316,177 teaches ethylene-propylene-diene, which are heated to elevated temperatures in the presence of oxygen so as to oxidize the polymer and cause its reaction with maleic anhydride which is present during the oxidation. The resulting polymer can then be reacted with alkylene polyamines.
  • a number of prior disclosures teach avoiding the use of polyamine having two primary amine groups to thereby reduce cross-linking problems which become more of a problem as the number of amine moieties added to the polymer molecule is increased in order to increase dispersancy.
  • U.S. Pat. No. 4,132,661 grafts ethylene copolymer, using peroxide and/or air blowing, with maleic anhydride and then reacts with a primary-tertiary diamine.
  • U.S. Pat. No. 4,219,432 teaches maleic anhydride grafted ethylene copolymer reacted with a mixture of an amine having only one primary group together with a second amine having two or more primary groups.
  • U.S. Patent No. 4,517,104 discloses polymeric viscosity index (V.I.) improver-dispersant additive for petroleum oils, particularly lubricating oils, comprising a copolymer of ethylene with one or more C3 to C28 alpha-olefins, preferably propylene, which has been grafted with acid moieties such as maleic anhydride using a free radical initiator in a solvent such as lubricating oil, and then reacted with a carboxylic acid component including hydrocarbyl substituted succinic anhydride or acid having 12-400 carbon atoms in said hydrocarbyl group or long chain monocarboxylic acid, and a polyamine having two or more primary amine groups.
  • V.I. polymeric viscosity index
  • the grafted polymer may be reacted with said acid component prereacted with said polyamine to form salts, amides, imides, etc. and then reacted with said grafted olefin polymer. These reactions can permit the incorporation of varnish inhibition and dispersancy into the ethylene copolymer while inhibiting cross-linking or gelling.
  • U.S. Patent 3,417,140 relates to the preparation of amido-amine compositions, which are useful as epoxy resin curing agents, by reacting a polyalkylene polyamine and a fatty amine (comprising a mono- or diamine having as one of the substituents on a nitrogen atom a hydrocarbyl radical having 8 to 24 carbon atoms) with an alpha-beta unsaturated carbonylic compound. It is disclosed that this reaction occurs through the Michael addition of an amine group across the unsaturated group of the carbonylic compound and through the condensation of an amine group with the carbonylic group.
  • U.S. Patent 3,445,441 relates to amino-amido polymers characterized by being a reaction product of at least a polyamine and an acrylate type compound, such as methyl or ethyl acrylate, and methyl or ethyl methacrylate.
  • the patent states that the polymers are useful in a wide variety of applications, such as floculating agents, water clarifying additives, corrosion inhibitors in oil and gas wells, and as lube oil additives.
  • U.S. Patent 3,903,003 relates to lubricating compositions containing an amido-amine reaction product of a terminally carboxylated isoprene polymer which is formed by reacting a terminally carboxylated substantially completely hydrogenated polyisoprene having an average molecular weight between about 20,000 and 250,000 and a nitrogen compound of the group consisting of polyalkylene amines and hydroxyl polyalkylene amines.
  • Oil soluble ethylene copolymers used in the invention are those capable of modifying or improving the viscosity index of oleaginous compositions, particularly lubricating oil compositions, i.e., polymers useful as V.I. improvers. Therefor, they have a number-average molecular weight ( M n ) of at least 15,000. These copolymers preferably have number average molecular weights of from 15,000 to 500,000, more preferably 20,000 to 300,000, and most preferably from 30,000 to 150,000. These V.I. improvers will generally have a narrow range of molecular weight, as determined by the ratio of weight-molecular weight ( M w ) to number-average molecular weight ( M n ).
  • Polymers having a M w / M n of less than 10, preferably less than 7, and more preferably 4 or less are most desirable.
  • ( M n ) and ( M w / M n ) are measured by the well known techniques of vapor phase osmometry (VPO), membrane osmometry and gel permeation chromatography.
  • VPO vapor phase osmometry
  • polymers having a narrow range of molecular weight may be obtained by a choice of synthesis conditions such as choice of principal catalyst and cocatalyst combination, addition of hydrogen during the synthesis, etc.
  • Post synthesis treatment such as extrusion at elevated temperature and under high shear through small orifices, mastication under elevated temperatures, thermal degradation, fractional precipitation from solution, etc. may also be used to obtain narrow ranges of desired molecular weights and to break down higher molecular weight polymer to different molecular weight grades for V.I. use.
  • These polymers are prepared from ethylene and ethylenically unsaturated hydrocarbons including cyclic, alicyclic and acyclic, containing from 3 to 28 carbons, e.g. 2 to 18 carbons.
  • These ethylene copolymers may contain from 15 to 90 wt. % ethylene, preferably 30 to 80 wt. % of ethylene and 10 to 85 wt. %, preferably 20 to 70 wt. % of one or more C3 to C28, preferably C3 to C18 more preferably C3 to C8, unsaturated hydrocarbons, preferably alpha olefins. While not essential, such copolymers preferably have a degree of crystallinity of less than 25 wt.
  • terpolymer tetrapolymer, etc.
  • 1-pentene, 1-hexene, 1-heptene, 1-octene, 1-nonene, 1-decene, etc. also branched chain alpha-olefins, such as 4-methyl-1-pentene, 4-methyl-1-hexene, 5-methylpentene-1, 4,4-dimethyl-1-pentene, and 6-methylheptene-1, etc., and mixtures thereof.
  • Preferred carboxylic acid materials are the dicarboxylic acid anhydrides. Maleic anhydride or a derivative thereof is particularly preferred as it does not appear to homopolymerize appreciably but grafts onto the ethylene copolymer to give two carboxylic acid functionalities. Such preferred materials have the generic formula wherein R' and R'' are independently hydrogen or a halogen.
  • the about C50-C400 hydrocarbyl subtituted dicarboxylic acid or anhydride includes the reaction product of the C50-C400 hydrocarbon polymer, generally a polyolefin, with (i) monounsaturated C4 to C10 dicarboxylic acid wherein (a) the carboxyl groups are vicinyl, i.e., located on adjacent carbon atoms, and (b) at least one, preferably both, of said adjacent carbon atoms are part of said monounsaturation; or with (ii) derivatives of (i) such as anhydrides of (i).
  • the monounsaturation of the dicarboxylic acid, anhydride, etc. becomes saturated.
  • maleic anhydride becomes a hydrocarbyl substituted succinic anhydride.
  • oil soluble viscosity modifying polymers will generally have number average molecular weights of from 103 to 106, preferably 104 to 106, e.g., 20,000 to 250,000, as determined by gel permeation chromatography or osmometry.
  • N-vinyl lactams are also suitable, e.g. N-vinyl pyrrolidones or N-vinyl piperidones.
  • Hydroxyamines which can be reacted with the polymer-substituted monocarboxylic acid materials to form dispersants include 2-amino-1-butanol, 2-amino-2-methyl-1-propanol, p-(beta-hydroxyethyl)-aniline, 2-amino-1-propanol, 3-amino-1-propanol, 2-amino-2-methyl-1, 3-propane-diol, 2-amino-2-ethyl-1, 3-propanediol, N-(beta-hydroxy-propyl)-N'-(beta-aminoethyl)-piperazine, tris(hydroxymethyl) amino-methane (also known as trismethylolaminomethane), 2-amino-1-butanol, ethanolamine, beta-(beta-hydroxyethoxy)ethylamine, and the like.
  • nucleophilic reactants suitable for reaction with the polymer-substituted monocarboxylic acid materials includes amines, alcohols, and compounds of mixed amine and hydroxy containing reactive functional groups, i.e., amino-alcohols.
  • THAM tris(hydroxymethyl) amino methane
  • Examples of same thus include C10 to C18 fatty acids, such as stearic or palmitic acid, but unsaturated acids such as oleic or branched carboxylic acids such as napthenic acids of molecular weights of from about 200 to 500, or synthetic carboxylic acids, are preferred, because of the improved handling and solubility properties of the resulting copper carboxylates.
  • oil-soluble copper dithiocarbamates of the general formula (RR,NCSS)nCu (where n is 1 or 2 and R and R, are the same or different hydrocarbyl radicals containing from 1 to 18, and preferably 2 to 12, carbon atoms, and including radicals such as alkyl, alkenyl, aryl, aralkyl, alkaryl and cycloaliphatic radicals. Particularly preferred as R and R, groups are alkyl groups of from 2 to 8 carbon atoms.
  • the radicals may, for example, be ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, amyl, n-hexyl, i-hexyl, n-heptyl, n-octyl, decyl, dodecyl, octadecyl, 2-ethylhexyl, phenyl, butylphenyl, cyclohexyl, methylcyclopentyl, propenyl, butenyl, etc.
  • the total number of carbon atoms i.e., R and R, will generally be about 5 or greater. Copper sulphonates, phenates, and acetylacetonates may also be used.
  • Detergents and metal rust inhibitors include the metal salts of sulphonic acids, alkyl phenols, sulfurized alkyl phenols, alkyl salicylates, naphthenates and other oil soluble mono- and di-carboxylic acids.
  • Highly basic (viz, overbased) metal salts such as highly basic alkaline earth metal sulfonates (especially Ca and Mg salts) are frequently used as detergents. Representative examples of such materials, and their methods of preparation, are found in EP-A-0208560.
  • the final formulations may employ typically about 10 wt. % of the additive-package with the remainder being base oil.
  • 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.
  • Into a reactor vessel are charged 200 grams of a 20 wt. % oil solution of succinic-anhydride grafted ethylene-propylene copolymer (containing about 43 wt.% ethylene and 57% wt.% propylene, the ethylene-propylene backbone having a M n of about 80,000, and having a thickening efficiency of about 1.2), 21.3 grams of polyisobutenyl succinic anhydride (having a succinic anhydride to polyisobutenyl mole ratio of 1.04, a polyisobutylene M n of about 960, ASTM Saponification Number of 112, and 90 wt.% active ingredient, i.e., polyisobutenyl succinic anhydride, the remainder being primarily unreacted polyisobutylene), and 130 grams of S130N mineral oil.
  • succinic-anhydride grafted ethylene-propylene copolymer containing about 43 wt.%
  • Example 5 The procedure of Example 5 is repeated except that the 4.12 grams of the amido-amine prepared in accordance with the procedure of Example 1 are replaced with 11.0 grams of amido-amine prepared in accordance with the procedure of Example 3.

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  • Chemical & Material Sciences (AREA)
  • 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)
  • Compositions Of Macromolecular Compounds (AREA)

Claims (41)

  1. Öllösliche Zusammensetzung, die als multifunktionelles Viskositätsverbesserer-Additiv für ölige Zusammensetzungen brauchbar ist und die das Addukt von
    (A) mit hochmolekulargewichtigem Ethylencopolymer substituiertem Carbonsäurematerial, das das Reaktionsprodukt von (i) Ethylencopolymer mit einem durchschnittlichen Molekulargewicht (Zahlenmittel) von mindestens 15 000 und (ii) einfach ungesättigtem Carbonsäurematerial umfaßt, und
    (B) Amid-Amin oder Thioamid-Amin, das das Reaktionsprodukt von (i) Polyamin und (ii) α,ß-ungesättigter Verbindung mit der Formel
    Figure imgb0029
     umfaßt, wobei X Sauerstoff oder Schwefel ist, Y -OR⁴, -SR⁴ oder
    Figure imgb0030
     ist, und R¹, R², R³, R⁴ und R⁵ unabhängig ausgewählt sind aus Wasserstoff, Kohlenwasserstoff und substituiertem Kohlenwasserstoff, umfaßt.
  2. Zusammensetzung nach Anspruch 1, bei der das Ethylencopolymer (A)(i) ein Copolymer aus Ethylen und mindestens einem C₃ bis C₂₈-α-Olefin umfaßt.
  3. Zusammensetzung nach Anspruch 2, bei der das C₃ bis C₂₈-α-Olefin Propylen ist.
  4. Zusammensetzung nach einem der Ansprüche 1 bis 3, bei der das einfach ungesättigte Carbonsäurematerial (A)(ii) ausgewählt ist aus der Gruppe bestehend aus einfach ungesättigtem C₄ bis C₁₀-Dicarbonsäurematerial, einfach ungesättigtem C₃ bis C₁₀-Monocarbonsäurematerial und Mischungen hiervon.
  5. Zusammensetzung nach Anspruch 4, bei der (A)(ii) ausgewählt ist aus Maleinsäureanhydrid, Maleinsäure und Mischungen hiervon.
  6. Zusammensetzung nach Anspruch 4, bei der (A)(i) ausgewählt ist aus Acrylsäure, Acrylsäureester, Methacrylsäure, Methacrylsäureester und Mischungen hiervon.
  7. Zusammensetzung nach Anspruch 1, bei der das mit hochmolekulargewichtigem Ethylencopolymer substituierte Carbonsäurematerial mindestens eines aus mit Bernsteinsäureanhydrid substituiertem Ethylen-Propylen-Copolymer und mit Bernsteinsäure substituiertem Ethylen-Propylen-Copolymer umfaßt.
  8. Zusammensetzung nach Anspruch 1, bei der das mit hochmolekulargewichtigem Ethylencopolymer substituierte Carbonsäurematerial mit Propionsäure substituiertes Ethylen-Propylen-Copolymer umfaßt.
  9. Zusammensetzung nach einem der Ansprüche 1 bis 8, bei der das Polyamin (B)(i) Polyamine umfaßt, die 2 bis 60 Kohlenstoffatome und 2 bis 12 Stickstoffatome pro Molekül enthalten.
  10. Zusammensetzung nach Anspruch 9, bei der das Polyamin (B)(i) Alkylenpolyamin oder Polyalkylenpolyamin umfaßt, wobei jede Alkylengruppe 2 bis 6 Kohlenstoffatome enthält und das Alkylenpolyamin oder Polyalkylenpolyamin 2 bis 5 Stickstoffatome pro Molekül enthält.
  11. Zusammensetzung nach Anspruch 10, bei der das Polyamin (B)(i) Ethylenpolyamin, Propylenpolyamin, Polyethylenpolyamin oder Polypropylenpolyamin umfaßt.
  12. Zusammensetzung nach einem der Ansprüche 1 bis 11, bei der das Polyamin (B)(i) im Durchschnitt mindestens zwei primäre Aminogruppen pro Molekül enthält.
  13. Zusammensetzung nach einem der Ansprüche 1 bis 12, bei der (B)(ii) mindestens eines aus Methylacrylat, Ethylacrylat, Propylacrylat, Butylacrylat, Methylmethacrylat, Ethylmethacrylat, Propylmethacrylat und Butylmethacrylat umfaßt.
  14. Zusammensetzung nach Anspruch 12 und 13, wobei das Polyamin (B)(i) 2 bis 60 Kohlenstoffatome und 2 bis 12 Stickstoffatome enthält und die α,ß-ungesättigte Verbindung (B)(ii) C₁ bis C₄-Alkylester von Acryl- oder Methacrylsäure umfaßt.
  15. Zusammensetzung nach einem der Ansprüche 1 bis 14, bei der 3 bis 5 Äquivalente von dem Polyamin, bezogen auf dessen Gehalt an primärem Amin, pro Mol der α,ß-ungesättigten Verbindung (B)(ii) umgesetzt werden.
  16. Zusammensetzung nach einem der Ansprüche 1 bis 15, bei der x von (B)I(ii) Sauerstoff ist und das Amid-Amin im Durchschnitt 1 bis 3 Amidgruppen pro Molekül enthält.
  17. Zusammensetzung nach einem der Ansprüche 1 bis 15, bei der x von (B)I(ii) Schwefel ist und das Thioamid-Amin im Durchschnitt 1 bis 3 Thioamidgruppen pro Molekül enthält.
  18. Zusammensetzung nach einem der Ansprüche 1 bis 9, bei der das Polyamin (II)(B)(i) Alkylenpolyamin oder Polyalkylenpolyamin umfaßt, wobei jede Alkylengruppe 2 bis 6 Kohlenstoffatome enthält und das Alkylenpolyamin oder Alkylenpolyamin 5 bis 9 Stickstoffatome pro Molekül enthält.
  19. Zusammensetzung nach einem der Ansprüche 1 bis 18, bei der das Addukt (A), (B) und (C) kohlenwasserstoffsubstituierte C₁₂-C₄₀₀-Dicarbonsäure oder -anhydrid oder kohlenwasserstoffsubstituierte C₅₀-C₄₀₀-Monocarbonsäure umfaßt.
  20. Zusammensetzung nach Anspruch 19, bei der (C) kohlenwasserstoffsubstituierte C₁₂-C₄₀₀-Bernsteinsäure oder -anhydrid ist.
  21. Zusammensetzung nach Anspruch 20, bei der Komponente (C) C₁₂-C₄₀₀-Polyisobutenylbernsteinsäureanhydrid ist.
  22. Zusammensetzung nach Anspruch 20, bei der Komponente (C) C₅₀-C₄₀₀-Polyisobutenylbernsteinsäureanhydrid ist.
  23. Ölige Zusammensetzung, die bessere viskosimetrische Eigenschaften und bessere Dispergiereigenschaften zeigt und die
    (I) öliges Material, und
    (II) als ein multifunktionelles, viskositätsverbesserndes und Dispersionsmitteladditiv eine Zusammensetzung nach einem der Ansprüche 1 bis 22 umfaßt.
  24. Zusammensetzung nach Anspruch 23, bei der (I) ein Schmieröl ist.
  25. Zusammensetzung nach Anspruch 23 in Form eines Ölkonzentrats, das 5 bis 49 Gew.% (II) enthält.
  26. Zusammensetzung nach Anspruch 23, bei der (I) eine fertig formulierte Schmierölzusammensetzung ist.
  27. Zusammensetzung nach Anspruch 26, die 0,01 bis 20 Gew.% (II) enthält.
  28. Zusammensetzung nach Anspruch 27, die 0,1 bis 10 Gew.% (II) enthält.
  29. Zusammensetzung nach Anspruch 27, die 0,2 bis 5 Gew.% (II) enthält.
  30. Verfahren zur Herstellung einer Zusammensetzung, die als multifunktionelles Viskositätsverbesserer-Öladditiv brauchbar ist, bei dem
    (A) mit hochmolekulargewichtigem Ethylencopolymer substituiertes Carbonsäurematerial, das das Reaktionsprodukt von (i) einem Ethylencopolymer mit einem durchschnittlichen Molekulargewicht (Zahlenmittel) von mindestens 15 000 und (ii) einfach ungesättigtem Carbonsäurematerial umfaßt, mit
    (B) einem Amid-Amin oder Thioamid-Amin, das mindestens eine primäre Aminogruppe enthält und das Reaktionsprodukt von
    (i) mindestens einem Polyamin und
    (ii) einer α,β-ungesättigten Verbindung mit der Formel
    Figure imgb0031
     umfaßt, wobei X Sauerstoff oder Schwefel ist, Y -OR⁴, -SR⁴ oder -NR⁴(R⁵)ist, und R¹, R², R³, R⁴ und R⁵ gleich oder verschieden sind und unabhängig ausgewählt sind aus Wasserstoff und substituierten oder nicht substituierten Kohlenwasserstoffresten, umgesetzt wird, wobei die Aminverbindung (B) in eine Lösung eingebracht wird, die das Polymersäurematerial (A) enthält, und mit diesem für eine Zeitdauer von 1 bis 10 Stunden auf eine Temperatur von 100°C bis 250°C erhitzt wird, so daß mindestens ein Teil der primären Aminogruppen der Aminverbindung (B) mit mindestens einem Teil der Carboxylgruppen des Polymersäurematerials (A) reagiert.
  31. Verfahren nach Anspruch 30, bei dem das Polymersäurematerial (A) mit der Aminverbindung (B) und einer Carbonsäureverbindung (C) oder mit dem vorab gebildeten Reaktionsprodukt von (B) und (C) umgesetzt wird.
  32. Verfahren nach Anspruch 31, bei dem die Komponente (C) eine kohlenwasserstoffsubstituierte C₁₂-C₄₀₀-Dicarbonsäure oder -anhydrid ist.
  33. Verfahren nach Anspruch 32, bei dem die Komponente (C) eine kohlenwasserstoffsubstituierte C₁₂-C₄₀₀-Bernsteinsäure oder -anhydrid ist.
  34. Verfahren nach Anspruch 33, bei dem die Komponente (C) eine C₁₂-C₄₀₀-Polyisobutenylbernsteinsäure oder -anhydrid ist.
  35. Verfahren nach einem der Ansprüche 30 bis 34, bei dem das Carbonsäurematerial (A)(ii) eine C₄-C₁₀-Dicarbonsäure oder -anhydrid ist.
  36. Verfahren nach Anspruch 35, bei dem die C₄-C₁₀-Säure oder -anhydrid Bernsteinsäureanhydrid ist.
  37. Verfahren nach einem der Ansprüche 30 bis 36, bei dem das Ethylencopolymer (A)(i) ein Ethylen-Propylen-Copolymer ist.
  38. Verfahren nach einem der Ansprüche 30 bis 34, bei dem das Carbonsäurematerial (A)(ii) eine C₃₋₁₀-Monocarbonsäure oder -anhydrid ist.
  39. Verfahren nach Anspruch 38, bei dem das Ethylencopolymer (A)(i) ein Ethylen-Propylen-Copolymer ist.
  40. Verfahren nach einem der Ansprüche 30 bis 39, bei dem das Polyamin (B)(i) ein Alkylenpolyamin oder Polyalkylenpolyamin mit 2 bis 5 Stickstoffatomen pro Molekül und 2 bis 6 Kohlenstoffatomen in jeder Alkylengruppe umfaßt.
  41. Verfahren nach Anspruch 40, bei dem X in Komponente (B)(ii) Sauerstoff ist.
EP90305579A 1989-05-30 1990-05-22 Multifunktionale viskositätsindexmodifizierende Additive, hergestellt aus Amidoaminen Expired - Lifetime EP0400874B1 (de)

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IT1258249B (it) * 1992-11-06 1996-02-22 Addittivo polimerico per olii lubrificanti
US5672573A (en) * 1996-04-10 1997-09-30 Exxon Chemical Patents Inc. Amicloamine derivatives of carboxylic and thiocarboxylic-functionalized hydrocarbon polymers
WO2021018467A1 (en) * 2019-07-29 2021-02-04 Clariant International Ltd Wax inhibitors with improved flowability
CN114875412B (zh) * 2022-05-19 2023-03-10 西安交通大学 一种多核无定型固体缓蚀剂的制备方法

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EP0400874A1 (de) 1990-12-05
DE69001389D1 (de) 1993-05-27
AU5599290A (en) 1990-12-06
CA2015063A1 (en) 1990-11-30
DE69001389T2 (de) 1993-08-19
BR9002543A (pt) 1991-08-13
AU623525B2 (en) 1992-05-14

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