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EP0400874B1 - Additifs à buts multiples pour la modification de l'indice de viscosité dérivés d'amidoamines - Google Patents

Additifs à buts multiples pour la modification de l'indice de viscosité dérivés d'amidoamines 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
European Patent Office
Prior art keywords
composition according
acid
amine
ethylene
anhydride
Prior art date
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Expired - Lifetime
Application number
EP90305579A
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German (de)
English (en)
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EP0400874A1 (fr
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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    • 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. Composition soluble dans l'huile, utile comme additif multifonctionnel améliorant l'indice de viscosité pour une composition oléagineuse, comprenant le produit d'addition :
    (A) d'une matière acide carboxylique substituée par un copolymère d'éthylène de haut poids moléculaire comprenant le produit de réaction (i) d'un copolymère d'éthylène ayant une moyenne numérique du poids moléculaire d'au moins 15 000 et (ii) d'une matière acide carboxylique à monoinsaturation ;
    (B) d'une amido-amine ou d'une thioamido-amine comprenant le produit de réaction (i) d'une polyamine et (ii) d'un composé à non-saturation alpha, bêta représenté par la formule :
    Figure imgb0032
     dans laquelle X est l'oxygène ou le soufre, Y est un groupe -OR⁴, -SR⁴ ou
    Figure imgb0033
     et R¹, R², R³, R⁴ et R⁵ sont choisis indépendamment entre l'hydrogène, un groupe hydrocarbyle et un groupe hydrocarbyle substitué.
  2. Composition suivant la revendication 1, dans laquelle le copolymère d'éthylène (A) (i) comprend un copolymère d'éthylène et d'au moins une alpha-oléfine en C₃ à C₂₈.
  3. Composition suivant la revendication 2, dans laquelle l'alpha-oléfine en C₃ à C₂₈ est le propylène.
  4. Composition suivant l'une quelconque des revendications 1 à 3, dans laquelle la matière acide carboxylique monoinsaturée (A)(ii) est choisie dans le groupe constitué d'une matière acide dicarboxylique monoinsaturée en C₄ à C₁₀, d'une matière acide monocarboxylique monoinsaturée en C₃ à C₁₀ et de mélanges de ces matières.
  5. Composition suivant la revendication 4, dans laquelle (A)(ii) est choisi entre l'anhydride maléique, l'acide maléique et des mélanges de ces composés.
  6. Composition suivant la revendication 4, dans laquelle (A)(ii) est choisi entre l'acide acrylique, un ester acrylique, l'acide méthacrylique, un ester méthacrylique et des mélanges de ces composés.
  7. Composition suivant la revendication 1, dans laquelle la matière acide carboxylique substituée par un copolymère d'éthylène de haut poids moléculaire comprend au moins une matière telle qu'un copolymère éthylène-propylène substitué avec l'anhydride succinique et un copolymère éthylène-propylène substitué avec l'acide succinique.
  8. Composition suivant la revendication 1, dans laquelle la matière acide carboxylique substituée par un copolymère d'éthylène de haut poids moléculaire comprend un copolymère éthylène-propylène substitué avec l'acide propionique.
  9. Composition suivant l'une quelconque des revendications 1 à 8, dans laquelle la polyamine (B)(i) comprend des polyamines contenant 2 à 60 atomes de carbone et 2 à 12 atomes d'azote par molécule.
  10. Composition suivant la revendication 9, dans laquelle la polyamine (B)(i) comprend une alkylènepolyamine ou une polyalkylènepolyamine dans laquelle chaque groupe alkylène contient 2 à 6 atomes de carbone et l'alkylènepolyamine ou la polyalkylènepolyamine contient 2 à 5 atomes d'azote par molécule.
  11. Composition suivant la revendication 10, dans laquelle la polyamine (B)(i) comprend l'éthylènepolyamine, la propylènepolyamine, une polyéthylènepolyamine ou une polypropylènepolyamine.
  12. Composition suivant l'une quelconque des revendications 1 à 11, dans laquelle la polyamine (B) (i) contient une moyenne d'au moins deux groupes amino primaires par molécule.
  13. Composition suivant l'une quelconque des revendications 1 à 12, dans laquelle (B)(ii) comprend au moins un composé tel que l'acrylate de méthyle, l'acrylate d'éthyle, l'acrylate de propyle, l'acrylate de butyle, le méthacrylate de méthyle, le méthacrylate d'éthyle, le méthacrylate de propyle et le méthacrylate de butyle.
  14. Composition suivant l'un des revendications 12 et 13, dans laquelle la polyamine (B)(i) contient 2 à 60 atomes de carbone et 2 à 12 atomes d'azote et le composé (B)(ii) à non-saturation alpha, bêta comprend des esters d'alkyle en C₁ à C₄ d'acide acrylique ou méthacrylique.
  15. Composition suivant l'une quelconque des revendications 1 à 14, dans laquelle on fait réagir une proportion de 3 à 5 équivalents de ladite polyamine, sur la base de sa teneur en amine primaire, par mole du composé (B)(ii) à non-saturation alpha, bêta.
  16. Composition suivant l'une quelconque des revendications 1 à 15, dans laquelle une proportion x de (B)I(ii) est de l'oxygène et l'amido-amine contient une moyenne de 1 à 3 groupes amido par molécule.
  17. Composition suivant l'une quelconque des revendications 1 à 15, dans laquelle une proportion X de (B) (ii) est du soufre et la thioamido-amine contient une moyenne de 1 à 3 groupes thioamido par molécule.
  18. Composition suivant l'une quelconque des revendications 1 à 9, dans laquelle la polyamine (II)(B)(i) comprend une alkylènepolyamine ou une polyalkylènepolyamine dans laquelle chaque groupe alkylène contient 2 à 6 atomes de carbone et l'alkylènepolyamine ou la polyalkylènepolyamine contient 5 à 9 atomes d'azote par molécule.
  19. Composition suivant l'une quelconque des revendications 1 à 18, dans laquelle le produit d'addition comprend (A), (B) et (C) un acide ou anhydride d'acide dicarboxylique à substituant hydrocarbyle en C₁₂ à C₄₀₀ ou un acide monocarboxylique à substituant hydrocarbyle en C₅₀ à C₄₀₀.
  20. Composition suivant la revendication 19, dans laquelle le composant (C) est un acide ou un anhydride d'acide succinique à substituant hydrocarbyle en C₁₂ a C₄₀₀.
  21. Composition suivant la revendication 20, dans laquelle le composant (C) est un anhydride succinique à substituant polyisobutényle en C₁₂ a C₄₀₀.
  22. Composition suivant la revendication 20, dans laquelle le composant (C) est un anhydride succinique à substituant polyisobutényle en C₅₀ a C₄₀₀.
  23. Composition oléagineuse douée de très bonnes propriétés viscosimétriques et d'un très bon pouvoir dispersant, comprenant :
    (I) une matière oléagineuse et
    (II) comme additif multifonctionnel améliorant la viscosité et dispersant, une composition suivant l'une quelconque des revendications 1 à 22.
  24. Composition suivant la revendication 23, dans laquelle (I) est une huile lubrifiante.
  25. Composition suivant la revendication 23, sous la forme d'un concentré dans l'huile contenant 5 à 49 % en poids de (II).
  26. Composition suivant la revendication 23, dans laquelle (I) est une composition d'huile lubrifiante entièrement formulée.
  27. Composition suivant la revendication 26, contenant 0,01 à 20 % en poids de (II).
  28. Composition suivant la revendication 27, contenant 0,1 à 10 % en poids de (II).
  29. Composition suivant la revendication 27, contenant 0,2 à 5 % en poids de (II).
  30. Procédé de production d'une composition utile comme additif multifonctionnel pour huile améliorant la viscosité, qui comprend la réaction :
    (A) d'une matière acide carboxylique substituée par un copolymère d'éthylène de haut poids moléculaire comprenant le produit de réaction (i) d'un copolymère d'éthylène ayant une moyenne numérique Mn du poids moléculaire d'au moins 15 000 et
       (ii) d'une matière acide carboxylique monoinsaturée ;
    (B) d'une amido-amine ou d'une thioamido-amine contenant au moins un groupe amino primaire, comprenant le produit de réaction
    (i) d'au moins une polyamine et
    (ii) d'un composé à non-saturation alpha, bêta de formule :
    Figure imgb0034
     dans laquelle X est le soufre ou l'oxygène, Y est un groupe -OR⁴, -SR⁴ ou -NR⁴(R⁵), et R¹, R², R³, R⁴ et R⁵ sont identiques ou différents et sont choisis indépendamment entre l'hydrogène et des radicaux hydrocarbyle substitués ou non substitués ; ladite amine (B) est introduite dans une solution contenant ladite matière acide polymérique (A) et chauffée avec elle à une température de 100°C à 250°C pendant une période de 1 à 10 heures, de manière qu'une portion au moins des groupes amino primaires de l'amine (B) réagisse avec au moins une portion des groupes carboxyle de la matière acide polymérique (A).
  31. Procédé suivant la revendication 30, dans lequel la matière acide polymérique (A) est amenée à réagir avec l'amine (B) et un composant acide carboxylique (C) ou avec le produit de réaction préformé de (B) et (C).
  32. Procédé suivant la revendication 31, dans lequel le composant (C) est un acide ou anhydride d'acide dicarboxylique à substituant hydrocarbyle en C₁₂ a C₄₀₀.
  33. Procédé suivant la revendication 32, dans lequel le composant (C) est un acide ou anhydride d'acide succinique à substituant hydrocarbyle en C₁₂ a C₄₀₀.
  34. Procédé suivant la revendication 33, dans lequel le composant (C) est un acide ou anhydride d'acide succinique à substituant polyisobutényle en C₁₂ a C₄₀₀.
  35. Procédé suivant l'une quelconque des revendications 30 à 34, dans lequel la matière acide carboxylique (A)(ii) est un acide ou anhydride d'acide dicarboxylique en C₄ à C₁₀.
  36. Procédé suivant la revendication 35, dans lequel l'acide ou anhydride d'acide en C₄ à C₁₀ est l'anhydride succinique.
  37. Procédé suivant l'une quelconque des revendications 30 à 36, dans lequel le copolymère d'éthylène (A)(i) est un copolymère éthylène-propylène.
  38. Procédé suivant l'une quelconque des revendications 30 à 34, dans lequel la matière acide carboxylique (A)(ii) est un acide ou anhydride d'acide monocarboxylique en C₃ à C₁₀.
  39. Procédé suivant la revendication 38, dans lequel le copolymère d'éthylène (A)(i) est un copolymère éthylène-propylène.
  40. Procédé suivant l'une quelconque des revendications 30 à 39, dans lequel la polyamine (B)(i) comprend une alkylènepolyamine ou une polyalkylènepolyamine ayant 2 à 5 atomes d'azote par molécule et 2 à 6 atomes de carbone dans chaque groupe alkylène.
  41. Procédé suivant la revendication 40, dans lequel X, dans le composant (B)(ii), est l'oxygène.
EP90305579A 1989-05-30 1990-05-22 Additifs à buts multiples pour la modification de l'indice de viscosité dérivés d'amidoamines Expired - Lifetime EP0400874B1 (fr)

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US35907089A 1989-05-30 1989-05-30
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EP0400874A1 EP0400874A1 (fr) 1990-12-05
EP0400874B1 true EP0400874B1 (fr) 1993-04-21

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EP (1) EP0400874B1 (fr)
AU (1) AU623525B2 (fr)
BR (1) BR9002543A (fr)
CA (1) CA2015063A1 (fr)
DE (1) DE69001389T2 (fr)

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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
ES2948723T3 (es) 2019-07-29 2023-09-18 Clariant Int Ltd Inhibidores de cera con fluidez mejorada
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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US2568876A (en) * 1949-11-14 1951-09-25 Socony Vacuum Oil Co Inc Reaction products of n-acylated polyalkylene-polyamines with alkenyl succinic acid anhydrides
US3445441A (en) * 1965-03-25 1969-05-20 Petrolite Corp Amino-amido polymers
US3448049A (en) * 1967-09-22 1969-06-03 Rohm & Haas Polyolefinic succinates
US3630902A (en) * 1969-07-23 1971-12-28 Chevron Res Lubricant additives derived from catalytically polymerized reaction products of succinimides and unsaturated monocarboxylic acids or anhydrides
US4240804A (en) * 1978-01-24 1980-12-23 Sherex Chemical Company, Inc. Alkyl acrylate adducts of polyamines, ether amines and ether polyamines
US4517104A (en) * 1981-05-06 1985-05-14 Exxon Research & Engineering Co. Ethylene copolymer viscosity index improver-dispersant additive useful in oil compositions
US4557847A (en) * 1983-11-21 1985-12-10 Exxon Research & Engineering Co. Ethylene copolymer viscosity index improver-dispersant additive useful in oil compositions
US4963275A (en) * 1986-10-07 1990-10-16 Exxon Chemical Patents Inc. Dispersant additives derived from lactone modified amido-amine adducts
US4857217A (en) * 1987-11-30 1989-08-15 Exxon Chemical Patents Inc. Dispersant additives derived from amido-amines

Also Published As

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

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