US3361673A - Lubricating oil compositions containing alkenyl succinimides of tetraethylene pentamine - Google Patents

Lubricating oil compositions containing alkenyl succinimides of tetraethylene pentamine Download PDF

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Publication number
US3361673A
US3361673A US835437A US83543759A US3361673A US 3361673 A US3361673 A US 3361673A US 835437 A US835437 A US 835437A US 83543759 A US83543759 A US 83543759A US 3361673 A US3361673 A US 3361673A
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United States
Prior art keywords
lubricating oil
oil compositions
tetraethylene pentamine
alkenyl
engine
Prior art date
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Expired - Lifetime
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US835437A
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English (en)
Inventor
Frank A Stuart
Robert G Anderson
Alan Y Drummond
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Chevron USA Inc
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Chevron Research and Technology Co
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Publication date
Priority to NL124842D priority Critical patent/NL124842C/xx
Application filed by Chevron Research and Technology Co filed Critical Chevron Research and Technology Co
Priority to US835411A priority patent/US3202678A/en
Priority to US835437A priority patent/US3361673A/en
Priority to DE19601444798 priority patent/DE1444798A1/de
Priority to GB27738/60A priority patent/GB956802A/en
Priority to FR835957A priority patent/FR1265086A/fr
Priority to NL6712905A priority patent/NL6712905A/xx
Application granted granted Critical
Publication of US3361673A publication Critical patent/US3361673A/en
Anticipated expiration legal-status Critical
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    • 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
    • C10M133/56—Amides; Imides
    • 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
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    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/02—Well-defined aliphatic compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/02—Well-defined aliphatic compounds
    • C10M2203/022—Well-defined aliphatic compounds saturated
    • C—CHEMISTRY; METALLURGY
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    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/02—Well-defined aliphatic compounds
    • C10M2203/024—Well-defined aliphatic compounds unsaturated
    • C—CHEMISTRY; METALLURGY
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    • C10M2203/04—Well-defined cycloaliphatic compounds
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    • C10M2203/06—Well-defined aromatic compounds
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    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
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    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/102—Aliphatic fractions
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    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/104—Aromatic fractions
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    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/106—Naphthenic fractions
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    • C10M2203/108—Residual fractions, e.g. bright stocks
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    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/024—Propene
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    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/026—Butene
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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    • C10M2207/28—Esters
    • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/105—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only
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    • C10M2209/109—Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified
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    • 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
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    • C10M2215/086—Imides
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    • 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/045—Siloxanes with specific structure containing silicon-to-hydroxyl 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/046—Siloxanes with specific structure containing silicon-oxygen-carbon 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/047—Siloxanes with specific structure containing alkylene oxide groups
    • 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/048—Siloxanes with specific structure containing carboxyl groups
    • 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
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/04—Groups 2 or 12
    • 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
    • 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
    • C10N2040/251—Alcohol-fuelled 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
    • C10N2040/255—Gasoline 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
    • C10N2040/255—Gasoline engines
    • C10N2040/28—Rotary 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
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Semi-solids; greasy

Definitions

  • This invention pertains to lubricating oil compositions having incorporated therein metal-free detergents. These particular metal-free detergents are N-substituted polyamine alkenyl succinimides.
  • Alkenyl succinic anhydrides and numerous derivatives thereof are well known in the art.
  • alkenyl succinic anhydrides in which the alkenyl radical contains from to 20 carbon atoms are taught as corrosion inhibitors in lubricating oil compositions.
  • products obtained by reacting such alkenyl succinic acid anhydrides with monoamines are taught as ferrous corrosion inhibitors for lubricating oil compositions.
  • the various detergents which are added to crankcase oils to reduce this formation of sludges and varnishes are metal organic compounds, particularly those compounds wherein the metal is linked to an or ganic group through an oxygen atom.
  • these metal-containing organic compounds have some etfectiveness as detergents for dispersing the precursors of deposits within the oil itself rather than permitting Patented Jan. 2, 1968 lubricating oil compositions which are compounded with a metal-free detergent.
  • lubricating oil compositions particularly useful for heavy duty service are obtained by incorporating N-substituted monoalkenyl succini-rnides derived from tetraethylene pentamine in oils of lubricating viscosity.
  • R is a hydrocarbon radical having a molecular Weight from about 400 to about 3000; that is, R is a hydrocarbon radical containing about 30 to about 200 carbon atoms.
  • alkenyl succinimides of tetraethylene pentamine can be prepared by reacting maleic anhydride with an olefinic hydrocarbon, followed by reacting the resulting alkenyl succinic anhydride with tetraethylene pentamine.
  • the R radical of the above formula that is, the alkenyl radical, is derived from an olefin containing from 2 to 5 carbon atoms.
  • the alkenyl radical is obtained by polymerizing an olefin containing from 2 to 5 carbon atoms to form a hydrocarbon having a molecular weight ranging from about 400 to about 3000, more preferably, 900 to 1200.
  • Such olefins are exemplified by ethylene, propylene, l-butene, Z-butene, isobutene, and mixtures thereof. Since the methods of polymerizing the olefins to form polymers thereof is immaterial in the formation of the new compound described herein, any of the numerous processes available can be used therefor.
  • N-substituted monoalkenyl succinimides derived from tetraethylene pentamine can be described generally by the following equations, using a polymer of isobutene as an example of the alkenyl radical: I 0
  • n has a value of about 7 to about 50.
  • the reaction set forth and described by Equation I hereinabove can proceed in a mol ratio of the polyolefin to the maleic anhydride of 1:1 to 1:10, preferably from 1:1 to 1:5.
  • the reaction temperature can vary from 300 F. to 450 F. Because of the greater yield of products obtained thereby, it is preferred to use the high range of temperatures (e.g., 375 F. to 450 F.).
  • the yield of the imide is extremely high even though the reactants are used in equal molar ratios. This is surprising, since under the conditions of the reaction there is an excess of secondary amino groups over primary amino groups, and any reaction with the secondary amino groups would lead to amide formation; thus, preventing imide formation.
  • Equation 11 The reaction described by Equation 11 hereinabove can be made at 220 F. to 500 F., preferably from 300 F. to 400 F.
  • the alkenyl succinic anhydride and the tetraethylene pentamine are reacted in about equal molar quantities.
  • the resulting alkenyl succinic anhydride may contain some unreacted polyolefin.
  • the resulting imide formed by reaction of the alkenyl succinic anhydride and the diamine will contain this polyolefin as an impurity which can be a diluent in the formation of lubricating oil compositions.
  • this unreacted polyolefin can be removed by precipitation, for example, by acetone or methanol from a hydrocarbon solution.
  • Lubricating oils which can be used as base oils include a wide variety of lubricating oils, such as naphthenic base, paraflin base, and mixed base lubricating oils, other hydrocarbon lubricants, e.-g., lubricating oils derived from coal products, and synthetic oils, e.g., alkylene polymers (such as polymers of propylene) butylene, etc., and the mixtures thereof), alkylene oxide-type polymers (e.g., propylene oxide polymers) and derivatives, including alkylene oxide polymers prepared by polymerizing the alkylene oxide in the presence of water or alcohols, e.g., ethyl alcohol, dicarboxylic acid esters (such as those which are prepared by esterifying such dicarboxylic acids as adipic acid, azelaic acid, suben'c acid, sebacic acid, salkanol succinic acid, fumaric acid, maleic acid, etc., with alohols such as buty
  • the above base oils may be used individually or in combinations thereof, wherever miscible or wherever made so by the use of mutual solvents.
  • the alkenyl succinimides of tetraalkylene pentamine can be used in oils of lubricating viscosity in amounts of 0.1% to 80%, by weight, preferably 0.25% to 5%, by weight.
  • Example I.-Preparati0n 0f polybutenyl succinic anhydride A mixture of 1000 grams (1 mol) of polybutene having a molecular weight of about 1000 and 98 grams (1 mol) of maleic anhydride was heated at 410 F. in a nitrogen atmosphere with agitation for a period of 24 hours. The reaction mixture was cooled to 150 F. and 700 cc. of hexane added; after which the mixture was filtered under vacuum. After vacuum distillation to remove the hexane from the filtrate, the product was maintained at 350 F. at an absolute pressure of 10 mm. Hg for one hour to remove traces of maleic anhydride. The crude polybutenyl succinic anhydride thus prepared had a saponification number of 79.
  • Example I1 Preparati0n of tetraethylenepentamine derivative 0 the polybutenyl succinic anhydride of Example l hereinabove
  • the temperature was increased to 400 F. during a period of one hour, after which the absolute pressure was reduced to about 200 mm. Hg during a period of 30 minutes to facilitate the removal of water.
  • the reaction mixture was then allowed to reach room temperature at this reduced pressure.
  • the compounds of this invention are more efiective than alkenyl succinimides having fewer nitrogen atoms in the amine portion of the molecule, and succinimides having less than 30 carbon atoms in the alkenyl radical.
  • amyl amine for example, in place of tetraethylene pentamine in the preparation of the succinimide, results in a product which is ineffective as a detergent in lubricating oil compositions.
  • Table I hereinbelow presents data obtained with lubricating oil compositions containing N-substituted monoalkenyl succinimides derived from tetraethylene pentamine.
  • the monoalkenyl succinimide used was an N-substituted succinimide derived from tetraethylene pentamine Wherein the alkenyl radical had a molecular weight of about 1000, which alkenyl radical was a polymer of isobutene.
  • the PD Nos. refer to the piston discoloration rating. After the engine test, the three piston lands are examined visually. To a piston skirt which is completely black is assigned a PD number of 800; to one which is completely clean, a PD number of 0; to those intermediate between completely black and completely clean are assigned PD numbers intermediate in proportion to the extent and degree of darkening.
  • the G.D. Nos. refer to the percentage deposits in the piston ring grooves; and 0 evaluation being a clean groove; and a number of 100 being a groove full of deposits.
  • the base oils were California SAE 30 base oils.
  • the dithiophosphate was a zinc salt of a mixed dialkyl dithiophosphate wherein one of the alkyl radicals contained 4 carbon atoms and the other alkyl radical contained 5 carbon atoms.
  • the dithiophosphate was present in the lubricating oil compositions in an amount of 18 millimols per kilogram (Le, 18 mm./kg.) of finished product, based on the metal content.
  • the piston varnish rating is a visual observation of the amount of varnish on a piston skirt, with 10 being the maximum rating for a perfectly clean piston and a 0 being the rating of a piston fully covered with black varnish. This piston varnish rating correlates with road performance in automobiles.
  • the total rating is the overall deposit rating of the engine.
  • the rating values range from 0, the poorest value, to 100, the top value. These figures indicate the percentage rating for the engine.
  • the base oil was an SAE base oil.
  • the succinimide and the dithiophosphate were the same as those described for Table I hereinabove.
  • Table 111 hereinbelow presents data obtained with lubricating oil compositions under L-4 test conditions.
  • This L-4 engine test which is fully described in the CRC Handbook, 1946 edition, Coordinating Research Council, New York, New York, is designed to evaluate the bearing corrosion characteristics and high temperature detergency of lubricating oil compositions. The detergency characteristics are rated by the piston varnish rating on the same scale described above for the FL-2 test. The L-4 test was continued beyond the normal 36 hours. The number of hours is the hours at which the same specimens were evaluated then placed in the engine for further testing.
  • the dithiophosphate was a zinc salt of a dialkyl dithiophosphate wherein one of the alkyl radicals contained 4 carbon atoms and the other alkyl radical contained 5 carbon atoms.
  • the succinimide and the dithiophosphate were the same as those described hereinabove.
  • the lead rating scale ranges from 10 for a clean engine, to zero for an engine containing heavy lead deposits.
  • piston varnish ratings were obtained, a value of 10 for a clean piston, and a value of zero for a piston heavy with varnish.
  • lubricating oil compositions containing the N-substituted alkenyl succinimides of tetraethylene pentamine of this invention may also contain other detergents, viscosity index improving agents, rust inhibitors, oiliness agents, grease thickening agents, etc.
  • a lubricating oil composition comprising a major proportion of an oil of lubricating viscosity, and in an amount sufficient to impart detergency characteristics thereto, a monoalkenyl succinimide of the formula:
  • R is a hydrocarbon radical having a molecular weight of from about 900 to about 3000.
  • a lubricating oil composition consisting essentially of an oil of lubricating viscosity, and from about 0.1% to about 80%, by weight, of a monoalkenyl succinirnide of tetraethylene pentamine of the formula:
  • R is a hydrocarbon radical derived from a polymer of an olefin containing from 2 to carbon atoms, said polymer having a molecular weight in the range of about 900 to about 3000.
  • a lubricating oil composition consisting essentially of an oil of lubricating viscosity, and from about 0.1% to about 80%, by weight, of a monoalkenyl succinirnide of tetraethylene pentamine of the formula:
  • R is a a hydrocarbon radical derived from a polymer of an olefin containing from 2 to 5 carbon atoms, said polymer having a molecular weight in the range of about 900 to about 1200.
  • R is a polymer of isobutene having a molecular Weight of about 1000.
  • a lubricating oil composition comprising a major proportion of a petroleum lubricating oil, and from about 0.25% to about 5%, by weight, of an N-substituted monoalkenyl succinimide of the formula:
  • structural formula R is a substantially aliphatic hydrocarbon radical of from to 200 carbon atoms, with an equal molar quantity of tetraethylene pentamine at a temperature in the range of 220 to 360 F.

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  • 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)
US835437A 1959-08-24 1959-08-24 Lubricating oil compositions containing alkenyl succinimides of tetraethylene pentamine Expired - Lifetime US3361673A (en)

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NL124842D NL124842C (it) 1959-08-24
US835411A US3202678A (en) 1959-08-24 1959-08-24 Alkenyl succinimides of tetraethylene pentamine
US835437A US3361673A (en) 1959-08-24 1959-08-24 Lubricating oil compositions containing alkenyl succinimides of tetraethylene pentamine
DE19601444798 DE1444798A1 (de) 1959-08-24 1960-08-10 Schmieroelgemische
GB27738/60A GB956802A (en) 1959-08-24 1960-08-10 Polyolefin substituted succinimides of tetraethylene pentamine and lubricating oil compositions containing the same
FR835957A FR1265086A (fr) 1959-08-24 1960-08-16 Compositions d'huiles lubrifiantes renfermant des alkényl succinimides de la tétraéthylène pentamine
NL6712905A NL6712905A (it) 1959-08-24 1967-09-21

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FR3110913A1 (fr) 2020-05-29 2021-12-03 Total Marketing Services Composition d’additifs pour carburant moteur
FR3110914A1 (fr) 2020-05-29 2021-12-03 Total Marketing Services Utilisation d’une composition de carburant pour nettoyer les parties internes des moteurs essence
WO2021240116A1 (fr) 2020-05-29 2021-12-02 Totalenergies Marketing Services Composition d'additifs pour carburant moteur
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FR3143625A1 (fr) 2022-12-19 2024-06-21 Totalenergies Onetech Composition de carburant comprenant une base renouvelable, un ester d’acide gras et un additif polysiloxane
WO2024134057A1 (fr) 2022-12-19 2024-06-27 Totalenergies Onetech Composition de carburant comprenant une base renouvelable, un ester d'acide gras et un additif polysiloxane
US11884890B1 (en) 2023-02-07 2024-01-30 Afton Chemical Corporation Gasoline additive composition for improved engine performance
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US11795412B1 (en) 2023-03-03 2023-10-24 Afton Chemical Corporation Lubricating composition for industrial gear fluids

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NL124842C (it)
US3202678A (en) 1965-08-24
NL6712905A (it) 1967-11-27
GB956802A (en) 1964-04-29
DE1444798A1 (de) 1969-04-30

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