US3024195A - Lubricating oil compositions of alkylpiperazine alkenyl succinimides - Google Patents

Lubricating oil compositions of alkylpiperazine alkenyl succinimides Download PDF

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Publication number
US3024195A
US3024195A US835391A US83539159A US3024195A US 3024195 A US3024195 A US 3024195A US 835391 A US835391 A US 835391A US 83539159 A US83539159 A US 83539159A US 3024195 A US3024195 A US 3024195A
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Prior art keywords
lubricating oil
alkylpiperazine
oil compositions
carbon atoms
lubricating
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US835391A
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English (en)
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Alan Y Drummond
Robert G Anderson
Frank A Stuart
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California Research LLC
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California Research LLC
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Priority to NL255193D priority Critical patent/NL255193A/xx
Application filed by California Research LLC filed Critical California Research LLC
Priority to US835391A priority patent/US3024195A/en
Priority to US835389A priority patent/US3024237A/en
Priority to GB26926/60A priority patent/GB934401A/en
Priority to FR836640A priority patent/FR1265784A/fr
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/40—2,5-Pyrrolidine-diones
    • C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
    • C07D207/408—Radicals containing only hydrogen and carbon atoms attached to ring carbon atoms
    • C07D207/412—Acyclic radicals containing more than six carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • 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
    • 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
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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
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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
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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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    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/04—Well-defined cycloaliphatic compounds
    • C—CHEMISTRY; METALLURGY
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    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/06—Well-defined aromatic compounds
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    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
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    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C—CHEMISTRY; METALLURGY
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    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • 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
    • C—CHEMISTRY; METALLURGY
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    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • 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
    • C—CHEMISTRY; METALLURGY
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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
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C—CHEMISTRY; METALLURGY
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    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • 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
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    • C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
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    • C10M2209/105—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only
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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
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    • C10M2215/086—Imides
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
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    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
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    • C10M2229/043—Siloxanes with specific structure containing carbon-to-carbon double 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
    • C10M2229/044—Siloxanes with specific structure containing silicon-to-hydrogen 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
    • C10M2229/045—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
    • 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.
  • metal-free detergents are N-substituted 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 non-cyclic monamines 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 organic group through an oxygen atom.
  • these metal-containing organic compounds have some effectiveness as detergents for dispersing the precursors of deposits within the oil itself rather than permitting them to form added deposits on the engine parts, they have the disadvantage of forming ash deposits in the engine. These ash deposits lower engine performance 2 by fouling spark plugs and valves, and contributing to preignition.
  • lubricating oil compositions particularly useful for heavy duty service are obtained by incorporating N-alkylpiperazine monoalkenyl succinimides in oils of lubricating viscosity.
  • N-alkylpiperazine monoalkenyl succinimides are new compounds of the formula:
  • 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; R is a hydrocarbon radical containing from 1 to 3 carbon atoms; and R" is hydrogen or a hydrocarbon radical containing from 1 to 3 carbon atoms.
  • N-substituted alkenyl succinimides can be prepared by reacting maleic anhydride with an olefinic hydrocarbon followed by reacting the resulting alkenyl succinic anhydride with an N-(p-aminoalkyl) piperazine.
  • N-(B-aminoalkyl) piperazines are exemplified by N-methyl-N-(fi-aminoethyl) piperazine, N-isopropyl-N'- (fiaminoethyl) piperazine, N-(B-aminoisopropyl) piperazine, etc.
  • the R radical of the above formula 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 amine derivatives of piperazine can be described generally by the following equations, using a polymer of isobutene as an example of the alkenyl radical; and N-(fi-aminoethyl) piperazine as an example of an N-(aminoalkyl) piperazine:
  • 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 to 450 F.).
  • Equation II The reaction described by Equation II hereinabove can be made at 220 F. to 500 F., preferably from 300 F. to 400 F.
  • the alkenyl succinic anhydride and the N-alkylaminepiperazines are reacted in about equal molar quantities.
  • the resulting alkenylsuccinic 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, paraifin base, and mixed base lubricating oils, other hydrocarbon lubricants, e.g., lubricating oils derived from coal products, and synthetic oils, e.g., alkylene poly- .mers (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, suberic acid, sebacic acid, alkanol succinic acid, furnaric acid, maleic acid, etc., with alcohols such as but
  • the above base oils may be used individually or in combinations thereof, wherever miscible or Wherever made so by the use of mutual solvents.
  • alkenyl succinimides of this in vention can be used in oils of lubricating viscosity in amounts of 0.1% to by weight, preferably 0.25% to 5%, by weight.
  • N-alkylpiperazine alkenyl succinimides is illustrated in the following examples.
  • Table I hereinbelow presents data obtained with lubricating oil compositions containing N-alkylpiperazine monoalkenyl succinimides.
  • 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 GD Nos. refer to the percentage deposits in the piston ring grooves; and 0 evaluation being a clean groove; and a number of being a groove full of deposits.
  • the base oils were California SAE 30 base oils.
  • GD N o 39 1 0.3 PD N0 800, 800, 800 25, 0, 5 10, 0, 0
  • Table II hereinbelow presents data obtained in an FL2 test, using a 6-cylinder Chrysler engine operating at 2500 r.p.m. for a period of 40 hours, which test is fully described in a Coordinating Research Council bulletin titled Research Technique for the Determination of the Elfects of Fuels and Lubricants on the Formation of Deposits During Moderate Temperature Operation (1948).
  • 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 base oil was an SAE 30 base oil.
  • the succinimide and the dithiophosphate were the same as those described for Table I hereinabove.
  • lubricating oil compositions containing the N-substituted alkenyl succinimides of N-alkylpiperazine of this invention may also contain other detergents, viscosity index improving agents, rust inhibitors, oiliness agents, grease thickening agents, etc.
  • a lubricating oil composition consisting essentially of an oil of lubricating viscosity and from 0.1% to 80%, by Weight, of an N-alkylpiperazine monoalkenyl succinimide of the formula:
  • R is a hydrocarbon radical having a molecular weight from about 400 to about 3000, and R is a hydrocarbon radical containing from 1 to 3 carbon atoms.
  • a lubricating oil composition consisting essentially of an oil of lubricating viscosity and from 0.1% to by weight, of an N-alkylpiperazine monoalkenyl succinimide of the formula:
  • R is a hydrocarbon radical having a molecular weight from about 900 to about 1200, and R' is a hydrocarbon radical containing from 1 to 3 carbon atoms.
  • a lubricating oil composition comprising a major proportion of an oil of lubricating viscosity and firom 0.25 to 5%, by weight, of an N-alkylpiperazine monoalkenyl succinimide of the formula:
  • R is a hydrocarbon radical having a molecular weight from about 900 to about 1200, and R is a hydrocarbon radical containing from 1 to 3 carbon atoms, and R" is selected from the group consisting of hydrogen and hydrocarbon radicals containing from 1 to 3 carbon atoms.
  • a lubricating oil composition comprising a major proportion of a petroleum lubricating oil and from 0.25% to 5%, by weight, of an N-substituted monoalkenyl succinimide of the formula:
  • a lubricating oil composition comprising a major proportion of an oil of lubricating viscosity and a minor proportion, in an amount sufiicient to impart detergency to said oil, of an N-alkylpiperazine monoalkenyl succinim ide of the formula:
  • R is a hydrocarbon radical having a molecular weight from about 400 to about 3,000
  • R is a hydrocarbon radical containing from one to three carbon atoms
  • R" is selected from the group consisting of hydrogen and hydrocarbon radicals containing from 1 to 3 carbon atoms.
  • a lubricating oil composition comprising a major proportion of an oil of lubricating viscosity and a minor proportion, an amount sufiicient to impart detergency to said oil, of an N-alkylpiperazine monoalkenyl succinimide of the formula:
  • R is a hydrocarbon radical containing from about 30 to about 200 carbon atoms formed by polymerizing olefins containing from 2 to 5 carbon atoms, and R is a hydrocarbon radical containing from 1 to 3 carbon atoms.
  • a lubricating oil composition consisting essentially of an oil of lubricating viscosity and from about 0.1% to about 80%, by weight, of an N-alkylpiperazine monoalkenyl succinimide of the formula:
  • R is an aleknyl radical containing from 30 to 200 carbon atoms and which is a polymer of an olefin containing from 2 to 5 carbon atoms, and R is an alkyl radical containing from 1 to 3 carbon atoms.
  • a lubricating oil composition comprising a" major C II;
  • n has a value of about 7 to about 50.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Lubricants (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
US835391A 1959-08-24 1959-08-24 Lubricating oil compositions of alkylpiperazine alkenyl succinimides Expired - Lifetime US3024195A (en)

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NL255193D NL255193A (de) 1959-08-24
US835391A US3024195A (en) 1959-08-24 1959-08-24 Lubricating oil compositions of alkylpiperazine alkenyl succinimides
US835389A US3024237A (en) 1959-08-24 1959-08-24 Alkenyl succinimides of piperazines
GB26926/60A GB934401A (en) 1959-08-24 1960-08-03 Alkylpiperazine alkenyl succinimides and their use in lubricating oil compositions
FR836640A FR1265784A (fr) 1959-08-24 1960-08-24 Alkényl-succinimides de n-alkylpipérazine détergentes et compositions d'huiles lubrifiantes les contenant

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