US3018250A - Lubricating oil compositions containing nu-dialkylaminoalkyl alkenyl succinimides - Google Patents

Lubricating oil compositions containing nu-dialkylaminoalkyl alkenyl succinimides Download PDF

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Publication number
US3018250A
US3018250A US835390A US83539059A US3018250A US 3018250 A US3018250 A US 3018250A US 835390 A US835390 A US 835390A US 83539059 A US83539059 A US 83539059A US 3018250 A US3018250 A US 3018250A
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Prior art keywords
dialkylaminoalkyl
lubricating oil
alkenyl
carbon atoms
oil compositions
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US835390A
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Robert G Anderson
Frank A Stuart
Alan Y Drummond
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California Research LLC
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California Research LLC
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Priority to NL255194D priority Critical patent/NL255194A/xx
Priority to NL124306D priority patent/NL124306C/xx
Application filed by California Research LLC filed Critical California Research LLC
Priority to US835400A priority patent/US3018291A/en
Priority to US835390A priority patent/US3018250A/en
Priority to DEC22117A priority patent/DE1156926B/de
Priority to GB28419/60A priority patent/GB942818A/en
Priority to FR835956A priority patent/FR1265085A/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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/54—Preparation of carboxylic acid anhydrides
    • C07C51/567—Preparation of carboxylic acid anhydrides by reactions not involving carboxylic acid anhydride groups
    • 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
    • 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
    • C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
    • C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • 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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    • C10M2203/024—Well-defined aliphatic compounds unsaturated
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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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    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/108—Residual fractions, e.g. bright stocks
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    • C10M2223/04—Phosphate esters
    • C10M2223/045—Metal containing thio derivatives
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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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/047—Thioderivatives not containing metallic elements
    • 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
    • C10M2227/02—Esters of silicic acids
    • C—CHEMISTRY; METALLURGY
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    • 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
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    • 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
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    • 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
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    • 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
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    • 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
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    • 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
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    • 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
    • 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

  • This invention pertains to lubricating oil compositions containing N-dialkylaminoalkyl alkenyl succinimides as detergents.
  • 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 in hibitors in lubricating compositions.
  • products obtained by reacting such alkenyl succinic anhydrides with monoamines are taught as ferrous corrosion inhibitors for lubricating oil compositions.
  • alkenyl succinimides are not useful as detergents for lubricating oil compositions.
  • the alkenyl succinimides described herein are useful as detergents in lubricating oil compositions.
  • the various detergents which are fectiveness as detergents for dispersing the precursors 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 by fouling the spark plugs and valves and contributing to preignition.
  • N-dialkylaminoalkyl monoalkenyl succinimides wherein the alkenyl radical contains from 30 to 200 carbon atoms, and wherein said dialkylaminoalkyl radical contains a total of 3 to 10 carbon atoms, can be represented by the formula:
  • R and R contain a total of no more than 10 carbon atoms.
  • R is a polymer of an" olefin containing from 2 to 5 carbon atoms, wherein the polymer has a molecular weight from 400 to 3000, more particularly from about 900 to about 1200.
  • olefins are exemplified by ethylene, propylene, l-buteue, 2-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.
  • R' alkylene radicals include the divalent ethylene radical, propylene radical, butylene radical, etc.
  • R and R alkyl radicals include methyl, ethyl, propyl, etc. It is particularly preferred that R' contains 3 carbon atoms, and that R and R each contain 1 carbon atom.
  • the preparation of the monoalkenyl succinimides herein can be described generally by the following equations, wherein a polyolefin is reacted with maleic anhydride to form a monoalkenyl succinic anhydride, which, in turn, is then reacted with a dialkylaminoalkylamine to form an N-dialkylaminoalkyl monoalkenyl succinimide.
  • a polymer of isobutene as an example of the alkenyl radical
  • dimethylaminopropylamine to exemplify the dialkylaminoalkylamine
  • the reactants are used in such proportions and the reaction conditions are such that an imide is formed, not a diamide.
  • 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 obtained thereby, it is preferred to use the higher temperature range (e.g., 375 F. to 450 F.).
  • Equation 11 can be made at 220 F. to 500 F., preferably from 300 F. to 400 F.
  • the alkenyl succinic anhydride and the polyamine are reacted in about equal molar quantities.
  • An excess of amine can be used, and the unreacted amine removed by distillation.
  • the resulting alkenyl succinic anhydride may contain some unreactedpolyolefin.
  • 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 aceton or methanol from a hydrocarbon solution.
  • N-dialkylaminoalkyl monoalkenyl succinimides is illustrated in the following examples.
  • Example I -Preparatin of polybutenyl succinic anhydride
  • a mixture of 1000 grams (1 mol) of a polybutene having a molecular weight of about 1000 and 98 grams (1 mol) of maleic anhydride was heatedat 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 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 II Preparation of N-dimethylaminopmpyl polybutenyl succinimide
  • the identity of the N-dimethylaminopropylalkenyl succinimide was established by means of infrared spectroscopy.
  • Table I hereinbelow presents further data concerning the preparation of N-dialkylaminoalkyl alkenyl succinimides.
  • the polyamine was dimethylaminopropylamine, and the alkenyl radical on the alkenyl succinimide was a polybutene, the molecular weight of which is noted in Table 'I.
  • these alkenyl 'succinimides can be used in amounts'of 0.1% to by weight, preferably 0.25% to 5%, by weight.
  • Lubricating oils which can be used as base oils for lubricating oil compositions of such alkenyl succinimides 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., alkylene oxide polymers prepared by polymerizing the alkylene oxide, e.g., propylene oxide, etc., in the presence of water or alcohols, e.g., ethylene alcohol), dicarboxylic acid esters (e.g., those which are prepared by esterifying such dicarboxylic acids as adipic acid, azelaic acid, suberic acid, sebacic acid, alkanol succinic acid, fuma
  • the above base oils may be used individually or in combinations thereof, wherever miscible or wherever made so by the use of mutual solvents.
  • Table II hereinbelow sets forth data showing the dicetiveness of N-dialkylaminoalkyl monoalkenyl succinimides as lubricating oil additives.
  • the succinimide used was an N-dimethylaminopropyl alkenyl succinimide wherein the alkenyl radical had a molecular weight of approximately 1000, which alkenyl radical was a polymer of isobutene.
  • the base oil was an SAE 10 base oil.
  • the PD Nos. refer to the piston discoloration rating.
  • the three piston lands are examined visually. To a piston land which is completely black is assigned a PD number of 800; to one which is completely clean, a PD number of 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; an 0 evaluation being a clean groove;
  • Table III hereinbelow presents data showing the efiectiveness of these alkenyl succinimides in inhibiting piston varnish formation.
  • the piston varnish rating is a visual observation of the amount of varnish on a piston skirt, with 10 being the rating of a clean piston and "0" the rating of a piston fully covered with black varnish. This piston varnish rating correlates with road performance.
  • 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 concentration is expressed as millimols per kilogram (i.e., mMJkg.)
  • the alkenyl radical of the succinimide was an isobutene polymer having a molecular weight of about 700.
  • lubricating oil compositions containing the N-dialkylaminoalkyl alkenyl succinimides. 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 to impart detergency thereto, an N-dialkylaminoalkyl monoalkenyl succinimide, wherein said alkenyl radical contains from 30 to about 200 carbon atoms, and said dialkylaminoalkyl radical contains no more than 10 carbon atoms.
  • a lubricating oil composition comprising a major proportion of an oil of lubricating viscosity, and, in an amount to impart detergency thereto, an N-dialkylamino- 75 2,638,450
  • alkenyl radical is a polymer of an olefin containing from 2 to 5 carbon atoms, which polymer has a molecular weight from about 400 to about 3000, and said dialkylaminoalkyl radical contains from 3 to 10 carbon atoms.
  • a lubricating oil composition comprising a major proportion of an oil of lubricating viscosity, and, in an amount to impart detergency thereto, an N-dialkylaminoalkyl monoalkenyl succinimide, wherein said alkenyl radical is a polymer of an olefin containing from 2 to 5 carbon atoms, which polymer has a molecular weight from about 900 to about 1200, and said dialkylaminoalkyl radical containing from 3 to 10 carbon atoms.
  • a lubricating oil composition consisting essentially of an oil of lubricating viscosity and from 0.1% to by weight, of an N-dialkylarninoalkyl monoalkenyl succinimide wherein said alkenyl radical contains from 30 to about 200 carbon atoms, and said dialkylaminoalkyl radical contains from 3 to 10 carbon atoms.
  • a lubricatng oil composition comprising a major proportion of an oil of lubricating viscosity from 0.25%
  • N-dialkylaminoalkyl monoalkenyl succinimide of the formula:
  • R is 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, and R, R and R are aliphatic hydrocarbon radicals containing a sum total of 3 to 10 carbon atoms.
  • 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:
  • R is a polymer of isobutene having a molecular weight of about 1000
  • R, R and R are aliphatic GET-C CH3 0 wherein R is a polymer of an olefin containing 4 carbon atoms, said polymer having a molecular weight of about 1000.

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  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
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US835390A 1959-08-24 1959-08-24 Lubricating oil compositions containing nu-dialkylaminoalkyl alkenyl succinimides Expired - Lifetime US3018250A (en)

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NL124306D NL124306C (ja) 1959-08-24
US835400A US3018291A (en) 1959-08-24 1959-08-24 Nu-dialkylaminoalkyl alkenyl succinimides
US835390A US3018250A (en) 1959-08-24 1959-08-24 Lubricating oil compositions containing nu-dialkylaminoalkyl alkenyl succinimides
DEC22117A DE1156926B (de) 1959-08-24 1960-08-10 Schmieroele
GB28419/60A GB942818A (en) 1959-08-24 1960-08-16 N-dialkylaminoalkyl alkenyl succinimides and their use in lubricating compositions
FR835956A FR1265085A (fr) 1959-08-24 1960-08-16 Compositions d'huiles lubrifiantes renfermant des n-dialkylaminoalkyl alkényl succinimides

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US3018291A (en) 1962-01-23
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DE1156926B (de) 1963-11-07

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