US3018291A - Nu-dialkylaminoalkyl alkenyl succinimides - Google Patents
Nu-dialkylaminoalkyl alkenyl succinimides Download PDFInfo
- Publication number
- US3018291A US3018291A US835400A US83540059A US3018291A US 3018291 A US3018291 A US 3018291A US 835400 A US835400 A US 835400A US 83540059 A US83540059 A US 83540059A US 3018291 A US3018291 A US 3018291A
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- United States
- Prior art keywords
- alkenyl
- carbon atoms
- dialkylaminoalkyl
- reaction
- lubricating oil
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- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 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
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- C10M2227/02—Esters of silicic acids
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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
- 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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- 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
- C10M2229/041—Siloxanes with specific structure containing aliphatic substituents
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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
- 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
- C10M2229/043—Siloxanes with specific structure containing carbon-to-carbon double bonds
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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
- 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
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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
- 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
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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
- 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
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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
- 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
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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
- 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
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- 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
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- 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
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- 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
- R is an alkenyl radical containing from 30 to 200 carbon atoms
- R' is a divalent alkylene radical
- R and R are alkyl radicals.
- the sum of the carbon atoms in R, R and R is 3 to 10; that is, R, R and R con- 5 tain a total of no more than carbon atoms.
- R is a polymer of an olefin con- Calm, a corporation of Deaware taming from 2 to 5 carbon atoms, wherein the polymer N0 Drawing Filed Aug 24 1959, 335,409 has a molecular weight from 400 to 3000, more par- 3 C (CL 2 0 32 5 ticularly from about 900 to about 1200.
- olefins 10 are exemplified by ethylene, propylene, l-butene, 2-
- This invention pertains to a new class of compounds butene, isobutene, and mixtures thereof. Since the methparticularly useful as lubricating oil addition agents. ods of polymerizing the olefins to form polymers thereof These new compounds are N-dialkyl-aminoalkyl alkenyl is immaterial in the formation of the new compound de- Sllccinimides.
- alkeflyl R alkylene radicals include the divalent methylene 235.31% ti it iiifofi 212152iiiiifi ii fiiioitffi 3 1 gs g? f f ig hibitors in lubricating oil compositions.
- roduets m lca e a m lea S men 6 me 1 obtained by reacting such alkenyl succinic anhydrides propyl It Is pamculaflyz prefenfd that R with monoamines are taught as ferrous corrosion inhibicoinams 3 carbon atoms and that R and R each tors for lubricating oil compositions. tam atom
- the above known alkenyl succinimides are reactants used of the 9 not useful as detergents in lubricating oil compositions.
- alkenyl succinimides described methylamme, dlmethylamlnoethylamme, dlmethylaminoherein are new compounds which are useful as deter- P py dimethylaminobutylamine, dimethylaminogents in lubricating oil compositions.
- heptylamine diethylaminomethylamine, diethlaminopro-
- n is a number having a value of about 7 to about 50.
- the reaction set forth and described 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 higher temperature range (e.g., 375 F. 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 polyamine are reacted in about equal molar quantities. An excess of the amine can be used, and the unreacted amine removed by distillation.
- 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.
- these alkenyl succinimides can be used in amounts of 0.1% to by weight; preferably 0.25% to 5% by weight.
- Table II hereinbelow sets forth data showing the effectiveness of the new compounds of this invention as lubricating oil additives.
- the monoalkenyl 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 anSAE 10 base oil.
- the PD Nos. refer to the piston discoloration rating. After the engine test 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 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 clear groove; and a number of being a groove full of deposits.
- R is a polyisobutylene radical of from 30 to 200 carbon atoms
- R is a divalent alklyene radical of from 1 to 3 carbon atoms
- R and R are alkyl radicals of from 1 to 3 carbon atoms
- R, R and R combined con. tain a total of no more than 10 carbon atoms.
- the compound of the formula: of from 1 to 3 carbon atoms, and R, R and R como bined contain a total of no more than 10 carbon atoms.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Lubricants (AREA)
- Pyrrole Compounds (AREA)
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NL255194D NL255194A (zh) | 1959-08-24 | ||
NL124306D NL124306C (zh) | 1959-08-24 | ||
US835390A US3018250A (en) | 1959-08-24 | 1959-08-24 | Lubricating oil compositions containing nu-dialkylaminoalkyl alkenyl succinimides |
US835400A US3018291A (en) | 1959-08-24 | 1959-08-24 | Nu-dialkylaminoalkyl alkenyl succinimides |
DEC22117A DE1156926B (de) | 1959-08-24 | 1960-08-10 | Schmieroele |
FR835956A FR1265085A (fr) | 1959-08-24 | 1960-08-16 | Compositions d'huiles lubrifiantes renfermant des n-dialkylaminoalkyl alkényl succinimides |
GB28419/60A GB942818A (en) | 1959-08-24 | 1960-08-16 | N-dialkylaminoalkyl alkenyl succinimides and their use in lubricating compositions |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US835390A US3018250A (en) | 1959-08-24 | 1959-08-24 | Lubricating oil compositions containing nu-dialkylaminoalkyl alkenyl succinimides |
US835400A US3018291A (en) | 1959-08-24 | 1959-08-24 | Nu-dialkylaminoalkyl alkenyl succinimides |
Publications (1)
Publication Number | Publication Date |
---|---|
US3018291A true US3018291A (en) | 1962-01-23 |
Family
ID=27125786
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US835400A Expired - Lifetime US3018291A (en) | 1959-08-24 | 1959-08-24 | Nu-dialkylaminoalkyl alkenyl succinimides |
US835390A Expired - Lifetime US3018250A (en) | 1959-08-24 | 1959-08-24 | Lubricating oil compositions containing nu-dialkylaminoalkyl alkenyl succinimides |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US835390A Expired - Lifetime US3018250A (en) | 1959-08-24 | 1959-08-24 | Lubricating oil compositions containing nu-dialkylaminoalkyl alkenyl succinimides |
Country Status (4)
Country | Link |
---|---|
US (2) | US3018291A (zh) |
DE (1) | DE1156926B (zh) |
GB (1) | GB942818A (zh) |
NL (2) | NL255194A (zh) |
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US3087936A (en) * | 1961-08-18 | 1963-04-30 | Lubrizol Corp | Reaction product of an aliphatic olefinpolymer-succinic acid producing compound with an amine and reacting the resulting product with a boron compound |
US3136784A (en) * | 1959-10-12 | 1964-06-09 | Ciba Ltd | Beta-phosphate esters of -2-butenoates of mono glyceriate heterocyclic acetals and glyceriate carbonates |
US3154560A (en) * | 1961-12-04 | 1964-10-27 | Monsanto Co | Nu, nu'-azaalkylene-bis |
US3163603A (en) * | 1963-12-11 | 1964-12-29 | Lubrizol Corp | Amide and imide derivatives of metal salts of substituted succinic acids |
US3185704A (en) * | 1962-09-04 | 1965-05-25 | Exxon Research Engineering Co | Formamide of mono-alkenyl succinimide |
US3194813A (en) * | 1962-10-18 | 1965-07-13 | Lubrizol Corp | High molecular weight alkenyl-n-omega amino hexylsuccinimide |
US3194814A (en) * | 1962-10-18 | 1965-07-13 | Lubrizol Corp | High molecular weight alkenyl-n-allyl succinimide |
US3194812A (en) * | 1962-08-31 | 1965-07-13 | Lubrizol Corp | High molecular weight alkenyl-n-para amino-phenyl succinimide |
US3202679A (en) * | 1961-06-30 | 1965-08-24 | California Research Corp | Preparation of alkenyl succinic anhydrides |
US3219666A (en) * | 1959-03-30 | 1965-11-23 | Derivatives of succinic acids and nitrogen compounds | |
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Also Published As
Publication number | Publication date |
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DE1156926B (de) | 1963-11-07 |
NL255194A (zh) | |
NL124306C (zh) | |
US3018250A (en) | 1962-01-23 |
GB942818A (en) | 1963-11-27 |
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