US3359204A - Lubricating oil dispersant - Google Patents
Lubricating oil dispersant Download PDFInfo
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- US3359204A US3359204A US602568A US60256866A US3359204A US 3359204 A US3359204 A US 3359204A US 602568 A US602568 A US 602568A US 60256866 A US60256866 A US 60256866A US 3359204 A US3359204 A US 3359204A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
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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
- 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
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/024—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings having at least two phenol groups but no condensed ring
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- 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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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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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- C—CHEMISTRY; METALLURGY
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
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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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- 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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- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
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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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/221—Six-membered rings containing nitrogen and carbon only
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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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
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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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
- C10M2215/226—Morpholines
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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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/26—Amines
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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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/30—Heterocyclic compounds
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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
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/022—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amino group
- C10M2217/023—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amino group the amino group containing an ester bond
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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
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/046—Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
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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
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
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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
- 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
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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
- 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
- C10M2223/042—Metal salts thereof
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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
- 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
- C10M2223/045—Metal containing thio derivatives
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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
- C10M2229/02—Unspecified siloxanes; Silicones
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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
- C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
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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
Definitions
- This invention relates to oil-soluble lubricating oil dispersants.
- it relates to the reaction product of high molecular weight alkenyl succinic anhydrides or acids (hereafter termed ASA) with tertiary amines which contain both an a'lkanol and a cyanoalkyl radical.
- ASA high molecular weight alkenyl succinic anhydrides or acids
- the various detergents which have been used to effectively disperse 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 detergents also neutralize to some extent the organic acids, and thereby help prevent corrosion of the engine parts.
- such detergents have the disadvantage of forming ash deposits in the engine, which deposits lower engine performance by fouling the spark plugs and valves and by contributing to preignition.
- dispersants In recent years, various non-ash producing dispersants have been devised to overcome these disadvantages.
- dispersants are imides, for example, N-dialkylarninoalkyl alkenyl succinimide, produced by the reaction of an alkenyl succinic anhydride and a dialkyl- 'aminoalkylamine.
- Other dispersants are prepared by the reaction of an ASA with alkylenepolyamines such as tetraethylenepentamine.
- ASA alkylenepolyamines
- tetraethylenepentamine A number of such dispersants are disclosed by Norman et al., US. 3,219,666, issued Nov. 23, 1965. These products all have in common the fact that they are prepared from primary or secondary amines which readily enter into amide or imide formations when reacted with ASA.
- a very effective class of ashless dispersants can be prepared by reacting an ASA with a specific type of tertiary amine.
- the tertiary amine employed must have at least one alkanol substituent and at least one cyanoalkyl substituent. Dispersants prepared employing this class of tertiary amines not only have excellent dispersing properties, but result in a lubricant with a reduced tendency to cause corrosion of metal engine parts.
- an object of this invention is to provide improved lubricant compositions.
- a further object is to provide lubricating oils having a high degree of dispersancy and low corrosivity.
- A one mole part of a succinic acid generating reactant selected from the group consisting of alkenyl succinic acid and alkenyl succinic anhydride wherein the alkenyl portion has a molecular weight of from 700 to 1600 with (B) from about 0.6 to 3 mole parts of a tertiary amine having the formula:
- n is an integer from 1-2
- m. is an integer from 1-2, the sum of it plus m is 2-3
- R and R are divalent hydrocarbon radicals containing 2-5 carbon atoms
- R is an alkyl radical containing from 1 to about 18 carbon atoms
- reaction being carried out at a temperature of from about to 200 C.
- the succinic acid generating reactant is an ASA wherein the alkenyl radical is derived from the polymerization of a monoolefin containing from 2-5 carbon atoms such that the alkenyl radical has a molecular weight of from about 700 to 1600.
- the succinic acid generating reactant is an ASA wherein the alkenyl radical is derived from a polybutene having a molecular weight of from about 800 to 1400 and wherein the tertiary amine reactant is S-[bis(2-hydroxyethyl)amino] propionitrile.
- the alkenyl portion of the ASA is a high molecular weight hydrocarbon radical. It is preferably derived from the polymerization of a monoolefin containing from 2-5 carbon atoms such as ethylene, propylene, butylene, isobutylene, n-pentene, isopentene, and the like.
- the polymer can have a molecular weight of from about 350 to 2000.
- the alkenyl radical has a molecular weight of from about 700 to 1600.
- the alkenyl group is derived from a polybutene having a molecular weight of from about 800 to 1400.
- the polymer employed in making the ASA has a narrow molecular weight range.
- alkenyl succinic anhydride or acid Methods of preparing the alkenyl succinic anhydride or acid are known to the art.
- an appropriate polyolefin is reacted with a maleic anhydride. If an alkenyl succinic acid is desired, the anhydride can be hydrolyzed.
- Example 1 illustrates the preparation of an alkenyl succinic anhydride in which the alkenyl group is a polybutene.
- EXAMPLE 1 A reaction vessel equipped with heating means, temperature measuring means, stirring means, a reflux condenser, gas inlet and outlet means and a nitrogen source is flushed with nitrogen and 23.5 parts of polybutene having a molecular weight of 1244 and 1.85 parts of maleic anhydride are added. The reactants are stirred at 215-220 C. for 24 hours, allowed to cool and 11.1
- Dilution of the reaction product before filtration can be done with solvents other than hexane such as benzene, toluene, xylene, etc. It may be desired to dilute the final ASA-tertiary amine reaction product with oil in order to improve handling properties. If such is the case, that diluent can be used in place of hexane in the above preparation of ASA. If an oil diluent is used it is desirable to strip the unreacted maleic anhydride before filtration. A temperature of about 180-185 C. is recommended if a strip procedure is used because at this temperature maleic acid will isomerize to fumaric acid, which is insoluble and readily removed by filtration.
- Suitable tertiary amines containing both alkanol and cyanoalkyl radicals include 3- [bis 3-hydroxy-n-propyl) amino] propionitrile,
- alkenyl succinic anhydride rather than the acid, although the acid can be used.
- Use of the acid results in no savings, but requires an additional hydrolysis step from the anhydride.
- Either product will react with the tertiary amines defined by this invention but the anhydride reacts with the formation of less water, and results in a more desirable product, and so is preferred.
- the mole ratio of tertiary amine to ASA is critical to the effectiveness of the final product.
- ASAs prepared from commercially available polyalkenes generally contain some unreacted polyalkenes. Accordingly, analysis of the ASA prior to reaction to determine its average molecular weight is desirable. In general, a ratio of from about 0.6 to 3 moles of tertiary amine per mole of ASA can be used. A range of from about 0.75 to 1.2 moles of tertiary amine per mole of ASA is preferred. A particularly preferred range is from 0.9 to 1.1 moles of tertiary amine per mole of ASA.
- the tertiary amine is generally less viscous than the ASA and is preferably added to a solution of ASA in a solvent.
- Preferred solvents are hydrocarbons having a boiling point of from about 100-200 C. More preferred solvents are the aromatic hydrocarbon solvents within this boiling range. A most preferred solvent is xylene.
- the tertiary amine is generally added to the ASA solution at a temperature on the order of 60-70 C.
- the mixture is then reacted, preferably under reflux, at from about -200 C.
- a reaction temperature of from about -180 C. is preferred.
- the solvent is chosen to conveniently maintain the reaction under reflux at the desired temperature in order to azeo trope with the Water formed during the reaction facilitating the removal of the water. Reaction times are generally from about one-half hour to about 8 hours. In most cases, a reaction time of from one to 4 hours is sufficient.
- the temperature can be raised in order to allow removal of solvent and residual Water.
- the last of the solvent and water is generally removed by reducing the pressure in the system, causing the solvent to distill out at lower temperatures down to about 100 C.
- EXAMPLE 2 A series of eight reactions was conducted according to the following procedure. In each case an ASA prepared as in Example 1 was added to a reaction vessel equipped with a stirrer, thermometer, heating means, Dean Stark water trap, condenser and a vacuum pump. In each case, 3-[bis(2-hydroxyethyl)amino]propionitrile was employed as the tertiary amine reactant. Also, xylene was used as a solvent in an amount of about one part of xylene for 4.5 parts of ASA. Each reaction differed in the mole ratio of ASA to tertiary amine excepting the first two, which differed in the molecular weight of the alkenyl radical on the ASA. The following table shows the reactant ratio employed in each reaction.
- the products of this invention are quite viscous at room temperature.
- a desirable viscosity range for a dispersant is about 300-400 SUS at 100 C., and about 10,000 SUS at 160 F.
- Heating the product before use allows it to be handled effectively, but preferably the product is diluted with an oil such as a No. 9 refined oil, or other products, for example, Humble SEN-100 or Texaco SEN-'5.
- the oil may be added to the product after its formation or it may be added to the ASA prior to the reaction with the tertiary amine.
- the preferred method is to add the oil diluent after the preparation of the final product.
- Fuel oil discrepancy test This is the Socony-Mobile test described in Ind. Eng. Chem, 48, 1892 (1956).
- One gallon samples of No. 9 refined oil containing the additive at a concentration of 25 pounds per 1,000 pounds, 1.0 gram of Germantown Bear Lamp'black and ml. of water were circulated through a 100 mesh strainer for two hours. The sludge deposit was then washed off the strainer, dried and weighed. The effectiveness of an additive is expressed as the percentage reduction in deposit weight, referred to as a baseline.
- Product G the product prepared in above Example 2 designated Product G, the amount of deposit on the screen was reduced 97 percent below baseline.
- Oxidative deterioration of the oil was further promoted by employing 0.10 weight percent of lead bromide as an oxidation catalyst. Further a copper-lead bearing was submerged in the oil as an additional catalyst. To approximate use conditions, 0.08 weight percent zinc dithiophospha-te was added. At the end of the test, the loss of weight of the copper lead hearing was determined. (When no loss in weight occurs a small increase in weight may be observed which can be attributable to the formation of a slight amount of varnish, which is to be expected from the harsh condition of the test.)
- Used Oil dispersancy test 40 grams of the used oil obtained from the CLR-L-38 Polyveriform Test conducted above are combined with 60 grams of new oil. The Sludge Dispersancy Test described above is then run using this oil; that is, 2 grams of Water and additional sludge are added. Emulsification and centrifugation are the same as in that test. A photometer reading is also taken on a blank, the mixture of used and new oil prior to running the Sludge Dispersancy Test, and the percent transmission obtained from the Sludge Dispersancy Test is divided by the percent transmission of the blank to give the final used oil dispersion percent transmission value. The results of this test as well as of the Polyveriforrn Test described above are listed.
- EXAMPLE 3 The reaction vessel of Example 2 is flushed with nitrogen and 0.5 mole of an ASA derived from a polyethylene having a molecular weight of 600 and 180 ml. of cumene are added. The mixture is heated to 70 C. "and 0.5 mole of 6 [(2 hydroxyisopropyl)amino] n capronitrile is quickly added. Heating is continued to reflux, about C. Additional cumene is added to maintain the temperature at about 160 C. for about six hours. Cumene is then distilled oif to allow the temperature to rise to about C. and the mixture is held at that temperature for about one hour to remove cumene. The resulting product can be added to lubricating oil to dispense sludgeforming materials.
- ASAs derived by the polymerization of other ole-fins such as propylene, isobutylene, n-pentene and isopentene.
- other tertiary amines which contain both a hydroxyalkyl and a cyanoalkyl substituent can be profitably employed.
- the detergent-dispersants of this invention are effective in both hydrocarbon and synthetic diester lubricating oils, including lubricating oils used in spark-ignition engines and diesel engine lubricants.
- Suitable base oils include petroleum-derived hydrocarbon mineral oils and also synthetic diester oils, such as sebacates, adipates, silicones, halogen containing organic compounds including the fluorocarbons, etc, polyalkylene glycol lubricants and organic phosphites which are suitable as lubricants.
- EXAMPLE 4 Product from Example 2: Cone (wt. percent) A 0.01 B 0.1 C l D 2 E 5 F 7 G 10 EXAMPLE 5 Lubricating oils are prepared as in Example 4 by blending the listed oil with the products prepared in Example 2. (A) A dioctyl sebacate having a viscosity at 210 F. of
- (B) A di-(sec-amyl) sebacate having a viscosity at 210 F. of 33.8 SUS, a viscosity index of 133 and a molecular weight of 342.5.
- (C) A di-(Z-ethylhexyl) sebacate having a viscosity at 210 F. of 37.3 SUS, a viscosity index of 152 and a molecular weight of 426.7.
- An ashless lubricant dispersant comprising the reaction product of:
- A one mole part of a succinic acid generating reactant selected from the group consisting of alkenyl succinic acid and alkenyl succinic anhydride wherein the alkenyl portion has a molecular weight of from 700 to 1600 with (B) from about 0.6 to 3 mole parts of a tertiary amine having the formula:
- n is an integer from 1-2
- m is an integer from 1-2
- the sum of n plus in is 2-3
- R and R are divalent hydrocarbon radicals containing 2-5 carbon atoms
- R is an alkyl radical containing from 1 to about 18 carbon atoms; said reaction being carried out at a temperature of from about 100 to 200 C.
- composition of claim 1 wherein said succinic acid generating group is an alkenyl succinic anhydride wherein the alkenyl radical is derived from the polymerization of a monoolefin containing 25 carbon atoms such that said alkenyl radical has a molecular weight of from about 700 to 1600.
- composition of claim 2 wherein said alkenyl radical is derived from a polybutene having a molecular Weight of from 800 to 1400 and wherein said tertiary amine is 3-[bis(2-hydroxyethyl)amino1propionitrile.
- a lubricating oil containing from 0.01 to 10 weight percent of the composition of claim 2.
- a hydrocarbon lubricating oil containing from 0.01 to about 10 weight percent of the composition of claim 3.
Description
United States Patent Ofiice 3,359,204 Patented Dec. 19, 1967 ABSTRACT OF THE DISCLOSURE The reaction product of a high molecular weight alkenyl succinic acid or anhydride with a tertiary amine having at least one alkanol and one cyanoalkyl group bonded to nitrogen is an effective ashless dispersant for lubricating oils.
This application is a continuation-in-part of co-pending application Ser. No. 387,216, filed Aug. 3, 1964, now abandoned.
This invention relates to oil-soluble lubricating oil dispersants. In particular, it relates to the reaction product of high molecular weight alkenyl succinic anhydrides or acids (hereafter termed ASA) with tertiary amines which contain both an a'lkanol and a cyanoalkyl radical.
A large percentage of todays automobiles are used in city stop-and-go driving where the engines do not reach their most etficient operating temperatures. Large amounts of partial oxidation products are formed and reach the crankcase of the engine by blowing past the piston rings. Most of these partial oxidation products are oil insoluble, and tend to form deposts on various operating parts of engines, resulting in sludge and varnish. Other deposits and organic acids result from deterioration of the oil itself. To prevent deposition of these materials on various engine parts, it is necessary to incorporate detergents in the lubricating oil compositions, thus keeping these polymeric products highly dispersed in a condition unfavorable for deposition on metals.
For the most part, the various detergents which have been used to effectively disperse 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 detergents also neutralize to some extent the organic acids, and thereby help prevent corrosion of the engine parts. However, such detergents have the disadvantage of forming ash deposits in the engine, which deposits lower engine performance by fouling the spark plugs and valves and by contributing to preignition.
In recent years, various non-ash producing dispersants have been devised to overcome these disadvantages. Among such dispersants are imides, for example, N-dialkylarninoalkyl alkenyl succinimide, produced by the reaction of an alkenyl succinic anhydride and a dialkyl- 'aminoalkylamine. Other dispersants are prepared by the reaction of an ASA with alkylenepolyamines such as tetraethylenepentamine. A number of such dispersants are disclosed by Norman et al., US. 3,219,666, issued Nov. 23, 1965. These products all have in common the fact that they are prepared from primary or secondary amines which readily enter into amide or imide formations when reacted with ASA. It has now been discovered that a very effective class of ashless dispersants can be prepared by reacting an ASA with a specific type of tertiary amine. The tertiary amine employed must have at least one alkanol substituent and at least one cyanoalkyl substituent. Dispersants prepared employing this class of tertiary amines not only have excellent dispersing properties, but result in a lubricant with a reduced tendency to cause corrosion of metal engine parts.
Accordingly, an object of this invention is to provide improved lubricant compositions. A further object is to provide lubricating oils having a high degree of dispersancy and low corrosivity.
These and other objects are accomplished by providing an ashless dispersant which comprises the reaction product of:
(A) one mole part of a succinic acid generating reactant selected from the group consisting of alkenyl succinic acid and alkenyl succinic anhydride wherein the alkenyl portion has a molecular weight of from 700 to 1600 with (B) from about 0.6 to 3 mole parts of a tertiary amine having the formula:
wherein n is an integer from 1-2, m. is an integer from 1-2, the sum of it plus m is 2-3, R and R are divalent hydrocarbon radicals containing 2-5 carbon atoms, and R is an alkyl radical containing from 1 to about 18 carbon atoms;
said reaction being carried out at a temperature of from about to 200 C.
In a preferred embodiment the succinic acid generating reactant is an ASA wherein the alkenyl radical is derived from the polymerization of a monoolefin containing from 2-5 carbon atoms such that the alkenyl radical has a molecular weight of from about 700 to 1600.
In a most preferred embodiment the succinic acid generating reactant is an ASA wherein the alkenyl radical is derived from a polybutene having a molecular weight of from about 800 to 1400 and wherein the tertiary amine reactant is S-[bis(2-hydroxyethyl)amino] propionitrile.
The alkenyl portion of the ASA is a high molecular weight hydrocarbon radical. It is preferably derived from the polymerization of a monoolefin containing from 2-5 carbon atoms such as ethylene, propylene, butylene, isobutylene, n-pentene, isopentene, and the like. The polymer can have a molecular weight of from about 350 to 2000. In a preferred embodiment the alkenyl radical has a molecular weight of from about 700 to 1600. In a most preferred embodiment the alkenyl group is derived from a polybutene having a molecular weight of from about 800 to 1400. Of course, those are understood to be average molecular weights since a polymerization leads to a mixture of polymers which cannot readily be separated into individual pure compounds. Preferably the polymer employed in making the ASA has a narrow molecular weight range.
Methods of preparing the alkenyl succinic anhydride or acid are known to the art. In general, to obtain an alkenyl succinic anhydride, an appropriate polyolefin is reacted with a maleic anhydride. If an alkenyl succinic acid is desired, the anhydride can be hydrolyzed.
In the following examples all parts are by weight. Example 1 illustrates the preparation of an alkenyl succinic anhydride in which the alkenyl group is a polybutene.
EXAMPLE 1 A reaction vessel equipped with heating means, temperature measuring means, stirring means, a reflux condenser, gas inlet and outlet means and a nitrogen source is flushed with nitrogen and 23.5 parts of polybutene having a molecular weight of 1244 and 1.85 parts of maleic anhydride are added. The reactants are stirred at 215-220 C. for 24 hours, allowed to cool and 11.1
parts of hexane are added. The mixture is allowed to set for about several hours and is then filtered through Celite via a Buchner funnel. Hexane is stripped from the filtrate at atmospheric pressure at 175 C. and then the pressure is reduced slowly to about 11 mm., holding the temperature at about 170-180 C. for about one hour, during which time maleic anhydride is removed. In an average run 10.8 parts of hexane and 0.21 part of maleic anhydride are recovered, leaving 22.9 parts of alkenyl succinic anhydride.
Dilution of the reaction product before filtration can be done with solvents other than hexane such as benzene, toluene, xylene, etc. It may be desired to dilute the final ASA-tertiary amine reaction product with oil in order to improve handling properties. If such is the case, that diluent can be used in place of hexane in the above preparation of ASA. If an oil diluent is used it is desirable to strip the unreacted maleic anhydride before filtration. A temperature of about 180-185 C. is recommended if a strip procedure is used because at this temperature maleic acid will isomerize to fumaric acid, which is insoluble and readily removed by filtration.
Some examples of suitable tertiary amines containing both alkanol and cyanoalkyl radicals include 3- [bis 3-hydroxy-n-propyl) amino] propionitrile,
4- [bis (Z-hydroxy-n-propyl) amino] -butyrylnitrile,
2- [bis (2-cyanoethyl) amino] ethanol,
3 [bis Z-cyano-n-propyl) amino] -n-propanol,
N- Zcyanoethyl (N hydroxyethyl (-methylamine,
N- (Z-cyano-n-propyl) -N- 3-hydroxy-n-propyl) laurylamine, and
(S-hydroxy-n-pentyl stearylamine.
The exact nature of the product formed is not known. On first inspection of the reactants it would appear that simple or polymeric esters of the ASA would result since tertiary amines dont form amides. However, with the specific tertiary amines employed in the present invention the products formed are much more complex than this and are best defined by the procedure used in their preparation.
In preparing the final product it is preferred to use alkenyl succinic anhydride rather than the acid, although the acid can be used. Use of the acid results in no savings, but requires an additional hydrolysis step from the anhydride. Either product will react with the tertiary amines defined by this invention but the anhydride reacts with the formation of less water, and results in a more desirable product, and so is preferred.
In reacting the ASA with the tertiary amine, the mole ratio of tertiary amine to ASA is critical to the effectiveness of the final product. ASAs prepared from commercially available polyalkenes generally contain some unreacted polyalkenes. Accordingly, analysis of the ASA prior to reaction to determine its average molecular weight is desirable. In general, a ratio of from about 0.6 to 3 moles of tertiary amine per mole of ASA can be used. A range of from about 0.75 to 1.2 moles of tertiary amine per mole of ASA is preferred. A particularly preferred range is from 0.9 to 1.1 moles of tertiary amine per mole of ASA. This latter range yields products with particularly good dispersant characteristics and with a minimum of corrosive side eflects. At lower ratios than those given, dispersancy of the product is generally unsatisfactory. At higher ratios, corrosion problems hecome very serious, resulting, for example, in high hearing weight loss.
The tertiary amine is generally less viscous than the ASA and is preferably added to a solution of ASA in a solvent. Preferred solvents are hydrocarbons having a boiling point of from about 100-200 C. More preferred solvents are the aromatic hydrocarbon solvents within this boiling range. A most preferred solvent is xylene.
The tertiary amine is generally added to the ASA solution at a temperature on the order of 60-70 C. The mixture is then reacted, preferably under reflux, at from about -200 C. In general, a reaction temperature of from about -180 C. is preferred. The solvent is chosen to conveniently maintain the reaction under reflux at the desired temperature in order to azeo trope with the Water formed during the reaction facilitating the removal of the water. Reaction times are generally from about one-half hour to about 8 hours. In most cases, a reaction time of from one to 4 hours is sufficient.
Following the above reaction, the temperature can be raised in order to allow removal of solvent and residual Water. The last of the solvent and water is generally removed by reducing the pressure in the system, causing the solvent to distill out at lower temperatures down to about 100 C.
The following example illustrates the reaction of an ASA with the preferred tertiary amine of this invention. All parts are parts by weight unless otherwise specified.
EXAMPLE 2 A series of eight reactions was conducted according to the following procedure. In each case an ASA prepared as in Example 1 was added to a reaction vessel equipped with a stirrer, thermometer, heating means, Dean Stark water trap, condenser and a vacuum pump. In each case, 3-[bis(2-hydroxyethyl)amino]propionitrile was employed as the tertiary amine reactant. Also, xylene was used as a solvent in an amount of about one part of xylene for 4.5 parts of ASA. Each reaction differed in the mole ratio of ASA to tertiary amine excepting the first two, which differed in the molecular weight of the alkenyl radical on the ASA. The following table shows the reactant ratio employed in each reaction.
Molecular wt. of Polybuteno in ASA Ratio Product ASA/Amine The reactions were conducted under a nitrogen atmosphere by warming the ASA-xylene solution to about 70 C. and then adding the 3-[bis(2-hydroxyethyl)amino] propionitrile. The mixture was then heated to reflux at about -16S" C. The water which codistilled with the xylene was condensed, collected, and removed by way of the Dean Stark separator. The reaction was conducted for about 3 hours at 160-16S C. and then sufiicient xylene was distilled out to allow the temperature to rise to about C. The reaction was maintained at 180- C. for about an hour. Heating was then discontinued and when the product had cooled to about 150 C. the pressure in the system was gradually reduced to about 10 mm., keeping the temperature of the product at about 110 C. This accomplished the removal of the last of the xylene solvent. All of the products produced in the above reactions were excellent dispersants.
The products of this invention are quite viscous at room temperature. A desirable viscosity range for a dispersant is about 300-400 SUS at 100 C., and about 10,000 SUS at 160 F. Heating the product before use allows it to be handled effectively, but preferably the product is diluted with an oil such as a No. 9 refined oil, or other products, for example, Humble SEN-100 or Texaco SEN-'5. The oil may be added to the product after its formation or it may be added to the ASA prior to the reaction with the tertiary amine. The preferred method is to add the oil diluent after the preparation of the final product.
To demonstrate the effectiveness of the products of this invention various representative products were tested in a Fuel Oil Dispersancy Test, a CLR-L-38 Polyveriform Test and a Used Oil Sludge Dispersancy Test.
Fuel oil discrepancy test This is the Socony-Mobile test described in Ind. Eng. Chem, 48, 1892 (1956). One gallon samples of No. 9 refined oil containing the additive at a concentration of 25 pounds per 1,000 pounds, 1.0 gram of Germantown Bear Lamp'black and ml. of water were circulated through a 100 mesh strainer for two hours. The sludge deposit was then washed off the strainer, dried and weighed. The effectiveness of an additive is expressed as the percentage reduction in deposit weight, referred to as a baseline. When the above test was conducted using as a dispersant the product prepared in above Example 2 designated Product G, the amount of deposit on the screen was reduced 97 percent below baseline.
CLR-L-3 8 polyveriform test This is a modification of the 'Polyveriform Oxidation Stability Test described in the paper entitled, Factors Causing Lubricating Oil Deterioration in Engines, Ind. Eng. Chem, Anal. Ed., 17, 302 (1945). See also A Bearing Corrosion Test for Lubricating Oils and its Correlation with Engine Performance, Anal. Chem, 21, 737 (1949). In thes tests an initially additive-free, 105.5 V.I. solvent-refined SAE-20 crankcase oil was used. The principal conditions consisted of passing 48 liters of air per hour through the test oil for a total period of 48 hours while maintaining the oil at a temperature of 300 F. Oxidative deterioration of the oil was further promoted by employing 0.10 weight percent of lead bromide as an oxidation catalyst. Further a copper-lead bearing was submerged in the oil as an additional catalyst. To approximate use conditions, 0.08 weight percent zinc dithiophospha-te was added. At the end of the test, the loss of weight of the copper lead hearing was determined. (When no loss in weight occurs a small increase in weight may be observed which can be attributable to the formation of a slight amount of varnish, which is to be expected from the harsh condition of the test.)
Used Oil dispersancy test In this test, 40 grams of the used oil obtained from the CLR-L-38 Polyveriform Test conducted above are combined with 60 grams of new oil. The Sludge Dispersancy Test described above is then run using this oil; that is, 2 grams of Water and additional sludge are added. Emulsification and centrifugation are the same as in that test. A photometer reading is also taken on a blank, the mixture of used and new oil prior to running the Sludge Dispersancy Test, and the percent transmission obtained from the Sludge Dispersancy Test is divided by the percent transmission of the blank to give the final used oil dispersion percent transmission value. The results of this test as well as of the Polyveriforrn Test described above are listed.
Product from Bearing wt. Example 2 Percent Light loss (mg.)
Transmission The above tests demonstrate that the present dispersants not only impart dispersancy to the oil, but give a nonc-orrosive lubricant.
Other dispersants within the scope of this invention can readily be prepared following the general procedure of Example 2.
EXAMPLE 3 The reaction vessel of Example 2 is flushed with nitrogen and 0.5 mole of an ASA derived from a polyethylene having a molecular weight of 600 and 180 ml. of cumene are added. The mixture is heated to 70 C. "and 0.5 mole of 6 [(2 hydroxyisopropyl)amino] n capronitrile is quickly added. Heating is continued to reflux, about C. Additional cumene is added to maintain the temperature at about 160 C. for about six hours. Cumene is then distilled oif to allow the temperature to rise to about C. and the mixture is held at that temperature for about one hour to remove cumene. The resulting product can be added to lubricating oil to dispense sludgeforming materials.
In like manner, good results are obtained using ASAs derived by the polymerization of other ole-fins such as propylene, isobutylene, n-pentene and isopentene. Likewise, other tertiary amines which contain both a hydroxyalkyl and a cyanoalkyl substituent can be profitably employed.
The detergent-dispersants of this invention are effective in both hydrocarbon and synthetic diester lubricating oils, including lubricating oils used in spark-ignition engines and diesel engine lubricants. To prepare oil compositions of this invention an appropriate quantity, from about 0.01 to about 10 Weight percent, and preferably from '1 to 5 weight percent, of a detergent-dispersant product of this invention is blended with the base oil. Suitable base oils include petroleum-derived hydrocarbon mineral oils and also synthetic diester oils, such as sebacates, adipates, silicones, halogen containing organic compounds including the fluorocarbons, etc, polyalkylene glycol lubricants and organic phosphites which are suitable as lubricants.
EXAMPLE 4 Product from Example 2: Cone (wt. percent) A 0.01 B 0.1 C l D 2 E 5 F 7 G 10 EXAMPLE 5 Lubricating oils are prepared as in Example 4 by blending the listed oil with the products prepared in Example 2. (A) A dioctyl sebacate having a viscosity at 210 F. of
36.7 SUS, a viscosity index of 159 and a molecular weight of 426.7.
(B) A di-(sec-amyl) sebacate having a viscosity at 210 F. of 33.8 SUS, a viscosity index of 133 and a molecular weight of 342.5.
(C) A di-(Z-ethylhexyl) sebacate having a viscosity at 210 F. of 37.3 SUS, a viscosity index of 152 and a molecular weight of 426.7.
(D) A di-(2-ethylhexyl) adipate having a viscosity at 210 F. of 34.2 SUS, a viscosity index of 121 and a molecular weight of 370.6.
(E) A diisooctyl azelate having a kinematic viscosity of 3.34 centistokes at 65 R, an ASTM slope from-40 F. to 210 F. of 0.693, a pour point of -85 F., a flash 7 point of 425 F. and a specific gravity at 25 F. of 0.9123. (F) A diisooctyl adipate having a viscosity at 210 F. of 35.4 SUS, a viscosity at 100 F. of 57.3 SUS, a viscosity of 3,980 SUS at 40 F. and a viscosity index of 143.
I claim:
1. An ashless lubricant dispersant comprising the reaction product of:
(A) one mole part of a succinic acid generating reactant selected from the group consisting of alkenyl succinic acid and alkenyl succinic anhydride wherein the alkenyl portion has a molecular weight of from 700 to 1600 with (B) from about 0.6 to 3 mole parts of a tertiary amine having the formula:
wherein n is an integer from 1-2, m is an integer from 1-2, the sum of n plus in is 2-3, R and R are divalent hydrocarbon radicals containing 2-5 carbon atoms, and R is an alkyl radical containing from 1 to about 18 carbon atoms; said reaction being carried out at a temperature of from about 100 to 200 C.
2. The composition of claim 1 wherein said succinic acid generating group is an alkenyl succinic anhydride wherein the alkenyl radical is derived from the polymerization of a monoolefin containing 25 carbon atoms such that said alkenyl radical has a molecular weight of from about 700 to 1600.
3. The composition of claim 2 wherein said alkenyl radical is derived from a polybutene having a molecular Weight of from 800 to 1400 and wherein said tertiary amine is 3-[bis(2-hydroxyethyl)amino1propionitrile.
4. A lubricating oil containing a dispersant amount of the composition of claim 1.
5. A lubricating oil containing from 0.01 to 10 weight percent of the composition of claim 2.
6. A hydrocarbon lubricating oil containing from 0.01 to about 10 weight percent of the composition of claim 3.
References Cited UNITED STATES PATENTS 3,219,666 11/1965 Norman et al. 252-515 3,272,746 9/1966 Le Suer et a1. 252-51.5
DANIEL E. WYMAN, Primary Examiner.
PATRICK P. GARVIN, Examiner.
Claims (2)
1. AN ASHLESS LUBRICANT DISPERSANT COMPRISING THE REACTION PRODUCT OF: (A) ONE MOLE PART OF A SUCCINIC ACID GENERATING REACTANT SELECTED FROM THE GROUP CONSISTING OF ALKENYL SUCCINIC ACID AND ALKENYL SUCCINIC ANHYDRIDGE WHEREIN THE ALKENYL PORTION HAS A MOLECULAR WEIGHT OF FROM 700 TO 1600 WITH (B) FROM ABOUT 0.6 TO 3 MOLE PARTS OF A TERTIARY AMINE HAVING THE FORMULA:
4. A LUBRICATING OIL CONTAINING A DISPERSANT AMOUNT OF THE COMPOSITION OF CLAIM 1.
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US7947636B2 (en) | 2004-02-27 | 2011-05-24 | Afton Chemical Corporation | Power transmission fluids |
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US3219666A (en) * | 1959-03-30 | 1965-11-23 | Derivatives of succinic acids and nitrogen compounds | |
US3272746A (en) * | 1965-11-22 | 1966-09-13 | Lubrizol Corp | Lubricating composition containing an acylated nitrogen compound |
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US3219666A (en) * | 1959-03-30 | 1965-11-23 | Derivatives of succinic acids and nitrogen compounds | |
US3272746A (en) * | 1965-11-22 | 1966-09-13 | Lubrizol Corp | Lubricating composition containing an acylated nitrogen compound |
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US7947636B2 (en) | 2004-02-27 | 2011-05-24 | Afton Chemical Corporation | Power transmission fluids |
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