US3442808A - Lubricating oil additives - Google Patents

Lubricating oil additives Download PDF

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Publication number
US3442808A
US3442808A US591084A US3442808DA US3442808A US 3442808 A US3442808 A US 3442808A US 591084 A US591084 A US 591084A US 3442808D A US3442808D A US 3442808DA US 3442808 A US3442808 A US 3442808A
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Prior art keywords
mannich
oil
lubricating oil
grams
additives
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Thornton P Traise
Randel Q Little
Roger W Watson
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Standard Oil Co
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Standard Oil Co
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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
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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
    • C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
    • C10M159/12—Reaction products
    • C10M159/16—Reaction products obtained by Mannich reactions
    • 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
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    • 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
    • C10M2207/027—Neutral salts thereof
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    • 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
    • C10M2207/028—Overbased salts thereof
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
    • C10M2207/123—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms polycarboxylic
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/22—Acids obtained from polymerised unsaturated acids
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
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    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/283—Esters of polyhydroxy compounds
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/286—Esters of polymerised unsaturated acids
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—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
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
    • C10M2209/084—Acrylate; Methacrylate
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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
    • C—CHEMISTRY; METALLURGY
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    • 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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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/08—Amides [having hydrocarbon substituents containing less than thirty carbon atoms]
    • C—CHEMISTRY; METALLURGY
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/08—Amides [having hydrocarbon substituents containing less than thirty carbon atoms]
    • C10M2215/082—Amides [having hydrocarbon substituents containing less than thirty carbon atoms] containing hydroxyl groups; Alkoxylated derivatives
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/086—Imides [having hydrocarbon substituents containing less than thirty carbon atoms]
    • C—CHEMISTRY; METALLURGY
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
    • C10M2215/26—Amines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
    • C10M2215/28—Amides; Imides
    • C—CHEMISTRY; METALLURGY
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    • 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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    • 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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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
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    • C10M2219/046—Overbased sulfonic acid salts
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    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
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    • C10M2223/04—Phosphate esters
    • C10M2223/045—Metal containing thio derivatives
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    • C10N2070/00—Specific manufacturing methods for lubricant compositions
    • C10N2070/02—Concentrating of additives

Definitions

  • This invention concerns new chemical compositions and lubricating oil compositions containing the same.
  • the subject matter of the instant invention also concerns a novel class of chemical compositions which act as dispersants when incorporated as additives into engine lubricating oils.
  • the invention particularly concerns new Mannich condensation products.
  • the prior art portrays a need for improved engine lubricating oil additives which function as dispersants to retain in suspension insoluble particles such as the products of fuel combustion, those of incipient oxidation, and those of lubricant deterioration.
  • the control of the deterioration of lubricating oils has long been a problem particularly in the formulation of the compositions of lubricating oil additives.
  • additives in lubricating oils chemical compositions which tend to reduce oil deterioration and the consequent formation of the sludge and varnish-like materials.
  • corrosion and oxidation inhibitors and dispersing agents. These additives generally function to reduce the corrosion of the surfaces to be protected, to stabilize the lubricating oil, to inhibit deterioration by oxidation, and to function as dispersants which tend to prevent the agglomeration of sludge and the deposition of varnish and sludge caused by the formation of the products of deterioration.
  • Another object of this invention is to provide lubricating oil dispersants which have improved solubility in said oil and which exhibit superior compatibility with other oil included additives.
  • An additional object of this invention is to provide a novel process for the preparation of compositions useful as dispersants.
  • Another object of this invention is to provide improved lubricating compositions.
  • Mannich condensation products is appreciably improved by reacting the Mannich products with a polyalkenyl succinic anhydride at a temperature sufficient to remove water of condensation.
  • the modified Mannich reaction products impart excellent dispersant properties to the lubricating oil compositions while maintaining an unusually high degree of solubility within said lubricating oil compositions.
  • the invention includes the reaction of an alkylphenol, formaldehyde, and a polyalkylene amine to form a Mannich product.
  • the ratio of phenol, formaldehyde, and amine is from about l:1:0.5 to about 1:2.522.
  • the conventional Mannich product so formed is known to have anti-wear and oxidation-inhibiting properties but limited oil solubility.
  • This conventional Mannich product is then reacted with a polyalkenyl succinic anhydride to yield the highly effective low-temperature dispersants for lubricating oils.
  • the Mannich polyalkenyl succinic an hydride reaction product can be treated with a small amount of a boron-containing compound to provide an other modified Mannich reaction product. Boration further improves compatibility with other additives.
  • Each of these products exhibits surprising and superior dispersant properties when incorporated into lubricating oils.
  • Each of these products also maintains a high degree of solubility with the lubricating oil additive-containing matrix.
  • polyalkenyl succinic anhydride is meant the reaction product of maleic anhydride with a polymer of a monoolefin having three or four carbon atoms, such as propylene or butylene.
  • the polymers should be a viscous liquid polyolefin having a viscosity measured in Saybolt Universal Seconds (SUS) at 210 F. of from about 50 sec. to about 10,000 sec.
  • SUS Saybolt Universal Seconds
  • Such viscous liquid polypropylenes and polybutylenes (including polyisobutylenes) are well known to those skilled in the art and they can be conveniently prepared, for example, by polymerizing propylene-and-butylene containing hydrocarbon fractions in the presence of aluminum chloride or other Friedel- Crafts catalysts.
  • viscous liquid polypropylenes and polybutylenes contain a limited amount of residual unsaturation so that they can be reacted with maleic anhydride to form an alkenyl succinic anhydride.
  • These polypropylenes and polybutylenes can be reacted with substituted maleic anhydrides with other anhydrides of similar unsaturated aliphatic dicarboxylic acids to form corresponding alkenyl derivatives.
  • a polybutenyl succinic anhydride can be prepared by reacting about 0.85 mole of maleic anhydride per mole of polybutene, the polybutene having a molecular weight of about 860. Although not all of the maleic anhydride enters into the reaction at about 450 F., only about 5 weight percent is thermally decomposed and a small amount is stripped out. The yield of polybutenyl succinic anhydride is about 50-80% based on the polybutene used.
  • Suitable Mannich products for modification according to the process of this invention are prepared by condensing an alkylphenol, formaldehyde, and a polyalkylene amine.
  • the alkylphenol may be a C -C alkyl substituted phenol, preferably a C alkyl substituted phenol (nonylphenol).
  • the polyalkylene polyamine is derived from ethylenediamine or condensation products of ethylenediamine, such as diethylene triamine, triethylene tetramine, tetraethylenepentamine, or pentaethylene hexamine.
  • Tetraethylenepentamine TEPA is the preferred polyalkylene polyamine.
  • Example I Preparation of conventional Mannich product
  • the preparation of a conventional Mannich product is a condensation of TEPA with nonylphenol and formaldehyde.
  • Three thousands three hundred twenty nine lbs. of TEPA, 17.6 lb. moles, is added to a 2,000 gallon kettle blanketed with an inert gas such as nitrogen.
  • an inert gas such as nitrogen.
  • One thousand nine hundred thirty six lbs. of nonylphenol is added over a 30-minute period with thorough mixing and the temperature is adjusted to within the range of about 100-110 F.
  • One thousand four hundred twenty five lbs. of 37% aqueous formaldehyde containing 17.6 lb. moles of CH O is charged to the above mixture over a period of about three hours. The temperature will rise to about 130-150 F.
  • the reacting material is held for about two hours with stirring. Subsequently, the reactants are heated to about 300 F. in the presence of an inert gas such as nitrogen and about 145 gallons of water is distilled therefrom. The reacting material is held at 300 F. for about one hour prior to cooling to ambient temperature.
  • an inert gas such as nitrogen
  • Example III Alkylenyl succinimide modified Mannich About 648 grams (6 moles) of para cresol and 2270 grams (12 moles) tetrae-thylenepentamine were combined in a 5-liter flask equipped with a stirrer. About 972 grams of 37% formaldehyde (12 moles) were added over a period of four hours. The exothermic heat increased the reaction temperature to about 133 F. The product was then heated between about 311 F. and 327 F. with nitrogen blowing over a period of about ten hours. A total of about 570 ml. of water were distilled out. The product yield was 3000 grams.
  • Example IV -Alkylenyl succinimide modified Mannich 648 grams (6 moles) of mixed cresol were placed in a 5-liter flask equipped with a stirrer. Through a dropping funnel, 2270 grams (12 moles) of tetraethylenepentamine was added. A small exothermic heat was observed. 972 grams (12 moles) of 37% formaldehyde was added dropwise. The mixture was heated between about l22-302 F. for 16 hours with nitrogen blowing. 345 ml. of water were condensed in a trap. The yield of product was 3121 grams. The nitrogen content was 25%.
  • the polyalkyleneyl succinic anhydride modification of the above Mannich was prepared as follows. 382.5 grams of the above Mannich (.75 mole) was added to a mixture of 2580 grams of 54% active polybutenyl succinic anhydride containing a polybutenyle substituent having a viscosity of about 1000 SUS at 210 F. (1.5 moles) and 564 grams of S-gnade oil in a 5 -liter flask. The mixture was heated with nitrogen blowing for about ten hours between about 77 and 302 F. The yield of product was 3452 grams and contained 2.70% nitrogen.
  • Example V-Alkyleneyl succinimide modified Mannich Phenol was alkylated with polypropylene as follows. About 1600 grams (2 moles) of polypropylene, l-liter of hexane and 210 grams of a phenol-B1 complex (about 2 moles) were reacted in a 5-liter flask at ambient temperatures for approximately two hours. The product was washed with water and steam stripped to about 302 F., then dried by blowing with an inert gas. The yield was 1657 grams, the molecular weight 885, and the hydroxyl number was 51.
  • the Mannich product of the above phenol was prepared as follows. 1600 grams of the alkyl phenol (1.8 moles) and 681 grams of tetraethylenepentamine (3.6 moles) were combined in a 5-liter flask equipped with a stirrer. About 294 grams of 37% formaldehyde (3.6 moles) were added dropwise. The mixture was heated with stirring for about ten hours between about 122 and 144 F. About 170 mls. of water were collected in a trap. The yield was 2222 grams.
  • the succinimide of the above Mannich was prepared as follows. About 1000 grams of the Mannich (.772 mole) was dissolved in 100 mls. of toluene and added dropwise to 2660 grams of a polybutenyl succinic anhydride containing a polybutenyl substituent having a viscosity of about 1000 SUS at 210 F. (1.54 moles) heated to about 257 F. in a 5-liter stirred flask. The mixture was heated with nitrogen gas blowing for about ten hours at about 25 7-302 F. The yield was 3623 grams. The product contained 2.78% nitrogen.
  • R is a polyolefin constituent derived from a mono-olefin having three to four carbon atoms, preferably a polybutylene having a viscosity at 210 F. of from about 50 to 10,000 SUS: n equals 0-10, preferably about 3; and R and R are hydrogen or a 0 -0 alkyl-substituent, preferably, R being hydrogen and R being C
  • the aforementioned boron modification of the modified Mannich product may be carried out with boric acid, a boric acid ester, a boric anhydride, etc., at a temperature of from about 120-400" F., using from 0.2 to 2.0 or more moles of boron per mole of modified Mannich reaction product.
  • B/ N boron to nitrogen
  • Lubricating oils containing Mannich condensation products in accordance with this invention were tested in the Lincoln M.S. V Test Sequence designed by Ford Motor Company.
  • the Lincoln Sequence test procedure evaluates low temperature dispersancy characteristics of a lubricating oil. Briefly, the test consists of using the oil to be tested as a lubricating oil in a V-8 Lincoln engine under prescribed test conditions. Accordingly, 5 quartes of oil are placed in the crankcase and the engine is started and run in accordance with the 4-hour cycle:
  • the 4-hour cycle is repeated a total of 48 times (192 hours running time). After each 16 hours of operation the engine is shut down for 8 hours. The oil level is adjusted with fresh oil to a level of 5 quarts. At the termination of the test, the hot oil is drained. The engine is then disassembled and examined for deposits of varnish and sludge among other observable results.
  • the rating of total sludge is the sum of the average ratings for the eight classes of parts multiplied by /s since the perfect total sludge rating is 50.
  • the perfect total varnish rating is also 50.
  • the blend of additives included 3.75% of the Mannich condensation product made in accordance with the teachings of EXAMPLE II and was combined with 1.0% of an overbased magnesium sulfonate that is readily available commercially and 1% of a zinc dialkyldithio-phosphate oxidation inhibitor also commercially available.
  • the third formulation included 2.5% by weight of the novel dispersants of this invention and the other additives of formulations 1 and 2 were present in the same amounts. All three tests were effective in demonstrating the high performance of the novel dispersant additive as shown below in Table I.
  • formulations Nos. 6 and 7 ingredients were added to a SAE 30 lubricating oil.
  • the additives included 5% of the novel dispersant, 1% of an devisbased calcium sulfonate and 1% of a zinc dialkyldithiophosphate.
  • the combination of additives in formulation 7 included 6.0% of the novel dispersant of this invention, 4% basic calcium phenate, 2% of an overbased calcium sulfonate and 1% of a zinc dialkyldithio-phosphate. All the constituents except the novel dispersant of this invention are readily available on the open market. The test results of these formulations were effective in demonstrating the superiority of the novel dispersants as shown in Table II below.
  • the dispersants prepared as disclosed herein can be used as addition agents in lubricating oils and especially in lubricating oils for use in internal combusion engines.
  • the addition agents impart excellent low temperature dispersancy characteristics to the lubricating oil.
  • amounts of the dispersancy addition agent may be varied as desired, it is believed advantageous to use at least about 0.2 weight percent and up to 20 weight percent of the addition agent of this invention and preferably 0.5 to 10 weight percent in a suitable lubricating oil.
  • the preferred lubricating oils are the mineral lubricating oils, the use of the additive compositions is not restricted thereto.
  • lubricating oil bases can be used, such as hydrocarbon oils, both natural and synthetic, for example, those obtained by the polymerization of olefins, as well as synthetic lubricating oils of the alkylene oxide type and the monoand polycarboxylic acid ester type, such as the esters of adipic acid, sebacic acid, azelaic acid; it is also contemplated that various other well-known additives, such as anti-oxidants, anti-foam agents, pour point depressors, extreme pressure agents, corrosion inhibitors, anti-wear agents, etc., may be incorporated in lubricating oils containing the additives of our invention.
  • additives such as anti-oxidants, anti-foam agents, pour point depressors, extreme pressure agents, corrosion inhibitors, anti-wear agents, etc.
  • Concentrates of a suitable oil base containing more than 10 percent, for example, up to 75 percent or more, of the additive of this invention alone or in combination with other additives may be prepared and can be used for blending with hydrocarbon oils or other oils in the proportions desired for the particular conditions of use to give a finished lubricating product containing the additives of this invention.
  • examples of formulated lubricating oils containing such reaction products were prepared.
  • a composition comprising the reaction product of heating to a temperature sufficient to remove water of condensation, a Mannich compound obtained by condensing an alkyl substituted phenol, formaldehyde and a polyalkylene polyamine with 1-2 moles of alkenyl succinic anhydride, said alkenyl substituent being derived from a polyolefin having a viscosity at 210 F. of from about $0 to about 10,000 Saybolt Universal Seconds.
  • composition of claim 1 reacted at a temperature of from about -400 F. with a small amount of boron containing compound selected from the group consisting of boric acid, boric acid esters and boric anhydride, in a mole ratio of from 0.2 to at least 2.0 moles of boron per mole of said composition of claim 1.
  • composition of claim 1 wherein the phenol is a mono-substituted phenol.
  • composition of claim 1 wherein the phenol is a di-alkyl substituted phenol.
  • a lubricant composition comprising a major proportion of a lubricating oil and from about 0.2-20% by wt. of the composition of claim 1.
  • composition of claim 1 wherein the alkenyl substituent is a polybutene having a molecular weight within the range of about BOO-10,000.
  • a composition comprising the reaction product of heating to a temperature of from about 77 F. to about 302 F. a Mannich compound obtained by condensing a nonylphenol, formaldehyde and tetraethylenepentamine with l-2 moles of alkenyl succinic anhydride, said alkenyl substituent being derived from a polyolefin having a viscosity at 210 F. of from about 50 to about 10,000 Saybolt Universal Seconds.
  • composition of claim 7 reacted at a temperature of from about 120-400 F. with a small amount of boron containing compound selected from the group consisting of boric acid, boric acid esters and boric anhydride, in a mole ratio of from 0.2 to at least 2.0 moles of boron per mole of said composition of claim 7.
  • a lubricant composition comprising a major proportion of a lubricating oil and from about 0.2-20% by wt. of the composition of claim 8.
  • a composition comprising the reaction product of heating to a temperature of from about 77 F. to about 302 F., a Mannich compound obtained by condensing a cresol, formaldehyde, and tetraethylenepentamine with l-2 moles of alkenyl succinic anhydride, said alkenyl substituent being derived from a polyolefin having a vis cosity at 210 F. of from about 50 to about 10,000 Saybolt Universal Seconds.
  • a lubricant composition comprising a major proportion of a lubriacting oil and from about 0.2-20% by wt. of the composition of claim 10.
  • a process for producing a lubricant additive composition comprising the steps of reacting about 2 moles of alkenyl succinic anhydride, said alkenyl substituent being derived from a polyolefin having a viscosity of 210 References Cited UNITED STATES PATENTS Le Suer 25249.6 Norman et a1. 2525 1.5 Le Suer 25249.6 Le Suer et a1 25251.5 Le Suer 25251.5

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