US3798247A - Oil soluble aliphatic acid derivatives of molecular weight mannich condensation products - Google Patents

Oil soluble aliphatic acid derivatives of molecular weight mannich condensation products Download PDF

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Publication number
US3798247A
US3798247A US00054558A US3798247DA US3798247A US 3798247 A US3798247 A US 3798247A US 00054558 A US00054558 A US 00054558A US 3798247D A US3798247D A US 3798247DA US 3798247 A US3798247 A US 3798247A
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molecular weight
acid
oil
high molecular
mole
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E Piasek
R Karll
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BP Corp North America Inc
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Standard Oil Co
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    • C10M159/12—Reaction products
    • C10M159/16—Reaction products obtained by Mannich reactions
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    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/046—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for traction drives
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C10N2040/251—Alcohol-fuelled engines
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C10N2040/255—Gasoline engines
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C10N2040/255—Gasoline engines
    • C10N2040/28—Rotary engines

Definitions

  • This invention relates to improved lubricating oils and particularly concerns automobile and diesel crankcase lubricating oil formulations containing a minor amount of a new class of oil-soluble addition agents which improve the performance of the oil, particularly its dispersantdetergent function thus enabling lubricating oils to provide a high degree of protection of the lubrication parts of internal combustion engines.
  • crankcase lubricating oils present-day automobile and diesel engines have been designed for higher power output, lower combustion products emission and longer in-service periods of use of crankcase lubricating oils. These design changes have resulted in such severe operating conditions as to necessitate devising higher efiiciency lubricating oils that will, under the increased severity of in-service use, afford proper prot ction against corrosion and the accumulation or deposition of sludge, varnish and resinous materials on the surface of engine parts which rapidly accelerate decrease in both operating efficiency and life of the engine.
  • the principal ingredient of crankcase lubricants is a base lubricating oil, a mixture of hydrocarbons derived from petroleum.
  • a lubricant base oil Even when highly refined by removal of deleterious components, such as polymerizable components, acid formers, waxes, etc., a lubricant base oil still requires the addition of a number of oil-soluble chemical additives to enable the oil to resist oxidation, deposition of sludge and varnish on, and corrosion of, the lubricated metal parts, and to provide added lubricity and regulated viscosity change from low to high temperature. These ingredients are commonly known as anti-oxidants, dispersantdetergents, pour point dispersants, etc.
  • Combustion products from the burning of fuel and thermal degradation of lubricating oils and addition agents tend to concentrate in the crankcase oil with the attendant formation of oil-insoluble deposit-forming products, that either surface coat the engine parts (varnish or lacquer-like films) or settle out on the engine parts as viscous (sludge) deposits or form solid ash-like or carbonaceous deposits. Any of such deposits can restrict, and even plug, grooves, channels and holes provided for lubricant flow to the moving surfaces of the engine requiring lubrication thus accelerating the wear and thus reducing the efiiciency of the engine. In addition, acidic combustion products corrode the lubricated metal surfaces.
  • crankcase oil formulations not only to reduce thermal decomposition of the oil and addition agents (antioxidants) but also to keep in suspension (as a dispersant) and to resuspend (as a detergent) insoluble combustion and degradation products as well as to neutralize acidic products (anti-corrosion agents).
  • a separate additive is usually added for each improvement to be effected.
  • R is a divalent alkylene hydrocarbon radical and R is an alkyl group containing from 2 to 20 carbon atoms.
  • Still others have been prepared by reacting C -C alkylphenols, formaldehyde and alkylene polyamines of the formula wherein A is a divalent alkylene radical of 2 to 6 carbon atoms and n is an integer from 1 to 10, in the ratio of from 0.5 to 2 moles each of C -C alkylphenol and formaldehyde for each nitrogen group contained in the alkylene polyamine reagent.
  • the molar reactant ratio range of C -C alkylphenol, amine and formaldehyde used to form such products is 1-20: 1.0: 1-20.
  • US. Pat. No. 3,036,- 003 exemplifies such products, which usually are formed with ethylene polyamines, according to the above formula in which A is CH CH and n is 2, 3 and 4.
  • an inert stripping gas such as nitrogen, carbon doxide, etc.
  • the exactly neutralized or overbased alkaline earth metal salts (alkaline earth metal phenates) of those prior low molecular weight Mannich condensation products have been suggested for use in providing lubricating oils with a combination of detergent-inhibitor properties in one addition agent.
  • the exactly neutralized alkaline earth metal salts have one equivalent of alkaline earth metal for each hydroxy group present.
  • the overbased salts have, for each hydroxy group present, more than one equivalent of alkaline earth metal in the form of a hydroxy metaloxy, alkoxy metaloxy and even alkaline earth metal carbonate complex with hydroxy metaloxy on each benzene group as a replacement for the phenol hydroxy group.
  • said addition agents form objectionable metal ash deposits and have other performance deficiencies.
  • an aliphatic acid having suitably from about 6 carbon atoms to about 30 carbon atoms, desirably at least 10 carbon atoms and preferably 16 or more carbon atoms per carboxylic acid group.
  • the aliphatic acid can be used as an initial reactant, reacted with the hazy high molecular weight Mannich condensation product before its filtration or added to the filtered product before it goes to storage.
  • Such uses of the aliphatic acid require only small amounts, in the range of 0.1-10.0 weight percent to eliminate those drawbacks and provide an improved product.
  • This invention pertains to a new class of compounds useful as multifunctional addition agents for lubricating oils, particularly such oils used in internal combustion engines in which they function as highly eflicient dispersant-detergent and oxidation inhibitor agents.
  • the new class of compounds which comprise our invention are oil-soluble high molecular aliphatic acid modified weight Mannich condensation products. They can be prepared either by condensing in the usual manner under Mannich-Reaction conditions:
  • An alkyl-substituted hydroxyaromatic compound whose alkyl-substituent has a 600-l00,000 fin, preferably a polyalkylphenol whose polyalkyl substituent is derived from l-mono-olefin polymers having a fin of about 850-2500;
  • An amine containing at least one NH group preferably an alkylene polyamine of the formula wherein A is a divalent alkylene radical having 2 to 6 carbon atoms and x is an integer from 1 to 10; and
  • aldehyde preferably formaldehyde followed by reaction with (4) aliphatic acid before or after filtration. Or they can be prepared by using all four reactants at one time under the general Mannich Reaction conditions.
  • the foregoing high molecular weight products of this invention are preferably prepared according to the conventional methods heretofore employed for the preparation of Mannich condensation products, using the abovenamed reactants in the respective molar ratios of high molecular weight alkyl-substituted hydroxyaromatic compound, amine, aldehyde and aliphatic acid of approximately 1.0:0.1-l:1.0-10:0.014-1.0.
  • Suitable as a condensation procedure involves adding at a temperature of from room temperatures to about 200 F. the formaldehyde reagent (e.-g.
  • the preferred additives according to this invention are high molecular weight bis-Mannich condensation products formed by reacting (1) a 850-2500 Mn polyalkylphenol; (2) an ethylene polyamine, as amine reactant; (3) formaldehyde and (4) an aliphatic acid in the respective molar ratio of 1.0:0.7-1.0:1.5-2.1:0.014-0.62.
  • novel addition agents according to our invention are the high molecular weight aliphatic acid modified Mannich condensation products of 1) high molecular weight alkyl-substituted phenol whose alkyl substituent has a fin of GOO-100,000, a compound having at least one HN group, an aldehyde and an aliphatic acid wherein the respective molar ratio of the reactants is l.0:0.1-10:l.0-l0:0.0l40.62.
  • Preferred addition agents are those obtained by condensing (1) an alkylphenol whose alkyl substituent is derived from l-mono-olefin polymers having a 850-2500 Mn; (2) an alkylene polyamine having the formula H N(A--NH),,H wherein A is a divalent saturated hydrocarbon radical having 2 to 6 carbon atoms and n is an integer from 1 to 10, (3) a formaldehyde yielding reactant and (4) an aliphatic acid having 10-20 carbon atoms per carboxylic acid group used in the respective molar ratio of reactants is 1:0.7- 1.0:1.5-2.1:0.014-0.62.
  • the high molecular weight products of this invention are exceptionally useful addition agents for lubricating oils imparting thereto dispersant-detergent and anti-oxidant properties at relatively low concentrations of the addition agent, e.g., 0.05 to 10 weight percent in formulated crankcase lubricating oil. Higher concentrations, e.g., 10 to 70 weight percent, are useful concentrates of the preparation of those formulated crankcase lubricating oils and the fortification of crankcase oil in use prior to the scheduled complete drain.
  • High molecular weight alkyl-substituted hydroxyarornatics are polypropylphenol, polybutylphenol and other polyalkylphenols. These polyalkylphenols may be obtained by the alkylation, in the presence of an alkylating catalyst, such as BF of phenol with high molecular weight polypropylene, polybutylene and other polyalkylene compounds to give alkyl substituents on the benzene ring of phenol having an average GOO-100,000 fin.
  • an alkylating catalyst such as BF of phenol with high molecular weight polypropylene, polybutylene and other polyalkylene compounds to give alkyl substituents on the benzene ring of phenol having an average GOO-100,000 fin.
  • the 600 fin and higher fin alkyl-substituents on the hydroxyaromatic compounds may be derived from high molecular weight polypropylenes, polybutenes and other polymers of mono-olefins, principally l-mono-olefins. Also useful are copolymers of mono-olefins with monomers copolymerizable therewith wherein the copolymer molecule contains at least by weight, of monoolefin units. Specific examples are copolymers of butenes (butene-l, butene-2 and isobutylene) with monomers copolymerizable therewith wherein the copolymer molecule contains at least 90%, by weight, of propylene and butene units, respectively.
  • Said monomers copolymerizable with propylene or said butenes include monomers containing a small proportion of unreactive polar groups such as chloro, bromo, keto, ethereal, aldehyde, which do appreciably lower the oil-solubility of the polymer.
  • the comonomers polymerized with propylene or said butenes may be aliphatic and can also contain non-aliphatic groups, e.g.,
  • others which may be used include those which have been used to prepare prior low molecular weight Mannich condensation products, e.g., high molecular weight alkyl-substituted derivatives of resorcinol, hydroquinone, cresol, catechol, xylenol, hydroxy diphenyl, benzylphenol, phenethylphenol, naphthol, tolylnaphthol, among others.
  • Mannich condensation products e.g., high molecular weight alkyl-substituted derivatives of resorcinol, hydroquinone, cresol, catechol, xylenol, hydroxy diphenyl, benzylphenol, phenethylphenol, naphthol, tolylnaphthol, among others.
  • Preferred for the preparation of the before mentioned preferred bis Mannich condensation products are the polyalkylphenol reactants, e.g., polypropylphenol and polybutylphenol whose alkyl group has an average number molecular weight of 600-3000, the most preferred being polybutylphenol whose alkyl group has an average number molecular weight of 850-2500.
  • polyalkylphenol reactants e.g., polypropylphenol and polybutylphenol whose alkyl group has an average number molecular weight of 600-3000, the most preferred being polybutylphenol whose alkyl group has an average number molecular weight of 850-2500.
  • HN group containing reactants Representative of this class of reactants are alkylene polyamines, principally polyethylene polyamines.
  • Other representative organic compounds containing at least one HN group suitable for use in the preparation of Mannich condensation products are well known and include the mono and di-amino alkanes and their substituted analogs, e.g., ethylamine and diethanol amine; aromatic diamines, e.g., phenylene diamine, diamino naphthalenes; heterocyclic amines, e.g., morpholine, pyrrole, pyrrolidine, imidazole, imidazolidine, and piperidine; melamine and their substituted analogs.
  • Suitable alkylene polyamide reactants include ethylenediamine, diethylene triamine, triethylene tetramine, tetraethylene pentamine, pentaethylene hexamine, hexaethylene hepta-amine, heptaethylene octamine, octaethylene nonamine, nonaethylene decamine and decaethylene undecamine and mixture of such amines having nitrogen contents corresponding to the alkylene polyamines, in the formula H N(A-NH),,H, mentioned before, A is divalent ethylene and n is l to of the foregoing formula.
  • propylene polyamines such as propylene diamine and di-, tri-, tetra-, penta-propylene tri-, tetra-, pentaand hexa-arnines are also suitable reactants.
  • the alkylene polyamines are usually obtained by the reaction of ammonia and dihalo alkanes, such as dichloro alkanes.
  • the alkylene polyamines obtained from the reaction of 2 to 11 moles of ammonia with 1 to 10 moles of 'dichloro alkanes having 2 to 6 carbon atoms and the chlorines on dififerent carbons are suitable alkylene polyamine reactants.
  • Aldehyde reactants Representative of this aldehyde class of reactants for use in the preparation of the high molecular products of this invention include the aliphatic aldehydes such as formaldehyde (also as paraformaldehyde and formalin), acctaldehyde and aldol (b-hydroxybutyraldehyde). We prefer to use formaldehyde or a formaldehyde yielding reactants.
  • Aliphatic acid reactants The aliphatic acid reactant of this invention has a carbon atom content of a total (including the carbon of the canboxylic acid group) of from about six to about 30 and consists of the alkanoic (satu rated) and alkenoic (mono-unsaturated) acids. The upper limit of the carbon content is restricted only by the largest carbon atom content of such acids available or capable of feasible preparation.
  • Such aliphatic acids can be natural and synthetic mono-, di and tri-carboxylic acids. Suitable natural aliphatic acids are the natural fatty acids obtainable by known hydrolysis (acid and alkaline) of vegetable and animal oils and fats and wax esters.
  • Suitable synthetic acids can be derived from oxidation of the alcohol moiety of the wax ester where such alcohol moiety has at least six carbon atoms; from the polymerization of unsaturated natural acids having two or three carbon to carbon double bonds (dimer and trimer acids) and the hydrogenation of residual carbon to carbon double bonds in such polymer acids.
  • the polymer acids obtained from oleic acid, euric acid, linoleic acid and linolenic acid and other unsaturated acids; and from oxidation or other reactions of polypropenes and polybutenes (e.g. polyisobutenes) which introduce one or more carboxylic acid group on the polymer chain.
  • oxidation stability test (Union Pacific Oxidation Test) there are tested oil formulations containing equivalent amounts of high molecular weight Mannich Product (a polybutyl-, hydroxybenzyl-substituted tetraethylene pentamine having a number average molecular weight of 3600) and the same Mannich Product modified with 0.125 mole (0.8 weight percent) of each of oleic acid, isostearic acid, a mixture of C and C monounsaturated alkenoic acids and a mixture of C and C saturated alkanoic acids.
  • Mannich Product a polybutyl-, hydroxybenzyl-substituted tetraethylene pentamine having a number average molecular weight of 3600
  • Mannich Product modified with 0.125 mole (0.8 weight percent) of each of oleic acid, isostearic acid, a mixture of C and C monounsaturated alkenoic acids and a mixture of C and C saturated alkanoic acids.
  • Pentane insolu- Additive Acid modifier bles, gms.
  • Suitable alkanoic acids having 6 or more total carbon atoms are those obtainable from the glycerides: vegetable oils and animal fats and the wax esters by the known hydrolysis or saponification-acidification or acid treatment processing of said oil and fat glycerides and the wax esters (i.e. natural waxes), the oxidation of the mono-alcohol obtainable from the simple ester of the wax esters and known acid synthesis.
  • suitable alkonic acids i.e.
  • R groups of 6 to 30 carbon atoms include caproic acid, caprylic acid, capric acid, hendecylic acid, lauric acid, tridecylic acid, myristic acid, pentadecylic acid, palmitic acid, margaric acid, stearic acid, nonadecylic acid, arachidic acid, medullic acid, behenic acid, lignoceric acid, pentacosoic acid, cerotic acid, heptacosoic acid, monocosoic acid, montanic acid, and melissic acid.
  • alkanoic acids are obtained first in mixtures of two, three or more alkanoic acids of different carbon contents from said glycerides and wax esters said mixtures can be used in this invention in place of a single alkanoic acid reactant.
  • said mixtures of alkanoic acids also contain unsaturated acids it is preferred that such mixture of acids be reduced to a product which is substantially free of unsaturation.
  • Suitable alkenoic acids having a total of at least six carbon atoms include those from hexenoic, heptenoic, octenoic, etc. acids up to oleic (C and erucic (C acids. Also suitable are the dimer acid of linoleic and its saturated dimer analog; dimer and trimer acids of linolenic acid and the saturated dimer and trimer analogs. Other polymeric acids, e.g. co-dimers of oleic and linoleic or linolenic acids and the saturated analogs of those dimer acids are also suitable.
  • Such enhancement is achieved with relatively small amounts of the aliphatic acid relatively small, for example in the range of 0.01 to 0.03 mole aliphatic acid per mole of high molecular Weight alkyl-substituted hydroxy aromatic compound before described as reactant (1).
  • H N- and HN groups are separated by two or three carbon atoms as in molety derived from ethylene diamine, ethyl- (e.g. stearic wherein R has 17 carbon atoms) and N-(2- hydroxy--polybutylbenzyl)ethylene and propylene diamines wherein Z is said 2-hydroxy-5-polybutylbenzyl group in the following equation:
  • the cyclic product of Equation I is 1-(2-hydroxy-5-polybutylbenzyl)-2-n-heptadecylimidazoline and of Equation 2 is 1-(2-hydroxy-S-polybutylbenzyl)-2-n-heptadecyl 1,4,5, -tetrahydropyrimidine.
  • Such specific compounds can be present in the reaction mixture resulting from the reaction of (1) polybutylphenol, (2) ethylene diamine or 1,3- propylene diamine, (3) formaldehyde and (4) stearic acid in the respective reactant mole ration of 1.0:1.0:1.0:1.0 but other related products can also be and are, in general, also present in admixture thereof.
  • EXAMPLE I There were combined, with stirring, at a temperature of 180 F., 2300 grams (0.66 mole) of a 1600 molecular weight polybutyl substituted phenol (46% polybutyl phenol, 54% polybutene and 690 grams of a solvent-extracted 5W mineral oil) 115 grams (0.61 mole) tetraethylene pentamine, and 93 grams (0.33 mole; equivalent 0.5 mole per mole polybutyl phenol) oleic acid. Thereafter, 90 ccs. (1.2 moles) formaldehyde were slowly added, and the temperature raised to 300 F., with nitrogen bubbled through the mixture at the rate of 2 cubic feet per hour (c.f.h.). After heating at 300 F. for three hours, a filteraid, such as Celite, was added and the mixture filtered. The recovered filtrate had a nitrogen content of 1.24%, a SSU viscosity at 210 F. of 677, and was crystal clear.
  • a filteraid such as
  • Example II The method of Example I was repeated, except that 1540 grams (0.444 mole) of the polybutyl phenol, 460 grams of the mineral oil, 77 (0.41 mole) grams of tetraethylene pentamine, 62 grams (0.220 mole; equivalent 0.5 mole per mole polybutyl phenol) oleic acid, and 60 ccs. (0.816 mole) formaldehyde were used.
  • the recovered filtrate was crystal clear, contained 1.2% nitrogen and had a SSU viscosity at 210 F. of 679.
  • EXAMPLE III 400 grams (0.111 mole) of a 1600 molecular weight polybutyl substituted phenol (44.5% polybutyl phenol, 55.5% polybutene and 86 grams of a solvent-extracted 5W mineral oil) 8 grams (0.028 mole; equivalent 0.25 mole per mole polybutyl phenol) oleic acid, and 19.3 grams (0.102 mole) tetraethylene pentamine were admixed at 180 F. 15 ccs. (0.204 mole) formaldehyde were then added, the temperature raised to 320 F., and maintained at said temperature for three hours, While introducing nitrogen at the rate of 0.5 c.f.h. A filter-aid was added and the product filtered. The recovered filtrate was crystal clear, contained 1.15% nitrogen, and had a SSU viscosity at 210 F. of 827.
  • EXAMPLE IV 2395 grams (0.666 mole) of a polybutyl phenol, as used in Example III, 328 grams of a solvent-extracted 5W mineral oil, 24 grams (0.084 mole; equivalent to 0.125 mole per mole of the polybutyl phenol) oleic acid, and 116 grams (0.612 mole) tetraethylene pentamine were mixed at a temperature of 180 F., and then ccs. (1.21 moles) formaldehyde were added. The reaction mixture was then heated to 340-360 F., and maintained at such temperature for 4 hours, while nitrogen at the rate of 0.5 c.f.h. was bubbled through the reaction mixture. A filter-aid was added, and the mixture filtered. The recovered filtrate was crystal clear, contained 1.4% nitrogen, and had a SSU viscosity at 210 F. of 1070.
  • EXAMPLE V 476 grams (0.132 mole) of a polybutyl phenol, as used in Example III, 84 grams of a solvent-extracted 5W mineral oil, 19 grams (0.066 mole; equivalent to 0.5 mole per mole of the polybutyl phenol) stearic acid, and 23 grams (0.122 mole) tetraethylene pentamine were admixed at 180 F. and then 18 ccs. (0.24 mole) formaldehyde added. The reaction mixture was then heated to 300 F. and reacted at said temperature for 3 hours, while nitrogen at the rate of 0.5 c.f.h. Filter-aid was then added and the mixture filtered. The recovered filtrate was clear, contained 1.22% nitrogen and had a SSU viscosity at 210 F. of 957.
  • EXAMPLE VI 238 grams (0.066 mole) of a polybutyl phenol, as used in Example III, 37 grams of a solvent extracted 5W mineral oil, 5.7 grams (0.033 mole; equivalent to 0.5 mole per mole of the polybutyl phenol) capric acid, and 11.5 grams (0.061 mole) tetraethylene pentamine were mixed at 180 F., and then 9.0 ccs. (0.12 mole) formaldehyde added. The reaction temperature was raised to 300 F. and maintained at said temperature for 3 hours while blowing with nitrogen at the rate of 0.5 c.f.h. Filter-aid was added, and the reaction mass filtered. The recovered filtrate was crystal clear, contained 1.48% nitrogen, and had a SSU viscosity at 210 F. of 978.
  • EXAMPLE VII Same procedure as used in Example VI, but using 7.5 grams (0.033 mole; equivalent to 0.5 mole per mole of the polybutyl phenol) myristic acid (in place of capric acid) and 40 grams of the mineral oil. The recovered filtrate was crystal clear, contained 1.4% nitrogen, and had a SSU viscosity at 210 F. of 967.
  • Example III 84 grams of a solvent-extracted mineral oil, 18.6 Fatty acid modified product of ExampleI 4.00 grams (equivalent to 0.5 mole per 111016 of the polybutyl 5 Magnellum suifqnate phenol) of a mixture of fatty acids, consisting principally Zinc dlaikyi dithlophisphaie of C and C monobasic acids, marked as Emery 894 fil i f by Emery Industries, Inc., and 23 grams of tetraethylene S1 lcone p0 ymer 0am agent pentamine were mixed together and heated to 170 F.
  • a solvent-extracted mineral oil 18.6 Fatty acid modified product of ExampleI 4.00 grams (equivalent to 0.5 mole per 111016 of the polybutyl 5 Magnellum suifqnate phenol) of a mixture of fatty acids, consisting principally Zinc dlaikyi dithlophisphaie of C and C monobasic acids, marked as Emery 894 fil i
  • This test a 480 hour test, con- Acryiolci IIPPIOVer and Pour-Point Agent ducted with a high-speed, super-changed Caterpillar diesel f y h mofiliied Product of Example II engine, is designed to measure the high temperature de- Zinc dlaikyi dlihlophosPhaie L10 tergency properties of a crankcase lubricating oil for Magnesium Suifonaie qualification under Army ordinahce specificaii on The result of the 289 Ford Test using the above for- 210413- T pefformhnce of Candidate hibrlcatmg P mulation is shown in the following Table III.
  • Varnish in the second Solvent-extracted 20 oil 93.22 groove and on the first land should not exceed 50%. Unmodified high molecular weight Mannich con- Below this the piston must be clean. densation product 5 .00
  • the following oil formulation was used in the Cater- Zinc dialkyl dithiophosphate 0.78 pillar 1-H Test: Magnesium sulfonate 1,00
  • Oil pump relief valve 9. 8 (9. 3) Plugging of oil rings None (None) Piston ring sticking None (None) Oil consumption (qts.) 5.35 (5. 22)
  • Such lubricating oils can be any normally liquid oleaginous lubricant, such as hydrocarbon oils, both natural, i.e. petroleum oils, and synthetic oils, for example, those obtained by the polymeriztion of olefins, as well as synthetic lubricating oils of the alkylene oxide type, and the polycarboxylic acid ester type, such as the oil-soluble esters of adipic acid, sebacic acid, azelaic acid, etc.
  • a method of preparing the oil-soluble acid modified high molecular weight Mannich Reaction product as solute in hydrocarbon diluent solvent consisting essentially of aliphatic hydrocarbon of 600-100,000 average molecular weight and mineral lubricating oil which comprises reacting at a temperature in the range of 275-375 F.
  • the reactants (a) a high molecular weight alkyl-substituted phenol wherein the alkyl-substituent has an average molecular weight of from about 600 to about 100,000; (b) an alkylene polyamine; (0) formaldehyde; and (d) a saturated or unsaturated aliphatic monocarboxylic acid containing from 10 to 20 carbon atoms, dimers or trimer of such unsaturated acids in the respective reactant molar ratio of 1.010.1-10:1.010:0.14l.0, wherein the amount of said diluent solvent provides 10-70 weight percent of the acid modified Mannich Reaction product.
  • hydrocarbon diluent solvent is polybutenyl derived hydrocarbon of about 1500 number average molecular weight and SAE- 5W oil
  • reactant (a) is about 1500 number average molecular weight poly butyl-substituted phenol
  • (b) is tetraethylenepentamine
  • (c) is formaldehyde
  • (d) is oleic acid and the amount of diluent solvent provides 40 weight percent of said Mannich product as solute.

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US4396517A (en) * 1981-08-10 1983-08-02 Mobil Oil Corporation Phenolic-containing mannich bases and lubricants containing same
EP0256863A3 (en) * 1986-08-20 1989-01-25 Texaco Development Corporation Precoupled mono-succinimide lubricating oil dispersants and viton seal additives
US4844827A (en) * 1988-01-25 1989-07-04 Amoco Corporation Lubricating oil additive
US4889646A (en) * 1987-06-30 1989-12-26 Amoco Corporation Nitrogen containing dispersants treated with mineral acids
EP0399764A1 (en) 1989-05-22 1990-11-28 Ethyl Petroleum Additives Limited Lubricant compositions
US5124055A (en) * 1988-03-31 1992-06-23 Ethyl Petroleum Additives, Inc. Lubricating oil composition
EP0537865A3 (en) * 1988-02-29 1993-06-23 Exxon Chemical Patents Inc. Polyanhydride modified dispersants
US5259968A (en) * 1988-02-29 1993-11-09 Exxon Chemical Patents Inc. Dispersant additive comprising the reaction product of a polyanhydride and a mannich condensation product
EP0683220A2 (en) 1994-05-18 1995-11-22 Ethyl Corporation Lubricant additive compositions
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EP0713908A1 (en) 1994-11-22 1996-05-29 Ethyl Corporation Power transmission fluids
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JPS6066386U (ja) * 1983-10-11 1985-05-11 森産業株式会社 絵文字合わせカ−ド

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Also Published As

Publication number Publication date
JPS5342761B1 (enrdf_load_stackoverflow) 1978-11-14
LU63518A1 (enrdf_load_stackoverflow) 1971-11-16
PL70101B1 (enrdf_load_stackoverflow) 1974-02-28
DE2134918A1 (de) 1972-01-27
FR2098379B1 (enrdf_load_stackoverflow) 1975-08-29
SU520910A3 (ru) 1976-07-05
SU458135A3 (ru) 1975-01-25
CA967698A (en) 1975-05-13
NL168237C (nl) 1982-03-16
NL7109677A (enrdf_load_stackoverflow) 1972-01-17
NL168237B (nl) 1981-10-16
DE2134918B2 (de) 1981-03-19
DE2134918C3 (de) 1982-01-28
FR2098379A1 (enrdf_load_stackoverflow) 1972-03-10
BE769904A (fr)
GB1358877A (en) 1974-07-03

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