US3108959A - Lubricant additive and composition containing same - Google Patents

Lubricant additive and composition containing same Download PDF

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US3108959A
US3108959A US778583A US77858358A US3108959A US 3108959 A US3108959 A US 3108959A US 778583 A US778583 A US 778583A US 77858358 A US77858358 A US 77858358A US 3108959 A US3108959 A US 3108959A
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reaction product
product
hydrocarbon
phosphorus
acid
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Donald L Klass
Roger W Watson
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Standard Oil Co
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Standard Oil Co
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Priority to NL246131D priority Critical patent/NL246131A/xx
Priority to FR812272A priority patent/FR1246407A/fr
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Priority to US778583A priority patent/US3108959A/en
Priority to US778576A priority patent/US3108958A/en
Priority to US778606A priority patent/US3089851A/en
Priority to DEST15883A priority patent/DE1255221B/de
Priority to GB41612/59A priority patent/GB930504A/en
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    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M159/00Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
    • C10M159/12Reaction products
    • C10M159/123Reaction products obtained by phosphorus or phosphorus-containing compounds, e.g. P x S x with organic compounds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/04Reaction products of phosphorus sulfur compounds with hydrocarbons
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    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00Chemical modification by after-treatment
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    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00Chemical modification by after-treatment
    • C08F8/34Introducing sulfur atoms or sulfur-containing groups
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M3/00Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
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    • C10M2205/00Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
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    • C10M2205/00Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
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    • C10M2205/00Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/026Butene
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/282Esters of (cyclo)aliphatic oolycarboxylic acids
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/34Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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    • C10M2209/00Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08Macromolecular 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
    • C10M2209/084Acrylate; Methacrylate
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    • C10M2209/00Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103Polyethers, i.e. containing di- or higher polyoxyalkylene groups
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    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/02Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
    • C10M2219/022Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds of hydrocarbons, e.g. olefines
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    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/02Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
    • C10M2219/024Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds of esters, e.g. fats
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    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
    • C10M2223/045Metal containing thio derivatives
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    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/12Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy
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    • C10M2225/00Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2225/04Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of macromolecualr compounds not containing phosphorus in the monomers
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2225/00Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2225/04Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of macromolecualr compounds not containing phosphorus in the monomers
    • C10M2225/041Hydrocarbon polymers
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    • C10M2227/00Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/06Organic compounds derived from inorganic acids or metal salts
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    • C10M2227/00Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/09Complexes with metals
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    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00Metal present as such or in compounds
    • C10N2010/04Groups 2 or 12
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    • C10N2010/00Metal present as such or in compounds
    • C10N2010/06Groups 3 or 13
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    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2070/00Specific manufacturing methods for lubricant compositions
    • C10N2070/02Concentrating of additives

Definitions

  • This invention relates to additive compositions for use in lubricating oils, the use of such additive compositions, and improved lubricating compositions containing such additive compositions and intended for use in internal combustion engines such as diesel engines and automobile engines. More particularly the invention relates to additive compositions which impart detergency and anti-rust properties to lubricating oils and suppress excess varnish formation and octane requirement increase when used in lubricating oils.
  • Straight petroleum lubrican s are effective within certain defined limits of engine operating conditions and when these limits are exceeded, such lubricants frequently fail to give the desired periormance demanded of them. Since, in modern engines designed to give increased performance, these limits are frequently exceeded, the use of straight mineral oils as lubricants produce undesirable conditions within the engine; thus varnish formation, corrosion, preignition and octane requirement are all excessive in modern engines using mineral oils alone.
  • a hydrolyzed phosphorus sulfide-hydrocarbon reaction product may be reacted with an amine compound and a borophosphoric acid to form a new composition of matter with desirable characteristics for use as an additive composition in a lubricating oil.
  • the boron and amine-containing additive composition of our present invention overcomes the problems of the mineral lubricating oil in its use without additives by imparting to the lubricating oil high detergency properties and eliminating excessive varnish formation and corrosion, while suppressing octane requirement increase.
  • the new composition may also be used in an additive concentrate in amounts of from to 50 weioht percent or more for addition to lubricating oils.
  • our present invention provides an additive composition for lubricating oils formed by reacting a hydrolyzed phosphorus sulfide-hydrocarbon reaction prodami. e comthe resulting neutralized reaction product with boroph'osphoric acid.
  • Our invention also provides an improved mineral oil containing an effective amount of our additive composition toimpart improved properties to the lubricating oil.
  • the amine compound used in preparing the additive composition of our present invention may be any aliphatic or substituted aliphatic compound having 1 or more basic amine groups.
  • Preferred amine compounds particularly suited for use in the preparation of the additive composition of our present invention are the hydroxy aliphatic amines such as monohydroxy, dihydroxy, and
  • polyhydroxy aliphatic amines and particularly preferred are the aliphatic polyamines such as diamines, triamines, etc., having two or more carbon atoms in the alipha ic ohain.
  • Polyhydroxy aliphatic polyamines are includable in either group.
  • Particularly suitable aliphatic polyamines are ailkylene polyamines containing at least two primary amino nitrogen atoms.
  • alkylene polyamines suitable for the hereindescribed purpose are ethylene diamine, propylene diamine, diethylene-triamine, diamylene triamine, triethylene tetramine, tripropylene tetramine, diethylene propylene tetramine, tetraethylene pcntamine, tetrabutylene pentamine, diethylendipropylcue pentamine, butylene diamine, dihexylene triamine, and the like, or mixtures thereof.
  • a suitable polyamine product is a crude diethylene triamine containing minor amounts :of ethylene diamine and triethylene tetramine.
  • Other suitable aliphatic polyamines include those having the general formula nnmcnpmn,
  • R is preferably a C to C aliphatic chain, and which are obtained by condensing the suitable amine with acrylonitrile and hydrogenating to the corresponding diamine.
  • aliphatic polyamines of this type are those marketed by Armour and Company as Duomeens, which are prepared by the condensation of a dodecyl (coco) amine or an octadecyl (tallow) amine with acrylonitrile followed by hydrogenation to the corresponding diamine product; these products are marketed as Du-omeen C and Duomeen T, respectively.
  • Borophosphoric acid a dry nonhygroscopic powder
  • Borophosphoric acid a dry nonhygroscopic powder
  • the hydrolyzed phosphorus, sulfide-hydrocarbon reaction product may be prepared by any method known to the prior art. Vie prefer to react a hydrocarbon with from about 1% to about 50%, and preferably from about 5% to about 25% of phosphorus sulfide at .a temperature of from about 200 'F. to about 600 F. in a nonoxidizing atmosphere, as, for example, in a nitrogen atmosphere. The reaction is carried out for from about one to about ten hours or more, and preferably for about five hours. The reaction may be carried out in the presence of a sulfurizing agent such as sulfur, sulfur chlorides, etc., if desired. The product is hydrolyzed at a temperature of from about 200 F.
  • the hydrolyzed product may be solvent extracted to remove salts of inorganic phosphorus acids and low molecular weight organic phosphorus acids formed during hydrolysis. Solvent extraction may be accomplished in accordance with the method described by Norman E. Lemmon et al. in U.S. 2,843,579, issued luly 15, 1958.
  • any phosphorus sulfides such as P 5 P 8 P 8 or other phosphorus sulfides and preferably phosphorus pentasulide, P 5 may be reacted with a hydrocarbon.
  • the hydrocarbons used in the phosphorus sulfidehydrocarbon reaction may be polymers such as monooletin polymers, copolymers, graft polymers, etc. and may also be unpolymerized or unpolymerizable hydrocarbons such as olefins, parafiins, cycloparaflins, aromatic hydrocarbons, etc.
  • the mono-olefin polymer to be treated may be the polymer resulting from the polymerization of low molecular weight mono-olefins preferably the isomonoolefins, such as isobutylene and isoamylene and/or the copolymers obtained by the polymerization of hydrocarbon mixtures containing isomono-olefins and mono-olcfins of less than six carbon atoms and preferably those of four carbon atoms.
  • the polymer may be obtained by the polymerization of these olefins or mixed olefins in the presence of catalysts such as sulfuric acid, phosphoric acid, or boron fluoride, aluminum chloride or other similar halide catalysts of the Friedel-Crafts type.
  • the polymers advantageously have molecular weights ranging from about 150 to about 50,000 or more, and preferably from about 500 to about 10,000.
  • a starting material there can be used the polymer or synthetic lubricating oil obtained by polymerizing the unsaturated hydrocarbons resulting from the vapor phase cracking of paraifin waxes in the presence of aluminum chloride which is fully described in U.S. patents Nos. 1,955,260; 1,970,402; and 2,091,398.
  • Still another type of olefin polymer which may be employed is the polymer resulting from the treatment of vapor phase cracked gasoline and/or gasoline fractions with sulfuric acid or solid adsorbents, such as fullers earth, whereby the unsaturated polymerized hydrocarbons are removed.
  • the treatment with phosphorus sulfide of the polymers resulting from the voltolization of hydrocarbons as described for example in US. Patents Nos. 2,197,768 and 2,191,787.
  • hydrocarbons which we can use as reactants in the preparation of the phosphorus sulfide reaction product are paraflins, olefins, aromatics or alkyl aromatics, cyclic aliphatics, petroleum fractions, such as lubricating oil fractions, petrolatums, waxes, cracking cycle stocks, condensation products of the foregoing hydrocarbons, solvent extracts of petroleum extracts, etc.
  • paraffin hydrocarbons can be those obtained from petroleum oils such as bright stock residuums, lubricating oil distillates, petrolatums, or paraffin waxes. We may also halogenate any of the foregoing parafiins and condense the same with aromatic hydrocarbons in the presence of anhydrous inorganic halides such as aluminum chloride, zinc chloride, boron fluoride and the like.
  • high molecular weight olefinic hydrocarbons which we may employ as reactants are cetene (C cerotene (C melene (C and mixed high molecular weight alkenes obtained by cracking petroleum oils.
  • olefins suitable for the preparation of the herein described phosphorus sulfide reaction products are olefins having at least 20 carbon atoms in the molecule of which from about 13 carbon atoms to about 18 carbon atoms, md preferably at least 15 carbon atoms are in a long chain.
  • Such olefins can be obtained by the dehydrogenation of parafiins, such as by the cracking of paraffin Waxes or by the dehalogena-tion of alkyl halides, preferably long chain alkyl halides, particularly halo genated parafiin waxes.
  • any of the hydrocarbons recited as useable by Norman E. Lernmon et al. in US. 2,843,579, issued July 15, 1958, may be employed herein.
  • the additive composition concentrates of our present invention are formed by neutralizing a hydrolyzed phosphorus sulfide-hydrocarbon reaction product, formed, for example, as indicated above and preferably solvent extracted, with an amine compound having 2 or more carbon atoms and preferably an aliphatic polyamine as defined above.
  • the neutralized product is then reacted with borophosphoric acid, preferably in amounts corresponding to from about 1 to about 3 moles boron per mole of neutralized product.
  • the borophosphoric acid reaction may be carried out in the resence of a suitable solvent for the borophosphoric acid such as alcohol, acetone, water, or other suitable solvent to increase solubility of the reactants.
  • a suitable solvent for the borophosphoric acid such as alcohol, acetone, water, or other suitable solvent to increase solubility of the reactants.
  • the reaction mixture is then heated to a temperature above C.
  • reaction mixture should not be heated to a temperature at which the amine is driven from the mixture. If temperatures higher than the boiling point of the amine are used means for retaining the amine, such as, for example, refluxing, should be employed.
  • An alternative method of forming the boron and phosphorus-containing amine-neutralized reaction products which we have found acceptable is by first reacting the borophosphoric acid with the amine compound and then reacting the resulting product with the phosphorus sulfide-hydrocarbon reaction product.
  • the reaction mixture is treated for removal of solvent by placing the mixture in a vacuum or by passing nitrogen gas or other inert gases through the reaction mixture at a temperature sufficient to strip solvent therefrom.
  • One to six hours is generally sutficient to strip the solvent out; however, this period of time is dependent on the amount and temperature of the stripping gas used as well as the nature of the solvent.
  • a lower boiling solvent such as acetone or methanol
  • the nitrogen blowing generally results in the formation of a clear product having dispersed impurities essentially removed.
  • the product should be hazy due to the presence of impurities, for example the presence of excess borophosphoric acid which has not reacted with the neutralized phosphorus sulfide hydrocarbon reaction product or has not dissolved therein, it may be desirable to filter the product through diatomaceous earth to obtain a suitably clear product.
  • the products formed in the above reaction contain chemically bonded boron and phosphorus.
  • the additive composition may be used in lubricating oils in varying amounts constituting minor proportions of the total lubricating composition.
  • the amount of additive used should be in excess of 0.1 weight percent.
  • the additive is effective in imparting improved detergcncy to lubricating oils even when used in such small amounts as range from about 0.1 weight percent.
  • HYDROLYZED INTERMEDIATE about five hours for product formation.
  • the product had a phosphorus content of about 4.3% and a sulfur content of about 7.5%.
  • the reaction product formed is then hydrolyzed with steam at a temperature of about 300 F. to about 400 F.
  • the hydrolyzed product was diluted, for ease of handling, to about a 60% concentrate with a solvent extracted Mid-Continent mineral oil having a viscosity of about 38 SSU at 210 F. This product was used as a starting material for the preparation of additives in subsequent examples.
  • Example 2000 grams of the solvent extracted hydrolyzed intermediate were reacted with 73 grams (one mole per mole of intermediate) of ethylenediainine and a basic salt was formed.
  • the basic salt was treated with 151 grams (1.22 moles per mole of intermediate) of borophosphoric acid with stirring at 100 C. for six hours.
  • the reaction mixture was blown with nitrogen; 1255 grams of solvent extracted Mid-Continent 5 weight mineral oil having a viscosity of about 38 SSU at 210 F. were added and the mixture was filtered through Celite.
  • the filtrate was a bright, brown, oil-soluble product which had a boron content of 0.16 Wt. percent, a nitrogen content of 0.58 wt. percent and a phosphorus content of 1.38 wt. percent.
  • the commercial-type oil used was a mixture of SW and 10W solvent extracted base stock containing a polyisobutylene polymer viscosity improver and having a viscosity of about 62 SSU at 210 F. having 0.75% by weight sulfurized dipentene corrosion inhibitor.
  • a run was also made on the commercial-type oil Without the product additive prepared in the above example and the comparative results are shown in Table I, below.
  • Concentrates of a suitable oil base containing more than 10 percent, for example up to 50 percent or more, of the additives of this invention alone or in combination with other additives 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.
  • an oil-soluble detergent neutralized reaction product prepared by the process comprising: reacting a phosphorus sulfide With a hydrocarbon; hydrolyzing the resulting phosphorus sulfidehydrocarbon reaction product; and reacting the hydrolyzed product with borophosphoric acid in an amount corresponding to from about one to about three moles of boron per mole of reaction product and with an aliphatic polya-rnine having from 2 to 21 carbon atoms in the aliphatic group in an amount corresponding to from about one to about 1.1 moles of polyarnine per mole of acid phosphorus, at a temperature below the temperature at which said polyarnine is driven "from the mixture of reactants.
  • a lubricating composition comprising a major amount of a hydrocarbon lubricating oil and from about 0.1 to about 20 weight percent of the composition of claim 1.
  • composition of claim 1 wherein the aliphatic polyamine is ethylene diamine.
  • an oil-soluble detergent neutralized reaction product prepared by the process comprising the steps of: reacting a phosphorus sulfide with a hydrocarbon; hydrolyzing the resultant phosphorus sulfide-hydrocarbon reaction product; neutralizing the hydrolyzed product with an aliphatic polyamine having from 2 to 21 carbon atoms in the aliphatic group in an amount corresponding to from about one to about 1.1 moles of polyamine per mole of acid phosphorus; and reacting the neutralize-d product with borophos-phoric acid in an amount corresponding to from about one to about three moles of boron per mole of reaction product at a temperature below the temperature at which said polyamine is driven from the mixture of reactants.
  • a lubricating composition comprising a major amount of hydrocarbon lubricating oil and from about 0.1 to about 20 weight percent of the composition of claim 4.
  • composition of claim 4 wherein the aliphatic polyamine is ethylene diamine.
  • an oil-soluble detergent neutralized reaction product prepared by the process comprising the steps of: reacting a phosphorus sulfide with a hydrocarbon; hydrolyzing the resultant phosphorus sulfide-hydrocarbon reaction product; reacting boro-phosphoric acid in an amount corresponding to from about one to about three moles of boron per mole of reaction product with an alkylene polyamine having from 2 to 21 carbon atoms in the alkylene group and containing at least two primary amino nitrogen atoms in an amount corresponding to from about one to about 1.1 moles of greases polyamine per mole of acid phosphorus; and reacting the resulting reaction product with the hydrolyzed phosphorus sulfide-hydrocarbon reaction product at a temperature below the temperature at which the polyaminc is driven from the mixture of reactants.
  • an oil-soluble detergent neutralized reaction product prepared by the process comprising the steps of: reacting phosphorus sulfide with a hydrocarbon; hydrolyzing the resulting phosphorus sulfide-hydrocarbon reaction product; neutralizing the resulting hydrolyzed product with from about one to about 1.1 moles per mole of hydnolyzed reaction product of ethylene diamine; and reacting the resulting neutralized product with from about one to about three moles based on boron of borophosphoric acid per mole of neutralized product at a temperature below the temperature at Which the polyamine is driven from the mixture of reactants.
  • an oil-soluble detergent neutralized reaction product prepared by the process comprising the steps of: reacting phosphorus sulfide with a butene polymer at a temperature of from about 200 to about 600 F.; hydrolyzing the resulting phosphorus sulfide-butene polymer reaction product; neutralizing the resulting hydrolyzed product with from about one to about 1.1 moles per mole of hydrolyzed reaction product of an alkylene polyamine having the formula wherein R is a C to C aliphatic hydrocarbon chain; reacting the resulting neutralized product With from about one to about three moles based on boron of borophosi2.
  • phoric acid per mole of neutralized product at a temperature below the tempenature at which the polyamine is driven from the mixture of reactants; and heating the reactants to a temperature above 100 C. whereby water is stripped from the reaction mixture.
  • a lubricant additive concentrate consisting essentially of a mineral lubricating oil containing more than about 10% of an oil-soluble detergene neutralized reaction product prepared by the process comprising: reacting a phosphorus sulfide With a hydrocarbon; hydrolyzing the resulting phosphorus sulfide-hydrocarbon reaction product; and reacting the hydrolyzed product with borophosphoric acid in an amount corresponding to from about one to about three moles of boron per mole of reaction product and with an aliphatic polyamine having from 2 to 21 carbon atoms in the aliphatic group in an amount corresponding to from about one to about 1.1 moles of polyamine per mole of acid phosphorus, at a temperature beiow the tempenature at which the polyamine driven from the mixture of reactants.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Molecular Biology (AREA)
  • General Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Lubricants (AREA)
US778583A 1958-12-08 1958-12-08 Lubricant additive and composition containing same Expired - Lifetime US3108959A (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
NL246131D NL246131A (enrdf_load_html_response) 1958-12-08
FR812272A FR1246407A (fr) 1958-12-08 1958-12-07 Additif pour lubrifiants
US778583A US3108959A (en) 1958-12-08 1958-12-08 Lubricant additive and composition containing same
US778576A US3108958A (en) 1958-12-08 1958-12-08 Lubricant additive and composition containing same
US778606A US3089851A (en) 1958-12-08 1958-12-08 Lubricant additive and composition containing same
DEST15883A DE1255221B (de) 1958-12-08 1959-12-08 Schmieroel
GB41612/59A GB930504A (en) 1958-12-08 1959-12-08 Boron and nitrogen-containing phosphor-sulphurized products, their preparation and their use as lubricant additives

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US778583A US3108959A (en) 1958-12-08 1958-12-08 Lubricant additive and composition containing same
US778576A US3108958A (en) 1958-12-08 1958-12-08 Lubricant additive and composition containing same
US778606A US3089851A (en) 1958-12-08 1958-12-08 Lubricant additive and composition containing same

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3185728A (en) * 1960-06-20 1965-05-25 Texaco Inc Ethylene diamine salts of thiophosphonic acids
US4438013A (en) 1983-05-27 1984-03-20 Olin Corporation Phosphorylated and thiophosphorylated poly(oxyalkylated) hydrazines and selected adducts and their use as corrosion inhibitors
US5652201A (en) * 1991-05-29 1997-07-29 Ethyl Petroleum Additives Inc. Lubricating oil compositions and concentrates and the use thereof

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3294684A (en) * 1963-07-11 1966-12-27 Standard Oil Co Lubricant compositions containing detergency additives
US5026493A (en) * 1989-08-03 1991-06-25 Ethyl Petroleum Additives, Inc. Reduced ash content lubricants
CN115820329B (zh) * 2022-12-30 2023-10-31 太原理工大学 层状硼磷酸胺化合物作为添加剂的润滑油及其制备方法

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US2053474A (en) * 1934-12-11 1936-09-08 Du Pont Higher alkyl borates and silicates and process for preparing same
US2160917A (en) * 1937-06-10 1939-06-06 Standard Oil Co Lubricant
US2346156A (en) * 1942-02-16 1944-04-11 Standard Oil Co Compounded lubricant
US2636258A (en) * 1949-02-23 1953-04-28 Jones Allen Fluid can punch and opener
US2798045A (en) * 1954-09-27 1957-07-02 Shell Dev Lubricating compositions
US2809934A (en) * 1953-10-01 1957-10-15 Standard Oil Co Detergent lubricants and lubricating oil additives and process of making the same
US2900376A (en) * 1955-10-31 1959-08-18 Standard Oil Co Hydrolysis of phosphorus sulfide-hydrocarbon reaction product

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Publication number Priority date Publication date Assignee Title
US2316082A (en) * 1941-03-24 1943-04-06 Standard Oil Co Lubricant
BE581744A (enrdf_load_html_response) * 1950-12-22
US2636858A (en) * 1951-06-07 1953-04-28 Standard Oil Dev Co Mineral oil additive
US3002924A (en) * 1958-05-26 1961-10-03 Standard Oil Co Lubricant additive and composition containing same

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2053474A (en) * 1934-12-11 1936-09-08 Du Pont Higher alkyl borates and silicates and process for preparing same
US2160917A (en) * 1937-06-10 1939-06-06 Standard Oil Co Lubricant
US2346156A (en) * 1942-02-16 1944-04-11 Standard Oil Co Compounded lubricant
US2636258A (en) * 1949-02-23 1953-04-28 Jones Allen Fluid can punch and opener
US2809934A (en) * 1953-10-01 1957-10-15 Standard Oil Co Detergent lubricants and lubricating oil additives and process of making the same
US2798045A (en) * 1954-09-27 1957-07-02 Shell Dev Lubricating compositions
US2900376A (en) * 1955-10-31 1959-08-18 Standard Oil Co Hydrolysis of phosphorus sulfide-hydrocarbon reaction product

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3185728A (en) * 1960-06-20 1965-05-25 Texaco Inc Ethylene diamine salts of thiophosphonic acids
US4438013A (en) 1983-05-27 1984-03-20 Olin Corporation Phosphorylated and thiophosphorylated poly(oxyalkylated) hydrazines and selected adducts and their use as corrosion inhibitors
US5652201A (en) * 1991-05-29 1997-07-29 Ethyl Petroleum Additives Inc. Lubricating oil compositions and concentrates and the use thereof

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Publication number Publication date
US3089851A (en) 1963-05-14
DE1255221B (de) 1967-11-30
US3108958A (en) 1963-10-29
NL246131A (enrdf_load_html_response)
FR1246407A (fr) 1960-10-10
GB930504A (en) 1963-07-03

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