US3254025A - Boron-containing acylated amine and lubricating compositions containing the same - Google Patents

Boron-containing acylated amine and lubricating compositions containing the same Download PDF

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US3254025A
US3254025A US18552062A US3254025A US 3254025 A US3254025 A US 3254025A US 18552062 A US18552062 A US 18552062A US 3254025 A US3254025 A US 3254025A
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boron
nitrogen
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Suer William M Le
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Lubrizol Corp
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    • C07D213/00Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with heteroatoms or with carbon atoms having three bonds to hetero atoms, with at the most one to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72Nitrogen atoms
    • C07D213/75Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
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    • C07D295/00Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2.] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2.] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2.] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
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    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
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Description

United States Patent BQRQN-CONTAINING ACYLATED AMHNE AND of Ohio No Drawing. Filed Apr. 6, 1962, er. No. 185,520

Claims. (Cl. 252-32.7)

1 This application is a continuation-in-part of copending application Ser. No. 132,305 filed August 18, 1961, now US. 3,087,936.

This invention relates to oil-soluble nitrogenand boroncontaining compositions and to the process of preparing the same. The compositions of this invention are useful as additives in lubricants, especially lubricants intended for use in internal combustion engines, gears, and power transmitting units.

One of the principal problems associated with present day automobile crankcase lubricants is that posed by the inevitable presence in the lubricant of foreign particles such as dirt, soot, water, and decomposition products resulting from breakdown of the lubricating oil. Even if there were none of this latter contaminant present the very nature of the design of the modern internal combustion engine is such that a significant amount of foreign matter will accumulate in the crankcase. Perhaps the most important of these contaminants is water because it seems to be responsible for the deposition of a mayonnaise-like sludge. It appears that if there were no water present the solid components of the mayonnaise-like sludge would circulate with the oil and be removed by the oil filter. It will be readily appreciated that the. deposition of the sludge presents a serious problem with respect to the efiicient operation of the engine and that it is desirable to prevent such deposition of sludge-like material.

The presence of water and the precursors of sludge in a lubricating oil is dependent largely upon the operating temperature of the oil. If the oil is operated at a high temperature the water, of course, will be eliminated by evaporation about as fast as it accumulates. In the absence of water as stated above the other foreign particles will be removed by the filter. At low oil temperatures, on the other hand, water will accumulate and so consequently will sludge. It is apparent that the environment in which a crankcase lubricant is maintained will determine to a large extent the ultimate performance of that lubricant.

High operating temperatures are characteristic of a lubricant in an engine that is run at relatively constant high speed. Thus, in an engine that is run at 60 miles per hour for a long period of time it is very unlikely that there will be any accumulation of water and it is similarly unlikely that there will be any formation and deposition of sludge, but in ordinary stop-and-go driving such as is the case with taxicabs, delivery trucks, police cruisers, etc., the crankcase lubricant will be alternately hot and cold, an ideal environment for the accumulation of water. In such cases the formation of sludge is a serious problem. This problem has been with the automotive industry for many years and its solution has been approached by the use of known detergents such as metal phenates and sulfonates but without notable success. Although such known detergents are very effective in solving the detergency problems associated with motor oils at high temperatures they have not been particularly effective in solving the problems associated with low temperature operation or, to put it better, those problems which are associated with crankcase lubricants in engines which are operated at alternating high and low temperatures.

3,254,025 Patented May 31, 1966 "ice 'It is accordingly a principal object of this invention to provide novel compositions of matter.

It is also an object of thisinvention to provide compositions which are adapted for use as additives in hydrocarbon oils.

It is also an object of this invention to provide composi tions which are effective as detergents in lubricating compositions.

It is another object of this invention to provide a novel. process for the preparation of products which are eiTec-' tive as dispersants in lubricant compositions.

It is another object of this invention to provide novel compositions which are effective dispersants in lubricant compositions intended for use in engines operated at alternating high and low temperatures.

It is another object of this invention to provide improved hydrocarbon oil compositions.

It is another object of this invention to provide improved lubricating compositions.

It is another object of this invention to provide improved fuel compositions.

These and other objects are achieved in accordance with this invention by providing a process for preparing oil-soluble nitrogenand boron-containing compositions comprising treating an acylated nitrogen composition characterized by the presence within its structure of (A) a substantially hydrocarbon-substituted succinic radical selected from the class consisting of succinoyl, succinimidoyl, and succinoyloxy radicals wherein the substantially hydrocarbon substitucnt contains at least about 50 aliphatic carbon atoms and (B) a nitrogen-containing group characterized by a nitrogen atom attached directly to said succinic radical, with a boron compound selected from the class consisting of boron oxide, boron halides, boron acids, and esters of boron acids in an amount to provide from about 0.1 atomic proportion of boron for each mole of said acylated nitrogen composition to about 10 atomic proportions of boron for each atomic proportion of nitrogen of said acylated nitrogen composition.

The substantially hydrocarbon substitucnt of the acylated nitrogen composition may contain polar groups provided, however, that the polar groups are not present in proportions sufficiently large to alter significantly the hydrocarbon character of the substituent. groups are exemplified by chloro, bromo, keto, ethereal, aldehydo, and ni-tro, etc. The upper limit with respect to the proportion of such polar groups in the substituent is approximately 10% based on the weight of the hydrocarbon portion of the substituent.

The sources of the substantially hydrocarbon substituent include principally the high molecular weight substantially saturated petroleum fractions and substantially saturated olefin polymers, particularly polymers of monoolefins having from 2 to 30 carbon atoms. The especially useful polymers are the polymers of l-mono-olefins such as ethylene, propene, l-butene, isobutene, l-hexene, l-octene, Z-methyl-l-heptene, 3-cyclohexyl-1-butene, and 2-methyl-5-propyl-l-hexene. Polymers of medial olefins, i.e., olefins in which the olefinic linkage is not at the terminal position, likewise are useful. They are illustrated by Z-butene, 3-pentene, and 4-octene.

Also useful are the interpolymers of the olefins such as those illustrated above with other interpolymerizable olefinic substances such as aromatic olefins, cyclic olefins, and polyolefins. Such interpolymers include, for example, those prepared by polymerizing isobutene with styrene; isobutene with butadiene; propene with isoprene; ethylene with piperylene; isobutene with chloroprene; isobutene with p-methyl styrene; l-hexene with 1,3-hexadiene; 1- octene with l-hexene; l-heptene with l-pentene; 3-methyl- The polar 3 l-butene with l-octene; 3,3-dimethyl-1-pentene with 1- hexene; isobutene with styrene and piperylene; etc.

The relative proportions of the mono-olefins to the other monomers in the interpolymers influence the stability and oil-solubility of the final products derived from such interpolymers. Thus, for reasons of oil-solubility and stability the interpolymers contemplated for use in this invention should be substantially aliphatic and substantially saturated, i.e., they should contain at least about 80%, preferably at least about 95%, on a weight basis of units derived from the aliphatic monoolefins and no more than about of olefinic linkages based on the total number of carbon-to-carbon covalent linkages. In most instances, the percentage of olefinic linkages should be less than about 2% of the total number of carbon-tocarbon covalent linkages.

Specific examples of such interpolymers include copolymer of 95 (by weight) of 'isobutene with 5% of styrene; terpolymer of 98% of isobutene with 1% of piperylene and 1% of chloroprene; terpolymer of 95% of isobutene' with 2% of l-butene and 3% of 1-hexene; terpolymer of 80% of isobu-tene with 20% of l-pentene and 20% of l-octene; copolymer of 80% of l-hexene and 20% of l-heptene; terpolymer of 90% of isobutene with 2% of cyclohexene and 8% of propene; and copolymer of 80% of ethylene and 20% of propene.

Another source of the substantially hydrocarbon radical comprises saturated aliphatic hydrocarbons such as highly refined high molecular-weight white oils or synthetic alkanes such as are obtained by hydrogenation of high molecular weight olefin polymers illustrated above or high molecular weight olefinic substances.

The use of olefin polymers having molecular weight of about 750-5000 is preferred. Higher molecular weight olefin polymers having molecular weights from about 10,000 to about 100,000 or higher have been found to impart also viscosity index improving properties to the final products of this invention. The use of such higher molecular weight olefin polymers often is desirable.

The nitrogen-containing group of the acylated nitrogen compositions of this invention is derived from compounds characterized by a radical having the structural configuration The two remaining valences of the nitrogen atom of the above radical preferably are satisfied by hydrogen, amino, or organic radicals bonded to said nitrogen atom through direct carbon-to-nitrogen linkages. Thus, the compounds from which the nitrogen-containing group may be derived include principally ammonia, aliphatic amines, aromatic amines, heterocyclic amines, or carbocyclic amines. The amines may be primary or secondary amines and may also be polyamines such as alkylene amines, arylene amines, cyclic polyamines, and the hydroxy-substituted derivatives of such polyamines.

Specific amines of these types are methylamine, N- methyl-ethylamine, N-methyl-octylamine, N-cyclohexylaniline, dibutylamine, cyclohexylamine, aniline, di(pmethyl)amine, dodecylamine, octadecylamine, o-phenyl enediamine, N,N'-di-n-butyl p-phenylenediamine, morpholine, piperazine, tetrahydropyrazine, indole, hexahydro-1,3,5-triazine, l-H-1,2,4-triazole, melamine, bis-(paminophenyl)methane, phenyl-methylenimine, menthanediamine, cyclohexamine, pyrrolidine, 3-amino-5,6-diphenyl-l,2,4-triazine, ethanolamine, diethanolamine, quinonediimine, 1,3-indandiimine, 2-octadecylimidazoline, 2-phenyl-4-methyl-imidazolidine, oxazolidine, and 2-heptyl-oxazolidine.

A preferred source of the nitrogen-containing group consists of polyamines, especially alkylene amines conforming for the most part to the formula HITT (al ylene- I H A A wherein n is an integer preferably less than about 10, A is a substantially hydrocarbon or hydrogen radical, and the alkylene radical is preferably a lower alkylene radical having less than about 8 carbon atoms. Thealkylene amines include principally methylene amines, ethylene amines, butylene amines, propylene amines, pentylene amines, hexylene amines, heptylene amines, octylene amines, other polymethylene amines, and also the cyclic and the higher homologues of such amines such as piper azines and amino-alkyl-substituted piperaZine-s. They are exemplified specifically by: ethylene diamine, triethylene tetramine, propylene diamine, decamethylene diamine, octamethylene diamine, di(heptamethylene)triamine, tripropylene tetramine, tetraethylene pentamine, trimethylene diamine, pentaethylene hexamine, di(trimethylene)- triamine, 2-heptyl-3-(2-aminopropyl)imidazoline, 4-methyl-imidazoline, 1,3-bis(Z-aminoethyl)imidazoline, pyrimidine, 1-(2-aminopropyl)piperazine. 1,4-bis(2 aminoethyl)piperazine, and Z-methyl-l- (Z-aminobutyl) pipera- Zine. Higher homologues such as are obtained by condensing two or more of the above-illustrated alkylene amines likewise are useful.

The ethylene amines are especially useful. They are described in some detail under the heading Ethylene Amines in Encyclopedia of Chemical Technology Kirk and Othmer, volume 5, pages 898905, Interscience Publishers, New York (1950). Such compounds are prepared most conveniently by the reaction of an alkylene chloride with ammonia. The reaction results in the production of somewhat complex mixtures of alkylene amines, including cyclic condensation products such as piperazines. These mixtures find use in the processof this invention. products may be obtained also by the use of pure alkylene amines. An especially useful alkylene amine for reasons of economy as well as effectiveness of the products derived therefrom is a mixture of ethylene amines prepared by the reaction of ethylene chloride and ammonia and having a composition which corresponds to that of tetraethylene pentamine.

Hydroxyalkyl-substituted alkylene amines, i.e., alkylene amines having one or more hydroxyalkyl substituents on the nitrogen atoms, likewise are contemplated for use herein. The hydroxyalkyl-substituted alkylene amines are preferably those in which the alkyl group is a lower alkyl group, i.e., having less than about 6 carbon atoms. Examples of such amines include N-(2-hydroxyethyl)ethylene diamine, N,N'-bis(2-hydroxyethyl)ethylene diamine, 1(2-hydroxyethyl)piperazine, mono hydroxypropylsubstituted diethylene triamine, 1,4-bis(2-hydroxypropyl)- piperazine, di-hydroxypropyl substituted tetraethylene pentamine, N-(3-hydroxypropyl)tetramethylene diamine, and 2-heptadecyl-l (2-hydroxyethyl)imidazoline.

Higher homologues such as are obtained by condensation of the above-illustrated alkylene amines or hydroxy alkyl-substituted alkylene amines through amino radicals or through hydroxy radicals are likewise useful. It will be appreciated that condensation through amino radicals results in a higher amine accompanied with removal of ammonia and that condensation through the hydroxy radicals results in products containing ether linkages accompanied with removal of water.

Other sources of the nitrogen-containing group include ureas, thioureas, hydrazines, guanidines, amidines, amides, thioamides, cyanamides, etc. illustrating such compounds ,are: hydrazine, phenylhydrazine, N,N'-dihphenylhydrazine, octadecylhydrazine, benzoylhydrazine, urea, thiourea, N-butylurea, stearylamide, oleylamide, guanidine, 1,3-diphenylguanidine, 1,2,3-tributylguanidine, benzamidine, octadecamidine, N;

On the other hand, quite satisfactory Specific examples N dimethylstearamidine, cyanamide, dicyandiamide, guanylurea, aminoguanidine, etc.

As indicated previously, the nitrogen-containing group in the acylated nitrogen compositions of this invention is characterized by a nitrogen atom attached directly to the succinic radical. It will be appreciated, of course, that the linkage between the nitrogen atom and a succinoyl radical is representative of an amide or an imide structure, that the linkage between a nitrogen atom and a succinimidoyl radical is representative of an amidine structure, and that the linkage between a nitrogen atom and succinoyloxy radical is representative of an ammoniumcarboxylic acid salt structure. Thus, the acylated nitrogen compositions of this invention are characterized by amide, amide-salt, imide, amidine, or salt linkages and in many instances a mixture of such linkages.

A convenient method for preparing the acylated nitrogen compositions comprises reacting a high molecular weight succinic acid-producing compound characterized by the presence within its structure of a high molecular weight oil-solubilizing group having at least about 50 aliphatic carbon atoms and at least one succinic acid-producing group and illustrated by one having the structural configuration wherein R is a substantially hydrocarbon radical having at least about 50 aliphatic carbon atoms and X is selected from the class consisting of halogen, hydroxy, hydrocarbon-oxy, and acyloxy radicals, with at least about one-half an equivalent amount of a nitrogen-containing compound characterized by the pres nce within its structure of at least one radical having the structural configuration.

The above process involves a reaction between the succinic acid-producing group with the nitrogen-containing radical to result in the direct attachment of the nitrogen atoms to the succinic radical, i.e., succinoyl, succinimidoyl, or succinoyloxy radical. The linkage formed between the nitrogen atom and the succinic radical may thus be that representative of a salt, amide, imide, or amidine radical. In most instances the product of the above process contains a mixture of linkages representative of such radicals. The precise relative proportions of such radicals in the product usually are not known as they depend to a large measure upon the type of the acid-producing group and the nitrogen-containing radical involved in the reaction and also upon the environment (e.g., temperature) in which the reaction is carried out. To illustrate, the reaction involving an acid or anhydride group with an amino nitrogen-containing radical at relatively low temperatures such as :below about 60 C. results predominantly in a salt linkage O (i.e., & ON-) but at relatively high temperatures such as above about 80 C. results predominantly in an amide, imide, or amidine linkage N H ll (i.e., C-N- r CN) In any event, however, the products obtained by .the above process, irrespective of the nature or relative proportions of the linkages present therein, have been found to be effective as additives in hydrocarbon oils for the purposes of this invention.

The substantially saturated, aliphatic hydrocarbonsubstituted succinic acids and anhydrides are especially preferred for use as the acid-producing reactant of this process for reasons of the particular effectiveness of the products obtained from such compounds as additives in hydrocarbon oils. The succinic compounds are readily available from the reaction of maleic anhydride with a high molecular weight olefin or a chlorinated hydrocarbon such as the olefin polymer described herein-above. The reaction involves merely heating the two reactants at a temperature about 100200 C. The product from such a reaction is an alkenyl succinic anhydride. The alkenyl group may be hydrogenated to an alkyl group. The anhydride may be hydrolyzed by treatment with water or steam to the corresponding acid. Either the anhydride or the acid may be converted to the corresponding acid halide or ester by reaction with, e.g., phosphorus halide, phenols, or alcohols.

In lieu of the olefins or chlorinated hydrocarbons, other hydrocarbons containing an activating polar substituent, i.e., a substituent which is capable of activating the hydrocarbon molecule in respect to reaction with maleic acid or anhydride, may be used in the aboveillustrated reaction for preparing the succinic compounds. Such polar substituents may be illustrated by sulfide, disulfide, nitro, mercaptan, bromine, ketone, or aldehyde radicals. Examples of such polar-substituted hydrocarbons include polypropene sulfide, di-polyisobutene disulfide, nitrated mineral oil, di-polyethylene sulfide, brominated polyethylene, etc. Another method useful for preparing the succinic acids and anhydrides involves the reaction of itaconic acid with a high molecular weight olefin or a polar-substituted hydrocarbon at a temperature usually within .the range from about 100 C. to about 200 C.

The acid halides of the succinic acids can be prepared by the reaction of the acids or their anhydrides with a halogenation agent such as phosphorus tri-bromide, phosphorus pentachloride or thionyl chloride. The esters of such acids can be prepared simply by the reaction of the acids or their anhydrides with an alcohol or a phenolic compound such as methanol, ethanol, =octadecanol, cyclohexanol, phenol, naphthol, octylphenol, etc. The esterification is usually promoted by the use of an alkaline catalyst such as sodium hydroxide or sodium alkoxide or an acidic catalyst such sulfuric acid. The nature of the alcoholic or phenolic portion of the ester radical appears to have little influence on the utility of such ester as reactant in the process described hereinabove.

The nitrogen-containing reactants useful in the above process are the compounds, described previously in this specification, from which the nitrogen-containing group the acylated nitrogen compositions of this invention can be derived.

The above process is usually carried out by heating a mixture of the acid-producing compound and the nitrogen-containing reactant at a temperature above about C., preferably within the range from about C. to about 250 C. However, when an acid or anyhydride is employed in reactions with an amino nitrogen-containing reactant, the process may be carried out at a lower temperature such as room temperature to obtain products having predominantly salt linkages or mixed salt-amide linkages. Such products may be converted, if desired, by heating to above 80 C. to products having predominantly amide, imide, or amidine linkages. The use of a solvent such as benzene, toluene, naphtha, mineral oil, xylene, n-hexane, or the like is often desirable in the above process to facilitate the control of the reaction temperature.

.The relative proportions of the acid-producing compounds and the nitrogen-containing reactants to be used in the above process are such that at least about one-half of a stoichiometrically equivalent amount of the nitrogencontaining reactant is used for each equivalent of the acidproducing compound used. In this regard it will be noted that the equivalent weight of the nitrogen-contain- Thus, ethylene diamine has two equivalents per mole; amino guanidine has four equivalents per mole; a succinic acid or ester has two equivalents per mole, etc.

The upper limit of the useful amount of the nitrogencontaining reactant appears to be about two moles for each equivalent of the acid-producing compound used. Such amount is required, for instance, in the formation of products havingpredominantly amidine linkages. On the other hand, the lower limit of about one-half equivalent of the nitrogen-containing reactant used for each equivalent of the acid-producing compound is based upon the stoichiometry for the formation of products having predominantly imide linkages or mixed acid-amide linkages. In most instances, the preferred amount of the nitrogen-containing reactant is at least about one equivalent for each equivalent of the acid-producing compound used.

The following examples illustrate the processes useful for preparing the acylated nitrogen compositions useful in the process of this invention:

EXAMPLE 1 A polyisobutenyl succinic anhydride is prepared by the reaction of a chlorinated polyisobutylene with maleic anhydride at 200 C. The polyisobutenyl radical has an average molecular Weight of 850 and the resulting alkenyl succinic anhydride is found to have an acid number of 113 (corresponding to an equivalent weight of 500). To a mixture of 500 grams (1 equivalent) of this polyisobutenyl succinic anhydride and 160' grams of toluene there is added at room temperature 35 grams (1 equivalent) of diethylene triamine. The addition is made portionwise throughout a period of 15 minutes, and an initial exothermic reaction caused the temperature to rise to 50 C. The mixture then is heated and a Watertoluene azetrope distilled from the mixture. When no more water would distill the mixture is heated to 150 C. at reduced pressure to remove the toluene. The residue is diluted with 350 grams of mineral oil and this solution is found to have a nitrogen content of 1.6%.

EXAMPLE 2 The procedure of Example 1 is repeated using 30 grams (1 equivalent) of ethylene diamine as the amine reactant. The nitrogen content of the resulting product is 1.4%.

EXAMPLE 3 The procedure of Example 1 is repeated using 55.5 grams (1.5 equivalents) of an ethylene amine mixture having a composition corresponding to that of triethylene tetramine. The resulting product has a nitrogen content of 1.9%.

EXAMPLE 4 The procedure of Example 1 is repeated using 55.0 grams (1.5 equivalents) of triethylene tetramine as the amine reactant. The resulting product has a nitrogen content of 2.9%.

EXAMPLE 5 To a mixture of 140 grams of toluene and 400 grams (0.78 equivalent) of a polyisobutenyl succinic anhydride (having an acid number of 109 and prepared from maleic anhydride and the chlorinated polyisobutylene of Example 1) there is added at room temperature 63.6 grams (1.55 equivalents) of a commercial ethylene amine mixture having an average composition corresponding to that of tetraethylene pentarnine. The mixture is heated to distill the water-toluene azeotrope and then to C. at reduced pressure to remove the remaining toluene. The residual polyamide has a nitrogen content of 4.7%.

EXAMPLE 6 The procedure of Example 1 is repeated using 46 grams (1.5 equivalents) of ethylene diamine as the amine reactant. The product which resulted has a nitrogen content of 1.5%. EXAMPLE 7 A polyisobutenyl succinic anhydride having an acid number of 105 and an equivalent weight of 540 is prepared by the reaction of a chlorinated polyisobutylene (having an average molecular weight of 1,050 and a chlorine content of 4.3%) and maleic anhydride. To a mixture of 300 parts by weight of the polyisobutenyl succinic anhydride and parts by weight of mineral oil there is added at 65-95 C. an equivalent amount (25 parts by weight) of the commercial ethylene amine mixture of Example 5. This mixture then is heated to 150 C. to distill all of the water formed in the reaction. Nitrogen is bubbled through the mixture at this tempera ture to insure removal of the last traces of water. The residue is diluted by 79 parts by weight of mineral oil and this oil solution found to have a nitrogen content of 1.6%.

EXAMPLE 8 To a solution of 1,000 grams (1.87 equivalents) of the,

polyisobutenyl succinic anhydride of Example 7, in 500 grams of mineral oil there is added at 85-95" C. 70 grams (1.87 equivalents) of tetraethylene pentamine. The mixture then is heated at 150*165 C. for four hours, blowing with nitrogen to aid in the removal of water. The residue is diluted with 200 grams of mineral oil and the oil solution found to have a nitrogen content of 1.4%.

EXAMPLE 10 A polypropenyl succinic anhydride is prepared by the reaction of a chlorinated polypropylene (having a molecular weight of about 900 and a chlorine content of 4%) and maleic anhydride at 200 C. The product has an acid number of 75. To a mixture of 390 grams (0.52 equivalent) of this polypropenyl succinic anhydride, 500 grams of toluene, and grams of mineral oil there is added portionwise 22 grams (0.52 equivalent) the commercial ethylene amine mixture of Example 5. The reaction mixture is heated at reflux temperature for three hours and water removed from an azeotrope with toluene.

The toluene then is removed by heating to 150 C./20-

millimeters. nitrogen.

The residue was found to contain 1.3% of EXAMPLE 1 l i A substituted succinic anhydride is prepared by reactng maleic anhydride with a chlorinated copolymer of isobutylene and styrene. The copolymer consists of' 94 parts by weight of isobutylene units and 6 parts by weight toluene there is added portionwise 22 grams (0.51 equivalent) of the commercial ethylene amine mixture of Example 5. The mixture is heated at reflux temperature for three hours to remove by azeotropic distillation all of the water formed in the reaction, and then at 150 C./20 millimeters to remove the toluene. The residue contains 1.1% by weight of nitrogen.

EXAMPLE 12 A substituted succinic anhydride is prepared by reacting maleic anhydride with a chlorinated copolymer of isobutylene and isoprene. The copolymer consists of 99 parts by weight of isobutylene units and 1% by weight of isoprene units. The molecular weight of the copolymer is 28,000 and the chlorine content of the chlorinated copolymer is 1.95%. The resulting alkenyl succinic anhydride had an acid number of 54. A mixture of 228 grams (0.22 equivalent) of an oil solution of this alkenyl succinic anhydride, 58 grams of additional mineral oil, 500 grams of toluene, and 9.3 grams (0.22 equivalent) of the commercial ethylene amine mixture of Example 5 is heated at 110120 C. for three hours, water being removed from an azeotrope with toluene. When all of the Water has thus been removed the toluene is distilled by heating to 150 C./20 millimeters. The residue is found to have a nitrogen content of 1.1%.

EXAMPLE 13 A polyisobutenyl succinic anhydride is prepared by the reaction of a chlorinated polyisobutylene with maleic anhydride. The chlorinated polyisobutylene has a chlo rine content of 2% and an average molecular weight of 11,000. The polyisobutenyl succinic anhydride has an acid number of 48. A mixture of 410 grams (0.35 equivalent) of this anhydride, grams (0.35 equivalent) of the commercial ethylene amine mixture of Example 5 and 500 grams of toluene is heated at reflux temperature for four hours to remove water from an azeotrope with toluene. The toluene then is removed by heating to 150 C./ millimeters. The nitrogen content of the residue is 1.3%.

EXAMPLE 14 The procedure of Example 5 is repeated except that 0.94 equivalent of the amine is used instead of 1.55 equivalents. The nitrogen content of the product is 3%.

EXAMPLE 15 A polyisobutenyl-substituted succinic acid is prepared by hydrolysis of the corresponding anhydride (prepared in turn by the condensation of a chlorinated polyiso-' To 1152 grams (1.5

EXAMPLE 16 A mixture of 1056 grams (2.0 equivalents) of the polyisobutenyl succinic anhydride of the preceding example (in which the polyisobutenyl group has a molecular Weight of 850), 89 grams (2.0 equivalents) of di-(1,2 propylene) triamine (having a nitrogen content of 31.3 370 grams of mineral oil and 100 grams of toluene is heated at reflux temperature (180190 C.) for 5 hours. A total of 18 grams of Water is collected from'the Watertoluene azeotrope. The residue is heated to 150 C./20 mm. to remove any last traces of water which might have remained. The nitrogen analysis of this residue is 1.9%.

10 EXAMPLE 17 A polyisobutylene having an average molecular weight of 50,000 is chlorinated to a chlorine content of 10% by weight. This chlorinated polyisobutylene is reacted with maleic anhydride to produce the corresponding polyisobutenyl succinic anhydride having an acid number of 24. To 6,000 grams (2.55 equivalents) of this anhydride there is added portionwise at 70105 C. 108 grams (2.55 equivalents) of the commercial ethylene amine mixture of Example 5 over a period of 45 minutes. The resulting mixture is heated for four hours at 160-180 C. While nitrogen is bubbled throughout to remove water. When all of the water has been removed the product is filtered and the filtrate found to have a nitrogen content of 0.6%

EXAMPLE 18 A mixture of 1 equivalent of a polyisobutene-substituted succinic anhydride having an acid number of 98 (prepared according to the procedure described in Example 1) and 1 equivalent of an acrolein-ammoni-a (molar rat-i0 of 1:1) interpolymer having a nitrogen content of 23% by weight is diluted with 40% by its weight of a mineral 'oil. The resulting mixture is heated to 155 C. and nitrogen is bubbled through the mixture at this temperature for 5 hours. The residue is found to have a nitrogen content of 1.35%

EXAMPLE 19 A cyanoethyl-substituted ethylene amine is prepared by mixing 212 grams of acrylonitrile with 216 grams of an ethylene amine mixture consisting of 75% by weight of triethylene tetramine and 25% by weight of diethylene triamine at room temperature and heating the mixture at 110130 C. for 5 hours and then to C./30 mm. To a mixture of 1110 grams of the polyisobutene-substituted succinic anhydride of Example 1 and 825 grams of mineral oil there is added at 60 C., 143 grams dropwise of the above cyanoethyl-substituted ethylene amine (having a nitrogen content of 31.8%). The mixture is heated at -160 C. for 5 hours while being purged with nitrogen. A total of 6 cc. of water is removed by distillation. The residue has a nitrogen content of 1.66%.

EXAMPLE 20 To a mixture of 430 grams of the polyisobutene-substituted succinic anhydride of Example 1 and 355 grams or" mineral oil there is added at 60-80 C. 108 grams of N-aminopropyl morph-oline throughout a period of 1 hour. The mixture is heated at 150-155 C. for 5 hours. The residue is found to have a nitrogen content of 2.3%.

EXAMPLE 21 To a mixture of 430 grams of the polyisobutene-substituted succinic anhydride of Example 1 and 304 grams of mineral oil there is added at 60-80 C. 33 grams of dipropylene triamine. The mixture is then heated at 150155 C. for 5 hours until no more water distills. The residue is found to have a nitrogen content of 1.45%

EXAMPLE 22 EXAMPLE 23 A mixture of 286 grams of polyisobutene-substituted succinic anhydride of Example 1, 96 grams of N,N-dibutyl ethylene diamine and 252 grams of mineral oil is 11' prepared at 60 C. and heated at 150-165 C. for hours while being purged with nitrogen. The residue is found to have a nitrogen content of 2.24%.

EXAMPLE 24 EXAMPLE 25 A mixture of 430 grams of the polyisobutene-substituted succinic anhydride of Example 1, 64 grams of 1,1-(dirnethylaminoethyl)-4-methyl-piperazine and 324 grams of mineral oil is prepared at 60 C. and then heated at 150-155 C. while being blown with nitrogen. The residue is found to have a nitrogen content of 1.81%

EXAMPLE 26 A mixture of 416 grams of polyisobutene-substituted succinic anhydride of Example 1, 124 grams of N-phenyl piperazine and 356 grams of mineral oil is prepared at 60 C. and then heated at 150-155 C. for 5 hours while being purged with nitrogen. No water is removed by such heating. The residue is found to have a nitrogen content of 2.07%

EXAMPLE 27 A diisobutenyl-substituted ethylene amine is prepared by reacting 590 grams of diisobutenyl chloride and 264 grams of a mixture consisting of 75 by weight of triethylene tetramine and 20% by weight of diethylene triamine in the presence of 264 grams of potassium hydroxide (85% purity) and 2200 grams of isopropyl alcohol at 85 -90 C. A mixture of 528 grams of polyisobutene-substituted succinic anhydride of Example 1, 101 grams of the above diisobutenyl-substituted ethylene amine and 411 grams of mineral oil is heated at 150- 160 C. while being purged with nitrogen until no more water distills. The residue has a nitrogen content of EXAMPLE 29 content of 0.25%.

- EXAMPLE 30 A mixture of 1000 grams of the polyisobutene-substituted succinic anhydride of Example 1, 159 grams of menthane diamine and 500 grams of mineral oil is prepared at 70-100 C. and heated at 150-190 C. while being blown with nitrogen until no water distills. The residue is diluted with 258 grams of mineral oil and the solution is found to have a nitrogen content of 1.32%.

EXAMPLE 31 A polypropylene-substituted succinic anhydride having an acid number of 84 is prepared by the reaction of a chlorinated polypropylene having 'a chlorine content of 3% and molecular weight of 1200 with maleic anhydride.

A mixture of 813 grams of the polypropylene-substituted succinic anhydride, 50 grams of a commercial ethylene amine mixture having an average composition corresponding to that of tetraethylene pentamine and 566 grams of mineral oil is heated at 150 C. for 5 hours. The residue is found to have a nitrogen content of 1.18%.

EXAMPLE 32 A mixture of 206 grams of N,N'-disecondary-butyl p-phenylene diamine, 1000 grams of the polyisobutenesubstituted succinic anhydride of Example 1 and 500 grams of mineral oil is prepared at C. and heated at 150-200 C. for 9.5 hours. The mixture is diluted with 290 grams of mineral oil, heated .to 160 C. and filtered. The filtrate is found to have a nitrogen content of 1.29%.

EXAMPLE 33 To 1000 grams of the polyisobutene-substituted succinic anhydride of Example 1 and 500 grams of mineral oil there is added 17.6 grams of hydrazine at 7080 C. The reaction is exothermic. The mixture is heated at 140150 C. for 1 hour whereupon 9 grams of water is collected as the distillate. To the residue there is then added 40 grams of an ethylene amine mixture having an average composition corresponding to that of tetraethylene pentamine at 70-80 C. The mixture is then heated at 150-160 C. while being purged with nitrogen until no more water is removed by distillation. The residue is diluted with 200 grams of mineral oil, heated to 160 C. and filtered. The filtrate has a nitrogen content of 1.16%.

EXAMPLE 34 To a solution of 1000 grams of the polyisobutene-substituted succinic anhydride of Example 1 in 500 grams of mineral oil there is added 28 grams of 1,1-dirnethyl hydrazine at 5060 C. The mixture is heated at 60- C. for 3 hours and then mixed with 40 grams of an ethylene amine mixture having an average composition corresponding to that of tetraethylene pentamine at 85- 95 C. The mixture is then heated at 150-185 C. for 6 hours whereupon 14 grams of water is collected as the distillate. The residue is diluted with 197 grams of mineral oil, heated to 160 C. and filtered. The filtrate has a nitrogen content of 1.53%

EXAMPLE 35 A mixture of 1000 grams of the polyisobutene-substituted succinic anhydride of Example 1, 333 grams of 1,2-di(3-aminopropoxy)ethane and 500 grams of mineral oil is heated at 170 C. for 5 hours whereupon 18 grams of water is collected as the distillate. The residue is diluted with 380 grams of mineraloil, heated to 160 C. and filtered. The filtrate has a nitrogen content of 2.3%.

EXAMPLE 36 A mixture of 1000 grams of the polyisobutene-substituted succinic anhydride of Example 1, 418 grams of di(3- aminopropoxy ethyl)ether and 500 grams of mineral oil is heated at -170 C. for 4 hours. A total of 17 grams of water is collected as the distillate. The residue is diluted with 433 grams of mineral oil heated to C. and filtered. The filtrate has the nitrogen content of 2.18%.

EXAMPLE 37 .water is removed as the distillate.

13 EXAMPLE 38 A mixture of 1000 grams of the polyisobutene-substituted succinic anhydride of Example 1, 254 grams of aminoguanidine bicarbonate and 500 grams of mineral oil is prepared at 80 C. and heated at l30165 C. for hours. The residue is mixed with 223 grams of mineral oil, heated to 150 C., and filtered, The filtrate has the nitrogen content of 3.38%.

EXAMPLE 39 A mixture of 1000 grams of the polyisobutene-substituted succinic anhydride of Example 1, 178 grams of 2-amino-pyridine and 500 grams of mineral oil is heated at 140175 C. for hours while being purged with nitrogen. A total of 16 grams of Water is collected as the distillate. The residue is diluted With 273 grams of mineral oil and filtered. The filtrate has a nitrogen content of 2.55%.

EXAMPLE 40 A mixture of 1000 grams of the polyisobutene-substituted succinic anhydride of Example 1, 103 grams of 2,6- diamino-pyridine and 500 grams of mineral oil is heated at 140180 C. for 11 hours while being purged with nitrogen. A total of 16 grams of water is collected as the distillate. The residue is diluted with 223 grams of mineral oil, heated to 1:50" C. and filtered. The filtrate has a nitrogen content of 2.15%.

EXAMPLE 41 A mixture of 1000 grams of polyisobutene-substituted succinic anhydride of Example 1, 159 gram of cyanoguanidine and 233 grams of toluene is heated at the reflux temperature for 14 hours while 7.15 grams of Water is removed by azeotropic distillation. The mixture is diluted with 740 gramsof mineral oil and toluene is then removed by heating the mixture to 150 C. The residue is filtered and the filtrate has the nitrogen content of 4.74%.

EXAMPLE 42 A mixture of 1632 grams of polyisobutene-substituted succinic anhydride of Example 1, 207 grams of a condensation product of acrolein with ammonia (molar ratio of 1:1) having a nitrogen content of 20%, 604 grams of mineral oil and 1750 grams of toluene is heated at the reflux temperature for 3 hours. A total of 31 grams of Toluene is then removed by heating the :mixture to 150 C./20 mm. The residue is found to have a nitrogen content of 1.89%.

EXAMPLE 43 A nitrogen-containing compound is prepared by mixing 100 grams of cyanoguanidine with 500 grams of ethylene amine mixture having an average composition corresponding to that of tetraethylene pentamine and heating the mixture at 7080 C. for 3 hours to obtain a homogeneous mass and filtering the mass. A mixture of 1000 grams of the polyisobutene-substituted succinic anhydride of Example l 96 grams of the above filtrate and 164 'grams of toluene is heated at the reflux temperature for 10 hours. Toluene is then removed by heating the mixture to 150 C./20 mm. The residue i diluted with 400 grams of mineral oil and filtered. The filtrate has a nitrogen content of 3.43%.

EXAMPLE 44 To a mixture of 544 grams of the polyisobutene-substituted succinic anhydride of Example 1, 283 grams of mineral OH and 281 grams of toluene there is added 30 grams of urea at 45 C. The resulting mixture is heated at 130-135 C. for 11 hours whereupon 2.5 cc, of water is removed as the distillate. The residue is then heated to 140 C./20 mm. and filtered. The filtrate has a nitrogen content of 1%.

1 4 EXAMPLE 4s A mixture of 1088 grams of the polyisobutene-substituted succinic anhydride of Example 1, 106 grams of dipropylene triamine, 500 grams of toluene is heated at the reflux temperature for 4 hours until no more Water distills. The residue is then heated to C./20 mm. and diluted with 392 grams of mineral oil. The oil solution is found to have a nitrogen content of 1.74%.-

EXAMPLE 46 A mixture of 1000 grams of the polyisobutene-substituted succinic anhydride of Example 1, 174 grams of phenylbiguanide and 270 grams of toluene is heated at the reflux temperature for 6.5 hours whereupon 25 grams of Water is removed by distillation. The residue is diluted with 500 grams of mineral oil and heated to C./20 mm. to distill off toluene. The residue is diluted further with 265 grams of mineral oil, heated to 150 C. and filtered. The filtrate has a nitrogen content of 3.4%.

EXAMPLE 47 A mixture of 920 grams of the polyisobutene-substituted succinic anhydride of Example 1, and 249 grams of bis-(dimethylaminopropyl)amino is heated at the reflux temperature until no more Water distills. The residue has a nitrogen content of 4%.

EXAMPLE 48 A mixture of 1000 grams of the polyisobutene-substituted succinic anhydride of Example 1, 363 grams of aminopropyl o'ctadecylamine and 1314 grams of mineral oil is heated at 2000 C. for 24 hours. The residue is filtered. The filtrate has a nitrogen content of 1.02%.

EXAMPLE 49 A mixture of 1000 grams of the polyisobutene-substituted succinic anhydride of Example 1, and 258 grams of di-n-butylamine is heated at C. for 12 hours and then to 200 C./ 25 mm. The residue is diluted with 1157 grams of mineral oil and filtered. The filtrate has a nitrogen content of 0.8%.

EXAMPLE 50 A mixture of 297 grams of the polyisobutene-substituted succinic anhydride of Example 1, 25 grams of melamine and 200 grams of mineral oil is heated at 250 C. for 9 hours and then at 290295 C. for 7 more hours. The residue is mixed with 50 grams of water, heated at reflux for 7 hours, dried and filtered. The filtrate has a nitrogen content of 2%.

EXAMPLE 51 A mixture of 1.0 equivalent of the dimethyl ester of the polyisobutene-substituted succinic anhydride of Example 1 and 1.0 equivalent of N,N-dibutyl thiourea is dissolved in five times its volume of xylene. The resulting mixture is heated at the reflux temperature until no more Water is removed by azeotropic distillation. The mixture is heated further and the xylene is removed by distillation. The residue is the acylated nitrogen compound.

EXAMPLE 53 A product is obtained by the procedure of Example 15 1, except that pyrrolidine (1 equivalent) is used in lieu of the ethylene diamine used.

EXAMPLE 54 A product is obtained by the procedure of Example 1, except that hexahydro-1,3,5-triazine (1 equivalent) is used in lieu of the ethylene diamine used.

EXAMPLE 55 A product is obtained by the procedure of Example 1, except that 1,3,4-dithiazolidine (1 equivalent) is used in lieu of the ethylene diamine used.

EXAMPLE 56 A product is obtained by the procedure of Example 1, except that hexamethylene tetramine (2 equivalents) is used in lieu of the ethylene diamine used.

EXAMPLE 57 A product is obtained by the procedure of Example 1,

except that triphentylene tetramine (3 equivalents) is used in lieu of the ethylene diamine used.

EXAMPLE 5 8 An equi-molar mixture of the polyisobutene-su'bstituted succinic anhydride of Example 1 and N-octyl thiourea is diluted with an equal volume of xylene. The resulting mixture is heated at the reflux temperature for 30 hours. The residue is an xylene solution of the product.

EXAMPLE 59 A product is obtained by the procedure of Example 5 8 except that oleylamide is used in lieu of the thiourea used.

EXAMPLE 60 A product is obtained by the procedure of Example 58 except that 1,3-diphenyl guanidine is used in lieu of the thiourea used.

EXAMPLE 61 A product is obtained by the procedure of Example 58 except that octadecamidine is used in lieu of the thiourea used.

EXAMPLE 62 A product is obtained by the procedure of Example 58 except that guanylurea is used in lieu of the thiourea used.

EXAMPLE 63 To a mixture of 396 grams of the polyiso'butene-substituted succinic anhydride of Example 1 and 282 grams of mineral oil there was added 34 grams of N-methyltrimethylene diamine at 60 C. within a period of one hour. The mixture was blown with nitrogen at 150 155 C. for 5 hours. The residue was found to have a nitrogen content of 1.41%.

EXAMPLE 64 A mixture of 386 grams of mineral oil, 528 grams of the polyisobutene-substituted succinic anhydride of Example 1, and 88.5 grams of 1,4-'bis(2-hydroxypropyl)-2- methyl piperazine was prepared at C. Themixture was heated at 180-276 C./40 mm. for 14.5 hours. The residue had a nitrogen content of 1.12%.

EXAMPLE 67 A mixture of 382 grams of mineral oil, 528 grams of the polyisobutene-substituted succinic anhydride of Example 1, and 53 grams of 1-methyl-4-(3-aminopropyl) piperazine was prepared at 60 C., heated to 150 C.,

and blown with nitrogen at 150l55 C. for 5 hours. The residue has a nitrogen content of 1.57%.

EXAMPLE 69 To a mixture of 800 grams of the polyisobutene-substituted succinic anhydride of Example 1 and 175 grams of toluene there was added 77 grams of a commercial mixture of alkylene amines and hydroxy alkyl-substituted alkylene amines consisting of approximately 2% (by weight) of diethylene triamine, 36% of 1-(2-aminoethyl) piperazine, 11% of 1-(2-hydroxyethyl)piperazine, 11% of N-(Z-hydroxyethyl)ethylenediamine, and 40% of higher homologues obtained as a result of condensation of the above-indicated amine components. ing mixture was heated at the reflux' temperature for 16.5 hours whereupon 12 cc. of water was collected as the distillate. The residue was then heated to 160 C./25 mm. and diluted with 570 grams of mineral oil. The final product was found to have a nitrogen content of 1.57%.

EXAMPLE 70 A product is obtained by the procedure of Example 69 except that an equimolar mixture of ammonia and bis(2-hydroxyethyl)amine is used in lieu of the thiourea used.

EXAMPLE 71 A product is obtained by the procedure of Example 69 except that benzidine is used in lieu of the thiourea used.

EXAMPLE 72 An acylated nitrogen composition is prepared according to the procedure of Example 1 except that the reaction mixture consists of 3880 grams, of the polyisobutenyl succinic anhydride, 376 grams of a mixture of triethylene tetramine and diethyl triamine (75:25 weight ratio), and 2785 grams of mineral oil. The product is found to have a nitrogen content of 2%.

:ample 1, and 59 grams of N-(Z-hydroxyethyl)trimethylenediamine was prepared at 60 C. The mixture was blown with nitrogen at 15()155 C. for 5 hours. The residue had a nitrogen content of 1.56%.

EXAMPLE 66 A mixture of 185 grams of mineral oil, 330 grams of ;the polyisobutene-substitutegl succinic anhydride of Ex- EXAMPLE 73 EXAMPLE 74 An acylated nitrogen composition is prepared according to the procedure of Example 31 except that the 'polyisobutene-substituted succinic anhydride of Example 1 (1 equivalent or 1.5 equivalents of the amine reactant) is substituted for the polypropylene-substituted succinic anhydride used.

The result- 1 7 EXAMPLE 75 An acylated nitr-ogen composition is prepared according to the procedure of Example 31 except that the polyisobutene-substituted succinic anhydride of Example 1 (1 equivalent for 2 equivalents of the amine reactant) is substituted for the polypropylene-substituted succinic anhydride used.

EXAMPLE 76 An acylated nitrogen composition is prepared according to the procedure of Example 4 except that the commercial ethylene amine mixture (1.5 equivalent per equivalent of the anhydride) of Example 7 is substituted for the triethylene tetramine used.

EXAMPLE 77 An acylated nitrogen composition is prepared according to the procedure of Example 31 except that the polyisobutene-substituted succinic anhydride of Example 1 (l-equivalent for 1 equivalent of the amine reactant) is substituted for the polypropylene-substituted succinic anhydride. The composition is found to have a nitrogen content of 1.5%.

The boron compounds useful in reaction with the acylated nitrogen compositions include boron oxide, boron oxide hydrate, boron trifluoride, boron tribromide, boron trichloride, HBF boron acids such as boronic acid (e.g., alkyl-B(OH) or aryl-B(OH) boric acid (i.e., H BO tetraboric acid (i.e., H B O metaboric acid (i.e., HBO and esters of such boron acids. The use of complexes of a boron trihalide with ethers, organic acids, inorganic acids, or hydrocarbons is a convenient means of introducing the boron reactant into the reaction mixture. Such complexes are known and are exemplified by boron-trifluoride-diethyl ether, boron trifluoride-phenol, boron trifiuoride-phosphoric acid, boron trichloride-chloroacetic acid, boron tribromide-dioxane, and boron trifluoride-methyl ethyl ether.

Specific examples of boronic acids include methyl boronic acid, phenyl-boronic acid, cyclohexyl boronic acid, p-heptylphenyl boronic acid and dodecyl boronic acid.

The boron acid esters include especially mono-, di-, and tri-organic esters of boric acid with alcohols or phenols such as, e.g., methanol, ethanol, isopropanol, cyclohexanol, cyclopentanol, l-octanol, 2-octanol, dodecanol, behenyl alcohol, oleyl alcohol, stearyl alcohol, benzyl alcohol, 2-butyl cyclohexanol, ethylene glycol, propylene glycol, trimethylene glycol, 1,3-butanediol, 2,4-hexanediol, 1,2-cyclohexanediol, 1,3-octanediol, glycerol, pentaerythritol, diethylene glycol, carbitol, Cellosolve, triethylene glycol, tripropylene glycol, phenol, naphthol, p-butylphenol, o,p-diheptylphenol, n-cyclohex- -ylphenol, 2,2-bis-(p-hydroxyphenyl)propane, polyisobutene (molecular weight of 1500)-substituted phenol, ethylchlorohydrin, o-chlorophenol, m-nitrophenol, 6-bromooctanol, and 7-keto-decanol. Lower alcohols, 1,2-glycols, and 1,3-glycols, i.e., those having less than about 8 carbon atoms are especially useful for preparing the boric acid esters for the purpose of this invention.

Methods for preparing the esters of boron acid are known and disclosed in the art (such as Chemical Reviews pages 959-1064, Volume 56). Thus, one method involves the reaction of boron trich-loride with 3 moles of an alcohol or a phenol to result in a tri-organ'ic borate. Another method involves the reaction of boric oxide with an alcohol or phenol. Another method involves the direct esterification of tetra boric acid with 3 moles of an alcohol or a phenol. Still another method involves the direct esterification of boric acid with a glycol to form, e.g., a cyclic alkylene borate.

The reaction of the acylated nitrogen compositions with the boron compounds can be efiected simply by mixing the reactants at the desired temperature. The use of an inert solvent is optional although it is often desirable, especially when a highly viscous or solid reactant is present in the reaction mixture. The inert solvent may be a hydrocarbon such as benzene, toluene, naphtha, cyclohexane, n-hexane, or mineral oil. The temperature of the reaction may be varied within wide ranges. Ordinarily it is preferably between about C. and about 250 C. In some instances it may be 25 C. or even lower. The upper limit of the temperature is the decomposition point of the particular reaction mixture.

The reaction is usually complete within a short period such as 0.5 to 6 hours. After the reaction is complete, the product may be dissolved in the solvent and the resulting solution purified by .centrifugation of filtrat-ion if it appears to be hazy or contain insoluble substances. Ordinarily the product is sufficiently pure so that further purification is unnecessary or optional.

A desirable mode of carrying out the process for the preparation of the oil-soluble, nitrogenand boron-containing compositions consists in preparing a solution or slurry of the boron reactant such as boric acid in a hydrocarbon solvent such as mineral oil or toluene and adding the acylated nitrogen reactant to this solution or slurry. The principal advantage of this particular method is the more efficient utilization of the boron re actant in the proces. Another advantage is that the resulting mineral oil solution of the product is more readily filterable in the event that filtration becomes necessary to remove haze or insoluble contaminants. The yield of the desired product is higher than that characteristic of the alternative methods of adding the boron reactant to the acylated nitrogen reactant.

The reaction of the acylated nitrogen compositions with the boron compounds results in a product containing boron and substantially all of the nitrogen originally present in the nitrogen reactant. It is believed that the reaction results in the formation of a complex between boron and nitrogen. Such complex may involve in some instances more than one atomic proportion of boron with one atomic proportion of nitrogen and in other instances more than one atomic proportion of nitrogen with one atomic proportion of boron. The nature of the complex is not clearly understood. Evidence appears to indicate that the complex results from a direct linkage between boron and nitrogen and that in most instances, the radicals originally present on the boron and the nitrogen atoms do not take part directly in the complex formation. How ever, in the case of a \boron acid as the reactant, the reaction is often accompanied with the formation of water.

Inasmuch as the precise stoichiometry of the complex formation is not known, the relative proportions of the reactants to be used in the process are based primarily upon the consideration of utility of the products for the purposes of this invention. In this regard, useful products are obtained from reaction mixtures in which the reactants are present in relative proportions as to provide from about 0.1 atomic proportions of boron for each mole of the acylated nitrogen composition used to about 10 atomic proportions of boron for each atomic propor tion of nitrogen of said acylated nitrogen composition used. The preferred amounts of reactants are such as to provide-from about 0.5 atomic proportion of boron for each mole of the acylated nitrogen composition to about 2 atomic proportions of boron for each atomic proportion of nitrogen used. To illustrate, the amount of a boron compound having one boron atom per molecule to be used with one mole of an acylated nitrogen composition having five nitrogen atoms per molecule is within the range from about 0.1 mole to about 50 moles, preferably from about 0.5 to about 10 moles.

The-following examples are illustative of the process for preparing the nitrogenand boron-containing compositions of this invention.

Example A To 600 grams (1 atomic proportion of nitrogen) of 19 the acylated nitrogen composition prepared according to the process of Example 77 there is added 45.5 grams (0.5 atomic proportion of boron) of boron trifluoridediethyl ether complex (1:1 molar ratio) at 6075 C. The resulting mixture is heated to 103 C. and then at 110 C./30 mm. to distill off all volatile components.

The residue is found to have a nitrogen content of 1.44% and a boron content of 0.49%.

Example B Example C An oleyl ester of boric acid is prepared by heating an equi-rnolar mixture of oleyl alcohol and boric acid in toluene at the reflux temperature While water is removed azeotropically. The reaction mixture is then heated to 150 C./20 mm. and the residue is the ester having a boron content of 3.2% and a saponification number of 62. A mixture of 344 grams (1 atomic proportion of boron) of the ester and 1645 grams (2.35 atomic proportions of nitrogen) of the acylated nitrogen composition obtained by the process of Example 72 is heated at 150 C. for 6 hours and then filtered. The filtrate is found to have a boron content of 0.6% and a nitrogen content of 1.74%.

Example D A mixture of 344 grams (1 atomic proportion of boron) of the oleyl ester of boric acid of Example C and 1112 grams (2.86 atomic proportions of nitrogen) of the acylated nitrogen composition obtained by the process of Example 73 is heated at 150 C. for 6 hours and filtered. The filtrate is found to have a nitrogen content of 1.94% and a boron content of 0.81%.

Example E Tri-isobutylborate is prepared by heating a mixture of 620 grams (10 moles) of boric acid, 2220 grams (30 moles) of isobutyl alcohol, and 800 grams of toluene at the reflux temperature while water formed during esterification is being removed by azeotropic distillation. The reaction mass is then heated at 100 C./20 mm. to distill off toluene and the borate is recovered by distillation at 105 110 C./20 mm. The distillate is found to have a boron content of 5.2%. A mixture of 57 grams (0.27 atomic proportion of boron), 13 grams of mineral oil, and 1045 grams (1.56 atomic proportions of nitrogen) of the product obtained by the process of Example 74 is heated at 150-160 C. for 3 hours and then blown with nitrogen at 170 C. (no volatile substance is formed). The mixture of then heated to 150 C./ 20 mm. and the residue is found to have a boron content of 0.39% and a nitrogen content of 1.98%.

Example F Examplev G A mixture of 31 grams (0.5 atomic proportion of boron) of boric acid and 1175 grams (1.75 atomic pro- 20 portions of nitrogen) of the acylated nitrogen composition prepared by the process of Example 74 is heated at 150 C. for 3 hours and filtered. The filtrate is found to have a boron content of 0.43% and a nitrogen content of 1.85%.

Example H A complex of phosphoric acid with 3 moles of boron trifluoride (67.3 grams, 0.62 atomic proportion of boron) is added dropwise to a mixture of 1344 grams (1.92 atomic proportions of nitrogen) of the acrylated nitrogen composition of Example 74 and 432 grams of mineral oil. An exothermic reaction occurs. The mixture is heated at -90 C. for 0.5 hour and mixed with 520 cc. of benzene. The resulting solution is washed with, successively, 500 cc. of Water, a mixture of 500 cc. of

.Water and 250 cc. of isopropyl alcohol, 50 cc. of a saturated sodium chloride solution, and a mixture of 750 cc. of water and 250 cc. of isopropyl alcohol. The washed product is heated to 150 C./3868 mm. within a period of 6 hours, cooled, and filtered. The filtrate is found to have a nitrogen content of 1.34% and a boron content of 0.1%.

Example I A mixture of 12 grams (0.38 mole) of sulfur, 124 grams (2 atomic proportions of boron) of boric acid, and 1018 grams (2 atomic proportions of nitrogen) of the acylated nitrogen composition of Example 75 is heated at 150 C. for 2 hours and, filtered. The filtrate is found to have a nitrogen content of 2.4%, a boron content of 1.68%, and a sulfur content of 0.5%.

Example J The process of Example I is repeated except that thiourea (38 grams, 0.5 mole) is substituted for the sulfur used. The product is found to have a nitrogen content of 3.3%, a sulfur content of 1.44%, and a boron content of 1.75%.

Example K A mixture of 55 grams (0.39 atomic proportion of boron) of boron trifiuoride-diethyl ether complex (1:1 molar ratio) and 480 grams (0.77 atomic proportion of nitrogen) of the product of Example 76 is heated at 80- C. for 0.5 hour and then to C./30 mm. The residue is found to have a nitrogen content of 2.08% and a boron content of 0.76%.

Example L A mixture of 372 grams (6 atomic proportions of boron) of boric acid and 3111 grams (6 atomic proportions of nitrogen) of the acylated nitrogen composition obtained by the process of Example 75 is heated at C. for 3 hours and then filtered. The filtrate is.

found to have a boron content of 1.64% and a nitrogen content of 2.56%.

Example M Boron trifluoride (272 grams, 4 atomic proportions of boron) is bubbled slowly into a mixture of 1790 grams of mineral oil and 5370 grams (7.3 atomic proportions of nitrogen) of the acylated nitrogen composition prepared by the process of Example 74. The mixture is then blown with nitrogen for 0.5 hours. The product, weighing 7426 grams (99% of theoretical yield), is found to have a nitrogen content of 1.38% and a boron content of 0.54%.

' Example N Boric acid (124 grams, 2 atomic proportions of boron) is added to the acylated nitrogen composition (55 6 grams, 1 atomic proportion of nitrogen) obtained according to the procedure of Example 75. The resulting mixture is heated at 150 C. for 3.5 hours and filtered at that temperature. The filtrate is found to have a boron compound of 3.23% and a nitrogen content of 2.3%.

Example A mixture of boric acid and the acylated nitrogen composition prepared according to the procedure of Example 17 in relative proportions such as to provide 1 atomic proportion of boron per atomic proportion of nitrogen is diluted with twice its volume of xylene and the result- Example P A mixture of boric acid and the acylated nitrogen composition obtained according to the procedure of Example 44 in relative proportions such as to provide 1 atomic proportion of boron per atomic proportion of nitrogen is heated at 150 C. for 3 hours and filtered. The filtrate is found to have a boron content of 0.2%.

Example Q A mixture of boric acid and an acylated nitrogen composition obtained by the procedure of Example 41 in relative proportions such as to provide 1 atomic proportion of boron per atomic proportion of nitrogen is heated at 150 C. for 3 hours and filtered at this temperature. The filtrate is found to have a boron content of 3.1% and a nitrogen content of 4.1%

Example R A mixture of boron trifiuoride-diethyl ether complex and a polyisobutene-substituted succinimide derived from a polyisobutene having an average molecular weight of 1000 in relative proportions such as to provide 1 atomic proportion of boron per atomic proportion of nitrogen is heated at 150 C. for 3 hours and filtered at this temperature.

Example S A mixture of boric acid and the acylated nitrogen composition obtained by the procedure of Example 37 in relative proportions such as to provide 1 atomic proportion of boron per atomic proportion of nitrogen is heated at 150 C. for 3 hours and filtered.

Example T A mixture of boric acid and the acylated nitrogen composition obtained according to the procedure of Example 25 in relative proportions such as to provide 1 atomic proportion of boron per atomic proportion of nitrogen is heated at 150 C. for 3 hours and filtered.

Example U ceous filter aid and filtered. The filtered product, representing 96% of the theoretical yield, is collected after a period of 2.2 hours of filtration. It has a boron content of 1.89% (theory, 1.97%) and a nitrogen content of 2.47% (theory, 2.54%). In a separate experiment it has been found that reversing the order of the addition of the boric acid and the acylated nitrogen reactant in the above :process lowers the yield to 88% of the theoretical quantity and results in a product having a boron content of 1.59% and a nitrogen content of 2.43%. The time required for completing the filtration has been found to be 15.4 hours.

The nitrogenand boron-containing products of this invention are useful for a wide variety of purposes including pesticides, plasticizers, rust-inhibiting agents for treatment of metals, corrosion-inhibiting agents, extreme pressure agents, anti-wear agents, and detergents.

A principal utility of such products is as additives in lubricants. It has been discovered in accordance with this invention that when used for such purpose the effectiveness of the nitrogenand boron-containing products to impart a specific property to a lubricant is closely related to the size of the substantially hydrocarbonsubstituent in the succinic radical of the acylated nitrogen composition from which such products are derived. More particularly it has been found that products in which the substantially hydrocarbon substituent contains more than about 50 aliphatic carbon atoms are effective to impart oxidation-inhibiting,

' corrosion-inhibiting, and detergent properties to a lubricant. It has also been found that the detergent properties of the products diminish sharply with a decrease in the size of the substantially hydrocarbon substituent having less than about 50 aliphatic carbon atoms so that products having less than about 35 aliphatic carbon atoms in this susbtituent are ineffective as detergent additives in lubricants.

The lubricating oils in which the compositions of this invention are useful as additives may be of synthetic, animal, vegetable, or mineral origin. Ordinarily mineral lubricating oils are preferred by reason of their availability, general excellence, and low cost. For certain applications, oils belonging to one of the other three groups may be preferred. For instance, synthetic polyesters oil such as didodecyl adipate and di-Z-ethylhexyl sebacate are often preferred as jet engine lubricants. Normally the lubricating oils preferred will 'be fluid oils, ranging in viscosity from about 40 Saybolt Universal Seconds at F. to about 200 Saybolt Universal Seconds at 210 F.

The concentration of the nitrogenand boron-containing compositions as additives in lubricants usually ranges from about 0.1% to about 10% by weight. The optimum concentrations for a particular application depend to a large measure upon the type of service to which the lubricants are to be subjected. Thus, for example, lubricants for use in gasoline internal combustion engines may con tain from about 0.5 to about 5% of the additive, whereas lubricating compositions for use in gears and diesel engines may contain as much as 10% or even more of the additive.

This invention contemplates also the presence of other additives in the lubricating compositions. Such additives include, for example, supplemental detergents of the ashcontaining type, viscosity index improving agents, pour point depressing agents, anti-foam agents, extreme pressure agents, rust-inhibiting agents, and supplemental oxidation and corrosion-inhibiting agents.

The ash-containing detergents are exemplified by oilsoluble neutral and basic salts of alkali or alkaline earth metals with sulfonic acids, carboxylic acids, or organic phosphorus acids characterized by at least one direct carbon-tophosphorus linkage such as those prepared by the treatment of an olefin polymer (e.g., polyisobutene having a molecular weight of 1000) with a phosphorizing agent such as phosphorus tn'chloride, phosphorus heptasulfide, phosphorus pentasulfide, phosphorus tn'chloride and sulfur, white phosphorus and a sulfur halide, or phos phorothioic chloride. The most commonly used salts of such acids are those of sodium, potassium, lithium, calcium, magnesium, strontium, and barium.

The term basic salt is used to designate the metal salts wherein the metal is present in stoichiometrically larger amounts than the organic acid radical. The commonly employed methods for preparing the basic salts involves heating a mineral oil solution of an acid with a stoichiometric excess of a metal neutralizing agent such as the metal oxide, hydroxide, carbonate, bicarbonate, or sulfide at a temperature about 50 C. and filtering the resulting mass. The use of a promoter in the neutralization step to aid the incorporation of a large excess of metal likewise is known. Examples of compounds useful as the promoter include phenolic substances such as phenol, naphthol, alkylphenol, thiophenol, sulfurized alkylphenol, and condensation products of formaldehyde with a phenolic substance; alcohols such as methanol, 2-propanol, octyl alcohol, Cellosolve, carbitol, ethylene glycol, stearyl alcohol, and cyclohexyl alcohol; amines such as aniline, phenylenediamine phenothiazine, phenyl-beta-naphthylamine, and dodecylamine. A particularly effective method for preparing the basic salts comprises mixing an acid with an excess of a basic alkaline earth metal neutralizing agent, a phenolic promoter compound, and a small amount of water and carb-onating the mixture at an elevated temperature such as 60200 C.

The preparation of a basic sulfonate detergent is illustrated as follows: A mixture of 490 parts (by weight) of a mineral oil, 110 parts of water, 61 parts of heptylphenol, 340 parts of barium mahogany sulfonate, and 227 parts of barium oxide is heated at 100 C. for 0.5 hour and then to 150 C. Carbon dioxide is then bubbled into the mixture until the mixture is substantially neutral. The mixture is filtered and the filtrate found to have a sulfate ash content of 25%.

The preparation of a basic barium salt of phosphorus acid is illustrated as follows: A polyisobutene having a molecular weight of 50,000 is mixed with by weight of phosphorus pentasulfide at 200 C. for 6 hours. The resulting product is hydrolyzed by treatment with steam at 1 60 C. to produce an acidic intermediate. The acidic intermediate is then converted to a basic salt by mixing with twice its volume of mineral oil, 2 moles of barium hydroxide and 0.7 mole of phenol and carbonating the mixture at 150 C. to produce a fluid product.

Furthermore, the oil-soluble, nitrogen-and boron-containing compositions of this invention have the unique effectiveness in enhancing the extreme pressure and corrosion-inhibiting properties of a certain class of additives employed to impart these properties to a lubricant. More specifically, the additives which are so benefited are metal dithiocarbamates, xanthates, the Group II metal phosphorodithioates and their epoxide adducts, hindered phenols, sulfurized cycloalkanes, di-alkyl polysulfides, sulfurized fatty esters, phosphosulfurized fatty esters, alkaline earth metal salts of alkylated phenols, dialkyl phosphites, triaryl phosphites, and esters of phosphorodithioic acids. Thus, it has been found that these additives become more effective in the presence of the nitrogen-and boron-containing compositions of this invention despite the fact that the latter by themselves may not impart any significant extreme pressure or oxidation-inhibiting properties to the lubricant under the particular service conditions. For this reason, combinations of the nitrogenand boron-containing compositions of this invention with any of the above-mentioned additives are especially desirable for use in lubricants which must have superior extreme pressure and oxidation-inhibiting characteristics.

The Group II metal phosphorodithioates are the salts of acids having the formula R2 SH in which R and R are substantially hydrocarbon radicals. The metals for forming such salts are exemplified by barium, calcium, strontium, zinc, and cadmium. The barium and zinc phosphorodithioates are especially preferred. The substantially hydrocarbon radicals in the phosphorodithioic acid are preferably low or medium molecular weight alkyl radicals and alkylphenyl radicals, i.e., those having from about 1 to about 30 carbon atoms in the alkyl group. Illustrative alkyl radicals include methyl, ethyl, isopropyl, isobutyl, n-butyl, sec-butyl, the various amyl alcohols, n-hexyl, methylisobutyl carbinyl,

heptyl, 2-ethylhexyl, diisobutyl, isooctyl, nonyl, behenyl, decyl, etc. Illustrative lower alkylphenyl radicals include butylphenyl, amylphenyl, di-amylphenyl, octylphenyl, etc. Cycloalkyl radicals likewise are useful and these include chiefly cyclohexyl and the lower alkyl-cyclohexyl radicals. Other substantially hydrocarbon radicals likewise are useful such as tetradecyl, octadecyl, eicosyl, butylnaphthyl, hexylnaphthyl, octylnaphthyl, cyclohexylphenyl, naphthenyl, etc. Many substituted hydrocarbon radicals may also be used, e.g., chloropentyl, dichlorophenyl, and dichlorodecyl.

The availability of the phosphorodithioic acids from which the Group II metal salts of this invention are prepared is Well known. They are prepared by the reaction of phosphorus pentasulfide with an alcohol or phenol. The reaction involves four moles of the alcohol or phenol per mole of phosphorus pentasulfide, and may be carried out within the temperature range from about 50 C. to about 200 C. Thus the preparation of 0,0-di-n-hexyl phosphorodithioic acid involves the reaction of phosphorus pentasulfide with four moles of n-hexyl alcohol at about C. for about 2 hours. Hydrogen sulfide is liberated and the residue is the defined acid. The preparation of the zinc or barium salt of this acid may be effected by reaction with zinc oxide or barium oxide. Simply mixing and heating these two reactants is sufiicient to cause the reaction to take place and the resulting product is sufliciently pure for the purposes of this invention.

Especiallyuseful Group II metal phosphorodithioates can be prepared from phosphorodithioic acids which in turn are prepared by the reaction of phosphorus pentasulfide with mixtures of alcohols. The use of such mixtures enables the utilization of cheaper alcohols which in themselves do not yield oil-soluble phosphorodithioic acids. Thus a mixture of isopropyl and hexyl alcohols can be used to produce a very effective, oil-soluble metal phosphorodithioate. For the same reason mixtures of simple phosphorodithioic (i.e., acids prepared from one alcohol) acids can be reacted with zinc oxide or barium oxide to produce less expensive, oil-soluble salts.

Another class of the phosphorothioate additives contemplate-d for use in the lubricating compositions of this invention comprises the adducts of the metal phosphorodithioates described above with an epoxide. The metal phosphorodithioates useful in preparing such addu-cts are for the most part the zinc phosphorodithioates. The epoxides may be alkylene oxides or arylalkylene oxides. The arylalkylene oxides are exemplified by styrene oxide, p-ethylstyrene oxide, alpha-methylstyrene oxide, 3-beta-naphthyl-1,3-butylene oxide, m-dodecylstyrene oxide, and p-chlorostyrene oxide. The alkylene oxides include principally the lower alkylene oxides in which the alkylene radical contains 6 or less carbon atoms. Examples of such lower alkylene oxides are ethylene oxide, propylene oxide, 1,2-bu'tene oxide, trirnethylene oxide, tetramethylene oxide, butadiene monoepoxide, 1,2-hexene oxide, and propylene epichlorohydrin. Other epoxides useful herein include, for example, butyl 9,10-epoxystearate, epoxidized soya bean oil, epoxidized tung oil, and epoxidized copolymer of styrene with butadiene.

The adduct may be obtained by simply mixing the phosphorodithioate and the epoxide. The reaction is usually exothermic and may be carried out within wide temperature limits from about 0 C. to about 200 C. Because the reaction is exothermic itis best carried out by adding one reactant, usually the epoxide, in small increments to the other reactant in order to obtain convenient control of the temperature of the reactiton. The reaction may be carried out in a solvent such as benzene, mineral oil, naphtha, or n-hexane.

The chemical structure of the adduct is not known. More than one mole, sometimes as many as four moles, of the epoxide can be made to combine wit-h the phosphorodithioate to form products useful herein. However,

adducts obtained by the reaction of one mole of phosphorodithioate with from about 0.25 mole to about 1 mole of a lower alkylene oxide, particularly ethylene oxide and propylene oxide, have been found to be especially useful and therefore are preferred.

The hindered phenols are those in which the carbon atoms at both ortho positions to the phenolic group contain substantially large substituents so as to cause hinderance of the phenolic group. The common substituents are the secondary and tertiary alkyl radicals such as isopropyl, tert-butyl, tert-pentyl, sec-pentyl, cyclohexyl, and tert-octyl radicals. They likewise may be aryl radicals or large polar radicals such as bromo or nitro radicals. Examples of the hindered phenols in clude 2,6-di-sec-butylphenol, 2,4,-ditert-butylphenol, 2,6- di-tert-octyl-4-sec-pentylphenol, 2 tert-pentyl-G-tert-hexylphenol, 2-tert-butyl-6-cyclohexyl-6-heptylphenol, 4,4- bis-methylene-(2,6-di-tert-butylphenol), 4,4 methylenebis(Z-tert-butyl-6-sec-butylphenol), 2,4 dimethyl-6-tertbutylphenol, 2,6-di-tert-butyl-6-methylphenol, and bis- (3,5-di-tert-butyl-4 hydroxybenzyl) sulfide.

The sulfurized esters of the fatty acids are obtained by the treatment of the esters with a sulfurizing agent such as sulfur or a sulfur halide, e.g., sulfur monochloride or sulfur dichloride. The esters are exemplified by methyl oleate, methyl stearate, allyl stearate, isopropyl myristate, cyclohexyl ester of tall oil acid, ethyl palmitate, isooctyl laura te, diester of ethylene glycol with stearic acid, tetra-' ester of pentaerythritol with stearic acid, etc. Likewise useful are esters of higher alcohols or commercial alcohol mixtures such as octadecyl alcohol and sperm oil alcohol,

and phenols such as phenol, naphthol, p-cresol, and o,p-

dihexylphenol. The sulfurization is effected most conveniently at temperatures between 100 C. and 250 C. More than one atom of sulfur can be incorporated into the ester by the use of an excess of the sulfurizing agent. For the purpose of this invention sulfurized esters having as many as 4 or 5 atoms of sulfur per molecule have been found to be useful. Examples include sulfurized sperm oil having a sulfur content of 5%, sulfurized tall oil having a sulfur content of 9%, sulfurized methyl oleate having a sulfur content of 3%, and sulfurized stearyl stearate having a sulfur content of 15% Still another class of the fatty compounds consists of the phosphosulfurized fatty acid ester mentioned above. They are obtained by the treatment of the esters with a phosphorous sulfide, such as phosphorous pentasulfide, phosphorous sesquisulfide, or phosphorous heptasulfide. The treatment is illustrated by mixing an ester with from about 05% to 25% of a phosphorous sulfide at a temperature within the range from 100 C. to 250 C. The product contains both phosphorous and sulfur but the precise chemical constitution of such a product .is not clearly understood. These and other methods for preparing the sulfurized esters and phosphosulfurized esters are known in the art.

The polysulfides include principally aliphatic and cycloaliphatic disulfides, trisulfides, tetrasulfides, pentasulfides, or higher polysulfides. The term polysulfide designates a compound in which two substantially hydrocarbon radicals are joined to a group consisting of at least 2 sulfur atoms. It is represented for the most part by any of the structural formulas below:

wherein R and R are alkyl or cycloalkyl radicals and n is an integer usually less than 6. The nature of the linkage between the sulfur atoms is not clearly understood. It is believed, however, that such linkage may be described by a single covalent bond, a double bond, or a coordinate covalent bond. The polysulfides containing at least about 6 carbon atoms per molecule have greater oilsolubility and are generally preferred. Specific examples of such polysulfides are diisobutyl trisulfide, diisopentyl trisulfide, di-n-butyl tetrasulfide, dicyclopentyl disulfide, di-methylcyclohexyl tetrasulfide, di-2-ethylhexylpentyl disulfide, dipentyl trisulfide, di-beta-pinyl pentasulfide, cyclohexyl cyclopentyl trisulfide, diparaflin wax trisulfide, di-terpenyl disulfide, didodecyl trisulfide, dibehenyl trisulfide, and diisobutyl hexasulfide. Other polysulfides, including polar-substituted sulfides, are exemplified by di omega-bromopentyl) trisulfide.

The preparation of the polysulfide may be accom plished by any of the various processes which are known and disclosed in the art including, for example, the reaction of a chlorohydrocarbon with an alkaline metal polysulfide, the reaction of a mercaptan with sulfur and/ or sulfur halide, the reaction of saturated and unsaturated hydrocarbons with sulfur and/or sulfur halides, the reac tion of a hydrocarbon monosulfide with sulfur, etc.

The phosphites useful herein are the diand tri-hydrocarbon esters of phosphorous acid. Examples of the phosphites are: dibutyl phosphite, diheptylphosphite, di cyclohexylphosphite, tri-(pentylphenyDphosphite, tris- (dipentylphenyl)phosphite, didecyl phosphite, di-stearyl phosphite, tris-(hexa-propylene-substituted phenyl)p-hosphite, tri-hexyl phosphite, di-heptyl phenyl phosphite, and tri (m-chloro-p-heptylphenyl) phosphite.

The'alkaline earth metal salts of the alkylated phenols include principally the salts of magnesium, barium, calcium, and strontium with phenolic substances containing an alkyl substituent having at least about 7 carbon atoms. The phenols are exemplified by alkyl phenols, alkyl naphthols, sulfurized alkyl phenols, and the condensation products'of alkyl phenols with an aldehyde. Specific examples include magnesium octylphenate, barium polypropylene-substituted phenate in which the polypropylene substituent has a molecular weight of 500, calcium salt of alpha-dodecyl-beta-naphthyl, barium salt of bis(heptyl- .phenol)sulfide, calcium salt of bis(nonylphenol)sulfide,

calcium salt of the condensation product of two moles of heptylphenol with formaldehyde, barium dodecylphenate, and strontium polyisobutene-substituted phenate in which the polyisobutene substituent has a molecular weight of 350.

The esters of the phosphorodithioic acids include the aryl and the alkyl esters of the phosphorodithioic acids described hereinabove. A particularly useful group of the esters is obtained by the addition of the phosphorodithioic acids to an olefinic compound such as an alkene or an aralkene. They are obtained, for example, by the addition of diisopropylphosphorodithioic acid with styrene, propene, isobutene, cyclohexene, 1octene, methyl cyclohexene, isoprene, butadiene, dipentene, or the like.

Combinations of the nitrogenand boron-containing compositions of this invention with other additives can be obtained simply by mixing these additives or adding them to a lubricating oil at concentrations appropriate to prepare either concentrates or final lubricants. In many instances they can be prepared by the alternative process in which the acylated nitrogen composition from which the boronand nitrogen-containing compositions are derived are first mixed with the other additives and the boron reactant is then added to the mixture under the conditions as described previously for the process of this invention. Such a process is illustrated as follows: A mixture of 1430 parts (by weight) of the acylated nitrogen composition obtained by the process of Example 75 and 370 parts of zinc dioctylphosphorodithioate is heated to C. To this mixture there is added 200 parts of boric acid at 115 C. within a period of 15 minutes. The resulting mixture is blown with nitrogen at C. for 3 hours and filtered. The filtered product is found to have a phosphorus content of 1.3% (theory, 1.34%), a boron content of 1.52% (theory, 1.8%), a zinc content of 1.44% (theory, 1.47%), and a nitrogen content of 2% (theory, 2%).

Another alternative method comprises mixing the phosphorodithioate with the boron reactant and then treating the mixture with the acylated nitrogen composition. Still other alternative methods may be employed. They may involve, for instance, the preparation of the acylated nitrogen compositions in the presence of the phosphorodithioates and then treating the entire mixture with the boron reactant, or first preparing a mixture of the phosphorodithioate with the boron reactant (such as boric acid) and a nitrogen reactant (such as triethylene tetramine) and then treating the entire mixture with a succinic acidproducing compound (such as a polyisobutene-substituted succinic anhydride).

These and other alternative methods may be illustrated more specifically as follows: (1) a fluid mixture of mineral oil, zinc dioctylphosphorodithioate and the polyisobutenyl succinic anhydride of Example 1, and an ethylene amine mixture having an average composition corresponding to that of tetraethylene pentamine is heated at 120-130 C. to, distill off water and the resulting mixture is treated with boric acid at 110-135 C. and then filtered to give an oil solution of the additives, (2) a fluid mixture of mineral oil, Zinc dioctylphosphorodithioate, an ethylene amine mixture having an average composition corresponding to that of tetraethylene pentamine, and the polyisobutenyl succinic anhydride of Example 1 is heated to 120-140 C. and then treated with boric acid at 110- 135 C. and filtered to give an oil solution of the additives, (3) a fluid mixture of mineral oil, zinc dioctylphosphorodithioate, the polyisobutenyl succinic anhydride of Example 1, boric acid, and an ethylene amine mixture having an average composition corresponding to that of tetraethylene pentamine is heated at ll130 C. to distill off water and then filtered to give an oil solution of the additives, and (4) a fluid mixture of mineral oil, zinc dioctylphosphorodithioate, an ethylene amine mixture having an average composition corresponding to that of tetraethylene pentamine, and boric acid is heated to 75 C. and then mixed with the polyisobutenyl succinic anhydride of Example 1 at 110-140 C. and then filtered to give an oil solution of the additives.

The lubricating compositions may also contain metal detergent additives in amounts usually within the range of about 0.1% to about 20% by weight. In some applications such as in lubricating marine diesel engines the lubricating compositions may contain as much as 30% of a metal detergent additive. They may also contain extreme pressure addition agents, viscosity index improving agents, and pour point depressing agents, each in amounts Within the range from about 0.1% to about The following examples are illustrative of the lubricating compositions of this invention (all percentages are bv weight):

EXAMPLE I SAE 20 mineral lubricating oil containing 0.5% of the product of Example A.

EXAMPLE II SAE 30 mineral lubricating oil containing 0.75% of the product of Example B and 0.1% of phosphorus as the barium salt of di-n-nonylphosphorodithioic acid.

EXAMPLE III SAE 10W-30 mineral lubricating oil containing 0.4% of the product of Example C.

EXAMPLE IV EXAMPLE V SAE 30 mineral lubricating oil containing 2% of the product of Example M. p

28' EXAMPLE VI SAE W30 mineral lubricating oil containing 5% of the product of Example M.

- EXAMPLE VII SAE 10W-30 mineral lubricating oil containing 1.5% of the product of Example E and 0.05% of phosphorus as the zinc salt of a phosphorodithioic acid prepared by the reaction of phosphorus pentasulfide with a mixture of 60% (mole) of p-butylphenol and 40% (mole) of EXAMPLE VIII SAE 50 mineral lubricating oil containing 3% of the product of Example F and 0.1% of phosphorus as the calcium salt of di-hexylphosphoro-dithioate.

i the product of Example G, 0.06% of phosphorus as zinc di-n-octylphosphorodithioate, and 1% of sulfate ash as barium mahogany sulfonate.

EXAMPLE X SAE 30 mineral lubricating oil containing 5% of the product of Example H, 0.1% of phosphorus as the Zinc salt of a mixture of equimolar amounts of di-isopropylphosphorodithioic acid and di-n-decylphosphorodithioic acid, and 2.5% of sulfate ash as a basic barium detergent prepared by carbonating at 150 C. a mixture comprising mineral oil, barium di-dodecylbenzene sulfonate and 1.5 moles of barium hydroxide in the presence of a small amount of Water and 0.7 mole of octylphenol as the promoter.

EXAMPLE XI SAE 10W-30 mineral lubricating oil containing 6% of the product of Example I, 0.075% of phosphorus as zinc di-n-octylphosphorodithioate, and 5% of the barium salt of an acidic composition prepared by the reaction of 1000 parts of polyisobutene having a molecular weight of 60,000 with parts of phosphorus pentasulfide at 200 C. and hydrolyzing the product with steam at 150 C.

EXAMPLE XII SAE 10 mineral lubricating oil containing 2% of the product of Example J, 0.075% of phosphorus as the adduct of zinc di-cyclohexylphosphorodithioate treated with 03 mole of ethylene oxide, 2% of a sulfurized sperm oil having a sulfur content of 10%, 3.5% of a poly-(alkyl methacrylate) viscosity index improver, 0.02% of a poly- (alkyl methacrylate) pour point depresant, 0.003% of a poly-(alkyl siloxane) anti-foam agent.

EXAMPLE XIII SAE 10 mineral lubricating oil containing 1.5% of the product of Example K, 0.075% of phosphorus as the adduct obtained by heating zinc dinonylphosphorodithioate with 0.25 mole of 1,2-hexene oxide'at C., a sulfurized methyl ester of tall oil acid having a sulfur content of 15%, 6% of a polybutene viscosity index improver, 0.005% of a poly-(alkyl methacrylate) antifoam agent, and 0.5 of lard oil.

EXAMPLE XIV SAE 20 mineral lubricating oil containing 1.5% of the product of Example L, 0.5% of di-dodecyl phosphite, 2% of the sulfurized sperm oil having a sulfur content of 9%, a basic calcium detergent prepared by carbonating a mixture comprising mineral oil, calcium mahogany sulfonate and 6 moles of calcium hydroxide in the presence of an equi-molar mixture (10% of the mixture) of methyl alcohol and n-butyl alcohol as the promoter at the reflux temperature.

EXAMPLE XV SAE 10 mineral lubricating oil containing 2% of the product of Example N, 0.07% of phosphorus as Zinc di-octylphosphorodithioate, 2% of a barium detergent prepared by neutralizing with barium hydroxide the hydrolyzed reaction product of a polypropylene (molecular Weight 2000) with 1 mole of phosphorus pentasulfide and 1 mole of sulfur, 3% of a barium sulfonate detergent prepared by carbonating a mineral oil solution of mahogany acid, and a 500% stoichiometrically excess amount of barium hydroxide in the presence of phenol as the promoter at 180 C., 3% of a supplemental ashless detergent prepared by copolymerizing a mixture of 95% (Weight) of decyl-methacrylate and (weight) of diethylaminoethyl-acrylate.

EXAMPLE XVI SAE 80 mineral lubricating oil containing 2% of the I product of Example M, 0.1% of phosphorus a-s zinc din-hexylphosphorodithioate, of a chlorinated parafiin Wax having a chlorine content of 40%, 2% of di-butyl tetrasulfied, 2% of sulfurized dipentene, 0.2% of oleyl amide, 0.003% of an antifo-am agent, 0.02% of a pour point depressant, and 3% of a viscosity index improver.

EXAMPLE XVII SAE 10 mineral lubricating oil containing 3% of the product of Example 0, 0.075% of phosphorus as the zinc salt of a phosphorodithioic acid prepared by the reaction of phosphorus pentasulfide with an equimol-ar mixture of n-butyl alcohol and dodecyl alcohol, 3% of a barium detergent prepared by carbonating a mineral oil solution containing 1 mole of sperm oil, 0.6 mole of octylphenol, 2 moles of barium oxide, and a small amount of water at 150 C.

EXAMPLE XVIII SAE 20 mineral lubricating oil containing 2% of the product of Example P and 0.07% of phosphorus as zinc di-n-octylphosphorodithioate.

EXAMPLE XIX SAE 30 mineral lubricating oil containing 3% of the product of Example Q and 0.1% of phosphorus as zinc di-(isobutylphenyl)-phosphorodithioate.

EXAMPLE XX SAE 50 mineral lubricating oil containing 2% of the product of Example R.

EXAMPLE XXI SAE 90 mineral lubricating oil containing 3% of the product of Example S and 0.2% of phosphorus as the reaction product of 4 moles of turpentine with 1 mole of phosphorus pentasulfide.

EXAMPLE XXIV SAE 90 mineral lubricating oil containing 5% of the product of Example U and 1% of the calcium salt of the sulfurized phenol obtained by the reaction of 2 moles of heptylphenol with 1 mole of sulfur.

The above lubricant-s are merely illustrative and the scope of invention includes the use of all of the additives previously illustrated as well as others within the broad concept of this'invention described herein. v

The effectiveness of the nitrogenand boron-containing compositions as additives in lubricants to impart oxidation-inhibiting, corrosion-inhibiting, and detergent properties is illustrated by the results obtained from an Inh-ibi tion-Detergency Test in which a 350 cc. sample of a lubricant containing 0.001% of iron naphthenate and 1.5% by weight of the additive to be tested is heated at 300 F. for 48 hours in a 2 x 15" borosilicate tube. A clean copper-lead bearing is immersed in the lubricant along with an SAE 1020 steel test panel. Air is bubbled through the lubricant at the rate of 10 liters per hour. The oxidized sample is allowed to cool to 122 F. whereupon 0.5% (by volume) of water is added and dispersed into the sample. The sample is allowed to stand for 15 hours at room temperature and then filtered through dry No. 1 Whatman paper (double thickness) under slightly reduced pressure. The precipitant is washed With naphtha to constant Weight and reported as milligrams of sludge per 100 ml. of oil. The bearing is scrubbed with naphtha, dried, and weighed, and the bearing Weight change is reported in milligrams. The viscosity at 100 F. and 210 'F of the lubricant before and after thetest is noted. Thus,

the quantity of sludge is an indication of the ability of the additive to prevent the formation of harmful deposits; the bearing weight change is an indication of the corrosiveness of the lubricant; and the viscosity change of the lubricant is an indication of the oxidation resistance of the lubricant. The lubricant base employed in the test is a Mid-Continent, conventionally refined mineral oil having a viscosity of about 200 Saybolt Universal Seconds at 100 F. The results of the test are summarized in Table I below.

Further illustration of the usefulness of the additive of this invention in lubricants is gained from a modified version (the modification consists of extending the test period from the usual 96 hours to 144 hours) of the CRC-EX-3 engine test. This test is recognized in the field as an important test by which lubricants can be evaluated for use under light-duty service conditions.

TABLE I Viscosity increase, Bearing Sludge percent Weight (milligrams Additive (1.5% by weight of change per 109 ml.

diluent-free chemical) (milligrams) of lubricant) None. 13. 2 3. 1 53. 5 1, 145 The acylated nitrogen compositions from which the N- and B-containing additives are derived 30 10 200 10 Product of Example F. 1. 3 0.9 13. 9 1. Product of Example A. 11. 1 2. 8 +0. 9 2. Product of Example K 8. 9 2. 1 +3. 3 2. Product of Example N 11.2 4. 1 -1. 6 18. Product of Example Q 15. 2 3. 2 1. 7 0

EXAMPLE XXII SAE 90 mineral lubricating oil containing 3% of the product of Example S and 0.2% of 4,4'-methylene-bis(2,6- di-tertbutylphenol).

EXAMPLE XXIII SAE 30 mineral lubricating oil containing 2% of the product of Example U and 0.1% of phosphorus as phenylethyl di-cyclohexylphosphorodithioate.

In this particular test the lubricant is used in the crankcase of a 1954 6-cylinder Chevrolet Powerglide engine operated for 144 hours under recurring cycling conditions, each cycle consisting of 2 hours at an engine speed of 500:25 r.p.m. under 0 load and at an oil sump temperature of -125 F. and air fuel ratio of 10:1; 2 hours at an engine speed of 2500:25 r.p.m. under a load of 40 brake-horsepower and at an oil sump temperature of -170 F. and air-fuel ratio of 16:1; and 2 hours at Y 31 an engine speed of 2500:25 r.p.m. under a load of 40 brake-horsepower and at an oil sump temperature of 240-250 F. and air-fuel ratio of 16:1.

After completion of the test the engine is dismantled and various parts of the engine are examined for deposit. The lubricant is then rated according to (l) the extent of piston ring-filling, (2) the amount of sludge formed in the engine (on a scale of 80-0, 80 being indicative of no sludge and being indicative of extremely heavy sludge), and (3) the total amount of deposits, i.e., sludge and varnish, formed in the engine (on a scale of 100-0, 100 being indicative of no deposit and 0 being indicative of extremely heavy deposits). The lubricant used in the test comprises an SAE 20 mineral oil containing 1.41% by weight of the product of Example L. The lubricant is found to pass the test with the following results: ring filling, 1%; sludge rating, 75.3; total deposit rating, 93.4.

The efficacy of the nitrogenand boron-containing compositions as additives in lubricants for use under conditions of high speed and high temperature operation is shown by the results of an engine test carried out in accordance .with US. Army Ordinance tentative specification AXS-1551. This is known as the Caterpillar CRC- L-1 engine test and the particular test to which the lubricant is subjected is a modification of test, the modification consisting of the use of a fuel having a sulfur content of 1% (significantly higher than that of the specified fuel).

In this test the lubricant is used in the crankcase of the 4-stroke diesel engine having a 5%" x 8" stroke and a compression ratio of to 1 which is operated for 480 hours under the following conditions; speed, 100 r.p.m.; B.t.u. input per minute, 2900-3000; load, brake-horsepower; Water jacket outlet temperature, 175 -l80 F.; and oil temperature, 145-150 The-lubricant is evaluated in terms of (1) the piston cleanliness rating on a scale of 0100 (100 being perfectly clean and 0 representing maximum deposit) and (2) percent ring filling. A lubricant comprising an SAE 10W-30 mineral oil containing 2% by weight of the product of Example L is found to pass this test with the following result: ring filling, 19%; piston cleanliness, 96.0.

The effectiveness of the nitrogenand boron-containing compositions of this invention as additives in lubricants for internal combustion engines is evaluated further by the CRC-L-4-545 engine test. This test involves the operation of a 6-cylinder gasoline automobile engine for 36 hours under the following conditions: engine speed, 3150 r.p.m.; engine load, brake-horsepower; jacket coolant temperature, outlet 200 F., inlet 190 F.; oil sump temperature, 265 F.; and air-fuel ratio, 14.5 :1.

The lubricant is rated in terms of the weight loss of bearings, the cleanliness of the pistons and the overall varnish and sludge deposits on the various parts of the engine. By this test, a lubricant comprising an SAE 10W-30 mineral oil containing 2.08% by weight of the product of Example L is found to pass the test with the following results: piston cleanliness rating of 9.5 (10 being perfectly clean), over-all varnish and sludge rating of 96.7 (100 being perfectly clean), and an average weight loss per bearing of 2.5 milligrams.

The utility of the nitrogenand boron-containing compositions of this invention as additives in lubricants for use in two-cycle internal combustion engines illustrated by the results of an engine test in which a 7-ho-rsepower chain saw engine (McCulloch model No. 1-80) is 0perated for 25 hours under the following recurring cycling conditions, each cycle consisting of 15 minutes at zero load and 1800-2200 r.p.m. and 5 minutes at adjustable load and 5000 r.p.m. The lubricant comprises an SAE 30 mineral oil containing 7% by volume of the product of Example M and is incorporated in the fuel mixture consisting of 20 parts by volume of a leaded gasoline having an octane number of 95 and 1 part by volume of the lubricant. The lubricant is found to give by this test 32 a piston varnish rating of 7.0 (on a scale of 0-10, 10 being indicative of no varnish and 0 being indicative of extremely heavy varnish) and a crankcase cover varnish rating of 10.0 (on the same scale as above) whereas the base oil, i.e., SAE 30 mineral oil, gives a piston varnish rating of 2.5 and a crankcase cover varnish rating of 8.

The efiicacy of the nitrogenand boron-containing compositions to enhance the extreme pressure properties of other additives is shown by the results of a test carried out in accordance with US. Army Ordnance specification AXS-l569 for testing axle lubricants. This test involves the following procedure: A Chevrolet passenger car is mounted with its rear wheels on rollers and, after a short break-in period (12 minutes at 25 m.p.h. in high gear),

the engine is accelerated with full throttle to 40 m.p.h. Upon reaching 40 m.p.h. the throttle is closed completely allowing the speed to drop to 10 m.p.h. This cycle is repeated 4 times. The engine is gradually accelerated in high gear to 60 m.p.h. and at this point the throttle is opened wide and the engine accelerated to m.p.h. whereupon the throttle is closed completely allowing the speed to drop to 60 m.p.h. This drive and coast step is repeated 10 times. The rear axle lubricant is then assigned a rating based upon the apparent condition of the gear surfaces on a scale from 1 to 5 (1 indicating no scoring and 5 indicating 100% scoring). The lubricant used in the test comprises an SAE mineral lubricating oil containing the additives. The results are summarized in Table II below.

TABLE II 2.5% of the product of Example L 1 SAE 90 mineral lubricating oil+3.5% of the product of Example L 5 The efficacy of the nitrogenand boron-containing compositions of this invention to enhance the corrosion-inhibiting properties of other additives are shown by the results (Table III) of the following test: A test lubricant comprising 300 grams of an SAE 30 mineral lubricating oil containing the additives and having immersed therein bearing piece (copper-lead face, 28 grams) and blown with air at the rate of 1 cubic foot per hour at 300 F. At the end of the test the loss in weight of the bearing piece is determined; the smaller the loss, the less corrosive the lubricant.

TABLE III Additive in lubricant (percent by volume) Bearing piece loss (mg.)

3.8% of 4,4'-bis-methylene(2,6-di-tert-butylphenol) 27 0.8% of 4,4-bis-methylene(2,6-di-tert-butylphenol 26 0.8% of 4,4'-bis-methylene(2,6-di-tert-butylphenol)+3%' of the product of Example L 4 0.8% of 4,4'-bis-methylene(2,6-di-tert-butylphenol) -|2% of the product of Example L 1 0.8% of 4,4'-bis-methylene(2,6-di-tert-butylphenol)+1% of the product of Example L 0 What is claimed is:

1. A lubricating composition comprising a major proportion of a lubricating oil and a minor proportion of an oil-soluble nitrogenand boron-containing composition prepared by the process comprising forming an acylated nitrogen intermediate by the reaction at a temperature within the range of from about 80 C. to about 250 C. of an aliphatic olefin polymer-substituted succinic acidproducing compound having at least about 50 aliphatic carbon atoms in the polymer substituent with at least about one-half equivalent of an amine, for each equiv- Rating I v 33 alent of the acid-producing compound used, selected from the class consisting of alkylene amines and hydroXy-substituted alkylene amines, and reacting at a temperature between about 50 C. and about 250 C. said acylated nitrogen intermediate with a boron compound selected from the class consisting of boron oxide, boron halides, boron acids, and esters of boron acids in an amount to provide from about 0.1 atomic proportion of boron for each mole of said acylated nitrogen intermediate to about 10 atomic proportions of boron for each atomic proportion of nitrogen of said acylated nitrogen intermediate.

2. The lubricating composition of claim 1 wherein the polymer substituent of the succinic acid-producing compound is derived from a polyisobutene having an average molecular Weight within the range from about 700 to about 5000.

3. The lubricating composition of claim 1 wherein the amine is a polyethylene polyamine.

4. The lubricating composition of claim 1 wherein the boron compound is boric acid.

5. A lubricating composition comprising a major proportion of a lubricating oil and a minor proportion of an oil-soluble nitrogenand boron-containing composition prepared by the process comprising forming an acylated nitrogen intermediate by the reaction at a temperature within the range of from about 80 C. to about 250 C., of an aliphatic olefin polymer-substituted succinic acid-producing compound wherein the substituent has a molecular weight of from about 750 to about 100,- 000 and is derived from a polymer of a lower l-olefin having from 2 to 4 carbon atoms with at least about onehalf equivalent of an alkylene polyamine for each equivalent of the acid-producing compound used, and reacting at a temperature between about 50 C. and about 250 C., said acylated nitrogen intermediate with a boron compound selected from the class consisting of boron oxide, boron halides, boron acids, and esters of boron acids in an amount to provide from about 0.1 atomic proportion of boron for each mole of said acylated nitrogen inter-mediate to about 10 atomic proportions of boron for each atomic proportion of nitrogen of said acylated nitrogen intermediate.

6. The lubricating composition of claim 5 wherein the polymer substituent of the succinic acid-producing compound is derived from a polyisobutene having an average molecular weight within the range of from about 700 to about 5000.

7. The lubricating composition of claim 5 wherein the amine is a polyethylene polyamine.

8. The lubricating composition of claim 5 wherein the boron compound is boric acid.

9. The lubricating composition of claim 5 wherein the boron compound is boron trifiuoride.

10. A lubricating composition comprising a major proportion of a lubricating oiland a minor proportion of an 34 oil-soluble nitrogenand boron-containing composition prepared by the process comprising forming an acylated nitrogen intermediate by the reaction at a temperature within the range of from about C. to about 250 C.

of an isobutene polymer substituted succinic anhydride wherein the substituent has a molecular weight of from about 750 to about 5000 with at least about one-half equivalent of an ethylene polyamine having from 2 to about 6 amino groups for each equivalent of the succinic anhydride used, and reacting at a temperature between about 50 C. and about 250 C. said acylated nitrogen intermediate with boric acid in an amount to provide from about 0.1 atomic proportion of boron for each mole of said acylated nitrogen intermediate to about 10 atomic proportions of boron for each atomic proportion of nitrogen of said acylated nitrogen intermediate.

11. The lubricating composition of claim 10 wherein the isobutene polymer substituent is derived from polyisobutene.

12. The lubricating composition of claim 11 wherein the amount of the boric acid used is such as to provide from about 0.5 atomic proportion of boron for each mole of the acylated nitrogen intermediate to about 2 atomic proportions of boron for each atomic proportion of nitrogen of said acylated nitrogen intermediate.

13. A lubricating composition as in claim 1 characterized further by the presence therein of a minor proportion of a metal detergent selected from the class consisting of carbonated basic metal salts of sulfonic acids, carboxylic acids and phosphorus acids.

14. A lubricating composition as in claim 1 characterized further by the presence therein of a minor pro portion of a corrosion inhibitor selected from the class consisting of Group II metal phosphorodithioates, re-

action products of a Group II metal phosphorodithioate with an epoxide, and hindered phenols.

15. A lubricating composition as in claim 1 characterized further by the presence therein of a minor proportion of a zinc diakyl phosphorodithioate.

References Cited by the Examiner UNITED STATES PATENTS 2,459,597 1/ 1949 Stillson et al. 252-52 2,956,018 10/1960 Carlyle et al. 25232.7 3,000,916 9/1961 Klass et al.

3,018,250 1/1962 Anderson et al. 252-51.5 3,018,291 1/1962 Anderson et al. 25251.5

FOREIGN PATENTS 819,169 8/ 1959 Great Britain. 874,877 8/ 1961 Great Britain.

DANIEL E. WYMAN, Primary Examiner.

J. R. SEILER, L. G. XIARHOS, Assistant Examiners.

Claims (2)

1. A LUBRICATING COMPOSITION COMPRISING A MAJOR PROPORTION OF A LUBRICATING OIL AND A MINOR PROPORTION OF AN OIL-SOLUBLE NITROGEN- AND BORON-CONTAINING COMPOSITION PREPARED BY THE PROCESS COMPRISING FORMING AN ACYLATED NITROGEN INTERMEDIATE BY THE REACTION AT A TEMPERATURE WITHIN THE RANGE OF FROM ABOUT 80*C. TO ABOUT 250*C. OF AN ALIPHATIC OLEFIN POLYMER-SUBSTITUTED SUCCINIC ACIDPRODUCING COMPOUND HAVING AT LEAST ABOUT 50 ALIPHATIC CARBON ATOMS IN THE POLYMER SUBSTITUENT WITH AT LEAST ABOUT ONE-HALF EQUIVALENT OF AN AMINE, FOR EACH EQUIVALENT OF THE ACID-PRODUCING COMPOUND USED, SELECTED FROM THE CLASS CONSISTING OF ALKYLENE AMINES AND HYDROXY-SUBSTITUTED ALKYLENE AMINES, AND REACTING AT A TEMPERATURE BETWEEN ABOUT 50*C. AND ABOUT 250*C. SAID ACYLATED NITROGEN INTERMEDIATE WITH A BORON COMPOUND SELECTED FROM THE CLASS CONSISTING OF BORON OXIDE, BORON HALIDES, BORON ACIDS, AND ESTERS OF BORON ACIDS IN AN AMOUNT TO PROVIDE FROM ABOUT 0.1 ATOMIC PROPORTION OF BORON FOR EACH MOLE OF SAID ACYLATED NITROGEN INTERMEDIATE TO ABOUT 10 ATOMIC PRPORTIONS OF BORON FOR EACH ATOMIC PROPORTION OF NITROGEN OF SAID ACYLATED NITROGEN INTERMEDIATE.
14. A LUBRICATING COMPOSITION AS IN CLAIM 1 CHARACTERIZED FURTHER BY THE PRESENCE THEREIN OF A MINOR PROPORTION OF A CORROSION INHIBITOR SELECTED FROM THE CLASS CONSISTING OF GROUP II METAL PHOSPHORODITHIOATES, REACTION PRODUCTS OF A GROUP II METAL PHOSPHORODITHIOATE WITH AN EPOXIDE, AND HINDERED PHENOLS.
US3254025A 1961-08-18 1962-04-06 Boron-containing acylated amine and lubricating compositions containing the same Expired - Lifetime US3254025A (en)

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US3087936A US3087936A (en) 1961-08-18 1961-08-18 Reaction product of an aliphatic olefinpolymer-succinic acid producing compound with an amine and reacting the resulting product with a boron compound
US3254025A US3254025A (en) 1961-08-18 1962-04-06 Boron-containing acylated amine and lubricating compositions containing the same

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US3087936A US3087936A (en) 1961-08-18 1961-08-18 Reaction product of an aliphatic olefinpolymer-succinic acid producing compound with an amine and reacting the resulting product with a boron compound
US3254025A US3254025A (en) 1961-08-18 1962-04-06 Boron-containing acylated amine and lubricating compositions containing the same
GB3134362A GB1021182A (en) 1961-08-18 1962-08-15 Oil-soluble nitrogen containing products and process for preparing same
GB3919665A GB1021183A (en) 1961-08-18 1962-08-15 Oil-soluble nitrogen-containing products and process for preparing same
DE1962L0042737 DE1274776B (en) 1961-08-18 1962-08-17 oil we
FR907156A FR1439820A (en) 1961-08-18 1962-08-17 A method of manufacturing compositions containing nitrogen and boron, soluble in oils
DE19621644907 DE1644907A1 (en) 1961-08-18 1962-08-17 oil we
JP6763364A JPS4936926B1 (en) 1961-08-18 1964-12-03
FR87407E FR87407E (en) 1961-08-18 1965-01-08 A method of manufacturing compositions containing nitrogen and boron, soluble in oils
JP1143269A JPS4833242B1 (en) 1961-08-18 1969-02-15

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Cited By (335)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3338832A (en) * 1963-04-29 1967-08-29 Lubrizol Corp Lubricating oil containing reaction product of certain acylated nitrogen containing intermediates and a boron compound
US3344069A (en) * 1965-07-01 1967-09-26 Lubrizol Corp Lubricant additive and lubricant containing same
US3442808A (en) * 1966-11-01 1969-05-06 Standard Oil Co Lubricating oil additives
US3533945A (en) * 1963-11-13 1970-10-13 Lubrizol Corp Lubricating oil composition
US3929650A (en) * 1974-03-22 1975-12-30 Chevron Res Extreme pressure agent and its preparation
US4116876A (en) * 1977-01-28 1978-09-26 Exxon Research & Engineering Co. Borated oxazolines as varnish inhibiting dispersants in lubricating oils
FR2404668A1 (en) * 1977-10-03 1979-04-27 Exxon Research Engineering Co A lubricating oil composition mixed with a polyol ester and imide
US4295983A (en) * 1980-06-12 1981-10-20 Ethyl Corporation Lubricating oil composition containing boronated N-hydroxymethyl succinimide friction reducers
EP0039998A1 (en) 1980-05-08 1981-11-18 Exxon Research And Engineering Company Lubricating oil composition containing sediment-reducing additive
US4328113A (en) * 1980-01-14 1982-05-04 Mobil Oil Corporation Friction reducing additives and compositions thereof
DE3132220A1 (en) * 1980-08-25 1982-05-13 Exxon Research Engineering Co Kind of oil with improved dispersibility in diesel engines
US4331545A (en) * 1979-04-19 1982-05-25 Edwin Cooper, Inc. Lubricating compositions containing boronated N-alkanol hydrocarbylamide
US4374033A (en) * 1981-06-18 1983-02-15 Edwin Cooper, Inc. Dispersant and lubricating oil containing the dispersant
EP0090629A2 (en) * 1982-03-29 1983-10-05 Amoco Corporation Borated lube oil additive
US4455243A (en) * 1983-02-24 1984-06-19 Chevron Research Company Succinimide complexes of borated fatty acid esters of glycerol and lubricating oil compositions containing same
EP0113582A2 (en) * 1982-12-27 1984-07-18 Exxon Research And Engineering Company Macrocyclic polyamine and polycyclic polyamine multifunctional lubricating oil additives
FR2541685A1 (en) * 1983-02-24 1984-08-31 Chevron Res A lubricating oil composition containing a succinimide of fatty acid ester of glycerol borate complex
EP0132383A2 (en) * 1983-07-25 1985-01-30 Amoco Corporation Boration of polyamine dispersants with polyborate esters
US4505829A (en) * 1980-05-08 1985-03-19 Exxon Research & Engineering Co. Lubricating oil composition containing sediment-reducing additive
US4529526A (en) * 1982-11-30 1985-07-16 Honda Motor Co., Ltd. Lubricating oil composition
WO1986004601A1 (en) 1985-01-31 1986-08-14 The Lubrizol Corporation Sulfur-containing compositions, and additive concentrates and lubricating oils containing same
EP0208560A2 (en) * 1985-07-11 1987-01-14 Exxon Chemical Patents Inc. Oil-soluble dispersant additives in fuels and lubricating oils
US4749505A (en) * 1985-07-08 1988-06-07 Exxon Chemical Patents Inc. Olefin polymer viscosity index improver additive useful in oil compositions
US4801390A (en) * 1984-06-05 1989-01-31 Exxon Research & Engineering Co. Lubricating compositions
US4842755A (en) * 1986-02-04 1989-06-27 Exxon Chemical Patents Inc. Marine lubricating composition
US4855074A (en) * 1988-03-14 1989-08-08 Ethyl Petroleum Additives, Inc. Homogeneous additive concentrates and their formation
US4863624A (en) * 1987-09-09 1989-09-05 Exxon Chemical Patents Inc. Dispersant additives mixtures for oleaginous compositions
US4866141A (en) * 1986-10-07 1989-09-12 Exxon Chemical Patents Inc. Lactone modified, esterfied or aminated additives useful in oleaginous compositions and compositions containing same
US4873009A (en) * 1982-03-29 1989-10-10 Amoco Corporation Borated lube oil additive
US4873004A (en) * 1986-11-28 1989-10-10 Shell Oil Company Lubricating composition
JPH01502987A (en) * 1986-06-13 1989-10-12
EP0351964A1 (en) 1988-06-24 1990-01-24 Exxon Chemical Patents Inc. Synergistic combination of additives useful in power transmitting compositions
GB2183243B (en) * 1985-10-09 1990-01-24 Nippon Oil Co Ltd Process for preparing oil-soluble nitrogen-containing compounds
US4948522A (en) * 1988-02-23 1990-08-14 Exxon Chemical Patents Inc. Dispersant for marine diesel cylinder lubricant
US4954277A (en) * 1986-10-07 1990-09-04 Exxon Chemical Patents Inc. Lactone modified, esterified or aminated additives useful in oleaginous compositions and compositions containing same
EP0399764A1 (en) 1989-05-22 1990-11-28 Ethyl Petroleum Additives Limited Lubricant compositions
US4981492A (en) * 1989-12-13 1991-01-01 Mobil Oil Corporation Borated triazole-substituted polyalkenyl succinimides as multifunctional lubricant and fuel additives
US5024677A (en) * 1990-06-11 1991-06-18 Nalco Chemical Company Corrosion inhibitor for alcohol and gasohol fuels
US5110488A (en) * 1986-11-24 1992-05-05 The Lubrizol Corporation Lubricating compositions containing reduced levels of phosphorus
US5118432A (en) * 1985-07-11 1992-06-02 Exxon Chemical Patents Inc. Dispersant additive mixtures for oleaginous compositions
US5162526A (en) * 1976-09-24 1992-11-10 Exxon Chemical Patents Inc. Macrocyclic polyamine and polycyclic polyamine multifunctional lubricating oil
US5164103A (en) * 1988-03-14 1992-11-17 Ethyl Petroleum Additives, Inc. Preconditioned atf fluids and their preparation
US5176840A (en) * 1990-02-16 1993-01-05 Ethyl Petroleum Additives, Inc. Gear oil additive composition and gear oil containing the same
US5185090A (en) * 1988-06-24 1993-02-09 Exxon Chemical Patents Inc. Low pressure derived mixed phosphorous- and sulfur-containing reaction products useful in power transmitting compositions and process for preparing same
US5198133A (en) * 1988-03-14 1993-03-30 Ethyl Petroleum Additives, Inc. Modified succinimide or sucinamide dispersants and their production
US5211834A (en) * 1992-01-31 1993-05-18 Betz Laboratories, Inc. Method for controlling fouling deposit formation in a liquid hydrocarbonaceous medium using boronated derivatives of polyalkenylsuccinimides
US5225093A (en) * 1990-02-16 1993-07-06 Ethyl Petroleum Additives, Inc. Gear oil additive compositions and gear oils containing the same
US5227082A (en) * 1991-12-23 1993-07-13 Exxon Research And Engineering Company Lubricating oil having improved rust inhibition and demulsibility
US5232616A (en) * 1990-08-21 1993-08-03 Chevron Research And Technology Company Lubricating compositions
US5242612A (en) * 1988-06-24 1993-09-07 Exxon Chemical Patents Inc. Mixed phosphorous- and sulfur-containing reaction products useful in power transmitting compositions
EP0558835A1 (en) 1992-01-30 1993-09-08 Albemarle Corporation Biodegradable lubricants and functional fluids
US5314633A (en) * 1988-06-24 1994-05-24 Exxon Chemical Patents Inc. Low pressure derived mixed phosphorous- and sulfur- containing reaction products useful in power transmitting compositions and process for preparing same
US5320768A (en) * 1988-06-24 1994-06-14 Exxon Chemical Patents Inc. Hydroxy ether amine friction modifier for use in power transmission fluids and anti-wear additives for use in combination therewith
US5326487A (en) * 1988-06-24 1994-07-05 Exxon Chemical Patents Inc. Mixed phosphorous- and sulfur- containing reaction products useful in power transmitting compositions
US5328619A (en) * 1991-06-21 1994-07-12 Ethyl Petroleum Additives, Inc. Oil additive concentrates and lubricants of enhanced performance capabilities
US5330667A (en) * 1992-04-15 1994-07-19 Exxon Chemical Patents Inc. Two-cycle oil additive
US5334329A (en) * 1988-10-07 1994-08-02 The Lubrizol Corporation Lubricant and functional fluid compositions exhibiting improved demulsibility
US5340369A (en) * 1991-05-13 1994-08-23 The Lubrizol Corporation Diesel fuels containing organometallic complexes
US5344467A (en) * 1991-05-13 1994-09-06 The Lubrizol Corporation Organometallic complex-antioxidant combinations, and concentrates and diesel fuels containing same
US5360459A (en) * 1991-05-13 1994-11-01 The Lubrizol Corporation Copper-containing organometallic complexes and concentrates and diesel fuels containing same
US5376154A (en) * 1991-05-13 1994-12-27 The Lubrizol Corporation Low-sulfur diesel fuels containing organometallic complexes
US5389273A (en) * 1988-03-14 1995-02-14 Ethyl Petroleum Additives, Inc. Modified succinimide or succinamide dispersants and their production
US5439606A (en) * 1988-03-14 1995-08-08 Ethyl Petroleum Additives, Inc. Modified succinimide or succinamide dispersants and their production
EP0683220A2 (en) 1994-05-18 1995-11-22 Ethyl Corporation Lubricant additive compositions
WO1995034615A1 (en) * 1994-06-16 1995-12-21 Exxon Chemical Limited Multigrade lubricating compositions containing no viscosity modifier
EP0695798A2 (en) 1994-08-03 1996-02-07 The Lubrizol Corporation Lubricating compositions, concentrates, and greases containing the combination of an organic polysulfide and an overbased composition or a phosphorus or boron compound
US5518510A (en) * 1991-05-13 1996-05-21 The Lubrizol Corporation Low-sulfur diesel fuels containing organo-metallic complexes
EP0713907A2 (en) 1994-09-26 1996-05-29 Ethyl Petroleum Additives Limited Zinc additives of enhanced performance capabilities
EP0713908A1 (en) 1994-11-22 1996-05-29 Ethyl Corporation Power transmission fluids
US5534170A (en) * 1988-06-24 1996-07-09 Exxon Chemical Patents Inc. Mixed phosphorus- and sulfur-containing reaction products useful in power transmitting compositions
US5554310A (en) * 1992-12-17 1996-09-10 Exxon Chemical Patents Inc. Trisubstituted unsaturated polymers
US5558802A (en) * 1995-09-14 1996-09-24 Exxon Chemical Patents Inc Multigrade crankcase lubricants with low temperature pumpability and low volatility
WO1996037582A1 (en) * 1994-05-20 1996-11-28 Exxon Research And Engineering Company Lubricating oil composition
US5629434A (en) * 1992-12-17 1997-05-13 Exxon Chemical Patents Inc Functionalization of polymers based on Koch chemistry and derivatives thereof
FR2741890A1 (en) * 1995-12-01 1997-06-06 Ethyl Petroleum Additives Ltd Dispersants for diesel engines compatible with seals
US5643859A (en) * 1992-12-17 1997-07-01 Exxon Chemical Patents Inc. Derivatives of polyamines with one primary amine and secondary of tertiary amines
US5646332A (en) * 1992-12-17 1997-07-08 Exxon Chemical Patents Inc. Batch Koch carbonylation process
US5650536A (en) * 1992-12-17 1997-07-22 Exxon Chemical Patents Inc. Continuous process for production of functionalized olefins
US5652202A (en) * 1995-08-15 1997-07-29 Exxon Chemical Patents Inc. Lubricating oil compositions
US5652201A (en) * 1991-05-29 1997-07-29 Ethyl Petroleum Additives Inc. Lubricating oil compositions and concentrates and the use thereof
US5658862A (en) * 1994-12-20 1997-08-19 Exxon Research And Engineering Company Engine oil with improved fuel economy properties (law372).
US5756428A (en) * 1986-10-16 1998-05-26 Exxon Chemical Patents Inc. High functionality low molecular weight oil soluble dispersant additives useful in oleaginous composition
US5767044A (en) * 1993-08-20 1998-06-16 The Lubrizol Corporation Lubricating compositions with improved thermal stability and limited slip performance
US5767046A (en) * 1994-06-17 1998-06-16 Exxon Chemical Company Functionalized additives useful in two-cycle engines
WO1998047989A1 (en) 1997-04-21 1998-10-29 Exxon Chemical Patents Inc. Power transmission fluids containing alkyl phosphonates
WO1999036491A1 (en) 1998-01-13 1999-07-22 Exxon Chemical Patents Inc. Automatic transmission fluids of improved viscometric properties
US5942470A (en) * 1990-05-17 1999-08-24 Ethyl Petroleum Additives, Inc. Lubricant compositions
US6001780A (en) * 1998-06-30 1999-12-14 Chevron Chemical Company Llc Ashless lubricating oil formulation for natural gas engines
US6028210A (en) * 1997-12-18 2000-02-22 Exxon Chemical Patents, Inc. Process for making sulfur boron antiwear agents for lubricating compositions
US6042626A (en) * 1997-08-01 2000-03-28 Ethyl Corporation Phosphorylated and/or boronated dispersants as thermal stability additives for distillate fuels
US6121209A (en) * 1994-12-09 2000-09-19 Exxon Chemical Patents Inc Synergistic antioxidant systems
US6306802B1 (en) 1994-09-30 2001-10-23 Exxon Chemical Patents Inc. Mixed antioxidant composition
US6362136B1 (en) 1994-05-23 2002-03-26 The Lubrizol Corporation Compositions for extending seal life, and lubricants and functional fluids containing the same
US6361573B1 (en) * 1999-08-31 2002-03-26 Ethyl Corporation Fuel dispersants with enhanced lubricity
US6423670B2 (en) 2000-03-20 2002-07-23 Infineum International Ltd. Lubricating oil compositions
US6489271B1 (en) 1994-08-03 2002-12-03 The Lubrizol Corporation Combination of a sulfur compound and specific phosphorus compounds and their use in lubricating compositions, concentrates and greases
US20020193650A1 (en) * 2001-05-17 2002-12-19 Goze Maria Caridad B. Low noack volatility poly alpha-olefins
US6573223B1 (en) 2002-03-04 2003-06-03 The Lubrizol Corporation Lubricating compositions with good thermal stability and demulsibility properties
US6613722B1 (en) * 1997-03-07 2003-09-02 Exxon Chemical Patents Inc. Lubricating composition
US20030173251A1 (en) * 2000-12-22 2003-09-18 Antonio Gutierrez Hydroxy aromatic mannich base condensation products and the use thereof as soot dispersants in lubricating oil compositions
US6624123B2 (en) * 1997-04-11 2003-09-23 Chevron Chemical S.A. Use of surfactants with high molecular weight for improving the filterability in hydraulic lubricants
US6627584B2 (en) 2002-01-28 2003-09-30 Ethyl Corporation Automatic transmission fluid additive comprising reaction product of hydrocarbyl acrylates and dihydrocarbyldithiophosphoric acids
WO2003095595A1 (en) 2002-05-09 2003-11-20 The Lubrizol Corporation Continuously variable transmission fluids comprising a combination of calcium- and magnesium-overbased detergents
US20030220206A1 (en) * 2000-09-29 2003-11-27 Nippon Mitsubishi Oil Corporation Lubricant compositions
US6677281B2 (en) 2001-04-20 2004-01-13 Exxonmobil Research And Engineering Company Synergistic combination of metallic and ashless rust inhibitors to yield improved rust protection and demulsibility in dispersant-containing lubricants
US6689723B2 (en) 2002-03-05 2004-02-10 Exxonmobil Chemical Patents Inc. Sulfide- and polysulfide-containing lubricating oil additive compositions and lubricating compositions containing the same
US20040033908A1 (en) * 2002-08-16 2004-02-19 Deckman Douglas E. Functional fluid lubricant using low Noack volatility base stock fluids
US6734148B2 (en) 2001-12-06 2004-05-11 Infineum International Ltd. Dispersants and lubricating oil compositions containing same
US6743757B2 (en) 2001-12-06 2004-06-01 Infineum International Ltd. Dispersants and lubricating oil compositions containing same
US20040147410A1 (en) * 2003-01-15 2004-07-29 Milner Jeffrey L Extended drain, thermally stable, gear oil formulations
US20040260027A1 (en) * 2003-06-20 2004-12-23 Michaud Vincent Jean Marie Process for forming polyalkenyl acylating agents
US20040260032A1 (en) * 2003-06-20 2004-12-23 Irving Matthew David Low sediment process for thermally reacting highly reactive polymers and enophiles
US6855675B1 (en) * 1995-05-24 2005-02-15 Tonengeneral Sekiyu K.K. Lubricating oil composition
US20050065043A1 (en) * 2003-09-23 2005-03-24 Henly Timothy J. Power transmission fluids having extended durability
US20050070446A1 (en) * 2003-09-25 2005-03-31 Ethyl Petroleum Additives, Inc. Boron free automotive gear oil
US20050101497A1 (en) * 2003-11-12 2005-05-12 Saathoff Lee D. Compositions and methods for improved friction durability in power transmission fluids
US20050101494A1 (en) * 2003-11-10 2005-05-12 Iyer Ramnath N. Lubricant compositions for power transmitting fluids
EP1568759A2 (en) 2004-02-27 2005-08-31 Afton Chemical Corporation Power transmission fluids
US20050202979A1 (en) * 2004-03-10 2005-09-15 Ethyl Petroleum Additives, Inc. Power transmission fluids with enhanced extreme pressure characteristics
US20050250656A1 (en) * 2004-05-04 2005-11-10 Masahiro Ishikawa Continuously variable transmission fluid
US20050255251A1 (en) * 2004-05-17 2005-11-17 Hodge Robert L Composition, method of making, and treatment of wood with an injectable wood preservative slurry having biocidal particles
US20060003905A1 (en) * 2004-07-02 2006-01-05 Devlin Cathy C Additives and lubricant formulations for improved corrosion protection
US20060025314A1 (en) * 2004-07-28 2006-02-02 Afton Chemical Corporation Power transmission fluids with enhanced extreme pressure and antiwear characteristics
EP1640440A1 (en) 2004-09-22 2006-03-29 Infineum International Limited Friction and/or wear reduction in manual or automated manual transmissions
US20060075923A1 (en) * 2004-10-12 2006-04-13 Richardson H W Method of manufacture and treatment of wood with injectable particulate iron oxide
US20060122073A1 (en) * 2004-12-08 2006-06-08 Chip Hewette Oxidation stable gear oil compositions
US20060173217A1 (en) * 2005-01-28 2006-08-03 Abbas Kadkhodayan Seal swell agent and process therefor
WO2006094011A2 (en) 2005-03-01 2006-09-08 R.T. Vanderbilt Company, Inc. Molybdenum dialkyldithiocarbamate compositions and lubricating compositions containing the same
US20060217273A1 (en) * 2005-03-23 2006-09-28 Nubar Ozbalik Lubricating compositions
US20060223716A1 (en) * 2005-04-04 2006-10-05 Milner Jeffrey L Tractor fluids
US20060252660A1 (en) * 2005-05-09 2006-11-09 Akhilesh Duggal Hydrolytically stable viscosity index improves
US20060264339A1 (en) * 2005-05-19 2006-11-23 Devlin Mark T Power transmission fluids with enhanced lifetime characteristics
EP1728848A1 (en) 2005-06-01 2006-12-06 Infineum International Limited Use of unsaturated olefin polymers to improve the compatibility between nitrile rubber seals and lubricating oil compositions
US20070004603A1 (en) * 2005-06-30 2007-01-04 Iyer Ramnath N Methods for improved power transmission performance and compositions therefor
US20070000745A1 (en) * 2005-06-30 2007-01-04 Cameron Timothy M Methods for improved power transmission performance
US20070042917A1 (en) * 2005-07-12 2007-02-22 Ramanathan Ravichandran Amine Tungstates and Lubricant Compositions
US20070042916A1 (en) * 2005-06-30 2007-02-22 Iyer Ramnath N Methods for improved power transmission performance and compositions therefor
US20070078066A1 (en) * 2005-10-03 2007-04-05 Milner Jeffrey L Lubricant formulations containing extreme pressure agents
US20070105728A1 (en) * 2005-11-09 2007-05-10 Phillips Ronald L Lubricant composition
US20070111906A1 (en) * 2005-11-12 2007-05-17 Milner Jeffrey L Relatively low viscosity transmission fluids
US20070142660A1 (en) * 2005-11-09 2007-06-21 Degonia David J Salt of a sulfur-containing, phosphorus-containing compound, and methods thereof
US20070142237A1 (en) * 2005-11-09 2007-06-21 Degonia David J Lubricant composition
US20070142659A1 (en) * 2005-11-09 2007-06-21 Degonia David J Sulfur-containing, phosphorus-containing compound, its salt, and methods thereof
WO2007111741A2 (en) * 2005-12-15 2007-10-04 The Lubrizol Corporation Lubricant composition for a final drive axle
US20070259016A1 (en) * 2006-05-05 2007-11-08 Hodge Robert L Method of treating crops with submicron chlorothalonil
US20070259792A1 (en) * 2006-03-22 2007-11-08 Null Volker K Functional fluid compositions
US20070270317A1 (en) * 2006-05-19 2007-11-22 Milner Jeffrey L Power Transmission Fluids
US20080015127A1 (en) * 2006-07-14 2008-01-17 Loper John T Boundary friction reducing lubricating composition
US20080015125A1 (en) * 2006-07-14 2008-01-17 Devlin Mark T Lubricant compositions
US20080015124A1 (en) * 2006-07-14 2008-01-17 Devlin Mark T Lubricant composition
WO2008013698A1 (en) 2006-07-21 2008-01-31 Exxonmobil Research And Engineering Company Method for lubricating heavy duty geared apparatus
US20080051305A1 (en) * 2006-08-28 2008-02-28 Devlin Mark T Lubricant composition
US20080119377A1 (en) * 2006-11-22 2008-05-22 Devlin Mark T Lubricant compositions
US20080182768A1 (en) * 2007-01-31 2008-07-31 Devlin Cathy C Lubricant composition for bio-diesel fuel engine applications
EP1959003A2 (en) 2007-02-08 2008-08-20 Infineum International Limited Soot dispersants and lubricating oil compositions containing same
US20080213608A1 (en) * 2004-10-08 2008-09-04 Richardson Hugh W Milled Submicron Chlorothalonil With Narrow Particle Size Distribution, and Uses Thereof
EP1970430A2 (en) 2007-03-09 2008-09-17 Afton Chemical Corporation Fuel composition containing a hydrocarbyl-substituted succinimide
US20080274921A1 (en) * 2007-05-04 2008-11-06 Ian Macpherson Environmentally-Friendly Lubricant Compositions
WO2008154334A1 (en) 2007-06-08 2008-12-18 Infineum International Limited Additives and lubricating oil compositions containing same
US20090005277A1 (en) * 2007-06-29 2009-01-01 Watts Raymond F Lubricating Oils Having Improved Friction Stability
US20090005276A1 (en) * 2007-06-29 2009-01-01 Watts Raymond F Boron-Containing Lubricating Oils Having Improved Friction Stability
US20090011963A1 (en) * 2007-07-06 2009-01-08 Afton Chemical Corporation Truck fleet fuel economy by the use of optimized engine oil, transmission fluid, and gear oil
US20090029888A1 (en) * 2005-07-12 2009-01-29 Ramanathan Ravichandran Amine tungstates and lubricant compositions
US20090031614A1 (en) * 2007-08-01 2009-02-05 Ian Macpherson Environmentally-Friendly Fuel Compositions
EP2025737A1 (en) 2007-08-01 2009-02-18 Afton Chemical Corporation Environmentally-friendly fuel compositions
US20090071067A1 (en) * 2007-09-17 2009-03-19 Ian Macpherson Environmentally-Friendly Additives And Additive Compositions For Solid Fuels
EP2042582A2 (en) 2007-09-24 2009-04-01 Afton Chemical Corporation Surface passivation and to methods for the reduction of fuel thermal degradation deposits
WO2009045979A1 (en) 2007-10-03 2009-04-09 The Lubrizol Corporation Lubricants that decrease micropitting for industrial gears
US20090143478A1 (en) * 2004-10-08 2009-06-04 Phibrowood, Llc Milled Submicron Organic Biocides With Narrow Particle Size Distribution, and Uses Thereof
US20090156449A1 (en) * 2007-12-12 2009-06-18 Rowland Robert G Alkylated 1,3-benzenediamine compounds and methods for producing same
US20090156441A1 (en) * 2007-12-12 2009-06-18 Rowland Robert G Cycloalkyl phenylenediamines as deposit control agents for lubricants
EP2075264A1 (en) 2007-12-26 2009-07-01 Infineum International Limited Method of forming polyalkene substituted carboxylic acid compositions
EP2075315A1 (en) 2007-12-12 2009-07-01 Infineum International Limited Additive Compositions with Michael adducts of N-substituted phenylenediamines
EP2083063A1 (en) 2008-01-22 2009-07-29 Infineum International Limited Lubricating oil composition
EP2083024A1 (en) 2008-01-24 2009-07-29 Afton Chemical Corporation Olefin copolymer dispersant VI improver and lubricant compositions and uses thereof
EP2090642A1 (en) 2008-02-08 2009-08-19 Infineum International Limited Engine lubrication
US20090223408A1 (en) * 2004-05-17 2009-09-10 Phibrowood, Llc Use of Sub-Micron Copper Salt Particles in Wood Preservation
US20090233822A1 (en) * 2008-03-11 2009-09-17 Afton Chemical Corporation Ultra-low sulfur clutch-only transmission fluids
DE102009001301A1 (en) 2008-03-11 2009-09-24 Audi Ag A method for lubricating a component for the clutch of an automatic transmission which requires lubrication
DE102009012567A1 (en) 2008-03-11 2009-10-01 Afton Chemical Corp. Clutch-only transmission fluid useful for lubrication comprises oil formulated with additive components having metal detergent, phosphorus-based wear preventative, phosphorylated and boronated dispersant, sulfurized extreme pressure agent
WO2009119831A1 (en) 2008-03-28 2009-10-01 富士フイルム株式会社 Composition and method for forming coating film
EP2107102A2 (en) 2008-04-04 2009-10-07 Afton Chemical Corporation A succinimide lubricity additive for diesel fuel
EP2116590A1 (en) 2005-02-18 2009-11-11 Infineum International Limited Soot dispersants and lubricating oil compositions containing same
US20090280185A1 (en) * 2003-06-17 2009-11-12 Phibrowood, Llc Particulate wood preservative and method for producing the same
DE202009013309U1 (en) 2009-10-05 2010-03-04 Afton Chemical Corp. Fuel and fuel compositions
EP2161326A1 (en) 2008-09-05 2010-03-10 Infineum International Limited Lubricating oil compositions
EP2163602A1 (en) 2008-09-05 2010-03-17 Infineum International Limited A lubricating oil composition
US20100075876A1 (en) * 2008-09-24 2010-03-25 David John Claydon Fuel compositions
EP2169034A2 (en) 2009-10-05 2010-03-31 Afton Chemical Corporation Fuel compositions
WO2010077630A1 (en) 2008-12-09 2010-07-08 The Lubrizol Corporation Lubricating composition containing a compound derived from a hydroxy-carboxylic acid
EP2206764A1 (en) 2008-12-23 2010-07-14 Infineum International Limited Aniline compounds as ashless TBN sources and lubricating oil compositions containing same
EP2233554A1 (en) 2009-03-27 2010-09-29 Infineum International Limited Lubricating oil compositions
EP2236590A1 (en) 2009-04-01 2010-10-06 Infineum International Limited Lubricating oil composition
EP2239314A1 (en) 2009-04-06 2010-10-13 Infineum International Limited Lubricating oil composition
EP2272940A1 (en) 2001-09-14 2011-01-12 Afton Chemical Intangibles LLC Fuels compositions for direct injection gasoline engines
US20110010985A1 (en) * 2007-05-22 2011-01-20 Peter Wangqi Hou Fuel Additive to Control Deposit Formation
EP2290038A2 (en) 2009-08-24 2011-03-02 Infineum International Limited A lubricating oil composition
EP2290041A2 (en) 2009-08-24 2011-03-02 Infineum International Limited A lubricating oil composition
EP2290043A1 (en) 2009-08-24 2011-03-02 Infineum International Limited A lubricating oil composition comprising metal dialkyldithiophosphate and carbodiimide
WO2011025636A1 (en) 2009-08-28 2011-03-03 Chemtura Corporation Two-stage process and system for forming high viscosity polyalphaolefins
WO2011026990A1 (en) 2009-09-07 2011-03-10 Shell Internationale Research Maatschappij B.V. Lubricating compositions
WO2011034829A1 (en) 2009-09-16 2011-03-24 The Lubrizol Corporation Lubricating composition containing an ester
EP2302023A2 (en) 2002-10-04 2011-03-30 R.T. Vanderbilt Company, Inc. Synergistic organoborate compositions and lubricating compositions containing same
US20110092401A1 (en) * 2003-04-25 2011-04-21 Buitrago Juan A Gear oil having low copper corrosion properties
US20110105371A1 (en) * 2009-11-05 2011-05-05 Afton Chemical Corporation Olefin copolymer vi improvers and lubricant compositions and uses thereof
EP2319904A1 (en) 2009-10-29 2011-05-11 Infineum International Limited Lubrication and lubricating oil compositions comprising phenylene diamines
WO2011059583A1 (en) 2009-10-29 2011-05-19 Chemtura Corporation Lubrication and lubricating oil compositions
WO2011066142A1 (en) 2009-11-30 2011-06-03 The Lubrizol Corporation Stabilized blends containing friction modifiers
WO2011102836A1 (en) 2010-02-19 2011-08-25 Infineum International Limited Wet friction clutch-lubricant systems providing high dynamic coefficients of friction through the use of borated detergents
WO2011102835A1 (en) 2010-02-19 2011-08-25 Toyota Jidosha Kabushiki Kaisha Wet friction clutch-lubricant systems providing high dynamic coefficients of friction through the use of sodium detergents
EP2363454A1 (en) 2010-02-23 2011-09-07 Infineum International Limited A lubricating oil composition
EP2366761A1 (en) 2010-03-09 2011-09-21 Infineum International Limited Morpholine derivatives as ashless TBN sources and lubricating oil compositions containing same
EP2371932A1 (en) 2010-04-01 2011-10-05 Infineum International Limited A lubricating oil composition
EP2371934A1 (en) 2010-03-31 2011-10-05 Infineum International Limited Lubricating oil composition
EP2374866A1 (en) 2010-04-06 2011-10-12 Infineum International Limited A lubricating oil composition comprising alkoxylated phenol-formaldehyde condensate
WO2011130142A1 (en) 2010-04-15 2011-10-20 The Lubrizol Corporation Low-ash lubricating oils for diesel engines
WO2011143418A1 (en) 2010-05-12 2011-11-17 Exxonmobil Research And Engineering Company Method for reducing one or more of deposits and friction of a lubricating oil
EP2390306A1 (en) 2009-12-01 2011-11-30 Infineum International Limited A lubricating oil composition
WO2011149810A1 (en) 2010-05-24 2011-12-01 The Lubrizol Corporation Lubricating composition
EP2420552A1 (en) 2010-08-19 2012-02-22 Infineum International Limited EGR Equipped Diesel Engines and Lubricating Oil Compositions
US8158208B2 (en) 2004-05-17 2012-04-17 Osmose, Inc. Method of preserving wood by injecting particulate wood preservative slurry
EP2453000A1 (en) 2010-11-08 2012-05-16 Infineum International Limited Lubricating Oil Composition comprising a hydrogenated imide derived from a Diels-Alder adduct of maleic anhydride and a furan
EP2457984A1 (en) 2010-11-30 2012-05-30 Infineum International Limited A lubricating oil composition
EP2479245A1 (en) 2011-01-19 2012-07-25 Afton Chemical Corporation Fuel additives and gasoline containing the additives
WO2012141855A1 (en) 2011-04-15 2012-10-18 R.T. Vanderbilt Company, Inc. Molybdenum dialkyldithiocarbamate compositions and lubricating compositions containing the same
US8299003B2 (en) 2005-11-09 2012-10-30 Afton Chemical Corporation Composition comprising a sulfur-containing, phosphorus-containing compound, and/or its salt, and uses thereof
WO2012162027A1 (en) 2011-05-26 2012-11-29 The Lubrizol Corporation Stabilized blends containing friction modifiers
WO2012162020A1 (en) 2011-05-26 2012-11-29 The Lubrizol Corporation Stabilized blends containing antioxidants
WO2013003405A1 (en) 2011-06-30 2013-01-03 Exxonmobil Research And Engineering Company Lubricating compositions containing polyalkylene glycol mono ethers
WO2013003394A1 (en) 2011-06-30 2013-01-03 Exxonmobil Research And Engineering Company Lubricating compositions containing polyetheramines
WO2013003392A1 (en) 2011-06-30 2013-01-03 Exxonmobil Research And Engineering Company Method of improving pour point of lubricating compositions containing polyalkylene glycol mono ethers
WO2013003406A1 (en) 2011-06-29 2013-01-03 Exxonmobil Research And Engineering Company Low viscosity engine oil with superior engine wear protection
EP2559748A1 (en) 2011-08-19 2013-02-20 Infineum International Limited Lubricating oil composition
EP2574656A1 (en) 2011-09-28 2013-04-03 Infineum International Limited Lubricating oil compositions
EP2584025A1 (en) 2011-10-21 2013-04-24 Infineum International Limited Lubricating oil composition
WO2013066915A1 (en) 2011-11-01 2013-05-10 Exxonmobil Research And Engineering Company Lubricants with improved low-temperature fuel economy
WO2013070376A2 (en) 2011-11-11 2013-05-16 Vanderbilt Chemicals, Llc Lubricant composition
WO2013074498A1 (en) 2011-11-14 2013-05-23 Exxonmobil Research And Engineering Company Method for improving engine fuel efficiency
WO2013082206A1 (en) 2011-12-02 2013-06-06 Exxonmobil Research And Engineering Company Method for improving engine wear and corrosion resistance
WO2013090051A1 (en) 2011-12-13 2013-06-20 Chemtura Corporation Cross products and co-oligomers of phenylenediamines and aromatic amines as antioxidants for lubricants
WO2013096532A1 (en) 2011-12-22 2013-06-27 Exxonmobil Research And Engineering Company Method for improving engine fuel efficiency
DE102012223638A1 (en) 2011-12-21 2013-06-27 Infineum International Ltd. A method for reducing the rate of decrease of the basicity of a lubricating oil composition which is used in a motor
WO2013101882A1 (en) 2011-12-29 2013-07-04 The Lubrizol Corporation Limited slip friction modifiers for differentials
EP2620207A2 (en) 2008-10-31 2013-07-31 Calera Corporation Non-cementitious compositions comprising CO2 sequestering additives
WO2013142110A1 (en) 2012-03-22 2013-09-26 Exxonmobil Research And Engineering Company Novel antioxidant combination and synthetic base oils containing the same
WO2013151911A1 (en) 2012-04-04 2013-10-10 The Lubrizol Corporation Bearing lubricants for pulverizing equipment
US8586520B2 (en) 2011-06-30 2013-11-19 Exxonmobil Research And Engineering Company Method of improving pour point of lubricating compositions containing polyalkylene glycol mono ethers
WO2013181318A1 (en) 2012-06-01 2013-12-05 Exxonmobil Research And Engineering Company Lubricant compostions and processes for preparing same
WO2014008121A1 (en) 2012-07-02 2014-01-09 Exxonmobil Research And Engineering Company Enhanced durability performance of lubricants using functionalized metal phosphate nanoplatelets
EP2687583A1 (en) 2012-07-17 2014-01-22 Infineum International Limited Lubricating oil compositions containing sterically hindered amines as ashless TBN sources
EP2692840A1 (en) 2012-07-31 2014-02-05 Infineum International Limited Lubricating oil composition
EP2692839A1 (en) 2012-07-31 2014-02-05 Infineum International Limited A lubricating oil compostion comprising a corrosion inhibitor
WO2014065984A1 (en) 2012-10-24 2014-05-01 Exxonmobil Reearch And Engineering Company High viscosity index lubricating oil base stock viscosity modifier combinations, and lubricating oils derived therefrom
WO2014066444A1 (en) 2012-10-24 2014-05-01 Exxonmobil Research And Engineering Comapny Functionalized polymers and oligomers as corrosion inhibitors and antiwear additives
EP2740782A1 (en) 2012-12-10 2014-06-11 Infineum International Limited Lubricating oil compositions containing sterically hindered amines as ashless tbn sources
WO2014105312A1 (en) 2012-12-28 2014-07-03 Chevron Oronite Company Llc Ultra-low saps lubricants for internal combustion engines
WO2014107314A1 (en) 2013-01-03 2014-07-10 Exxonmobil Research And Engineering Company Lubricating compositions having improved shear stability
WO2014107315A1 (en) 2013-01-04 2014-07-10 Exxonmobil Research And Engineering Company Method for improving engine fuel efficiency
WO2014137580A1 (en) 2013-03-07 2014-09-12 The Lubrizol Corporation Limited slip friction modifiers for differentials
WO2014149406A1 (en) 2013-03-15 2014-09-25 Exxonmobil Research And Engineering Company Method for improving thermal -oxidative stability and elastomer compatibility
WO2014158602A1 (en) 2013-03-14 2014-10-02 Exxonmobil Research And Engineering Company Method for improving emulsion characteristics of engine oils
WO2014158533A1 (en) 2013-03-14 2014-10-02 Exxonmobil Research And Engineering Company Lubricating composition providing high wear resistance
WO2014184062A1 (en) 2013-05-17 2014-11-20 Basf Se The use of polytetrahydrofuranes in lubricating oil compositions
WO2014184068A1 (en) 2013-05-14 2014-11-20 Basf Se Lubricating oil composition with enhanced energy efficiency
EP2837675A1 (en) 2013-08-15 2015-02-18 Infineum International Limited Automotive transmission fluid compositions for improved energy efficiency
EP2843033A1 (en) 2013-08-15 2015-03-04 Infineum International Limited Transmission fluid compositions for improved energy efficiency
WO2015050690A1 (en) 2013-10-03 2015-04-09 Exxonmobil Research And Engineering Company Compositions with improved varnish control properties
WO2015078707A1 (en) 2013-11-26 2015-06-04 Basf Se The use of polyalkylene glycol esters in lubricating oil compositions
WO2015095336A1 (en) 2013-12-18 2015-06-25 Chevron Phillips Chemical Company Lp Method for making polyolefins using aluminum halide catalyzed oligomerization of olefins
WO2015099907A1 (en) 2013-12-23 2015-07-02 Exxonmobil Research And Engineering Company Low viscosity ester lubricant and method for using
WO2015099821A1 (en) 2013-12-23 2015-07-02 Exxonmobil Research And Engineering Company Method for improving engine fuel efficiency
WO2015099820A1 (en) 2013-12-23 2015-07-02 Exxonmobil Research And Engineering Company Method for improving engine fuel efficiency
WO2015099819A1 (en) 2013-12-23 2015-07-02 Exxonmobil Research And Engineering Company Method for improving engine fuel efficiency
EP2913384A1 (en) 2014-02-26 2015-09-02 Infineum International Limited A lubricating oil composition
US9133581B2 (en) 2008-10-31 2015-09-15 Calera Corporation Non-cementitious compositions comprising vaterite and methods thereof
EP2937408A1 (en) 2014-04-22 2015-10-28 Basf Se Lubricant composition comprising an ester of a C17 alcohol mixture
EP2940110A1 (en) 2014-04-29 2015-11-04 Infineum International Limited Lubricating oil compositions
WO2015171981A1 (en) 2014-05-09 2015-11-12 Exxonmobil Research And Engineering Company Method for preventing or reducing low speed pre-ignition
WO2015171980A1 (en) 2014-05-09 2015-11-12 Exxonmobil Research And Engineering Company Method for preventing or reducing low speed pre-ignition
WO2015171978A1 (en) 2014-05-09 2015-11-12 Exxonmobil Research And Engineering Company Method for preventing or reducing low speed pre-ignition
WO2015171292A1 (en) 2014-05-08 2015-11-12 Exxonmobil Research And Engineering Company Method for preventing or reducing engine knock and pre-ignition
WO2015183455A1 (en) 2014-05-29 2015-12-03 Exxonmobil Research And Engineering Company Lubricating oil compositions with engine wear protection
WO2016043944A1 (en) 2014-09-17 2016-03-24 Exxonmobil Research And Engineering Company Composition and method for preventing or reducing engine knock and pre-ignition in high compression spark ignition engines
US9315756B2 (en) 2012-04-06 2016-04-19 Exxonmobil Research And Engineering Company Bio-feeds based hybrid group V base stocks and method of production thereof
WO2016073149A1 (en) 2014-11-03 2016-05-12 Exxonmobil Research And Engineering Company Low transition temperature mixtures or deep eutectic solvents and processes for preparation thereof
DE102015118989A1 (en) 2014-11-05 2016-05-12 Infineum International Ltd. Power transmission fluids having improved materials compatibility
EP3034587A1 (en) 2014-12-19 2016-06-22 Infineum International Limited Marine engine lubrication
WO2016106214A1 (en) 2014-12-24 2016-06-30 Exxonmobil Research And Engineering Company Methods for determining condition and quality of petroleum products
WO2016106211A1 (en) 2014-12-24 2016-06-30 Exxonmobil Research And Engineering Company Methods for authentication and identification of petroleum products
WO2016109382A1 (en) 2014-12-30 2016-07-07 Exxonmobil Research And Engineering Company Lubricating oil compositions with engine wear protection
WO2016109325A1 (en) 2014-12-30 2016-07-07 Exxonmobil Research And Engineering Company Lubricating oil compositions containing encapsulated microscale particles
WO2016109376A1 (en) 2014-12-30 2016-07-07 Exxonmobil Research And Engineering Company Lubricating oil compositions with engine wear protection
US9422497B2 (en) 2012-09-21 2016-08-23 Exxonmobil Research And Engineering Company Synthetic lubricant basestocks and methods of preparation thereof
WO2016138939A1 (en) 2015-03-03 2016-09-09 Basf Se Pib as high viscosity lubricant base stock
EP3085757A1 (en) 2015-04-23 2016-10-26 Basf Se Stabilization of alkoxylated polytetrahydrofuranes with antioxidants
US9506008B2 (en) 2013-12-23 2016-11-29 Exxonmobil Research And Engineering Company Method for improving engine fuel efficiency
WO2016191409A1 (en) 2015-05-28 2016-12-01 Exxonmobil Research And Engineering Company Composition and method for preventing or reducing engine knock and pre-ignition in high compression spark ignition engines
WO2016200606A1 (en) 2015-06-09 2016-12-15 Exxonmobil Research And Engineering Company Inverse micellar compositions containing lubricant additives
US9523057B2 (en) 2011-02-22 2016-12-20 Afton Chemical Corporation Fuel additives to maintain optimum injector performance
WO2017007670A1 (en) 2015-07-07 2017-01-12 Exxonmobil Research And Engineering Company Composition and method for preventing or reducing engine knock and pre-ignition in high compression spark ignition engines
EP3118285A1 (en) 2015-07-16 2017-01-18 Infineum International Limited Method of improving vehicle transmission operation through use of specific lubricant compositions
EP3124581A1 (en) 2015-07-30 2017-02-01 Infineum International Limited Dispersant additives and additive concentrates and lubricating oil compositions containing same
EP3135750A1 (en) 2015-08-26 2017-03-01 Infineum International Limited Lubricating oil compositions
EP3144372A1 (en) 2015-09-16 2017-03-22 Infineum International Limited Additive concentrates for the formulation of lubricating oil compositions
EP3153568A1 (en) 2015-10-05 2017-04-12 Infineum International Limited Additive concentrates for the formulation of lubricating oil compositions
WO2017117178A1 (en) 2015-12-28 2017-07-06 Exxonmobil Research And Engineering Company Bright stock production from deasphalted oil
EP3192858A1 (en) 2016-01-15 2017-07-19 Infineum International Limited Use of lubricating oil composition
US9732300B2 (en) 2015-07-23 2017-08-15 Chevron Phillipa Chemical Company LP Liquid propylene oligomers and methods of making same
WO2017146896A1 (en) 2016-02-26 2017-08-31 Exxonmobil Research And Engineering Company Lubricant compositions containing controlled release additives
WO2017146897A1 (en) 2016-02-26 2017-08-31 Exxonmobil Research And Engineering Company Lubricant compositions containing controlled release additives
EP3222698A1 (en) 2016-03-22 2017-09-27 Infineum International Limited Additive concentrates
US9775350B2 (en) 2004-10-14 2017-10-03 Koppers Performance Chemicals Inc. Micronized wood preservative formulations in organic carriers
WO2017172254A1 (en) 2016-03-31 2017-10-05 Exxonmobil Research And Engineering Company Lubricant compositions
US20170335226A1 (en) * 2016-05-23 2017-11-23 Infineum International Limited Highly Borated Dispersant Concentrates for Lubricating Oil Compositions and Methods for Forming Same
EP3252130A1 (en) 2016-06-03 2017-12-06 Infineum International Limited Additive package and lubricating oil composition
EP3257921A1 (en) 2016-06-14 2017-12-20 Infineum International Limited Lubricating oil additives
EP3263676A2 (en) 2016-06-30 2018-01-03 Infineum International Limited Lubricating oil compositions
WO2018013249A1 (en) 2016-07-12 2018-01-18 Chevron Phillips Chemical Company Lp Decene oligomers
US9885004B2 (en) 2013-12-23 2018-02-06 Exxonmobil Research And Engineering Company Method for improving engine fuel efficiency
WO2018026982A1 (en) 2016-08-03 2018-02-08 Exxonmobil Research And Engineering Company Lubricating engine oil for improved wear protection and fuel efficiency
WO2018027227A1 (en) 2016-08-05 2018-02-08 Rutgers, The State University Of New Jersey Thermocleavable friction modifiers and methods thereof
WO2018039571A1 (en) 2016-08-25 2018-03-01 Evonik Degussa Gmbh Amine alkenyl substituted succinimide reaction product fuel additives, compositions, and methods
US9914893B2 (en) 2014-01-28 2018-03-13 Basf Se Use of alkoxylated polyethylene glycols in lubricating oil compositions
EP3293246A1 (en) 2016-09-13 2018-03-14 Basf Se Lubricant compositions containing diurea compounds
WO2018048781A1 (en) 2016-09-12 2018-03-15 The Lubrizol Corporation Total base number boosters for marine diesel engine lubricating compositions
WO2018053098A1 (en) 2016-09-14 2018-03-22 The Lubrizol Corporation Lubricating composition comprising sulfonate detergent and ashless hydrocarbyl phenolic compound
US9926509B2 (en) 2015-01-19 2018-03-27 Exxonmobil Research And Engineering Company Lubricating oil compositions with engine wear protection and solubility
WO2018057377A1 (en) 2016-09-20 2018-03-29 Exxonmobil Research And Engineering Company Non-newtonian engine oil with superior engine wear protection and fuel economy
WO2018067903A1 (en) 2016-10-07 2018-04-12 Exxonmobil Research And Engineering Company Method for controlling electrical conductivity of lubricating oils in electric vehicle powertrains
WO2018067908A1 (en) 2016-10-07 2018-04-12 Exxonmobil Research And Engineering Company Low conductivity lubricating oils for electric and hybrid vehicles
WO2018067905A1 (en) 2016-10-07 2018-04-12 Exxonmobil Research And Engineering Company Method for preventing or minimizing electrostatic discharge and dielectric breakdown in electric vehicle powertrains
EP3315591A1 (en) 2016-10-28 2018-05-02 Basf Se Energy efficient lubricant compositions
EP3321347A1 (en) 2016-11-14 2018-05-16 Infineum International Limited Lubricating oil additives based on overbased gemini surfactant
US10000720B2 (en) 2014-05-22 2018-06-19 Basf Se Lubricant compositions containing beta-glucans
WO2018175830A1 (en) 2017-03-24 2018-09-27 Exxonmobil Research And Engineering Company Method for improving engine fuel efficiency and energy efficiency

Families Citing this family (108)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3231587A (en) * 1960-06-07 1966-01-25 Lubrizol Corp Process for the preparation of substituted succinic acid compounds
US3188307A (en) * 1962-04-13 1965-06-08 Pure Oil Co Alkenyl-n-sulfo-oxy-hydrocarbon-imides
US3194812A (en) * 1962-08-31 1965-07-13 Lubrizol Corp High molecular weight alkenyl-n-para amino-phenyl succinimide
US3194813A (en) * 1962-10-18 1965-07-13 Lubrizol Corp High molecular weight alkenyl-n-omega amino hexylsuccinimide
US3194814A (en) * 1962-10-18 1965-07-13 Lubrizol Corp High molecular weight alkenyl-n-allyl succinimide
US3458530A (en) * 1962-11-21 1969-07-29 Exxon Research Engineering Co Multi-purpose polyalkenyl succinic acid derivative
US3243371A (en) * 1962-12-10 1966-03-29 Shell Oil Co Lubricating composition
NL302077A (en) * 1962-12-19
US3282955A (en) * 1963-04-29 1966-11-01 Lubrizol Corp Reaction products of acylated nitrogen intermediates and a boron compound
US3281428A (en) * 1963-04-29 1966-10-25 Lubrizol Corp Reaction product of certain acylated nitrogen containing intermediates and a boron compound
US3294684A (en) * 1963-07-11 1966-12-27 Standard Oil Co Lubricant compositions containing detergency additives
US3280034A (en) * 1963-07-22 1966-10-18 Monsanto Co Alkenylsuccinimido alkyl-substituted imidazolidines and related materials
US3322670A (en) * 1963-08-26 1967-05-30 Standard Oil Co Detergent-dispersant lubricant additive having anti-rust and anti-wear properties
US3455831A (en) * 1963-09-27 1969-07-15 Monsanto Co Imines containing a polyalkenylsuccinic anhydride substituent
GB1053340A (en) * 1963-10-14 1900-01-01
GB1053577A (en) * 1963-11-01
GB1054280A (en) * 1963-12-11
US3306908A (en) * 1963-12-26 1967-02-28 Lubrizol Corp Reaction products of high molecular weight hydrocarbon succinic compounds, amines and heavy metal compounds
NL130536C (en) * 1964-05-19
US3446808A (en) * 1964-05-25 1969-05-27 Universal Oil Prod Co Borates of n-hydroxyalkyl-nitrogen-heterocyclic saturated compounds
US3281357A (en) * 1964-12-02 1966-10-25 Lubrizol Corp Process for preparing nitrogen and aluminum containing compositions
US3449362A (en) * 1965-03-08 1969-06-10 Standard Oil Co Alkenyl hydrocarbon substituted succinimides of polyamino ureas and their boron-containing derivatives
US3385791A (en) * 1965-03-22 1968-05-28 Standard Oil Co Lubricant oil composition
US3340190A (en) * 1965-06-01 1967-09-05 Standard Oil Co Railway diesel oil
US3284410A (en) * 1965-06-22 1966-11-08 Lubrizol Corp Substituted succinic acid-boron-alkylene amine-cyanamido derived additive and lubricating oil containing same
US3284409A (en) * 1965-06-22 1966-11-08 Lubrizol Corp Substituted succinic acid-boron-alkylene amine phosphatide derived additive and lubricating oil containing same
US3338834A (en) * 1965-11-19 1967-08-29 Chevron Res Process for preparing nitrogen and boron-containing lubricating oil additives
US3718663A (en) * 1967-11-24 1973-02-27 Standard Oil Co Preparation of oil-soluble boron derivatives of an alkylene polyamine-urea or thiourea-succinic anhydride addition product
US3903151A (en) * 1971-07-14 1975-09-02 Chevron Res Reaction products of alkali metal meborate and hydrocarbon substituted succinimide
US3892671A (en) * 1972-08-25 1975-07-01 Exxon Research Engineering Co Lubricant containing dispersant-pour depressant polymer
JPS4990704A (en) * 1972-12-29 1974-08-29
US3950341A (en) * 1973-04-12 1976-04-13 Toa Nenryo Kogyo Kabushiki Kaisha Reaction product of a polyalkenyl succinic acid or its anhydride, a hindered alcohol and an amine
FR2271281B2 (en) * 1974-03-29 1977-01-21 Inst Francais Du Petrole
US4080303A (en) * 1974-07-22 1978-03-21 The Lubrizol Corporation Lubricant compositions containing boron dispersant, VI improver, and aromatic carboxylic acid esters
FR2307845B1 (en) * 1975-04-18 1978-07-28 Orogil
US4025445A (en) * 1975-12-15 1977-05-24 Texaco Inc. Boron amide lubricating oil additive
US4092127A (en) * 1976-12-20 1978-05-30 Exxon Research & Engineering Co. Anti-dieseling additive for spark ignition engines
US4184851A (en) * 1977-07-25 1980-01-22 Exxon Research & Engineering Co. Borated derivatives of hydrocarbon substituted succinamic acids and/or acid salts thereof are flow improvers for middle distillate fuel oils (PT-364)
CA1125735A (en) * 1978-09-18 1982-06-15 Esther D. Winans Molybdenum complexes of ashless nitrogen dispersants as friction reducing antiwear additives for lubricating oils
US4666620A (en) * 1978-09-27 1987-05-19 The Lubrizol Corporation Carboxylic solubilizer/surfactant combinations and aqueous compositions containing same
US4448703A (en) * 1981-02-25 1984-05-15 The Lubrizol Corporation Carboxylic solubilizer/surfactant combinations and aqueous compositions containing same
US4368133A (en) * 1979-04-02 1983-01-11 The Lubrizol Corporation Aqueous systems containing nitrogen-containing, phosphorous-free carboxylic solubilizer/surfactant additives
US4447348A (en) * 1981-02-25 1984-05-08 The Lubrizol Corporation Carboxylic solubilizer/surfactant combinations and aqueous compositions containing same
DE2948503A1 (en) * 1979-12-01 1981-06-11 Huels Chemische Werke Ag Use of alkali metal or amine salts of a mixture of 2- and 3-alkyladipinsaeuren as a corrosion inhibitor
CA1168649A (en) * 1981-03-23 1984-06-05 Robert E. Malec Lubricating compositions
FR2510598B1 (en) * 1981-07-30 1985-01-18 Inst Francais Du Petrole
EP0074199B1 (en) * 1981-09-01 1986-11-12 The Lubrizol Corporation Acylated ether amine and lubricants and fuels containing the same
US4581038A (en) * 1981-09-01 1986-04-08 The Lubrizol Corporation Acylated ether amine and lubricants and fuels containing the same
DE3368438D1 (en) * 1982-02-03 1987-01-29 Lubrizol Corp Compositions for use in alcohol and alcohol containing fuels
FR2528423B1 (en) * 1982-06-10 1987-07-24 Inst Francais Du Petrole Nitrogens additives useful as agents for lowering the cloud point of distillate hydrocarbon means and compositions of middle distillate hydrocarbon containing said additives
US4575526A (en) * 1982-08-09 1986-03-11 The Lubrizol Corporation Hydrocarbyl substituted carboxylic acylaging agent derivative containing combinations, and fuels containing same
US4613342A (en) * 1982-08-09 1986-09-23 The Lubrizol Corporation Hydrocarbyl substituted carboxylic acylating agent derivative containing combinations, and fuels containing same
US4564460A (en) * 1982-08-09 1986-01-14 The Lubrizol Corporation Hydrocarbyl-substituted carboxylic acylating agent derivative containing combinations, and fuels containing same
US4489194A (en) * 1982-08-09 1984-12-18 The Lubrizol Corporation Carboxylic acylating agents substituted with olefin polymers of high/low molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same
US4596663A (en) * 1982-08-09 1986-06-24 The Lubrizol Corporation Carboxylic acylating agents substituted with olefin polymers of high molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same
US4559155A (en) * 1982-08-09 1985-12-17 The Lubrizol Corporation Hydrocarbyl substituted carboxylic acylating agent derivative containing combinations, and fuels containing same
US4486573A (en) * 1982-08-09 1984-12-04 The Lubrizol Corporation Carboxylic acylating agents substituted with olefin polymers of high molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same
US4471091A (en) * 1982-08-09 1984-09-11 The Lubrizol Corporation Combinations of carboxylic acylating agents substituted with olefin polymers of high and low molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same
US4623684A (en) 1982-08-09 1986-11-18 The Lubrizol Corporation Hydrocarbyl substituted carboxylic acylating agent derivative containing combinations, and fuels containing same
US4756820A (en) * 1985-09-06 1988-07-12 Betz Laboratories, Inc. Method for retarding corrosion and coke formation and deposition during pyrolytic hydrocarbon processing
US4780111A (en) 1985-11-08 1988-10-25 The Lubrizol Corporation Fuel compositions
US4770803A (en) * 1986-07-03 1988-09-13 The Lubrizol Corporation Aqueous compositions containing carboxylic salts
USRE36479E (en) * 1986-07-03 2000-01-04 The Lubrizol Corporation Aqueous compositions containing nitrogen-containing salts
US4755311A (en) * 1986-08-14 1988-07-05 The Lubrizol Corporation Phosphorus-, sulfur- and boron-containing compositions, and lubricant and functional fluid compositions containing same
US4866139A (en) * 1986-10-07 1989-09-12 Exxon Chemical Patents Inc. Lactone modified, esterified dispersant additives useful in oleaginous compositions
US4906394A (en) * 1986-10-07 1990-03-06 Exxon Chemical Patents Inc. Lactone modified mono-or dicarboxylic acid based adduct dispersant compositions
US5032320A (en) * 1986-10-07 1991-07-16 Exxon Chemical Patents Inc. Lactone modified mono- or dicarboxylic acid based adduct dispersant compositions
US4963275A (en) * 1986-10-07 1990-10-16 Exxon Chemical Patents Inc. Dispersant additives derived from lactone modified amido-amine adducts
US4866140A (en) * 1986-10-07 1989-09-12 Exxon Chemical Patents Inc. Lactone modified adducts or reactants and oleaginous compositions containing same
US4954276A (en) * 1986-10-07 1990-09-04 Exxon Chemical Patents Inc. Lactone modified adducts or reactants and oleaginous compositions containing same
US4925983A (en) * 1986-11-12 1990-05-15 The Lubrizol Corporation Boronated compounds
US4938880A (en) * 1987-05-26 1990-07-03 Exxon Chemical Patents Inc. Process for preparing stable oleaginous compositions
US4971711A (en) * 1987-07-24 1990-11-20 Exxon Chemical Patents, Inc. Lactone-modified, mannich base dispersant additives useful in oleaginous compositions
US4820432A (en) * 1987-07-24 1989-04-11 Exxon Chemical Patents Inc. Lactone-modified, Mannich base dispersant additives useful in oleaginous compositions
US4943382A (en) * 1988-04-06 1990-07-24 Exxon Chemical Patents Inc. Lactone modified dispersant additives useful in oleaginous compositions
US5041622A (en) * 1988-04-22 1991-08-20 The Lubrizol Corporation Three-step process for making substituted carboxylic acids and derivatives thereof
GB8916943D0 (en) * 1988-09-21 1989-09-13 Ici Plc Water-in-oil emulsion explosive
US5646098A (en) * 1990-07-23 1997-07-08 Exxon Chemical Patents Inc Carbonyl containing compounds and their derivatives as multi-functional fuel and lube additives
US5562864A (en) * 1991-04-19 1996-10-08 The Lubrizol Corporation Lubricating compositions and concentrates
US5614480A (en) * 1991-04-19 1997-03-25 The Lubrizol Corporation Lubricating compositions and concentrates
US5490945A (en) * 1991-04-19 1996-02-13 The Lubrizol Corporation Lubricating compositions and concentrates
US5221491A (en) * 1991-08-09 1993-06-22 Exxon Chemical Patents Inc. Two-cycle oil additive
US5304315A (en) * 1992-04-15 1994-04-19 Exxon Chemical Patents Inc. Prevention of gel formation in two-cycle oils
US5430105A (en) * 1992-12-17 1995-07-04 Exxon Chemical Patents Inc. Low sediment process for forming borated dispersant
FR2699550B1 (en) * 1992-12-17 1995-01-27 Inst Francais Du Petrole Petroleum middle distillate composition containing nitrogenous additives used as agents limiting the sedimentation rate of the paraffins.
US5562867A (en) * 1993-12-30 1996-10-08 Exxon Chemical Patents Inc Biodegradable two-cycle oil composition
GB2312212B (en) * 1996-04-19 1999-09-29 Ethyl Petroleum Additives Ltd Dispersants
GB9802210D0 (en) * 1998-02-02 1998-04-01 Xaar Technology Ltd Ink jet printer ink
US6010986A (en) * 1998-07-31 2000-01-04 The Lubrizol Corporation Alcohol borate esters to improve bearing corrosion in engine oils
US6008165A (en) * 1998-07-31 1999-12-28 The Lubrizol Corporation Alcohol borate esters and borated dispersants to improve bearing corrosion in engine oils
US6231659B1 (en) 1999-06-24 2001-05-15 Albemarle Corporation Sizing agents and starting materials for their preparation
US6225437B1 (en) 1999-06-24 2001-05-01 Albemarle Corporation Sizing agents of enhanced performance capabilities
US7182795B2 (en) * 2002-03-13 2007-02-27 Atton Chemical Intangibles Llc Fuel lubricity additives derived from hydrocarbyl succinic anhydrides and hydroxy amines, and middle distillate fuels containing same
US20050041395A1 (en) * 2003-08-21 2005-02-24 The Lubrizol Corporation Multifunctional dispersants
EP1819739A2 (en) * 2004-12-09 2007-08-22 The Lubrizol Corporation Process of preparation of an additive and its use
US20110036262A1 (en) * 2005-07-11 2011-02-17 Advanced Lubrication Technology, Inc. Corrosion Prevention and Friction Reduction Coating and Low Temperature Process
US20070021310A1 (en) * 2005-07-11 2007-01-25 Olliges William E Corrosion Prevention and Friction Reduction Coating and Low Temperature Process
WO2010115594A9 (en) 2009-04-07 2011-08-04 Infineum International Limited Marine engine lubrication
KR20140125873A (en) 2012-02-17 2014-10-29 더루우브리졸코오포레이션 Lubricating composition including esterified copolymer and low dispersant levels suitable for driveline applications
WO2013123160A8 (en) 2012-02-17 2013-10-03 The Lubrizol Corporation Mixtures of olefin-ester copolymer with polyolefin as viscosity modifier
WO2014047017A1 (en) 2012-09-24 2014-03-27 The Lubrizol Corporation Lubricant comprising a mixture of an olefin-ester copolymer with an ethylene alpha-olefin copolymer
EP2727984A1 (en) 2012-11-02 2014-05-07 Infineum International Limited Marine engine lubrication
DK2735603T3 (en) 2012-11-21 2016-08-29 Infineum Int Ltd Lubrication to a marine engine
ES2608805T3 (en) 2013-02-07 2017-04-17 Infineum International Limited Marine engine lubrication
ES2646051T3 (en) 2013-09-24 2017-12-11 Infineum International Limited Marine engine lubrication
US20170022443A1 (en) 2014-03-05 2017-01-26 The Lubrizol Corporation Emulsifier components and methods of using the same
EP3029133B1 (en) 2014-12-04 2017-03-15 Infineum International Limited Marine engine lubrication
US9879202B2 (en) 2014-12-04 2018-01-30 Infineum International Limited Marine engine lubrication

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2459597A (en) * 1945-05-16 1949-01-18 Gulf Research Development Co Di-alkylated mono-hydroxy phenol
GB819169A (en) * 1955-01-27 1959-08-26 Lubrizol Corp Phosphorus-and-sulfur-containing materials and lubricants containing them
US2956018A (en) * 1955-07-01 1960-10-11 Continental Oil Co Metal containing organic compositions and method of preparing the same
GB874877A (en) * 1959-01-22 1961-08-10 Exxon Research Engineering Co Metal salts of organic dithiophosphates and lubricating compositions containing them
US3000916A (en) * 1958-06-03 1961-09-19 Standard Oil Co Composition of matter prepared by reacting polymerized linoleic acid with an amine and subsequently reacting the mixture with boric acid
US3018250A (en) * 1959-08-24 1962-01-23 California Research Corp Lubricating oil compositions containing nu-dialkylaminoalkyl alkenyl succinimides

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2052192A (en) * 1935-10-23 1936-08-25 Ici Ltd Boric acid esters
US2234581A (en) * 1937-09-30 1941-03-11 Standard Oil Dev Co Hydrocarbon composition containing organic boron compounds
US2216618A (en) * 1939-08-10 1940-10-01 Katz Jacob Surface active anionic boric acid ester compounds of amino alcohols
US2422278A (en) * 1943-12-01 1947-06-17 Standard Oil Dev Co Lubricating oil composition
US2611746A (en) * 1947-06-10 1952-09-23 Aluminum Co Of America Lubricating composition
FR1254094A (en) * 1960-03-29 1961-02-17 Lubrizol Corp lubricants for metals-free additives

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2459597A (en) * 1945-05-16 1949-01-18 Gulf Research Development Co Di-alkylated mono-hydroxy phenol
GB819169A (en) * 1955-01-27 1959-08-26 Lubrizol Corp Phosphorus-and-sulfur-containing materials and lubricants containing them
US2956018A (en) * 1955-07-01 1960-10-11 Continental Oil Co Metal containing organic compositions and method of preparing the same
US3000916A (en) * 1958-06-03 1961-09-19 Standard Oil Co Composition of matter prepared by reacting polymerized linoleic acid with an amine and subsequently reacting the mixture with boric acid
GB874877A (en) * 1959-01-22 1961-08-10 Exxon Research Engineering Co Metal salts of organic dithiophosphates and lubricating compositions containing them
US3018250A (en) * 1959-08-24 1962-01-23 California Research Corp Lubricating oil compositions containing nu-dialkylaminoalkyl alkenyl succinimides
US3018291A (en) * 1959-08-24 1962-01-23 California Research Corp Nu-dialkylaminoalkyl alkenyl succinimides

Cited By (447)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3338832A (en) * 1963-04-29 1967-08-29 Lubrizol Corp Lubricating oil containing reaction product of certain acylated nitrogen containing intermediates and a boron compound
US3533945A (en) * 1963-11-13 1970-10-13 Lubrizol Corp Lubricating oil composition
US3344069A (en) * 1965-07-01 1967-09-26 Lubrizol Corp Lubricant additive and lubricant containing same
US3442808A (en) * 1966-11-01 1969-05-06 Standard Oil Co Lubricating oil additives
US3929650A (en) * 1974-03-22 1975-12-30 Chevron Res Extreme pressure agent and its preparation
US5162526A (en) * 1976-09-24 1992-11-10 Exxon Chemical Patents Inc. Macrocyclic polyamine and polycyclic polyamine multifunctional lubricating oil
US4116876A (en) * 1977-01-28 1978-09-26 Exxon Research & Engineering Co. Borated oxazolines as varnish inhibiting dispersants in lubricating oils
FR2404668A1 (en) * 1977-10-03 1979-04-27 Exxon Research Engineering Co A lubricating oil composition mixed with a polyol ester and imide
US4173540A (en) * 1977-10-03 1979-11-06 Exxon Research & Engineering Co. Lubricating oil composition containing a dispersing-varnish inhibiting combination of polyol ester compound and a borated acyl nitrogen compound
US4331545A (en) * 1979-04-19 1982-05-25 Edwin Cooper, Inc. Lubricating compositions containing boronated N-alkanol hydrocarbylamide
US4328113A (en) * 1980-01-14 1982-05-04 Mobil Oil Corporation Friction reducing additives and compositions thereof
EP0039998A1 (en) 1980-05-08 1981-11-18 Exxon Research And Engineering Company Lubricating oil composition containing sediment-reducing additive
US4505829A (en) * 1980-05-08 1985-03-19 Exxon Research & Engineering Co. Lubricating oil composition containing sediment-reducing additive
US4295983A (en) * 1980-06-12 1981-10-20 Ethyl Corporation Lubricating oil composition containing boronated N-hydroxymethyl succinimide friction reducers
US4338205A (en) * 1980-08-25 1982-07-06 Exxon Research & Engineering Co. Lubricating oil with improved diesel dispersancy
DE3132220A1 (en) * 1980-08-25 1982-05-13 Exxon Research Engineering Co Kind of oil with improved dispersibility in diesel engines
US4374033A (en) * 1981-06-18 1983-02-15 Edwin Cooper, Inc. Dispersant and lubricating oil containing the dispersant
US4873009A (en) * 1982-03-29 1989-10-10 Amoco Corporation Borated lube oil additive
EP0090629A3 (en) * 1982-03-29 1984-09-05 Standard Oil Company Borated lube oil additive
EP0090629A2 (en) * 1982-03-29 1983-10-05 Amoco Corporation Borated lube oil additive
US4529526A (en) * 1982-11-30 1985-07-16 Honda Motor Co., Ltd. Lubricating oil composition
EP0113582A2 (en) * 1982-12-27 1984-07-18 Exxon Research And Engineering Company Macrocyclic polyamine and polycyclic polyamine multifunctional lubricating oil additives
US4637886A (en) * 1982-12-27 1987-01-20 Exxon Research & Engineering Co. Macrocyclic polyamine and polycyclic polyamine multifunctional lubricating oil additives
EP0113582A3 (en) * 1982-12-27 1986-04-23 Exxon Research And Engineering Company Macrocyclic polyamine and polycyclic polyamine multifunctional lubricating oil additives
FR2541685A1 (en) * 1983-02-24 1984-08-31 Chevron Res A lubricating oil composition containing a succinimide of fatty acid ester of glycerol borate complex
US4455243A (en) * 1983-02-24 1984-06-19 Chevron Research Company Succinimide complexes of borated fatty acid esters of glycerol and lubricating oil compositions containing same
EP0132383A3 (en) * 1983-07-25 1986-09-24 Amoco Corporation Boration of polyamine dispersants with polyborate esters
EP0132383A2 (en) * 1983-07-25 1985-01-30 Amoco Corporation Boration of polyamine dispersants with polyborate esters
US4801390A (en) * 1984-06-05 1989-01-31 Exxon Research & Engineering Co. Lubricating compositions
WO1986004601A1 (en) 1985-01-31 1986-08-14 The Lubrizol Corporation Sulfur-containing compositions, and additive concentrates and lubricating oils containing same
US4749505A (en) * 1985-07-08 1988-06-07 Exxon Chemical Patents Inc. Olefin polymer viscosity index improver additive useful in oil compositions
US6127321A (en) * 1985-07-11 2000-10-03 Exxon Chemical Patents Inc Oil soluble dispersant additives useful in oleaginous compositions
US6355074B1 (en) 1985-07-11 2002-03-12 Exxon Chemical Patents Inc Oil soluble dispersant additives useful in oleaginous compositions
EP0208560A3 (en) * 1985-07-11 1987-10-07 Exxon Chemical Patents Inc. Oil-soluble dispersant additives for fuels and lubricating oils
US5118432A (en) * 1985-07-11 1992-06-02 Exxon Chemical Patents Inc. Dispersant additive mixtures for oleaginous compositions
EP0208560A2 (en) * 1985-07-11 1987-01-14 Exxon Chemical Patents Inc. Oil-soluble dispersant additives in fuels and lubricating oils
US6051537A (en) * 1985-07-11 2000-04-18 Exxon Chemical Patents Inc Dispersant additive mixtures for oleaginous compositions
US4992150A (en) * 1985-10-09 1991-02-12 Nippon Oil Co, Ltd. Process for preparing oil-soluble nitrogen-containing compounds
GB2183243B (en) * 1985-10-09 1990-01-24 Nippon Oil Co Ltd Process for preparing oil-soluble nitrogen-containing compounds
US4842755A (en) * 1986-02-04 1989-06-27 Exxon Chemical Patents Inc. Marine lubricating composition
JP2656522B2 (en) * 1986-06-13 1997-09-24 ザ ルブリゾル コーポレーション Lubricants phosphorus-containing and functional fluid compositions
JPH01502987A (en) * 1986-06-13 1989-10-12
US4954277A (en) * 1986-10-07 1990-09-04 Exxon Chemical Patents Inc. Lactone modified, esterified or aminated additives useful in oleaginous compositions and compositions containing same
US4866141A (en) * 1986-10-07 1989-09-12 Exxon Chemical Patents Inc. Lactone modified, esterfied or aminated additives useful in oleaginous compositions and compositions containing same
US5788722A (en) * 1986-10-16 1998-08-04 Exxon Chemical Patents Inc High functionality low molecular weight oil soluble dispersant additives useful in oleaginous compositions
US5756428A (en) * 1986-10-16 1998-05-26 Exxon Chemical Patents Inc. High functionality low molecular weight oil soluble dispersant additives useful in oleaginous composition
US5110488A (en) * 1986-11-24 1992-05-05 The Lubrizol Corporation Lubricating compositions containing reduced levels of phosphorus
US4873004A (en) * 1986-11-28 1989-10-10 Shell Oil Company Lubricating composition
US4863624A (en) * 1987-09-09 1989-09-05 Exxon Chemical Patents Inc. Dispersant additives mixtures for oleaginous compositions
US4948522A (en) * 1988-02-23 1990-08-14 Exxon Chemical Patents Inc. Dispersant for marine diesel cylinder lubricant
US5164103A (en) * 1988-03-14 1992-11-17 Ethyl Petroleum Additives, Inc. Preconditioned atf fluids and their preparation
US5389273A (en) * 1988-03-14 1995-02-14 Ethyl Petroleum Additives, Inc. Modified succinimide or succinamide dispersants and their production
US5439606A (en) * 1988-03-14 1995-08-08 Ethyl Petroleum Additives, Inc. Modified succinimide or succinamide dispersants and their production
US5198133A (en) * 1988-03-14 1993-03-30 Ethyl Petroleum Additives, Inc. Modified succinimide or sucinamide dispersants and their production
US4855074A (en) * 1988-03-14 1989-08-08 Ethyl Petroleum Additives, Inc. Homogeneous additive concentrates and their formation
US5326487A (en) * 1988-06-24 1994-07-05 Exxon Chemical Patents Inc. Mixed phosphorous- and sulfur- containing reaction products useful in power transmitting compositions
US5534170A (en) * 1988-06-24 1996-07-09 Exxon Chemical Patents Inc. Mixed phosphorus- and sulfur-containing reaction products useful in power transmitting compositions
US5185090A (en) * 1988-06-24 1993-02-09 Exxon Chemical Patents Inc. Low pressure derived mixed phosphorous- and sulfur-containing reaction products useful in power transmitting compositions and process for preparing same
US5242612A (en) * 1988-06-24 1993-09-07 Exxon Chemical Patents Inc. Mixed phosphorous- and sulfur-containing reaction products useful in power transmitting compositions
EP0351964A1 (en) 1988-06-24 1990-01-24 Exxon Chemical Patents Inc. Synergistic combination of additives useful in power transmitting compositions
US5314633A (en) * 1988-06-24 1994-05-24 Exxon Chemical Patents Inc. Low pressure derived mixed phosphorous- and sulfur- containing reaction products useful in power transmitting compositions and process for preparing same
US5078893A (en) * 1988-06-24 1992-01-07 Exxon Chemical Patents Inc. Synergistic combination of additives useful in power transmitting compositions
US5320768A (en) * 1988-06-24 1994-06-14 Exxon Chemical Patents Inc. Hydroxy ether amine friction modifier for use in power transmission fluids and anti-wear additives for use in combination therewith
US5334329A (en) * 1988-10-07 1994-08-02 The Lubrizol Corporation Lubricant and functional fluid compositions exhibiting improved demulsibility
EP0399764A1 (en) 1989-05-22 1990-11-28 Ethyl Petroleum Additives Limited Lubricant compositions
US4981492A (en) * 1989-12-13 1991-01-01 Mobil Oil Corporation Borated triazole-substituted polyalkenyl succinimides as multifunctional lubricant and fuel additives
US5225093A (en) * 1990-02-16 1993-07-06 Ethyl Petroleum Additives, Inc. Gear oil additive compositions and gear oils containing the same
US5176840A (en) * 1990-02-16 1993-01-05 Ethyl Petroleum Additives, Inc. Gear oil additive composition and gear oil containing the same
US5942470A (en) * 1990-05-17 1999-08-24 Ethyl Petroleum Additives, Inc. Lubricant compositions
US5024677A (en) * 1990-06-11 1991-06-18 Nalco Chemical Company Corrosion inhibitor for alcohol and gasohol fuels
EP0611818A1 (en) 1990-07-31 1994-08-24 Exxon Chemical Patents Inc. Low pressure derived mixed phosphorous- and sulfur-containing reaction products useful in power transmitting compositions and process for preparing the same
US5232616A (en) * 1990-08-21 1993-08-03 Chevron Research And Technology Company Lubricating compositions
US5562742A (en) * 1991-05-13 1996-10-08 The Lubrizol Corporation Copper-containing organometallic complexes and concentrates and diesel fuels containing same
US5340369A (en) * 1991-05-13 1994-08-23 The Lubrizol Corporation Diesel fuels containing organometallic complexes
US5376154A (en) * 1991-05-13 1994-12-27 The Lubrizol Corporation Low-sulfur diesel fuels containing organometallic complexes
US5360459A (en) * 1991-05-13 1994-11-01 The Lubrizol Corporation Copper-containing organometallic complexes and concentrates and diesel fuels containing same
US5518510A (en) * 1991-05-13 1996-05-21 The Lubrizol Corporation Low-sulfur diesel fuels containing organo-metallic complexes
US5344467A (en) * 1991-05-13 1994-09-06 The Lubrizol Corporation Organometallic complex-antioxidant combinations, and concentrates and diesel fuels containing same
US5534039A (en) * 1991-05-13 1996-07-09 The Lubrizol Corporation Organometallic complex-antioxidant combinations, and concentrates and diesel fuels containing same
US5652201A (en) * 1991-05-29 1997-07-29 Ethyl Petroleum Additives Inc. Lubricating oil compositions and concentrates and the use thereof
US5328619A (en) * 1991-06-21 1994-07-12 Ethyl Petroleum Additives, Inc. Oil additive concentrates and lubricants of enhanced performance capabilities
US5227082A (en) * 1991-12-23 1993-07-13 Exxon Research And Engineering Company Lubricating oil having improved rust inhibition and demulsibility
EP0558835A1 (en) 1992-01-30 1993-09-08 Albemarle Corporation Biodegradable lubricants and functional fluids
US5211834A (en) * 1992-01-31 1993-05-18 Betz Laboratories, Inc. Method for controlling fouling deposit formation in a liquid hydrocarbonaceous medium using boronated derivatives of polyalkenylsuccinimides
US5330667A (en) * 1992-04-15 1994-07-19 Exxon Chemical Patents Inc. Two-cycle oil additive
US5554310A (en) * 1992-12-17 1996-09-10 Exxon Chemical Patents Inc. Trisubstituted unsaturated polymers
US5717039A (en) * 1992-12-17 1998-02-10 Exxon Chemical Patents Inc. Functionalization of polymers based on Koch chemistry and derivatives thereof
US5643859A (en) * 1992-12-17 1997-07-01 Exxon Chemical Patents Inc. Derivatives of polyamines with one primary amine and secondary of tertiary amines
US5646332A (en) * 1992-12-17 1997-07-08 Exxon Chemical Patents Inc. Batch Koch carbonylation process
US5650536A (en) * 1992-12-17 1997-07-22 Exxon Chemical Patents Inc. Continuous process for production of functionalized olefins
US5698722A (en) * 1992-12-17 1997-12-16 Exxon Chemical Patents Inc. Functionalization of polymers based on Koch chemistry and derivatives thereof
US5696064A (en) * 1992-12-17 1997-12-09 Exxon Chemical Patents Inc. Functionalization of polymers based on Koch chemistry and derivatives thereof
US5703256A (en) * 1992-12-17 1997-12-30 Exxon Chemical Patents Inc. Functionalization of polymers based on Koch chemistry and derivatives thereof
US5629434A (en) * 1992-12-17 1997-05-13 Exxon Chemical Patents Inc Functionalization of polymers based on Koch chemistry and derivatives thereof
US5767044A (en) * 1993-08-20 1998-06-16 The Lubrizol Corporation Lubricating compositions with improved thermal stability and limited slip performance
EP0683220A2 (en) 1994-05-18 1995-11-22 Ethyl Corporation Lubricant additive compositions
WO1996037582A1 (en) * 1994-05-20 1996-11-28 Exxon Research And Engineering Company Lubricating oil composition
US6362136B1 (en) 1994-05-23 2002-03-26 The Lubrizol Corporation Compositions for extending seal life, and lubricants and functional fluids containing the same
WO1995034615A1 (en) * 1994-06-16 1995-12-21 Exxon Chemical Limited Multigrade lubricating compositions containing no viscosity modifier
US5767046A (en) * 1994-06-17 1998-06-16 Exxon Chemical Company Functionalized additives useful in two-cycle engines
EP0695798A2 (en) 1994-08-03 1996-02-07 The Lubrizol Corporation Lubricating compositions, concentrates, and greases containing the combination of an organic polysulfide and an overbased composition or a phosphorus or boron compound
US6489271B1 (en) 1994-08-03 2002-12-03 The Lubrizol Corporation Combination of a sulfur compound and specific phosphorus compounds and their use in lubricating compositions, concentrates and greases
EP0713907A2 (en) 1994-09-26 1996-05-29 Ethyl Petroleum Additives Limited Zinc additives of enhanced performance capabilities
US6306802B1 (en) 1994-09-30 2001-10-23 Exxon Chemical Patents Inc. Mixed antioxidant composition
EP0713908A1 (en) 1994-11-22 1996-05-29 Ethyl Corporation Power transmission fluids
US6121209A (en) * 1994-12-09 2000-09-19 Exxon Chemical Patents Inc Synergistic antioxidant systems
US5658862A (en) * 1994-12-20 1997-08-19 Exxon Research And Engineering Company Engine oil with improved fuel economy properties (law372).
US6855675B1 (en) * 1995-05-24 2005-02-15 Tonengeneral Sekiyu K.K. Lubricating oil composition
US5652202A (en) * 1995-08-15 1997-07-29 Exxon Chemical Patents Inc. Lubricating oil compositions
US5558802A (en) * 1995-09-14 1996-09-24 Exxon Chemical Patents Inc Multigrade crankcase lubricants with low temperature pumpability and low volatility
BE1010192A3 (en) * 1995-12-01 1998-02-03 Ethyl Petroleum Additives Ltd Dispersants diesel compatible with seals.
FR2741890A1 (en) * 1995-12-01 1997-06-06 Ethyl Petroleum Additives Ltd Dispersants for diesel engines compatible with seals
US6613722B1 (en) * 1997-03-07 2003-09-02 Exxon Chemical Patents Inc. Lubricating composition
US6624123B2 (en) * 1997-04-11 2003-09-23 Chevron Chemical S.A. Use of surfactants with high molecular weight for improving the filterability in hydraulic lubricants
WO1998047989A1 (en) 1997-04-21 1998-10-29 Exxon Chemical Patents Inc. Power transmission fluids containing alkyl phosphonates
US6042626A (en) * 1997-08-01 2000-03-28 Ethyl Corporation Phosphorylated and/or boronated dispersants as thermal stability additives for distillate fuels
US6028210A (en) * 1997-12-18 2000-02-22 Exxon Chemical Patents, Inc. Process for making sulfur boron antiwear agents for lubricating compositions
WO1999036491A1 (en) 1998-01-13 1999-07-22 Exxon Chemical Patents Inc. Automatic transmission fluids of improved viscometric properties
US6001780A (en) * 1998-06-30 1999-12-14 Chevron Chemical Company Llc Ashless lubricating oil formulation for natural gas engines
US6361573B1 (en) * 1999-08-31 2002-03-26 Ethyl Corporation Fuel dispersants with enhanced lubricity
US6423670B2 (en) 2000-03-20 2002-07-23 Infineum International Ltd. Lubricating oil compositions
US20030220206A1 (en) * 2000-09-29 2003-11-27 Nippon Mitsubishi Oil Corporation Lubricant compositions
US6828286B2 (en) 2000-09-29 2004-12-07 Nippon Mitsubishi Oil Corporation Lubricant compositions
US20030173251A1 (en) * 2000-12-22 2003-09-18 Antonio Gutierrez Hydroxy aromatic mannich base condensation products and the use thereof as soot dispersants in lubricating oil compositions
US6855674B2 (en) 2000-12-22 2005-02-15 Infineum International Ltd. Hydroxy aromatic Mannich base condensation products and the use thereof as soot dispersants in lubricating oil compositions
US6677281B2 (en) 2001-04-20 2004-01-13 Exxonmobil Research And Engineering Company Synergistic combination of metallic and ashless rust inhibitors to yield improved rust protection and demulsibility in dispersant-containing lubricants
US6824671B2 (en) 2001-05-17 2004-11-30 Exxonmobil Chemical Patents Inc. Low noack volatility poly α-olefins
US20050045527A1 (en) * 2001-05-17 2005-03-03 Goze Maria Caridad B. Low noack volatility poly alpha-olefins
US20020193650A1 (en) * 2001-05-17 2002-12-19 Goze Maria Caridad B. Low noack volatility poly alpha-olefins
US6949688B2 (en) 2001-05-17 2005-09-27 Exxonmobil Chemical Patents Inc. Low Noack volatility poly α-olefins
EP2272940A1 (en) 2001-09-14 2011-01-12 Afton Chemical Intangibles LLC Fuels compositions for direct injection gasoline engines
US6743757B2 (en) 2001-12-06 2004-06-01 Infineum International Ltd. Dispersants and lubricating oil compositions containing same
US6734148B2 (en) 2001-12-06 2004-05-11 Infineum International Ltd. Dispersants and lubricating oil compositions containing same
US6627584B2 (en) 2002-01-28 2003-09-30 Ethyl Corporation Automatic transmission fluid additive comprising reaction product of hydrocarbyl acrylates and dihydrocarbyldithiophosphoric acids
US6573223B1 (en) 2002-03-04 2003-06-03 The Lubrizol Corporation Lubricating compositions with good thermal stability and demulsibility properties
US6689723B2 (en) 2002-03-05 2004-02-10 Exxonmobil Chemical Patents Inc. Sulfide- and polysulfide-containing lubricating oil additive compositions and lubricating compositions containing the same
WO2003095595A1 (en) 2002-05-09 2003-11-20 The Lubrizol Corporation Continuously variable transmission fluids comprising a combination of calcium- and magnesium-overbased detergents
US6869917B2 (en) 2002-08-16 2005-03-22 Exxonmobil Chemical Patents Inc. Functional fluid lubricant using low Noack volatility base stock fluids
US20040033908A1 (en) * 2002-08-16 2004-02-19 Deckman Douglas E. Functional fluid lubricant using low Noack volatility base stock fluids
EP2302023A2 (en) 2002-10-04 2011-03-30 R.T. Vanderbilt Company, Inc. Synergistic organoborate compositions and lubricating compositions containing same
EP2436753A1 (en) 2002-10-04 2012-04-04 R.T. Vanderbilt Company Inc. Synergistic organoborate compositions and lubricating compositions containing same
EP2460870A1 (en) 2002-10-04 2012-06-06 R.T. Vanderbilt Company, Inc. Synergistic organoborate compositions and lubricating compositions containing same
EP2366762A1 (en) 2002-10-04 2011-09-21 R.T. Vanderbilt Company Inc. Synergistic organoborate compositions and lubricating compositions containing same
US20040147410A1 (en) * 2003-01-15 2004-07-29 Milner Jeffrey L Extended drain, thermally stable, gear oil formulations
US7888299B2 (en) 2003-01-15 2011-02-15 Afton Chemical Japan Corp. Extended drain, thermally stable, gear oil formulations
US20110092401A1 (en) * 2003-04-25 2011-04-21 Buitrago Juan A Gear oil having low copper corrosion properties
US8536102B2 (en) 2003-04-25 2013-09-17 Chevron Oronite Company Llc Gear oil having low copper corrosion properties
US8389449B2 (en) 2003-04-25 2013-03-05 Chevron Oronite Company Llc Gear oil having low copper corrosion properties
US8409627B2 (en) 2003-06-17 2013-04-02 Osmose, Inc. Particulate wood preservative and method for producing the same
US20090280185A1 (en) * 2003-06-17 2009-11-12 Phibrowood, Llc Particulate wood preservative and method for producing the same
US8871277B2 (en) 2003-06-17 2014-10-28 Osmose, Inc. Particulate wood preservative and method for producing the same
US6933351B2 (en) 2003-06-20 2005-08-23 Infineum International Limited Process for forming polyalkenyl acylating agents
US20040260027A1 (en) * 2003-06-20 2004-12-23 Michaud Vincent Jean Marie Process for forming polyalkenyl acylating agents
US20040260032A1 (en) * 2003-06-20 2004-12-23 Irving Matthew David Low sediment process for thermally reacting highly reactive polymers and enophiles
US7339007B2 (en) 2003-06-20 2008-03-04 Infineum International Limited Low sediment process for thermally reacting highly reactive polymers and enophiles
US20050065043A1 (en) * 2003-09-23 2005-03-24 Henly Timothy J. Power transmission fluids having extended durability
US20070054813A1 (en) * 2003-09-25 2007-03-08 Chip Hewette Boron free automotive gear oil
US20050070446A1 (en) * 2003-09-25 2005-03-31 Ethyl Petroleum Additives, Inc. Boron free automotive gear oil
EP2230292A1 (en) 2003-11-10 2010-09-22 Afton Chemical Corporation Methods of lubricating transmissions
US20100279901A1 (en) * 2003-11-10 2010-11-04 Iyer Ramnath N Methods for providing steel-on-steel friction and/or steel-on-paper friction with lubricant compositions for power transmitting fluids
US9267093B2 (en) 2003-11-10 2016-02-23 Afton Chemical Corporation Methods for providing steel-on-steel friction and/or steel-on-paper friction with lubricant compositions for power transmitting fluids
US20050101494A1 (en) * 2003-11-10 2005-05-12 Iyer Ramnath N. Lubricant compositions for power transmitting fluids
US20080009426A1 (en) * 2003-11-10 2008-01-10 Iyer Ramnath N Lubricant Compositions and Methods Comprising Dispersant and Detergent
US20050101497A1 (en) * 2003-11-12 2005-05-12 Saathoff Lee D. Compositions and methods for improved friction durability in power transmission fluids
US20080090744A1 (en) * 2003-11-12 2008-04-17 Saathoff Lee D Compositions and Methods for Improved Friction Durability in Power Transmission Fluids
US20050192185A1 (en) * 2004-02-27 2005-09-01 Saathoff Lee D. Power transmission fluids
US7947636B2 (en) 2004-02-27 2011-05-24 Afton Chemical Corporation Power transmission fluids
EP1568759A2 (en) 2004-02-27 2005-08-31 Afton Chemical Corporation Power transmission fluids
US20050202979A1 (en) * 2004-03-10 2005-09-15 Ethyl Petroleum Additives, Inc. Power transmission fluids with enhanced extreme pressure characteristics
US20050250656A1 (en) * 2004-05-04 2005-11-10 Masahiro Ishikawa Continuously variable transmission fluid
US8722198B2 (en) 2004-05-17 2014-05-13 Osmose, Inc. Method of preserving wood by injecting particulate wood preservative slurry
US9314030B2 (en) 2004-05-17 2016-04-19 Koppers Performance Chemicals Inc. Particulate wood preservative and method for producing same
US20090223408A1 (en) * 2004-05-17 2009-09-10 Phibrowood, Llc Use of Sub-Micron Copper Salt Particles in Wood Preservation
US20050255251A1 (en) * 2004-05-17 2005-11-17 Hodge Robert L Composition, method of making, and treatment of wood with an injectable wood preservative slurry having biocidal particles
US8158208B2 (en) 2004-05-17 2012-04-17 Osmose, Inc. Method of preserving wood by injecting particulate wood preservative slurry
US20060003905A1 (en) * 2004-07-02 2006-01-05 Devlin Cathy C Additives and lubricant formulations for improved corrosion protection
US20060025314A1 (en) * 2004-07-28 2006-02-02 Afton Chemical Corporation Power transmission fluids with enhanced extreme pressure and antiwear characteristics
EP1624043A2 (en) 2004-07-28 2006-02-08 Afton Chemical Corporation Power transmission fluids with enhanced extreme pressure and antiwear characteristics
EP1640440A1 (en) 2004-09-22 2006-03-29 Infineum International Limited Friction and/or wear reduction in manual or automated manual transmissions
US20090143478A1 (en) * 2004-10-08 2009-06-04 Phibrowood, Llc Milled Submicron Organic Biocides With Narrow Particle Size Distribution, and Uses Thereof
US20080213608A1 (en) * 2004-10-08 2008-09-04 Richardson Hugh W Milled Submicron Chlorothalonil With Narrow Particle Size Distribution, and Uses Thereof
US20060075923A1 (en) * 2004-10-12 2006-04-13 Richardson H W Method of manufacture and treatment of wood with injectable particulate iron oxide
US9775350B2 (en) 2004-10-14 2017-10-03 Koppers Performance Chemicals Inc. Micronized wood preservative formulations in organic carriers
US20060122073A1 (en) * 2004-12-08 2006-06-08 Chip Hewette Oxidation stable gear oil compositions
EP1669436A1 (en) 2004-12-08 2006-06-14 Afton Chemical Corporation Oxidation stable gear oil compositions
US7485734B2 (en) 2005-01-28 2009-02-03 Afton Chemical Corporation Seal swell agent and process therefor
US20060173217A1 (en) * 2005-01-28 2006-08-03 Abbas Kadkhodayan Seal swell agent and process therefor
EP2116590A1 (en) 2005-02-18 2009-11-11 Infineum International Limited Soot dispersants and lubricating oil compositions containing same
WO2006094011A2 (en) 2005-03-01 2006-09-08 R.T. Vanderbilt Company, Inc. Molybdenum dialkyldithiocarbamate compositions and lubricating compositions containing the same
US8557752B2 (en) 2005-03-23 2013-10-15 Afton Chemical Corporation Lubricating compositions
US20060217273A1 (en) * 2005-03-23 2006-09-28 Nubar Ozbalik Lubricating compositions
US20060223716A1 (en) * 2005-04-04 2006-10-05 Milner Jeffrey L Tractor fluids
US20060252660A1 (en) * 2005-05-09 2006-11-09 Akhilesh Duggal Hydrolytically stable viscosity index improves
US20060264339A1 (en) * 2005-05-19 2006-11-23 Devlin Mark T Power transmission fluids with enhanced lifetime characteristics
EP1728848A1 (en) 2005-06-01 2006-12-06 Infineum International Limited Use of unsaturated olefin polymers to improve the compatibility between nitrile rubber seals and lubricating oil compositions
US20070004603A1 (en) * 2005-06-30 2007-01-04 Iyer Ramnath N Methods for improved power transmission performance and compositions therefor
US20070000745A1 (en) * 2005-06-30 2007-01-04 Cameron Timothy M Methods for improved power transmission performance
US20070042916A1 (en) * 2005-06-30 2007-02-22 Iyer Ramnath N Methods for improved power transmission performance and compositions therefor
US8080500B2 (en) 2005-07-12 2011-12-20 King Industries, Inc. Amine tungstates and lubricant compositions
US7820602B2 (en) 2005-07-12 2010-10-26 King Industries, Inc. Amine tungstates and lubricant compositions
US20070042917A1 (en) * 2005-07-12 2007-02-22 Ramanathan Ravichandran Amine Tungstates and Lubricant Compositions
US20090029888A1 (en) * 2005-07-12 2009-01-29 Ramanathan Ravichandran Amine tungstates and lubricant compositions
US20080194440A1 (en) * 2005-07-12 2008-08-14 Ramanathan Ravichandran Amine tungstates and lubricant compositions
US20070078066A1 (en) * 2005-10-03 2007-04-05 Milner Jeffrey L Lubricant formulations containing extreme pressure agents
US20070142659A1 (en) * 2005-11-09 2007-06-21 Degonia David J Sulfur-containing, phosphorus-containing compound, its salt, and methods thereof
US7928260B2 (en) 2005-11-09 2011-04-19 Afton Chemical Corporation Salt of a sulfur-containing, phosphorus-containing compound, and methods thereof
US20070105728A1 (en) * 2005-11-09 2007-05-10 Phillips Ronald L Lubricant composition
US8299003B2 (en) 2005-11-09 2012-10-30 Afton Chemical Corporation Composition comprising a sulfur-containing, phosphorus-containing compound, and/or its salt, and uses thereof
US20070142660A1 (en) * 2005-11-09 2007-06-21 Degonia David J Salt of a sulfur-containing, phosphorus-containing compound, and methods thereof
US20070142237A1 (en) * 2005-11-09 2007-06-21 Degonia David J Lubricant composition
US20080319216A1 (en) * 2005-11-09 2008-12-25 Degonia David J Salt of a Sulfur-Containing, Phosphorus-Containing Compound, And Methods Thereof
US20070111906A1 (en) * 2005-11-12 2007-05-17 Milner Jeffrey L Relatively low viscosity transmission fluids
US20090298727A1 (en) * 2005-12-15 2009-12-03 The Lubrizol Corporation Lubricant Composition for a Final Drive Axle
US8153565B2 (en) 2005-12-15 2012-04-10 The Lubrizol Corporation Lubricant composition for a final drive axle
WO2007111741A3 (en) * 2005-12-15 2008-04-03 Lubrizol Corp Lubricant composition for a final drive axle
WO2007111741A2 (en) * 2005-12-15 2007-10-04 The Lubrizol Corporation Lubricant composition for a final drive axle
US20070259792A1 (en) * 2006-03-22 2007-11-08 Null Volker K Functional fluid compositions
US20070259016A1 (en) * 2006-05-05 2007-11-08 Hodge Robert L Method of treating crops with submicron chlorothalonil
US20070270317A1 (en) * 2006-05-19 2007-11-22 Milner Jeffrey L Power Transmission Fluids
US7879775B2 (en) 2006-07-14 2011-02-01 Afton Chemical Corporation Lubricant compositions
US7902133B2 (en) 2006-07-14 2011-03-08 Afton Chemical Corporation Lubricant composition
US20080015127A1 (en) * 2006-07-14 2008-01-17 Loper John T Boundary friction reducing lubricating composition
US20080015125A1 (en) * 2006-07-14 2008-01-17 Devlin Mark T Lubricant compositions
US20080015124A1 (en) * 2006-07-14 2008-01-17 Devlin Mark T Lubricant composition
WO2008013698A1 (en) 2006-07-21 2008-01-31 Exxonmobil Research And Engineering Company Method for lubricating heavy duty geared apparatus
US20080051305A1 (en) * 2006-08-28 2008-02-28 Devlin Mark T Lubricant composition
US7833953B2 (en) 2006-08-28 2010-11-16 Afton Chemical Corporation Lubricant composition
US20080119377A1 (en) * 2006-11-22 2008-05-22 Devlin Mark T Lubricant compositions
US20080182768A1 (en) * 2007-01-31 2008-07-31 Devlin Cathy C Lubricant composition for bio-diesel fuel engine applications
DE102008005330A1 (en) 2007-01-31 2008-08-07 Afton Chemical Corp. Lubricant composition for biodiesel fuel engine uses
EP1959003A2 (en) 2007-02-08 2008-08-20 Infineum International Limited Soot dispersants and lubricating oil compositions containing same
EP1970430A2 (en) 2007-03-09 2008-09-17 Afton Chemical Corporation Fuel composition containing a hydrocarbyl-substituted succinimide
US9011556B2 (en) 2007-03-09 2015-04-21 Afton Chemical Corporation Fuel composition containing a hydrocarbyl-substituted succinimide
US20080274921A1 (en) * 2007-05-04 2008-11-06 Ian Macpherson Environmentally-Friendly Lubricant Compositions
EP2420553A1 (en) 2007-05-04 2012-02-22 Afton Chemical Corporation Environmentally-Friendly Lubricant Compositions
US20100152078A1 (en) * 2007-05-04 2010-06-17 Ian Macpherson Environmentally-friendly lubricant compositions
EP2017329A1 (en) 2007-05-04 2009-01-21 Afton Chemical Corporation Environmentally-Friendly Lubricant Compositions
US20110010985A1 (en) * 2007-05-22 2011-01-20 Peter Wangqi Hou Fuel Additive to Control Deposit Formation
WO2008154334A1 (en) 2007-06-08 2008-12-18 Infineum International Limited Additives and lubricating oil compositions containing same
EP2028256A2 (en) 2007-06-29 2009-02-25 Infineum International Limited Lubricating oils having improved friction stability
CN101343591B (en) 2007-06-29 2013-03-27 英菲诺姆国际有限公司 Lubricating oils having improved friction stability
CN101343589B (en) 2007-06-29 2013-04-03 英菲诺姆国际有限公司 Boron-containing lubricating oils having improved friction stability
EP2028257A2 (en) 2007-06-29 2009-02-25 Infineum International Limited Boron-containing lubricating oils having improved friction stability
US20090005276A1 (en) * 2007-06-29 2009-01-01 Watts Raymond F Boron-Containing Lubricating Oils Having Improved Friction Stability
US8623797B2 (en) * 2007-06-29 2014-01-07 Infineum International Limited Boron-containing lubricating oils having improved friction stability
US20090005277A1 (en) * 2007-06-29 2009-01-01 Watts Raymond F Lubricating Oils Having Improved Friction Stability
US20090011963A1 (en) * 2007-07-06 2009-01-08 Afton Chemical Corporation Truck fleet fuel economy by the use of optimized engine oil, transmission fluid, and gear oil
EP2025737A1 (en) 2007-08-01 2009-02-18 Afton Chemical Corporation Environmentally-friendly fuel compositions
US20090031614A1 (en) * 2007-08-01 2009-02-05 Ian Macpherson Environmentally-Friendly Fuel Compositions
US20090071067A1 (en) * 2007-09-17 2009-03-19 Ian Macpherson Environmentally-Friendly Additives And Additive Compositions For Solid Fuels
EP2042582A2 (en) 2007-09-24 2009-04-01 Afton Chemical Corporation Surface passivation and to methods for the reduction of fuel thermal degradation deposits
WO2009045979A1 (en) 2007-10-03 2009-04-09 The Lubrizol Corporation Lubricants that decrease micropitting for industrial gears
US20090156449A1 (en) * 2007-12-12 2009-06-18 Rowland Robert G Alkylated 1,3-benzenediamine compounds and methods for producing same
US8563489B2 (en) 2007-12-12 2013-10-22 Chemtura Corporation Alkylated 1,3-benzenediamine compounds and methods for producing same
EP2075315A1 (en) 2007-12-12 2009-07-01 Infineum International Limited Additive Compositions with Michael adducts of N-substituted phenylenediamines
US20090156441A1 (en) * 2007-12-12 2009-06-18 Rowland Robert G Cycloalkyl phenylenediamines as deposit control agents for lubricants
EP2075264A1 (en) 2007-12-26 2009-07-01 Infineum International Limited Method of forming polyalkene substituted carboxylic acid compositions
EP2083063A1 (en) 2008-01-22 2009-07-29 Infineum International Limited Lubricating oil composition
US20090192061A1 (en) * 2008-01-24 2009-07-30 Boegner Philip J Olefin copolymer dispersant vi improver and lubricant compositions and uses thereof
US8420583B2 (en) 2008-01-24 2013-04-16 Afton Chemical Corporation Olefin copolymer dispersant VI improver and lubricant compositions and uses thereof
EP2083024A1 (en) 2008-01-24 2009-07-29 Afton Chemical Corporation Olefin copolymer dispersant VI improver and lubricant compositions and uses thereof
EP2090642A1 (en) 2008-02-08 2009-08-19 Infineum International Limited Engine lubrication
DE102009012567A1 (en) 2008-03-11 2009-10-01 Afton Chemical Corp. Clutch-only transmission fluid useful for lubrication comprises oil formulated with additive components having metal detergent, phosphorus-based wear preventative, phosphorylated and boronated dispersant, sulfurized extreme pressure agent
US20090233822A1 (en) * 2008-03-11 2009-09-17 Afton Chemical Corporation Ultra-low sulfur clutch-only transmission fluids
US8546311B2 (en) 2008-03-11 2013-10-01 Volkswagen Aktiengesellsschaft Method for lubricating a clutch-only automatic transmission component requiring lubrication
US8703669B2 (en) 2008-03-11 2014-04-22 Afton Chemical Corporation Ultra-low sulfur clutch-only transmission fluids
DE102009001301A1 (en) 2008-03-11 2009-09-24 Audi Ag A method for lubricating a component for the clutch of an automatic transmission which requires lubrication
WO2009119831A1 (en) 2008-03-28 2009-10-01 富士フイルム株式会社 Composition and method for forming coating film
EP2107102A2 (en) 2008-04-04 2009-10-07 Afton Chemical Corporation A succinimide lubricity additive for diesel fuel
US20090249683A1 (en) * 2008-04-04 2009-10-08 Schwab Scott D Succinimide lubricity additive for diesel fuel and a method for reducing wear scarring in an engine
US8690968B2 (en) 2008-04-04 2014-04-08 Afton Chemical Corporation Succinimide lubricity additive for diesel fuel and a method for reducing wear scarring in an engine
EP2161326A1 (en) 2008-09-05 2010-03-10 Infineum International Limited Lubricating oil compositions
EP2163602A1 (en) 2008-09-05 2010-03-17 Infineum International Limited A lubricating oil composition
US8709108B2 (en) 2008-09-24 2014-04-29 Afton Chemical Corporation Fuel compositions
US20100075876A1 (en) * 2008-09-24 2010-03-25 David John Claydon Fuel compositions
EP2620207A2 (en) 2008-10-31 2013-07-31 Calera Corporation Non-cementitious compositions comprising CO2 sequestering additives
US9133581B2 (en) 2008-10-31 2015-09-15 Calera Corporation Non-cementitious compositions comprising vaterite and methods thereof
WO2010077630A1 (en) 2008-12-09 2010-07-08 The Lubrizol Corporation Lubricating composition containing a compound derived from a hydroxy-carboxylic acid
EP2206764A1 (en) 2008-12-23 2010-07-14 Infineum International Limited Aniline compounds as ashless TBN sources and lubricating oil compositions containing same
EP2233554A1 (en) 2009-03-27 2010-09-29 Infineum International Limited Lubricating oil compositions
EP2236590A1 (en) 2009-04-01 2010-10-06 Infineum International Limited Lubricating oil composition
EP2239314A1 (en) 2009-04-06 2010-10-13 Infineum International Limited Lubricating oil composition
EP2290038A2 (en) 2009-08-24 2011-03-02 Infineum International Limited A lubricating oil composition
EP2290041A2 (en) 2009-08-24 2011-03-02 Infineum International Limited A lubricating oil composition
EP2290043A1 (en) 2009-08-24 2011-03-02 Infineum International Limited A lubricating oil composition comprising metal dialkyldithiophosphate and carbodiimide
EP2365049A1 (en) 2009-08-24 2011-09-14 Infineum International Limited Use of a lubricating additive
US20110054126A1 (en) * 2009-08-28 2011-03-03 Chemtura Corporation Two-stage process and system for forming high viscosity polyalphaolefins
WO2011025636A1 (en) 2009-08-28 2011-03-03 Chemtura Corporation Two-stage process and system for forming high viscosity polyalphaolefins
US8080699B2 (en) 2009-08-28 2011-12-20 Chemtura Corporation Two-stage process and system for forming high viscosity polyalphaolefins
WO2011026990A1 (en) 2009-09-07 2011-03-10 Shell Internationale Research Maatschappij B.V. Lubricating compositions
WO2011034829A1 (en) 2009-09-16 2011-03-24 The Lubrizol Corporation Lubricating composition containing an ester
DE202009013309U1 (en) 2009-10-05 2010-03-04 Afton Chemical Corp. Fuel and fuel compositions
EP2169034A2 (en) 2009-10-05 2010-03-31 Afton Chemical Corporation Fuel compositions
EP2319904A1 (en) 2009-10-29 2011-05-11 Infineum International Limited Lubrication and lubricating oil compositions comprising phenylene diamines
WO2011059583A1 (en) 2009-10-29 2011-05-19 Chemtura Corporation Lubrication and lubricating oil compositions
US8415284B2 (en) 2009-11-05 2013-04-09 Afton Chemical Corporation Olefin copolymer VI improvers and lubricant compositions and uses thereof
US20110105371A1 (en) * 2009-11-05 2011-05-05 Afton Chemical Corporation Olefin copolymer vi improvers and lubricant compositions and uses thereof
EP2325291A1 (en) 2009-11-05 2011-05-25 Afton Chemical Corporation Olefin Copolymer VI improvers and lubricant compositions and uses thereof
WO2011066142A1 (en) 2009-11-30 2011-06-03 The Lubrizol Corporation Stabilized blends containing friction modifiers
WO2011066145A1 (en) 2009-11-30 2011-06-03 The Lubrizol Corporation Stabilized blends containing friction modifiers
WO2011066144A1 (en) 2009-11-30 2011-06-03 The Lubrizol Corporation Stabilized blends containing friction modifiers
EP2390306A1 (en) 2009-12-01 2011-11-30 Infineum International Limited A lubricating oil composition
WO2011102836A1 (en) 2010-02-19 2011-08-25 Infineum International Limited Wet friction clutch-lubricant systems providing high dynamic coefficients of friction through the use of borated detergents
US9365794B2 (en) 2010-02-19 2016-06-14 Infineum International Limited Wet friction clutch—lubricant systems providing high dynamic coefficients of friction through the use of borated detergents
WO2011102835A1 (en) 2010-02-19 2011-08-25 Toyota Jidosha Kabushiki Kaisha Wet friction clutch-lubricant systems providing high dynamic coefficients of friction through the use of sodium detergents
EP2363454A1 (en) 2010-02-23 2011-09-07 Infineum International Limited A lubricating oil composition
EP2366761A1 (en) 2010-03-09 2011-09-21 Infineum International Limited Morpholine derivatives as ashless TBN sources and lubricating oil compositions containing same
EP2371934A1 (en) 2010-03-31 2011-10-05 Infineum International Limited Lubricating oil composition
EP2371932A1 (en) 2010-04-01 2011-10-05 Infineum International Limited A lubricating oil composition
EP2374866A1 (en) 2010-04-06 2011-10-12 Infineum International Limited A lubricating oil composition comprising alkoxylated phenol-formaldehyde condensate
WO2011130142A1 (en) 2010-04-15 2011-10-20 The Lubrizol Corporation Low-ash lubricating oils for diesel engines
WO2011143418A1 (en) 2010-05-12 2011-11-17 Exxonmobil Research And Engineering Company Method for reducing one or more of deposits and friction of a lubricating oil
WO2011149810A1 (en) 2010-05-24 2011-12-01 The Lubrizol Corporation Lubricating composition
EP2420552A1 (en) 2010-08-19 2012-02-22 Infineum International Limited EGR Equipped Diesel Engines and Lubricating Oil Compositions
EP2453000A1 (en) 2010-11-08 2012-05-16 Infineum International Limited Lubricating Oil Composition comprising a hydrogenated imide derived from a Diels-Alder adduct of maleic anhydride and a furan
EP2457984A1 (en) 2010-11-30 2012-05-30 Infineum International Limited A lubricating oil composition
EP2479245A1 (en) 2011-01-19 2012-07-25 Afton Chemical Corporation Fuel additives and gasoline containing the additives
US9523057B2 (en) 2011-02-22 2016-12-20 Afton Chemical Corporation Fuel additives to maintain optimum injector performance
WO2012141855A1 (en) 2011-04-15 2012-10-18 R.T. Vanderbilt Company, Inc. Molybdenum dialkyldithiocarbamate compositions and lubricating compositions containing the same
WO2012162027A1 (en) 2011-05-26 2012-11-29 The Lubrizol Corporation Stabilized blends containing friction modifiers
WO2012162020A1 (en) 2011-05-26 2012-11-29 The Lubrizol Corporation Stabilized blends containing antioxidants
WO2013003406A1 (en) 2011-06-29 2013-01-03 Exxonmobil Research And Engineering Company Low viscosity engine oil with superior engine wear protection
WO2013003392A1 (en) 2011-06-30 2013-01-03 Exxonmobil Research And Engineering Company Method of improving pour point of lubricating compositions containing polyalkylene glycol mono ethers
US8586520B2 (en) 2011-06-30 2013-11-19 Exxonmobil Research And Engineering Company Method of improving pour point of lubricating compositions containing polyalkylene glycol mono ethers
WO2013003394A1 (en) 2011-06-30 2013-01-03 Exxonmobil Research And Engineering Company Lubricating compositions containing polyetheramines
WO2013003405A1 (en) 2011-06-30 2013-01-03 Exxonmobil Research And Engineering Company Lubricating compositions containing polyalkylene glycol mono ethers
EP2559748A1 (en) 2011-08-19 2013-02-20 Infineum International Limited Lubricating oil composition
EP2574656A1 (en) 2011-09-28 2013-04-03 Infineum International Limited Lubricating oil compositions
EP2584025A1 (en) 2011-10-21 2013-04-24 Infineum International Limited Lubricating oil composition
WO2013066915A1 (en) 2011-11-01 2013-05-10 Exxonmobil Research And Engineering Company Lubricants with improved low-temperature fuel economy
WO2013070376A2 (en) 2011-11-11 2013-05-16 Vanderbilt Chemicals, Llc Lubricant composition
WO2013074498A1 (en) 2011-11-14 2013-05-23 Exxonmobil Research And Engineering Company Method for improving engine fuel efficiency
WO2013082206A1 (en) 2011-12-02 2013-06-06 Exxonmobil Research And Engineering Company Method for improving engine wear and corrosion resistance
US9068134B2 (en) 2011-12-02 2015-06-30 Exxonmobil Research And Engineering Company Method for improving engine wear and corrosion resistance
WO2013090051A1 (en) 2011-12-13 2013-06-20 Chemtura Corporation Cross products and co-oligomers of phenylenediamines and aromatic amines as antioxidants for lubricants
DE102012223638A1 (en) 2011-12-21 2013-06-27 Infineum International Ltd. A method for reducing the rate of decrease of the basicity of a lubricating oil composition which is used in a motor
WO2013096532A1 (en) 2011-12-22 2013-06-27 Exxonmobil Research And Engineering Company Method for improving engine fuel efficiency
WO2013101882A1 (en) 2011-12-29 2013-07-04 The Lubrizol Corporation Limited slip friction modifiers for differentials
US9150812B2 (en) 2012-03-22 2015-10-06 Exxonmobil Research And Engineering Company Antioxidant combination and synthetic base oils containing the same
WO2013142110A1 (en) 2012-03-22 2013-09-26 Exxonmobil Research And Engineering Company Novel antioxidant combination and synthetic base oils containing the same
WO2013151911A1 (en) 2012-04-04 2013-10-10 The Lubrizol Corporation Bearing lubricants for pulverizing equipment
US9315756B2 (en) 2012-04-06 2016-04-19 Exxonmobil Research And Engineering Company Bio-feeds based hybrid group V base stocks and method of production thereof
US8703666B2 (en) 2012-06-01 2014-04-22 Exxonmobil Research And Engineering Company Lubricant compositions and processes for preparing same
WO2013181318A1 (en) 2012-06-01 2013-12-05 Exxonmobil Research And Engineering Company Lubricant compostions and processes for preparing same
US9228149B2 (en) 2012-07-02 2016-01-05 Exxonmobil Research And Engineering Company Enhanced durability performance of lubricants using functionalized metal phosphate nanoplatelets
WO2014008121A1 (en) 2012-07-02 2014-01-09 Exxonmobil Research And Engineering Company Enhanced durability performance of lubricants using functionalized metal phosphate nanoplatelets
EP2687583A1 (en) 2012-07-17 2014-01-22 Infineum International Limited Lubricating oil compositions containing sterically hindered amines as ashless TBN sources
EP2692840A1 (en) 2012-07-31 2014-02-05 Infineum International Limited Lubricating oil composition
EP2692839A1 (en) 2012-07-31 2014-02-05 Infineum International Limited A lubricating oil compostion comprising a corrosion inhibitor
US9422497B2 (en) 2012-09-21 2016-08-23 Exxonmobil Research And Engineering Company Synthetic lubricant basestocks and methods of preparation thereof
WO2014066444A1 (en) 2012-10-24 2014-05-01 Exxonmobil Research And Engineering Comapny Functionalized polymers and oligomers as corrosion inhibitors and antiwear additives
US9487729B2 (en) 2012-10-24 2016-11-08 Exxonmobil Chemical Patents Inc. Functionalized polymers and oligomers as corrosion inhibitors and antiwear additives
WO2014065984A1 (en) 2012-10-24 2014-05-01 Exxonmobil Reearch And Engineering Company High viscosity index lubricating oil base stock viscosity modifier combinations, and lubricating oils derived therefrom
EP2740782A1 (en) 2012-12-10 2014-06-11 Infineum International Limited Lubricating oil compositions containing sterically hindered amines as ashless tbn sources
WO2014105312A1 (en) 2012-12-28 2014-07-03 Chevron Oronite Company Llc Ultra-low saps lubricants for internal combustion engines
WO2014107314A1 (en) 2013-01-03 2014-07-10 Exxonmobil Research And Engineering Company Lubricating compositions having improved shear stability
WO2014107315A1 (en) 2013-01-04 2014-07-10 Exxonmobil Research And Engineering Company Method for improving engine fuel efficiency
WO2014137580A1 (en) 2013-03-07 2014-09-12 The Lubrizol Corporation Limited slip friction modifiers for differentials
WO2014158533A1 (en) 2013-03-14 2014-10-02 Exxonmobil Research And Engineering Company Lubricating composition providing high wear resistance
WO2014158602A1 (en) 2013-03-14 2014-10-02 Exxonmobil Research And Engineering Company Method for improving emulsion characteristics of engine oils
WO2014149406A1 (en) 2013-03-15 2014-09-25 Exxonmobil Research And Engineering Company Method for improving thermal -oxidative stability and elastomer compatibility
US9062269B2 (en) 2013-03-15 2015-06-23 Exxonmobil Research And Engineering Company Method for improving thermal-oxidative stability and elastomer compatibility
WO2014184068A1 (en) 2013-05-14 2014-11-20 Basf Se Lubricating oil composition with enhanced energy efficiency
US9708561B2 (en) 2013-05-14 2017-07-18 Basf Se Lubricating oil composition with enhanced energy efficiency
WO2014184062A1 (en) 2013-05-17 2014-11-20 Basf Se The use of polytetrahydrofuranes in lubricating oil compositions
US9938484B2 (en) 2013-05-17 2018-04-10 Basf Se Use of polytetrahydrofuranes in lubricating oil compositions
EP2843033A1 (en) 2013-08-15 2015-03-04 Infineum International Limited Transmission fluid compositions for improved energy efficiency
EP2837675A1 (en) 2013-08-15 2015-02-18 Infineum International Limited Automotive transmission fluid compositions for improved energy efficiency
WO2015050690A1 (en) 2013-10-03 2015-04-09 Exxonmobil Research And Engineering Company Compositions with improved varnish control properties
WO2015078707A1 (en) 2013-11-26 2015-06-04 Basf Se The use of polyalkylene glycol esters in lubricating oil compositions
WO2015095336A1 (en) 2013-12-18 2015-06-25 Chevron Phillips Chemical Company Lp Method for making polyolefins using aluminum halide catalyzed oligomerization of olefins
US9708549B2 (en) 2013-12-18 2017-07-18 Chevron Phillips Chemical Company Lp Method for making polyalphaolefins using aluminum halide catalyzed oligomerization of olefins
WO2015099820A1 (en) 2013-12-23 2015-07-02 Exxonmobil Research And Engineering Company Method for improving engine fuel efficiency
US9885004B2 (en) 2013-12-23 2018-02-06 Exxonmobil Research And Engineering Company Method for improving engine fuel efficiency
WO2015099821A1 (en) 2013-12-23 2015-07-02 Exxonmobil Research And Engineering Company Method for improving engine fuel efficiency
WO2015099907A1 (en) 2013-12-23 2015-07-02 Exxonmobil Research And Engineering Company Low viscosity ester lubricant and method for using
WO2015099819A1 (en) 2013-12-23 2015-07-02 Exxonmobil Research And Engineering Company Method for improving engine fuel efficiency
US9506008B2 (en) 2013-12-23 2016-11-29 Exxonmobil Research And Engineering Company Method for improving engine fuel efficiency
US9914893B2 (en) 2014-01-28 2018-03-13 Basf Se Use of alkoxylated polyethylene glycols in lubricating oil compositions
EP2913384A1 (en) 2014-02-26 2015-09-02 Infineum International Limited A lubricating oil composition
EP2937408A1 (en) 2014-04-22 2015-10-28 Basf Se Lubricant composition comprising an ester of a C17 alcohol mixture
EP2940110A1 (en) 2014-04-29 2015-11-04 Infineum International Limited Lubricating oil compositions
US9896634B2 (en) 2014-05-08 2018-02-20 Exxonmobil Research And Engineering Company Method for preventing or reducing engine knock and pre-ignition
WO2015171292A1 (en) 2014-05-08 2015-11-12 Exxonmobil Research And Engineering Company Method for preventing or reducing engine knock and pre-ignition
WO2015171978A1 (en) 2014-05-09 2015-11-12 Exxonmobil Research And Engineering Company Method for preventing or reducing low speed pre-ignition
WO2015171981A1 (en) 2014-05-09 2015-11-12 Exxonmobil Research And Engineering Company Method for preventing or reducing low speed pre-ignition
WO2015171980A1 (en) 2014-05-09 2015-11-12 Exxonmobil Research And Engineering Company Method for preventing or reducing low speed pre-ignition
US10000720B2 (en) 2014-05-22 2018-06-19 Basf Se Lubricant compositions containing beta-glucans
US9506009B2 (en) 2014-05-29 2016-11-29 Exxonmobil Research And Engineering Company Lubricating oil compositions with engine wear protection
WO2015183455A1 (en) 2014-05-29 2015-12-03 Exxonmobil Research And Engineering Company Lubricating oil compositions with engine wear protection
US9944877B2 (en) 2014-09-17 2018-04-17 Exxonmobil Research And Engineering Company Composition and method for preventing or reducing engine knock and pre-ignition in high compression spark ignition engines
WO2016043944A1 (en) 2014-09-17 2016-03-24 Exxonmobil Research And Engineering Company Composition and method for preventing or reducing engine knock and pre-ignition in high compression spark ignition engines
US9957459B2 (en) 2014-11-03 2018-05-01 Exxonmobil Research And Engineering Company Low transition temperature mixtures or deep eutectic solvents and processes for preparation thereof
WO2016073149A1 (en) 2014-11-03 2016-05-12 Exxonmobil Research And Engineering Company Low transition temperature mixtures or deep eutectic solvents and processes for preparation thereof
US9957463B2 (en) 2014-11-05 2018-05-01 Infineum International Limited Power transmitting fluids with improved materials compatibility
US9732301B2 (en) 2014-11-05 2017-08-15 Infineum International Limited Power transmitting fluids with improved materials compatibility
DE102015118989A1 (en) 2014-11-05 2016-05-12 Infineum International Ltd. Power transmission fluids having improved materials compatibility
EP3034587A1 (en) 2014-12-19 2016-06-22 Infineum International Limited Marine engine lubrication
WO2016106211A1 (en) 2014-12-24 2016-06-30 Exxonmobil Research And Engineering Company Methods for authentication and identification of petroleum products
WO2016106214A1 (en) 2014-12-24 2016-06-30 Exxonmobil Research And Engineering Company Methods for determining condition and quality of petroleum products
US10000721B2 (en) 2014-12-30 2018-06-19 Exxonmobil Research And Engineering Company Lubricating oil compositions with engine wear protection
WO2016109322A1 (en) 2014-12-30 2016-07-07 Exxonmobil Research And Engineering Company Lubricating oil compositions containing encapsulated microscale particles
US10066184B2 (en) 2014-12-30 2018-09-04 Exxonmobil Research And Engineering Company Lubricating oil compositions containing encapsulated microscale particles
WO2016109325A1 (en) 2014-12-30 2016-07-07 Exxonmobil Research And Engineering Company Lubricating oil compositions containing encapsulated microscale particles
WO2016109382A1 (en) 2014-12-30 2016-07-07 Exxonmobil Research And Engineering Company Lubricating oil compositions with engine wear protection
WO2016109376A1 (en) 2014-12-30 2016-07-07 Exxonmobil Research And Engineering Company Lubricating oil compositions with engine wear protection
US10000717B2 (en) 2014-12-30 2018-06-19 Exxonmobil Research And Engineering Company Lubricating oil compositions containing encapsulated microscale particles
US9926509B2 (en) 2015-01-19 2018-03-27 Exxonmobil Research And Engineering Company Lubricating oil compositions with engine wear protection and solubility
WO2016138939A1 (en) 2015-03-03 2016-09-09 Basf Se Pib as high viscosity lubricant base stock
EP3085757A1 (en) 2015-04-23 2016-10-26 Basf Se Stabilization of alkoxylated polytetrahydrofuranes with antioxidants
WO2016191409A1 (en) 2015-05-28 2016-12-01 Exxonmobil Research And Engineering Company Composition and method for preventing or reducing engine knock and pre-ignition in high compression spark ignition engines
WO2016200606A1 (en) 2015-06-09 2016-12-15 Exxonmobil Research And Engineering Company Inverse micellar compositions containing lubricant additives
WO2017007670A1 (en) 2015-07-07 2017-01-12 Exxonmobil Research And Engineering Company Composition and method for preventing or reducing engine knock and pre-ignition in high compression spark ignition engines
EP3118285A1 (en) 2015-07-16 2017-01-18 Infineum International Limited Method of improving vehicle transmission operation through use of specific lubricant compositions
US9732300B2 (en) 2015-07-23 2017-08-15 Chevron Phillipa Chemical Company LP Liquid propylene oligomers and methods of making same
EP3124581A1 (en) 2015-07-30 2017-02-01 Infineum International Limited Dispersant additives and additive concentrates and lubricating oil compositions containing same
EP3135750A1 (en) 2015-08-26 2017-03-01 Infineum International Limited Lubricating oil compositions
EP3144372A1 (en) 2015-09-16 2017-03-22 Infineum International Limited Additive concentrates for the formulation of lubricating oil compositions
EP3153568A1 (en) 2015-10-05 2017-04-12 Infineum International Limited Additive concentrates for the formulation of lubricating oil compositions
WO2017117178A1 (en) 2015-12-28 2017-07-06 Exxonmobil Research And Engineering Company Bright stock production from deasphalted oil
EP3192858A1 (en) 2016-01-15 2017-07-19 Infineum International Limited Use of lubricating oil composition
WO2017146896A1 (en) 2016-02-26 2017-08-31 Exxonmobil Research And Engineering Company Lubricant compositions containing controlled release additives
WO2017146897A1 (en) 2016-02-26 2017-08-31 Exxonmobil Research And Engineering Company Lubricant compositions containing controlled release additives
EP3222698A1 (en) 2016-03-22 2017-09-27 Infineum International Limited Additive concentrates
WO2017172254A1 (en) 2016-03-31 2017-10-05 Exxonmobil Research And Engineering Company Lubricant compositions
US9951290B2 (en) 2016-03-31 2018-04-24 Exxonmobil Research And Engineering Company Lubricant compositions
US20170335226A1 (en) * 2016-05-23 2017-11-23 Infineum International Limited Highly Borated Dispersant Concentrates for Lubricating Oil Compositions and Methods for Forming Same
EP3252130A1 (en) 2016-06-03 2017-12-06 Infineum International Limited Additive package and lubricating oil composition
EP3257921A1 (en) 2016-06-14 2017-12-20 Infineum International Limited Lubricating oil additives
EP3263676A2 (en) 2016-06-30 2018-01-03 Infineum International Limited Lubricating oil compositions
WO2018013249A1 (en) 2016-07-12 2018-01-18 Chevron Phillips Chemical Company Lp Decene oligomers
WO2018026982A1 (en) 2016-08-03 2018-02-08 Exxonmobil Research And Engineering Company Lubricating engine oil for improved wear protection and fuel efficiency
WO2018027227A1 (en) 2016-08-05 2018-02-08 Rutgers, The State University Of New Jersey Thermocleavable friction modifiers and methods thereof
WO2018039571A1 (en) 2016-08-25 2018-03-01 Evonik Degussa Gmbh Amine alkenyl substituted succinimide reaction product fuel additives, compositions, and methods
WO2018048781A1 (en) 2016-09-12 2018-03-15 The Lubrizol Corporation Total base number boosters for marine diesel engine lubricating compositions
WO2018050484A1 (en) 2016-09-13 2018-03-22 Basf Se Lubricant compositions containing diurea compounds
EP3293246A1 (en) 2016-09-13 2018-03-14 Basf Se Lubricant compositions containing diurea compounds
WO2018053098A1 (en) 2016-09-14 2018-03-22 The Lubrizol Corporation Lubricating composition comprising sulfonate detergent and ashless hydrocarbyl phenolic compound
WO2018057377A1 (en) 2016-09-20 2018-03-29 Exxonmobil Research And Engineering Company Non-newtonian engine oil with superior engine wear protection and fuel economy
WO2018067902A1 (en) 2016-10-07 2018-04-12 Exxonmobil Research And Engineering Company Lubricating oil compositions for electric vehicle powertrains
WO2018067908A1 (en) 2016-10-07 2018-04-12 Exxonmobil Research And Engineering Company Low conductivity lubricating oils for electric and hybrid vehicles
WO2018067903A1 (en) 2016-10-07 2018-04-12 Exxonmobil Research And Engineering Company Method for controlling electrical conductivity of lubricating oils in electric vehicle powertrains
WO2018067905A1 (en) 2016-10-07 2018-04-12 Exxonmobil Research And Engineering Company Method for preventing or minimizing electrostatic discharge and dielectric breakdown in electric vehicle powertrains
WO2018067906A1 (en) 2016-10-07 2018-04-12 Exxonmobil Research And Engineering Company High conductivity lubricating oils for electric and hybrid vehicles
EP3315591A1 (en) 2016-10-28 2018-05-02 Basf Se Energy efficient lubricant compositions
EP3321347A1 (en) 2016-11-14 2018-05-16 Infineum International Limited Lubricating oil additives based on overbased gemini surfactant
WO2018175830A1 (en) 2017-03-24 2018-09-27 Exxonmobil Research And Engineering Company Method for improving engine fuel efficiency and energy efficiency

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