Patents Represented by Attorney James W. Adams, Jr.
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Patent number: 4110349Abstract: Substituted carboxylic acids of the type prepared by the alkylation of maleic anhydride with an olefin polymer (e.g., polybutene) are prepared by a two-step method which is more economical and efficient than previously known methods. In the first step, the alkylating hydrocarbon is reacted with an unsaturated dicarboxylic acid or derivative thereof in an amount of the latter equal to about 30-90% by weight of the amount required to afford the desired product, optionally in the presence of a small amount of chlorine. In the second step, additional acid or derivative thereof is added and the reaction is continued in the presence of added chlorine.Type: GrantFiled: June 11, 1976Date of Patent: August 29, 1978Assignee: The Lubrizol CorporationInventor: Jerome M. Cohen
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Patent number: 4108784Abstract: Condensation products made by reacting an alpha-hydroxyalkyl hydroxy-aromatic compound also having at least one non-fused hydrocarbyl substituent with at least one olefinic nitrile, carboxylic acid or carboxylic acid derivative are useful as additives for fuels and lubricants. The total number of carbon atoms in the non-fused hydrocarbyl substituents is at least about seven while the alpha-hydroxyalkyl group contains from one to about 36 carbons and the olefinic acid or nitrile reactant usually contains two to about forty carbon atoms. Products made from hydroxymethyl alkyl-substituted phenols and .alpha.,.beta.-olefinic acid derivatives such as maleic anhydride are particularly useful. Similarly useful post-treated products can be made from these condensation products by further reaction with alcohols, amines, metal salts or metals.Type: GrantFiled: April 19, 1976Date of Patent: August 22, 1978Assignee: The Lubrizol CorporationInventor: Charles Peterson Bryant
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Patent number: 4108783Abstract: Condensation products made by reacting an alphahaloalkyl hydroxy-aromatic compound also having at least one non-fused hydrocarbyl substituent with at least one olefinic nitrile, carboxylic acid or carboxylic acid derivative are useful as additives for fuels and lubricants. The number of carbon atoms in the aromatic hydrocarbyl compound's substituents are each about 25 while the haloalkyl group contains from one to about 36 carbons. The acid or nitrile reactant usually contains three to about forty carbons. Product made from halomethyl alkyl-substituted phenols and .alpha.,.beta.-olefinic diacid derivatives such as maleic anhydride are particularly useful. Similarly useful products can be made from these condensation products by further reacting their acid, acid derivative or nitrile groups with alcohols, polyols, monoamines, polyamines, metal salts or metals.Type: GrantFiled: May 10, 1976Date of Patent: August 22, 1978Assignee: The Lubrizol CorporationInventor: David Eugene Ripple
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Patent number: 4100082Abstract: Disclosed are combinations of amino phenols, wherein said phenols contain a substantially saturated hydrocarbon substituent of at least 10 aliphatic carbon atoms, and one or more detergent/dispersants selected from the group consisting of (I) neutral or basic metal salts of an organic sulfur acid, phenol or carboxylic acid; (II) hydrocarbylsubstituted amines wherein the hydrocarbyl substituent is substantially aliphatic and contains at least 12 carbon atoms; (III) acylated nitrogen-containing compounds having a substituent of at least 10 aliphatic carbon atoms; and (IV) nitrogen-containing condensates of a phenol, aldehyde and amino compound. Fuels and lubricants containing such combinations as additives are particularly useful in two-cycle (two-stroke) engines.Type: GrantFiled: January 28, 1976Date of Patent: July 11, 1978Assignee: The Lubrizol CorporationInventors: Donald Lynn Clason, John Francis Pindar, Jerome Martin Cohen
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Patent number: 4098708Abstract: Esters of alkyl-substituted hydroxyaromatic carboxylic acids (especially alkyl-substituted salicylic acids) and the like, in which the alkyl substituent contains at least about 10 carbon atoms, are useful as dispersant additives for lubricants and fuels. Particularly useful are esters in which the substituent is derived from propylene, 1-butene or isobutene and has a molecular weight of about 150-1750, and in which the alkyl moiety is derived from pentaerythritol. Such esters are preferably prepared by the reaction of the corresponding organic hydroxy compound with a vic-hydroxyalkyl ester of the salicylic acid.Type: GrantFiled: June 16, 1975Date of Patent: July 4, 1978Assignee: The Lubrizol CorporationInventor: Carl Walter Stuebe
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Patent number: 4094801Abstract: Magnesium-containing complexes are prepared by heating a mixture of magnesium hydroxide, magnesium oxide, hydrated magnesium oxide or a magnesium alkoxide; a carboxylic acid, a sulfonic acid, a pentavalent phosphorus acid, or an ester or salt of any of these; water; and an organic solubilizing agent (which may be liquid or solid at ambient temperature) for the acid or ester. The amount of magnesium is such as to provide a basic composition. The resulting complexes may be obtained in liquid (which may be thickened) or solid form, and are useful as additives for lubricants and fuels and as protective coating compositions for metal surfaces (such as automotive undercoats and frame coatings).Type: GrantFiled: January 18, 1977Date of Patent: June 13, 1978Assignee: The Lubrizol CorporationInventor: John Wesley Forsberg
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Patent number: 4094739Abstract: Microbial polysaccharides such as xanthan gum sometimes form cloudy suspensions rather than clear solutions when dispersed in water because of the presence of microbial cells therein. An aqueous polysaccharide solution (e.g., the fermentation broth) may be clarified by killing remaining microbial cells (e.g., by pasteurization) and conducting a second fermentation in the presence of an easily filterable microorganism capable of consuming said killed cells. The easily filterable microorganism is typically a fungus and preferably a mold such as the Trichoderma sp. molds. Following the second filtration, the cells of the easily filterable microorganism are preferably removed from the mixture, typically by filtration or centrifugation.Type: GrantFiled: December 27, 1976Date of Patent: June 13, 1978Assignee: The Lubrizol CorporationInventor: Calvin William Schroeck
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Patent number: 4090971Abstract: Amides of alkyl-substituted hydroxyaromatic carboxylic acids (especially alkyl-substituted salicylic acids) and the like, in which the alkyl substituent contains at least about 10 carbon atoms, are useful as dispersant additives for lubricants and fuels. Particularly useful are salicylamides in which the substituent is derived from propylene, 1-butene or isobutene and has a molecular weight of about 150-1750, and in which the amide moiety is derived from an alkylene polyamine. Such amides are preferably prepared by the reaction of the corresponding nitrogen-containing compound with a vic-hydroxyalkyl ester of the salicylic acid.Type: GrantFiled: June 16, 1975Date of Patent: May 23, 1978Assignee: The Lubrizol CorporationInventor: Donald Irvin Hoke
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Patent number: 4081387Abstract: Lubricating compositions comprising a major proportion of lubricating oil and a minor proportion of at least one additive of the formula:Y.sup.a --S--Y.sup.bwherein Y.sup.a corresponds to ##STR1## and Z is ##STR2## and each R.sup.1 and R.sup.2 is independently hydrocarbyl, hydrocarbyloxy and hydrocarbylmercapto of one to about 30 carbon atoms; R.sup.3 is hydrogen or hydrocarbyl of up to about 10 carbon atoms; R.sup.4 is hydrogen or lower alkyl; R.sup.5 and R.sup.6 are each independently hydrogen, hydrocarbyl, hydrocarbyloxy and hydrocarbylmercapto of one to about 10 carbon atoms; R.sup.7 is hydrogen or hydrocarbyl of one to about 30 carbon atoms; each X is independently oxygen or divalent sulfur; n is zero or an integer of one to about 10; n' is zero or an integer of one to about 9; Y.sup.b is--R.sup.8 --H or --R.sup.8 --S--R.sup.9wherein R.sup.8 is a divalent hydrocarbyl group of one to about 30 carbon atoms and R.sup.9 is hydrogen or Y.sup.Type: GrantFiled: March 25, 1977Date of Patent: March 28, 1978Assignee: The Lubrizol CorporationInventor: David Eugene Ripple
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Patent number: 4081386Abstract: Reaction mixtures made from reacting one or more substituted di- and triazines of the formula: ##STR1## wherein Q and Q' are each independently halo, hydrocarbyloxy of the formula --OR and hydrocarbyl of the formula --R, wherein each R independently contains up to about 20 carbon atoms, with the proviso that at least one of Q and Q' is either hydrocarbyloxy or halogen; X and X' are each independently oxygen, divalent sulfur, .dbd.NH, and .dbd.NR.sub.1 wherein R.sub.1 is hydrocarbyl up to about 20 carbon atoms; and each R' is independently hydrogen or hydrocarbyl of up to about 10 carbon atoms; with (B) one or more mercapto compounds such as mercaptans, thiolphosphorus acids, thiocarbamates, and thiocarbonates are useful in fuels and lubricants.Type: GrantFiled: October 1, 1976Date of Patent: March 28, 1978Assignee: The Lubrizol CorporationInventor: Roger L. Sowerby
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Lubricant compositions containing boron dispersant, VI improver, and aromatic carboxylic acid esters
Patent number: 4080303Abstract: Lubricant compositions comprising (I), a viscosity improving agent, (II) a boron-containing dispersant, and (III) an ester of an aromatic carboxylic acid having six to ten carbon atoms in the aromatic nucleus and a total of 6 to 40 aliphatic and alicyclic carbon atoms as well as additive concentrates for making such lubricant compositions are disclosed. Preferably, (I) is a carboxy-containing interpolymer in which some carboxy radicals are esterified and the remaining carboxy radicals are neutralized with an amino compound and (II) is a borated, acylated polyamino compound, having an acyl group containing at least 50 carbon atoms. These lubricant compositions are useful as automatic transmission fluids and the like.Type: GrantFiled: July 22, 1974Date of Patent: March 21, 1978Assignee: The Lubrizol CorporationInventors: Edward Joe Friihauf, Donald Leon Murfin -
Patent number: 4071327Abstract: Novel compositions, useful as additives for normally liquid fuels to impart dispersancy, anti-icing and rust inhibiting properties thereto, comprise salts of amines prepared by the Mannich reaction between a hydroxy-substituted aromatic compound, usually an alkylphenol in which the alkyl group contains at least about six carbon atoms; formaldehyde or a reversible polymer thereof; and a hydroxyalkyl-substituted amine such as diethanolamine. The acid portion of the salt is preferably derived from a carboxylic acid containing about 14-24 carbon atoms especially an aliphatic radical-substituted succinic acid or an acidic ester thereof. Epoxide adducts of such salts are useful for the same purposes.Type: GrantFiled: March 21, 1975Date of Patent: January 31, 1978Assignee: The Lubrizol CorporationInventor: Casper John Dorer, Jr.
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Patent number: 4070385Abstract: Compositions made by reaction of (A) at least one phosphorus acid compound of the formula: ##STR1## wherein each X is independently oxygen or divalent sulfur, M is hydrogen or an equivalent of metal or ammonium cation, R is a hydrogen atom or a hydrocarbyl or hydrocarbyloxy or hydrocarbyl mercapto group of about one to about thirty carbon atoms and R' is XM or R with the proviso that the total number of carbon atoms in both R and R' is at least two, with (B) at least one sulfo-containing compound of the formulae: ##STR2## wherein y is one or two, R.sup.3 is hydrogen or lower alkyl group, R.sup.2 is a divalent or trivalent hydrocarbyl group, R.sup.4 is a trivalent hydrocarbyl group, and Q is --OH, --OR.sup.3, --OM, an alkylene polyamine residue, or N(R.sub.3).sub.2, are novel and useful and have utility as, for example, additives for water-containing hydraulic fluids.Type: GrantFiled: March 15, 1977Date of Patent: January 24, 1978Assignee: The Lubrizol CorporationInventor: William Monroe Le Suer
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Patent number: 4067698Abstract: Compositions made by reacting (I) a metal phenoxide salt of a bridged phenol of 2 to about 20 phenol groups and (II) a carboxylic acid reagent containing from one to three carboxyl-based groups and a halogen-substituted hydrocarbon-based aliphatic or alicyclic group containing a halogen atom are useful as additives for lubricants and normally liquid fuels. Analogous thiophenoxide-based compositions are similarly useful. These compositions can also be used as intermediates for the preparation of other useful additive compositions through their reaction with alcohols, amino compounds, reactive small ring heterocycles and basically reacting metal compounds.Type: GrantFiled: August 27, 1975Date of Patent: January 10, 1978Assignee: The Lubrizol CorporationInventor: Thomas Frier Steckel
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Patent number: 4061474Abstract: Compositions made by reacting (I) a metal phenoxide substituted with at least one hydrocarbon-based group of at least about 30 carbon atoms with (II) a carboxylic acid reagent containing from one to three carboxyl-based groups and a halogen-substituted hydrocarbon-based aliphatic or alicyclic group containing a halogen atom are useful as additives for lubricants and normally liquid fuels. Analogous thiophenoxide-based compositions are similarly useful. These compositions are also useful as intermediates for the preparation of other useful additive compositions through their reaction with alcohols, amino compounds, reactive small ring heterocycles and basically reacting metal compounds.Type: GrantFiled: August 27, 1975Date of Patent: December 6, 1977Assignee: The Lubrizol CorporationInventor: Thomas Frier Steckel
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Patent number: 4061580Abstract: Thickened fracturing and acidizing fluids suitable for well treatment are prepared by adding certain amine salts to aqueous acid or salt solutions. The amines from which the amine salts are prepared are alkoxylated alkyl- or alkenylamines in which an alkyl or alkenyl group contains at least about 14 and preferably about 14-30 carbon atoms. Most often the alkyl or alkenyl group is oleyl, stearyl, or a mixture of groups derived from such fats as tallow or soybean oil. The especially preferred amines are the "Ethomeens" which are ethoxylated fatty amines.Type: GrantFiled: September 8, 1976Date of Patent: December 6, 1977Assignee: The Lubrizol CorporationInventor: Richard William Jahnke
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Patent number: 4058469Abstract: Compositions useful as lubricants and functional fluids comprise an oleaginous liquid of lubricating viscosity, typically a mineral oil, and an oxygen-, sulfur- or nitrogen-containing polyfunctional nitrile. The preferred nitriles are cyanoethylation products of alcohols, mercaptans and amines, and especially of alcohols. The polyfunctional nitrile serves as a seal swelling agent and/or demulsifier.Type: GrantFiled: December 5, 1975Date of Patent: November 15, 1977Assignee: The Lubrizol CorporationInventor: Donald Irvin Hoke
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Patent number: 4053428Abstract: Hydroxy aromatic compositions containing (a) a hydroxyl group bonded directly to a carbon of an aromatic nucleus, (b) a hydrocarbon-based substituent of at least about 50 aliphatic carbon atoms bonded directly to a carbon atom of an aromatic nucleus, (c) at least one methylol or lower hydrocarbyl substituted methylol substituent bonded directly to a carbon atom of an aromatic nucleus, and not having any alkylene linkages between carbon atoms of two aromatic nuclei are useful as additives for normally liquid fuels and lubricating oils. These hydroxy aromatic compositions are also useful as intermediates for preparing other additives for fuels and lubricants. Typical hydroxy aromatic compositions of the present invention are formed by reaction of formaldehyde with an alkenyl- or alkyl-substituted phenol wherein the alkyl or alkenyl substituent contains an average of about 50 carbon atoms.Type: GrantFiled: September 15, 1975Date of Patent: October 11, 1977Assignee: The Lubrizol CorporationInventors: John Francis Pindar, Jerome Martin Cohen, Charles Peterson Bryant
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Patent number: 4042513Abstract: Concentrates of N-substituted morpholines of the formula O(CH.sub.2 CH.sub.2).sub.2 NR'YR", wherein R' is a divalent organic radical of at least one to about 30 carbon atoms, Y ##STR1## or --NH.sup.3 --, R.sup.3 is a hydrogen atom or a hydrocarbyl radical of at least one carbon atom and R" is a monovalent hydrocarbon radical of at least 15 carbon atoms, are useful as additives for hydrocarbyl products. Particularly preferred embodiments of the invention include concentrates wherein Y is ##STR2## R' is 1,3-propylene and R" is a hydrocarbyl group of at least about forty carbon atoms. These concentrates have utility as, for example, additives for lubricant compositions.Type: GrantFiled: July 24, 1975Date of Patent: August 16, 1977Assignee: The Lubrizol CorporationInventors: Norman Anthony Meinhardt, Robert Widmer
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Patent number: 4036772Abstract: Esters made from (A) high molecular weight carboxylic acid reagents derived from low molecular weight ethylenically unsaturated carboxylic acid reagents and oxidized ethylene-propylene interpolymers and (B) mono- or polyhydric alcohols are useful in lubricant compositions and normally liquid fuel compositions as viscosity improving agents and sludge dispersants. Esters wherein the low molecular weight reagent is maleic anhydride and the alcohol is a polyol such as pentaerythritol are particularly useful.Type: GrantFiled: March 3, 1975Date of Patent: July 19, 1977Assignee: The Lubrizol CorporationInventor: Casper John Dorer, Jr.