# US 10,308,889 B1 · Lubricity additives for fuels > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,308,889 B1 - Document ID: US10308889B1 - Status: Granted - Kind: B1 - Application number: 16/054,354 - Filed: 2018-08-03 - Granted: 2019-06-04 - Earliest claimed: 2018-08-03 - Assignees: Afton Chemical Corporation; Shell Oil Company - Applicants: Afton Chemical Corporation - Inventors: William Colucci; Joseph Calderone; Joseph Russo - Web page: https://patentgrep.com/patent/US10308889B1 ## CPC - C10L 10/08: for improving lubricity; for reducing wear - C10L 1/14: Organic compounds - C10L 1/1883: {polycarboxylic acid} - C10L 1/221: {compounds of uncertain formula; reaction products where mixtures of compounds are obtained} - C10M 141/06: at least one of them being an organic nitrogen-containing compound - C10L 1/1881: {carboxylic group attached to an aliphatic carbon atom} - C10L 1/224: Amides; Imides {carboxylic acid amides, imides (C10L1/221, C10L1/2227 take precedence)} - C10L 1/238: obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds {(C10L1/221 takes precedence)} - C10L 1/2383: Polyamines or polyimines, or derivatives thereof {(poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C) (C10L1/221 takes precedence)} - C10L 1/2387: Polyoxyalkyleneamines {(poly)oxyalkylene amines and derivatives thereof (substituted by a macromolecular group containing 30C) (C10L1/221 takes precedence)} - C10L 2200/0259: Nitrogen containing compounds - C10L 2200/0484: Vegetable or animal oils - C10L 2270/023: for gasoline engines - C10M 2207/126: monocarboxylic - C10M 2215/28: Amides; Imides - C10N 2030/06: Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure - C10N 2030/56: {Boundary lubrication or thin film lubrication} - C10L: FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS - C10M: LUBRICATING COMPOSITIONS (well drilling compositions C09K8/02); USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION (mould release, i.e. separating, agents for metals B22C3/00, for plastics or substances in a plastic state, in general B29C33/56, for glass C03B40/02; textile lubricating compositions D06M11/00, D06M13/00, D06M15/00; immersion oils for microscopy G02B21/33) - C10N: INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS ## Abstract Fuel additive compositions that include synergistic mixtures of one or more neutral lubricity additives and one or more monoacidic lubricity additives to provide wear and/or friction reduction in fuels. ## Claims ### Claim 1 A gasoline additive providing lubricity, the gasoline additive comprising a lubricity additive mixture of (i) at least one neutral lubricity additive prepared by reacting a hydrocarbyl-substituted succinic anhydride with ammonia wherein the hydrocarbyl substituent includes 8 to 20 carbons and (ii) at least one linear monocarboxylic acid or salt thereof having a carbon chain of 16 to 20 carbons, the linear monocarboxylic acid or salt thereof being saturated, unsaturated, or including mixtures thereof, and when (ii) is the at least one linear monocarboxylic acid, a weight ratio of (i) an amount of the at least one neutral lubricity additive divided by (ii) an amount of the at least one linear monocarboxylic acid is about 0.2 to about 5 and when (ii) is the at least one linear monocarboxylic acid salt, a weight ratio of (i) an amount of the at least one neutral lubricity additive divided by (ii) an amount of the at least one linear monocarboxylic acid salt is about 2 to about 27.8; and about 0.6 to about 10.8 PTB of (i) and about 0.3 to about 1.0 PTB of (ii) are used in a spark-ignitable fuel together. ### Claim 2 (depends on 1) The gasoline additive of claim 1, wherein the hydrocarbyl substituent of the succinic anhydride is a linear or branched C16 to C18 group. ### Claim 3 (depends on 1) The gasoline additive of claim 1, wherein the at least one linear monocarboxylic acid or salt thereof includes a linear carbon chain having 16 to 18 carbon atoms. ### Claim 4 (depends on 1) The gasoline additive of claim 1, wherein the at least one linear monocarboxylic acid or salt thereof is selected from the group consisting of palmitic acid, margaric acid, stearic acid, arachidic acid, oleic acid, palmitoleic acid, linoleic acid, linolenic acid, eleosteric acid, arachidonic acid, linseed oil fatty acid, palm oil fatty acid, rapeseed oil fatty acid, soybean oil fatty acid, sunflower oil fatty acid, tall oil fatty acid, mixtures thereof, and salts thereof. ### Claim 5 (depends on 1) The gasoline additive of claim 1, further comprising a detergent selected from the group consisting of (i) one or more Mannich reaction products formed by condensing a long chain aliphatic hydrocarbon-substituted phenol or cresol with an aldehyde, and an amine, (ii) long chain aliphatic hydrocarbons having an amine or a polyamine attached thereto, (iii) fuel-soluble nitrogen containing salts, amides, imides, succinimides, imidazolines, esters, and long chain aliphatic hydrocarbon-substituted dicarboxylic acids or their anhydrides or mixtures thereof, (iv) polyetheramines; (v) quaternary amines and salts thereof; and (vi) combinations thereof. ### Claim 6 A fuel comprising a major amount of a spark-ignitable fuel and a minor amount of a lubricity additive mixture, the fuel including (i) about 0.6 to about 10.8 PTB of at least one neutral lubricity additive prepared by reacting a hydrocarbyl-substituted succinic anhydride with ammonia wherein the hydrocarbyl substituent includes 8 to 20 carbons and (ii) about 0.3 PTB to about 1.0 PTB of at least one linear monocarboxylic acid or salt thereof having a carbon chain of 16 to 20 carbons, the linear monocarboxylic acid or salt thereof being saturated, unsaturated, or including mixtures thereof, and when (ii) is the at least one linear monocarboxylic acid, a weight ratio of (i) an amount of the at least one neutral lubricity additive divided by (ii) an amount of the at least one linear monocarboxylic acid is about 0.2 to about 5 and when (ii) is the at least one linear monocarboxylic acid salt, a weight ratio of (i) an amount of the at least one neutral lubricity additive divided by (ii) an amount of the at least one linear monocarboxylic acid salt is about 2 to about 30. ### Claim 7 (depends on 6) The fuel of claim 6, wherein a treat rate of the at lubricity additive mixture in the fuel is at least about 2 PTB. ### Claim 8 (depends on 6) The fuel of claim 6, wherein the hydrocarbyl substituent of the succinic anhydride is a linear or branched C16 to C18 group. ### Claim 9 (depends on 6) The fuel of claim 6, wherein the at least one linear monocarboxylic acid or salt thereof includes a linear carbon chain having 16 to 18 carbon atoms. ### Claim 10 (depends on 6) The fuel of claim 6, wherein the at least one linear monocarboxylic acid or salt thereof is selected from the group consisting of palmitic acid, margaric acid, stearic acid, arachidic acid, oleic acid, palmitoleic acid, linoleic acid, linolenic acid, eleosteric acid, arachidonic acid, linseed oil fatty acid, palm oil fatty acid, rapeseed oil fatty acid, soybean oil fatty acid, sunflower oil fatty acid, tall oil fatty acid, mixtures thereof, and salts thereof. ### Claim 11 (depends on 6) The fuel of claim 6, further comprising a detergent selected from the group consisting of (i) one or more Mannich reaction products formed by condensing a long chain aliphatic hydrocarbon-substituted phenol or cresol with an aldehyde, and an amine, (ii) long chain aliphatic hydrocarbons having an amine or a polyamine attached thereto, (iii) fuel-soluble nitrogen containing salts, amides, imides, succinimides, imidazolines, esters, and long chain aliphatic hydrocarbon-substituted dicarboxylic acids or their anhydrides or mixtures thereof, (iv) polyetheramines; (v) quaternary amines and salts thereof; and (vi) combinations thereof. ### Claim 12 A method of reducing wear in a gasoline engine comprising operating the gasoline engine with a fuel including a major amount of gasoline and a minor amount of a lubricity additive mixture, the fuel including (i) about 0.6 to about 10.8 PTB of at least one neutral lubricity additive prepared by reacting a hydrocarbyl-substituted succinic anhydride with ammonia wherein the hydrocarbyl substituent includes 8 to 20 carbons and (ii) about 0.3 PTB to about 1.0 PTB of at least one linear monocarboxylic acid or salt thereof having a carbon chain of 16 to 20 carbons, the linear monocarboxylic acid or salt thereof being saturated, unsaturated, or including mixtures thereof, and when (ii) is the at least one linear monocarboxylic acid, a weight ratio of (i) an amount of the at least one neutral lubricity additive divided by (ii) an amount of the at least one linear monocarboxylic acid is about 0.2 to about 5 and when (ii) is the at least one linear monocarboxylic acid salt, a weight ratio of (i) an amount of the at least one neutral lubricity additive divided by (ii) an amount of the at least one linear monocarboxylic acid salt is about 2 to about 30. ### Claim 13 (depends on 12) The method of claim 12, wherein a treat rate of the lubricity additive mixture in the fuel is at least about 2 PTB. ### Claim 14 (depends on 12) The method of claim 12, wherein the hydrocarbyl substituent of the succinic anhydride is a linear or branched C16 to C18 group. ### Claim 15 (depends on 12) The method of claim 12, wherein the linear monoacidic lubricity additive or salt thereof includes a linear carbon chain having 16 to 18 carbon atoms. ### Claim 16 (depends on 12) The method of claim 12, wherein the linear monoacidic lubricity additive or salt thereof is selected from the group consisting of palmitic acid, margaric acid, stearic acid, arachidic acid, oleic acid, palmitoleic acid, linoleic acid, linolenic acid, eleosteric acid, arachidonic acid, linseed oil fatty acid, palm oil fatty acid, rapeseed oil fatty acid, soybean oil fatty acid, sunflower oil fatty acid, tall oil fatty acid, mixtures thereof, and salts thereof. ### Claim 17 (depends on 12) The method of claim 12, wherein the reduced wear is one of about 15 to about 30 percent reduction in wear scar, about 25 to about 35 reduction in friction coefficient, or both as measured by the HFRR test of modified ASTM D6079. ### Claim 18 (depends on 1) The gasoline additive of claim 1, wherein the hydrocarbyl substituent of the hydrocarbyl-substituted succinic anhydride has 16 to 18 carbons and the at least one linear monocarboxylic acid or salt thereof is selected from oleic acid, TOFA, salts thereof, or combinations thereof. ### Claim 19 (depends on 6) The fuel of claim 6, wherein the hydrocarbyl substituent of the hydrocarbyl-substituted succinic anhydride has 16 to 18 carbons and the at least one linear monocarboxylic acid or salt thereof is selected from oleic acid, TOFA, salts thereof, or combinations thereof. ### Claim 20 (depends on 19) The fuel of claim 19, wherein the at least one linear monocarboxylic acid or salt thereof is an oleic acid salt and the fuel includes about 4 PTB to about 10 PTB of the combined neutral lubricity additive and the oleic acid salt. ### Claim 21 (depends on 12) The method of claim 12, wherein the hydrocarbyl substituent of the hydrocarbyl-substituted succinic anhydride has 16 to 18 carbons and the at least one linear monocarboxylic acid or salt thereof is selected from oleic acid, TOFA, salts thereof, or combinations thereof. ### Claim 22 (depends on 21) The method of claim 21, wherein the at least one linear monocarboxylic acid or salt thereof is an oleic acid salt and the fuel includes about 4 PTB to about 10 PTB of the combined neutral lubricity additive and the oleic acid salt. ### Claim 23 (depends on 1) The gasoline additive of claim 1, wherein the hydrocarbyl substituent of the succinic anhydride is a C14 to C18 hydrocarbyl group. ### Claim 24 (depends on 6) The fuel of claim 6, wherein the hydrocarbyl substituent of the succinic anhydride is a C14 to C18 hydrocarbyl group. ### Claim 25 (depends on 1) The gasoline additive of claim 1, wherein the weight ratio of (i) an amount of the at least one neutral lubricity additive divided by (ii) an amount of the at least one linear monocarboxylic acid salt is about 2.0 to about 20, and about 0.6 to about 10 PTB of (i) and about 0.3 to about 0.8 PTB of (ii) are used in a spark-ignitable fuel together. ### Claim 26 (depends on 6) The fuel of claim 6, wherein the fuel includes about 0.6 to about 10 PTB of (i) and about 0.3 to about 0.8 PTB of (ii), and the weight ratio of (i) an amount of the at least one neutral lubricity additive divided by (ii) an amount of the at least one linear monocarboxylic acid salt is about 2 to about 20. ### Claim 27 (depends on 12) The method of claim 12, wherein the fuel includes about 0.6 to about 10 PTB of (i) and about 0.3 to about 0.8 PTB of (ii), and the weight ratio of (i) an amount of the at least one neutral lubricity additive divided by (ii) an amount of the at least one linear monocarboxylic acid salt is about 2 to about 20.