Quaternary Ammonium Salt Or Amine Oxide Patents (Class 44/422)
  • Patent number: 10676685
    Abstract: The invention relates to the use of quaternized nitrogen compounds as a fuel and lubricant additive or kerosene additive, such as in particular as a detergent additive, for decreasing or preventing deposits in the injection systems of direct-injection diesel engines, in particular in common rail injection systems, for decreasing the fuel consumption of direct-injection diesel engines, in particular of diesel engines having common rail injection systems, and for minimizing the power loss in direct-injection diesel engines, in particular in diesel engines having common rail injection systems; the invention further relates to the use as an additive for petrol, in particular for operation of DISI engines.
    Type: Grant
    Filed: July 31, 2019
    Date of Patent: June 9, 2020
    Assignee: BASF SE
    Inventors: Markus Hansch, Harald Boehnke, Wolfgang Grabarse, Ludwig Voelkel, Maxim Peretolchin
  • Patent number: 10487281
    Abstract: A method for preventing biodeterioration of fuel. The method reduces the microbial growth in fuel by administering an antimicrobial peptide (or efflux pump inhibitor) to a fuel phase of the fuel, an aqueous phase of the fuel, or both, which disrupts the cellular membrane (or the efflux pumps thereof) of microbes comprising the growth.
    Type: Grant
    Filed: May 31, 2017
    Date of Patent: November 26, 2019
    Assignee: United States of America as represented by the Secretary of the Air Force
    Inventor: Oscar N. Ruiz
  • Patent number: 10479950
    Abstract: The invention relates to quaternary ammonium amide and/or ester salts and their use as additives, including their use in fuels, such as diesel fuel. The invention particularly relates to the use of quaternary ammonium amide and/or ester salts as detergents in diesel fuels.
    Type: Grant
    Filed: July 26, 2017
    Date of Patent: November 19, 2019
    Assignee: The Lubrizol Corporation
    Inventors: Paul R. Stevenson, James C. Ray, David J. Moreton, James H. Bush
  • Patent number: 10407634
    Abstract: The invention relates to the use of quaternized nitrogen compounds as a fuel and lubricant additive or kerosene additive, such as in particular as a detergent additive, for decreasing or preventing deposits in the injection systems of direct-injection diesel engines, in particular in common rail injection systems, for decreasing the fuel consumption of direct-injection diesel engines, in particular of diesel engines having common rail injection systems, and for minimizing the power loss in direct-injection diesel engines, in particular in diesel engines having common rail injection systems; the invention further relates to the use as an additive for petrol, in particular for operation of DISI engines.
    Type: Grant
    Filed: August 16, 2017
    Date of Patent: September 10, 2019
    Assignee: BASF SE
    Inventors: Markus Hansch, Harald Boehnke, Wolfgang Grabarse, Ludwig Voelkel, Maxim Peretolchin
  • Patent number: 9677020
    Abstract: A fuel additive composition, fuel composition, method of improving the injector performance of a fuel injected engine, method for preventing or cleaning up deposits in an engine or fuel system, method of reducing wear in a fuel system of an engine, and method of improving the demulsibility of a fuel composition. The fuel composition includes from about 5 to about 300 ppm by weight based on a total weight of the fuel composition of a hydrocarbyl soluble quaternary ammonium carboxylate derived from a quaternary ammonium carbonate and an organic acid.
    Type: Grant
    Filed: June 25, 2014
    Date of Patent: June 13, 2017
    Assignee: Afton Chemical Corporation
    Inventors: Xinggao Fang, Scott D. Schwab, Daniel Taylor
  • Patent number: 9506006
    Abstract: The present invention provides a composition and a concentrate, comprising: (a) a major amount of an oil of lubricating viscosity, (b) a quaternary ammonium salt of a hydrocarbyl-substituted acylating agent condensation product, and (c) an optional amount of a succinimide dispersant different from (b), and a use of the composition or concentrate for lubricating an engine. In a further embodiment, the invention provides the use of a quaternary ammonium salt of a hydrocarbyl-substituted acylating agent condensation product as a dispersant in a lubricating composition, and as a synergistic dispersant combination with a different succinimide dispersant.
    Type: Grant
    Filed: June 18, 2012
    Date of Patent: November 29, 2016
    Assignee: The Lubrizol Corporation
    Inventors: Joanne L. Jones, Dean Thetford, David J. Moreton, Matthew D. Gieselman
  • Patent number: 9458400
    Abstract: A fuel composition for a direct fuel injected gasoline engine comprising, a method for improving performance of fuel injectors and a method for cleaning fuel injectors for an internal combustion gasoline engine. The fuel composition includes a major amount of fuel and a minor, effective amount of a quaternary ammonium salt having a thermogravimetric analysis (TGA) weight loss of greater than 50 wt. % at 350° C. The amount of quaternary ammonium salt present in the fuel is sufficient to improve performance of the direct fuel injected engine having combusted the composition compared to the performance of such engine having combusted a fuel composition that does not contain the quaternary ammonium salt.
    Type: Grant
    Filed: May 6, 2014
    Date of Patent: October 4, 2016
    Assignee: Afton Chemical Corporation
    Inventor: Xinggao Fang
  • Patent number: 9394499
    Abstract: A method of removing deposits from a diesel engine, the method comprising combusting in the engine a diesel fuel composition comprising an engine cleaning additive, wherein the engine cleaning additive is the product of a Mannich reaction between: (a) an aldehyde; (b) ammonia, hydrazine or an amine; and (c) an optionally substituted phenol; wherein the or each substituent of the phenol component (c) has an average molecular weight of less than 400.
    Type: Grant
    Filed: February 13, 2015
    Date of Patent: July 19, 2016
    Assignee: Innospec Limited
    Inventor: Jacqueline Reid
  • Patent number: 9340742
    Abstract: The disclosure provide a sulfur-free and halogen-free synergistic additive concentrate for a fuel injected engine. The additive concentrate includes (a) an alkoxylated quaternary ammonium salt of the formula (R1)nN[(R2O)xH]m, wherein R1 contains from 1 to 25 carbon atoms, R2 contains from 1 to 4 carbon atoms, n and m are each integers from 1 to 3, provided n+m=4, and x is an integer of from 1 to 5; and (b) a material containing a hydrogen-bonding group other than an alkyl hydroxyl group selected from the group consisting of a hydrocarbyl acid; hydrocarbyl polyacid; hydrocarbyl substituted hydroxybenzene; hydrocarbyl substituted succinic diamide, acid/amide, diacid, diester, ester/acid, amide/ester, imide; aminotriazole, and mixtures thereof, wherein the hydrocarbyl substituent has a number average molecular weight of from about 100 to about 1500, and wherein a weight ratio of (a) to (b) in the additive ranges from about 1:5 to about 1:1.
    Type: Grant
    Filed: May 5, 2015
    Date of Patent: May 17, 2016
    Assignee: Afton Chemical Corporation
    Inventors: Xinggao Fang, Scott D. Schwab
  • Patent number: 9243199
    Abstract: A diesel fuel composition comprising a performance enhancing additive, wherein the performance enhancing additive is the product of a Mannich reaction between: (a) an aldehyde; (b) a polyamine; and (c) an optionally substituted phenol; wherein the polyamine component (b) includes the moiety R1R2NCHR3CHR4NR5R6 wherein each of R1, R2 R3, R4, R5 and R6 is independently selected from hydrogen, and an optionally substituted alkyl, alkenyl, alkynyl, aryl, alkylaryl or arylalkyl substituent.
    Type: Grant
    Filed: March 8, 2013
    Date of Patent: January 26, 2016
    Assignee: Innospec Limited
    Inventor: Jacqueline Reid
  • Patent number: 9085740
    Abstract: A method of removing deposits from a diesel engine, the method comprising combusting in the engine a diesel fuel composition comprising an engine cleaning additive, wherein the engine cleaning additive is the product of a Mannich reaction between: (a) an aldehyde; (b) ammonia, hydrazine or an amine; and (c) an optionally substituted phenol; wherein the or each substituent of the phenol component (c) has an average molecular weight of less than 400.
    Type: Grant
    Filed: February 25, 2010
    Date of Patent: July 21, 2015
    Assignee: Innospec Limited
    Inventor: Jacqueline Reid
  • Patent number: 9045709
    Abstract: Compositions that include a detergent composition and an active metal compound are described wherein the detergent composition includes a quaternary ammonium salt detergent and optionally an oxygen-containing detergent, and wherein the active metal compound is in the form of a colloidal dispersion, comprising an organic phase, particles of an iron compound in its amorphous form, and at least one amphiphilic agent. These compositions can be used in fuels to provide improved engine performance by, for example, reducing fuel injector fouling in the engine and/or by improving the regeneration of the engine's particulate exhaust trap.
    Type: Grant
    Filed: June 23, 2009
    Date of Patent: June 2, 2015
    Assignees: RHODIA OPERATIONS, THE LUBRIZOL CORPORATION
    Inventors: Virginie Harle, Michael Lallemand, David Moreton, Malcolm G J. Macduff, Magali Pudlarz
  • Patent number: 9006158
    Abstract: Polytetrahydrobenzoxazines and bistetrahydrobenzoxazines, obtainable by (A) reacting at least one diamine of the formula H2N-A-NH2 with a C1- to C12-aldehyde and a C1- to C8-alkanol at 20 to 80° C. with elimination and removal of water, (B) reacting the condensation product from (A) with a phenol which bears a long-chain substituent at 30 to 120° C., and optionally (C) heating the reaction product from (B) to 125 to 280° C. The resulting polytetrahydrobenzoxazines and bistetrahydrobenzoxazines are suitable as fuel or lubricant additives, especially as detergent additives for diesel fuels.
    Type: Grant
    Filed: December 7, 2011
    Date of Patent: April 14, 2015
    Assignee: BASF SE
    Inventors: Arno Lange, Harald Böhnke, Wolfgang Grabarse, Hannah Maria König, Markus Hansch, Ludwig Völkel, Ivette Garcia Castro
  • Publication number: 20150072910
    Abstract: A quaternary ammonium salt detergent made from the reaction product of the reaction of: (a) polyalkene-substituted amine having at least one tertiary amino group; and (b) a quaternizing agent suitable for converting the tertiary amino group to a quaternary nitrogen and the use of such quaternary ammonium salt detergents in a fuel composition to reduce intake valve deposits.
    Type: Application
    Filed: November 19, 2014
    Publication date: March 12, 2015
    Inventors: David J. Moreton, Paul R. Stevenson, Dean Thetford, Jonathan S. Vilardo
  • Patent number: 8974551
    Abstract: The disclosure provides a fuel additive concentrate, a method for cleaning fuel injectors, a method for restoring power to a diesel fuel injected engine, a fuel composition, and a method of operating a fuel injected diesel engine. The additive concentrate includes (a) a hydrocarbyl substituted quaternary ammonium internal salt and (b) a hydrocarbyl substituted dicarboxylic anhydride derivative, wherein the hydrocarbyl substituent has a number average molecular weight ranging from about 450 to about 1500. A weight ratio of (a) to (b) in the additive concentrate ranges from about 1:20 to about 2:1, and the additive concentrate is devoid of a reaction product of a hydrocarbyl substituted dicarboxylic acid, anhydride or ester and an amine compound of the formula wherein R2 is hydrogen or a hydrocarbyl group containing from 1 to 15 carbon atoms, and R3 is hydrogen or a hydrocarbyl group containing from 1 to 20 carbon atoms.
    Type: Grant
    Filed: February 19, 2014
    Date of Patent: March 10, 2015
    Assignee: Afton Chemical Corporation
    Inventors: Xinggao Fang, Scott D. Schwab
  • Patent number: 8961623
    Abstract: The invention relates to quaternary ammonium amide and/or ester salts and their use as additives, including their use in fuels, such as diesel fuel. The invention particularly relates to the use of quaternary ammonium amide and/or ester salts as detergents in diesel fuels.
    Type: Grant
    Filed: May 6, 2010
    Date of Patent: February 24, 2015
    Assignee: The Lubrizol Corporation
    Inventors: Paul R. Stevenson, James C. Ray, David J. Moreton, James H. Bush
  • Publication number: 20150034036
    Abstract: A gasoline composition comprising, as an additive, one or more quaternary ammonium salt(s) (i) formed by the reaction of a compound of formula (A): and a compound formed by the reaction of a hydrocarbyl-substituted acylating agent and an amine of formula (B1) or (B2): wherein R is an optionally substituted alkyl, alkenyl, aryl or alkylaryl group; R1 is an alkyl, aryl or alkylaryl group having up to 36 carbon atoms; R2 and R3 are the same or different alkyl groups having from 1 to 36 carbon atoms; X is an alkylene group having from 1 to 20 carbon atoms; n is from 0 to 20; m is from 1 to 5; and R4 is hydrogen or a C1 to C36 alkyl group.
    Type: Application
    Filed: October 20, 2014
    Publication date: February 5, 2015
    Applicant: INNOSPEC LIMITED
    Inventors: Vincent Burgess, Jacqueline Reid, Simon Mulqueen
  • Patent number: 8915977
    Abstract: A fuel soluble additive for a gasoline engine, a method for improving performance of fuel injectors and a method for cleaning fuel injectors for a gasoline engine. The fuel soluble additive includes a quaternary ammonium salt derived from an amido amine containing at least one tertiary amino group and an epoxide, in the presence of a proton donor selected from a carboxylic acid and an alkyl phenol. The amido amine is made in a reaction medium that is substantially devoid of an acylating agent.
    Type: Grant
    Filed: April 26, 2013
    Date of Patent: December 23, 2014
    Assignee: Afton Chemical Corporation
    Inventors: Xinggao Fang, Scott D. Schwab
  • Patent number: 8911516
    Abstract: A quaternized copolymer obtainable by: (A) copolymerization of straight-chain, branched or cyclic, ethylenically unsaturated C2 to C100 hydrocarbons, which may bear oxygen- or nitrogen-functional substituents which cannot be reacted with amines to give amides or imides or with alcohols to give esters, with ethylenically unsaturated C3- to C12-mono- or dicarboxylic acids or acid derivatives, which can be reacted with amines to give amides or imides or with alcohols to give esters, to give a copolymer with a number-average molecular weight of 500 to 20 000; (B) partial or full amidation or imidation or esterification of the carboxylic acid functions by reacting them with oligoamines having 2 to 6 nitrogen atoms or alcoholamines, each of which comprises primary or secondary nitrogen atom or a hydroxyl group and a quaternizable tertiary nitrogen atom; (C) partial or full quaternization of the tertiary nitrogen atom with a quaternizing agent.
    Type: Grant
    Filed: June 24, 2011
    Date of Patent: December 16, 2014
    Assignee: Basf SE
    Inventors: Wolfgang Grabarse, Hannah Maria Koenig, Christian Tock, Cornelia Roeger-Goepfert, Ludwig Voelkel, Harald Boehnke
  • Publication number: 20140345191
    Abstract: The invention relates to heating oils continuing quaternary ammonium salts, including succinimide, Mannich, polyalkylene substituted amine, quaternary ammonium salts. The invention also relates to the use of such salts in heating oil compositions and the use of such heating oil compositions in heating systems such as furnaces.
    Type: Application
    Filed: August 29, 2012
    Publication date: November 27, 2014
    Inventors: James H. Bush, Sarah J. Harrison, David C. Arters
  • Publication number: 20140331550
    Abstract: The present invention relates to novel acid-free quaternized nitrogen compounds, to the preparation thereof and to the use thereof as a fuel and lubricant additive, more particularly as a detergent additive, as a wax antisettling additive (WASA) or as an additive for reducing internal diesel injector deposits (IDID); to additive packages which comprise these compounds; and to fuels and lubricants thus additized. The present invention further relates to the use of these acid-free quaternized nitrogen compounds as a fuel additive for reducing or preventing deposits in the injection systems of direct-injection diesel engines, especially in common-rail injection systems, for reducing the fuel consumption of direct-injection diesel engines, especially of diesel engines with common-rail injection systems, and for minimizing power loss in direct-injection diesel engines, especially in diesel engines with common-rail injection systems.
    Type: Application
    Filed: July 22, 2014
    Publication date: November 13, 2014
    Applicant: BASF SE
    Inventors: Wolfgang GRABARSE, Harald Boehnke, Christian Tock, Cornelia Roeger-Goepfert, Ludwig Voelkel
  • Publication number: 20140318486
    Abstract: A fuel soluble additive for a gasoline engine, a method for improving performance of fuel injectors and a method for cleaning fuel injectors for a gasoline engine. The fuel soluble additive includes a quaternary ammonium salt derived from an amido amine containing at least one tertiary amino group and an epoxide, in the presence of a proton donor selected from a carboxylic acid and an alkyl phenol. The amido amine is made in a reaction medium that is substantially devoid of an acylating agent.
    Type: Application
    Filed: April 26, 2013
    Publication date: October 30, 2014
    Applicant: Afton Chemical Corporation
    Inventors: Xinggao FANG, Scott D. SCHWAB
  • Publication number: 20140318487
    Abstract: A fuel soluble additive for a diesel engine, a method for improving performance of fuel injectors and a method for cleaning fuel injectors for a diesel engine. The fuel soluble additive includes a quaternary ammonium salt derived from an amido amine containing at least one tertiary amino group and an epoxide, in the presence of a proton donor selected from a carboxylic acid and an alkyl phenol. The amido amine is made in a reaction medium that is substantially devoid of an acylating agent.
    Type: Application
    Filed: April 26, 2013
    Publication date: October 30, 2014
    Applicant: Afton Chemical Corporation
    Inventors: Xinggao FANG, Scott D. SCHWAB
  • Patent number: 8863700
    Abstract: In accordance with the disclosure, exemplary embodiments provide a fuel additive concentrate, a method for cleaning fuel injectors, a method for restoring power to a diesel fuel injected engine, a fuel composition, and a method of operating a fuel injected diesel engine. The additive concentrate includes (a) a hydrocarbyl substituted quaternary ammonium internal salt; and (b) a reaction product of (i) a hydrocarbyl substituted dicarboxylic acid, anhydride, or ester and (ii) an amine compound or salt thereof of the formula wherein R is selected from hydrogen and a hydrocarbyl group containing from about 1 to about 15 carbon atoms, and R1 is selected from hydrogen and a hydrocarbyl group containing from about 1 to about 20 carbon atoms. The reaction product (b) on average has less than 2 amino-triazole groups per molecule. A weight ratio of (a) to (b) in the additive concentrate ranges from about 10:1 to about 1:10.
    Type: Grant
    Filed: November 1, 2012
    Date of Patent: October 21, 2014
    Assignee: Afton Chemical Corporation
    Inventors: Xinggao Fang, Scott D. Schwab
  • Patent number: 8821594
    Abstract: Disclosed herein is a fuel oil composition with enhanced conductivity. The oil composition comprises a Petroleum Based Component and a combination of Lubricity and Conductivity additives. In one aspect, additional additives can be added such as: (a) low temperature operability/cold flow additives, (b) corrosion inhibitors, (c) cetane improvers, (d) detergents, and (e) dyes and markers (f) anti-icing additives, (g) demulsifiers/anti haze additives, (h) antioxidants, (i) metal deactivators, (j) biocides, and (k) thermal stabilizers. Further, the present disclosure describes a method of using such composition is described.
    Type: Grant
    Filed: September 27, 2006
    Date of Patent: September 2, 2014
    Assignee: Innospec Fuel Specialities LLC
    Inventors: Cenk R. Burgazli, Cyrus P. Henry, Jr.
  • Publication number: 20140238328
    Abstract: A fuel composition for a direct fuel injected gasoline engine comprising, a method for improving performance of fuel injectors and a method for cleaning fuel injectors for an internal combustion gasoline engine. The fuel composition includes a major amount of fuel and a minor, effective amount of a quaternary ammonium salt having a thermogravimetric analysis (TGA) weight loss of greater than 50 wt. % at 350° C. The amount of quaternary ammonium salt present in the fuel is sufficient to improve performance of the direct fuel injected engine having combusted the composition compared to the performance of such engine having combusted a fuel composition that does not contain the quaternary ammonium salt.
    Type: Application
    Filed: May 6, 2014
    Publication date: August 28, 2014
    Applicant: Afton Chemical Corporation
    Inventor: Xinggao FANG
  • Patent number: 8771625
    Abstract: A method is described for reducing nitrogen oxides in the exhaust gas flow of combustion engines, especially a motor vehicle internal combustion engine, wherein an air/fuel mixture in the combustion chamber of the combustion engine is combusted in the presence of a fuel additive and, in the process, the fuel additive decomposes and the exhaust gas flow is guided through at least one catalyst arranged downstream of the combustion chamber. This method is characterized in that a fuel additive is used, which decomposes in the combustion chamber releasing ammonia and the exhaust gas flow containing ammonia is guided through at least one SCR catalyst arranged downstream of the combustion chamber to reduce the concentration of the nitrogen oxides contained therein.
    Type: Grant
    Filed: September 3, 2009
    Date of Patent: July 8, 2014
    Assignee: MAN Truck & Bus AG
    Inventors: Doering Andreas, Dieter Rothe
  • Publication number: 20140174390
    Abstract: A diesel fuel composition comprising a quaternary ammonium salt additive which additive is formed by the reaction of (1) a quaternising agent and (2) a compound formed by the reaction of a hydrocarbyl-substituted acylating agent and at least 1.4 molar equivalents of an amine of formula (B1) or (B2), wherein R2 and R3 are the same or different alkyl, alkenyl or aryl groups having from 1 to 22 carbon atoms; X is a bond or alkylene group having from 1 to 20 carbon atoms; n is from 0 to 20; m is from 1 to 5; and R4 is hydrogen or a C1 to C22 alkyl group.
    Type: Application
    Filed: August 2, 2012
    Publication date: June 26, 2014
    Inventors: Jacqueline Reid, Stephen Leonard Cook
  • Patent number: 8690970
    Abstract: A fuel composition for a fuel injected internal combustion engine, a method for improving performance of fuel injectors and a method for cleaning fuel injectors for a fuel-injected internal combustion engine. The fuel composition includes a major amount of fuel and a minor, effective amount of a quaternary ammonium salt of a hydrocarbyl amine and a hydrocarbyl-substituted alkyl-hydroxybenzoate. The amount of quaternary ammonium salt present in the fuel is sufficient to improve performance of the fuel injected internal combustion engine having combusted the composition compared to the performance of such engine having combusted a fuel composition that does not contain the quaternary ammonium salt. The hydrocarbyl-substituted alkyl-hydroxybenzoate contains one or more hydrocarbyl substituents providing a total of at least 8 up to about 200 carbon atoms, provided the one or more hydrocarbyl substituents do not contain sulfur, oxygen, or nitrogen atoms.
    Type: Grant
    Filed: February 24, 2012
    Date of Patent: April 8, 2014
    Assignee: Afton Chemical Corporation
    Inventor: Xinggao Fang
  • Patent number: 8679203
    Abstract: Hydrogen sulfide and mercaptans in hydrocarbons, gas mixtures of hydrocarbons and the like may be scavenged therefrom by being brought into intimate contact with a mercaptan scavenger formulation of quaternary ammonium alkoxide or hydroxide in the presence of a high oxidative state metal such as cobalt, iron, chromium and/or nickel. The high oxidative state metal, being an oxidizer, acts as a catalyst when combined with the quaternary ethoxide or hydroxide for improved mercaptan scavenging performance.
    Type: Grant
    Filed: November 22, 2010
    Date of Patent: March 25, 2014
    Assignee: Baker Hughes Incorporated
    Inventors: Timothy J. O'Brien, Jerry J. Weers
  • Publication number: 20130296210
    Abstract: The present invention relates to the use of quaternized alkylamine nitrogen compounds as a fuel additive and lubricant additive, such as, more particularly, as a detergent additive; for reduction or prevention of deposits in the injection systems of direct injection diesel engines, especially in common rail injection systems, for reduction of the fuel consumption of direct injection diesel engines, especially of diesel engines with common rail injection systems, and for minimization of power loss in direct injection diesel engines, especially in diesel engines with common rail injection systems; and as an additive for gasoline fuels, especially for operation of DISI engines.
    Type: Application
    Filed: December 12, 2012
    Publication date: November 7, 2013
    Inventors: Markus HANSCH, Harald BOEHNKE, Ludwig VOELKEL, Wolfgang GRABARSE, Jan STRITTMATTER
  • Patent number: 8460404
    Abstract: The invention provides a composition comprising a dispersion comprising (a) an inorganic metal compound, (b) a quaternary salt surfactant and (c) an organic medium, wherein the metal compounds are uniformly dispersed in the organic medium. The invention also provides fuel compositions comprising said dispersion and methods of operating internal combustion engines and open flame burners utilizing said dispersion.
    Type: Grant
    Filed: May 11, 2009
    Date of Patent: June 11, 2013
    Assignee: The Lubrizol Corporation
    Inventor: Claire L. Hollingshurst
  • Publication number: 20130125452
    Abstract: An amine mixture includes a polyisobuteneamine and an aliphatic amine. The amine mixture is obtained by reductive amination of a mixture with ammonia or an amine HNR2R3. The mixture can be a mixture of the oxo process product formed in the hydroformylation of polybutene or polyisobutene and an alkanol R4—OH. The mixture can also be a mixture of the epoxide formed in the epoxidation of polybutene or polyisobutene and an alkanol R4—OH. Or, instead, the mixture can be a mixture of the nitro compound formed in the reaction of polybutene or polyisobutene with nitrogen oxides and an alkanol R4—OH. The amine mixture is suitable for cleaning and keeping clean intake valves and injection nozzles in gasoline engines.
    Type: Application
    Filed: November 19, 2012
    Publication date: May 23, 2013
    Inventors: Harald SCHWAHN, Marc Walter
  • Publication number: 20130118062
    Abstract: A fuel composition for a direct fuel injected diesel engine, a method for improving performance of fuel injectors and a method for cleaning fuel injectors for a diesel engine. The fuel composition includes a major amount of fuel and a minor, effective amount of a quaternary ammonium salt having a thermogravimetric analysis (TGA) weight loss of greater than 50 wt. % at 350° C. The amount of quaternary ammonium salt present in the fuel is sufficient to improve performance of the direct fuel injected diesel engine having combusted the composition compared to the performance of such engine having combusted a fuel composition that does not contain the quaternary ammonium salt.
    Type: Application
    Filed: November 11, 2011
    Publication date: May 16, 2013
    Applicant: AFTON CHEMICAL CORPORATION
    Inventors: Xinggao FANG, Julienne M. GALANTE-FOX
  • Publication number: 20130104826
    Abstract: A gasoline composition comprising, as an additive, one or more quaternary ammonium salt(s) (i) formed by the reaction of a compound of formula (A): and a compound formed by the reaction of a hydrocarbyl-substituted acylating agent and an amine of formula (B1) or (B2): wherein R is an optionally substituted alkyl, alkenyl, aryl or alkylaryl group; R1 is an alkyl, aryl or alkylaryl group having up to 36 carbon atoms; R2 and R3 are the same or different alkyl groups having from 1 to 36 carbon atoms; X is an alkylene group having from 1 to 20 carbon atoms; n is from 0 to 20; m is from 1 to 5; and R4 is hydrogen or a C1 to C36 alkyl group.
    Type: Application
    Filed: May 10, 2011
    Publication date: May 2, 2013
    Applicant: INNOSPEC LIMITED
    Inventors: Vince Burgess, Jacqueline Reid, Simon Mulqueen
  • Publication number: 20120267481
    Abstract: The formation in a liquid hydrocarbon fuel of ice particles having a weight average particle size greater than 1 ?m when said liquid hydrocarbon fuel is cooled to temperatures in the range of from 0 to ?50° C. can be reduced or eliminated by use of at least one surfactant that is capable of dispersing water in said liquid hydrocarbon fuel to provide a stable clear water-in-oil microemulsion wherein the droplet size of the dispersed water phase is no greater than 0.25 ?m.
    Type: Application
    Filed: October 13, 2010
    Publication date: October 25, 2012
    Applicant: PALOX OFFSHORE S.A.L.
    Inventor: David William Martin
  • Publication number: 20120149617
    Abstract: Polytetrahydrobenzoxazines and bistetrahydrobenzoxazines, obtainable by (A) reacting at least one diamine of the formula H2N-A-NH2 with a C1- to C12-aldehyde and a C1- to C8-alkanol at 20 to 80° C. with elimination and removal of water, (B) reacting the condensation product from (A) with a phenol which bears a long-chain substituent at 30 to 120° C., and optionally (C) heating the reaction product from (B) to 125 to 280° C. The resulting polytetrahydrobenzoxazines and bistetrahydrobenzoxazines are suitable as fuel or lubricant additives, especially as detergent additives for diesel fuels.
    Type: Application
    Filed: December 7, 2011
    Publication date: June 14, 2012
    Applicant: BASF SE
    Inventors: Arno LANGE, Harald Böhnke, Wolfgang Grabarse, Hannah Maria König, Markus Hansch, Ludwig Völkel, Ivette Garcia Castro
  • Patent number: 8147569
    Abstract: A quaternary ammonium salt detergent made from the reaction product of the reaction of: (a) a hydrocarbyl substituted acylating agent and a compound having an oxygen or nitrogen atom capable of condensing with said acylating agent and further having a tertiary amino group; and (b) a quaternizing agent suitable for converting the tertiary amino group to a quaternary nitrogen and the use of such quaternary ammonium salt detergents in a fuel composition to reduce intake valve deposits.
    Type: Grant
    Filed: April 13, 2011
    Date of Patent: April 3, 2012
    Assignee: The Lubrizol Corporation
    Inventors: William R. S. Barton, Mark C. Davies, David J. Moreton
  • Patent number: 8083814
    Abstract: A quaternary ammonium salt detergent made from the reaction product of the reaction of: (a) Mannich reaction product having a tertiary amino group, said Mannich reaction product being prepared from the reaction of a hydrocarbyl-substituted phenol, an aldehyde, and amine; and (b) a quaternizing agent suitable for converting the tertiary amino group to a quaternary nitrogen and the use of such quaternary ammonium salt detergents in a fuel composition to reduce intake valve deposits.
    Type: Grant
    Filed: January 31, 2011
    Date of Patent: December 27, 2011
    Assignee: The Lubrizol Corporation
    Inventors: Paul R. Stevenson, Dean Thetford, Jonathan S. Vilardo
  • Publication number: 20110219674
    Abstract: The present invention relates to fuel additives, fuel additive compositions and fuel compositions, as well as a method for fueling an internal combustion engine, providing reduced metal pick-up by fuels where the compositions of the present invention contain a hydrocarbon substituted with at least two carboxy functionalities in the form of acids or at least one carboxy functionality in the form of an anhydride.
    Type: Application
    Filed: October 1, 2009
    Publication date: September 15, 2011
    Applicant: THE LUBRIZOL CORPORATION
    Inventors: Robert H. Barbour, Paul R. Stevenson, Emma Fahey
  • Publication number: 20110185626
    Abstract: A quaternary ammonium salt detergent made from the reaction product of the reaction of: (a) a hydrocarbyl substituted acylating agent and a compound having an oxygen or nitrogen atom capable of condensing with said acylating agent and further having a tertiary amino group; and (b) a quaternizing agent suitable for converting the tertiary amino group to a quaternary nitrogen and the use of such quaternary ammonium salt detergents in a fuel composition to reduce intake valve deposits.
    Type: Application
    Filed: April 13, 2011
    Publication date: August 4, 2011
    Applicant: THE LUBRIZOL CORPORATION
    Inventors: William Barton, Mark C. Davies, David J. Moreton, Paul R. Stevenson, Dean Thetford
  • Publication number: 20110143981
    Abstract: A quaternary ammonium salt detergent made from the reaction product of the reaction of: (a) a hydrocarbyl substituted acylating agent and a compound having an oxygen or nitrogen atom capable of condensing with said acylating agent and further having a tertiary amino group; and (b) a quaternizing agent suitable for converting the tertiary amino group to a quaternary nitrogen and the use of such quaternary ammonium salt detergents in a fuel composition to reduce intake valve deposits.
    Type: Application
    Filed: February 2, 2011
    Publication date: June 16, 2011
    Applicant: The Lubrizol Corporation
    Inventors: William Barton, Mark C. Davies, David J. Moreton, Paul R. Stevenson, Dean Thetford
  • Publication number: 20110130317
    Abstract: A quaternary ammonium salt detergent made from the reaction product of the reaction of: (a) Mannich reaction product having a tertiary amino group, said Mannich reaction product being prepared from the reaction of a hydrocarbyl-substituted phenol, an aldehyde, and amine; and (b) a quaternizing agent suitable for converting the tertiary amino group to a quaternary nitrogen and the use of such quaternary ammonium salt detergents in a fuel composition to reduce intake valve deposits.
    Type: Application
    Filed: January 31, 2011
    Publication date: June 2, 2011
    Applicant: THE LUBRIZOL CORPORATION
    Inventors: Paul R. Stevenson, Dean Thetford, Jonathan S. Vilardo
  • Patent number: 7951211
    Abstract: A quaternary ammonium salt detergent made from the reaction product of the reaction of: (a) a hydrocarbyl substituted acylating agent and a compound having an oxygen or nitrogen atom capable of condensing with said acylating agent and further having a tertiary amino group; and (b) a quaternizing agent suitable for converting the tertiary amino group to a quaternary nitrogen and the use of such quaternary ammonium salt detergents in a fuel composition to reduce intake valve deposits.
    Type: Grant
    Filed: June 13, 2006
    Date of Patent: May 31, 2011
    Assignee: The Lubrizol Corporation
    Inventors: William Barton, Mark C. Davies, David J. Moreton, Paul R. Stevenson, Dean Thetford
  • Patent number: 7947093
    Abstract: A quaternary ammonium salt detergent made from the reaction product of the reaction of: (a) a hydrocarbyl substituted acylating agent and a compound having an oxygen or nitrogen atom capable of condensing with said acylating agent and further having a tertiary amino group; and (b) a quaternizing agent suitable for converting the tertiary amino group to a quaternary nitrogen and the use of such quaternary ammonium salt detergents in a fuel composition to reduce intake valve deposits.
    Type: Grant
    Filed: June 24, 2010
    Date of Patent: May 24, 2011
    Assignee: The Lubrizol Corporation
    Inventors: William Barton, Mark C. Davies, David J. Moreton, Paul R. Stevenson, Dean Thetford
  • Publication number: 20110113680
    Abstract: Hydrogen sulfide and mercaptans in hydrocarbons, gas mixtures of hydrocarbons and the like may be scavenged therefrom by being brought into intimate contact with a mercaptan scavenger formulation of quaternary ammonium alkoxide or hydroxide in the presence of a high oxidative state metal such as cobalt, iron, chromium and/or nickel. The high oxidative state metal, being an oxidizer, acts as a catalyst when combined with the quaternary ethoxide or hydroxide for improved mercaptan scavenging performance.
    Type: Application
    Filed: November 22, 2010
    Publication date: May 19, 2011
    Applicant: Baker Hughes Incorporated
    Inventors: Timothy J. O'Brien, Jerry J. Weers
  • Patent number: 7918905
    Abstract: The addition of strong neutralizing amines to react with free fatty acid in biodiesel fuels that may be left from some synthesis routes can lower the total acid number (TAN) of the biodiesel fuel. Surprisingly, the strong neutralizing amines do not interfere with the biodiesel fuel itself which may be primarily fatty acid methyl esters. These strong neutralizing amines may also improve the oxidative stability of biodiesel fuels.
    Type: Grant
    Filed: May 17, 2007
    Date of Patent: April 5, 2011
    Assignee: Baker Hughes Incorporated
    Inventors: Lawrence N. Kremer, Jerry J. Weers, Jennifer D. Draper
  • Publication number: 20110048354
    Abstract: The invention provides a composition comprising a dispersion comprising (a) an inorganic metal compound, (b) a quaternary salt surfactant and (c) an organic medium, wherein the metal compounds are uniformly dispersed in the organic medium. The invention also provides fuel compositions comprising said dispersion and methods of operating internal combustion engines and open flame burners utilizing said dispersion.
    Type: Application
    Filed: May 11, 2009
    Publication date: March 3, 2011
    Applicant: THE LUBRIZOL CORPORATION
    Inventor: Claire L. Hollingshurst
  • Publication number: 20100257779
    Abstract: A quaternary ammonium salt detergent made from the reaction product of the reaction of: (a) a hydrocarbyl substituted acylating agent and a compound having an oxygen or nitrogen atom capable of condensing with said acylating agent and further having a tertiary amino group; and (b) a quaternizing agent suitable for converting the tertiary amino group to a quaternary nitrogen and the use of such quaternary ammonium salt detergents in a fuel composition to reduce intake valve deposits.
    Type: Application
    Filed: June 24, 2010
    Publication date: October 14, 2010
    Applicant: The Lubrizol Corporation
    Inventors: William Barton, Mark C. Davies, David J. Moreton, Paul R. Stevenson, Dean Thetford
  • Patent number: 7799101
    Abstract: A stabilized lubricant composition is disclosed that comprises lubricating oil and a mixture of (a) at least one organophosphite compound and (b) at least one aromatic secondary amine or one substituted phenol or mixtures thereof. The compositions have been found to be highly resistant to oxidation under demanding service conditions.
    Type: Grant
    Filed: September 29, 2004
    Date of Patent: September 21, 2010
    Assignee: Chemtura Corporation
    Inventors: Jun Dong, Cyril A. Migdal