Nitrogen Attached Indirectly To The -c(=o)o- Group By Nonionic Bonding Patents (Class 44/399)
  • Patent number: 11208603
    Abstract: Fuel compositions comprising at least 10 ppm by weight of a succinic ester acid amine salt or a succinamide acid amine salt (both “amine salt(s)”). The amine salt is the product of (a) and (b), wherein: (a) is an amine with (i) at least one tertiary nitrogen and (ii) at least one hydroxy alkyl functional group and/or at least one secondary amine functionality; and (b) is a hydrocarbyl-substituted succinic acid/or anhydride. The molar ratio of (a) to (b) may range from 3:1 to 1:3. The fuel composition may comprise gasoline, oxygenate, or mixtures thereof. Methods and uses for reducing carbonaceous deposits in an engine comprising operating the engine using the fuel composition having an amine salt therein.
    Type: Grant
    Filed: March 5, 2018
    Date of Patent: December 28, 2021
    Assignee: The Lubrizol Corporation
    Inventors: Stuart L. Bartley, Matthew Nyce
  • Patent number: 10358615
    Abstract: Disclosed herein is a method comprising the steps of (a) providing a fuel additive concentrate comprising (i) from about 5 to about 50 wt. %, based on the total weight of the fuel additive concentrate, of one or more fatty acid sorbitan esters, and (ii) about 10 to about 95 wt. %, based on the total weight of the fuel additive concentrate, of a fuel carrier fluid, and (b) storing the fuel additive concentrate at a low temperature environment. Also disclosed is a method operating an internal combustion engine with a fuel composition comprising (a) a major amount of a fuel, and (b) a minor amount of one or more fatty acid sorbitan esters in a low temperature environment.
    Type: Grant
    Filed: September 30, 2016
    Date of Patent: July 23, 2019
    Assignee: Chevron U.S.A. Inc.
    Inventor: Theresa Liang Gunawan
  • 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
  • Publication number: 20140157657
    Abstract: A diesel fuel composition comprising a first additive (i) comprising a quaternary ammonium salt and a second additive (ii) comprising a Mannich reaction product; wherein the quaternary ammonium salt additive (i) is formed by the reaction of a compound of formula (A): R O O R1 10 (A) and a compound formed by the reaction of a hydrocarbyl-substituted acylating agent and an amine of formula (B1) or (B2): 15 N X R3 R2 NHR4 N X R3 R2 [O(CH2)m]nOH (B1) (B2) wherein R is an optionally substituted alkyl, alkenyl, aryl or alkylaryl group; R1 is a C1 to C22 alkyl, aryl or alkylaryl group; 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 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; and wherein the Mannich reaction product additive (ii) is the product of a Mannich reaction between: (d) an aldehyde; (e) an amine; and 25 (f) a substituted phenol; wherein the ph
    Type: Application
    Filed: August 2, 2012
    Publication date: June 12, 2014
    Inventor: Jacqueline Reid
  • 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: 8668749
    Abstract: A diesel fuel additive composition, a fuel containing the fuel additive, a method for improving diesel engine performance using the additive. The diesel fuel additive includes a reaction product of (a) a hydrocarbyl-substituted acylating agent and (b) a reactant selected from the group consisting of a nitrogen-containing compound, a hydroxyl-containing compound, and water that provides a reaction product selected from the group consisting (1) a mono-amide/mono-acid or metal free mono-acid salt thereof, (2) a diacid or metal free diacid salt thereof, and (3) mono-ester/mono-acid or metal free mono-acid salt thereof. The reaction product includes at least about 10 molar percent acid groups based on total moles of the reaction product.
    Type: Grant
    Filed: November 3, 2010
    Date of Patent: March 11, 2014
    Assignee: Afton Chemical Corporation
    Inventor: Xinggao Fang
  • Publication number: 20130298451
    Abstract: The present invention is directed to Mannich condensation product sequestering agents or mixtures of Mannich condensation product sequestering agents for use in fuels and lubricating oils. The present invention is also directed to a process for preparing the Mannich condensation product sequestering agents. The present invention is also directed to a product formed by combining, under reaction conditions, a polyisobutyl-substituted hydroxyaromatic compound, an aldehyde, an amino acid or ester thereof, and an alkali metal base to form the Mannich condensation product sequestering agent. The present invention is also directed to a lubricating oil composition, a lubricating oil concentrate, a fuel composition, and a fuel concentrate having the Mannich condensation product sequestering agents of the present invention.
    Type: Application
    Filed: April 12, 2013
    Publication date: November 14, 2013
    Applicant: Chevron Oronite Company LLC
    Inventors: James J. Harrison, Kenneth D. Nelson
  • Patent number: 8187345
    Abstract: Provided is a mixture containing: (a) a polar oil-soluble nitrogen compounds which is capable of sufficiently dispersing paraffin crystals precipitated out under cold conditions in a fuel and is a reaction product formed from reacting a poly(C2- to C20-carboxylic acid), which has at least one tertiary amino group, with a primary or secondary amine; (b) an oil-soluble acid amide reaction product formed from reacting a polyamide, which has from 2 to 1000 carbon atoms, with a C8- to C30-fatty acid or fatty acid-like compound, which has a free carboxyl group; and (c) an oil-soluble reaction product formed from reacting an ?,?-dicarboxylic acid, which has from 4 to 300 carbon atoms, or a derivatives thereof, with a primary alkylamine, wherein the sum of components (a) to (c) constitute 100 wt. % of the mixture. The mixture is suitable as a paraffin dispersant in fuels, especially those having a biodiesel content.
    Type: Grant
    Filed: June 12, 2007
    Date of Patent: May 29, 2012
    Assignee: BASF SE
    Inventors: Ansgar Eisenbeis, Irene Troetsch-Schaller, Ulrich Annen
  • Patent number: 8075804
    Abstract: Compositions containing phenolic antioxidant solutions are provided. The invention further provides methods of making and using such compositions as well as compositions that contain both biodiesel and at least one antioxidant concentrate solutions and blended fuel compositions containing biodiesel blended with other fuels.
    Type: Grant
    Filed: January 25, 2007
    Date of Patent: December 13, 2011
    Assignee: Eastman Chemical Company
    Inventors: Thomas Edward Carter, Joy Lynn Laningham, Phillip Montgomery Hudnall, Sharon Metcalf Cline
  • Publication number: 20100031559
    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: Application
    Filed: September 27, 2006
    Publication date: February 11, 2010
    Inventors: Cenk R. Burgazli, Cyrus P. Henry, JR.
  • Publication number: 20100006049
    Abstract: A composition and method of improving the fuel economy of hydrocarbon fuel-powdered internal combustion engines. The composition contains a propoxylated and/or butoxylated reaction product of (a) at least one fatty acid, fatty acid ester, or mixture thereof and (b) a dialkanolamime. The composition is added to a hydrocarbon fuel in an amount of about 5 to about 2,000 ppm, based on the weight of the hydrocarbon fuel, to reduce friction within the engine and achieve an enhanced fuel economy.
    Type: Application
    Filed: July 9, 2009
    Publication date: January 14, 2010
    Applicant: BASF CORPORATION
    Inventors: Alfred K. Jung, Ludwig Voelkel, Stefano Crema, Andrea Misske
  • Patent number: 7491249
    Abstract: An improved fuel additive formulation, method of use, and method of producing the fuel formulation are described. The improved fuel additive of the present invention comprises a mixture of nitroparaffins (comprising nitromethane, nitroethane, and nitropropane), and a combination of modified commercially available ester oil and/or a solubilizing agent, and/or toluene. The ratio of ester oil and/or solubilizing agent and/or toluence to nitroparaffin is preferably less than 20 volume percent, with nitroparaffins comprising the balance of the additive. A method of preparing and using the additive formulation is also provided.
    Type: Grant
    Filed: July 27, 2001
    Date of Patent: February 17, 2009
    Assignee: Mazoil Technologies, Ltd.
    Inventors: Arthur R. Foote, Michael Lakin, Peter Wachtel, Albert Schrage
  • Patent number: 6786940
    Abstract: The mixture contains (a) from 5 to 95% by weight of at least one reaction product of a poly(C2-20-carboxylic acid) having at least one tertiary amino group with secondary amines and (b) from 5 to 95% by weight of at least one reaction product of maleic anhydride and a primary alkylamine.
    Type: Grant
    Filed: April 23, 2001
    Date of Patent: September 7, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Wenderoth, Dieter Hermeling
  • Publication number: 20040148849
    Abstract: An improved fuel additive formulation, method of use, and method of producing the fuel formulation are described. The improved fuel additive of the present invention comprises a mixture of nitroparaffins (comprising nitromethane, nitroethane, and nitropropane), and a combination of modified commercially available ester oil and/or a solubilizing agent, and/or toluene. The ratio of ester oil and/or solubilizing agent and/or toluence to nitroparaffin is preferably less than 20 volume percent, with nitroparaffins comprising the balance of the additive. A method of preparing and using the additive formulation is also provided.
    Type: Application
    Filed: May 27, 2003
    Publication date: August 5, 2004
    Inventors: Arthur R. Foote, Michael Lakin, Peter Wachtel, Albert Schrage
  • Patent number: 6592639
    Abstract: The invention concerns a fuel for diesel engines, with a sulphur content of less than 500 ppm containing in a major proportion at least one average distillate from a straight-run distilling cup of crude oil, with temperature ranges between 150 and 400° C. and in a minor proportion a lubricating additive containing monocarboxylic and polycyclic acids.
    Type: Grant
    Filed: March 17, 1999
    Date of Patent: July 15, 2003
    Assignee: Elf Antar France
    Inventors: Christian Bernasconi, Laurent Germanaud, Jean-Michel Laupie, Paul Maldonado
  • Patent number: 6475251
    Abstract: A method for controlling engine deposits in a direct injection spark ignition gasoline engine which comprises operating the engine with a fuel composition comprising a major amount of hydrocarbons boiling in the gasoline range and an effective deposit-controlling amount of a fuel additive composition comprising: (a) an aromatic ester compound of the formula: or a fuel soluble salt thereof, wherein R is hydroxy, nitro or —(CH2)x—NR5R6, wherein R5 and R6 are independently hydrogen or lower alkyl having 1 to 6 carbon atoms and x is 0 or 1; R1 is hydrogen, hydroxy, nitro or —NR7R8, wherein R7 and R8 are independently hydrogen or lower alkyl having 1 to 6 carbon atoms; R2 and R3 are independently hydrogen or lower alkyl having 1 to 6 carbon atoms; and R4 is a polyalkyl group having an average molecular weight in the range of about 450 to 5,000; and (b) a poly(oxyalkylene) amine having at least one basic nitrogen atom and a sufficient number of oxyalkylene units to render the p
    Type: Grant
    Filed: February 28, 2001
    Date of Patent: November 5, 2002
    Assignee: Chevron Oronite Company LLC
    Inventor: Majid R. Ahmadi
  • Patent number: 6361573
    Abstract: Reaction products of i) a hydroxyl-group containing compound; ii) an amine-group containing compound, wherein component ii) is different from component i); and iii) a hydrocarbyl-substituted succinic acylating agent provide improved detergency as well as improved lubricity to hydrocarbon fuels. Compositions comprising a hydrocarbon fuel and the reaction products are also disclosed.
    Type: Grant
    Filed: August 31, 1999
    Date of Patent: March 26, 2002
    Assignee: Ethyl Corporation
    Inventor: Timothy J. Henly
  • Patent number: 6277158
    Abstract: An additive concentrate for use in fuels, especially in gasoline for internal combustion engines, comprising (a) 0.2 to 10 wt. % ashless friction modifier which is liquid at room temperature and pressure selected from (i) n-butylamine oleate or derivatives thereof, (ii) a substance comprising tall oil fatty acid or derivatives thereof, and (iii) mixtures of (i) and (ii); (b) 10 to 80 wt. % deposit inhibitor, and (c) carrier fluid. The particular selection of friction modifier (a) enables a stable additive concentrate to be formulated without the need for additional solubilising agent for the friction modifier, while containing sufficient friction modifier to achieve a significant benefit in fri loss, when incorporated in gasoline used to fuel an internal combustion engine, and hence an improvement in fuel economy.
    Type: Grant
    Filed: July 18, 2000
    Date of Patent: August 21, 2001
    Assignee: Exxon Research and Engineering Company
    Inventor: Gail McLean
  • Patent number: 6187063
    Abstract: An aqueous macroemulsion to be used in place of petroleum residuum-based fuel oils such as No. 4, No. 5, and No. 6 fuel oils, as well as the vacuum residuum from the fraction distillation of petroleum, is formed by emulsifying the fuel oil with water or an aqueous liquid, the fuel oil forming the dispersed phase and the aqueous liquid forming the continuous phase. An emulsion stabilizer, and optionally various other additives, notably a lower allyl alcohol, are included to stabilize the properties of the emulsion. The emulsion is prepared by heating the fuel oil, particularly No. 6 fuel oil, and the water to a temperature above about 60° C., and combining the two heated liquids in an appropriate ratio and shearing the mixture to form the macroemulsion.
    Type: Grant
    Filed: May 20, 1998
    Date of Patent: February 13, 2001
    Inventor: Rudolf W. Gunnerman
  • Patent number: 6117197
    Abstract: A fuel composition comprising a major amount of hydrocarbons boiling in the gasoline or diesel range and a fuel additive composition comprising (a) about 15 to 2,000 parts per million by weight of an aromatic ester of a polyalkylphenoxyalkanol, (b) about 30 to 2,000 parts per million by weight of a poly(oxyalkylene) amine, and (c) about 30 to 2,000 parts per million by weight of an aromatic di- or tri-carboxylic acid ester; wherein the total amount of components (a) and (b) is at least about 70 parts per million by weight, and further wherein the weight ratio of component (c) to the total amount of components (a) and (b) is at least about 0.25 to 1. The fuel compositions of this invention are useful for the prevention and control of engine deposits.
    Type: Grant
    Filed: November 25, 1998
    Date of Patent: September 12, 2000
    Assignee: Chevron Chemical Company LLC
    Inventor: Keith Robert Houser
  • Patent number: 6106584
    Abstract: Specific polymers of ethylene and different unsaturated esters provide oils with improved low temperature flow properties.
    Type: Grant
    Filed: August 4, 1998
    Date of Patent: August 22, 2000
    Assignee: Exxon Chemical Patents Inc
    Inventor: Iain More
  • Patent number: 6071319
    Abstract: A fuel additive composition comprising:(a) an aromatic ester compound of the formula: ##STR1## or a fuel soluble salt thereof, wherein R is hydroxy, nitro or --(CH.sub.2).sub.x --NR.sub.5 R.sub.6, wherein R.sub.5 and R.sub.6 are independently hydrogen or lower alkyl having 1 to 6 carbon atoms and x is 0 or 1;R.sub.1 is hydrogen, hydroxy, nitro or --NR.sub.7 R.sub.8, wherein R.sub.7 and R.sub.8 are independently hydrogen or lower alkyl having 1 to 6 carbon atoms;R.sub.2 and R.sub.3 are independently hydrogen or lower alkyl having 1 to 6 carbon atoms; andR.sub.4 is a polyalkyl group having an average molecular weight in the range of about 450 to 5,000; and(b) an aliphatic hydrocarbyl-substituted amine having at least one basic nitrogen atom, wherein the hydrocarbyl group has a number average molecular weight of about 400 to about 1,000.The fuel additive compositions of this invention are useful as fuel additives for the prevention and control of engine deposits.
    Type: Grant
    Filed: December 22, 1998
    Date of Patent: June 6, 2000
    Assignee: Chevron Chemical Company LLC
    Inventors: Jack E. Morris, Majid R. Ahmadi
  • Patent number: 6051039
    Abstract: This invention relates to a diesel fuel composition containing an additive composition made by admixing at least two components: A) at least one dicarboxylic acid having about 8 to about 500 carbon atoms or a reactive equivalent thereof; and B) at least one amine having about 6 to about 80 carbon atoms. In one embodiment, the additive composition also contains: C) at least one monocarboxylic acid of about 8 to about 28 carbon atoms or a reactive equivalent thereof. The additive composition is useful as a lubricity additive for diesel fuel, especially low sulfur diesel fuel and provide excellent storage stability, rust-inhibiting and anti-wear performance to diesel fuel.
    Type: Grant
    Filed: September 14, 1998
    Date of Patent: April 18, 2000
    Assignee: The Lubrizol Corporation
    Inventor: Shigeru Sugimoto
  • Patent number: 6039773
    Abstract: A polyamine-containing polyalkyl aromatic ester having the formula: ##STR1## or a fuel-soluble salt thereof; wherein R.sub.1 is a polyamine moiety having about 2 to about 12 amine nitrogen atoms and about 2 to about 40 carbon atoms, wherein the polyamine moiety is connected to the aromatic ring through one of its amine nitrogen atoms and R.sub.2 is a polyalkyl group having an average molecular weight in the range of about 450 to 5000.The polyamine-containing polyalkyl aromatic esters of the present invention are useful as fuel additives for the prevention and control of engine deposits.
    Type: Grant
    Filed: December 22, 1997
    Date of Patent: March 21, 2000
    Assignee: Chevron Chemical Company LLC
    Inventor: Richard E. Cherpeck
  • Patent number: 6013115
    Abstract: Engine deposits are reduced by adding an effective deposit-controlling amount of esteramine to hydrocarbon fuel.
    Type: Grant
    Filed: August 19, 1998
    Date of Patent: January 11, 2000
    Assignee: Akzo N.V.
    Inventors: Michael D. Kanakia, Ralph Franklin, Dale Steichen, James F. Gadberry
  • Patent number: 5964907
    Abstract: Engine deposits are reduced by adding an effective deposit-controlling amount of an esteramine to hydrocarbon fuel.
    Type: Grant
    Filed: August 14, 1996
    Date of Patent: October 12, 1999
    Assignee: Akzo Nobel N.V.
    Inventors: Robert F. Farmer, Ralph Franklin, Michael Kanakia, James F. Gadberry
  • Patent number: 5928393
    Abstract: A fuel additive which comprises a compound selected from a novel amine, oxygen-containing and nitrogen-containing compounds having selected structures. The inventive additive when blended with a gasoline serves to suppress sludge or deposits in fuel intake systems or combustion chambers for example of an automobile engine.
    Type: Grant
    Filed: July 17, 1997
    Date of Patent: July 27, 1999
    Assignee: Nippon Oil Co., Ltd.
    Inventors: Noboru Ishida, Katsuhiko Haji, Masaki Nagao, Toru Yoshii
  • Patent number: 5891203
    Abstract: This invention relates to the use of blends of diethanolamine derivatives and biodiesel as an additive for improving lubricity in low sulfur fuels and to fuels and additive concentrates comprising said lubricity additives.
    Type: Grant
    Filed: January 20, 1998
    Date of Patent: April 6, 1999
    Assignee: Ethyl Corporation
    Inventors: Keith Frederick Ball, John Gray Bostick, Timothy J. Brennan
  • Patent number: 5876467
    Abstract: Carboxylic esters of the formula IR.sup.1 --CO--O--R.sup.2 I,whereR.sup.1 is an aliphatic, straight-chain or branched hydrocarbon radical having alkyl side chains and a number average molecular weight of from 250 to 5000 andR.sup.2 is a straight-chain or branched hydrocarbon radical of 1 to 30 carbon atoms or a radical of the formula II ##STR1## where R.sup.3, R.sup.4, R.sup.5 and R.sup.6, independently of one another, are each hyrogen, branched or straight-chain alkyl, an aromatic radical or an araliphatic radical which may also contain heteroatoms,R.sup.7 and R.sup.8, independently of one another, are each branched or straight-chain alkyl or an aromatic or araliphatic radical which may also contain heteroatoms,X is O, S, NR.sup.9 or PR.sup.9, where R.sup.9 is an aliphatic or aromatic radical,n and m, independently of one another, are each from 2 to 20, andx is from 0 to 30,are used as fuel additives or lubricant additives, and fuel compositions or lubricant compositions contain these additives.
    Type: Grant
    Filed: August 12, 1996
    Date of Patent: March 2, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Arthur Hohn, Hans Funke, Knut Oppenlander, Wolfgang Gunther, Harald Schwahn
  • Patent number: 5865861
    Abstract: A polyamine-containing poly(oxyalkylene) aromatic ester having the formula: ##STR1## or a fuel-soluble salt thereof; where R.sub.1 is a polyamine moiety having about 2 to about 12 amine nitrogen atoms and about 2 to about 40 carbon atoms, wherein the polyamine moiety is connected to the aromatic ring through one of its amine nitrogen atoms, R.sub.2 and R.sub.3 are independently hydrogen or lower alkyl and each R.sub.2 and R.sub.3 is independently selected in each --O--CHR.sub.2 --CHR.sub.3 -unit; R.sub.4 is hydrogen, alkyl having 1 to about 100 carbon atoms, phenyl, aralkyl having about 7 to about 100 carbon atoms or alkaryl having about 7 to about 100 carbon atoms, or an acyl group of the formula: ##STR2## where R.sub.5 is alkyl having 1 to about 30 carbon atoms, phenyl, aralkyl having about 7 to about 36 carbon atoms or alkaryl having about 7 to about 36 carbon atoms; and y is an integer from about 5 to about 100.
    Type: Grant
    Filed: December 22, 1997
    Date of Patent: February 2, 1999
    Assignee: Chevron Chemical Company LLC
    Inventor: Richard E. Cherpeck
  • Patent number: 5849048
    Abstract: Substituted biphenyl poly(oxyalkylene) ethers having the formula: ##STR1## wherein R.sub.1 is hydrogen or hydroxyl; R.sub.2 is hydroxyl, cyano, nitro, amino, aminomethyl, N-alkylamino or N-alkylaminomethyl wherein the alkyl group contains 1 to about 6 carbon atoms, N,N-dialkylamino or N,N-dialkylaminomethyl wherein each alkyl group independently contains 1 to about 6 carbon atoms, with the proviso that R.sub.1 and R.sub.2 are ortho relative to each other and meta or para relative to the adjoining phenyl substitutent; R.sub.3 and R.sub.4 are independently hydrogen or lower alkyl having 1 to about 6 carbon atoms and each R.sub.3 and R.sub.4 is independently selected in each --OCHR.sub.3 --CHR.sub.4 -- unit; R.sub.5 is hydrogen, alkyl having 1 to about 100 carbon atoms, phenyl, aralkyl having about 7 to about 100 carbon atoms, alkaryl having about 7 to about 100 carbon atoms; or an acyl group having the formula: ##STR2## wherein R.sub.
    Type: Grant
    Filed: September 30, 1997
    Date of Patent: December 15, 1998
    Assignee: Chevron Chemical Company LLC
    Inventor: Richard E. Cherpeck
  • Patent number: 5827334
    Abstract: Substituted biphenyl polyalkyl esters having the formula: ##STR1## wherein R.sub.1 is hydrogen or hydroxyl; R.sub.2 is hydroxyl, cyano, nitro, amino, aminomethyl, N-alkylamino or N-alkylaminomethyl wherein the alkyl group contains 1 to about 6 carbon atoms, N,N-dialkylamino or N,N-dialkylaminomethyl wherein each alkyl group independently contains 1 to about 6 carbon atoms, with the proviso that R.sub.1 and R.sub.2 are ortho relative to each other and meta or para relative to the adjoining phenyl substitutent; and R.sub.3 is a polyalkyl group having an average molecular weight in the range of about 450 to about 5,000.The substituted biphenyl polyalkyl esters of the present invention are useful as fuel additives for the prevention and control of engine deposits.
    Type: Grant
    Filed: September 30, 1997
    Date of Patent: October 27, 1998
    Assignee: Chevron Chemical Company LLC
    Inventor: Richard E. Cherpeck
  • Patent number: 5814110
    Abstract: Distillate fuel is treated with additives whose structure match the crystal planes of the wax which crystallizes from the fuel to produce crystals below 4000 nanometres in size, suitable additive include novel sulpho-carboxylic materials particularly their esters and amine derivatives such as the amine salts and/or amides of ortho-sulpho benzoic acid.
    Type: Grant
    Filed: November 23, 1994
    Date of Patent: September 29, 1998
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Kenneth William Bartz, Jacqueline Dawn Bland, David Paul Gillingham, Richard Dix Kerwood, Edwin William Lehmann, Kenneth Lewtas, John Edward Maddox, Albert Rossi, Robert Dryden Tack
  • Patent number: 5782938
    Abstract: This invention concerns a an amidoalkanolaminoester composition obtained by reacting: (1) a reaction product of dialkyl maleate such as diethyl maleate and an alkylalkanolamine such as N-methylethanolamine; with (2) a hydrocarbyl oxypolyoxyalkene amine represented by the formula ##STR1## in which R represents an alkyl, an alicyclic, an alkylalicyclic radical having from 12 to 30 carbon atoms, or R'--Ar--; wherein R' represents a hydrocarbyl radical having from 4 to 12 carbon atoms; wherein x has a value of from about 10 to 16; wherein Ar is a divalent aromatic moiety such as divalent benzene; and wherein R" is an ethyl or methyl radical or a mixture of methyl and ethyl radicals. The amidoalkanolaminoester may be used as a fuel additive.
    Type: Grant
    Filed: May 23, 1997
    Date of Patent: July 21, 1998
    Assignee: Huntsman Petrochemical Corporation
    Inventor: Wei-Yang Su
  • Patent number: 5749929
    Abstract: A fuel additive composition comprising: (a) an aromatic ester compound of the formula: ##STR1## or a fuel soluble salt thereof, wherein R is hydroxy, nitro or --(CH.sub.2).sub.x --NR.sub.5 R.sub.6, wherein R.sub.5 and R.sub.6 are independently hydrogen or lower alkyl having 1 to 6 carbon atoms and x is 0 or 1;R.sub.1, is hydrogen, hydroxy, nitro or --NR.sub.7 R.sub.8, wherein R.sub.7 and R.sub.8 are independently hydrogen or lower alkyl having 1 to 6 carbon atoms;R.sub.2 and R.sub.3 are independently hydrogen or lower alkyl having 1 to 6 carbon atoms; andR.sub.4 is a polyalkyl group having an average molecular weight in the range of about 450 to 5,000; and(b) a poly(oxyalkylene) amine having at least one basic nitrogen atom and a sufficient number of oxyalkylene units to render the poly(oxyalkylene) amine soluble in hydrocarbons boiling in the gasoline or diesel fuel range.The fuel additive compositions of this invention are useful as fuel additives for the prevention and control of engine deposits.
    Type: Grant
    Filed: April 7, 1997
    Date of Patent: May 12, 1998
    Assignee: Chevron Chemical Company
    Inventors: Richard E. Cherpeck, Jack E. Morris, Majid R. Ahmadi
  • Patent number: 5728182
    Abstract: A polyalkyl ester of a substituted polyphenylether having the formula: ##STR1## wherein A is amino, aminomethyl, cyano, nitro, N-alkylamino or N-alkylaminomethyl wherein the alkyl group contains about 1 to about 6 carbon atoms, or N,N-dialkylamino or N,N-dialkylaminomethyl wherein each alkyl group independently contains about 1 to about 6 carbon atoms; R.sub.1 a polyalkyl group having an average molecular weight in the range of about 450 to about 5000; and x is an integer from about 1 to about 10 and y is an integer from 0 to about 10. The polyalkyl esters of the substituted polyphenyl ethers of the present invention are useful as fuel additives for the prevention and control of engine deposits.
    Type: Grant
    Filed: December 30, 1996
    Date of Patent: March 17, 1998
    Assignee: Chevron Chemical Company
    Inventor: Richard E. Cherpeck
  • Patent number: 5709719
    Abstract: A poly(oxyalkylene) ester of a substituted polyphenylether having the formula: ##STR1## wherein A is amino, aminomethyl, cyano, nitro, N-alkylamino or N-alkylaminomethyl wherein the alkyl group contains about 1 to about 6 carbon atoms, or N,N-dialkylamino or N,N-dialkylaminomethyl wherein each alkyl group independently contains about 1 to about 6 carbon atoms; R.sub.1 and R.sub.2 are independently hydrogen or lower alkyl having about 1 to about 6 carbon atoms and each R.sub.1 and R.sub.3 is independently selected in each --O--CHR.sub.1 -CHR.sub.2 - unit; R.sub.3 is hydrogen, alkyl having about 1 to about 100 carbon atoms, phenyl, aralkyl having about 7 to about 100 carbon atoms or alkaryl having about 7 to about 100 carbon atoms; x is an integer from about 1 to about 10, y is an integer from 0 to about 10; and z is an integer from about 1 to about 100.
    Type: Grant
    Filed: December 30, 1996
    Date of Patent: January 20, 1998
    Assignee: Chevron Chemical Company
    Inventor: Richard E. Cherpeck
  • Patent number: 5667539
    Abstract: Compounds of the formula I below are useful as additives in oleaginous compositions: ##STR1## wherein B represents an aromatic system, A represents a hydrocarbyl group, R.sup.1 and R.sup.2 are the same or are different and each independently is an aliphatic hydrocarbyl group containing 10-40 carbon atoms, provided that one of R.sup.1 and R.sup.2 may represent hydrogen; z is at least 1 and wherein the aromatic system carries at least one substituent group which is an activating group for the ring system or a derivative of an activating group.
    Type: Grant
    Filed: August 7, 1996
    Date of Patent: September 16, 1997
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Graham Jackson, Rachel Evelyn Mary Kenward, Barbara Catherine Brooke
  • Patent number: 5663435
    Abstract: Reaction products of amino-alkylenecarboxylic acids with polyoxyalkylene compounds are used as paraffin dispersants for mineral oil middle distillates.
    Type: Grant
    Filed: November 29, 1995
    Date of Patent: September 2, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Gabriele Dralle-Voss, Knut Oppenlander, Klaus Barthold, Bernd Wenderoth, Wolfgang Kasel
  • Patent number: 5628804
    Abstract: A polyether esteramide reaction product effective as a fuel additive for reducing intake valve deposits and octane requirement increase, as well as controlling combustion chamber deposits, in gasoline engines is disclosed together with fuel compositions and methods of making and using the same. The polyether esteramide reaction product contains two carbonyl groups. Preferably, the polyether esteramide contains an oxalyl group. Also disclosed are compositions and methods for dispersing deposits in lubricating oil products.
    Type: Grant
    Filed: December 21, 1995
    Date of Patent: May 13, 1997
    Assignee: Ethyl Corporation
    Inventor: John T. Loper
  • Patent number: 5628803
    Abstract: Compounds having the formula: ##STR1## and fuel soluble salts thereof; wherein R.sup.1 is nitro or --(CH.sub.2).sub.x --NR.sup.4 R.sup.5, wherein R.sup.4 and R.sup.5 are independently hydrogen or lower alkyl and x is 0 or 1; R.sup.2 is hydrogen, hydroxy, nitro, or --NR.sup.6 R.sup.7 wherein R.sup.6 and R.sup.7 are independently hydrogen or lower alkyl and R is a polyalkyl or polyalkyloxycarbonyl group. The compounds of formula I are useful as fuel additives for the prevention and control of engine deposits.
    Type: Grant
    Filed: December 29, 1995
    Date of Patent: May 13, 1997
    Assignee: Chevron Chemical Company
    Inventor: Richard E. Cherpeck
  • Patent number: 5618320
    Abstract: Aromatic esters of polyalkylphenoxyalkanols having the formula: ##STR1## or a fuel soluble salt thereof, wherein R is hydroxy, nitro or --(CH.sub.2).sub.x --NR.sub.5 R.sub.6, wherein R.sub.5 and R.sub.6 are independently hydrogen or lower alkyl having 1 to 6 carbon atoms and x is 0 or 1;R.sub.1 is hydrogen, hydroxy, nitro or --NR.sub.7 R.sub.8, wherein R.sub.7 and R.sub.8 are independently hydrogen or lower alkyl having 1 to 6 carbon atoms;R.sub.2 and R.sub.3 are independently hydrogen or lower alkyl having 1 to 6 carbon atoms; andR.sub.4 is a polyalkyl group having an average molecular weight in the range of about 450 to 5,000.The compounds of formula I are useful as fuel additives for the prevention and control of engine deposits.
    Type: Grant
    Filed: May 14, 1996
    Date of Patent: April 8, 1997
    Assignee: Chevron Chemical Company
    Inventor: Richard E. Cherpeck
  • Patent number: 5578091
    Abstract: Compounds of general formula (I) wherein X and Y are the same or different and are selected from the group consisting of SO.sub.3 (--), --CO--, --C(O)O(--), --R.sup.4 --C(O)O--, --NR.sup.3 C(O)--, --R.sup.4 O--, --R.sup.4 --C(O)O--, --R.sup.4 -- and --NC(O)--, R.sup.4 being --(CH.sub.2).sub.m -- where m is from 0 to 5 and R.sup.3 is defined below; X.sup.1 and Y.sup.1 are the same or different and are selected from the group consisting of (a), R.sup.1 and R.sup.2 being independently selected from the group consisting of alkyl, alkoxy alkyl or polyalkoxyalkyl groups that contain at least 10 carbon atoms in their main chain, and R.sup.3 being a hydrocarbyl group, each R.sup.
    Type: Grant
    Filed: October 13, 1992
    Date of Patent: November 26, 1996
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Graham Jackson, Rodger F. Andrews
  • Patent number: 5540743
    Abstract: A fuel additive having the formula: ##STR1## wherein A.sub.1 is amino, lower alkylamino or dialkylamino, or a polyamine radical; R.sub.1 and R.sub.2 are independently hydrogen, hydroxy, lower alkyl or lower alkoxy; R.sub.3 and R.sub.4 are independently hydrogen or lower alkyl; x is an integer from 0 to 10; n is an integer from 0 to 100; and when n is 0 to 10, R.sub.5 is polyalkyl having an average molecular weight of 450 to 5,000; and when n is 5 to 100, R.sub.5 is hydrogen, alkyl, phenyl, aralkyl, alkaryl or an acyl group having the formula: ##STR2## wherein R.sub.6 is alkyl, phenyl, aralkyl or alkaryl.
    Type: Grant
    Filed: December 30, 1994
    Date of Patent: July 30, 1996
    Assignee: Chevron Chemical Company
    Inventor: Richard E. Cherpeck
  • Patent number: 5482522
    Abstract: Mannich condensation products prepared by the condensation of a compound of the formula: ##STR1## wherein R.sub.1 is hydrogen, hydroxy, lower alkyl or lower alkoxy; R.sub.3 and R.sub.4 are independently hydrogen or lower alkyl; R.sub.5 is hydrogen, alkyl, phenyl, aralkyl, alkaryl, or an acyl group of the formula: ##STR2## wherein R.sub.6 is alkyl, phenyl, aralkyl or alkaryl; R.sub.7 is hydrogen, hydroxy, lower alkyl or lower alkoxy; n is an integer from 5 to 100; and x and y are each independently an integer from 0 to 10;with an aldehyde and a nitrogen base selected from ammonia, lower alkylamine, a polyamine and mixtures thereof.The condensation products and their fuel soluble salts are useful as fuel additives for the prevention and control of engine deposits.
    Type: Grant
    Filed: December 30, 1993
    Date of Patent: January 9, 1996
    Assignee: Chevron Chemical Company
    Inventor: Richard E. Cherpeck
  • Patent number: 5482523
    Abstract: Mannich condensation products prepared by the condensation of a compound of the formula: ##STR1## wherein R.sub.1 is hydrogen, hydroxy, lower alkyl or lower alkoxy; R.sub.3 and R.sub.4 are independently hydrogen or lower alkyl; R.sub.5 is hydrogen, alkyl, phenyl, aralkyl, alkaryl, or an acyl group of the formula: ##STR2## wherein R.sub.6 is alkyl, phenyl, aralkyl or alkaryl; R.sub.7 is alkyl; u is an integer from 1 to 10; n is an integer from 5 to 100; and x is an integer from 0 to 10;with an aldehyde and a nitrogen base selected from ammonia, lower alkylamine, a polyamine and mixtures thereof.The Mannich condensation products and their fuel soluble salts are useful as fuel additives for the prevention and control of engine deposits.
    Type: Grant
    Filed: November 2, 1994
    Date of Patent: January 9, 1996
    Assignee: Chevron Chemical Company
    Inventor: Richard E. Cherpeck
  • Patent number: 5433755
    Abstract: Additive formulation for engine fuels incorporating at least one constituent (A) and at least one constituent (B), constituent(A) consisting of at least one composition incorporating products resulting from the reaction of at least one dicarboxylic compound(D), whose carboxylic functions are separated by at the most eight carbon atoms, with at least one polyoxyalkylene glycol or glycol mono-ether (E) of general formula (I):R.sup.1 --O--(R.sup.2 --O).sub.n --H,in which R.sup.1 represents a hydrocarbon group having 1 to 30 carbon atoms, R.sup.2 represents a divalent hydrocarbon group having 2 to 6 carbon atoms and n is a number from 1 to 60; and constituent (B) consisting of at least one detergent-dispersant product. This formulation preferably also comprises a constituent (C) chosen from within the group formed by mineral or synthetic lubricating oils and polyglycols soluble in the fuel.
    Type: Grant
    Filed: August 31, 1992
    Date of Patent: July 18, 1995
    Assignees: Institut Francais du Petrole, Elf France
    Inventors: Philippe Mulard, Yvan Labruyere, Alain Forestiere, Roger Bregent
  • Patent number: 5425789
    Abstract: A compound of the general formula ##STR1## where X is CONR.sub.2 or CO.sub.2.sup.- + H.sub.2 NR.sub.2Y and Z are the same or different and selected from the group consisting of CONR.sub.2,CO.sub.2 R, OCOR, --OR, --R, --NCOR andone of Y or Z may be absent andR is selected from the group consisting of alkyl, alkoxy alkyl or polyalkoxyalkyl preferably containing at least 10 carbon atoms in the main chain.
    Type: Grant
    Filed: April 28, 1993
    Date of Patent: June 20, 1995
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Kenneth Lewtas, Edwin W. Lehmann, David P. Gillingham, John E. Maddox
  • Patent number: 5409507
    Abstract: Fuel compositions containing a major amount of hydrocarbons boiling in the gasoline or diesel range and an effective deposit-controlling amount of a poly(oxyalkylene) aromatic ether having the formula: ##STR1## where A.sub.1 is nitro, amino, N-alkylamino wherein the alkyl group contains 1 to 6 carbon atoms, or N,N-dialkylamino wherein each alkyl group independently contains 1 to 6 carbon atoms; R.sub.1 and R.sub.2 are independently hydrogen, hydroxy, lower alkyl, or lower alkoxy; R.sub.3 and R.sub.4 are independently hydrogen or lower alkyl and each R.sub.3 and R.sub.4 is independently selected in each --O--CHR.sub.3 --CHR.sub.4 -- unit; R.sub.5 is hydrogen, alkyl having 1 to 100 carbon atoms, phenyl, aralkyl having 7 to 100 carbon atoms or alkaryl having 7 to 100 carbon atoms, or an acyl group of the formula: ##STR2## where R.sub.
    Type: Grant
    Filed: October 28, 1993
    Date of Patent: April 25, 1995
    Assignee: Chevron Chemical Company
    Inventor: Richard E. Cherpeck
  • Patent number: 5409506
    Abstract: Additives which improve the low-temperature properties of distillate fuels are the reaction products of (1) diaminodiols, and (2) the product of pyromellitic dianhydride and aminoalcohols and/or amines with long-chain hydrocarbyl groups attached.
    Type: Grant
    Filed: September 14, 1993
    Date of Patent: April 25, 1995
    Assignee: Mobil Oil Corporation
    Inventors: David J. Baillargeon, Angeline B. Cardis, Dale B. Heck