Plural Nitrogens In The Hetero Ring (e.g., Piperazines, Etc.) Patents (Class 44/335)
  • Patent number: 10273425
    Abstract: A carrier fluid or fluidizer for use in fuel performance additives or fuels including such additives is described herein. The novel carrier fluids include a unique blend of alkoxylated alcohols or polyols providing unexpected performance improvements to fuel performance additives and fuels incorporating the additives. The carrier fluids, when combined with at least a detergent, provide desired valve stick performance and unexpectedly improve the intake valve deposit performance at the same time.
    Type: Grant
    Filed: March 13, 2017
    Date of Patent: April 30, 2019
    Assignee: Afton Chemical Corporation
    Inventors: Makaye Tabibi, Scott D. Schwab, Charles S. Shanahan, William J. Colucci
  • Patent number: 9783752
    Abstract: New, highly effective substantially pure Mannich detergents for use in hydrocarbon fuels reduce engine deposits in spark and compression ignition internal combustion engines. The Mannich condensation reaction products are obtainable by reacting: (i) a polyamine having primary amino groups, (ii) a hydrocarbyl-substituted hydroxyaromatic compound, and (iii) an aldehyde, wherein the reaction is conducted at in a molar ratio of (i):(ii):(iii) of approximately 1:2:3. The Mannich detergent compounds may be dispersed in a liquid carrier to provide a fuel additive concentrate for hydrocarbon engine fuels which effectively control engine deposit formation in intake valves, port fuel injectors and combustion chambers.
    Type: Grant
    Filed: December 15, 2006
    Date of Patent: October 10, 2017
    Assignee: Afton Chemical Corporation
    Inventors: Dennis J. Malfer, May D. Thomas
  • Patent number: 9487719
    Abstract: The present invention relates to methods of fueling an internal combustion engine, and composition, that provide improved nitrogen-free detergency in the engine, particularly in the area of injector deposit control. The present invention also provides methods of providing both improved detergency and improved corrosion inhibition, while avoiding compatibility problems with fuels and/or while limiting the amount of nitrogen delivered to the fuel from the deposit control additive.
    Type: Grant
    Filed: May 11, 2011
    Date of Patent: November 8, 2016
    Assignee: The Lubrizol Corporation
    Inventors: David C. Arters, Robert H. Barbour
  • Patent number: 8506288
    Abstract: A more complete combustion and a decrease in particulate emissions in the burning of a heavy fuel oil in an industrial boiler or similar combustion device is obtained by first heating the oil to a temperature sufficient to significantly lower its viscosity and continuously mixing a fuel additive containing a solution of a high molecular weight, substantially linear, viscoelastic polymer to the heated oil flowing to the combustion device by mechanically stirring the oil and additive at conditions that do not cause degradation of the viscoelastic polymer through rupture and breakage of polymer molecules.
    Type: Grant
    Filed: January 26, 2009
    Date of Patent: August 13, 2013
    Inventors: Shaul S. Epelbaum, Jerry C. Trippe
  • Patent number: 8308827
    Abstract: A diesel fuel containing a soot dispersant additive which is a grafted and derivatized low molecular weight copolymer of ethylene and at least one C3-C10 alpha monoolefin is provided. Also provided is a method for improving the fuel economy of a diesel engine which comprises operating the diesel engine with a fuel composition comprising (a) a major amount of a diesel fuel and (b) a minor fuel economy improving effective amount of the soot dispersant additive.
    Type: Grant
    Filed: January 11, 2010
    Date of Patent: November 13, 2012
    Assignee: Texaco, Inc.
    Inventors: C. Yvonne Thiel, Thomas E. Hayden
  • Publication number: 20120102826
    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: Application
    Filed: November 3, 2010
    Publication date: May 3, 2012
    Applicant: AFTON CHEMICAL CORPORATION
    Inventor: Xinggao FANG
  • Patent number: 7682410
    Abstract: The present invention refers to the use as gas odorant of alkoxy alkynes of formula (I) wherein R1 is methoxy or ethoxy; and R2 is hydrogen or methyl, to a process of odorizing gas and to fuel gas comprising it.
    Type: Grant
    Filed: November 8, 2005
    Date of Patent: March 23, 2010
    Assignee: Givaudan SA
    Inventors: Urs Mueller, John Norman Short
  • Publication number: 20080256847
    Abstract: The present invention refers to the use as gas odorant of alkoxy alkynes of formula (I) wherein R1 is methoxy or ethoxy; and R2 is hydrogen or methyl, to a process of odorizing gas and to fuel gas comprising it.
    Type: Application
    Filed: November 8, 2005
    Publication date: October 23, 2008
    Inventors: Urs Mueller, John Norman Short
  • Patent number: 7175678
    Abstract: The present invention provides a polymeric a fuel composition comprising (i) a fuel; and (ii) a polymeric compound; wherein the polymeric compound comprises at least one monomer unit of Formula I wherein R1 is H or a C1-10 hydrocarbyl group; wherein L is an optional C1-30 hydrocarbyl linker group; and wherein heterocycle is an optionally substituted heterocyclic ring.
    Type: Grant
    Filed: September 26, 2003
    Date of Patent: February 13, 2007
    Assignee: Innospec Limited
    Inventors: Cyrus Pershing Henry, David Leonard Pinch, Andrea Sneddon, Derek Richard Green
  • Patent number: 7157611
    Abstract: A method for marking a liquid petroleum hydrocarbon. The method comprises adding to the liquid petroleum hydrocarbon a pyrazinoporphyrazine dye having an absorption maximum from 700 nm to 900 nm.
    Type: Grant
    Filed: June 19, 2003
    Date of Patent: January 2, 2007
    Assignee: Rohm and Haas Company
    Inventors: Rajiv Manohar Banavali, Kim Sang Ho
  • Patent number: 7112230
    Abstract: Injector deposits in a direct injection gasoline engine are reduced by providing as fuel for the operation of said direct injection engine a fuel composition comprising a fuel-soluble compound having the formula (I): wherein R1 and R2 are independently C1-4 alkyl, R3 is a radical of the formula CmH2m wherein m is an integer of 2 to 6, R4 and R5 are each independently (i) hydrogen (ii) C1-4 alkyl, wherein R6 is selected from the group consisting of hydrogen and C1-4 alkyls and R7 is selected from the group consisting of hydrogen and C1-30 alkyl, (iv) wherein R8 is a saturated or unsaturated, linear, branched or cyclic, C7-23 hydrocarbyl group or (v) wherein R4 and R5 together with the nitrogen atom to which they are bonded, form a cyclic ring in which further hetero atoms.
    Type: Grant
    Filed: September 14, 2001
    Date of Patent: September 26, 2006
    Assignee: Afton Chemical Intangibles LLC
    Inventors: Dennis J. Malfer, Scott D. Schwab, Timothy J. Henly
  • Patent number: 6872230
    Abstract: The present invention relates to additives for enhancing the lubricity of hydrocarbon fuel oils, the inventive additive composition including one or more of the reaction products of (i) an alkylated polyamine and (ii) urea or isocyanate, or the salt adducts of these reaction products. More particularly, the present invention provides for a process for improving the lubricity of hydrocarbon fuel oils, which are low in inherent lubricity due to treatment to reduce sulfur and aromatic components for improved emissions.
    Type: Grant
    Filed: July 16, 2002
    Date of Patent: March 29, 2005
    Assignee: Betzdearborn, Inc.
    Inventors: Collin W. Cross, Zen-Yu Chang, S. Blake Pruett, Alan E. Goliaszewski
  • Patent number: 6835216
    Abstract: Compounds, preferably 5-pyrimidinol and 3-pyridinol derivatives, that act as effective chain breaking antioxidants of both the lipid and water-soluble variety (analogous to the natural Vitamins E and C), many of which are more reactive toward peroxyl radicals than the most potent form of Vitamin E. These compounds may exhibit many chemopreventive effects associated with conditions in which free radical-mediated cellular damage or disruption is implicated and Vitamins E and C are shown to have protective effects. Additionally, these compounds should be excellent oxidation inhibitors as additives to fuels, lubricants, rubber, polymers, chemicals, solvents and foodstuffs.
    Type: Grant
    Filed: June 26, 2001
    Date of Patent: December 28, 2004
    Assignee: Vanderbilt University
    Inventors: Derek A. Pratt, Luca Valgimigli, Gino A. DiLabio
  • Publication number: 20040123515
    Abstract: The present invention relates to fuel additives, fuel compositions and methods of manufacture in which the additives are provided to impart desired properties to fuels. These properties include, without limitation, reduction of nitrogen oxide and particulate emissions from the exhaust stream of internal combustion engines using the fuels. Preferred embodiments of an additive form of the composition include a nitrogen-containing compound selected from the group consisting of urea, cyanuric acid, triazine, ammonia and mixtures thereof, a carrier blend comprising an alkoxylated alcohol, a polyalkylene glycol ester and an alkanolamide and water. The additive may be provided in a concentrate form by addition of a solvent or may be provided as a final form fuel composition. A method of additive manufacture and is disclosed.
    Type: Application
    Filed: February 26, 2003
    Publication date: July 1, 2004
    Applicants: International Fuel Technology, Inc., Tomah Products, Inc.
    Inventors: James A. Krogh, Robert A. Swenson, Clifford J. Hazel, Ian V. Williamson
  • Publication number: 20040010964
    Abstract: A stable, substantially clear and homogeneous fuel composition contains an additive comprising a nitrogen donor and carrier, the nitrogen donor being present in an amount sufficient to reduce the NOx emissions of the fuel when subject to combustion and the carrier being selected to render the nitrogen donor soluble and to give the additive a molecular weight compatible with the energy properties of the fuel.
    Type: Application
    Filed: June 12, 2003
    Publication date: January 22, 2004
    Inventor: Ian Vernon Williamson
  • Patent number: 6676715
    Abstract: There is provided use of a thermal stabiliser for increasing the thermal stability of a cetane improver in a fuel composition comprising (i) a fuel, and (ii) the cetane improver wherein the thermal stabiliser is a compound of the formula H—R1 wherein H is a group comprising a heterocyclic group and R1 is a hydrocarbyl group having from 10 to 200 carbons.
    Type: Grant
    Filed: May 11, 2001
    Date of Patent: January 13, 2004
    Assignees: The Associated Octel Company Limited, Octel Starreon, LLC
    Inventors: Cyrus Pershing Henry, Barbara Elizabeth Goodrich
  • 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: 6328771
    Abstract: A fuel composition comprising a major amount of hydrocarbon fuel and a minor lubricity improving amount of a composition made by reacting component (A) with component (B) under unit-forming conditions; component (A) comprising a carboxylic acid represented by the formula R (COOH)n wherein R is a hydrocarbon group of 2 to 30 carbon atoms and n is a number in the range of 1 to 4, or an anhydride of said acid; and component (B) comprising a heterocylic aromatic amine.
    Type: Grant
    Filed: December 7, 1999
    Date of Patent: December 11, 2001
    Assignee: The Lubrizol Corporation
    Inventor: David J. Moreton
  • Patent number: 5856279
    Abstract: A process for reacting certain carboxylic reactants and at least one aldehyde or ketone with olefinic compounds then reacting the product prepared thereby with ammonia, a hydrazine or an amine, products prepared thereby and, additive concentrates, lubricating oil and fuel compositions.
    Type: Grant
    Filed: May 19, 1998
    Date of Patent: January 5, 1999
    Assignee: The Lubrizol Corporation
    Inventor: Mark R. Baker
  • Patent number: 5837016
    Abstract: A fuel additive which comprises an amide compound of the formula ##STR1## wherein R.sup.1 is hydrogen or a C.sub.1 -C.sub.30 hydrocarbon group, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 each are selected from the group consisting of hydrogen, a C.sub.1 -C.sub.10 hydrocarbon group and a group of formula (II), provided that at least one of R.sup.2, R.sup.3, R.sup.4 and R.sup.5 group of formula (II) R.sup.6 is a C.sub.2 -C.sub.6 alkylene group, R.sup.7 is a C.sub.1 -C.sub.6 alkylene group, a is an integer of 1-100, b is an integer of 0-100, the sum of a and b being equal to 1-200, c is an integer of 1-3, d is an integer of 0-2, the sum of c and d being equal to 3, and X is selected from the group consisting of hydrogen, a C.sub.1 -C.sub.30 hydrocarbon group, a group of formula (III), and a group of formula (IV), wherein formulas (II), (III) and (IV) are defined in the disclosure.
    Type: Grant
    Filed: April 10, 1997
    Date of Patent: November 17, 1998
    Assignee: Nippon Oil Co., Ltd.
    Inventors: Noboru Ishida, Takashi Nakano, Masaki Nagao, Takashi Kaneko
  • Patent number: 5779742
    Abstract: A process for reacting certain carboxylic reactants and at least one aldehyde or ketone with olefinic compounds then reacting the product prepared thereby with ammonia, a hydrazine or an amine, products prepared thereby and, additive concentrates, lubricating oil and fuel compositions.
    Type: Grant
    Filed: August 8, 1996
    Date of Patent: July 14, 1998
    Assignee: The Lubrizol Corporation
    Inventor: Mark R. Baker
  • Patent number: 5755833
    Abstract: A fuel additive comprising a urethane compound. A gasoline composition comprising gasoline blended with a urethane compound to suppress sludge or deposits in fuel intake systems or combustion chambers, such as an automobile engine.
    Type: Grant
    Filed: January 22, 1996
    Date of Patent: May 26, 1998
    Assignee: Nippon Oil Co., Ltd.
    Inventors: Noboru Ishida, Masaki Nagao, Takashi Kaneko
  • Patent number: 5584265
    Abstract: The invention discloses a method of reducing the concentration of NO.sub.x in the exhaust streams of internal combustion ignitions wherein a selected producing agent is introduced into the combustion chamber of such an engine via the fuel and/or air feed stream introduced into the combustion chamber. Also disclosed is an apparatus for reducing the concentration of NO.sub.x in the exhaust streams of internal combustion engines having a piston-cylinder assembly having an air fuel mixture contained therein, a means for storing a selective reducing agent selected from the group consisting of ammonia, hydrazine and cyanuric acid and a means for introducing the reducing agent into the lean air/fuel mixture before combustion occurs such that upon combustion of the air/fuel mixture, the reducing agent decomposes to react with one or more products of combustion to produce an engine exhaust stream having a reduced concentration of NO.sub.x.
    Type: Grant
    Filed: March 27, 1995
    Date of Patent: December 17, 1996
    Assignee: Ford Motor Company
    Inventors: Vemulapalli Durga N. Rao, Harry A. Cikanek
  • Patent number: 5478367
    Abstract: The addition to diesel or jet fuel of macrocyclic polyamines, especially those derived from PIBSA, or hydrocarbyl polyamines reduces particle emission, especially in association with organic nitrate cetane improvers.
    Type: Grant
    Filed: December 9, 1992
    Date of Patent: December 26, 1995
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Michael D. Sexton, Anthony K. Smith, Antonio Gutierrez, Stanley J. Brois
  • Patent number: 5460633
    Abstract: An additive comprising an oil-soluble polymer of a C2 to C6 mono-olefin such as polyisobutylene, which polymer has a molecular weight of less than about 500, is used in a fuel oil to reduce, on combustion of the fuel oil, one or more of particulate emissions, hydrocarbon emissions, carbon monoxide emissions, and oxides of nitrogen emissions.
    Type: Grant
    Filed: February 28, 1994
    Date of Patent: October 24, 1995
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Anthony K. Smith, Michael D. Sexton, Richard J. Hart
  • Patent number: 5460634
    Abstract: An additive comprising an oil-soluble stable free radical, such as a nitroxide, or a precursor therefor, is used in a fuel oil to reduce, on combustion of the fuel oil, one or more of particulate emissions, hydrocarbon emissions, carbon monoxide emissions, and oxides of nitrogen emissions.
    Type: Grant
    Filed: February 28, 1994
    Date of Patent: October 24, 1995
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Carlo Fava, Wolfgang W. J. Gschwendtner, Anthony K. Smith, Michael D. Sexton, Richard J. Hart
  • Patent number: 5324334
    Abstract: There are disclosed macrocyclic and polycyclic polyamine lubricating oil additives formed by cyclodehydration of reaction products of hydrocarbon substituted succinic anhydrides or carboxylic acids with poly 3-amino propyl compounds or by acylation of macrocyclic polyamines and polycyclic polyamines with hydrocarbon substituted succinic anhydride or carboxylic acids. These compounds are useful as dispersants and dispersants-V.I. improvers in both gasoline and diesel engine lubricating oil compositions and are also useful fuel additives.
    Type: Grant
    Filed: October 28, 1992
    Date of Patent: June 28, 1994
    Assignee: Exxon Research & Engineering
    Inventors: Stanley J. Brois, Antonio Gutierrez
  • Patent number: 5266080
    Abstract: The flame luminosity of a methanol fuel is appreciably enhanced by the addition thereto of at least one flame luminosity enhancing agent selected from the group consisting of azine dye, triarylmethane dye, fluorescein dye, imine dye and anthraquinone dye, said dye excluding any metal component whose combustion product(s) tend to cause excessive wear in an engine operated with the fuel composition or tend to significantly interfere with normal operation of such engine or any of its associated systems, the flame luminosity of the fuel composition during burning being appreciably enhanced relative to the flame luminosity of the same burning fuel composition but to which no flame luminosity enhancing agent has been added.
    Type: Grant
    Filed: October 11, 1989
    Date of Patent: November 30, 1993
    Assignee: The Standard Oil Company
    Inventors: Thomas E. Kiovsky, Wendy L. Clark
  • Patent number: 5162049
    Abstract: This invention relates to stabilizer additives for hydrocarbonaceous fuels comprising at least one or a mixture of hexahydrotriazine compounds and at least one or a mixture of imine compounds.
    Type: Grant
    Filed: September 9, 1991
    Date of Patent: November 10, 1992
    Assignee: Ethyl Petroleum Additives
    Inventors: John G. Bostick, Lawrence J. Cunningham
  • Patent number: 5158667
    Abstract: This invention relates to processes for inhibiting fouling in fluid catalytic cracking units. The processes comprise adding to the hydrocarbon being processed a polymer formation inhibiting amount of aminoethyl piperazine.
    Type: Grant
    Filed: August 23, 1991
    Date of Patent: October 27, 1992
    Assignee: Betz Laboratories, Inc.
    Inventors: Raymon C. Barlow, Dwight K. Reid
  • Patent number: 5158666
    Abstract: The present invention is directed to an antioxidant material and its use in petroleum and petrochemical processes to reduce and/or control fouling problems specifically as regards hydrocarbons having a bromine number of 10 or less and containing oxygen. The inventive antioxidant material is 1-(2-aminoethyl) piperazine.
    Type: Grant
    Filed: August 13, 1990
    Date of Patent: October 27, 1992
    Assignee: Betz Laboratories, Inc.
    Inventor: Dwight K. Reid
  • Patent number: 5024677
    Abstract: Rust of ferrous metal surfaces that are in contact with gasohol or alcohol fuels is inhibited by the addition of a corrosion inhibiting amount of the combination of (A) a substituted imidazoline and (B) an alkenyl succinimide of a mixture of alkylenepolyamines.
    Type: Grant
    Filed: June 11, 1990
    Date of Patent: June 18, 1991
    Assignee: Nalco Chemical Company
    Inventors: Sophia L. Wang, George R. Meyer, Kerry C. Brinkman
  • Patent number: 5000759
    Abstract: A stable middle distillate fuel-oil composition which comprises(a) a major portion of a middle distillate fuel-oil; and(b) a minor amount, as storage stabilizing additive, of a N-2-pyridyl succinimide of a copolymer and maleic anhydride graft.
    Type: Grant
    Filed: August 3, 1989
    Date of Patent: March 19, 1991
    Assignee: Texaco Inc.
    Inventors: Theodore E. Nalesnik, Sheldon Herbstman