Benzene Ring Attached Indirectly To The Nitrogen By Acyclic Nonionic Bonding Patents (Class 44/424)
  • Patent number: 10260016
    Abstract: Unleaded aviation gasoline. An aviation gasoline fuel blend includes an unleaded aviation gasoline base fuel, with an effective amount of selected alkyl benzenes to improve the functional engine performance to avoid harmful detonation sufficient to meet or exceed selected standards for detonation performance requirements in full scale aircraft piston spark ignition engines designed for use with Grade 100LL avgas. Selected alkyl benzenes such as 1,3-dimethylbenzene, and/or 1,3,5-trimethylbenzene, or other mixtures thereof, may be used. Suitable alkylated benzenes may include a mixture of xylene isomers. Aromatic amines, such as m-toluidine, may also be added to increase MON. Base fuels may be a high quality aviation alkylate, or may be a commercial iso-octane, or a mixture of high quality aviation alkylate enhanced by commercial iso-octane, and may include iso-pentane or butane or both iso-pentane and butane in sufficient quantity to provide appropriate vapor pressure for the final fuel blend.
    Type: Grant
    Filed: March 15, 2013
    Date of Patent: April 16, 2019
    Inventor: George W. Braly
  • Patent number: 9938479
    Abstract: The present invention relates to the use of amines and/or Mannich adducts as detergents and/or dispersants in fuel and lubricant compositions for direct-injection gasoline engines. The invention further relates to fuel and lubricant compositions which comprise at least one such Mannich adduct, and also a bisaminoalkylated Mannich adduct.
    Type: Grant
    Filed: March 7, 2016
    Date of Patent: April 10, 2018
    Assignee: BASF SE
    Inventors: Arno Lange, Hans Peter Rath, Marc Walter, Marco Bergemann, Helmut Schmidt
  • Patent number: 9309475
    Abstract: The present invention relates to the use of amines and/or Mannich adducts as detergents and/or dispersants in fuel and lubricant compositions for direct-injection gasoline engines. The invention further relates to fuel and lubricant compositions which comprise at least one such Mannich adduct, and also a bisaminoalkylated Mannich adduct.
    Type: Grant
    Filed: April 25, 2013
    Date of Patent: April 12, 2016
    Assignee: BASF SE
    Inventors: Arno Lange, Hans Peter Rath, Marc Walter, Marco Bergemann, Helmut Schmidt
  • Patent number: 9142863
    Abstract: A nanoparticle organic hybrid material (NOHM) containing an organic polymeric corona having a molecular weight in a range of 100-50,000 g/mol, wherein the organic polymeric corona is covalently attached to an inorganic nanoparticle core, wherein the NOHM exhibits liquid-like properties so that the NOHM moves freely and flows in a manner so that when the NOHM is in a container, the NOHM takes the shape of the container, and wherein the NOHM has a volume fraction (fc) of the inorganic particle ranging from about 0.05 to 0.75, methods of making the NOHMs, and compositions containing the NOHMs.
    Type: Grant
    Filed: January 30, 2013
    Date of Patent: September 22, 2015
    Assignee: Cornell University
    Inventors: Lynden A. Archer, Laura Lynne Olenick, Jennifer Lyn Schaefer, Alexandra Mirella Elena Corona, Daniel Kim
  • 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
  • Patent number: 8771385
    Abstract: Use in a gas oil fuel composition, which preferably comprises a Fischer-Tropsch derived fuel, of a compound according to formula (I): wherein: R1 to R5 are each independently hydrogen or a C1-10 alkyl group, where such alkyl groups may be the same as or different from one another; X is a nitrogen- or oxygen-containing group, for the purpose of reducing the cetane number of said fuel composition; preparation of such a fuel composition; and operating a fuel consuming system.
    Type: Grant
    Filed: December 28, 2009
    Date of Patent: July 8, 2014
    Assignee: Shell Oil Company
    Inventors: Claire Griffins, Richard Hugh Clark, Christopher William Clayton, Paul Anthony Stevenson, Robert Wilfred Matthews Wardle
  • Publication number: 20130255139
    Abstract: Modified alkylphenol-aldehyde resins include one or more alkylamines, having preferably at least one primary amine type group as well as their use for improving the flow properties of motor fuels and hydrocarbon fuels, such as in particular jet fuel, gas oil, fuel oil domestic, heavy fuel oil.
    Type: Application
    Filed: December 21, 2011
    Publication date: October 3, 2013
    Applicant: TOTAL RAFFINAGE MARKETING
    Inventors: Nelly Dolmazon, Géraldine Papin, Frédéric Tort
  • Publication number: 20130237466
    Abstract: The present invention relates to the use of amines and/or Mannich adducts as detergents and/or dispersants in fuel and lubricant compositions for direct-injection gasoline engines. The invention further relates to fuel and lubricant compositions which comprise at least one such Mannich adduct, and also a bisaminoalkylated Mannich adduct.
    Type: Application
    Filed: April 25, 2013
    Publication date: September 12, 2013
    Applicant: BASF SE
    Inventors: Arno LANGE, Hans Peter RATH, Marc WALTER, Marco BERGEMANN, Helmut SCHMIDT
  • Patent number: 8409474
    Abstract: The use of polycyclic phenolic compounds which have up to 20 benzene rings per molecule and are obtainable by reacting a tetrahydrobenzoxazine I where R1 is a hydrocarbyl radical and R2, R3, R4 and R5 are each independently hydrogen atoms, hydroxyl groups or hydrocarbyl radicals with one or more of the same or different phenols II where R7, R8, R9 and R10 are each independently hydrogen atoms, hydroxyl groups or hydrocarbyl radicals, and/or with one or more of the same or different tetrahydrobenzoxazines I, with the proviso that at least one of the substituents has from 13 to 3000 carbon atoms and the remaining substituents, when they are hydrocarbyl radicals, have in each case from 1 to 20 carbon atoms as stabilizers for stabilizing inanimate organic material against the action of light, oxygen and heat.
    Type: Grant
    Filed: February 21, 2007
    Date of Patent: April 2, 2013
    Assignee: BASF SE
    Inventors: Arno Lange, Helmut Mach, Hans Peter Rath, Dietmar Posselt
  • Patent number: 8377336
    Abstract: The use of polycyclic phenolic compounds which have up to 20 benzene rings per molecule and are obtainable by reacting a tetrahydrobenzoxazine I where R1 is a hydrocarbyl radical and R2, R3, R4 and R5 are each independently hydrogen atoms, hydroxyl groups or hydrocarbyl radicals with one or more of the same or different phenols II where R7, R8, R9 and R10 are each independently hydrogen atoms, hydroxyl groups or hydrocarbyl radicals, and/or with one or more of the same or different tetrahydrobenzoxazines I, with the proviso that at least one of the substituents has from 13 to 3000 carbon atoms and the remaining substituents, when they are hydrocarbyl radicals, have in each case from 1 to 20 carbon atoms as stabilizers for stabilizing inanimate organic material against the action of light, oxygen and heat.
    Type: Grant
    Filed: January 28, 2011
    Date of Patent: February 19, 2013
    Assignee: BASF SE
    Inventors: Arno Lange, Helmut Mach, Hans Peter Rath, Dietmar Posselt
  • 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: 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
  • Publication number: 20110113678
    Abstract: The use of polycyclic phenolic compounds which have up to 20 benzene rings per molecule and are obtainable by reacting a tetrahydrobenzoxazine I where R1 is a hydrocarbyl radical and R2, R3, R4 and R5 are each independently hydrogen atoms, hydroxyl groups or hydrocarbyl radicals with one or more of the same or different phenols II where R7, R8, R9 and R10 are each independently hydrogen atoms, hydroxyl groups or hydrocarbyl radicals, and/or with one or more of the same or different tetrahydrobenzoxazines I, with the proviso that at least one of the substituents has from 13 to 3000 carbon atoms and the remaining substituents, when they are hydrocarbyl radicals, have in each case from 1 to 20 carbon atoms as stabilizers for stabilizing inanimate organic material against the action of light, oxygen and heat.
    Type: Application
    Filed: January 28, 2011
    Publication date: May 19, 2011
    Applicant: BASF SE
    Inventors: Arno Lange, Helmut Mach, Hans Peter Rath, Dietmar Posselt
  • Patent number: 7824454
    Abstract: A unique combination of a certain poly(oxyalkylene) amine and a thiadiazole compound when employed as a fuel additive in a hydrocarbon fuel such as gasoline or diesel fuel will preclude fuel gauge sending units from sustaining sulfur-related corrosion damage or restore fuel gauge sending units, particularly silver-based fuel gauge sending units, in vehicle fuel storage tanks to like-new operational condition. Moreover, a method suitable for use in precluding fuel gauge sending units from sustaining sulfur-related corrosion damage or restoring silver-based fuel gauge sending units in gasoline or diesel vehicle fuel storage tanks to like-new operational condition using the combination of a certain poly(oxyalkylene) amine and a thiadiazole compound as a fuel additive is also described.
    Type: Grant
    Filed: August 17, 2004
    Date of Patent: November 2, 2010
    Assignee: Chevron Oronite Company LLC
    Inventor: Stephen M. Moore
  • Publication number: 20100263261
    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,R2R3,R4,R5 and R6 is independently selected from hydrogen, and an optionally substituted alkyl, alkenyl, alkynyl, aryl, alkylaryl or arylalkyl substituent.
    Type: Application
    Filed: September 25, 2008
    Publication date: October 21, 2010
    Inventor: Jacqueline Reid
  • Publication number: 20100236139
    Abstract: A fuel oil composition comprising a major amount of a fuel oil and a minor amount of a compound being the product of the 1,4-addition reaction of (i) ammonia, a primary or secondary hydrocarbyl-substituted amine or a mixture thereof to (ii) a species containing one or more ?,?-unsaturated carbonyl groups, wherein the compound includes at least one hydrocarbyl group containing at least 10 carbon atoms. The fuel oil composition has improved low temperature properties.
    Type: Application
    Filed: December 10, 2009
    Publication date: September 23, 2010
    Inventor: Graham Jackson
  • Publication number: 20090071065
    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 or 1:1:2. 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: Application
    Filed: September 8, 2008
    Publication date: March 19, 2009
    Applicant: AFTON CHEMICAL CORPORATION
    Inventors: Dennis J. Malfer, May D. Thomas
  • Publication number: 20080134571
    Abstract: An unleaded fuel composition comprising: a combination of alkylated benzenes comprising alkyl groups having from 1 to 4 carbon atoms; 5 vol. % or more of one or more aromatic amines; and, an isoparaffin composition selected from the group consisting of alkylate, a combination of isoparaffins having a total number of carbon atoms of 11 or less, and combinations thereof.
    Type: Application
    Filed: December 12, 2006
    Publication date: June 12, 2008
    Inventors: Jorg LANDSCHOF, Michael Clifford MACKNAY, Timothy Michael SHEA
  • Patent number: 6800103
    Abstract: New, highly effective detergent/dispersants for use in spark-ignition fuels comprising Mannich condensation products formed from (i) at least one substituted hydroxyaromatic compound having on the ring both (a) an aliphatic hydrocarbyl substituent derived from a polyolefin having a number average molecular weight in the range of about 500 to about 3000, and (b) a C1-4 (ii) at least one secondary amine; and (iii) at least one aldehyde are described. Carrier such as ploy(oxyalkylene) compounds further enhance the effectiveness of these Mannich condensation products in minimizing or reducing intake valve deposits and/or intake valve sticking.
    Type: Grant
    Filed: February 2, 2001
    Date of Patent: October 5, 2004
    Assignee: Ethyl Corporation
    Inventors: Dennis J. Malfer, Andrea T. Noble, William J. Colucci, Roger M. Sheets
  • Patent number: 6660050
    Abstract: A method for controlling the deposits in the fuel vaporizer of a fuel reformer used to prepare a liquid hydrocarbon for use as a fuel in a fuel cell which comprises introducing into the fuel vaporizer a liquid hydrocarbon containing an effective deposit controlling amount of a nitrogen-containing detergent additive and a fuel composition suitable for use in a fuel cell which comprises a liquid hydrocarbon having a boiling range at atmospheric pressure falling between about 77 degrees F. (25 degrees C.) and about 437 degrees F. (225 degrees C.), a total sulfur content of less than 3 ppm, and containing an effective deposit controlling amount of a nitrogen-containing detergent additive.
    Type: Grant
    Filed: May 23, 2002
    Date of Patent: December 9, 2003
    Assignee: Chevron U.S.A. Inc.
    Inventors: Gunther H. Dieckmann, James D. Kramer, Richard E. Cherpeck
  • Publication number: 20030150154
    Abstract: Polyalkylphenoxyaminoalkanes having the formula: 1
    Type: Application
    Filed: December 21, 2001
    Publication date: August 14, 2003
    Inventor: Richard E. Cherpeck
  • Publication number: 20020134006
    Abstract: New, highly effective detergent/dispersants for use in spark-ignition fuels comprising Mannich condensation products formed from (i) at least one substituted hydroxyaromatic compound having on the ring both (a) an aliphatic hydrocarbyl substituent derived from a polyolefin having a number average molecular weight in the range of about 500 to about 3000, and (b) a C1-4 (ii) at least one secondary amine; and (iii) at least one aldehyde are described. Carrier such as ploy(oxyalkylene) compounds further enhance the effectiveness of these Mannich condensation products in minimizing or reducing intake valve deposits and/or intake valve sticking.
    Type: Application
    Filed: February 2, 2001
    Publication date: September 26, 2002
    Inventors: Dennis J. Malfer, Andrea T. Noble, William J. Colucci, Roger M. Sheets
  • Patent number: 6372000
    Abstract: A hydrocarbyl polyoxyalkylene aminoalcohol of the general formula wherein R1 is an alkyl, an alicyclic or an alkylalicyclic radical having from about 4 to about 30 carbon atoms or an alkylaryl where the alkyl group is from about 4 to about 30 carbon atoms; x is an integer from 0 to about 5, y is an integer from 1 to about 49, z is an integer from 1 to about 49 and the sum of x+y+z is equal to 3 to about 50; R2 and R3 each is different and is an alkyl group of from 1 to 4 carbon atoms and each oxyalkylene radical can be any combination of repeating oxyalkylene units to form random or block copolymers; R4 is the same as R2 or R3; R5 is hydrogen or where R7 is hydrogen or an alkyl group of from 1 to 5 carbon atoms and R6 is hydrogen or an alkyl group of from 1 to 5 carbon atoms and an internal combustion engine fuel composition containing same are provided.
    Type: Grant
    Filed: November 30, 1999
    Date of Patent: April 16, 2002
    Assignee: Texaco Inc.
    Inventors: Thomas F. DeRosa, Joseph M. Russo, Benjamin J. Kaufman, James R. Ketcham, Richard V. Kessler, Frank J. DeBlase
  • Patent number: 6346128
    Abstract: A two-cycle engine fuel composition comprising (a) a major amount of a two-cycle engine fuel; (b) a lubricant component; and, (c) a two-cycle engine fuel combustion deposit-inhibiting amount of at least one hydrocarbyl polyoxyalkylene aminoalcohol of the general formula wherein R1 is an alkyl, an alicyclic or an alkylalicyclic radical having from about 4 to about 30 carbon atoms or an alkylaryl where the alkyl group is from about 4 to about 30 carbon atoms; x is an integer from 0 to about 5, y is an integer from 1 to about 49, z is an integer from 1 to about 49 and the sum of x+y+z is equal to 3 to about 50; R2 and R3 each is different and is an alkyl group of from 1 to 4 carbon atoms and each oxyalkylene radical can be any combination of repeating oxyalkylene units to form random or block copolymers; R4 is the same as R2 or R3; R5 is hydrogen or where R7 is hydrogen or an alkyl group of from 1 to 5 carbon atoms and R6 is hydrogen or an alkyl group of from 1 to 5
    Type: Grant
    Filed: November 30, 1999
    Date of Patent: February 12, 2002
    Assignee: Texaco Inc.
    Inventors: Thomas F. DeRosa, Jeffrey M. Burns, Benjamin J. Kaufman, Robert J. Bacchi, Serge A. Cryvoff, James R. Ketcham
  • Patent number: 6267791
    Abstract: Mixtures of at least one amine, polyamine or alkanolamine and at least one polyetheramine and their use as additives for gasoline engine fuels.
    Type: Grant
    Filed: August 2, 1995
    Date of Patent: July 31, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Juergen Thomas, Peter Schreyer, Knut Oppenlaender, Wolfgang Guenther, Lothar Franz
  • Patent number: 6176886
    Abstract: Mannich reaction products are disclosed as additives for hydrocarbon fuels. The Mannich reaction products are added to a low sulfur content, middle-distillate, compression ignition fuels in an amount effective to improve the lubricity of the fuel, typically within the range of from about 10 to about 1000 parts of additive per million parts fuel (ppm w/w), and thereby reduce the wear occasioned upon the fuel pump. Compositions comprising a hydrocarbon fuel and the reaction product are also disclosed.
    Type: Grant
    Filed: August 31, 1999
    Date of Patent: January 23, 2001
    Assignee: Ethyl Corporation
    Inventors: John T. Loper, Robert Quigley, Timothy J. Henly
  • Patent number: 6063145
    Abstract: This invention concerns a fuel additive comprising an etheramine alkoxylate, and fuel compositions and additive concentrates made therefrom. The etheramine alkoxylate may be of formula: ##STR1## where R.sup.1 is a straight or branched alkyl, or alkylaryl; R.sup.2 is independently in each occurrence hydrogen or alkyl from 1 to 6 carbons; R.sup.3 is independently in each occurrence hydrogen or alkyl of from 1 to 6 carbons; m averages from about 2 to about 20; and x and y each independently average from about 0 to 2, where x+y averages from about 1 to about 4.
    Type: Grant
    Filed: June 26, 1998
    Date of Patent: May 16, 2000
    Assignee: Huntsman Petrochemical Corporation
    Inventors: John M. Larkin, Wei-Yang Su, Terry L. Renken
  • Patent number: 5851242
    Abstract: A fuel additive composition comprising:(a) a polyalkylphenoxyaminoalkane having the formula: ##STR1## or a fuel soluble salt thereof, wherein R is a polyalkyl group having an average molecular weight in the range of about 600 to 5,000;R.sub.1 and R.sub.2 are independently hydrogen or lower alkyl having 1 to 6 carbon atoms; andA is amino, N-alkyl amino having about 1 to about 20 carbon atoms in the alkyl group, N,N-dialkyl amino having about 1 to about 20 carbon atoms in each alkyl group, or a polyamine moiety having about 2 to about 12 amine nitrogen atoms and about 2 to about 40 carbon atoms; 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 30, 1997
    Date of Patent: December 22, 1998
    Assignee: Chevron Chemical Company
    Inventors: Richard E. Cherpeck, Jack E. Morris, Majid R. Ahmadi
  • 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: 5830244
    Abstract: A fuel additive having the formula: ##STR1## wherein R.sub.1 and R.sub.2 are independently hydrogen or lower alkyl; 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.6 is alkyl having 1 to 30 carbon atoms, phenyl, aralkyl having 7 to 36 carbon atoms or alkaryl having 7 to 36 carbon atoms; n is an integer from 5 to 100; and x is an integer from 0 to 10.
    Type: Grant
    Filed: December 30, 1996
    Date of Patent: November 3, 1998
    Assignee: Chevron Chemical Company
    Inventor: Richard E. Cherpeck
  • Patent number: 5827333
    Abstract: Substituted biphenyl polyalkyl 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; and R.sub.3 is a polyalkyl group having an average molecular weight in the range of about 450 to about 5,000.The subsitituted biphenyl polyalkyl ethers 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: 5752991
    Abstract: Very long chain alkylphenyl polyoxyalkylene amines having the formula: ##STR1## wherein R.sub.1 is an alkyl group having at least 40 carbon atoms; R.sub.2 and R.sub.3 are each independently hydrogen or lower alkyl having about 1 to about 2 carbon atoms and each R.sub.2 and R.sub.3 is independently selected in each --O--CHR.sub.2 --CHR.sub.3 -- unit;A is an amine moiety derived from ammonia, a primary alkyl monoamine having about 1 to 20 carbon atoms, a secondary dialkyl monoamine having about 1 to 20 carbon atoms in each alkyl group, or a polyamine having about 2 to about 12 amine nitrogen atoms and about 2 to about 40 carbon atoms;x is an integer from about 1 to about 2; and y is an integer from about 5 to about 50.The very long chain alkylphenyl polyoxyalkylene amines of the present invention are useful as fuel additives for the prevention and control of engine deposits.
    Type: Grant
    Filed: December 29, 1995
    Date of Patent: May 19, 1998
    Assignee: Chevron Chemical Company
    Inventor: Frank Plavac
  • Patent number: 5709720
    Abstract: Aromatic ethers 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 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: November 7, 1996
    Date of Patent: January 20, 1998
    Assignee: Chevron Chemical Company
    Inventor: Richard E. Cherpeck
  • Patent number: 5669939
    Abstract: Polyalkylphenoxyaminoalkanes having the formula: ##STR1## wherein R is a polyalkyl group having an average molecular weight in the range of about 600 to 5,000;R.sub.1 and R.sub.2 are independently hydrogen or lower alkyl having 1 to 6 carbon atoms; andA is amino, N-alkyl amino having about 1 to about 20 carbon atoms in the alkyl group, N,N-dialkyl amino having about 1 to about 20 carbon atoms in each alkyl group, or a polyamine moiety having about 2 to about 12 amine nitrogen atoms and about 2 to about 40 carbon atoms.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: September 23, 1997
    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: 5637119
    Abstract: Substituted aromatic polyalkyl ethers having the formula: ##STR1## wherein R.sub.1 is a polyalkyl group having an average molecular weight of about 450 to about 5,000;A is nitro, amino, cyano, aminomethyl, N-alkylamino or N-alkylaminomethyl wherein the alkyl group contains from about 1 to about 6 carbon atoms, or N,N-dialkylamino or N,N-dialkylaminomethyl wherein each alkyl group independently contains from about 1 to about 6 carbon atomsx is an integer from about 0 to about 1; and y is an integer from about 0 to about 10 with the proviso that one of x and y must be 0 and the other must be greater than 0.The substituted aromatic polyalkyl ethers of the present invention are useful as fuel additives for the prevention and control of engine deposits.
    Type: Grant
    Filed: December 29, 1995
    Date of Patent: June 10, 1997
    Assignee: Chevron Chemical Company
    Inventor: Richard E. Cherpeck
  • Patent number: 5516443
    Abstract: A novel compound comprises a chemical compound comprising or including a cyclic ring system such as an aromatic ring system, the compound carrying at least two substituents of the general formula (I) below on the ring system--A--NR.sup.1 R.sup.2 (I)where A is an aliphatic hydrocarbyl group that is optionally interrupted by one or more hetero atoms and that is straight chain or branched, and R.sup.1 and R.sup.2 are the same or different and each is independently a hydrocarbyl group containing 9 to 40 carbon atoms, optionally interrupted by one or more hetero atoms, the substituents being the same or different and the compound optionally being in the form of a salt thereof.Such compounds may be used as additives for improving the cold flow properties of crude oil, lubricating oil or fuel oil.
    Type: Grant
    Filed: February 18, 1994
    Date of Patent: May 14, 1996
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Graham Jackson, Rachel E. M. Kenward
  • Patent number: 5512067
    Abstract: Compounds are described in which a polyamine moiety is linked to a phenolic moiety by a Mannich base linkage involving one of the amino groups of the polyamine moiety, and in which an aminoalkylene-poly(oxyalkylene) moiety is linked to the phenolic moiety by a Mannich base linkage involving an amino group of the alkylene-poly(oxyalkylene) moiety. Compounds of this type have been found to be highly effective in controlling the formation of intake valve deposits in internal combustion engines.
    Type: Grant
    Filed: May 22, 1995
    Date of Patent: April 30, 1996
    Assignee: Ethyl Corporation
    Inventor: John T. Loper
  • 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: 5306316
    Abstract: Poly(alkylene ether) amines having the formula: ##STR1## wherein A is an amine moiety having at least one basic nitrogen atom; R.sub.1 is a hydrocarbyl group having a sufficient number of carbon atoms to render the poly(vinyl ether) amine soluble in hydrocarbons boiling in the gasoline or diesel fuel range; R.sub.2 is an alkylene group having 2 to about 8 carbon atoms; R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are each independently hydrogen or a lower alkyl group having 1 to about 4 carbon atoms; R.sub.9 is an alkyl group having 1 to about 10 carbon atoms; m is 0 or 1; n is an integer from 5 to 99; and W is a hydroxy(oxypropylene) group having the formula: ##STR2## or mixtures thereof. The poly(vinyl ether) amines of formula I are useful as fuel additives for the prevention and control of engine deposits.
    Type: Grant
    Filed: April 1, 1993
    Date of Patent: April 26, 1994
    Assignee: Chevron Research and Technology Company
    Inventor: Richard E. Cherpeck
  • Patent number: 5306315
    Abstract: Poly(alkylene ether) amines having the formula: ##STR1## wherein A is an amine moiety having at least one basic nitrogen atom; R.sub.1 is a hydrocarbyl group having a sufficient number of carbon atoms to render the poly(vinyl ether) amine soluble in hydrocarbons boiling in the gasoline or diesel fuel range; R.sub.2 is an alkylene group having 2 to about 8 carbon atoms; R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are each independently hydrogen or a lower alkyl group having 1 to about 4 carbon atoms; R.sub.9 is an alkyl group having 1 to about 10 carbon atoms; m is 0 or 1; and n is an integer from 5 to 99. The poly(vinyl ether) amines of formula I are useful as fuel additives for the prevention and control of engine deposits.
    Type: Grant
    Filed: April 1, 1993
    Date of Patent: April 26, 1994
    Assignee: Chevron Research and Technology Company
    Inventor: Richard E. Cherpeck
  • Patent number: 5112364
    Abstract: Gasolines containing polyetheramine and/or polyetheramine derivatives to improve valve cleaning properties.
    Type: Grant
    Filed: April 29, 1991
    Date of Patent: May 12, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans P. Rath, Helmut Mach, Knut Oppenlaender, Willibald Schoenleben, Hans-Henning Vogel
  • Patent number: 5102427
    Abstract: The present invention provides for a middle distillate fuel having a boiling range within about 120.degree. to about 400.degree. C. which has enhanced low temperature flow properties. These enhanced properties are provided by the addition of a mixture comprising:a) the sulfonamide or amine salt reaction product of an alkylaryl sulfonic acid having from about 10 to about 70 carbon atoms and a primary, secondary tertiary or quaternary amine having from 4 to about 40 carbon atoms;b) an alkyl diphenyl ether wherein the alkyl group contains from about 16 to about 44 carbon atoms; andc) an oil soluble nitrogen-containing compound containing a total of about 30 to about 300 carbon atoms and having at least one straight chain alkyl segment of 8 to 40 carbon atoms and selected from the class consisting of the amine salt and/or amide reaction product of a hydrocarbyl carboxylic acid or anhydride having 1 to 4 carbonyl groups and a primary, secondary, tertiary or quaternary amine having from 4 to about 40 carbon atoms.
    Type: Grant
    Filed: February 8, 1991
    Date of Patent: April 7, 1992
    Assignee: Exxon Research & Engineering Company
    Inventors: Nicholas Feldman, Antonio Gutierrez
  • Patent number: 5042990
    Abstract: Storage-stable, pumpable, concentrated dispersions of coal in water contain a non-ionic additive constituted by a polymer containing polyethoxy chains grafted onto suitably functionalized polystyrenes having a molecular weight comprised within the range of from 500 to 15000.
    Type: Grant
    Filed: November 27, 1989
    Date of Patent: August 27, 1991
    Assignee: Eniricerche S.p.A.-and- Snamprogetti S.p.A.
    Inventors: Fabrizio Bonaccorsi, Aldo Prevedello, Armando Marcotullio, Edoardo Platone, Arnaldo Roggero, Elio Donati
  • Patent number: 5039310
    Abstract: Reaction products in which polyethers are grown from substituted phenol-containing mannich bases have been found to be effective ashless dispersants and detergents for fuels and lubricants.
    Type: Grant
    Filed: December 6, 1988
    Date of Patent: August 13, 1991
    Assignee: Mobil Oil Corporation
    Inventors: David A. Blain, Angeline B. Cardis