Additional Nitrogen Attached Indirectly To The Nitrogen By Acyclic Nonionic Bonding Patents (Class 44/425)
  • Patent number: 10457884
    Abstract: A detergent additive package, fuel additive concentrate, fuel composition and method for operating an engine on an unleaded gasoline fuel. The additive package includes a Mannich base detergent mixture, wherein the mixture contains a first Mannich base detergent component derived from a di- or polyamine and a second Mannich base detergent component derived from a monoamine. A weight ratio of the first Mannich base detergent to the second Mannich base detergent in the mixture ranges from about 1:6 to about 3:1.
    Type: Grant
    Filed: November 6, 2014
    Date of Patent: October 29, 2019
    Assignee: Afton Chemical Corporation
    Inventors: Joseph M. Russo, William Jay Colucci
  • Publication number: 20150121747
    Abstract: This invention relates to a Mannich base, production and use thereof in producing a detergent. The Mannich base is represented by the following formula (III), wherein A and R2 are as defined in the specification. The Mannich base can be used to produce a detergent and a fuel oil composition exhibiting excellent deposit formation suppressing performance and excellent anticorrosion performance.
    Type: Application
    Filed: April 25, 2013
    Publication date: May 7, 2015
    Applicant: CHINA PETROLEUM & CHEMICAL CORPORATION
    Inventors: Shihao Xin, Qinghua Duan, Zuoxin Huang
  • Patent number: 8858658
    Abstract: Biodiesel fuels, renewable diesel fuels and feedstocks to these fuels (derived from plant seed oils or animal fats) are viewed as more environmentally friendly, renewable alternative fuels or supplemental fuels with petroleum-based diesel. Alkyl phenol amine aldehyde condensates improve the stability of biofuels by inhibiting the degradation processes. Alkyl phenylene diamines employed together with alkyl phenol amine aldehyde condensates in the biofuels give synergistically improved stability of the fuels.
    Type: Grant
    Filed: March 21, 2013
    Date of Patent: October 14, 2014
    Assignee: Baker Hughes Incorporated
    Inventors: Timothy J. O'Brien, Brian R. Munson
  • 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: 20130283678
    Abstract: Biodiesel fuels, renewable diesel fuels and feedstocks to these fuels (derived from plant seed oils or animal fats) are viewed as more environmentally friendly, renewable alternative fuels or supplemental fuels with petroleum-based diesel. Alkyl phenol amine aldehyde condensates improve the stability of biofuels by inhibiting the degradation processes. Alkyl phenylene diamines employed together with alkyl phenol amine aldehyde condensates in the biofuels give synergistically improved stability of the fuels.
    Type: Application
    Filed: March 21, 2013
    Publication date: October 31, 2013
    Inventors: Timothy J. O'Brien, Brian R. Munson
  • Patent number: 8540784
    Abstract: The present invention provides hybrid diesel fuels and methods for manufacturing hybrid diesel fuels. In embodiments, fuel compositions comprise at least one petrochemical fuel, at least one biosynthetic oil and at least one stabilizer mixture. The percentage by volume of the petrochemical fuel can be greater than 0% and less than 100%, and the percentage by volume of the stabilizer mixture can be between about 0.001% and about 0.5%.
    Type: Grant
    Filed: April 23, 2010
    Date of Patent: September 24, 2013
    Assignee: Tellus Renewables LLC
    Inventors: Brent Siemssen, Joel Edmonds
  • Patent number: 8425629
    Abstract: An additive composition comprises a Mannich reaction product of a) a polyisobutylene (PIB) alkylated hydroxyaromatic compound, b) an aldehyde, and c) an amine containing at least one reactive amino group where the PIB is derived from a conventional PIB and a high vinylidene PIB. A fuel additive concentrate composition, a fuel composition, and a method to reduce deposit formation in a fuel system of an internal combustion engine employ the additive composition that comprises the Mannich reaction product which is unexpectedly effective in reducing deposits. A PIB alkylated hydroxyaromatic compound, that is prepared from a mixture of high vinylidene and conventional PIBs, is both a functional additive and an intermediate to a functional additive and the process to prepare it involves running the alkylation reaction at 5 to 40° C.
    Type: Grant
    Filed: November 3, 2004
    Date of Patent: April 23, 2013
    Assignee: The Lubrizol Corporation
    Inventors: Mitchell M. Jackson, Jeffry G. Dietz, Mark Davies
  • Publication number: 20110308550
    Abstract: A method of removing deposits from a diesel engine, the method comprising combusting in the engine a diesel fuel composition comprising an engine cleaning additive, wherein the engine cleaning additive is the product of a Mannich reaction between: (a) an aldehyde; (b) ammonia, hydrazine or an amine; and (c) an optionally substituted phenol; wherein the or each substituent of the phenol component (c) has an average molecular weight of less than 400.
    Type: Application
    Filed: February 25, 2010
    Publication date: December 22, 2011
    Applicant: INNOSPEC LIMITED
    Inventor: Jacqueline Reid
  • Publication number: 20100299992
    Abstract: The present invention relates to diesel fuel compositions comprising a performance enhancing additive, wherein the additive is the product of a Mannich reaction between: (a) an aldehyde; (b) a polyamine; and (c) an optionally substituted phenol; wherein the or each substituent of component (c) has an average molecular weight of less than 400.
    Type: Application
    Filed: September 25, 2008
    Publication date: December 2, 2010
    Inventor: Jacqueline Reid
  • Patent number: 6767374
    Abstract: Hydrogenated block copolymers are used as a component in a cold flow additive composition.
    Type: Grant
    Filed: December 31, 1997
    Date of Patent: July 27, 2004
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Dhanesh Gordon Goberdhan, Robert Dryden Tack, Kenneth Lewtas, Andrew Matthew McAleer, Lewis John Fetters, John Huang
  • Publication number: 20030177692
    Abstract: The present invention is directed to a method to clean up or keep clean the fuel system of a direct injection spark-ignited engine by operating the engine with a fuel composition that includes a liquid fuel and a fuel additive composition.
    Type: Application
    Filed: March 12, 2002
    Publication date: September 25, 2003
    Applicant: The Lubrizol Corporation
    Inventors: David C. Arters, Mitchell M. Jackson, Daniel T. Daly, Malcolm G.J. Macduff
  • Publication number: 20030079399
    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): 1
    Type: Application
    Filed: September 14, 2001
    Publication date: May 1, 2003
    Inventors: Dennis J. Malfer, Scott D. Schwab, Timothy J. Henly
  • Publication number: 20030029077
    Abstract: A fuel composition comprises a hydrocarbon fuel, a combination of nitrogen-containing detergents that includes a hydrocarbyl-substituted polyamine and a Mannich reaction product, and optionally a fluidizer. Methods of operating and of controlling deposits in an internal combustion engine involve fueling the engine with the fuel composition which results in unexpectedly effective and efficient control of deposits in the fuel induction system.
    Type: Application
    Filed: August 7, 2001
    Publication date: February 13, 2003
    Applicant: The Lubrizol Corporation, a corporation of the State of Ohio
    Inventors: Mitchell M. Jackson, David C. Arters
  • Patent number: 6090170
    Abstract: The present invention relates to derivatives of polyalkenyl amine substituted with numerous hydroxy groups of the following formula (I) useful as a novel fuel detergent. ##STR1## wherein polyalkenyl denotes a branched alkyl derived from polyolefin which has a molecular weight of 400.about.5,000 and is prepared with olefin having 2 to 6 carbon atoms; m is an integer ranging from 2 to 10, R.sup.1, R.sup.2 and R.sup.3 may be identical or different, and represent a hydrogen atom or a linear or branched alkyl having 1 to 4 carbon atoms: R.sup.4 and R.sup.5 may be identical or different, and denote a hydrogen atom, a C.sub.1 -C.sub.10 alkyl group, a hydroxyalkyl, a phenyl, naphthyl, an aminoalkyl of formula (II) or a polyaminoalkylene of formula (III) ##STR2## wherein R.sup.6 denotes a C.sub.2 -C.sub.10 alkylene group: R.sup.7 and R.sup.8 may be identical or different, and denote a hydrogen atom, a C.sub.1 -C.sub.10 alkyl group, a phenyl, a naphthyl or a C.sub.1 -C.sub.
    Type: Grant
    Filed: December 31, 1998
    Date of Patent: July 18, 2000
    Assignee: Daelim Industrial Co., Ltd.
    Inventors: Hyun-ki Yun, Jung-jin Kim, Yong-hwa Yeom, Il-seung Kim, Myeong-seog Kim, Byung-keel Sohn, Kyu-shon Jung
  • Patent number: 6080213
    Abstract: A stabilized aqueous solution of a diazo compound has the formula: ##STR1## where X.sup.1 is selected from nitro and chloro, X.sup.2 is selected from nitro, chloro and hydrogen, and Y is an acid-derived anion. The solution has a pH of about 1.5 or below and a diazo concentration of about 2 wt % or less. The solution is useful as an extractant/developer for petroleum fuel markers.
    Type: Grant
    Filed: September 9, 1998
    Date of Patent: June 27, 2000
    Assignee: Morton International, Inc.
    Inventor: Al Zimin, Sr.
  • 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: 5833721
    Abstract: An antifoam additive for hydrocarbon oils and in particular fuel oils comprises the combination of an antifoam agent and an ashless dispersant.
    Type: Grant
    Filed: February 14, 1997
    Date of Patent: November 10, 1998
    Assignee: Exxon Chemical Patents Inc
    Inventors: Richard Joseph Hart, Rinaldo Caprotti
  • 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: 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: 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: 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: 5167671
    Abstract: The low-temperature properties of distillate fuels are improved when reaction products of pyromellitic dianhydride and amonoalcohols and/or amines with long chain hydrocarbyl groups are incorporated therein.
    Type: Grant
    Filed: December 3, 1990
    Date of Patent: December 1, 1992
    Assignee: Mobil Oil Corporation
    Inventors: David J. Baillargeon, Angeline B. Cardis, Dale B. Heck
  • Patent number: 5129917
    Abstract: The reaction product of certain epoxy resins and secondary amines improve the low-temperature properties of distillate fuels.
    Type: Grant
    Filed: December 3, 1990
    Date of Patent: July 14, 1992
    Assignee: Mobil Oil Corporation
    Inventors: David J. Baillargeon, Angeline B. Cardis, Susan W. Johnson
  • Patent number: 5047069
    Abstract: An antioxidant for liquid hydrocarbons such as fuels has the structure ##STR1## wherein X is N or S; R is H or a C.sub.1 to C.sub.5 alkyl moiety; R.sup.1 and R.sup.2 are each independently C.sub.5 to C.sub.18 alkyl or cycloalkyl moieties (which may optionally contain a hetero atom such as oxygen), only one of R.sup.1 and R.sup.2 being present if X is S, or may be combined to form a 5 or preferably 6 membered ring; each R.sup.6 is independently the residue of a C.sub.1 to C.sub.5 aldehyde; and R.sup.7 is the residue of a polyamine of the formula ##STR2## wherein R.sup.3 is a C.sub.8 to C.sub.50 alkyl moiety (which may optionally contain one or more ether linkages); R.sup.4 and R.sup.5 are each independently C.sub.2 to C.sub.6 alkylene moieties; a is 0 or 1; and m is at least 3.
    Type: Grant
    Filed: October 22, 1990
    Date of Patent: September 10, 1991
    Assignee: Petrolite Corporation
    Inventors: Jerry J. Weers, Thomas V. Bagwell
  • 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