Substituent On The Ring Nitrogen Contains An Acyclic -c(=x)- Group, Wherein X Is Chalcogen Patents (Class 44/348)
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Patent number: 10865358Abstract: The present invention is directed to a use of a lubricant in a diesel engine to disperse soot produced by the diesel engine, the soot being dispersed without adversely affecting the viscosity of the lubricant; the lubricant comprising a major amount of oil of lubricating viscosity and a minor amount of a dispersant comprising (i) one or more olefin, (ii) one or more carboxylic acid, (iii) one or more polyetheramines and (iv) one or more aromatic amines along with co-additives.Type: GrantFiled: January 24, 2019Date of Patent: December 15, 2020Assignee: Jinzhou DPF-TH Chemicals Co., Ltd.Inventors: Jun Hua, Yantao Zhu, Xiao Wei, Rolfe Hartley, Ricardo Bloch, Yuan Gao
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Patent number: 8734542Abstract: The invention relates to the use of at least one oil-soluble compound B) which acts as a nucleating agent for paraffin crystallization and which is selected from ethylene copolymers and 2 to 10.5 mole % of at least one ethylenically unsaturated carbonic ester for improving the response of cold flow improvers for mineral oils C), which are different from B), in middle distillates that contain at least one ashless, nitrogenous detergent additive A), which is an oil-soluble, amphiphilic compound that comprises at least one alkyl or alkenyl group bound to a polar group, said alkyl or alkenyl group having 10 to 500 C atoms and the polar group having 2 or more nitrogen atoms.Type: GrantFiled: June 17, 2008Date of Patent: May 27, 2014Assignee: Clariant Finance (BVI) LimitedInventors: Matthias Krull, Robert Janssen
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Publication number: 20130276362Abstract: The present invention relates to the use of additives with detergent action selected from: (i) compounds with moieties derived from succinic anhydride and having hydroxyl and/or amino and/or amido and/or imido groups; (ii) nitrogen compounds quaternized in an acid-free manner, obtainable by addition of a compound comprising an oxygen- or nitrogen-containing group reactive with an anhydride and additionally a quaternizable amino group onto a polycarboxylic anhydride compound and subsequent quaternization; (iii) polytetrahydrobenzoxazines and bistetrahydrobenzoxazines for further increasing the cetane number of fuel oils which comprise cetane number improvers; furthermore, it relates to a fuel additive concentrate consisting of additives (i) to (iii), cetane number improvers, organic diluents or solvents and possibly customary co-additives.Type: ApplicationFiled: April 19, 2013Publication date: October 24, 2013Applicant: BASF SEInventor: Harald BOEHNKE
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Publication number: 20120264662Abstract: This invention relates to functionalized monomers. The functionalized monomer may be reacted with an enophilic reagent (e.g., maleic anhydride) to form an enophilic reagent modified functionalized monomer. The invention relates to lubricants, functional fluids, fuels, dispersants, detergents, functional compositions (e.g., food products, cleaners, etc.), and the like.Type: ApplicationFiled: March 23, 2012Publication date: October 18, 2012Inventors: Stephen A. DiBiase, Syed Q.A. Rizvi, Georgeta Hategan
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Publication number: 20080256849Abstract: The disclosure provides conductivity improving concentrates and methods for improving conductivity and reducing risks associated with static discharge in middle distillate fuel compositions, particularly diesel fuels. The conductivity improvement is provided by the combination of a detergent and a cold flow improver, which are preferably and advantageously pre-blended in an additive concentrate. The disclosure is particularly beneficial for ultra-low sulfur fuel compositions in that it provides a conductivity benefit without adding sulfur into the fuel composition.Type: ApplicationFiled: April 19, 2007Publication date: October 23, 2008Inventors: Alexander M. Kulinowski, Timothy J. Brennan
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Publication number: 20080256848Abstract: The disclosure provides conductivity improving concentrates and methods for improving conductivity and reducing risks associated with static discharge in middle distillate fuel compositions, particularly ultra-low sulfur diesel fuels. The conductivity improvement is provided in the presence of a basic nitrogen component and is sustained for an extended period, thus permitting the antistatic agent to be pre-blended with in an additive concentrate or to the fuel well in advance of the time when the improved conductivity might actually be needed, such as when the fuel is dispensed into a bulk container.Type: ApplicationFiled: April 19, 2007Publication date: October 23, 2008Inventors: Timothy J. Brennan, Alexander M. Kulinowski
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Patent number: 7175678Abstract: 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: GrantFiled: September 26, 2003Date of Patent: February 13, 2007Assignee: Innospec LimitedInventors: Cyrus Pershing Henry, David Leonard Pinch, Andrea Sneddon, Derek Richard Green
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Patent number: 6867171Abstract: This invention is directed to a new low molecular weight branched alkenyl succinic acid derivative that may be prepared by reacting a low molecular weight polyisobutene (PIB) having from about 8 to about 32 carbon atoms, and wherein at least about 50% of the olefinic bonds of the polyisobutene comprises methylvinylidene isomer plus tri-substituted isomer, with an unsaturated acidic reagent and method of making same, resulting in alkenyl succinic acid derivative isomers; and a low molecular weight branched alkenyl succinimide and method of making same.Type: GrantFiled: November 27, 2002Date of Patent: March 15, 2005Assignee: Chevron Oronitz Company LLCInventors: James J. Harrison, Kenneth Nelson
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Patent number: 6821307Abstract: An improved fuel oil composition comprises fuel oil and specific acylated polyalkylene polyamine.Type: GrantFiled: December 18, 2002Date of Patent: November 23, 2004Assignee: Infineum International Ltd.Inventors: Rinaldo Caprotti, Christophe Ledeore
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Patent number: 6733550Abstract: The invention provides a fuel oil composition comprising a major proportion of liquid hydrocarbon middle distillate fuel oil having a sulphur concentration of at most 0.05% by weight, and a minor proportion of a dispersant additive obtained by reacting, in a molar ratio A:B in the range 4:3 to 1:10, (A) a polyalkenyl derivative of monoethylenically unsaturated C4-C10 dicarboxylic acid material in which the number average molecular weight (Mn) of the polyalkenyl chain is in the range from 850 to 1150 with (B) a polyamine of general formula H2N(CH2)m—[NH(CH2)m]n—NH2 (1) where m is in the range from 2 to 4 and n is in the range from 1 to 6; a process for the preparation of such a fuel composition, and a method of operation a compression-ignition engine with enhance injector cleanliness using such a fuel oil composition.Type: GrantFiled: March 18, 1998Date of Patent: May 11, 2004Assignee: Shell Oil CompanyInventors: Michael John Grundy, Michael Pearson
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Patent number: 6548458Abstract: Succinimide-acid compounds prepared by reaction of hydrocarbyl-substituted succinic acylating agents with alpha-omega amino acids are disclosed, as well as derivatives thereof useful as lubricity additives, lubricant dispersants, friction modifiers, liquid hydrocarbonaceous fuel detergents, antioxidants and alkali and/or alkaline-earth metal detergents.Type: GrantFiled: November 8, 2001Date of Patent: April 15, 2003Assignee: Ethyl CorporationInventor: John T. Loper
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Patent number: 6458172Abstract: The present invention is directed to fuel additive compositions of detergents combined with fluidizers and to hydrocarbon fuel compositions containing these fuel additive compositions. The fuel additive compositions of the present invention combine a Mannich detergent, formed from reaction of an alkylphenol with an aldehyde and an amine, with a fluidizer that can be a polyetheramine or a polyether or a mixture thereof and, optionally, with a succinimide detergent. Fuel compositions containing these fuel additive compositions are very effective in reducing intake valve deposits in gasoline fueled engines, especially when the weight ratio of detergent(s) to fluidizer(s) is about 1:1 on an actives basis.Type: GrantFiled: March 3, 2000Date of Patent: October 1, 2002Assignee: The Lubrizol CorporationInventors: Malcolm G. J. Macduff, Mitchell M. Jackson, David C. Arters, Rodney J. McAtee
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Publication number: 20020091068Abstract: Succinimide-acid compounds prepared by reaction of hydrocarbyl-substituted succinic acylating agents with alpha-omega amino acids are disclosed, as well as derivatives thereof useful as lubricity additives, lubricant dispersants, friction modifiers, liquid hydrocarbonaceous fuel detergents, antioxidants and alkali and/or alkaline-earth metal detergents.Type: ApplicationFiled: November 8, 2001Publication date: July 11, 2002Inventor: John T. Loper
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Publication number: 20020053160Abstract: A middle petroleum distillate composition containing a major proportion of middle petroleum distillate and a minor proportion of an additive in a sufficient amount to limit the settling speed of paraffins contained in said middle distillate. Said additive consists of a product resulting from a reaction between at least one aliphatic dicarboxylic compound and at least one primary amine functional compound of general formula (I), wherein R1 is a monovalent saturated aliphatic radical, Z is selected from —NR′— groupings in which R′ is a hydrogen atom or a monovalent saturated aliphatic radical, n is an integer between 2 and 4, and m is an integer between I and 4; said primary amine functional compound being used in a ratio of 0.3-0.8 mols per mol of said dicarboxylic compound.Type: ApplicationFiled: September 26, 2001Publication date: May 9, 2002Applicant: Institut Francais du PetroleInventors: Despina Vassilakis, Robert Leger, Alain Forestiere, Jean Gaillard
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Patent number: 6083287Abstract: The invention concerns a detergent and anti-corrosive additive for engine fuels, in particular gas oil, containing amide or imide functions characterised in that it is obtained by mixing wt. 60 to 90% of a compound A consisting of at least one carboxylic polyalkenyl, diacid or anhydride, of average molecular mass between 200 and 3000, wt. 0.1 to 10% of a compound B consisting of at least one carboxylic compound, monoacid or anhydride, containing 1 to 6 carbon atoms per chain and 10 to 30% of a compound C consisting of at least one primary polyamine of general formula H.sub.2 N--[--(CHR.sub.1 --(CH.sub.2).sub.p --CHR.sub.2).sub.n --NH].sub.m --H, the mol ratios A/B/C corresponding to 1/(0.1 to 1)/(1 to 3), A/B/C never being 1/1/1.Type: GrantFiled: June 16, 1999Date of Patent: July 4, 2000Assignee: Elf Antar FranceInventors: Laurent Germanaud, Guy Raoult, Daniele Eber
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Patent number: 5993497Abstract: Esters of polyalkyl or polyalkenyl N hydroxyalkyl succinimides having the formula: ##STR1## or a fuel soluble salt thereof; wherein R is a polyalkyl or polyalkenyl group having an average molecular weight in the range of about 450 to about 5,000;n is an integer from 2 to 5; and Z is a moiety selected from the group consisting of ##STR2## wherein R.sub.1 is a hydroxy, nitro, cyano or --(CH.sub.2).sub.x --NR.sub.3 R.sub.4, wherein R.sub.3 and R.sub.4 are independently hydrogen or lower alkyl of 1 to 6 carbon atoms and x is 0 or 1; and R.sub.2 is hydrogen, hydroxy, nitro, cyano or --(CH.sub.2).sub.y --NR.sub.5 R.sub.6, wherein R.sub.5 and R.sub.6 are independently hydrogen or lower alkyl of 1 to 6 carbon atoms and y is 0 or 1.The compounds of formula I are useful as fuel additives for the prevention and control of engine deposits.Type: GrantFiled: August 28, 1998Date of Patent: November 30, 1999Assignee: Chevron Chemical Company LLCInventors: Richard E. Cherpeck, Kenneth D. Nelson
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Patent number: 5954843Abstract: Aminocarbamates of polyalkyl or polyalkenyl N-hydroxyalkyl succinimides having the formula: ##STR1## or a fuel soluble salt thereof; wherein R is a polyalkyl or polyalkenyl group having an average molecular weight in the range of about 450 to about 5,000;n is an integer from 2 to 5; andA is a polyamine moiety having at least one basic nitrogen atom, wherein the polyamine is connected to he carbonyl group through one of its nitrogen atoms to form a carbamate linkage.The compounds of formula I are useful as fuel additives for the prevention and control of engine deposits.Type: GrantFiled: August 28, 1998Date of Patent: September 21, 1999Assignee: Chevron Chemical Company LLCInventor: Richard E. Cherpeck
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Patent number: 5620486Abstract: A fuel composition comprising a major amount of hydrocarbons boiling in the gasoline or diesel range and an effective detergent amount of a compound of the formula: ##STR1## wherein R is a hydrocarbyl group having an average molecular weight of about 400 to 5,000; andR.sub.1 and R.sub.2 are independently selected from the group consisting of hydrogen, hydroxy, --CO.sub.2 H, --NO.sub.2, and --NR.sub.3 R.sub.4, wherein R.sub.3 and R.sub.4 are independently hydrogen or lower alkyl of 1 to 6 carbon atoms; provided that R.sub.1 and R.sub.2 cannot both be hydrogen.Type: GrantFiled: December 30, 1994Date of Patent: April 15, 1997Assignee: Chevron Chemical CompanyInventor: Richard E. Cherpeck
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Patent number: 5601624Abstract: Oxygenated alkyl amines synthesized using carbonyl coupling reactions have combustion chamber deposit reducing properties and oxidative stability characteristics beneficial for dispersant/detergent applications in fuels and lubricants.Type: GrantFiled: April 10, 1995Date of Patent: February 11, 1997Assignee: Mobil Oil CorporationInventors: James T. Carey, John Hiebert, Andrew G. Horodysky
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Patent number: 5476521Abstract: The present invention is directed to a fuel additive comprising at least one adduct of (A) a polyolefin of 300 to 10,000 number average molecular weight substituted with at least 0.3 (e.g., from about 1 to 4) mono- or dicarboxylic acid producing moieties (preferably acid or anhydride moieties) per polyolefin molecule, (B) an amido-amine or thioamido-amine characterized by being a reaction product of at least a polyamine and an alpha, beta-unsaturated compound of the formula: ##STR1## wherein X is sulfur or oxygen, Y is --OR.sup.4, --SR.sup.4, or --NR.sup.4 (R.sup.5), and R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are the same or different and are hydrogen or substituted or unsubstituted hydrocarbyl.Type: GrantFiled: November 4, 1994Date of Patent: December 19, 1995Assignee: Exxon Chemical Patents Inc.Inventors: Antonio Gutierrez, Robert D. Lundberg
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Patent number: 5468262Abstract: A liquid jet fuel composition comprising:(a) a major portion of a liquid fuel; and(b) a minor effective portion of a thermal stabilizing additive prepared by(i) reacting a polyamine, an aldehyde and a phenol containing active hydrogen to form a phenol - aldehyde - amine condensate; and(ii) reacting said phenol - aldehyde - amine condensate and a succinic acid anhydride bearing a polyolefin - derived substituent containing residual unsaturation, thereby forming a phenol - aldehyde amine Mannich condensate polyamine succinimide product additive; and(iii) recovering said product additive.Type: GrantFiled: April 19, 1993Date of Patent: November 21, 1995Assignee: Texaco Inc.Inventors: William P. Acker, Robert T. Hahn, Thomas J. Mach, Rodney L. Sung
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Patent number: 5425788Abstract: An additive composition for fuels comprising at least one constituent (A) and at least one constituent (B), the said constituent (A) comprising at least one multinitrogen-containing compound of general formula (I): ##STR1## where R.sup.1 and R.sup.2, which are the same or different each represent a hydrocarbon group or a group of formula R.sup.5 --(--O--R.sup.6 --).sub.a --(--O--R.sup.7 --).sub.b --, R.sup.3 is a hydrocarbon group or a group of formula R.sup.8 --(--X--R.sup.9 --).sub.c --(--X--R.sup.1 O--).sub.d --(--X--R.sup.1 1--).sub.e -- in which X is selected from the groups --O-- and --NR.sup.1 2--, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.1 0 and R.sup.1 1 each represent a hydrocarbon group, a, d and e are each zero or a whole number, b and c are each a whole number, R.sup.4 and R.sup.1 2 each represent a hydrogen atom or a hydrocarbon group and n is a number from 0 to 20 and the said constituent (B) comprises at least one polyglycol which is soluble in the fuel in question.Type: GrantFiled: November 4, 1993Date of Patent: June 20, 1995Assignees: Institut Francais du Petrole, Elf Antar FranceInventors: Jacques Garapon, Alain Forestiere, Philippe Mulard, Yvan Labruyere
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Patent number: 5308364Abstract: The present invention is directed to fuel compositions containing branched amido-amine additives formed by (a) reacting a first nitrogen-containing compound (e.g., ammonia or an organic amine) with an alpha, beta-unsaturated compound of the formula: ##STR1## wherein W.sup.1 is sulfur or oxygen, Y is --OR.sup.4, --SR.sup.4, or --NR.sup.4 (R.sup.5), and R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are the same or different and are hydrogen or substituted or unsubstituted hydrocarbyl, to form a first adduct containing unreacted --C(W.sup.1)--Y groups; (b) reacting the first adduct with a polyamine (e.g., a polyalkylene polyamine) to form a second adduct containing unreacted --NH-- group (preferably primary amine groups) and comprising a branched amido-amine oligomer; and (c) reacting the second adduct with a long chain hydrocarbyl substituted mono- or dicarboxylic acid material comprising a polyolefin of 300 to 10,000 number average molecular weight substituted with at least 0.Type: GrantFiled: July 14, 1993Date of Patent: May 3, 1994Assignee: Exxon Chemical Patents Inc.Inventors: Antonio Gutierrez, Robert D. Lundberg
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Patent number: 5266081Abstract: A fuel additive is the reaction product of an intermediate reaction product of a hydrocarbon-substituted succinic anhydride and an aminosalicylic acid, preferably a 4-aminosalicylic acid. The intermediate is reacted with an aldehyde, preferably formaldehyde and an alkylenepolyamine preferably tetraethylenepentamine. The reaction product is post reacted with a hydrocarbon-substituted succinic anhydride which can be the same or different as the hydrocarbon-substituted succinic anhydride of the intermediate. The additive has dispersant and detergent properties and is effective in liquid hydrocarbon or liquid oxygenated fuels or mixtures of the said fuels.Type: GrantFiled: October 18, 1991Date of Patent: November 30, 1993Assignee: Mobil Oil CorporationInventors: Noyes L. Avery, Angeline B. Cardis, James V. DeFrancesco, Virginia C. Wiszniewski
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Patent number: 5234476Abstract: Polynitrogen compound having two terminal cycles of the imide type, its preparation by conventional organic chemistry methods and its use as an additive for engine fuel. This compound complies with the general formula (I): ##STR1## in which R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are as set forth in the specification.Type: GrantFiled: July 30, 1992Date of Patent: August 10, 1993Assignees: Institut Francais du Petrole, Elf FranceInventors: Jacques Garapon, Roger Bregent, Remi Touet, Philippe Mulard, Pierre Schmelzle
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Patent number: 5122161Abstract: A diesel fuel composition comprising:(a) a major portion of a diesel fuel, and(b) a minor amount, as a diesel fuel injector detergent, of a glycolated Mannich coupled product of bis-polyisobutylene succinimide of a polyamine, prepared by:(i) reacting an alkenylsuccinic acid anhydride with a polyamine to form a bis-succinimide;(ii) treating the bis-succinimide with a phenol in the presence of an aldehyde to form a Mannich phenol coupled bis-succinimide product;(iii) glycolating the Mannich phenol coupled bis-succinimide product with glycolic acid to form a glycolated Mannich phenol coupled bis-succinimide product; and(iv) recovering the glycolated Mannich phenol coupled bis-succinimide product.Type: GrantFiled: December 31, 1990Date of Patent: June 16, 1992Assignee: Texaco Inc.Inventors: Nicholas Benfaremo, Kashmir S. Virk, Sheldon Herbstman
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Patent number: 5114435Abstract: Deposits on intake valves in gasoline internal combustion engines are reduced by an additive for fuel compositions comprising a mixture of (1) a polyalkylene succinimide, (2) a polyalkylene and (3) a mineral oil. The invention also comprises a fuel composition made up of a major amount of liquid hydrocarbon fuel such as gasoline or diesel and a minor amount of the aforesaid mixture. In still another aspect the invention comprises a method for removing and/or preventing engine deposits which adversely affect the performance of gasoline powered engines by running the engine with a fuel containing an effective amount of the previously described mixture.Type: GrantFiled: February 20, 1990Date of Patent: May 19, 1992Assignee: Mobil Oil CorporationInventors: Guy P. Abramo, Jeffrey C. Trewella
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Patent number: 5039307Abstract: A diesel fuel composition comprising:(a) a major portion of a diesel fuel, and(b) a minor amount, as a diesel fuel injector detergent additive, of a Mannich coupled product of bis-polyisobutylene succinimide of an amine, prepared by:(i) reacting an alkenyl succinimide acid anhydride with an amine to form a bis-succinimide;(ii) treating the bis-succinimide with nonylphenol in the presence of an aldehyde to form a Mannich phenol coupled bis-succinimide product; and(iii) recovering the product Mannich phenol coupled bis-succinimide.Type: GrantFiled: October 1, 1990Date of Patent: August 13, 1991Assignee: Texaco Inc.Inventors: Sheldon Herbstman, Kashmir S. Virk, Theodore E. Nalesnik, Nicholas Benfaremo
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Patent number: 5030249Abstract: A gasoline composition comprising:(a) a major portion of a gasoline fuel, and(b) a minor amount, as a gasoline detergent additive, of a Mannich coupled product of bis-polyisobutylene succinimide of an amine, prepared by:(i) reacting an alkenyl succinimide acid anhydride with an amine to form a bis-succinimide;(ii) treating the bis-succinimide with nonylphenol in the presence of an aldehyde to form a Mannich phenol coupled bis-succinimide product; and(iii) recovering the product Mannich phenol coupled bis-succinimide.Type: GrantFiled: October 1, 1990Date of Patent: July 9, 1991Assignee: Texaco Inc.Inventors: Sheldon Herbstman, Thomas E. Hayden, Theodore E. Nalesnik, Nicholas Benfaremo
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Patent number: 5024678Abstract: Process for the prevention of reduction of deposits in carburetors, injection devices or similar devices of engines, which are operated with alcohol fuels comprising 99.9 to 75 Vol.-% methanol, ethanol or a mixture thereof and at least one corrosion inhibitor characterized in that one or several polyol ethers are added to the alcohol fuels in a quantity of 15 ppm up to 1 weight-%, whereby the polyol ether(s) has (have) the general formula ##STR1## wherein R is H, linear or branched C.sub.1 -C.sub.20 -alkyl, C.sub.1 -C.sub.20 -alkenyl, polyunsaturated C.sub.1 -C.sub.20 - alkyl, C.sub.1 -C.sub.20 - cycloalkyl, mono- or bicyclo-C.sub.6 -C.sub.14 -aryl, unsubstituted or substituted, R.sub.1 is H, C.sub.1 -C.sub.8 -alkyl, unsubstituted or substituted aryl, R.sub.2 is H, C.sub.1 -C.sub.8 -alkyl, unsubstituted or substituted aryl, and R.sub.3 is OR.sub.5, SR.sub.5, N(R.sub.5).sub.2, wherein R.sub.5 is H, linear or branched C.sub.1 -C.sub.20 -alkyl, C.sub.1 -C.sub.20 -cycloalkyl, mono- and bicyclo-C.sub.6 -C.sub.Type: GrantFiled: April 5, 1988Date of Patent: June 18, 1991Assignee: DEA Mineralol AktiengesellschaftInventors: Dagmar Mertens-Gottselig, Hartmut Hammer, Heinrich Muller, Manfred Wildersohn
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Patent number: 4971598Abstract: An additive for fuel compositions. The additive comprises the reaction product of an alkenyl succinimide selected from the group consisting of mono-succinimides, bis-succinimides, and mixtures thereof, with iminodiacetic acid or an ethylenediamine carboxy acid. The reaction product finds particular utility as a fuel detergent.Type: GrantFiled: March 22, 1990Date of Patent: November 20, 1990Assignee: Mobil Oil CorporationInventors: Harry J. Andress, Henry H. Ashjian, Frederick J. Hills