US3260671A - Amide oxidation inhibitor for lubricants - Google Patents
Amide oxidation inhibitor for lubricants Download PDFInfo
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- US3260671A US3260671A US239812A US23981262A US3260671A US 3260671 A US3260671 A US 3260671A US 239812 A US239812 A US 239812A US 23981262 A US23981262 A US 23981262A US 3260671 A US3260671 A US 3260671A
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- amide
- amine
- acid
- lubricant
- acids
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/16—Amides; Imides
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- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
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- C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
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- C10M2207/304—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids derived from the combination of monohydroxy compounds, dihydroxy compounds and dicarboxylic acids only and having no free hydroxy or carboxyl groups
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- C10M2209/107—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of two or more specified different alkylene oxides covered by groups C10M2209/104 - C10M2209/106
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- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
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- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
- C10M2215/064—Di- and triaryl amines
- C10M2215/065—Phenyl-Naphthyl amines
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- C10M2219/108—Phenothiazine
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- C10N2030/08—Resistance to extreme temperature
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Definitions
- This invention relates to a novel composition which is particularly effective when used as an oxidation inhibitor in a jet engine lubricant.
- the invention relates to compounds comprising amides of the type formed by reacting a higher aliphatic, saturated, branched chain monocarboxylic acid with an amine containing both a tertiary as well as a primary amine group.
- the invention also relates to various lubricant compositions containing said amides.
- Oxidation inhibitors are added to lubricant fluids to minimize oxidative decomposition of the fluid to acid products which tend to form sludge and to corrode the various metal surfaces with which the lubricant comes into contact.
- This service demand imposed on the oxidation inhibitor increases rapidly with engine temperatures.
- many of the agents which give adequate protection at temper increasing such as 300 F. have substantially no utility at higher temperatures.
- the lubrication of the gas turbine engines utilized in aircraft propulsion is an excellent illustration of this point.
- the commercial aircraft gas turbine power plant was operated at approximately 300 F. maximum temperature, using a petroleum lubricant and a classic oxidation inhibitor such as an alkylated phenol.
- the gas turbine engines have been designed for higher performance ratings. This has necessitated raising the operating temperatures from 300 F. to 350 F., then 400 F., and now to designs which require lubricant stability up to 450 F.
- the classic oxidation inhibitors fail to perform the required function.
- a further object is to provide a material of this character which is readily soluble in both hydrocarbon as Well as synthetic lubricants, and which does not appreciably affect the liquidous characteristics of the base fluid.
- a still further object is to provide stable lubricant compositions which can be employed with good results at temperatures of from about 300 to 450 F. or even higher.
- R represents a C C, alkyl radical such as methyl, ethyl, propyl, butyl or isobutyl
- R represents a branched chain, saturated aliphatic hydrocarbon group of from about 15 to 24 carbon atoms, this group being, in effect, the hydrocarbyl or non-carboxy portion of a normally liquid, branched chain, saturated, aliphatic monocarboxylic acid containing from about 16 to 25 carbon atoms
- R is a radical selected from the group consisting of those represented by R in the above formula and by the portion of said formula.
- the amide oxidation inhibitors of this invention have unusually good solubility characteristics and are miscible in all proportions with ester type lubricants, polyglycol lubricants and petroleum base oils without appreciably affecting the liquidous range of the base lubricant. Further, these amide additives are highly stable and are adapted to be employed with any of the conventional additives Which are used in formulating a lubricant intended for high temperature service.
- the amide compounds disclosed herein are prepared in conventional fashion by heating together stoichiometrically equivalent amounts of the carboxylic acid and amine reactants, as hereinafter defined. Preferably an excess of the amine is used, the better to drive the reaction to completion, with any excess amine then being stripped from the finished reaction mixture.
- This amidation step which is conducted at temperatures of about to 225 C. until the reaction is complete as indicated by the evolution of the theoretical amount of water of reaction, is preferably carried out in the presence of a suitable solvent such as xylene or toluene which forms an azeotrope with the evolved water.
- the reaction mixture is given a final stripping in vacuo to remove any remaining solvent and excess amine.
- the residual amide is substantially neutral and typically has an acid value of less than 2.
- one mole of a C saturated, branched chain, monocarboxylic fatty acid is reacted with 1.2 moles of an amine such as N,N-dimethylaminopropyl amine to form the amide.
- an amine such as N,N-dimethylaminopropyl amine
- the amine reactant to be one such as N-methyl-bi-s(aminopropyl) amine, which contains two primary amino groups, then 2 moles of the acid would have been employed along with about 1.2 moles of the amine.
- the excess of the amine utilized in the preparation normally ranges from about 5 to 30% for optimum results.
- the monocarboxylic acid employed to form the amide is, as stated above, one which contains from about 16 to 25 carbon atoms and has a branched chain structure. Acids of this character are conventionally liquid at room temperatures and are prepared by synthetic methods. A typical acid adapted to be used in the preparation of the present amides is one containing 18 carbon atoms which is formed from a by-product obtained on polymerizing naturally occurring unsaturated fatty acids in accordance with the method described in U.S. Patent No. 2,812,342. According to the disclosure of said patent, monounsaturated or polyunsaturated fatty acids are treated thermally in the presence of water with or without a catalyst or clay to produce products which are known commercially as dimer acids.
- This process inherently produces a substantial amount of by-product which is a mixture of monomeric acids.
- This monomer mixture which is normally distilled in vacuo from the polymer-containing reaction product, includes saturated fatty acids which have not been affected by the polymerization treatment, probably some unsaturated fatty acids which have not been affected by the polymerization treatment and fatty acids which have been structurally modified by the polymerization treatment in such a manner that they resist further polymerization.
- the recovered mixture of monomeric fatty acids is hydrogenated to reduce the iodine value of the mixture to a level below 10 and perhaps as low as 3, thereby reducing any natural unsaturated fatty acids which may be present to saturated fatty acids.
- the hydrogenation treatment also reduces the iodine value of the fatty acids. which have been structurally modified in some degree by the polymerization treatment. It is difficult to estimate the additional degree of structural modification, if any, which takes place during hydrogenation.
- the hydrogenated fatty acid mixture is then solvent separated to remove solid fatty acids such as stearic and palmiti-c acids.
- the remaining saturated fatty acids are all structurally modified products which, While containing 18 carbon atoms, possess a branched chain structure, a titre below 15 C., and an iodine value of substantially 3 to 10.
- Patent No. 2,812,342 refers to the C fatty acids in question as structurally modified acids (which they are in relation to the starting materials), these acids are more aptly described as structurally stabilized acids.
- these acids have already received two very severe treatments, one a polymerization treatment which tends both to polymerize and to modify structurally the unsaturated acids, and the other a hydrogenation treatment which saturates and perhaps further modifies the structure of the acids.
- these structurally modified acids have become stabilized acids in the sense that they have been subjected to such rigorous treatment as to have developed their most stable structural form.
- Another normally liquid monocarboxylic acid which can be employed is that which contains 22 carbon atoms and is prepared by the polymerization of isobutylene with oleic acid.
- the resulting product on being hydrogenated to effect saturation thereof, will consist essentially of a mixture of 9- and l-sec.-butylstearic acids.
- Still other normally liquid acids falling within the perimeter described for the monocarboxylic acid reactant will suggest themselves to those skilled in the art, e.g., 9-n-octylmargaric acid and IO-methylstearic acid, to name but .a few.
- Typical amine reactants which can be used to prepare the amide anti-oxidant hereof include the following:
- the preferred acid reactant is the described C isostearic acid. Accordinglly, the preferred amideoxidation inhibitor is the resultant reaction product. N,N-dimethyl-isostearamidopropyl amine, Whose preparation is described in Example 1.
- the amide anti-oxidants of this invention can be employed with good effect in connection with a wide variety of lubricant base stocks.
- the latter stock may be one of natural origin such as a highly refined or superrefined mineral oil, or it may be a synthetically prepared stock such as an ester or a polyglycol.
- the amides hereof can be used with any one or more of the wide variety of aliphatic, carboxylic acid esters which have been proposed for lubricant usage. Included in this group are the dialkyl (C C esters of aliphatic dicarboxylic acids (C c the principal diesters being those derived from adipic, azelaic or sebacic acid and a C to C10 alcohol.
- C C esters of aliphatic dicarboxylic acids C c the principal diesters being those derived from adipic, azelaic or sebacic acid and a C to C10 alcohol.
- dialkyl esters of aliphatic dicarboxylic acids are di-isooctyl azelate, di-Z-ethylhexyl sebacate, -di-2-ethylhexyl adipate, dilauryl azelate, di-secamyl sebacate, di-'2-ethylhexyl alkenylsuccinate, di-2- ethoxyethy-l sebacate, di-2(2'-methoxyethoxy) ethyl sebacate, di-2-(2'-ethylbutoxy) ethyl sebacate, di-Z-ethylhexyl azelate, di-2-(2'- butoxyethoxy) ethyl alkenylsuccinate, etc.
- polyester lubricants formed by a reaction of an aliphatic dicarboxylic acid, a glycol and a monofunctional compound, which is either an aliphatic monohydroxy alcohol or an aliphatic monocarboxylic acid, in specified mol ratios are also employed as the synthetic lubricating base.
- Polyesters formed by reaction of a monocarboxylic acid and a glycol may also be used as the ester component.
- the acid component is usually as aliphatic acid containing at least 6 carbon atoms.
- the glycol component can be a straight glycol such as 1,6-hexanediol, but ether glycols such as tetraethylene glycol or dipropylene glycol may also be used.
- diesters of glycols are the following: di-n-decanoate of l,44blutanediol, di-2-ethylhexanoate of 1,6-hexanediol, dilaurate of l,4-hexanediol, di-octanoate of 1,5-pentanediol, dilaurate of tetraethylene glycol, 'dilaurate of triethylene glycol, dioctoate of pentaethylene glycol and dipelargonate of dipropylene glycol.
- I Esters formed by reacting trimethylol alkanes (C -C with various monobasic acids, primarily C -C acids, comprise another example of esters useful for the base fluid of the lubricants of this invention.
- the amount of amide oxidation inhibitor to be employed in a given lubricant will, of course, vary with the particular amide chosen, the nature of the lubricant fluid, and the service conditions to be encountered. However, good results are obtained as a general rule using amounts of about 0.2 to 5% of the amide, with a preferred range being from about 0.5 to 2%.
- additives may properly be employed as well.
- a metal deactivator such as PANA (phenyl-alpha-naphthylamine) along with the amides hereof.
- PANA phenyl-alpha-naphthylamine
- Other conventional additives can be used as Well, including those which impart rust inhibiting or load carrying qualities.
- an auxiliary oxidation inhibitor compound if desired.
- Still another class of additives which can be em ployed, if desired, comprises those which impart improved V.I. characteristics to the composition.
- EXAMPLE 1 This example describes the preparation of N,Ndimethyl-isostearamidopropyl amine.
- a solution was prepared from 30 grams of xylene and 2196 grams (1 mole) of isostearic acid. To this solution was added 120.4 grams 1.2 moles) of N,N-dimethy1-arninopropyl amine, addition of the amine being effected slowly (2-3 hours) as the solution was refluxed at 2002'10 C.
- the water of reaction was removed azeotropically under reflux by means of a water trap. After the addition of the amine was completed the material was allowed to reflux (200 C.) for six hours to distill off all possible water of reaction, the water being collected ina Banett trap.
- the reaction mixture was stripped to 120 C. under a vacuum of 1 mm. of mercury to remove the xylene and the excess amine. This stripping stage required one hour.
- the amide formed had an acid value of 1.2 milligrams of KO H per gram of
- EXAMPLE 4 not effect an unduly pronounced change in the 'low temperature viscosity characteristics of the fluid.
- EXAMPLE 6 The amide of Example 1 was incorporated at the 1% level, along with 0.5% PANA, where indicated, in diisooctyl azelate. The resulting material was then subjected to oxidation-corrosion testing under MlL-L-7808E conditions, air being passed through the fluid at a rate of S l./ hr. as the fluid was maintained at 400 F. rather than 347 F., as called for by the specification. During the test copper, steel, aluminum and magnesium coupons were suspended in the test liquid. The results of this test are given in Table II below, it being noted that in contro run 1, the oxidation inhibitor employed was 0.5% phenothiazine, this being the conventional additive and corresponding level of the art.
- EXAMPLE 5 In the runs included in this example, the amide of EXAMPLE 7 The tests described in this example were conducted in accordance with the ,so-called celanese method, both in Example 1 was admixed with various ester base fluids its former version (4250 48 hrs, 96 L air/hr. Cu,
- a stabilized lubricant composition comprising a major portion of a lubricating oil, together with from 0.2 to 5% of an amide of the type having the general formula test.
- TMP trimethylol propane
- aliphatof Said formula ic saturated acids of from about 5 to 10 carbon atoms 3
- the lubricant of claim 2 wherein the lubricant are particularly well adapted to be used in high temterial is an aliphatic carboxylic acid ester Denimre l lublficant applicationsfrom a 4.
- the lubricant of claim 2 wherein the lubricant mastability standpoint, these ester compounds seem to r terial is a dialkyl ester'of an aliphatic dicar-boxylic acid spond Particularly Well to compoundmg Wlth the amldes having from 6 to 10 carbon atoms and an alcohol having of this invention, thus providing stabilized lubricant fluids f to 10 carbon w Which c either be used as such in the Presence of 5.
- the lubricant of claim 2 wherein the lubricant masuch other additives as may be incorporated in the sysi l is a di t l l m tem.
- t i l is an ester of a polyalkylene glycol and an aliphatic be obtained with esters of the closely related compounds, monocarboxyfic id trimethylol ethane, and trimethylol butane, it being recog- 7.
- the lubricant of claim 2 wherein the lubricant manized that the TMB esters would be somewhat poorer in terial is dipropylene glycol dipelargonate.
- lubricant material is a triester of a trimethylol alkane and at least one aliphatic, monocarboxylic acid of the group consisting of straight chain and branched chain acids containing from about 5 to 10 carbon atoms.
- lubricant material is a triester of trimethylol propane and at least one aliphatic, monocarboxylic acid of the group consisting of straight chain and branched chain acids containing from about 5 to 10 carbon atoms.
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- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NL300948D NL300948A (de) | 1962-11-23 | ||
US239812A US3260671A (en) | 1962-11-23 | 1962-11-23 | Amide oxidation inhibitor for lubricants |
DEU10294A DE1247526B (de) | 1962-11-23 | 1963-11-22 | Amide als Antioxydans fuer Schmiermittel |
FR954728A FR1381625A (fr) | 1962-11-23 | 1963-11-22 | Inhibiteur de type amidique pour des huiles lubrifiantes |
GB46478/63A GB1049199A (en) | 1962-11-23 | 1963-11-25 | Novel amino-amides and their use in lubricant compositions |
BE640380A BE640380A (de) | 1962-11-23 | 1963-11-25 | |
CH1442563A CH448348A (de) | 1962-11-23 | 1963-11-25 | Stabilisiertes Schmiermittel |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US239812A US3260671A (en) | 1962-11-23 | 1962-11-23 | Amide oxidation inhibitor for lubricants |
Publications (1)
Publication Number | Publication Date |
---|---|
US3260671A true US3260671A (en) | 1966-07-12 |
Family
ID=22903848
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US239812A Expired - Lifetime US3260671A (en) | 1962-11-23 | 1962-11-23 | Amide oxidation inhibitor for lubricants |
Country Status (6)
Country | Link |
---|---|
US (1) | US3260671A (de) |
BE (1) | BE640380A (de) |
CH (1) | CH448348A (de) |
DE (1) | DE1247526B (de) |
GB (1) | GB1049199A (de) |
NL (1) | NL300948A (de) |
Cited By (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3405064A (en) * | 1963-06-06 | 1968-10-08 | Lubrizol Corp | Lubricating oil composition |
US5814111A (en) * | 1995-03-14 | 1998-09-29 | Shell Oil Company | Gasoline compositions |
US20060059770A1 (en) * | 2004-09-17 | 2006-03-23 | Sutkowski Andrew C | Fuel oils |
EP1640438A1 (de) | 2004-09-17 | 2006-03-29 | Infineum International Limited | Verbesserungen in Brennölen. |
WO2010005947A2 (en) | 2008-07-11 | 2010-01-14 | Innospec Fuel Specialties, LLC | Fuel composition with enhanced low temperature properties |
US20100258070A1 (en) * | 2007-09-27 | 2010-10-14 | Innospec Limited | Fuel compositions |
US20100293844A1 (en) * | 2007-09-27 | 2010-11-25 | Macmillan John Alexander | Additives for Diesel Engines |
WO2010136822A2 (en) | 2009-05-29 | 2010-12-02 | Innospec Limited | Method and use |
US20100299992A1 (en) * | 2007-09-27 | 2010-12-02 | Jacqueline Reid | Fuel compositions |
WO2010139994A1 (en) | 2009-06-01 | 2010-12-09 | Innospec Limited | Improvements in efficiency |
EP2302020A1 (de) | 2007-07-28 | 2011-03-30 | Innospec Limited | Verwendung von Additiven zur Verbesserung von Treibstoffzusammensetzungen |
WO2011110860A1 (en) | 2010-03-10 | 2011-09-15 | Innospec Limited | Fuel composition comprising detergent and quaternary ammonium salt additive |
WO2011141731A1 (en) | 2010-05-10 | 2011-11-17 | Innospec Limited | Composition, method and use |
WO2012076896A1 (en) | 2010-12-09 | 2012-06-14 | Innospec Limited | Improvements in or relating to additives for fuels and lubricants |
EP2644684A1 (de) | 2009-02-25 | 2013-10-02 | Innospec Limited | Verfahren und verwendungen betreffend kraftstoffzusammensetzungen. |
US9243199B2 (en) | 2007-09-27 | 2016-01-26 | Innospec Limited | Fuel compositions |
US9315752B2 (en) | 2007-09-27 | 2016-04-19 | Innospec Limited | Fuel compositions |
US11015137B2 (en) | 2017-03-30 | 2021-05-25 | Innospec Limited | Composition, method and use |
US11174442B2 (en) | 2017-03-30 | 2021-11-16 | Innospec Limited | Fuel compositions, methods and uses relating to quaternary ammonium salt additives for fuel used in spark ignition engines |
US11186791B2 (en) | 2017-03-30 | 2021-11-30 | Innospec Limited | Composition, method and use |
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US2459062A (en) * | 1944-02-08 | 1949-01-11 | American Cyanamid Co | Quaternary ammonium compounds |
US2622018A (en) * | 1949-10-19 | 1952-12-16 | Socony Vacuum Oil Co Inc | Motor fuel |
US2805135A (en) * | 1954-08-25 | 1957-09-03 | Eastman Kodak Co | Stabilized hydrocarbon fuel oil compositions and stabilizaers therefor |
US2922708A (en) * | 1958-02-26 | 1960-01-26 | California Research Corp | Gasoline compositions |
US2963339A (en) * | 1960-12-06 | Retarding and levelling agents | ||
US3022147A (en) * | 1959-02-17 | 1962-02-20 | Du Pont | Alkali metal composition additives for fuels of the gasoline range |
US3145137A (en) * | 1961-05-12 | 1964-08-18 | Monsanto Co | Alkanoylamidoalkyleneamines and their quaternary ammonium salts as fungicides |
-
0
- NL NL300948D patent/NL300948A/xx unknown
-
1962
- 1962-11-23 US US239812A patent/US3260671A/en not_active Expired - Lifetime
-
1963
- 1963-11-22 DE DEU10294A patent/DE1247526B/de active Pending
- 1963-11-25 CH CH1442563A patent/CH448348A/de unknown
- 1963-11-25 GB GB46478/63A patent/GB1049199A/en not_active Expired
- 1963-11-25 BE BE640380A patent/BE640380A/xx unknown
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2963339A (en) * | 1960-12-06 | Retarding and levelling agents | ||
US2459062A (en) * | 1944-02-08 | 1949-01-11 | American Cyanamid Co | Quaternary ammonium compounds |
US2622018A (en) * | 1949-10-19 | 1952-12-16 | Socony Vacuum Oil Co Inc | Motor fuel |
US2805135A (en) * | 1954-08-25 | 1957-09-03 | Eastman Kodak Co | Stabilized hydrocarbon fuel oil compositions and stabilizaers therefor |
US2922708A (en) * | 1958-02-26 | 1960-01-26 | California Research Corp | Gasoline compositions |
US3022147A (en) * | 1959-02-17 | 1962-02-20 | Du Pont | Alkali metal composition additives for fuels of the gasoline range |
US3145137A (en) * | 1961-05-12 | 1964-08-18 | Monsanto Co | Alkanoylamidoalkyleneamines and their quaternary ammonium salts as fungicides |
Cited By (32)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3405064A (en) * | 1963-06-06 | 1968-10-08 | Lubrizol Corp | Lubricating oil composition |
US5814111A (en) * | 1995-03-14 | 1998-09-29 | Shell Oil Company | Gasoline compositions |
US20060059770A1 (en) * | 2004-09-17 | 2006-03-23 | Sutkowski Andrew C | Fuel oils |
EP1640438A1 (de) | 2004-09-17 | 2006-03-29 | Infineum International Limited | Verbesserungen in Brennölen. |
US8690969B2 (en) | 2004-09-17 | 2014-04-08 | Infineum International Limited | Fuel oils |
EP2302020A1 (de) | 2007-07-28 | 2011-03-30 | Innospec Limited | Verwendung von Additiven zur Verbesserung von Treibstoffzusammensetzungen |
US20100299992A1 (en) * | 2007-09-27 | 2010-12-02 | Jacqueline Reid | Fuel compositions |
US20100293844A1 (en) * | 2007-09-27 | 2010-11-25 | Macmillan John Alexander | Additives for Diesel Engines |
US9315752B2 (en) | 2007-09-27 | 2016-04-19 | Innospec Limited | Fuel compositions |
US20100258070A1 (en) * | 2007-09-27 | 2010-10-14 | Innospec Limited | Fuel compositions |
US9243199B2 (en) | 2007-09-27 | 2016-01-26 | Innospec Limited | Fuel compositions |
US9163190B2 (en) | 2007-09-27 | 2015-10-20 | Innospec Limited | Fuel compositions |
KR101766986B1 (ko) | 2007-09-27 | 2017-08-09 | 이노스펙 리미티드 | 연료 조성물 |
US9157041B2 (en) | 2007-09-27 | 2015-10-13 | Innospec Limited | Fuel compositions |
US9034060B2 (en) | 2007-09-27 | 2015-05-19 | Innospec Fuel Specialties Llc | Additives for diesel engines |
WO2010005947A2 (en) | 2008-07-11 | 2010-01-14 | Innospec Fuel Specialties, LLC | Fuel composition with enhanced low temperature properties |
EP2644684A1 (de) | 2009-02-25 | 2013-10-02 | Innospec Limited | Verfahren und verwendungen betreffend kraftstoffzusammensetzungen. |
US9085740B2 (en) | 2009-02-25 | 2015-07-21 | Innospec Limited | Methods relating to fuel compositions |
US9394499B2 (en) | 2009-02-25 | 2016-07-19 | Innospec Limited | Methods relating to fuel compositions |
WO2010136822A2 (en) | 2009-05-29 | 2010-12-02 | Innospec Limited | Method and use |
US20120260876A1 (en) * | 2009-06-01 | 2012-10-18 | Innospec Limited | Method of increasing fuel efficiency |
WO2010139994A1 (en) | 2009-06-01 | 2010-12-09 | Innospec Limited | Improvements in efficiency |
EP3447111A1 (de) | 2010-03-10 | 2019-02-27 | Innospec Limited | Kraftstoffzusammensetzungen enthaltend detergens und quaternisiertes ammoniumsalz additiv |
EP2966151A1 (de) | 2010-03-10 | 2016-01-13 | Innospec Limited | Kraftstoffzusammensetzungen enthaltend quaternisiertes ammoniumsalz additiv |
WO2011110860A1 (en) | 2010-03-10 | 2011-09-15 | Innospec Limited | Fuel composition comprising detergent and quaternary ammonium salt additive |
US9493720B2 (en) | 2010-05-10 | 2016-11-15 | Innospec Limited | Gasoline composition, method and use |
US9932536B2 (en) | 2010-05-10 | 2018-04-03 | Innospec Limited | Gasoline composition, method and use |
WO2011141731A1 (en) | 2010-05-10 | 2011-11-17 | Innospec Limited | Composition, method and use |
WO2012076896A1 (en) | 2010-12-09 | 2012-06-14 | Innospec Limited | Improvements in or relating to additives for fuels and lubricants |
US11015137B2 (en) | 2017-03-30 | 2021-05-25 | Innospec Limited | Composition, method and use |
US11174442B2 (en) | 2017-03-30 | 2021-11-16 | Innospec Limited | Fuel compositions, methods and uses relating to quaternary ammonium salt additives for fuel used in spark ignition engines |
US11186791B2 (en) | 2017-03-30 | 2021-11-30 | Innospec Limited | Composition, method and use |
Also Published As
Publication number | Publication date |
---|---|
DE1247526B (de) | 1967-08-17 |
NL300948A (de) | |
CH448348A (de) | 1967-12-15 |
BE640380A (de) | 1964-05-25 |
GB1049199A (en) | 1966-11-23 |
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