EP1770151A1 - Zusatzkonzentrat - Google Patents

Zusatzkonzentrat Download PDF

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Publication number
EP1770151A1
EP1770151A1 EP06119413A EP06119413A EP1770151A1 EP 1770151 A1 EP1770151 A1 EP 1770151A1 EP 06119413 A EP06119413 A EP 06119413A EP 06119413 A EP06119413 A EP 06119413A EP 1770151 A1 EP1770151 A1 EP 1770151A1
Authority
EP
European Patent Office
Prior art keywords
concentrate
butylamine
acid
fuel
weight
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP06119413A
Other languages
English (en)
French (fr)
Inventor
Angela Priscilla Dr. Breakspear
Rinaldo Caprotti
Carlo S. Fava
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Infineum International Ltd
Original Assignee
Infineum International Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Infineum International Ltd filed Critical Infineum International Ltd
Priority to EP06119413A priority Critical patent/EP1770151A1/de
Publication of EP1770151A1 publication Critical patent/EP1770151A1/de
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • 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
    • C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • C10L10/08—Use of additives to fuels or fires for particular purposes for improving lubricity; for reducing wear
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/26—Carboxylic acids; Salts thereof
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/188—Carboxylic acids; metal salts thereof
    • C10L1/1881—Carboxylic acids; metal salts thereof carboxylic group attached to an aliphatic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/188—Carboxylic acids; metal salts thereof
    • C10L1/1888—Carboxylic acids; metal salts thereof tall oil

Definitions

  • This invention relates to additive concentrates, and to their use to improve the characteristics of fuel oils, especially middle distillate fuels such as diesel fuels, kerosene and jet fuel.
  • a fuel oil composition with a sulphur level below 0.05% by weight is referred to herein as a low-sulphur fuel.
  • Such low-sulphur fuels may contain an additive to enhance their lubricity.
  • additives are of several types.
  • WO 94/17160 there is disclosed a low sulphur fuel comprising a carboxylic acid ester to enhance lubricity, more especially an ester in which the acid moiety contains from 2 to 50 carbon atoms and the alcohol moiety contains one or more carbon atoms.
  • a mixture of a dimer acid, for example, the dimer of linoleic acid, and a partially esterified polyhydric alcohol is described for the same purpose.
  • U.S. Patent No. 3287273 the use of an optionally hydrogenated dimer acid glycol ester is described.
  • lubricity enhancers or anti-wear agents as they are also termed, include a sulphurized dioleyl norbornene ester (EP-A-99595 ), castor oil ( U.S. Patent No. 4375360 and EP-A-605857 ) and, in methanol-containing fuels, a variety of alcohols and acids having from 6 to 30 carbon atoms, acid and alcohol ethoxylates, mono- and di-esters, polyol esters, and olefin-carboxylic acid copolymers and vinyl alcohol polymers (also U.S. Patent No. 4375360 ).
  • EP-A-99595 sulphurized dioleyl norbornene ester
  • castor oil U.S. Patent No. 4375360 and EP-A-605857
  • methanol-containing fuels a variety of alcohols and acids having from 6 to 30 carbon atoms, acid and alcohol ethoxylates, mono- and di-esters, polyol esters, and
  • Such additives are commonly provided in the form of additive concentrates where the active species is dissolved in a solvent, optionally together with other additives.
  • lubricity additives Although largely effective as lubricity additives, it has been found that certain carboxylic acids and carboxylic acid esters, as well as other known lubricity additives, have the disadvantage of poor solubility at low temperature. This poor solubility is found in relation to the solvents used to provide additive concentrates (normally hydrocarbon based), and also in relation to the fuels into which the additive is added. This places a limitation on the storage and use of certain known lubricity additive concentrates at low ambient temperatures.
  • EP 0 798 364 A1 describes the use of a salt formed by the reaction between a carboxylic acid and an aliphatic amine to improve inter alia, the lubricity of a diesel fuel.
  • the amines used have hydrocarbyl groups of between 2 and 50 carbon atoms, preferably between 8 and 20 carbon atoms, with amines such as oleyl amine being exemplified. There is no discussion of the low temperature behaviour of the salts.
  • US 6,277,158 describes a concentrate containing n-butlyamine oleate as a friction modifier for addition to motor gasoline.
  • the authors state that despite substantial research investigating a wide range of friction modifier compounds, n-butylamine oleate was one of only two compounds which gave the desired stability over a temperature range, and effectiveness when used in combination with a detergent.
  • the concentrate containing n-butylamine oleate is shown to be stable at -20°C for extended periods although there is no indication of the amount of compound present in the concentrate.
  • US2002/0095858 relates to fuel oil compositions containing an additive formed by the reaction of a mono- or dicarboxylic acid of 6 to 50 carbon atoms with an amine having at least one branched alkyl substituent. These additives are shown to be effective lubricity enhancers for the fuel. Data are presented showing that the additives per se have good low temperature properties (e.g. pour point) and are stable when held at -25°C for 3 days. To demonstrate an advantageous property of the additives, they are compared to a similar species derived from an amine with linear rather than branched alkyl groups, namely oleic acid neutralised with tri-n-butylamine. The data show that this comparative compound had poorer low temperature properties and crystallised after 3 days at -25°C. There are no data relating to any additive concentrates i.e. compound dissolved in a carrier fluid or solvent.
  • a suitable additive may be formed by the reaction of N, N-dibutylamine with an acid mixture consisting of 70% fatty acids and 30% resin-based acids. This additive is shown to be soluble in diesel fuel in an amount of 5% by weight. HFRR data are presented, but there is no discussion of the low temperature properties of the additives.
  • the present invention is based on the discovery that additive concentrates containing certain salts derived from certain aliphatic amines have greatly improved low temperature solubility when compared to closely related salts.
  • the salts are effective lubricity enhancers for low sulphur content fuels. It is also an advantage that the salts used in the invention have relatively high flash points. This leads to benefits in terms of the ease of, and hazards associated with, their handling and transportation.
  • the present invention provides an additive concentrate comprising a lubricity enhancer dissolved in a solvent; wherein the lubricity enhancer comprises from 10 to 90% by weight of the concentrate; wherein the lubricity enhancer comprises a salt formed by the reaction of a carboxylic acid with di-n-butylamine or tri-n-butylamine; and wherein the concentrate remains clear and bright for at least 14 days when held at -30°C.
  • the lubricity enhancer comprises from 10 to 80%, more preferably 20 to 80%, for example 33 to 75% by weight of the concentrate and the concentrate remains clear and bright for at least 14 days when held at -30°C.
  • the lubricity enhancer comprises from 33 to 50% by weight of the concentrate, and the concentrate remains clear and bright for at least 14 days when held at -40°C.
  • the lubricity enhancer comprises from 33 to 50% by weight of the concentrate, and the concentrate remains clear and bright for at least 28 days when held at -30°C.
  • the use of the term 'salt' to describe the product formed by the reaction of the carboxylic acid and the amine should not be taken to mean that the reaction necessarily forms a pure salt. It is presently believed that the reaction does form a salt and thus that the reaction product contains such as salt however, due to the complexity of the reaction, it is likely that other species will also be present.
  • the term 'salt' should thus be taken to include not only the pure salt species, but also the mixture of species formed during the reaction of the carboxylic acid and the amine.
  • di-n-butylamine or tri-n-butylamine is used although mixtures of the two may also be used if desired.
  • the salt is formed by the reaction with di-n-butylamine.
  • each R' is independently a hydrocarbon group of between 2 and 45 carbon atoms, and x is an integer between 1 and 4, are suitable.
  • R' is a hydrocarbon group of 8 to 24 carbon atoms, more preferably, 12 to 20 carbon atoms.
  • x is 1 or 2, more preferably, x is 1.
  • y is 1, in which case the acid has a single R' group.
  • the acid may be a dimer, trimer or higher oligomer acid, in which case y will be greater than 1 for example 2, 3 or 4 or more.
  • R' is suitably an alkyl or alkenyl group which may be linear or branched.
  • carboxylic acids which may be used in the present invention include: lauric acid, myristic acid, palmitic acid, stearic acid, isostearic acid, neodecanoic acid, arachic acid, behenic acid, lignoceric acid, cerotic acid, montanic acid, melissic acid, caproleic acid, oleic acid, elaidic acid, linoleic acid, linolenic acid, coconut oil fatty acid, soy bean fatty acid, tall oil fatty acid, sunflower oil fatty acid, fish oil fatty acid, rapeseed oil fatty acid, tallow oil fatty acid and palm oil fatty acid.
  • the carboxylic acid comprises tall oil fatty acid (TOFA). It has been found that TOFA with a saturate content of less than 5% by weight is especially suitable. As is known in the art, TOFA contains small but variable amounts of rosin acids and isomers thereof. Preferably, TOFA with an abietic acid content of less than 5% by weight, for example, less than 2% by weight, is used.
  • TOFA tall oil fatty acid
  • the carboxylic acid comprises rapeseed oil fatty acid.
  • the carboxylic acid comprises soy bean fatty acid.
  • the carboxylic acid comprises sunflower oil fatty acid.
  • aromatic carboxylic acids and their alkyl derivatives as well as aromatic hydroxy acids and their alkyl derivatives.
  • Illustrative examples include benzoic acid, salicylic acid and acids derived from such species.
  • the carboxylic acid has an iodine value of at least 80g/100g, more preferably at least 100 g/100g, for example, at least 130 g/100g or at least 150 g/100g. This has been found to further improve the low temperature solubility of the salts of the invention.
  • the salt has a flash point of at least 50°C, more preferably at least 60°C.
  • the salt may conveniently be produced by mixing the carboxylic acid with the amine.
  • the order in which one component is added to the other is not important.
  • the molar ratio of the amount of acid to the amount of amine is suitably from 10:1 to 1:10, preferably from 10:1 to 1:2, more preferably from 2:1 to 1:2, for example, around 1:1. In an embodiment, a molar ratio of 1.1:1 to 1:1.1 has been found to be suitable.
  • the reaction may be conducted at room temperature, but is preferably heated gently, for example to 40°C.
  • the solvent is a hydrocarbon solvent, such as an aromatic hydrocarbon solvent.
  • hydrocarbon solvents include petroleum fractions such as naphtha, kerosene, diesel and heater oil; aromatic hydrocarbons such as aromatic fractions, e.g. those sold under the 'SOLVESSO' tradename; alcohols and/or esters; and paraffinic hydrocarbons such as hexane and pentane and isoparaffins.
  • the additive concentrate may also contain further additives as required.
  • Such further additives include, for example the following: detergents, antioxidants (to avoid fuel degradation), corrosion inhibitors, dehazers, demulsifiers, metal deactivators, antifoaming agents, cetane improvers, co-solvents, package compatibilisers, reodourants, additives to improve the regeneration of particulate traps, middle distillate cold flow improvers and other lubricity additives.
  • the present invention provides a fuel oil composition comprising a major amount of a fuel oil and a minor amount of an additive concentrate according to the first aspect.
  • the oil is a fuel oil, e.g., a petroleum-based fuel oil, especially a middle distillate fuel oil.
  • a fuel oil e.g., a petroleum-based fuel oil, especially a middle distillate fuel oil.
  • distillate fuel oils generally boil within the range of from 110°C to 500°C, e.g. 150°C to 400°C.
  • the fuel oil may comprise atmospheric distillate or vacuum distillate, cracked gas oil, or a blend in any proportion of straight run and thermally and/or refinery streams such as catalytically cracked and hydro-cracked distillates.
  • the most common petroleum distillate fuels are kerosene, jet fuels, diesel fuels, heating oils and heavy fuel oils.
  • the heating oil may be a straight atmospheric distillate, or it may contain minor amounts, e.g. up to 35 wt %, of vacuum gas oil or cracked gas oil or of both.
  • Fischer-Tropsch fuels also known as FT fuels
  • FT fuels include those described as gas-to-liquid (GTL) fuels, biomass-to-liquid (BTL) fuels and coal conversion fuels.
  • GTL gas-to-liquid
  • BTL biomass-to-liquid
  • coal conversion fuels coal conversion fuels.
  • syngas (CO + H 2 ) is first generated and then converted to normal paraffins by a Fischer-Tropsch process.
  • the normal paraffins may then be modified by processes such as catalytic cracking/reforming or isomerisation, hydrocracking and hydroisomerisation to yield a variety of hydrocarbons such as iso-paraffins, cyclo-paraffins and aromatic compounds.
  • the resulting FT fuel can be used as such or in combination with other fuel components and fuel types such as those mentioned in this specification.
  • fuels derived from plant or animal sources such as FAME. These may be used alone or in combination with other types of fuel.
  • the fuel oil has a sulphur content of at most 0.05% by weight, more preferably of at most 0.035% by weight, especially of at most 0.015%.
  • Fuels with even lower levels of sulphur are also suitable such as, fuels with less than 50ppm sulphur by weight, preferably less than 20 ppm, for example 10ppm or less.
  • the amount of additive concentrate used is such that the salt is present in the fuel oil at a level of between 5 and 1000 ppm by weight, more preferably between 10 and 500 ppm, even more preferably between 10 and 250 ppm, especially between 10 and 150 ppm, for example, between 50 and 150 ppm.
  • the present invention provides the use of an additive concentrate according to the first aspect to improve the lubricity of a fuel oil having a sulphur content of less than 0.05% by weight.
  • the present invention provides a method of storing an additive concentrate comprising a lubricity enhancer at a temperature of -30°C such that the concentrate remains clear and bright for at least 14 days, the method comprising dissolving 10 to 90% by weight of a salt formed by the reaction of a carboxylic acid with di-n-butylamine or tri-n-butylamine, in a hydrocarbon solvent.
  • the additive of the invention may contain a single salt or a mixture of more than one salt. It may also be used in combination with one or more co-additives
  • FTIR analysis of the reaction product showed a reduction in the strong carboxylic acid peak at 1710cm -1 compared to the starting acid, and a corresponding appearance of carboxylate antisymmetric and symmetric stretches at 1553 and 1399 cm -1 as well as the appearance of a broad range of peaks 2300-2600cm -1 assignable to ammonium species. This was a clear indication of the formation of a salt.
  • the flash-point of the reaction product was 67°C.
  • Example 1 was repeated using tri-n-butylamine in place of di-n-butylamine.
  • Tall oil fatty acid, with a saturate content of ca. 2% and a rosin acid content of ca. 1.8%, (TOFA-1) (30.0g, 94.5mmoles) was added to a beaker and with stirring.
  • Tri-n-butylamine (17.52g, 94.5mmoles) was then added to the beaker.
  • An exotherm of ca. 13°C was measured indicating that the two components reacted.
  • FTIR analysis of the reaction product showed a reduction in the strong carboxylic acid peak at 1710cm -1 compared to the starting acid, and a corresponding appearance of carboxylate antisymmetric and symmetric stretches at 1571 and 1371 cm -1 as well as the appearance of a broad range of peaks 2300-2600cm -1 assignable to ammonium species. This was a clear indication of the formation of a salt.
  • the flash-point of the reaction product was 90°C.
  • Example 1 was repeated using a Tall oil fatty acid with a saturate content of ca. 2% and a rosin acid content of ca. 0.8%, (TOFA-2).
  • Example 2 was repeated using a Tall oil fatty acid with a saturate content of ca. 2% and a rosin acid content of ca. 0.8%, (TOFA-2).
  • Rape seed oil fatty acid (33.87g) was added to solvent (Atasol 150, 50g) at ca. 30°C and agitated until well mixed. Di-n-butylamine (16.13g) was then charged to the mixture at ambient temperature. An exotherm was observed indicating that the two components reacted. After the exotherm had diminished, agitation was continued for a further four hours. The product was pumped out below the flash point of the solvent.
  • Example 1 was repeated using di-n-ethylamine in place of di-n-butylamine.
  • the flash point of the product obtained was 42°C.
  • Example 3 was repeated using di-n-ethylamine in place of di-n-butylamine.
  • the flash point of the product obtained was 42°C.
  • Example 1 was repeated using di-n-hexylamine in place of di-n-butylamine.
  • the flash point of the product obtained was 122°C.
  • Example 3 was repeated using di-n-hexylamine in place of di-n-butylamine.
  • the flash point of the product obtained was 122°C.
  • Additive concentrates of the salts of Examples 1-4 were made up as 33, 50 and 75wt% solutions in Solvesso 100 and tested for low temperature stability at -30°C and -40°C alongside similar solutions of Comparative Examples 5-8.
  • the results are given in Table 1 below.
  • the data refer to the number of days that the test sample remained clear and bright. All tests were run for a maximum of 28 days, so a result of '28' in the Table does not necessarily indicate a failure on day 28. It is clear from the results obtained that concentrates according to the invention show improved stability at high concentration and low temperature compared to those containing salts produced from either longer or shorter chain length, linear amines.
  • salts were produced by reacting n-butylamine with TOFA-1 and TOFA-2 following the same procedure as Examples 1 and 3. Concentrates containing 50wt% in Solvesso 100 showed only very limited stability at -40°C (3 days for the TOFA-1 salt). Concentrates containing 75wt% in Solvesso 100 showed no stability at all at -40°C.
  • Example 5 The salt produced in Example 5 was tested in a number of diesel fuels.
  • the material was used as a 50% solution in Solvesso 150 and added to the diesel fuels at a treat rate of 100 wppm (calculated based on active ingredient content).
  • HFRR test results are given in Table 4 below. Each value in the Table is the average of a number of tests.
  • the designation of the fuels used e.g. Korean ULSD(1) and Korean ULSD(2), indicates that two different fuels of the same general type were used.
EP06119413A 2005-09-30 2006-08-23 Zusatzkonzentrat Withdrawn EP1770151A1 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP06119413A EP1770151A1 (de) 2005-09-30 2006-08-23 Zusatzkonzentrat

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP05270062 2005-09-30
EP06119413A EP1770151A1 (de) 2005-09-30 2006-08-23 Zusatzkonzentrat

Publications (1)

Publication Number Publication Date
EP1770151A1 true EP1770151A1 (de) 2007-04-04

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EP06119413A Withdrawn EP1770151A1 (de) 2005-09-30 2006-08-23 Zusatzkonzentrat

Country Status (6)

Country Link
US (1) US20070074449A1 (de)
EP (1) EP1770151A1 (de)
JP (1) JP2007100087A (de)
KR (1) KR20070037358A (de)
CN (1) CN1940036B (de)
CA (1) CA2561663A1 (de)

Cited By (1)

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Publication number Priority date Publication date Assignee Title
EP2107102A3 (de) * 2008-04-04 2009-10-14 Afton Chemical Corporation Succinimid-Schmierzusatz für Dieselkraftstoff

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WO2007082825A1 (de) * 2006-01-18 2007-07-26 Basf Se Verwendung von mischungen aus monocarbonsäuren und polycyclischen kohlenwasserstoffverbindungen zur verbesserung der lagerstabilität von kraftstoffadditiv-konzentraten
US20080060608A1 (en) * 2006-09-07 2008-03-13 Angela Priscilla Breakspear Method and use for the prevention of fuel injector deposits
US20080141582A1 (en) * 2006-12-13 2008-06-19 Angela Priscilla Breakspear Additive Composition

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US20020014034A1 (en) * 1996-07-31 2002-02-07 Christian Bernasconi Fuel with low sulphur content for diesel engines
US20020095858A1 (en) * 2000-11-24 2002-07-25 Matthias Krull Enhanced lubricity fuel oil compositions comprising salts of fatty acids with short chain oil-soluble amines
US20030200697A1 (en) * 2002-04-24 2003-10-30 Aradi Allen A. Friction modifier additives for fuel compositions and methods of use thereof

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US20020014034A1 (en) * 1996-07-31 2002-02-07 Christian Bernasconi Fuel with low sulphur content for diesel engines
US20020095858A1 (en) * 2000-11-24 2002-07-25 Matthias Krull Enhanced lubricity fuel oil compositions comprising salts of fatty acids with short chain oil-soluble amines
US20030200697A1 (en) * 2002-04-24 2003-10-30 Aradi Allen A. Friction modifier additives for fuel compositions and methods of use thereof

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2107102A3 (de) * 2008-04-04 2009-10-14 Afton Chemical Corporation Succinimid-Schmierzusatz für Dieselkraftstoff
US8690968B2 (en) 2008-04-04 2014-04-08 Afton Chemical Corporation Succinimide lubricity additive for diesel fuel and a method for reducing wear scarring in an engine

Also Published As

Publication number Publication date
US20070074449A1 (en) 2007-04-05
CN1940036B (zh) 2014-09-17
KR20070037358A (ko) 2007-04-04
JP2007100087A (ja) 2007-04-19
CN1940036A (zh) 2007-04-04
CA2561663A1 (en) 2007-03-30

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