WO2010012763A1 - Liquid fuel compositions - Google Patents
Liquid fuel compositions Download PDFInfo
- Publication number
- WO2010012763A1 WO2010012763A1 PCT/EP2009/059795 EP2009059795W WO2010012763A1 WO 2010012763 A1 WO2010012763 A1 WO 2010012763A1 EP 2009059795 W EP2009059795 W EP 2009059795W WO 2010012763 A1 WO2010012763 A1 WO 2010012763A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- liquid fuel
- acid
- acid group
- fuel composition
- Prior art date
Links
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
- C10L1/224—Amides; Imides carboxylic acid amides, imides
-
- 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
-
- 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
- C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
-
- 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
- C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
- C10L1/191—Esters ester radical containing compounds; ester ethers; carbonic acid esters of di- or polyhydroxyalcohols
-
- 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
- C10L1/192—Macromolecular compounds
- C10L1/198—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid
- C10L1/1983—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid polyesters
-
- 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
- C10L1/23—Organic compounds containing nitrogen containing at least one nitrogen-to-oxygen bond, e.g. nitro-compounds, nitrates, nitrites
-
- 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
- C10L1/234—Macromolecular compounds
- C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
-
- 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
- C10L1/24—Organic compounds containing sulfur, selenium and/or tellurium
- C10L1/2431—Organic compounds containing sulfur, selenium and/or tellurium sulfur bond to oxygen, e.g. sulfones, sulfoxides
- C10L1/2437—Sulfonic acids; Derivatives thereof, e.g. sulfonamides, sulfosuccinic acid esters
-
- 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
- C10L1/24—Organic compounds containing sulfur, selenium and/or tellurium
- C10L1/2462—Organic compounds containing sulfur, selenium and/or tellurium macromolecular compounds
- C10L1/2475—Organic compounds containing sulfur, selenium and/or tellurium macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon to carbon bonds
-
- 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
- C10L1/26—Organic compounds containing phosphorus
- C10L1/2608—Organic compounds containing phosphorus containing a phosphorus-carbon bond
-
- 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
- C10L1/26—Organic compounds containing phosphorus
- C10L1/2633—Organic compounds containing phosphorus phosphorus bond to oxygen (no P. C. bond)
-
- 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
- C10L1/26—Organic compounds containing phosphorus
- C10L1/2666—Organic compounds containing phosphorus macromolecular compounds
- C10L1/2683—Organic compounds containing phosphorus macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon to carbon bonds
-
- 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
- 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
- C10L10/18—Use of additives to fuels or fires for particular purposes use of detergents or dispersants for purposes not provided for in groups C10L10/02 - C10L10/16
-
- 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
- C10M145/00—Lubricating compositions characterised by the additive being a macromolecular compound containing oxygen
- C10M145/18—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M145/22—Polyesters
-
- 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
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/102—Polyesters
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/02—Pour-point; Viscosity index
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/04—Detergent property or dispersant property
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/40—Low content or no content compositions
- C10N2030/41—Chlorine free or low chlorine content compositions
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/40—Low content or no content compositions
- C10N2030/42—Phosphor free or low phosphor content compositions
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/40—Low content or no content compositions
- C10N2030/43—Sulfur free or low sulfur content compositions
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/40—Low content or no content compositions
- C10N2030/45—Ash-less or low ash content
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
Definitions
- the present invention relates to liquid fuel compositions comprising a major portion of a base fuel suitable for use in an internal combustion engine, in particular liquid fuel compositions comprising a major portion of a base fuel suitable for use in an internal combustion engine and a hyperdispersant .
- EP 0164817 A2 discloses a surfactant comprising a carboxylic acid ester or amide carrying a terminal strong acid group selected from carboxylic acid, carboxymethyl, sulphate, sulphonate, phosphate and phosphonate, suitable for stabilising dispersions of solids in organic liquids and oil/water emulsions.
- a preferred species of the surfactant is a poly (hydroxyalkanecarboxylic acid) having the strong acid group attached, either directly or through a linking group, to a terminal hydroxy or carboxylic acid group. The use of such surfactants in fuels is not disclosed therein.
- EP 0233684 Al discloses an ester or polyester having
- GB 2197312 A discloses oil soluble dispersant additives, wherein said dispersant additives are poly (C 5 -C 9 lactone) adducts which have been prepared by first reacting a C 5 -C 9 lactone with a polyamine, a polyol or an amino alcohol to form an intermediate adduct, whereafter the intermediate adduct is reacted with an aliphatic hydrocarbyl monocarboxylic or dicarboxylic acylating agent having from about 1 to about 165 total carbon atoms.
- the use of the dispersant additives in lubricating oils and fuels is also disclosed in GB 2197312 A.
- EP 0802255 A2 discloses hydroxyl group containing acylated nitrogen compounds which are useful as low chlorine containing additives for lubricating oils and normally liquid fuels and a process for preparing the compounds .
- WO 00/34418 Al discloses the use of poly (hydroxycarboxylic acid) amide or -ester derivatives in fuel compositions as a lubricity additive. It is also disclosed in WO 00/34418 Al that the use of the poly (hydroxycarboxylic acid) amide or -ester derivatives disclosed therein may also result in attaining one or more of a number of effects such as inlet system cleanliness (intake valves, fuel injectors, carburetors), combustion chamber clealiness (in each case either or both of keep clean and clean-up effects) , anti-corrosion (including anti-rust) and reduction or elimination of valve-stick .
- inlet system cleanliness intake valves, fuel injectors, carburetors
- combustion chamber clealiness in each case either or both of keep clean and clean-up effects
- anti-corrosion including anti-rust
- the present invention provides a liquid fuel composition comprising: a liquid base fuel suitable for use in an internal combustion engine; and one or more poly (hydroxycarboxylic acid) derivative having a terminal strong acid group having formula (III) :
- Y-CO [0-A-CO] n -Zp] m -X (III) wherein Y is hydrogen or optionally substituted hydrocarbyl group, A is a divalent optionally substituted hydrocarbyl group, n is from 1 to 100, m is 1 or 2, Z is an optionally substituted divalent bridging group, p is 0 or 1, and X is terminal acid group or a group carrying a terminal acid group, wherein the terminal acid group is selected from carboxylic acid, carboxymethyl, sulphate, sulphonate, phosphate and phosphonate.
- the present invention further provides a method for preparing a liquid fuel composition of the present invention comprising admixing the one or more poly (hydroxycarboxylic acid) derivative having a terminal acid group with a base fuel suitable for use in an internal combustion engine.
- the present invention yet further provides a method of operating an internal combustion engine, which method involves introducing into a combustion chamber of the engine a liquid fuel composition according to the present invention
- the liquid fuel composition of the present invention comprises a base fuel suitable for use in an internal combustion engine and one or more poly (hydroxycarboxylic acid) derivative having a terminal acid group.
- the base fuel suitable for use in an internal combustion engine is a gasoline or a diesel fuel, and therefore the liquid fuel composition of the present invention is typically a gasoline composition or a diesel fuel composition.
- the poly (hydroxycarboxylic acid) derivative having a terminal acid group used in the present invention may also be referred to as hyperdispersants .
- the one or more poly (hydroxycarboxylic acid) derivative having a terminal acid group in the liquid fuel compositions of the present invention are poly (hydroxycarboxylic acid) derivative having a terminal acid group having formula (III):
- Y-CO [0-A-CO] n -Z p ] m -X (III) wherein Y is hydrogen or optionally substituted hydrocarbyl group, A is a divalent optionally substituted hydrocarbyl group, n is from 1 to 100, m is 1 or 2, Z is an optionally substituted divalent bridging group, p is 0 or 1, and X is terminal acid group or a group carrying a terminal acid group, wherein the terminal acid group is selected from carboxylic acid, carboxymethyl, sulphate, sulphonate, phosphate and phosphonate.
- A is preferably a divalent straight chain or branched hydrocarbyl group as hereafter described for formulae (I) and (II) below. That is to say, in formula (III), A is preferably an optionally substituted aromatic, aliphatic or cycloaliphatic straight chain or branched divalent hydrocarbyl group.
- A is an arylene, alkylene or alkenylene group, in particular an arylene, alkylene or alkenylene group containing in the range of from 4 to 25 carbon atoms, more preferably in the range of from 6 to 25 carbon atoms, more preferably in the range of from 8 to 24 carbon atoms, more preferably in the range of from 10 to 22 carbon atoms, and most preferably in the range of from 12 to 20 carbon atoms.
- the optional substituents in the group A are preferably selected from hydroxy, halo or alkoxy groups, especially Ci_ 4 alkoxy groups .
- n is in the range of from 1 to 100.
- the lower limit of the range for n is 1, more preferably 2, even more preferably 3; preferably the upper limit of the range for n is 100, more preferably 60, more preferably 40, more preferably 20, and even more preferably 10 (i.e. n may be selected from any of the following ranges: from 1 to 100; from 2 to 100; from 3 to 100; from 1 to 60; from 2 to 60; from 3 to 60; from 1 to 40; from 2 to 40; from 3 to 40; from 1 to 20; from 2 to 20; from 3 to 20; from 1 to 10; from 2 to 10; and, from 3 to 10) .
- Y is preferably an optionally substituted hydrocarbyl group as hereinbefore described for formula (I) .
- the optionally substituted hydrocarbyl group Y in formula (III) is preferably aryl, alkyl or alkenyl containing up to 50 carbon atoms, more preferably in the range of from 7 to 25 carbon atoms.
- the optionally substituted hydrocarbyl group Y may be conveniently selected from heptyl, octyl, undecyl, lauryl, heptadecyl, heptadenyl, heptadecadienyl, stearyl, oleyl and linoleyl.
- optionally substituted hydrocarbyl group Y in formula (III) herein include C 4 - 8 cycloalkyls such as cyclohexyl; polycycloalkyls such as polycyclic terpenyl groups which are derived from naturally occurring acids such as abietic acid; aryls such as phenyl; aralkyls such as benzyl; and polyaryls such as naphthyl, biphenyl, stibenyl and phenylmethylphenyl .
- the optionally substituted hydrocarbyl group Y in formula (III) may contain one or more functional groups such as carbonyl, carboxyl, nitro, hydroxy, halo, alkoxy, amino, preferably tertiary amino (no N-H linkages), oxy, cyano, sulphonyl and sulphoxyl .
- the majority of the atoms, other than hydrogen, in substituted hydrocarbyl groups are generally carbon, with the heteroatoms (e.g., oxygen, nitrogen and sulphur) generally representing only a minority, about 33% or less, of the total non-hydrogen atoms present.
- the hydrocarbyl group Y in formula (III) is unsubstituted or substituted by a group selected from hydroxy, halo or alkoxy group, even more preferably Ci-4 alkoxy.
- the optionally substituted hydrocarbyl group Y in formula (III) is a stearyl group, 12-hydroxystearyl group, an oleyl group or a 12- hydroxyoleyl group, and that derived from naturally occurring oil such as tall oil fatty acid.
- Z is an optionally substituted divalent bridging group, preferably of the formula -X z -B-Y z q -, wherein X z is selected from oxygen, sulphur or a group of the formula -NR 1 -, wherein R 1 is as described below, B is as described below, Y z is selected from oxygen or a group of the formula -NR 1 -, wherein R 1 is as described below, and q is 0 or 1. If q is 1 and both X z and Y z are groups of the formula -NR 1 -, then the two R 1 groups may form a single hydrocarbyl group linking the two nitrogen atoms.
- Z is an optionally substituted divalent bridging group which is attached to the carbonyl group through a nitrogen atom, preferably represented by formula (IV)
- R 1 wherein R 1 is hydrogen Oo]r a hydrocarbyl group and B is an optionally substituted alkylene group.
- hydrocarbyl groups that may represent R 1 include methyl, ethyl, n-propyl, n-butyl and octadecyl .
- optionally substituted alkylene groups that may represent B include ethylene, trimethylene, tetramethylene and hexamethylene .
- Examples of preferred Z moieties in formula (III) include -NHCH 2 CH 2 -, -NHCH 2 C (CH 3 ) 2 CH 2 - and -NH (CH 2 ) 3-.
- X is terminal acid group or a group carrying a terminal acid group, wherein the terminal acid group is selected from carboxylic acid, carboxymethyl, sulphate, sulphonate, phosphate and phosphonate.
- X is a group carrying a terminal acid group, then preferably it is a group of the formula -Z 1 -X 1 , wherein Z 1 is a bifunctional linking compound, such as a compound selected from a polyamine, polyol, hydroxylamine, or a Z group as defined above, and X 1 is a terminal acid group selected from carboxylic acid, carboxymethyl, sulphate, sulphonate, phosphate and phosphonate; more preferably, if X is a group carrying a terminal acid group, then p in formula (III) is 0 and X is a group of the formula -Z 1 -X 1 .
- the terminal acid group may be present in the free acid form or in the form of a salt of the acid. If the terminal acid group is in the form of a salt, it is can conveniently be formed by the reaction of the terminal acid in the free acid form with a base, for example, with ammonia, organic bases such as amines and aminoalcohols, and inorganic bases. If the acid group in the terminal acid group is a salt, then examples of suitable cations include metal ions, such as aodium, potassium and calcium, and ammonium ions, such as an ammonium ion (NH 4 + ), N(CHs) 4 + , and NH(CHs) 4 + .
- a base for example, with ammonia, organic bases such as amines and aminoalcohols, and inorganic bases.
- suitable cations include metal ions, such as aodium, potassium and calcium, and ammonium ions, such as an ammonium ion (NH 4 + ), N(CHs) 4 + ,
- the one or more poly (hydroxycarboxylic acid) derivative having a terminal acid group may be obtained by reaction of: a poly (hydroxycarboxylic acid) of formula (I)
- Y-CO[O-A-CO] n -OH (I) wherein Y is hydrogen or optionally substituted hydrocarbyl group, A is a divalent optionally substituted hydrocarbyl group and n is from 1 to 100; with: a compound having a group reactive with the terminal carboxylic acid group of the poly (hydroxycarboxylic acid) of formula (I) and a terminal acid group selected from carboxylic acid, carboxymethyl, sulphate, sulphonate, phosphate and phosphonate; a precursor of the terminal acid group; or a bifunctional linking compound which is subsequently reacted with a precursor of the terminal acid group.
- hydrocarbyl represents a radical formed by removal of one or more hydrogen atoms from a carbon atom of a hydrocarbon (not necessarily the same carbon atoms in case more hydrogen atoms are removed) .
- Hydrocarbyl groups may be aromatic, aliphatic, acyclic or cyclic groups.
- hydrocarbyl groups are aryl, cycloalkyl, alkyl or alkenyl, in which case they may be straight-chain or branched-chain groups.
- Representative hydrocarbyl groups include phenyl, naphthyl, methyl, ethyl, butyl, pentyl, methylpentyl, hexenyl, dimethylhexyl, octenyl, cyclooctenyl, methylcyclooctenyl, dimethylcyclooctyl, ethylhexyl, octyl, isooctyl, dodecyl, hexadecenyl, eicosyl, hexacosyl, triacontyl and phenylethyl .
- the phrase "optionally substituted hydrocarbyl” is used to describe hydrocarbyl groups optionally containing one or more "inert” heteroatom-containing functional groups.
- inert is meant that the functional groups do not interfere to any substantial degree with the function of the compound.
- the optionally substituted hydrocarbyl group Y in formula (I) herein is preferably aryl, alkyl or alkenyl containing up to 50 carbon atoms, more preferably in the range of from 7 to 25 carbon atoms.
- the optionally substituted hydrocarbyl group Y may be conveniently selected from heptyl, octyl, undecyl, lauryl, heptadecyl, heptadenyl, heptadecadienyl, stearyl, oleyl and linoleyl.
- optionally substituted hydrocarbyl group Y in formula (I) herein include C4-8 cycloalkyls such as cyclohexyl; polycycloalkyls such as polycyclic terpenyl groups which are derived from naturally occurring acids such as abietic acid; aryls such as phenyl; aralkyls such as benzyl; and polyaryls such as naphthyl, biphenyl, stibenyl and phenylmethylphenyl .
- the optionally substituted hydrocarbyl group Y may contain one or more functional groups such as carbonyl, carboxyl, nitro, hydroxy, halo, alkoxy, tertiary amino (no N-H linkages) , oxy, cyano, sulphonyl and sulphoxyl .
- the majority of the atoms, other than hydrogen, in substituted hydrocarbyl groups are generally carbon, with the heteroatoms (e.g., oxygen, nitrogen and sulphur) generally representing only a minority, about 33% or less, of the total non-hydrogen atoms present.
- the hydrocarbyl group Y in formula (I) is more preferably unsubstituted or substituted by a group selected from hydroxy, halo or alkoxy group, even more preferably Ci_ 4 alkoxy.
- the optionally substituted hydrocarbyl group Y in formula (I) is a stearyl group, 12-hydroxystearyl group, an oleyl group, a 12- hydroxyoleyl group or a group derived from naturally occurring oil such as tall oil fatty acid.
- the poly (hydroxycarboxylic acid) s of formula (I) may be made by the interesterification of one or more hydroxycarboxylic acids of formula (II)
- the chain terminator in said interesterification may be a non-hydroxycarboxylic acid.
- the hydroxyl group in the hydroxycarboxylic acid and the carboxylic acid group in the hydroxycarboxylic acid or the non-hydroxycarboxylic acid may be primary, secondary or tertiary in character.
- the interesterification of the hydroxycarboxylic acid and the non-hydroxycarboxylic acid chain terminator may be effected by heating the starting materials, optionally in a suitable hydrocarbon solvent such as toluene or xylene, and azeotroping off the formed water.
- the reaction may be carried out at a temperature up to -25O 0 C, conveniently at the reflux temperature of the solvent .
- the temperature employed should not be so high as to lead to dehydration of the acid molecule.
- Catalysts for the interesterification such as p-toluenesulphonic acid, zinc acetate, zirconium naphthenate or tetrabutyl titanate, may be included, with the objective of either increasing the rate of reaction at a given temperature or of reducing the temperature required for a given rate of reaction.
- A is preferably an optionally substituted aromatic, aliphatic or cycloaliphatic straight chain or branched divalent hydrocarbyl group.
- A is an arylene, alkylene or alkenylene group, in particular an arylene, alkylene or alkenylene group containing in the range of from 4 to 25 carbon atoms, more preferably in the range of from 6 to 25 carbon atoms, more preferably in the range of from 8 to 24 carbon atoms, more preferably in the range of from 10 to 22 carbon atoms, and most preferably in the range of from 12 to 20 carbon atoms.
- the optional substituents in the group A are preferably selected from hydroxy, halo or alkoxy groups, more preferably C1-4 alkoxy groups.
- the hydroxyl group in the hydroxycarboxylic acids of formula (II) is preferably a secondary hydroxyl group.
- suitable hydroxycarboxylic acids are
- 12-hydroxystearic acid 9-hydroxystearic acid, 10-hydroxystearic acid, 12-hydroxystearic acid, 12-hydroxy-9-oleic acid (ricinoleic acid) , 6-hydroxycaproic acid, preferably 12- hydroxystearic acid.
- Commercial 12-hydroxystearic acid hydrogenated castor oil fatty acid
- the proportion which is required in order to produce a polymer or oligomer of a given molecular weight can be determined either by simple experiment or by calculation by the person skilled in the art.
- the group (-O-A-CO-) in the compounds of formulae (I) and (II) is preferably a 12-oxystearyl group, 12- oxyoleyl group or a 6-oxycaproyl group.
- Preferred poly (hydroxycarboxylic acid) s of formula (I) for reaction with amine include poly (hydroxystearic acid) and poly (hydroxyoleic acid).
- Suitable compounds having a group reactive with the terminal carboxylic acid group of the poly (hydroxycarboxylic acid) of formula (I) and a terminal acid group selected from carboxylic acid, carboxymethyl, sulphate, sulphonate, phosphate and phosphonate include alpha-amino- or alpha-hydroxy-alkane carboxylic acids, such as glycine and glycollic acid and amino- and hydroxy-organic sulphonic or posphonic acids, such as aminoethane sulphonic acid; suitable precursors of the terminal acid group are phosphorus pentoxide and sulphonyl chloride; and, suitable bifunctional linking compounds, which can form a linking group between the polyester and the terminal acid group, are polyamines, polyols, hydroxyamines and Z groups as described above.
- reaction of a compound having a group reactive with the terminal carboxylic acid group of the poly (hydroxycarboxylic acid) of formula (I) and a terminal acid group selected from carboxylic acid, carboxymethyl, sulphate, sulphonate, phosphate and phosphonate; a precursor of the terminal acid group; or a bifunctional linking compound which is subsequently reacted with a precursor of the terminal acid group, with a poly (hydroxycarboxylic acid) of formula (I) is known and is described in the art, for example in EP 0 164 817.
- the poly (hydroxycarboxylic acid) derivatives having a terminal acid group that are preferred in the present invention are those which each have a TBN (total base number) value of less than 60 mg.KOH/g, more preferably less than 50 mg.KOH/g, even more preferably less than 40 mg.KOH/g and most preferably less than 30 mg.KOH/g, as measured by ASTM D 4739.
- the poly (hydroxycarboxylic acid) derivatives having a terminal acid group may each have a TBN value of less than 5 mg.KOH/g, more conveniently 2 mg.KOH/g or less, as measured by ASTM D 4739.
- the poly (hydroxycarboxylic acid) derivatives having a terminal acid group that are preferred in the present invention are those which each have an acid value of less than 70 mg.KOH/g, more preferably less than 60 mg.KOH/g, even more preferably less than 50 mg.KOH/g and most preferably less than 40 mg.KOH/g.
- the base fuel used is a gasoline
- the gasoline may be any gasoline suitable for use in an internal combustion engine of the spark-ignition (petrol) type known in the art.
- the gasoline used as the base fuel in the liquid fuel composition of the present invention may conveniently also be referred to as ⁇ base gasoline' .
- Gasolines typically comprise mixtures of hydrocarbons boiling in the range from 25 to 230 0 C (EN- ISO 3405) , the optimal ranges and distillation curves typically varying according to climate and season of the year.
- the hydrocarbons in a gasoline may be derived by any means known in the art, conveniently the hydrocarbons may be derived in any known manner from straight-run gasoline, synthetically-produced aromatic hydrocarbon mixtures, thermally or catalytically cracked hydrocarbons, hydro-cracked petroleum fractions, catalytically reformed hydrocarbons or mixtures of these.
- the specific distillation curve, hydrocarbon composition, research octane number (RON) and motor octane number (MON) of the gasoline are not critical.
- the research octane number (RON) of the gasoline may be at least 80, for instance in the range of from 80 to 110, preferably the RON of the gasoline will be at least 90, for instance in the range of from 90 to 110, more preferably the RON of the gasoline will be at least 91, for instance in the range of from 91 to 105, even more preferably the RON of the gasoline will be at least 92, for instance in the range of from 92 to 103, even more preferably the RON of the gasoline will be at least 93, for instance in the range of from 93 to 102, and most preferably the RON of the gasoline will be at least 94, for instance in the range of from 94 to 100 (EN 25164);
- the motor octane number (MON) of the gasoline may conveniently be at least 70, for instance in the range of from 70 to
- gasolines comprise components selected from one or more of the following groups; saturated hydrocarbons, olefinic hydrocarbons, aromatic hydrocarbons, and oxygenated hydrocarbons.
- the gasoline may comprise a mixture of saturated hydrocarbons, olefinic hydrocarbons, aromatic hydrocarbons, and, optionally, oxygenated hydrocarbons.
- the olefinic hydrocarbon content of the gasoline is in the range of from 0 to 40 percent by volume based on the gasoline (ASTM D1319); preferably, the olefinic hydrocarbon content of the gasoline is in the range of from 0 to 30 percent by volume based on the gasoline, more preferably, the olefinic hydrocarbon content of the gasoline is in the range of from 0 to 20 percent by volume based on the gasoline.
- the aromatic hydrocarbon content of the gasoline is in the range of from 0 to 70 percent by volume based on the gasoline (ASTM D1319), for instance the aromatic hydrocarbon content of the gasoline is in the range of from 10 to 60 percent by volume based on the gasoline; preferably, the aromatic hydrocarbon content of the gasoline is in the range of from 0 to 50 percent by volume based on the gasoline, for instance the aromatic hydrocarbon content of the gasoline is in the range of from 10 to 50 percent by volume based on the gasoline.
- the benzene content of the gasoline is at most 10 percent by volume, more preferably at most 5 percent by volume, especially at most 1 percent by volume based on the gasoline.
- the gasoline preferably has a low or ultra low sulphur content, for instance at most 1000 ppmw (parts per million by weight), preferably no more than 500 ppmw, more preferably no more than 100, even more preferably no more than 50 and most preferably no more than even 10 ppmw .
- the gasoline also preferably has a low total lead content, such as at most 0.005 g/1, most preferably being lead free - having no lead compounds added thereto (i.e. unleaded) .
- the oxygen content of the gasoline may be up to 35 percent by weight (EN 1601) (e.g. ethanol per se) based on the gasoline.
- the oxygen content of the gasoline may be up to 25 percent by weight, preferably up to 10 percent by weight.
- the oxygenate concentration will have a minimum concentration selected from any one of 0, 0.2, 0.4, 0.6, 0.8, 1.0, and 1.2 percent by weight, and a maximum concentration selected from any one of 5, 4.5, 4.0, 3.5, 3.0, and 2.7 percent by weight.
- oxygenated hydrocarbons examples include alcohols, ethers, esters, ketones, aldehydes, carboxylic acids and their derivatives, and oxygen containing heterocyclic compounds.
- the oxygenated hydrocarbons that may be incorporated into the gasoline are selected from alcohols (such as methanol, ethanol, propanol, iso- propanol, butanol, tert-butanol and iso-butanol) , ethers (preferably ethers containing 5 or more carbon atoms per molecule, e.g., methyl tert-butyl ether) and esters (preferably esters containing 5 or more carbon atoms per molecule) ; a particularly preferred oxygenated hydrocarbon is ethanol.
- oxygenated hydrocarbons When oxygenated hydrocarbons are present in the gasoline, the amount of oxygenated hydrocarbons in the gasoline may vary over a wide range.
- gasolines comprising a major proportion of oxygenated hydrocarbons are currently commercially available in countries such as Brazil and U. S. A, e.g. ethanol per se and E85, as well as gasolines comprising a minor proportion of oxygenated hydrocarbons, e.g. ElO and E5. Therefore, the gasoline may contain up to 100 percent by volume oxygenated hydrocarbons.
- the amount of oxygenated hydrocarbons present in the gasoline is selected from one of the following amounts: up to 85 percent by volume; up to 65 percent by volume; up to 30 percent by volume; up to 20 percent by volume; up to 15 percent by volume; and, up to 10 percent by volume, depending upon the desired final formulation of the gasoline.
- the gasoline may contain at least 0.5, 1.0 or 2.0 percent by volume oxygenated hydrocarbons .
- gasolines which have an olefinic hydrocarbon content of from 0 to 20 percent by volume (ASTM D1319), an oxygen content of from 0 to 5 percent by weight (EN 1601), an aromatic hydrocarbon content of from 0 to 50 percent by volume (ASTM D1319) and a benzene content of at most 1 percent by volume.
- the base gasoline or the gasoline composition of the present invention may conveniently additionally include one or more fuel additive.
- concentration and nature of the fuel additive (s) that may be included in the base gasoline or the gasoline composition of the present invention is not critical.
- suitable types of fuel additives that can be included in the base gasoline or the gasoline composition of the present invention include anti-oxidants, corrosion inhibitors, detergents, dehazers, antiknock additives, metal deactivators, valve-seat recession protectant compounds, dyes, friction modifiers, carrier fluids, diluents and markers. Examples of suitable such additives are described generally in US Patent No. 5,855,629.
- the fuel additives can be blended with one or more diluents or carrier fluids, to form an additive concentrate, the additive concentrate can then be admixed with the base gasoline or the gasoline composition of the present invention.
- the (active matter) concentration of any additives present in the base gasoline or the gasoline composition of the present invention is preferably up to 1 percent by weight, more preferably in the range from 5 to 1000 ppmw, advantageously in the range of from 75 to 300 ppmw, such as from 95 to 150 ppmw.
- the base fuel used is a diesel fuel
- the diesel fuel used as the base fuel in the present invention includes diesel fuels for use in automotive compression ignition engines, as well as in other types of engine such as for example marine, railroad and stationary engines.
- the diesel fuel used as the base fuel in the liquid fuel composition of the present invention may conveniently also be referred to as Miesel base fuel' .
- the diesel base fuel may itself comprise a mixture of two or more different diesel fuel components, and/or be additivated as described below.
- Such diesel fuels will contain one or more base fuels which may typically comprise liquid hydrocarbon middle distillate gas oil (s) , for instance petroleum derived gas oils.
- base fuels may typically comprise liquid hydrocarbon middle distillate gas oil (s) , for instance petroleum derived gas oils.
- Such fuels will typically have boiling points within the usual diesel range of 150 to 400 0 C, depending on grade and use. They will typically have a density from 750 to 1000 kg/m 3 , preferably from 780 to
- non-mineral oil based fuels such as biofuels or Fischer-Tropsch derived fuels
- Fischer-Tropsch fuels may for example be derived from natural gas, natural gas liquids, petroleum or shale oil, petroleum or shale oil processing residues, coal or biomass.
- the amount of Fischer-Tropsch derived fuel used in the diesel fuel may be from 0% to 100%v of the overall diesel fuel, preferably from 5% to 100%v, more preferably from 5% to 75%v. It may be desirable for such a diesel fuel to contain 10%v or greater, more preferably 20%v or greater, still more preferably 30%v or greater, of the Fischer-Tropsch derived fuel. It is particularly preferred for such diesel fuels to contain 30 to 75%v, and particularly 30 or 70%v, of the Fischer-Tropsch derived fuel.
- the balance of the diesel fuel is made up of one or more other diesel fuel components.
- Such a Fischer-Tropsch derived fuel component is any fraction of the middle distillate fuel range, which can be isolated from the (optionally hydrocracked) Fischer-Tropsch synthesis product. Typical fractions will boil in the naphtha, kerosene or gas oil range. Preferably, a Fischer-Tropsch product boiling in the kerosene or gas oil range is used because these products are easier to handle in for example domestic environments. Such products will suitably comprise a fraction larger than 90 wt% which boils between 160 and 400 0 C, preferably to about 370 0 C.
- Fischer- Tropsch derived kerosene and gas oils are described in EP-A-0583836, WO-A-97/14768 , WO-A-97/14769, WO-A-O 0/11116, WO-A-00/11117, WO-A-01/83406, WO-A-01/83648, WO-A-01/83647 , WO-A-01/83641 , WO-A-00/20535, WO-A-00/20534 , EP-A-1101813, US-A-5766274 , US-A-5378348, US-A-5888376 and US-A-6204426.
- the Fischer-Tropsch product will suitably contain more than 80 wt% and more suitably more than 95 wt% iso and normal paraffins and less than 1 wt% aromatics, the balance being naphthenics compounds.
- the content of sulphur and nitrogen will be very low and normally below the detection limits for such compounds. For this reason the sulphur content of a diesel fuel composition containing a Fischer-Tropsch product may be very low.
- the diesel fuel composition preferably contains no more than 5000ppmw sulphur, more preferably no more than 500ppmw, or no more than 350ppmw, or no more than 150ppmw, or no more than lOOppmw, or no more than 70ppmw, or no more than 50ppmw, or no more than 30ppmw, or no more than 20ppmw, or most preferably no more than 15ppmw sulphur.
- the diesel base fuel may itself be additivated (additive-containing) or unadditivated (additive-free) . If additivated, e.g. at the refinery, it will contain minor amounts of one or more additives selected for example from anti-static agents, pipeline drag reducers, flow improvers (e.g. ethylene/vinyl acetate copolymers or acrylate/maleic anhydride copolymers) , lubricity additives, antioxidants and wax anti-settling agents.
- additives selected for example from anti-static agents, pipeline drag reducers, flow improvers (e.g. ethylene/vinyl acetate copolymers or acrylate/maleic anhydride copolymers) , lubricity additives, antioxidants and wax anti-settling agents.
- Detergent-containing diesel fuel additives are known and commercially available. Such additives may be added to diesel fuels at levels intended to reduce, remove, or slow the build up of engine deposits.
- detergents suitable for use in diesel fuel additives for the present purpose include polyolefin substituted succinimides or succinamides of polyamines, for instance polyisobutylene succinimides or polyisobutylene amine succinamides, aliphatic amines, Mannich bases or amines and polyolefin (e.g. polyisobutylene) maleic anhydrides.
- polyolefin substituted succinimides or succinamides of polyamines for instance polyisobutylene succinimides or polyisobutylene amine succinamides, aliphatic amines, Mannich bases or amines and polyolefin (e.g. polyisobutylene) maleic anhydrides.
- Succinimide dispersant additives are described for example in
- Particularly preferred are polyolefin substituted succinimides such as polyisobutylene succinimides.
- the diesel fuel additive mixture may contain other components in addition to the detergent.
- lubricity enhancers e.g. alkoxylated phenol formaldehyde polymers
- anti-foaming agents e.g. polyether-modified polysiloxanes
- ignition improvers cetane improvers
- anti-rust agents e.g. 2-ethylhexyl nitrate (EHN), cyclohexyl nitrate, di-tert-butyl peroxide and those disclosed in US-A-4208190 at column 2, line 27 to column 3, line 21
- anti-rust agents e.g.
- succinic acid derivative having on at least one of its alpha-carbon atoms an unsubstituted or substituted aliphatic hydrocarbon group containing from 20 to 500 carbon atoms, e.g. the pentaerythritol diester of polyisobutylene-substituted succinic acid) ; corrosion inhibitors; reodorants; anti-wear additives; anti-oxidants (e.g. phenolics such as
- 6-di-tert-butylphenol, or phenylenediamines such as N, N ' -di-sec-butyl-p-phenylenediamine
- metal deactivators such as N, N ' -di-sec-butyl-p-phenylenediamine
- combustion improvers such as N, N ' -di-sec-butyl-p-phenylenediamine
- static dissipator additives such as cold flow improvers
- wax anti-settling agents such as N, N ' -di-sec-butyl-p-phenylenediamine
- the diesel fuel additive mixture may contain a lubricity enhancer, especially when the diesel fuel composition has a low (e.g. 500 ppmw or less) sulphur content.
- the lubricity enhancer is conveniently present at a concentration of less than 1000 ppmw, preferably between 50 and 1000 ppmw, more preferably between 70 and 1000 ppmw.
- Suitable commercially available lubricity enhancers include ester- and acid-based additives.
- Other lubricity enhancers are described in the patent literature, in particular in connection with their use in low sulphur content diesel fuels, for example in: - the paper by Danping Wei and H. A. Spikes, "The
- the diesel fuel composition may also be preferred for the diesel fuel composition to contain an anti-foaming agent, more preferably in combination with an anti-rust agent and/or a corrosion inhibitor and/or a lubricity enhancing additive .
- the (active matter) concentration of each such additive component in the additivated diesel fuel composition is preferably up to 10000 ppmw, more preferably in the range from 0.1 to 1000 ppmw, advantageously from 0.1 to 300 ppmw, such as from 0.1 to 150 ppmw .
- the (active matter) concentration of any dehazer in the diesel fuel composition will preferably be in the range from 0.1 to 20 ppmw, more preferably from 1 to 15 ppmw, still more preferably from 1 to 10 ppmw, advantageously from 1 to 5 ppmw.
- the (active matter) concentration of any ignition improver present will preferably be 2600 ppmw or less, more preferably 2000 ppmw or less, conveniently from 300 to 1500 ppmw.
- the (active matter) concentration of any detergent in the diesel fuel composition will preferably be in the range from 5 to 1500 ppmw, more preferably from 10 to 750 ppmw, most preferably from 20 to 500 ppmw.
- the fuel additive mixture will typically contain a detergent, optionally together with other components as described above, and a diesel fuel-compatible diluent, which may be a mineral oil, a solvent such as those sold by Shell companies under the trade mark "SHELLSOL", a polar solvent such as an ester and, in particular, an alcohol, e.g. hexanol, 2-ethylhexanol, decanol, isotridecanol and alcohol mixtures such as those sold by Shell companies under the trade mark "LINEVOL”, especially LINEVOL 79 alcohol which is a mixture of 07-9 primary alcohols, or a C]_2-14 alcohol mixture which is commercially available.
- a diesel fuel-compatible diluent which may be a mineral oil, a solvent such as those sold by Shell companies under the trade mark "SHELLSOL”, a polar solvent such as an ester and, in particular, an alcohol, e.g. hexanol, 2-ethylhexanol, de
- the total content of the additives in the diesel fuel composition may be suitably between 0 and 10000 ppmw and preferably below 5000 ppmw.
- amounts (concentrations, % vol, ppmw, % wt) of components are of active matter, i.e. exclusive of volatile solvents/diluent materials.
- the liquid fuel composition of the present invention is produced by admixing the one or more poly (hydroxycarboxylic acid) derivative having a terminal acid group with a base fuel suitable for use in an internal combustion engine. If the base fuel to which the one or more poly (hydroxycarboxylic acid) derivative having a terminal acid group is admixed is a gasoline, then the liquid fuel composition produced is a gasoline composition; likewise, if the base fuel to which the one or more poly (hydroxycarboxylic acid) derivative having a terminal acid group is admixed is a diesel fuel, then the liquid fuel composition produced is a diesel fuel composition .
- the amount of the one or more poly (hydroxycarboxylic acid) derivative having a terminal acid group present in the liquid fuel composition of the present invention is at least 1 ppmw (part per million by weight) , based on the overall weight of the liquid fuel composition. More preferably, the amount of the one or more poly (hydroxycarboxylic acid) derivative having a terminal acid group present in the liquid fuel composition of the present invention additionally accords with one or more of the parameters (i) to (xx) listed below:
- the amount of the one or more poly (hydroxycarboxylic acid) derivative having a terminal acid group present in the liquid fuel composition of the present invention may also be at least 200 ppmw, at least 300 ppmw, at least 400 ppmw, at least 500 ppmw, or even at least 1000 ppmw.
- the use of the one or more poly (hydroxycarboxylic acid) derivative having a terminal acid group in the liquid fuel compositions can provide significant benefits in terms of improved lubricity of the liquid fuel composition, in particular when the liquid fuel composition is gasoline, relative to the liquid base fuel.
- improve/improving lubricity used herein, it is meant that the wear scar produced using a high frequency reciprocating rig (HFRR) is reduced.
- HFRR high frequency reciprocating rig
- the use of the one or more poly (hydroxycarboxylic acid) derivative having a terminal acid group in liquid fuel compositions can also provide benefits in terms of engine cleanliness, in particular in terms of improved inlet valve deposit keep clean and/or injector nozzle keep clean performance, of an internal combustion engine being fuelled by the liquid fuel composition of the present invention relative to the internal combustion engine being fuelled by the liquid base fuel.
- improved/improving inlet valve deposit keep clean performance it is meant that the weight of deposit formed on the inlet valve of the engine is reduced relative to the base fuel not containing the one or more poly (hydroxycarboxylic acid) derivative having a terminal acid group.
- improve/improving injector nozzle keep clean performance it is meant that the amount of deposit formed on the injector nozzle of the engine is reduced as measured by the loss of engine torque.
- liquid fuel compositions can also provide benefits in terms improved fuel economy of an internal combustion engine being fuelled by the liquid fuel composition of the present invention relative to the internal combustion engine being fuelled by the liquid base fuel.
- the present invention therefore also provides a method of improving the lubricity of a liquid base fuel suitable for use in an internal combustion engine, comprising admixing one or more poly (hydroxycarboxylic acid) derivative having a terminal acid group with a major portion of the liquid base fuel suitable for use in an internal combustion engine; a method of improving the inlet valve deposit clean up performance of a liquid base fuel suitable for use in an internal combustion engine, comprising admixing one or more poly (hydroxycarboxylic acid) derivative having a terminal acid group with a major portion of the liquid base fuel suitable for use in an internal combustion engine; a method of improving the injector nozzle keep clean performance of a liquid base fuel suitable for use in an internal combustion engine, comprising admixing one or more poly (hydroxycarboxylic acid) derivative having a terminal acid group with a major portion of the liquid base fuel suitable for use in an internal combustion engine; and, a method of improving the fuel economy performance of a liquid base fuel suitable for use in an internal combustion engine, comprising admixing one or more
- the use of the one or more poly (hydroxycarboxylic acid) derivative having a terminal acid group in liquid fuel compositions can also provide benefits in terms improving the lubricant performance of an internal combustion engine being fuelled by the liquid fuel composition of the present invention relative to the internal combustion engine being fuelled by the liquid base fuel.
- the improvement in the lubricant performance of the internal combustion engine fuelled by a liquid fuel composition according to the present invention can be observed by the a reduction in the levels of sludge and varnish on specific engine parts, such as sludge on rocker arm covers, cam baffles, timing chain covers, oil pans, oil pan baffles, and valve decks, and varnish on piston skirts and cam baffles.
- the use of the one or more poly (hydroxycarboxylic acid) derivative having a terminal acid group in a gasoline compositions can provide benefits in terms inhibiting specific sludge and varnish deposit formation, as measured by ASTM D 6593-07, of an internal combustion engine being fuelled by the gasoline composition of the present invention relative to the internal combustion engine being fuelled by the gasoline base fuel. Therefore, the present invention also provides a method of improving the performance of the lubricant of an internal combustion engine, said method comprising fuelling an internal combustion engine containing the engine lubricant with a liquid fuel composition according to the present invention.
- the present invention further provides a method of operating an internal combustion engine, which method involves introducing into a combustion chamber of the engine a liquid fuel composition according to the present invention.
- the poly (hydroxycarboxylic acid) derivatives having a terminal acid group described above may also be conveniently used in lubricating compositions, in particular in automotive engine lubricating oil compositions.
- WO 2007/128740 which is incorporated herein by reference, discloses suitable lubricating base oils and additives to which the poly (hydroxycarboxylic acid) derivatives having a terminal acid group described above may be admixed. Therefore, the present invention further provides a lubricating composition comprising: a base oil; and poly (hydroxycarboxylic acid) derivatives having a terminal acid group as described above.
- the poly (hydroxycarboxylic acid) derivatives having a terminal acid group is present in the lubricating composition of the present invention in an amount in the range of from 0.1 to 10.0 wt.%, more preferably in an amount in the range of from 0.1 to 5.0 wt. %, based on the total weight of the lubricating composition.
- the composition comprises less than 5.0 wt.%, preferably less than 2.0 wt.% of the poly (hydroxycarboxylic acid) derivatives having a terminal acid group, based on the total weight of the lubricant composition.
- the lubricating composition has a relatively low phosphorus content such as below 0.12 wt.% (according to ASTM D 5185) .
- the composition has a phosphorus content of less than 0.08 wt.%.
- the composition has a phosphorus content of above 0.06 wt.%.
- the composition has a sulphur content of less than 0.6 wt.% (according to ASTM D 5185) .
- composition has a chlorine content of less than 200 ppm (according to ASTM D 808) .
- the composition has an ash content of below 2.0 wt.% (according to ASTM D 874) .
- the composition comprises a zinc dialkyl dithiophosphate (ZDDP) compound.
- ZDDP zinc dialkyl dithiophosphate
- the ZDDP compound is present in an amount of 0.01-1.5 wt.%, preferably 0.4-1.0 wt.%.
- the ZDDP compound may have been made from primary, secondary, tertiary alcohols or mixtures thereof, preferably containing less than 12 carbon atoms.
- the ZDDP compound has been made from secondary alcohols containing 3 to 8 carbon atoms .
- the base oil used in the lubricating composition and various conventional mineral oils, synthetic oils as well as naturally derived esters such as vegetable oils may be conveniently used.
- the base oil used may conveniently comprise mixtures of one or more mineral oils and/or one or more synthetic oils; thus, the term “base oil” may refer to a mixture containing more than one base oil.
- Mineral oils include liquid petroleum oils and solvent-treated or acid-treated mineral lubricating oil of the paraffinic, naphthenic, or mixed paraffinic/naphthenic type which may be further refined by hydrofinishing processes and/or dewaxing.
- Suitable base oils for use in the lubricating oil composition are Group I-III mineral base oils, Group IV poly-alpha olefins (PAOs) , Group II-III Fischer-Tropsch derived base oils and mixtures thereof.
- Group I lubricating oil base oils according to the definitions of American Petroleum Institute (API) for categories I-IV. These API categories are defined in API Publication 1509, 16th Edition, Appendix E, April 2007.
- API American Petroleum Institute
- Fischer-Tropsch derived base oils are known in the art.
- Fischer-Tropsch derived is meant that a base oil is, or is derived from, a synthesis product of a Fischer-Tropsch process.
- a Fischer-Tropsch derived base oil may also be referred to as a GTL (Gas-To- Liquids) base oil.
- Suitable Fischer-Tropsch derived base oils that may be conveniently used as the base oil in the lubricating composition are those as for example disclosed in EP 0 776 959, EP 0 668 342, WO 97/21788, WO 00/15736, WO 00/14188, WO 00/14187, WO 00/14183, WO 00/14179, WO 00/08115, WO 99/41332, EP 1 029 029, WO 01/18156 and WO 01/57166.
- Synthetic oils include hydrocarbon oils such as olefin oligomers (including polyalphaolefin base oils; PAOs) , dibasic acid esters, polyol esters, polyalkylene glycols (PAGs) , alkyl naphthalenes and dewaxed waxy isomerates.
- hydrocarbon oils sold by the Shell Group under the designation "Shell XHVI” (trade mark) may be conveniently used.
- Poly-alpha olefin base oils (PAOs) and their manufacture are well known in the art.
- Preferred poly- alpha olefin base oils that may be used in the lubricating compositions may be derived from linear C 2 to C 32 , preferably C 6 to Ci 6 , alpha olefins.
- Particularly preferred feedstocks for said poly-alpha olefins are 1- octene, 1-decene, 1-dodecene and 1-tetradecene .
- the total amount of base oil incorporated in the lubricating composition is preferably present in an amount in the range of from 60 to 99 wt.%, more preferably in an amount in the range of from 65 to 98 wt.% and most preferably in an amount in the range of from 70 to 95 wt.%, with respect to the total weight of the lubricating composition.
- the finished lubricating composition has a kinematic viscosity in the range of from 2 to 80 mm 2 /s at 100 0 C, more preferably in the range of from 3 to 70 mm 2 /s, most preferably in the range of from 4 to 50 mm 2 /s .
- the lubricating composition may further comprise additional additives such as anti-wear additives, antioxidants, dispersants, detergents, friction modifiers, viscosity index improvers, pour point depressants, corrosion inhibitors, defoaming agents and seal fix or seal compatibility agents.
- additional additives such as anti-wear additives, antioxidants, dispersants, detergents, friction modifiers, viscosity index improvers, pour point depressants, corrosion inhibitors, defoaming agents and seal fix or seal compatibility agents.
- the detergent if present, is selected from phenate- and sulphonate-type detergents; accordingly.
- the lubricating compositions may be conveniently prepared by admixing the poly (hydroxycarboxylic acid) derivatives having a terminal acid group described above, and, optionally, any further additives that are usually present in lubricating compositions, for example as herein before described, with mineral and/or synthetic base oil.
- poly (hydroxycarboxylic acid) derivatives having a terminal acid group described above can provide benefits in terms of improved lubricity of the lubricating composition.
- poly (hydroxycarboxylic acid) derivatives having a terminal acid group described above in lubricating compostions can provide benefits in terms inhibiting specific sludge and varnish deposit formation, as measured by ASTM D 6593-07.
- poly (hydroxycarboxylic acid) derivatives having a terminal acid group described above can provide benefits in terms improving the fuel economy of an internal combustion engine lubricated by the lubricating composition .
- the present invention will be further understood from the following examples. Unless otherwise stated, all amounts and concentrations disclosed in the examples are based on weight of the fully formulated fuel composition. Examples
- CH-2C a commercially available hyperdispersants
- the CH-2C hyperdispersant had an average molecular weight of 1368, a measured sulphur content of 0.61 ppmw, a measured nitrogen content of 0.05 %wt .
- Figure 1 a general chemical structure of the type given in Figure 1 below:
- Examples 1 to 21 and Comparative Examples A to D The CH-2C hyperdispersant described above was blended into a base fuel selected from the gasoline, diesel, GTL diesel and Swedish Class I diesel base fuels described in Tables 1 and 2 below, in various amounts.
- the lubricity of the diesel fuel compositions was determined using the HFRR test used described in ISO 12156-1.
- the lubricity of the gasoline compositions was determined by using a modified HFRR test.
- the modified HFRR test is based on ISO 12156-1 using a PCS Instruments HFRR supplemented with the PCS Instruments Gasoline Conversion Kit, and using a fluid volume of 15.0 ml (+/- 0.2 ml), a fluid temperature of 25.0 0 C (+/- 1 0 C), and wherein a PTFE cover is used to cover the test sample in order to minimise evaporation.
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Combustion & Propulsion (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Lubricants (AREA)
Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BRPI0916886A BRPI0916886A2 (en) | 2008-07-31 | 2009-07-29 | liquid fuel, and lubricant compositions, and method for operating an internal combustion engine. |
CN200980130657.7A CN102112587B (en) | 2008-07-31 | 2009-07-29 | Liquid fuel compositions |
CA2732160A CA2732160A1 (en) | 2008-07-31 | 2009-07-29 | Liquid fuel compositions |
AU2009275892A AU2009275892B2 (en) | 2008-07-31 | 2009-07-29 | Liquid fuel compositions |
EP09802517A EP2307529A1 (en) | 2008-07-31 | 2009-07-29 | Liquid fuel compositions |
JP2011520502A JP2011529517A (en) | 2008-07-31 | 2009-07-29 | Liquid fuel composition |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP08161573 | 2008-07-31 | ||
EP08161573.4 | 2008-07-31 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2010012763A1 true WO2010012763A1 (en) | 2010-02-04 |
Family
ID=40159223
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2009/059795 WO2010012763A1 (en) | 2008-07-31 | 2009-07-29 | Liquid fuel compositions |
Country Status (9)
Country | Link |
---|---|
US (1) | US20100024287A1 (en) |
EP (1) | EP2307529A1 (en) |
JP (1) | JP2011529517A (en) |
CN (1) | CN102112587B (en) |
AU (1) | AU2009275892B2 (en) |
BR (1) | BRPI0916886A2 (en) |
CA (1) | CA2732160A1 (en) |
SG (1) | SG193166A1 (en) |
WO (1) | WO2010012763A1 (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2012163935A2 (en) | 2011-05-30 | 2012-12-06 | Shell Internationale Research Maatschappij B.V. | Liquid fuel compositions |
WO2012177537A1 (en) | 2011-06-21 | 2012-12-27 | The Lubrizol Corporation | Lubricating composition containing a dispersant |
WO2012177549A1 (en) | 2011-06-21 | 2012-12-27 | The Lubrizol Corporation | Lubricating composition containing a dispersant |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BR112014015253A2 (en) * | 2011-12-21 | 2017-08-22 | Shell Internationale Res Maaschappij B V | METHOD FOR INHIBITING FOAM FORMATION IN A MIXTURE, COMPOSITION, AND, FOAM-INHIBITED MIXTURE |
US9335049B2 (en) * | 2012-06-07 | 2016-05-10 | United Technologies Corporation | Combustor liner with reduced cooling dilution openings |
JP5912971B2 (en) * | 2012-07-30 | 2016-04-27 | 昭和シェル石油株式会社 | Lubricating oil composition for internal combustion engines |
US8721782B1 (en) * | 2013-02-08 | 2014-05-13 | Xerox Corporation | Carbon black pigmented solid phase change ink formulations |
EP2963097A4 (en) * | 2013-03-01 | 2017-03-22 | TonenGeneral Sekiyu Kabushiki Kaisha | Fuel oil |
Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0127325A2 (en) * | 1983-05-24 | 1984-12-05 | Imperial Chemical Industries Plc | Dispersing agent |
US4512776A (en) * | 1983-12-23 | 1985-04-23 | Exxon Research And Engineering Co. | Ionic polymer-polylactone compositions as flow improvers for oils and fuels |
EP0164817A2 (en) * | 1984-03-21 | 1985-12-18 | Imperial Chemical Industries Plc | Surfactant |
EP0194718A2 (en) * | 1985-03-15 | 1986-09-17 | Shell Internationale Researchmaatschappij B.V. | Lubricating-oil compositions |
JPH02294392A (en) * | 1989-05-08 | 1990-12-05 | Katayama Chem Works Co Ltd | Dispersion of calcium carbonate |
JPH1192773A (en) * | 1997-09-24 | 1999-04-06 | Yushiro Chem Ind Co Ltd | Lubricating additive for gas oil |
JPH11228977A (en) * | 1998-02-17 | 1999-08-24 | Yushiro Chem Ind Co Ltd | Lubricating additive for gas oil |
WO2000034418A1 (en) * | 1998-12-04 | 2000-06-15 | Infineum Holdings B.V. | Fuel additive and fuel composition containing the same |
WO2006054044A1 (en) * | 2004-11-19 | 2006-05-26 | Croda International Plc | Lubricating composition comprising a polyester dispersant |
WO2007014266A2 (en) * | 2005-07-25 | 2007-02-01 | C.M. Intellectual Property And Research, Inc. | Fuel and lubricant additives and methods for improving fuel economy and vehicle emissions |
Family Cites Families (28)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL296139A (en) * | 1963-08-02 | |||
NL145565B (en) * | 1965-01-28 | 1975-04-15 | Shell Int Research | PROCESS FOR PREPARING A LUBRICANT COMPOSITION. |
US3574576A (en) * | 1965-08-23 | 1971-04-13 | Chevron Res | Distillate fuel compositions having a hydrocarbon substituted alkylene polyamine |
US3822209A (en) * | 1966-02-01 | 1974-07-02 | Ethyl Corp | Lubricant additives |
US3755433A (en) * | 1971-12-16 | 1973-08-28 | Texaco Inc | Ashless lubricating oil dispersant |
US3996059A (en) * | 1971-12-30 | 1976-12-07 | Imperial Chemical Industries Limited | Dispersing agents |
US4208190A (en) * | 1979-02-09 | 1980-06-17 | Ethyl Corporation | Diesel fuels having anti-wear properties |
DE3066683D1 (en) * | 1979-07-26 | 1984-03-29 | Ici Plc | A dispersible pigment composition, its preparation and use in the coloration of thermoplastic materials and paints |
US4512903A (en) * | 1983-06-23 | 1985-04-23 | Texaco Inc. | Lubricant compositions containing amides of hydroxy-substituted aliphatic acids and fatty amines |
US4525288A (en) * | 1983-08-15 | 1985-06-25 | Texaco Inc. | Lubricants containing hydroxyalkoxy acid amides of alkyl amines as friction reducers |
GB8429686D0 (en) * | 1984-11-23 | 1985-01-03 | Int Paint Plc | Dispersants |
GB8602333D0 (en) * | 1986-01-30 | 1986-03-05 | Ici Plc | Dispersing agents |
GB8701705D0 (en) * | 1987-01-27 | 1987-03-04 | Ici Plc | Corrosion inhibition |
JPH0819351B2 (en) * | 1988-06-09 | 1996-02-28 | サカタインクス株式会社 | Pigment dispersant and offset printing ink composition using the same |
US5149454A (en) * | 1991-05-20 | 1992-09-22 | General Motors Corporation | Electrorheological compositions including am5-11 O8-17 |
US5139692A (en) * | 1991-05-20 | 1992-08-18 | General Motors Corporation | Electrorheological compositions including an amine-terminated polyester steric stabilizer |
US5490864A (en) * | 1991-08-02 | 1996-02-13 | Texaco Inc. | Anti-wear lubricity additive for low-sulfur content diesel fuels |
US5378348A (en) * | 1993-07-22 | 1995-01-03 | Exxon Research And Engineering Company | Distillate fuel production from Fischer-Tropsch wax |
TW477784B (en) * | 1996-04-26 | 2002-03-01 | Shell Int Research | Alkoxy acetic acid derivatives |
US5888376A (en) * | 1996-08-23 | 1999-03-30 | Exxon Research And Engineering Co. | Conversion of fischer-tropsch light oil to jet fuel by countercurrent processing |
DE19634605B4 (en) * | 1996-08-27 | 2005-02-03 | Schill + Seilacher "Struktol" Ag | Use of sugar amides as EP additives and EP additives containing gluconic and / or glucoheptonic acid amides |
US5858029A (en) * | 1997-01-13 | 1999-01-12 | Mobil Oil Corporation | Friction reducing additives for fuels and lubricants |
US5766274A (en) * | 1997-02-07 | 1998-06-16 | Exxon Research And Engineering Company | Synthetic jet fuel and process for its production |
JPH11293262A (en) * | 1998-04-03 | 1999-10-26 | Yushiro Chem Ind Co Ltd | Lubricating additive for gas oil and gas oil composition |
FR2798136B1 (en) * | 1999-09-08 | 2001-11-16 | Total Raffinage Distribution | NEW HYDROCARBON BASE OIL FOR LUBRICANTS WITH VERY HIGH VISCOSITY INDEX |
US6204426B1 (en) * | 1999-12-29 | 2001-03-20 | Chevron U.S.A. Inc. | Process for producing a highly paraffinic diesel fuel having a high iso-paraffin to normal paraffin mole ratio |
GB2368848B (en) * | 2000-09-21 | 2002-11-27 | Ciba Sc Holding Ag | Lubricants with 5-tert.-butyl-hydroxy-3-methylphenyl substituted fatty acid esters |
US7635669B2 (en) * | 2004-10-04 | 2009-12-22 | Afton Chemical Corportation | Compositions comprising at least one hydroxy-substituted carboxylic acid |
-
2009
- 2009-07-29 BR BRPI0916886A patent/BRPI0916886A2/en not_active IP Right Cessation
- 2009-07-29 WO PCT/EP2009/059795 patent/WO2010012763A1/en active Application Filing
- 2009-07-29 US US12/511,710 patent/US20100024287A1/en not_active Abandoned
- 2009-07-29 CA CA2732160A patent/CA2732160A1/en not_active Abandoned
- 2009-07-29 SG SG2013058177A patent/SG193166A1/en unknown
- 2009-07-29 CN CN200980130657.7A patent/CN102112587B/en not_active Expired - Fee Related
- 2009-07-29 JP JP2011520502A patent/JP2011529517A/en active Pending
- 2009-07-29 AU AU2009275892A patent/AU2009275892B2/en not_active Ceased
- 2009-07-29 EP EP09802517A patent/EP2307529A1/en not_active Withdrawn
Patent Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0127325A2 (en) * | 1983-05-24 | 1984-12-05 | Imperial Chemical Industries Plc | Dispersing agent |
US4512776A (en) * | 1983-12-23 | 1985-04-23 | Exxon Research And Engineering Co. | Ionic polymer-polylactone compositions as flow improvers for oils and fuels |
EP0164817A2 (en) * | 1984-03-21 | 1985-12-18 | Imperial Chemical Industries Plc | Surfactant |
EP0194718A2 (en) * | 1985-03-15 | 1986-09-17 | Shell Internationale Researchmaatschappij B.V. | Lubricating-oil compositions |
JPH02294392A (en) * | 1989-05-08 | 1990-12-05 | Katayama Chem Works Co Ltd | Dispersion of calcium carbonate |
JPH1192773A (en) * | 1997-09-24 | 1999-04-06 | Yushiro Chem Ind Co Ltd | Lubricating additive for gas oil |
JPH11228977A (en) * | 1998-02-17 | 1999-08-24 | Yushiro Chem Ind Co Ltd | Lubricating additive for gas oil |
WO2000034418A1 (en) * | 1998-12-04 | 2000-06-15 | Infineum Holdings B.V. | Fuel additive and fuel composition containing the same |
WO2006054044A1 (en) * | 2004-11-19 | 2006-05-26 | Croda International Plc | Lubricating composition comprising a polyester dispersant |
WO2007014266A2 (en) * | 2005-07-25 | 2007-02-01 | C.M. Intellectual Property And Research, Inc. | Fuel and lubricant additives and methods for improving fuel economy and vehicle emissions |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2012163935A2 (en) | 2011-05-30 | 2012-12-06 | Shell Internationale Research Maatschappij B.V. | Liquid fuel compositions |
US20140338624A1 (en) * | 2011-05-30 | 2014-11-20 | Shell Oil Company | Liquid fuel compositions |
WO2012177537A1 (en) | 2011-06-21 | 2012-12-27 | The Lubrizol Corporation | Lubricating composition containing a dispersant |
WO2012177549A1 (en) | 2011-06-21 | 2012-12-27 | The Lubrizol Corporation | Lubricating composition containing a dispersant |
US9249699B2 (en) | 2011-06-21 | 2016-02-02 | The Lubrizol Corporation | Lubricating composition containing a dispersant |
Also Published As
Publication number | Publication date |
---|---|
EP2307529A1 (en) | 2011-04-13 |
BRPI0916886A2 (en) | 2016-02-10 |
CA2732160A1 (en) | 2010-02-04 |
AU2009275892A1 (en) | 2010-02-04 |
CN102112587A (en) | 2011-06-29 |
AU2009275892B2 (en) | 2013-09-12 |
JP2011529517A (en) | 2011-12-08 |
SG193166A1 (en) | 2013-09-30 |
US20100024287A1 (en) | 2010-02-04 |
CN102112587B (en) | 2014-03-26 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
AU2009275885B2 (en) | Liquid fuel compositions | |
AU2009275892B2 (en) | Liquid fuel compositions | |
JP3609081B2 (en) | Alkoxyamine salts of carboxylic acids which are friction modifiers as additives for fuel compositions and methods of use thereof | |
US20120304531A1 (en) | Liquid fuel compositions | |
AU2008313698A1 (en) | Functional fluids for internal combustion engines | |
CA2729355A1 (en) | Liquid fuel compositions | |
CA2424759A1 (en) | Friction modifier additives for fuel compositions and methods of use thereof | |
US11499107B2 (en) | Liquid fuel compositions | |
US20130000583A1 (en) | Liquid fuel compositions | |
US20130000584A1 (en) | Liquid fuel compositions | |
WO2023052286A1 (en) | Fuel compositions |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
WWE | Wipo information: entry into national phase |
Ref document number: 200980130657.7 Country of ref document: CN |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 09802517 Country of ref document: EP Kind code of ref document: A1 |
|
REEP | Request for entry into the european phase |
Ref document number: 2009802517 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2009802517 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2009275892 Country of ref document: AU |
|
ENP | Entry into the national phase |
Ref document number: 2732160 Country of ref document: CA |
|
ENP | Entry into the national phase |
Ref document number: 2009275892 Country of ref document: AU Date of ref document: 20090729 Kind code of ref document: A |
|
ENP | Entry into the national phase |
Ref document number: 2011520502 Country of ref document: JP Kind code of ref document: A |
|
WWE | Wipo information: entry into national phase |
Ref document number: 12011500225 Country of ref document: PH |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
WWE | Wipo information: entry into national phase |
Ref document number: 1350/CHENP/2011 Country of ref document: IN |
|
ENP | Entry into the national phase |
Ref document number: PI0916886 Country of ref document: BR Kind code of ref document: A2 Effective date: 20110128 |