Classifications

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  • 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
  • C10L10/04—Use of additives to fuels or fires for particular purposes for minimising corrosion or incrustation
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  • C10L1/00—Liquid carbonaceous fuels
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  • C10L1/00—Liquid carbonaceous fuels
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  • 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
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  • C10L1/00—Liquid carbonaceous fuels
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  • C10L1/14—Organic compounds
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  • C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
  • C10L1/1905—Esters ester radical containing compounds; ester ethers; carbonic acid esters of di- or polycarboxylic acids
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  • 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
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  • 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
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  • 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
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  • 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
  • C10L1/2225—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates hydroxy containing
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  • C10L1/00—Liquid carbonaceous fuels
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  • 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
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  • 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
  • C10L1/2383—Polyamines or polyimines, or derivatives thereof (poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C)
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  • 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
  • C10L1/2383—Polyamines or polyimines, or derivatives thereof (poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C)
  • C10L1/2387—Polyoxyalkyleneamines (poly)oxyalkylene amines and derivatives thereof (substituted by a macromolecular group containing 30C)
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  • 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
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  • 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
  • C10L1/1985—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 polyethers, e.g. di- polygylcols and derivatives; ethers - esters

Definitions

• the present invention relates to hydrocarbyl succinic acid and hydrocarbylsuccinic acid derivatives as friction modifiers for fuels.
• Carburettors and inlet systems of Otto engines, and also injection systems for fuel proportioning, are subjected to increasing load due to contamination caused by dust particles from the air, unburned hydrocarbon residues from the combustion chamber and crankcase breather gases passed to the carburettor.
• valve seat recession occurs in the case of Otto engines of less recent design when fuelled with unleaded gasolines.
• anti-valve seat recession additives based on alkali metal or alkaline earth metal compounds have been developed.
• gasolines For trouble-free running, modern Otto engines require automotive fuels having a complex set of properties which can only be guaranteed when use is made of appropriate gasoline additives.
• Such gasolines usually consist of a complex mixture of chemical compounds and are characterized by physical parameters.
• the interrelationship between gasolines and appropriate additives in known fuel compositions is still unsatisfactory as regards their detergent action or their pollution-abating properties and their anti-valve seat recession action.
• WO 03/070860 describes a friction modifier of the formula R 1 -L-N(R 2 R 3 ), wherein R 1 is a hydrocarbyl group and L is a linker.
• Preferred compounds of that formula are polyisobutenylsuccinimides, i.e. R 1 is a polyisobutenyl radical and L is a succinic acid derived group.
• EP-A-1424322 describes polyisobutenylsuccinic acids or derivatives thereof.
• the compounds are used, inter alia, as detergents or dispersants for lube oil or fuels or as friction modifiers for automatic transmission fluids and continuous variable transmissions.
• compounds of formula (I) are used as friction reducing agents in fuels.
• the invention is further related to a fuel composition containing a fuel as major component and at least one compound of the formula (I) as defined above and optionally at least one further additive.
• the invention is related to an additive concentrate, comprising at least one compound of the formula (I) as defined above and at least one diluent and optionally at least one further additive.
• the invention is related to a method for producing a fuel composition with improved friction properties, where a fuel or a commercial fuel composition is additized with at least one compound of the formula (I) as defined above or with the additive concentrate as defined above.
• the organic moieties mentioned in the above definitions of the variables are - like the term halogen - collective terms for individual listings of the individual group members.
• the prefix C n -C m indicates in each case the possible number of carbon atoms in the group.
• aliphatic hydrocarbyl group containing less than 15% quaternary carbon atoms denotes a branched or linear aliphatic hydrocarbyl group where less than 15%, preferably less than 10% and more preferably less than 5%, e.g. less than 3% or less than 2 %, of the carbon atoms are quaternary.
• An aliphatic hydrocarbyl group is an acyclic radical essentially composed of carbon atoms and hydrogen atoms, e.g. an alkyl, alkenyl or alkynyl group.
• a quaternary carbon atom is a (sp 3 ) carbon atom carrying four radicals different from hydrogen.
• the term denotes an araliphatic hydrocarbyl group, i.e. an aliphatic hydrocarbyl group carrying at least one aryl substituent, e.g. an alkenylaryl group or an alkylaryl group, where preferably less than 15%, more preferably less than 10% and even more preferably less than 5%, e.g. less than 3% or less than 2%, of the carbon atoms of the aliphatic moiety are quaternary.
• an araliphatic hydrocarbyl group i.e. an aliphatic hydrocarbyl group carrying at least one aryl substituent, e.g. an alkenylaryl group or an alkylaryl group, where preferably less than 15%, more preferably less than 10% and even more preferably less than 5%, e.g. less than 3% or less than 2%, of the carbon atoms of the aliphatic moiety are quaternary.
• C 8 -C 40 -Alkenyl is a singly unsaturated straight-chain or branched aliphatic hydrocarbon radical having from 8 to 40 carbon atoms.
• Examples include octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl, eicosenyl, hencosenyl, docosenyl, tricosenyl, tetracosenyl, pentacosenyl, hexacosenyl, heptacosenyl, octacosenyl, nonacosenyl, squalenyl, constitutional isomers thereof, the higher homologs and their constitutional
• constitutional isomers of the aforementioned alkenyl radicals are polyalkenyl radicals derived from oligomers and polymers of ⁇ -, ⁇ -, ⁇ -, ⁇ -, etc.
• C 3 -C 8- olefins such as propene, 1- or 2-butene, 1- or 2-pentene, 1-, 2- or 3-hexene, 1-, 2- or 3-heptene or 1-, 2-, 3- or 4-octene.
• C 4 -C 40 -Alkenyl is a singly unsaturated straight-chain or branched aliphatic hydrocarbon radical having from 4 to 40 carbon atoms. Examples include the above-listed examples for C 8 -C 40 -alkenyl and further butenyl, pentenyl, hexenyl and heptenyl and constitutional isomers thereof.
• C 8 -C 80 -Alkenyl is a singly unsaturated straight-chain or branched aliphatic hydrocarbon radical having from 8 to 80 carbon atoms. Examples include the aforementioned C 8- C 40 -alkenyl radicals, constitutional isomers thereof, the higher homologs and their constitutional isomers.
• C 4 -C 80 -Alkenyl is a singly unsaturated straight-chain or branched aliphatic hydrocarbon radical having from 4 to 80 carbon atoms.
• Examples include the aforementioned C 8- C 80 -alkenyl radicals and further butenyl, pentenyl, hexenyl and heptenyl and constitutional isomers thereof.
• C 10 -C 30 -Alkenyl is a singly unsaturated straight-chain or branched aliphatic hydrocarbon radical having from 10 to 30 carbon atoms.
• Examples include decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl, eicosenyl, hencosenyl, docosenyl, tricosenyl, tetracosenyl, pentacosenyl, hexacosenyl, heptacosenyl, octacosenyl, nonacosenyl, squalenyl, constitutional isomers thereof, the higher homologs and their constitutional isomers.
• C 8 -C 40 -Alkyl is a straight-chain or branched alkyl group having from 8 to 40 carbon atoms.
• Examples include octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, hencosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, squalyl, constitutional isomers thereof, the higher homologs and their constitutional isomers.
• C 4 -C 40 -Alkyl is a straight-chain or branched alkyl group having from 4 to 40 carbon atoms. Examples include the aforementioned C 8 -C 40 -alkyl radicals and further butyl, pentyl, hexyl and heptyl and constitutional isomers thereof.
• C 8 -C 80 -Alkyl is a straight-chain or branched hydrocarbon radical having from 8 to 80 carbon atoms. Examples include the aforementioned C 8 -C 40 -alkyl radicals, constitutional isomers thereof, the higher homologs and their constitutional isomers.
• C 4 -C 80 -Alkyl is a straight-chain or branched hydrocarbon radical having from 4 to 80 carbon atoms.
• Examples include the aforementioned C 8 -C 80 -alkyl radicals and further butyl, pentyl, hexyl and heptyl and constitutional isomers thereof.
• C 10 -C 30 -Alkyl is a straight-chain or branched hydrocarbon radical having from 10 to 30 carbon atoms.
• Examples include decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, hencosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, squalyl, constitutional isomers thereof, the higher homologs and their constitutional isomers.
• C 1 -C 4 -Alkyl is a straight-chain or branched alkyl group having from 1 to 4 carbon atoms. Examples of an alkyl group are methyl, ethyl, n-propyl, iso-propyl, n-butyl, 2-butyl, iso-butyl or tert -butyl.
• C 1 -C 2 Alkyl is methyl or ethyl
• C 1 -C 3 alkyl is additionally n-propyl or isopropyl.
• C 1 -C 8 -Alkyl is a straight-chain or branched alkyl group having from 1 to 8 carbon atoms.
• Examples include C 1 -C 4 alkyl as mentioned above and also pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl,
• C 1 -C 10 -Alkyl is a straight-chain or branched alkyl group having from 1 to 10 carbon atoms. Examples include C 1 -C 8 -alkyl as mentioned above and also nonyl, decyl, and constitutional isomers thereof.
• C 1 -C 20 -Alkyl is a straight-chain or branched alkyl group having from 1 to 20 carbon atoms.
• Examples include C 1 -C 8 -alkyl as mentioned above and also nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl and eicosyl and constitutional isomers thereof.
• C 2 -C 8 -Hydroxyalkyl is a straight-chain or branched alkyl group having from 2 to 8 carbon atoms, in particular 2 to 4 carbon atoms, wherein at least one, e.g. 1, 2, 3, or 4 of the hydrogen atoms are replaced by a hydroxy group such as in 2-hydroxy-1-ethyl, 2-and 3-hydroxypropyl, 2-,3- and 4-hydroxy-1-butyl, 2-,3-, 4- and 5-hydroxy-1-pentyl, 2-,3-, 4-, 5- and 6-hydroxy-1-hexyl, 2-,3-, 4-, 5-, 6- and 7-hydroxy-1-heptyl, 2-,3-, 4-, 5-, 6-,7- and 8-hydroxy-1-octyl, 2,3-dihydroxy-1-propyl and the like.
• C 2 -C 8 -Alkylene is a linear or branched hydrocarbon bridging group having 2, 3, 4, 5, 6, 7 or 8 carbon atoms, like 1,2- ethylene, 1,2- and 1,3-propylene, 1,2-, 1,3-, 2,3- and 1,4-butylene, 2,2-dimethyl-1,2-ethylene, 1,1-dimethyl-1,2-ethylene, 1,5-pentylene, 1,6-hexylene, 1,7-heptylene, 1,8-octylene and constitutional isomers thereof.
• C 2 -C 4- Alkylene is a linear or branched hydrocarbon bridging group having 2, 3 or 4 carbon atoms, like 1,2- ethylene, 1,2- and 1,3-propylene, 1,2-, 1,3-, 2,3- and 1,4-butylene, 2,2-dimethyl-1,2-ethylene, 1,1-dimethyl-1,2-ethylene and the like.
• C 1 -C 8 -Alkoxy is a straight-chain or branched alkyl group having from 1 to 8, in particular 1 to 4 carbon atoms, which is bound to the remainder of the molecule via an oxygen atom.
• Examples include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, 2-butoxy; iso-butoxy, tert.-butoxy pentyloxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexyloxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 1-methylpentyloxy, 2-methylpentyloxy, 3-methylpentyloxy, 4-methylpentyloxy, 1,1-dimethylbutyloxy, 1,2-dimethylbutyloxy, 1,3-dimethylbutyloxy, 2,2-dimethylbutyloxy, 2,3-dimethylbutyloxy, 3,3-d
• Aryl denotes a carbocyclic C 6 -C 14 -aromatic radical like phenyl, naphthyl, anthracenyl or phenantrenyl, which optionally carries 1 to 3 substituents selected from halogen, OH, C 1 -C 8 -alkoxy, C 1 -C 8 -alkyl, nitro, cyano and an aryl radical.
• Alkylaryl is an alkyl group which carries at least one aryl radical and is in particular a C 1 -C 20 -alkylaryl group.
• C 1 -C 20 -alkylaryl denotes a C 1 -C 20 -alkyl group which carries at least one aryl radical.
• Examples thereof are benzyl, 1- and 2-phenylethyl, 1-, 2- and 3-phenylpropyl, 1-, 2-, 3- and 4-phenylbutyl, 1-, 2-, 3-, 4- and 5-phenylpentyl, 1-, 2-, 3-, 4-, 5- and 6-phenylhexyl, 1-, 2-, 3-, 4-, 5-, 6- and 7-phenylheptyl, 1-, 2-, 3-, 4-, 5-, 6-, 7-and 8-phenyloctyl, 1-, 2-, 3-, 4-, 5-, 6-, 7-, 8- and 9-phenylnonyl, 1-, 2-, 3-, 4-, 5-, 6-, 7-, 8-, 9- and 10-phenyldecyl, 1-, 2-, 3-, 4-, 5-, 6-, 7-, 8-, 9-, 10 and 11-phenylundecyl, phenyldodecyl, phenyltridecyl, phenyltetradecyl, phenyl
• C 1 -C 10 -alkylarylde notes a C 1 -C 10 -alkyl group which carries at least one aryl radical.
• Examples thereof are benzyl, 1- and 2-phenylethyl, 1-, 2- and 3-phenylpropyl, 1-, 2-, 3-and 4-phenylbutyl, 1-, 2-, 3-, 4- and 5-phenylpentyl, 1-, 2-, 3-, 4-, 5- and 6-phenylhexyl, 1-, 2-, 3-, 4-, 5-, 6- and 7-phenylheptyl, 1-, 2-, 3-, 4-, 5-, 6-, 7- and 8-phenyloctyl, 1-, 2-, 3-, 4-, 5-, 6-, 7-, 8- and 9-phenylnonyl, and 1-, 2-, 3-, 4-, 5-, 6-, 7-, 8-, 9- and 10-phenyldecyl, and constitutional isomers thereof.
• Alkenylaryl is an alkenyl group which carries at least one aryl radical and is in particular a C 1 -C 20 -alkenylaryl group.
• C 1 -C 20 -alkenylaryl denotes a C 1 -C 20 -alkenyl group which carries at least one aryl radical.
• the metal equivalent (M x+ ) 1/x is a metal cation carrying 1, 2, 3 or 4 positive charges and respectively formally equivalating 1, 2, 3 or 4 anions O - (or, more precisely, COO - ), or (M x+ ) 1/x is an ammonium cation NH 4 + which formally equivalates 1 anion O - (or, more precisely, COO - ) or (M x+ ) 1/x is a substituted ammonium cation and respectively formally equivalating 1 to 10 anions O - (or, more precisely, COO - ).
• substituted ammonium cation denotes a cation derived from a monoamine NR 10 R 11 R 12 , where the radicals R 10 , R 11 and R 12 are, independently of each other, selected from hydrogen, aliphatic hydrocarbyl which is optionally substituted by hydroxyl groups, araliphatic hydrocarbyl and aryl, with the proviso that at least one of the radicals R 10 , R 11 and R 12 is not hydrogen, or from a diamine or a polyamine, where the amino function(s) may be substituted by aliphatic hydrocarbyl groups which are optionally substituted by hydroxyl groups; araliphatic hydrocarbyl groups and/or aryl groups.
• the cation generally results from the addition of protons H + to at least part of the basic nitrogen atoms present in the amine.
• halogen denotes in each case fluorine, bromine, chlorine or iodine, in particular fluorine, chlorine or bromine.
• R 1 is a linear or branched aliphatic hydrocarbyl group containing 4 to 80, e.g. 8 to 80, preferably 4 to 40, more preferably 8 to 40 and in particular 10 to 30 carbon atoms.
• Preferred aliphatic hydrocarbyl groups are alkyl, e.g. C 4 -C 80 -alkyl, such as C 8 -C 80 -alkyl, preferably C 4 -C 40 -alkyl, more preferably C 8 -C 40 -alkyl, in particular C 10 -C 30- alkyl, and alkenyl, e.g.
• C 4 -C 80 -alkenyl such as C 8 -C 80 -alkenyl, preferably C 4 -C 40- alkenyl, more preferably C 8 -C 40 -alkenyl, in particular C 10 C 30 -alkenyl.
• R 1 is preferably a C 1 -C 20 -alkylaryl group, more preferably a C 1 -C 10- alkylaryl group. Suitable alkylaryl groups are listed above.
• R 1 is a linear or branched aliphatic hydrocarbyl group, such as an alkyl group or an alkenyl group, as defined above.
• R 1 is a linear or branched alkenyl group, preferably a C 4 -C 80 -alkenyl group, such as a C 8 -C 80 -alkenyl group, more preferably a C 4- C 40 -alkenyl group, especially a C 8 -C 40 -alkenyl group and in particular a C 10 -C 30 -alkenyl group.
• R 1 is derived from an alkene, preferably from a C 4 -C 80 -alkene, e.g. a C 8 -C 80 -alkene, more preferably from a C 4 -C 40 -alkene, e.g. a C 8- C 40 -alkene, and in particular from a C 10 -C 30 -alkene.
• the alkene may be linear or branched (with the above proviso), and the olefinic double bond may be in a terminal or internal position.
• Preferred alkenes are ⁇ -alkenes (i.e. the olefinic double bond is in a terminal position), e.g.
• ⁇ -C 4 -C 80 -alkenes such as ⁇ -C 8 -C 80 -alkenes, preferably ⁇ -C 4- C 40 -alkenes, e.g. ⁇ -C 8 -C 40 -alkenes, and more preferably ⁇ -C 10 -C 30 -alkenes.
• the alkenes are linear ⁇ -alkenes.
• R 1 is derived from a polyalkene, which is obtained by oligo- or polymerization of an alkene.
• the polyalkene is a C 4 -C 80 -polyalkene, e.g. a C 8 -C 80- polyalkene, more preferably a C 4 -C 40 -polyalkene, e.g. a C 8 -C 40 -polyalkene, and in particular a C 10 -C 30 -polyalkene.
• the alkene from which the polyalkene is derived may be linear or branched.
• the alkene is selected from C 2 -C 8 -alkenes, such as ethylene, propene, 1- or 2-butene, 1- or 2-pentene, 1-, 2- or 3-hexene, 1-, 2- or 3-heptene and 1-, 2-, 3- or 4-octene or constitutional or stereochemical isomers thereof.
• the polyalkene may also be obtained from oligo- or polymerzation of an alkene mixture, especially of a technical mixture of olefins such as obtained in industrial processes, e.g.
• alkenes contained in the mixture are alkenes wherein one or both carbon atoms of the olefinic double bond carry two substituents different from hydrogen.
• a suitable technical mixture is e.g. a C 4 -cut comprising 1-butene, 2-butene and isobutene, wherein isobutene is contained in an amount of not more than 20% by weight, preferably not more than 10% by weight, more preferably not more than 5 % by weight, based on the total weight of the composition.
• R 1 is derived from dodecene, tridecene, tetradecene, pentadecene, hexadecene, heptadecene, octadecene, nonadecene, eicosene, or the higher homologs.
• the olefinic double bond in said alkenes is in the ⁇ -position and/or the alkenes are linear.
• R 1 is derived from the tri-, tetra- or pentamers of butene, hexene or octene.
• the compound of formula (I) is a mixture of compounds of formula (I) with different radicals R 1 , where the mixture contains not more than 10% by weight, preferably not more than 5% by weight, more preferably not more than 3% by weight of compounds of formula (I) wherein R 1 is a C 4 -C 7 -hydrocarbyl group, e.g. a C 4 -C 7 -alkyl group or a C 4 -C 7 -alkenyl group.
• R 2 , R 3 and R 4 are, independently of each other, hydrogen, C 1 -C 8 -alkyl, C 2 -C 8 -hydroxyalkyl, C 2 -C 8 -alkylene-NR 6 R 7 , a group of the formula ⁇ A-NR 8 ⁇ y A-NR 6 R 7 , a group of the formula ⁇ A-O ⁇ y A-O-R 9 , or are aryl or alkylary.
• R 2 , R 3 and R 4 are, independently of each other, hydrogen, C 1 -C 8 -alkyl, C 2 -C 8- hydroxyalkyl, C 2 -C 8 -alkylene-NR 6 R 7 , a group of the formula ⁇ A-NR 8 ⁇ y A-NR 6 R 7 or a group of the formula ⁇ A-O ⁇ y A-O-R 9 .
• R 2 is hydrogen, C 1 -C 8 -alkyl, e.g. C 1 -C 4 -alkyl, C 2 -C 8 -hydroxyalkyl, e.g.
• R 3 and R 4 are more preferably, independently of each other, hydrogen, C 1 -C 8 -alkyl, e.g. C 1 -C 4 -alkyl, C 2 -C 8 -hydroxyalkyl, e.g. C 2 -C 4- hydroxyalkyl, C 2 -C 8 -alkylene-NR 6 R 7 , e.g. C 2 -C 4 -alkylene-NR 6 R 7 , or a group of the formula ⁇ A-NR 8 ⁇ y A-NR 6 R 7 .
• R 8 is hydrogen or C 1 -C 8 -alkyl.
• R 8 is hydrogen or C 1 -C 4 -alkyl, especially hydrogen, methyl or ethyl and in particular hydrogen.
• R 6 and R 7 are, independently of each other, hydrogen, C 1- C 4 -alkyl or C 1 -C 4 -hydroxyalkyl. In a more preferred embodiment, R 6 and R 7 are, independently of each other, hydrogen or C 1 -C 4 -alkyl, especially hydrogen, methyl or ethyl and in particular hydrogen.
• R 9 is hydrogen or C 1 -C 4 -alkyl. More preferably, R 9 is hydrogen or methyl and in particular hydrogen.
• A is preferably 1,2-ethylene (-(CH 2 ) 2 -), 1,2-propylene (-CH 2 -CH(CH 3 )- or -CH(CH 3 )-CH 2 -), 1,3-propylene (-(CH 2 ) 3 -) or 1,4-butylene (-(CH 2 ) 4 -).
• A is 1,2-ethylene.
• y is preferably 0,1, 2, 3, 4 or 5, more preferably 1, 2, 3 or 4.
• R 2 is hydrogen or C 1 -C 4 -alkyl. Especially, R 2 is hydrogen.
• R 3 and R 4 are hydrogen or C 1 -C 4 -alkyl. Especially, R 3 and R 4 are hydrogen.
• X and Y are, independently of each other, OR 2 , O-(M x+ ) 1/x , NR 3 R 4 or X and Y together form a group -O- or -(NR 5 )-, where R 2 , R 3 and R 4 are, independently of each other, hydrogen, C 1 -C 8 -alkyl, C 2 -C 8 -hydroxyalkyl, C 2 -C 8- alkylene-NR 6 R 7 , a group of the formula ⁇ A-NR 8 ⁇ y A-NR 6 R 7 or a group of the formula ⁇ A-O ⁇ y A-O-R 9 .
• R 2 is hydrogen, C 1 -C 8 -alkyl, e.g. C 1 -C 4 -alkyl, C 2 -C 8- hydroxyalkyl, e.g. C 2 -C 4 -hydroxyalkyl, or a group of the formula ⁇ A-O ⁇ y A-O-R 9 . in particular hydrogen or C 1 -C 4 -alkyl and especially hydrogen. More preferably, R 3 and R 4 are, independently of each other, hydrogen, C 1 -C 8 -alkyl, e.g. C 1 -C 4 -alkyl, C 2 -C 8- hydroxyalkyl, e.g.
• C 2 -C 4 -hydroxyalkyl C 2 -C 8 -alkylene-NR 6 R 7 , e.g. C 2 -C 4 -alkylene-NR 6 R 7 , or a group of the formula ⁇ A-NR 8 ⁇ y A-NR 6 R 7 , in particular hydrogen or C 1 -C 4- alkyl and especially hydrogen.
• R 6 , R 7 , R 8 , R 9 , A and y and their preferred embodiments are as defined above.
• (M x+ ) 1/x is an alkali metal equivalent, an alkaline earth metal equivalent, an ammonium cation NH 4 + or a substituted ammonium cation.
• x is 1 if M is an alkali metal or an ammonium cation NH 4 + and x is 2 if M is an alkaline earth metal.
• Preferred alkali metals are lithium, sodium and potassium and consequently, preferred alkali metal equivalents are Li + , Na + and K + .
• Preferred alkaline earth metals are magnesium and calcium and consequently, preferred alkaline earth metal equivalents are 1 ⁇ 2 Mg 2+ and 1 ⁇ 2 Ca 2+ .
• (M x+ ) 1/x is a substituted ammonium cation, this is preferably derived from a monoamine NR 10 R 11 R 12 , from a diamine of the formula NR 10 R 11 -C 2 -C 8 -alkylene-NR 6 R 7 or from a polyamine of the formula NR 10 R 11 ⁇ A-NR 8 ⁇ w A-NR 6 R 7 1 where
• Suitable and preferred amines from which the cations are derived are listed below.
• the ammonium cation derived from the above amines generally results from the addition of a cation, preferably of a proton H + to at least part of the basic nitrogen atoms present in the amine. Consequently, the ammonium cation derived from the monoamine preferably has the formula [NHR 10 R 11 R 12 ] + ; preferably, the ammonium cation derived from the diamine is either a monocation of the formula [NHR 10 R 11 -C 2 -C 8 -alkylene-NR 6 R 7 ] + or [NR 10 R 11 -C 2 C 8 -alkylene-NHR 6 R 7 ] + or a dication of the formula [NHR 10 R 11- C 2 -C 8 -alkylene-NHR 6 R 7 ] 2+ ; and preferably, the ammonium cation derived from the polyamine is either a monocation or a polycation having from 2 to (w+2) positive charges, depending from the number of protonated nitrogen
• Preferred radicals R 10 , R 11 and R 12 are hydrogen, C 1 -C 4 -alkyl or C 2 -C 4 -hydroxyalkyl, more preferred being hydrogen and C 1 -C 4 -alkyl.
• at least 2 of the radicals R 10 , R 11 , R 6 and R 7 are hydrogen. More preferably, at least one of the radicals R 10 and R 11 and least one of the radicals R 6 and R 7 is hydrogen.
• all four radicals R 6 , R 7 , R 10 and R 11 are hydrogen.
• R 8 is also hydrogen.
• the compound of formula (I) is a hydrocarbyl-substituted succinic acid anhydride. If X and Y together form a group -(NR 5 )-, the compound of formula (I) is a hydrocarbyl-substituted succinic imide. If R 5 is a group of formula (II), the compound of formula (I) is a diimide.
• R 5 is hydrogen, C 1 -C 8 -alkyl, e.g. C 1 -C 4 -alkyl, C 2 -C 8 -hydroxyalkyl, e.g. C 2 -C 4- hydroxyalkyl, C 2 -C 8 -alkylene-NR 6 R 7 , e.g. C 2 -C 4 -alkylene-NR 6 R 7 , or a group of the formula ⁇ A-NR 8 ⁇ y A-NR 6 R 7 , wherein R 6 , R 7 , R 8 , A and y and their preferred embodiments are as defined above.
• R 5 is a group of formula (II), wherein B preferably is C 2 -C 8 -alkylene or a group of the formula ⁇ A-NR 8 ⁇ y A-, wherein A and y and their preferred embodiments are as defined above.
• X and Y are, independently of each other, OH or O - (M x+ ) 1/x , or X and Y together form a group -O-.
• (M x+ ) 1/x is an alkali or alkaline earth metal cation or more preferably an ammonium cation NH 4 + or a substituted ammonium cation as defined above.
• (M x+ ) 1/x is an ammonium cation derived from substituted amines and in particular from diamines or polyamines. Examples of suitable substituted amines are listed below.
• the compound of formula (I) is a hydrocarbyl succinic acid of the formula (I-1) which is at least partially neutralized by a monoamine NR 10 R 11 R 12 or a diamine NR 10 R 11 -C 2 -C 8 -alkylene-NR 6 R 7 or a polyamine of the formula NR 10 R 11 ⁇ A-NR 8 ⁇ w A-NR 6 R 7 , where
• the radicals R 10 , R 11 and R 12 are, independently of each other, preferably hydrogen, C 1 -C 4 -alkyl, or C 2 -C 4 -hydroxyalkyl, and in particular hydrogen or C 1 -C 4 -alkyl.
• R 6 , R 7 , R 10 and R 11 are, independently of each other, preferably hydrogen, C 1 -C 4 -alkyl, or C 2 -C 4 -hydroxyalkyl. More preferably, R 6 , R 7 , R 10 and R 11 are, independently of each other, hydrogen or C 1 -C 4 -alkyl. In an even more preferred embodiment, at least two of the radicals R 10 , R 11 , R 6 and R 7 are hydrogen. More preferably, at least one of the radicals R 10 and R 11 and least one of the radicals R 6 and R 7 is hydrogen. In particular, all four radicals R 6 , R 7 , R 10 and R 11 are hydrogen. Especially, R 8 is also hydrogen.
• Useful amines NR 11 R 12 R 13 are ammonia and primary, secondary or tertiary monoamines, such as methylamine, dimethylamine, trimethylamine, ethylamine, diethylamine, triethylamine, ethanolamine, diethanolamine, triethanolamine, propylamine, dipropylamine, tripropylamine, propanolamine, dipropanolamine, tripropanolamine, isopropylamine, diisopropylamine, triisopropylamine, ethyldiisopropylamine, butylamine, dibutylamine, tributylamine, isobutylamine, diisobutylamine, tert-butylamine, di-tert-butylamine, pentylamine, hexylamine and the
• Examples for diamines of the formula NR 10 R 11 -C 2 -C 8 -alkylene-NR 6 R 7 and for polyamines of the formula NR 10 R 11 ⁇ A-NR 8 ⁇ w A-NR 6 R 7 are ethylenediamine, diethylentriamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, propylenediamine, dipropylentriamin, tripropylenetetramine, tetrapropylenepentamine, pentapropylenehexamine, butylenediamine, dibutylenetriamine, tributylenetetramine, tetrabutylenepentamine, pentabutylenehexamine, pentylenediamine, hexylenediamine, heptylenediamine, octylenediamine, N,N-dimethylethylene-1,2-diamine, N,N'-dimethylethylene-1,2-d
• the acid halide can then be converted into the mono- or diester by reacting with the corresponding amount of an alcohol R 2 OH.
• the acid salts can be prepared e.g. by hydrolyzing the anhydride with a metal hydroxide or by reacting the acid with an amine.
• the fuel is additized with the compound of formula (I) in an amount of from 10 to 300, more preferably from 20 to 200, in particular from 25 to 150 mg per kg of the fuel.
• the compound of formula (I) is used in the fuel in combination with at least one further conventional fuel additive.
• Conventional fuel addtives are, e.g., detergent additives, carrier oils, corrosion inhibitors, antioxidants, antistatics, markers, etc., and mixtures thereof.
• Additives having a detergent action or an anti-valve seat recession action are e.g. compounds which contain at least one hydrophobic hydrocarbon group having a number-average molecular weight (M n ) of from 85 to 20,000 and at least one polar group selected from
• the hydrophobic hydrocarbon group in the additives which provides sufficient solubility in the fuel, has a number-average molecular weight (M n ) of from 85 to 20,000, preferably from 113 to 10,000 and more preferably from 300 to 5000.
• Typical hydrophobic hydrocarbon groups, particularly in conjunction with the polar groups (a), (c), (h) and (i), are polypropenyl, polybutenyl and polyisobutenyl radicals having molecular weights M n of from 300 to 5000, preferably from 500 to 2500 and more preferably from 750 to 2250.
• Additives containing monoamino or polyamino groups are preferably polyalkene monoamines or polyalkene polyamines based on polypropylene or highly reactive (ie containing predominantly terminal double bonds - mostly in the ⁇ -and ⁇ -positions) or conventional ( ie containing predominantly centered double bonds) polybutylene or polyisobutylene having a molecular weight M n of from 300 to 5000.
• Such additives based on highly reactive polyisobutylene which can be prepared from the polyisobutylene containing up to 20 wt% of n-butylene units, by hydroformylation and reductive amination with ammonia, monoamines or polyamines such as dimethylaminopropylamine, ethylenediamine, diethylenetriamine, triethylenetetramine or tetrethylenepentamine, are disclosed, in particular, in EP-A 244,616.
• the synthesis of the additives is based on polybutylene or polyisobutylene having predominantly centered double bonds (mostly in the ⁇ and ⁇ positions) as starting materials, an obvious choice is the synthesis method involving chlorination and subsequent amination, or oxidation of the double bond with air or ozone to form the carbonyl or carboxyl compound, with subsequent amination under reductive (hydrogenating) conditions.
• This amination may be carried out using the same amines as mentioned above for the reductive amination of hydroformylated, highly reactive polyisobutylene.
• Corresponding additives based on polypropylene are described, in particular, in WO-A 94/24231.
• additives containing monoamino groups (a) are the hydrogenation products of the reaction products of polyisobutylenes having an average degree of polymerization P of from 5 to 100 with nitrogen oxides or mixtures of nitrogen oxides and oxygen, as described, in particular, in WO-A 97/03946.
• additives containing monoamino groups (a) are the compounds produced from polyisobutylene epoxides by reaction with amines followed by dehydration and reduction of the amino alcohols, as described, in particular, in DE-A 196 20 262.
• Additives containing nitro groups, optionally combined with hydroxyl groups (b), are preferably reaction products of polyisobutylenes having an average degree of polymerization P of from 5 to 100 or from 10 to 100 with nitrogen oxides or mixtures of nitrogen oxides and oxygen, as described, in particular, in WO-A 96/03367 and WO-A 96/03479. These reaction products are usually mixtures of pure nitropolyisobutanes (eg ⁇ , ⁇ -dinitropolyisobutane) and mixed hydroxynitropolyisobutanes ( eg ⁇ -nitro- ⁇ -hydroxypolyisobutane).
• Additives containing hydroxyl groups combined with monoamino or polyamino groups (c) are in particular reaction products of polyisobutylene epoxides, obtainable from polyisobutylene preferably containing predominantly terminal double bonds and having a molecular weight M n of from 300 to 5000, with ammonia or mono- or polyamines, as described, in particular, in EP-A 476,485.
• Additives containing carboxylic acid groups or the alkali metal or alkaline earth metal salts thereof (d) are preferably copolymers of C 2 -C 40 olefins with maleic anhydride having a total molecular weight of from 500 to 20,000 whose carboxylic acid groups have been converted entirely or partially to the alkali metal or alkaline earth metal salts and the remainder of the carboxylic acid groups has been caused to react with alcohols or amines.
• Such additives are disclosed, in particular, in EP-A 307,815. Said additives mainly serve to prevent valve seat recession and can be used, as described in WO-A 87/01126, with advantage combined with conventional fuel detergents such as poly(iso)butylene amines or polyether amines.
• Additives containing sulfo groups or the alkali metal or alkaline earth metal salts thereof are preferably alkali metal or alkaline earth metal salts of an alkyl sulfosuccinate, as described, in particular, in EP-A 639,632.
• Such additives mainly serve to prevent valve seat recession and can be used with advantage combined with conventional fuel detergents such as poly(iso)butylene amines or polyether amines.
• Additives containing polyoxy-(C 2 -C 4 alkylene) groups (f) are preferably polyethers or polyether amines, which are obtained by reaction of C 2 -C 60 alkanols, C 6 -C 30 alkanediols, mono- or di-(C 2 -C 30 alkyl)amines, (C 1 -C 30 alkyl)cyclohexanols or (C 1 -C 30 alkyl)phenols with from 1 to 30 mol of ethylene oxide and/or propylene oxide and/or butylene oxide per hydroxyl group or amino group and, in the case of polyether amines, by subsequent reductive amination with ammonia, monoamines or polyamines.
• Such products are described, in particular, in EP-A 310,875, EP-A 356,725, EP-A 700,985 and US-A 4,877,416.
• polyethers such products also have flotation oil characteristics.
• Typical examples thereof are tridecanol butoxylates or isotridecanol butoxylates, isononylphenol butoxylates, polyisobutenol butoxylates and polyisobutenol propoxylates and the corresponding reaction products with ammonia.
• Additives containing carboxylate groups (g) are preferably esters of mono-, di- or tri-carboxylic acids with long-chain alkanols or polyols, in particular those having a minimum viscosity of 2 mm 2 /s at 100°C, as described, in particular, in DE-A 3,838,918.
• the mono-, di- or tri-carboxylic acids used can be aliphatic or aromatic acids, and suitable ester alcohols or ester polyols are primarily long-chain representatives containing, for example, from 6 to 24 carbon atoms.
• Typical representatives of these esters are adipates, phthalates, isophthalates, terephthalates and trimellitates of isooctanol, isononanol, isodecanol and isotridecanol. Such products also have flotation oil characteristics.
• Additives containing groups derived from succinic anhydride and containing hydroxyl and/or amino and/or amido and/or imido groups (h) are preferably corresponding derivatives of polyisobutenyl succinic anhydride, which are obtained by reaction of conventional or highly reactive polyisobutylene having a molecular weight M n of from 300 to 5000 with maleic anhydride by thermal treatment or via chlorinated polyisobutylene.
• derivatives with aliphatic polyamines such as ethylenediamine, diethylenetriamine, triethylenetetramine or tetrethylenepentamine.
• Such fuel additives are described, in particular, in US-A 4,849,572.
• Additives containing groups (i) produced by Mannich reaction of substituted phenols with aldehydes and mono- or poly-amines are preferably reaction products of polyisobutylene-substituted phenols with formaldehyde and mono- or poly-amines such as ethylenediamine, diethylenetriamine, triethylenetetramine, tetrethylenepentamine or dimethylaminopropylamine.
• the polyisobutenyl-substituted phenols can be derived from conventional or highly reactive polyisobutylene having a molecular weight M n of from 300 to 5000.
• Such "polyisobutylene Mannich bases” are described, in particular, in EP-A 831,141.
• Examples of conventional carrier oils are, for example, mineral carrier oils (base oils) and synthetic carrier oils.
• suitable mineral carrier oils are in particular those of viscosity class Solvent Neutral (SN) 500 to 2000, as well as aromatic and paraffinic hydrocarbons and alkoxyalkanols.
• synthetic carrier oils are used.
• Preferred synthetic carrier oils are alkanol alkoxylates, in particular alkanol propoxylates and alkanol butoxylates.
• corrosion inhibitors for example based on ammonium salts of organic carboxylic acids, which salts tend to form films, or on heterocyclic aromatics in the case of corrosion protection of nonferrous metals, antioxidants or stabilizers, for example based on amines, such as p-phenylenediamine, dicyclohexylamine or derivatives thereof and on phenols, such as 2,4-di-tertbutylphenol or 3,5-di-tert-butyl-4-hydroxyphenylpropionic acid, dehazers, demulsifiers, antistatic agents, metallocenes such as ferrocene or methylcyclopentadienyl manganese tricarbonyl, lubricity additives (different from compound (I)), such as certain fatty acids, alkenylsuccinic esters, bis(hydroxyalkyl)fatty amines, hydroxyacetamides and castor oil, antiknock additives, anti-icing additives, oc
• the invention is further related to a fuel composition containing a fuel as major component and at least one compound of the formula (I) as defined above and optionally at least one further additive. Suitable additives are those listed above.
• Suitable fuels are middle distillates and gasolines.
• Suitable middle distillates are for example diesel fuel, kerosene and heating oil.
• preference is given to the use of compounds of formula (I) as friction modifiers for gasolines.
• gasoline includes blends of distillate hydrocarbon fuels with oxygenated compounds such as ethanol, as well as the distillate fuels themselves.
• Suitable gasolines are e.g. those described in Ullmann's Encyclopedia of Industrial Chemistry, 5 th edition, 1990, volume A16, page 719 ff.
• Suitable gasolines are e.g. those having an aromatics content of not more than 60% by volume, e.g. not more than 42% by volume or not more than 35% by volume and/or a sulfur content of not more than 2000 ppm by weight, e.g. not more than 150 ppm by weight or not more than 10 ppm by weight.
• the aromatics content of the gasoline is e.g. from 10 to 50% by volume, e.g. from 30 to 42% by volume, in particular from 32 to 40% by volume or not more than 35% by volume.
• the sulfur content is e.g. of from 2 to 500 ppm by weight, e.g. of from 5 to 100 or not more than 10 ppm by weight.
• the olefin content of the gasoline can be up to 50% by volume, e.g. from 6 to 21% by volume, in particular from 7 to 18% by volume.
• the gasoline has a benzene content of not more than 5% by volume, e.g. from 0.5 to 1.0% by volume, in particular from 0.6 to 0.9% by volume.
• the gasoline has an oxygen content of not more than 25% by weight, e.g. up to 10% by weight or from 1.0 to 2.7% by weight, and in particular from 1.2 to 2.0% by weight.
• a gasoline which has an aromatics content of not more than 38% by volume or preferably not more than 35% by volume, and at the same time an olefin content of not more than 21% by volume, a sulfur content of not more than 50 or 10 ppm by weight, a benzene content of not more than 1.0% by volume and an oxygen content of from 1.0 to 2.7% by weight.
• the amount of alcohols and ethers contained in the gasoline may vary over wide ranges. Typical maximum contents are e.g. methanol 15% by volume, ethanol 65% by volume, isopropanol 20% by volume, tert-butanol 15% by volume, isobutanol 20% by volume and ethers containing 5 or more carbon atoms in the molecule 30% by volume.
• the summer vapor pressure of the gasoline (at 37°C) is usually not more than 70kPa, in particular not more than 60kPa.
• the research octane number (RON) of the gasoline is usually from 75 to 105.
• a usual range for the corresponding motor octane number (MON) is from 65 to 95.
• the invention is related to an additive concentrate, comprising at least one compound of the formula (I) as defined above and at least one diluent and optionally at least one further additive.
• Suitable additional additives are those mentioned above.
• Suitable diluents are e.g. aromatic and aliphatic hydrocarbons, such as benzene, toluene, the xylenes, solvent naphtha, and alkanols with 3 to 8 carbon atoms, e.g. propanol, isopropanol, n-butanol, sec-butanol, isobutanol and the like, in combination with hydrocarbon solvents, and alkoxyalkanols.
• aromatic and aliphatic hydrocarbons such as benzene, toluene, the xylenes, solvent naphtha, and alkanols with 3 to 8 carbon atoms, e.g. propanol, isopropanol, n-butanol, sec-butanol, isobutanol and the like, in combination with hydrocarbon solvents, and alkoxyalkanols.
• the compound(s) of formula (I) are preferably present in the concentrates in an amount of from 0.1 to 80% by weight, more preferably from 1 to 70% by weight and in particular from 5 to 60% by weight, based on the total weight of the concentrate.
• the invention is related to a method for producing a fuel composition with improved friction properties, where a fuel or a commercial fuel composition is additized with at least one compound of the formula (I) as defined above or with the additive concentrate as defined above.
• the compound(s) of formula (I) and optionally said additional additives are metered into the fuel or fuel composition, where they become effective.
• the compounds (I) and optionally the additional additives can be added to the fuel or to the fuel composition individually or as a previously prepared concentrate (additive package).
• the compounds of formula (I) exhibit, in addition to their good friction modifying characteristics, a good compatibility with other additives and solvents in the concentrates and a good solubility in the fuel. Moreover, they do not adversely affect the properties of other additives present in the fuel or in the concentrate. Furthermore, they exhibit an additional corrosion protection for metals, especially for aluminium, magnesium, tin, lead, copper, iron, zinc, chromium, manganese and silver, and for alloys containing at least one of these metals.
• the gasolines Prior to testing, the gasolines (gasolines according to EN 228) were gently concentrated to 50 vol.-% using the distillation apparatus MP 628 from Herzog, Lauda-Königshofen, Germany.
• the lubricity of the unadditized concentrated gasoline was tested according to the above-described HFFR-test and compared with the lubricity observed when the concentrated gasoline was additized as shown in table 1.
• the resulting wear scar diameters are also listed in table 1. The lower the value of the wear scar diameter, the better the performance of the additive in the fuel composition.

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• 2004
  • 2004-12-13 EP EP04029480A patent/EP1669433A1/fr not_active Withdrawn
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