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
  • 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
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/22—Organic compounds containing nitrogen
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/22—Organic compounds containing nitrogen
  • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
  • C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
  • C10L1/2225—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates hydroxy containing
• • 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
  • C10L1/223—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond having at least one amino group bound to an aromatic carbon atom
  • C10L1/2235—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond having at least one amino group bound to an aromatic carbon atom hydroxy containing
• • 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

Definitions

• the present invention relates to the use of fatty acid salts of alkoxylated oligoamines as lubricity improvers for mineral oil products, in particular for petrol and middle distillates, especially diesel fuels, and also additive concentrates for such mineral oil products and such mineral oil products themselves, which contain these fatty acid salts of alkoxylated oligoamines.
• Carburetors and intake systems of gasoline engines are increasingly contaminated with contaminants caused by dust particles from the air, unburned hydrocarbon residues from the combustion chamber and the crankcase ventilation gases that are led into the carburetor.
• Such pure fuel additives which can originate from a large number of chemical substance classes, such as polyalkenamines, polyetheramines, polybutene-Mannich bases or polybutensuccinimides, are generally used in combination with carrier oils and, in some cases, other additive components such as corrosion inhibitors and demulsifiers.
• Lubricity-improving additives known to date for petrol are, for example, fatty acids, such as. B. described in WO 98/11175, alkenyl succinic acid esters, bis (hydroxyalkyl) fatty amines and hydroxyacetamides.
• fatty acids and fatty acid derivatives e.g. B. esters of glycerol with unsaturated fatty acids, or castor oil, as described in EP-B 605 857, used as lubricity-improving additives.
• the object of the present invention was to provide better-effective lubricity improvers for mineral oil products, in particular for petrol and middle distillates.
• A represents alkylene groups with 2 to 8 carbon atoms, R C to C 3 alkyl groups or mono- or polyunsaturated
• n 0 or an integer from 1 to 5 and
• aqueous lubricants for conveyor belts in the filling of bottles with beverages which contain fatty acid salts of alkanolamines such as N, N, N ', N' tetrakis (2-hydroxypropyl) ethylenediamine.
• alkanolamines such as N, N, N ', N' tetrakis (2-hydroxypropyl) ethylenediamine.
• palmitic acid, tetradecanoic acid, oleic acid and lauric acid are mentioned as fatty acids.
• Mineral oil products are to be understood here as fuels, operating materials, fuels and lubricating oils, which, however, are based not only on petroleum but also partly or completely on synthetic and / or naturally occurring raw materials. Examples of such raw materials are natural gas, methanol, ethanol, hard coal liquefaction products or rapeseed oil, which are processed into fuels or incorporated into petroleum-based fuels.
• the designated mineral oil products are generally practically water-free or contain water at least only in minor quantities.
• Examples of water-containing mineral oil products 38463 4 products are fuel emulsions such as diesel / water emulsions, which can usually contain up to approx. 35% by weight of water.
• Mineral oil products preferred for the present invention are, on the one hand, petrol fuels and, on the other hand, middle distillates such as, in particular, diesel fuels.
• the alkylene group A is preferably derived from corresponding alkylene oxides such as ethylene oxide, 1, 2-propylene oxide, 1,2-butylene oxide and ice or trans-2, 3-butylene oxide. However, it can also represent 1,3-propylene, 1,4-butylene, 1,6-hexylene or 1,8-octylene. A can also represent a mixture of different of the groupings mentioned. A, ethylene, 1,2-propylene or 1,2-butylene groups are particularly preferred for A.
• the longer-chain radical R occurring in the carboxylate anion denotes, for example, branched or preferably linear C - to C 23 -, preferably Cn ⁇ to C 2 ⁇ , especially C 1 5 to C 9 alkyl groups, which may additionally carry hydroxyl groups .
• Examples of the underlying carboxylic acids are octanoic acid, 2-ethylhexanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid (lauric acid), tridecanoic acid, iso-tridecanoic acid, tetradecanoic acid (myristic acid), hexadecanoic acid (palmitic acid), stearic acid and octadecanoic acid (octadecanoic acid) ,
• the acids mentioned can be of natural or synthetic origin. Mixtures of the acids mentioned can also form the basis of the carboxylate anions.
• the longer-chain radical R occurring in the carboxylate anion preferably denotes mono- or polyunsaturated C 7 to C 3 radicals, in particular mono- or polyunsaturated Cn ⁇ to C 2 ⁇ ⁇ , especially C 15 - to cig alkenyl groups, which can also carry hydroxyl groups.
• These unsaturated residues are preferably linear.
• polyunsaturated alkenyl groups these preferably contain two or three double bonds.
• Examples of underlying carboxylic acids are elaidic acid, ricinoleic acid, linoleic acid and linolenic acid. Particularly good results are achieved with oleic acid.
• Mixtures of such unsaturated carboxylic acids with one another and also with the above-mentioned saturated carboxylic acids can also form the basis of the carboxylate anions.
• Such mixtures are, for example, tall oil, tall oil fatty acid and rapeseed oil fatty acid.
• the unsaturated carboxylic acids and the mixtures mentioned are generally of natural origin.
• variable Z means in particular C 1 -C 4 -alkylene groupings such as methylene, 1, 2-propylene, 1,2-butylene, 1,3-butylene or 2,3-butylene, C 5 - to C 6 -cycloalkylene groupings such as 1,3-cyclo pentylidene or 1,3- or 1, 4-cyclohexylidene or C ß - to Cs-arylene LEN or -Arylalkylengrupp réelleen such as 1,3- or 1, 4-phenylene, 2-methyl-l, 4-phenylene or 1, 3- or 1,4-bismethylene phenylene.
• C 1 -C 4 -alkylene groupings such as methylene, 1, 2-propylene, 1,2-butylene, 1,3-butylene or 2,3-butylene
• C 5 - to C 6 -cycloalkylene groupings such as 1,3-cyclo pentylidene or 1,3- or 1, 4-cyclohexylidene or
• variable m stands for 0, as a rule, depending on the sum (Variablen) of all variables x, mixtures of mono-, di- and / or trialkanolamines or pure trialkanolamines are based on the fatty acid salts used according to the invention as a cationic component.
• alkanolamines are monoethanolamine, diethanolamin, triethanolamine, monoisopropanolamine, diisopropanolamine, triisopropanolamine and the associated mixtures.
• variable m preferably stands for the number 1 or 2.
• m 1 there are completely and / or partially alkoxylated alkylenediamines such as 1,2-ethylenediamine, 1,3-propylenediamine or 1,4-butylenediamine.
• the basis is usually completely and / or partially alkoxylated dialkylenetriamines such as di- (1,2-ethylene) triamine, di- (1,3-propylene) triamine or di- (1,4-butylene) triamine ,
• dialkylenetriamines such as di- (1,2-ethylene) triamine, di- (1,3-propylene) triamine or di- (1,4-butylene) triamine
• OA alkylene oxide units
• over-stoichiometric incorporation a triple alkoxylation per NH bond [300% of (m + 3)] is an upper limit with regard to the properties of the resulting fatty acid salts.
• sub-stoichiometric incorporation an average 50% alkoxylation [50% of (m + 3)] o A corresponding lower limit, in this case there are usually mixtures of species with different degrees of alkoxylation.
• the sum ( ⁇ ) of all variables x has a value of 75% to 125% of (m + 3).
• the fatty acid salts of the general formula I used according to the invention can usually be easily prepared by alkoxylation of the underlying amines by customary methods and subsequent neutralization with the fatty acids of the formula R-COOH.
• the alkoxylation is expediently used for introducing the first alkylene oxide unit into the NH bond in the presence of small amounts of water (usually 0.5 to 5% by weight, based on the Amount of amine used) without catalyst at temperatures from 80 to 140 ° C and for the introduction of further alkylene oxide units with the exclusion of water in the presence of basic catalysts such as alkali metal hydroxides, eg. As sodium or potassium hydroxide, carried out at temperatures of 100 to 150 ° C.
• basic catalysts such as alkali metal hydroxides, eg. As sodium or potassium hydroxide, carried out at temperatures of 100 to 150 ° C.
• the neutralization is generally carried out by heating the alkoxylated amine thus obtained with the corresponding stoichiometric or slightly sub-stoichiometric amount (ie 90 to 100%, in particular 95 to 100% of theory) of fatty acid to temperatures of 30 to 100 ° C., in particular 40 to 80 ° C, for a period of 15 minutes to 10 hours, especially 30 minutes to 5 hours.
• the neutralization reaction should be carried out in such a way that no carboxylic ester components are formed in the product.
• both the alkoxylated amine and the fatty acid can be used as liquids, which makes the conversion to the corresponding fatty acid salt particularly simple.
• the order of combining alkoxylated amine and fatty acid is not critical, i.e. You can either add the alkoxylated amine and add the fatty acid or add the fatty acid and add the alkoxylated amine.
• the preparation of the fatty acid salts of the general formula I used in accordance with the invention usually requires significantly less effort and energy than in the case of conventional lubricity improvers of the prior art, in particular those based on amino the or esters, the production of which generally requires higher temperatures, longer reaction times and complicated work-up work to separate undesired by-products, which occur in particular in the case of condensation reactions.
• the fatty acid salts of general formula I described are outstandingly suitable as lubricity additives ("lubrication additives", “friction modifiers") in mineral oil products, in particular in petrol and middle distillates, especially diesel fuels.
• lubrication additives "friction modifiers”
• the fatty acid salts I are generally highly effective and can therefore be used widely. When fatty acid salts I are used, the tendency for wear to occur in the parts of the machines and units operated with the mineral oil products is significantly reduced.
• fatty acid salts of the general formula I used in gasoline according to the invention can advantageously be used in combination with, in principle, all customary gasoline additives.
• Polyisobutenamines which, according to EP-A 244 616, are obtained by hydroformylation of highly reactive polyisobutene with a number-average molecular weight of 300 to 5000 and subsequent reductive amination with ammonia, monoamines or polyamines such as dimethyleneaminopropylamine, ethylenediamine, diethylenetriamine or triethylenetetramine Tetraethylene pentamine are available;
• poly (iso) butenamines which can be obtained by oxidation of double bonds in poly (iso) butenes with air or ozone to give carbonyl or carboxyl compounds and subsequent amination under reducing (hydrogenating) conditions;
• polyisobutenamines which are obtainable from polyisobutene epoxides according to DE-A 196 20 262 by reaction with amines and subsequent dehydration and reduction of the amino alcohols;
• additives containing carboxylic acid ester groups preferably based on esters of mono-, di- or tricarboxylic acids with long-chain alcohols or polyols, in particular those with a minimum viscosity of 2 mm 2 / s at 100 ° C., as described in DE-A 38 38 918 are described as examples here adipates, phthalates, isophthalates, terephthalates and trimel - litates of iso-octanol, iso-nonanols, iso-decanols and iso-tridecanols - products of this type also fulfill carrier oil properties;
• Carboxyl groups or additives containing alkali metal or alkaline earth metal salts in particular such as the copolymers of C 4 -C 4 -olefins with maleic anhydride with a total molar mass of 500 to 20,000 described in EP-A 307 815, the carboxyl groups of which are wholly or partly added the alkali metal or alkaline earth metal salts and a remaining radical of the carboxyl groups are reacted with alcohols or amines;
• gasoline fuel additives (a) to (m) In addition to and together with the aforementioned gasoline fuel additives (a) to (m), other customary carrier oils, additive components and auxiliaries can be combined with the fatty acid salts of the general formula I for use in gasoline fuels.
• Base hydroogenated or non-hydrogenated
• Fractions such as kerosene, naphtha or brightstock are also suitable as mineral carrier oils and / or diluents or solvents for petrol additives.
• Aromatic hydrocarbons, paraffinic (aliphatic) hydrocarbons and alkoxyalkanols are also suitable for this.
• carrier oils for gasoline fuel additives are polyetherols which, by reacting C 2 -C 3 -alkanols, C ß -C o-alkanediols, mono-, di- or tri-C- to C 3 o -alkylamines, C ⁇ ⁇ to C 3 o-alkylcyclohexanols or C ⁇ ⁇ bis C 3 o-alkylphenols with 1 to 30 mol ethylene oxide and / or propylene oxide and / or butylene oxide per hydroxyl or amino group are available.
• alcohol-initiated polyetherols with about 10 to 35, in particular 15 to 30, propylene and / or butylene oxide units are to be mentioned here; linear or branched C 6 -C to alkanols are particularly suitable as starter alcohols.
• corrosion inhibitors for example based on ammonium salts of organic carboxylic acids which tend to form films, or heterocyclic aromatics for non-ferrous metal corrosion protection, antioxidants or stabilizers, for example based on amines such as p-phenylenediamine, dicyclohexylamine or derivatives thereof or phenols , 4-di-tert. -butylphenol or 3, 5-di-tert. -butyl-4-hydroxyphenylpropionic acid, demulsifiers, antistatic agents, metallocenes such as ferrocene or methylcyclopentadienylmanganese tricarbonyl and dyes (markers).
• amines such as p-phenylenediamine, dicyclohexylamine or derivatives thereof or phenols , 4-di-tert. -butylphenol or 3, 5-di-tert. -butyl-4-hydroxyphenylpropionic acid, demulsifiers, antistatic agents
• fatty acid salts of the general formula I used in petrol according to the invention can also be used together with other lubricity improvers which are customary for this purpose, such as certain fatty acids, alkenylsuccinic acid esters, bis (hydroxyalkyl) fatty amines or hydroxyacetamides.
• the carboxylic acids or fatty acids used as corrosion inhibitors or lubricity improvers can be present as monomeric or oligomeric, in particular dimeric, species. Mixtures of monomeric and di eren and optionally higher oligomeric species can also be present.
• Combinations of the fatty acid salts of the general formula I used in petrol according to the invention with the detergents of the above-mentioned groups (a), (d) and (g), in particular with polyisobutenamines from group (a), are preferred.
• Particularly suitable polyisobutenamines (a) are those which are prepared by hydroformylation of highly reactive polyisobutenes having a number-average molecular weight of 500 to 2300, in particular 800 to 1500, especially 900 to 1200, and subsequent reductive amination with ammonia.
• the polyisobutenamines (a) are preferably combined with carrier oils, for example polyetherols or aliphatic or aromatic hydrocarbons, and optionally with the aforementioned corrosion inhibitors, antioxidants or stabilizers, demulsifiers, antistatic agents. tic agents, metallocenes and / or dyes used.
• carrier oils for example polyetherols or aliphatic or aromatic hydrocarbons
• demulsifiers for example polyetherols or aliphatic or aromatic hydrocarbons
• demulsifiers for example polyetherols or aliphatic or aromatic hydrocarbons
• demulsifiers for example polyetherols or aliphatic or aromatic hydrocarbons
• demulsifiers demulsifiers
• antistatic agents for example, metallocenes and / or dyes used.
• Kerocom® PIBA by BASF Aktiengesellschaft.
• gasoline fuel compositions can be used as gasoline.
• the typical Eurosuper base fuel according to EN 228 should be mentioned here as a typical representative.
• fatty acid salts of the general formula I used according to the invention in middle distillates can be used advantageously in all usual middle distillates.
• middle distillates of which diesel fuels are the most important group, include petroleum raffinates, which usually have a boiling range of 100 to 400 ° C. These are mostly distillates with a 95% point up to 360 ° C or beyond. However, these can also be so-called “ultra low sulfur diesel” or "city diesel”, characterized by a 95% point of, for example, a maximum of 345 ° C. and a sulfur content of a maximum of 0.005% by weight or by a 95% point of - for example 285 ° C and a maximum sulfur content of 0.001
• these middle distillates can also be heating oils with a sulfur content of at most 0.20% by weight, in particular at most 0.10% by weight, and aviation fuels.
• distillates mentioned are usually composed of components which are obtained from the atmospheric or vacuum distillation of petroleum or which are obtained from conversion processes, e.g. B. cracker, koker or visbreaker gas oil.
• the middle distillates mentioned, above all diesel fuels are distinguished by a low sulfur content, as a rule of a maximum of 0.05% by weight, in particular a maximum of 0.02% by weight, especially a maximum of 0.005% by weight, very particularly preferably at most 0.001% by weight.
• the fatty acid salts of the general formula I used according to the invention in middle distillates, especially diesel fuels, can be incorporated therein as liquid pure substances or as liquid concentrates in a solvent or diluent.
• solvents or diluents all substances mentioned above as such agents for use with gasoline fuel additives can be used as solvents or diluents.
• Mineral oil cuts such as naphtha, kerosene, diesel fuel and aromatic hydrocarbons such as solvent naphtha heavy, Solvesso® or Shellsol® are particularly suitable.
• These concentrates can be solutions or dispersions, with clear solutions being preferred. Mixtures of the solvents or diluents mentioned can also be used.
• the solubility of the fatty acid salts of the general formula I used according to the invention can be improved.
• Such solutions or dilutions are advantageous when the middle distillate already contains further additives, when the mixing temperatures are low, when the metering device is not designed for low metering quantities or when mixtures with other middle distillates are to be produced.
• fatty acid salts of the general formula I used according to the invention in middle distillates can advantageously be used combined with in principle all common middle distillate or diesel fuel additives.
• Common middle distillate or diesel fuel additives in this context are, in particular, detergents, corrosion inhibitors, dehazers, demulsifiers, antifoams (“antifoam”), antioxidants, metal deactivators, multifunctional stabilizers, cetane number improvers, combustion improvers, dyes, markers, solubilizers, other additives, and lubricants additives which improve the cold properties, such as flow improvers (“MDFI”), paraffin dispersants (“WASA”) and their combination (“WAFI").
• MDFI flow improvers
• WASA paraffin dispersants
• WAFI additives which improve the cold properties
• the present application also relates to a process for improving the lubricity of mineral oil products, in particular petrol and middle distillates, which is characterized in that effective amounts of fatty acid salts of alkoxylated oligoamines of the general formula I 1 to 6 are added to the mineral oil products.
• the present invention furthermore relates to additive concentrates for mineral oil products, in particular for petrol and middle distillates, which contain the fatty acid salts of alkoxylated oligoamines of the general formula I in amounts of 0.05 to 50, in particular 0.1 to 30,% by weight, based on the total amount of the concentrates.
• These concentrates usually also contain the other additives, carrier oils, solution or diluents and / or auxiliaries.
• additive concentrates for petrol these are, in particular, detergents and / or valve seat anti-wear agents, in particular the additives (a) to (m) listed above, and further components and auxiliaries customary for this, in particular carrier oils,
• Corrosion inhibitors antioxidants or stabilizers, demulsifiers, antistatic agents, metallocenes and dyes.
• the present invention furthermore relates to mineral oil products, in particular gasoline and middle distillate compositions, which contain the fatty acid salts of alkoxylated oligoamines of the general formula I in effective amounts.
• Effective amounts are generally 1 to 1000 ppm by weight, in particular 5 to 500 ppm by weight, especially 10 to 250 ppm by weight, particularly preferably 20 to 100 ppm by weight, both for petrol and diesel fuel compositions .-ppm, based in each case on the total amount of the composition.
• These mineral oil products, in particular the gasoline and middle distillate compositions usually contain, in addition to the fatty acid salts I used according to the invention, the additives, additive components and auxiliaries listed above.
• the fatty acid salts of alkoxylated oligoamines of the general formula I are already highly effective in low concentrations in the mineral oil products as lubricity improvers and effectively prevent wear in the parts of the machines and units operated with the mineral oil products, for example in fuel inlet systems or injection pumps.
• the fatty acid salts of alkoxylated oligoamines of the general formula I have good compatibility with lubricating oil, which is particularly important when used in diesel fuels. Due to the interaction of acid lubricity improvers (such as dimeric fatty acids) used to date with basic constituents of lubricating oil, which is known to be in contact with the fuel in gasoline and diesel engines, corresponding salts can separate out in the fuel and at undesired points in the engine or the injection system and Cause interference. This disadvantage is avoided by the use according to the invention of the fatty acid salts of alkoxylated oligoamines of the general formula I.
• the fatty acid salts of alkoxylated oligoamines of the general formula I used according to the invention have practically no tendency to form unwanted emulsions in the mineral oil products and are sufficiently stable to hydrolysis.
• the following examples are intended to illustrate the present invention without restricting it.
• Example 1 Preparation of the bis-oleic acid salt of N, N, N ', N' -tetrakis (2'-hydroxypropyl) -1, 2-ethylenediamine
• a high frequency recrocating rig from PCS Instruments, London, was used to check the lubricity and wear in petrol.
• the measuring conditions have been adapted to the use of petrol.
• the applicability of this test method for petrol is indicated by the references D. Margaroni, Industrial Lubrication and Tribology, Vol. 50, No. 3, May / une 1998, pp. 108-118, and W. D. Ping, S. Korcek, H. Spikes, SAE Techn. Paper 962010, pp. 51-59 (1996).
• the gasoline used here (OK) (typical gasoline in accordance with EN 228) was gently reduced to 50% by volume by distillation before the measurements. This 50% residue was used in the inspection in the wear measuring device to determine the blank value. According to the examples listed below, the other additives were added to this residue and the frictional wear values were determined according to the method given above. Right. The resulting frictional wear values (R) are given in micrometers ( ⁇ m); the lower this value, the lower the wear that occurs.
• the addition of 500 mg / kg of a commercially available petrol additive package Pl (based on a polyisobutenamine detergent, a synthetic carrier oil and a conventional corrosion inhibitor) or a commercially available petrol additive package P2 (analogous to Pl but with a different synthetic carrier oil) led to this each with friction wear values in the same order of magnitude.
• Lubricity improvers from Examples 1 and 2 or from lubricity improvers known from the prior art resulted in correspondingly lower values, the products according to the invention mostly being significantly superior to those of the prior art.
• the values obtained are listed in Table 1 below.
• a commercial lubricant improver based on tall oil fatty acid according to WO 98/11175 was used as the comparative product.
• Standard lubricity tests were carried out with an HFRR device from PCS Instruments, London, in which a steel ball rubs on a steel plate in the test fuel.
• ISO 12156-1 describes this method and has found its way into the diesel standard EN 590-1999. The limit here is an abrasion on the steel ball of a maximum of 460 ⁇ m.
• Unadditized low-sulfur diesel fuels can have frictional closure values R of typically 400 to 700 ⁇ m.
• test diesel fuels (DK1 to DK4) listed in Table 2 below had the characteristics indicated,
• the sulfur content was determined in accordance with EN ISO 14 596.
• the following diesel fuel additives were used:
• Additive A product from Example 2 used according to the invention (undiluted)
• Additive B product from Example 1 used according to the invention (undiluted)
• Additive C as a comparison of commercially available lubricity improvers based on a mixture of a sterically hindered alkylphenol and a long-chain carboxylic acid
• Additive D as a comparison of commercially available lubricity improvers based on a mixture of a carboxylic acid amide and a natural fatty acid ester
• Additive E as a comparison of commercially available lubricity improvers based on a mixture of glycerol monooleate and glycerol monolinolate
• Additive F as a comparison of commercially available lubricity improvers based on a mixture of long-chain carboxylic acids
• Table 3 shows the results of the determination of the tear wear values R in the test diesel fuels. It is clear that the effect of products A and B used according to the invention exceeds that of market products C to F.

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• Chemical & Material Sciences (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Engineering & Computer Science (AREA)
• Organic Chemistry (AREA)
• Chemical Kinetics & Catalysis (AREA)
• General Chemical & Material Sciences (AREA)
• Combustion & Propulsion (AREA)
• Liquid Carbonaceous Fuels (AREA)
• Solid Fuels And Fuel-Associated Substances (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Lubricants (AREA)
• Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)

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Citations (8)

• 1999
  • 1999-11-19 DE DE19955651A patent/DE19955651A1/de not_active Withdrawn
• 2000
  • 2000-10-27 MY MYPI20005045A patent/MY123415A/en unknown
  • 2000-11-10 EP EP00977522A patent/EP1230330B1/de not_active Expired - Lifetime
  • 2000-11-10 AT AT00977522T patent/ATE263825T1/de not_active IP Right Cessation
  • 2000-11-10 SK SK700-2002A patent/SK7002002A3/sk unknown
  • 2000-11-10 RU RU2002116125/04A patent/RU2237081C2/ru not_active IP Right Cessation
  • 2000-11-10 DE DE50006014T patent/DE50006014D1/de not_active Expired - Lifetime
  • 2000-11-10 BR BR0015682-5A patent/BR0015682A/pt not_active IP Right Cessation
  • 2000-11-10 HU HU0204038A patent/HUP0204038A2/hu unknown
  • 2000-11-10 DK DK00977522T patent/DK1230330T3/da active
  • 2000-11-10 TR TR2002/01313T patent/TR200201313T2/xx unknown
  • 2000-11-10 CA CA002388065A patent/CA2388065A1/en not_active Abandoned
  • 2000-11-10 ES ES00977522T patent/ES2219415T3/es not_active Expired - Lifetime
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  • 2000-11-10 KR KR1020027006328A patent/KR20020051935A/ko not_active Application Discontinuation
  • 2000-11-10 EE EEP200200256A patent/EE200200256A/xx unknown
  • 2000-11-10 AU AU15205/01A patent/AU774943B2/en not_active Ceased
  • 2000-11-10 JP JP2001540219A patent/JP4713804B2/ja not_active Expired - Fee Related
  • 2000-11-10 IL IL14919800A patent/IL149198A/en not_active IP Right Cessation
  • 2000-11-10 NZ NZ519236A patent/NZ519236A/en unknown
  • 2000-11-10 WO PCT/EP2000/011102 patent/WO2001038463A1/de active IP Right Grant
  • 2000-11-10 PT PT00977522T patent/PT1230330E/pt unknown
  • 2000-11-10 CZ CZ20021730A patent/CZ20021730A3/cs unknown
  • 2000-11-10 PL PL00357473A patent/PL357473A1/xx unknown
  • 2000-11-15 AR ARP000106012A patent/AR028188A1/es active IP Right Grant
• 2002
  • 2002-05-15 NO NO20022319A patent/NO20022319L/no unknown
  • 2002-06-18 HR HR20020530A patent/HRP20020530B1/xx not_active IP Right Cessation
  • 2002-06-18 ZA ZA200204851A patent/ZA200204851B/xx unknown

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