WO2001036568A1 - Substances ameliorant le pouvoir lubrifiant et compositions de carburant et de lubrifiant contenant lesdites substances - Google Patents

Substances ameliorant le pouvoir lubrifiant et compositions de carburant et de lubrifiant contenant lesdites substances Download PDF

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Publication number
WO2001036568A1
WO2001036568A1 PCT/EP2000/011382 EP0011382W WO0136568A1 WO 2001036568 A1 WO2001036568 A1 WO 2001036568A1 EP 0011382 W EP0011382 W EP 0011382W WO 0136568 A1 WO0136568 A1 WO 0136568A1
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Prior art keywords
additive
additive mixture
oil
mixture according
fuel
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PCT/EP2000/011382
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German (de)
English (en)
Inventor
Siegbert Brand
Dietmar Posselt
Original Assignee
Basf Aktiengesellschaft
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Publication date
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Priority to DK00985046T priority Critical patent/DK1230328T3/da
Priority to DE2000508267 priority patent/DE50008267D1/de
Priority to AT00985046T priority patent/ATE279497T1/de
Priority to JP2001539048A priority patent/JP2003514953A/ja
Priority to KR1020027006338A priority patent/KR20020052212A/ko
Priority to CA002391932A priority patent/CA2391932A1/fr
Priority to EP00985046A priority patent/EP1230328B1/fr
Publication of WO2001036568A1 publication Critical patent/WO2001036568A1/fr
Priority to NO20022357A priority patent/NO20022357L/no

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    • 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
    • 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
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/68—Esters
    • C10M129/70—Esters of monocarboxylic acids
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    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/68—Esters
    • C10M129/74—Esters of polyhydroxy compounds
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    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/16—Amides; Imides
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    • C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
    • C10M141/06—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic nitrogen-containing compound
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    • C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
    • C10M159/02—Natural products
    • C10M159/08—Fatty oils
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    • C10M163/00—Lubricating compositions characterised by the additive being a mixture of a compound of unknown or incompletely defined constitution and a non-macromolecular compound, each of these compounds being essential
    • C—CHEMISTRY; METALLURGY
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    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/16—Hydrocarbons
    • C10L1/1625—Hydrocarbons macromolecular compounds
    • C10L1/1633—Hydrocarbons macromolecular compounds homo- or copolymers obtained by reactions only involving carbon-to carbon unsaturated bonds
    • C10L1/1641—Hydrocarbons macromolecular compounds homo- or copolymers obtained by reactions only involving carbon-to carbon unsaturated bonds from compounds containing aliphatic monomers
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    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
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    • C10L1/00—Liquid carbonaceous fuels
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    • 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
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    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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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
    • C10L1/224—Amides; Imides carboxylic acid amides, imides
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    • C10L1/00—Liquid carbonaceous fuels
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    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/234—Macromolecular compounds
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    • 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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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
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    • C10M2207/28—Esters
    • C10M2207/284—Esters of aromatic monocarboxylic acids
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    • C10M2207/40—Fatty vegetable or animal oils
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40—Fatty vegetable or animal oils
    • C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
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Definitions

  • the invention relates to additive mixtures, their use to improve the lubricity of fuels and to improve the wear resistance of engines, and fuel compositions and additive packages containing them, and their use as lubricant additives.
  • the first generation of additives could only prevent the formation of deposits in the intake system, but not remove existing deposits, whereas the modern additives of the second generation can do both (keep-clean and clean-up effect), and in particular also due to their excellent thermostability in zones of higher temperature, namely at the inlet valves.
  • R represents an optionally unsaturated C -C 4 bridging group which can optionally be mono- or polysubstituted
  • R 1 represents NR 3 R 4 , wherein
  • R 3 and R 4 are the same or different and represent a straight-chain or branched aliphatic radical selected from C 8 -C _ alkyl, mono- or polyunsaturated Cg-C o-alkenyl, Cs-C o-alkyloxy, and single or multiple unsaturated Cg-C o-alkenyloxy, stand; or one of the radicals R 3 and R 4 is H and the other radical is an aliphatic radical as defined above;
  • R 2 represents OH or 0 ⁇ NR 5 R 6 + , wherein
  • R 5 and R 6 independently of one another and independently of R 3 and R 4 have the meanings given for R 3 and R 4 ;
  • the two components are in a volume ratio of approximately 1:10 to 10: 1, in particular approximately 1: 5 to 5: 1.
  • additive mixtures according to the above definition are provided, in which the radical R is C -C 4 -alkylene or -ethenylene.
  • Suitable substituents on the radical R are, for example, hydroxyl, C ⁇ -C-alkyl, such as methyl and ethyl, and hydroxy-C ⁇ -C-alkyl, such as hydroxymethyl and hydroxyethyl.
  • Suitable cyclic dicarboxylic acid derivatives which can be used to prepare compounds of the general formula I include, in particular, the cyclic dicarboxylic acid anhydrides.
  • Preferred anhydrides are maleic anhydride and succinic acid reanhydride and the corresponding substituted analogues thereof.
  • Other suitable carboxylic acid derivatives are dicarboxylic acid esters, in particular esters of C 1 -C 0 monools, the C 1 -C 0 monools being defined as indicated below for the fatty acid esters.
  • radicals R 3 , R 4 , R 5 and R 6 in compounds of the formula I are C 8 -C 20 alkyl, such as n-octyl, n-nonyl, n-decyl, n-undecyl, n- Tridecyl, n-tetradecyl, n-pentadecyl and n-hexadecyl, and the one or more branched analogues thereof.
  • Examples of suitable Cg-C 2 o-alkenyl radicals are the mono- or polyunsaturated, preferably monounsaturated, analogues of the alkyl radicals mentioned above, it being possible for the double bond to be located in any position in the carbon chain.
  • Examples of suitable Cg-C o-alkyloxy and alkenyloxy radicals are the oxygen-terminated analogs of the above-mentioned alkyl and alkenyl radicals.
  • Preferred long-chain aliphatic amines which are used for the reaction with the dicarboxylic acid or the dicarboxylic acid derivative are primary or secondary amines with one or two identical or different Cg-C 2 o -alkyl or alkenyl radicals, in particular decylamine, undecylamine, dodecylamine, tridecylamine, tradecylamine, pentadecylamine and hexadecylamine and the corresponding secondary amines with two identical aliphatic radicals.
  • Further examples are fatty amines and fatty amine mixtures, for example those with 16 to 18 carbon atoms.
  • Suitable fatty acid esters are composed of straight-chain or branched, mono- or polyunsaturated, optionally substituted C 6 -C 30 monocarboxylic acids and a mono- or polyhydric, preferably mono- to trihydric alcohol.
  • Polyhydric alcohols can be partially or completely esterified with the same or a different fatty acid.
  • saturated unbranched fatty acids are caproic acid, oenanthic acid, caprylic acid, pelargonic acid, capric acid, undecanoic acid, lauric acid, tridecanoic acid, myristic acid, pentadecanoic acid, palmitic acid, margaric acid, stearic acid, nonadecanoic acid, arachidic acid, behenic acid, ceric acidic acid and lignic acidic acid.
  • monounsaturated fatty acids are palmitoleic acid, oleic acid and erucic acid.
  • di-unsaturated fatty acids are sorbic acid and linoleic acid.
  • triple unsaturated fatty acids are linolenic acid and elaeostearic acid.
  • four- and poly-unsaturated fatty acids are arachidonic acid, clupanodonic acid and docosahexaenoic acid.
  • substituted fatty acids are ricinoleic acid ((R) -12-Hy- droxy- (Z) -9-octadecenoic acid).
  • Other suitable fatty acids are naturally occurring fatty acids such as gondo acid and neronic acid. If double bonds are contained in the fatty acids, they can be in either ice or trans form.
  • the substituents are preferably selected from hydroxy and lower alkyl groups, such as methyl and ethyl groups.
  • keto groups or epoxy groups such as, for example, in the vernolic acid can be contained in the hydrocarbon radical.
  • Other functional groups are cyclopropane, cyclopropene and cyclopentene rings, which can be formed by bridging two adjacent carbon atoms in the hydrocarbon residue of the fatty acid (cf. malvalic acid and chaulmoogras acid).
  • suitable alcohols are C 1 -C 1 -monools, such as, in particular, methanol, ethanol, n-propanol, n-butanol, n-pentanol and the corresponding branched analogues thereof.
  • suitable diols are C 2 -C 6 diols such as ethane-1, 2-diol, propane-1, 3-diol, butane-1, 2-diol and pentane-1, 2-diol and the corresponding positional isomers of these diols
  • suitable higher alcohols are, in particular, glycerol and sugar alcohols, such as, for example, sorbitol and inositol, pentaerythritol and trimethylolpropane.
  • the preferred polyhydric alcohol is glycerin.
  • a preferred group of fatty acid esters comprises triglycerides of the same or different fatty acids as defined above or mixtures of such triglycerides and mixtures of such triglycerides with the corresponding mono- and / or diglycerides.
  • Triglycerides of natural origin such as those found, for example, in vegetable oils, are particularly preferably used. Examples of particularly suitable vegetable oils are rapeseed oil, coconut oil, palm kernel oil, corn oil, olive oil, soybean oil, sunflower oil, linseed oil, peanut oil and castor oil.
  • the triglycerides which can be used according to the invention can be isolated from these oils. Unless it lyceridgehalt the Trig such oils permits may this- 'the additive compositions of the invention can be added directly. For example, technical castor oil can be used in the additive mixtures according to the invention without further fractionation.
  • Further objects of the present invention relate to the use of the additive mixtures according to the invention to improve the lubricity of gasoline fuels and / or to improve the wear resistance of gasoline engines.
  • the invention further relates to fuel compositions, in particular for gasoline engines, which, in addition to a main amount of a hydrocarbon fuel, contain an amount of at least one additive mixture according to the present invention which improves the lubricity, optionally in combination with other conventional borrowed fuel additives.
  • Other objects are additive concentrates containing an additive mixture according to the invention in combination with other customary additive components in solid or optionally dissolved or dispersed form.
  • Preferred synergistic combinations include reaction products of carboxylic anhydrides with primary or secondary alkyl or alkenyl amines in a mixture with triglycerides. Mixtures of reaction products of maleic anhydride with primary or secondary alkylamines are particularly preferred
  • Chain length Cg-Cig e.g. Tridecylamine or ditridecylamine, and castor oil.
  • the additive mixture according to the invention can be used alone or in combination with further fuel additives, for example the detergent additives already mentioned above and described in more detail below.
  • gasoline additives used in addition to the fuel additives according to the invention are, for example, those which contain at least one hydrophobic hydrocarbon radical with a number-average molecular weight (M n ) of 85 to 20,000 and at least one polar grouping which is selected from
  • the hydrophobic hydrocarbon residue in these detergent additives which ensures sufficient solubility in the fuel, has a number average molecular weight (M n ) from 85 to 20,000, in particular from 113 to 10,000, especially from 300 to 5,000.
  • M n number average molecular weight
  • Examples of fuel additives with polar groups (a) are polyalkene mono- or polyalkene polyamines or functional derivatives thereof, in particular poly-C 2 -C 5 -alkenamines or functional derivatives thereof, such as, for example, based on polypropene, polybutene or polyisobutene.
  • CD p in P 3 in 3 TJ li o * in a H- o 00 ro ro H- tn Z 3 3 3 ro 3 a 03 rt 0 i tn
  • Additives containing carboxyl groups or their alkali metal or alkaline earth metal salts (d) are preferably copolymers of C 2 -C 40 olefins with maleic anhydride with a total molar mass of 500 to 20,000, the carboxyl groups of which are wholly or partly to the alkali metal or alkaline earth metal salts and a remaining radical of the carboxyl groups are reacted with alcohols or amines.
  • Such additives are known in particular from EP-A 307 815.
  • Such additives mainly serve to prevent valve seat wear and, as described in WO-A 87/01126, can advantageously be used in combination with conventional fuel detergents such as poly (iso) butenamines or polyetheramines.
  • Additives containing sulfonic acid groups or their alkali metal or alkaline earth metal salts are preferably alkali metal or alkaline earth metal salts of an alkyl sulfosuccinic acid ester, as described in particular in EP-A-639 632.
  • Such additives mainly serve to prevent valve seat wear and can advantageously be used in combination with conventional fuel detergents such as poly (iso) butenamines or polyetheramines.
  • Additives containing polyoxy-C 2 -C 4 -alkylene groupings (f) are preferably polyethers or polyetheramines which are obtained by reacting C 2 -C 6 -alkanols, C 6 -C 3 -alkanediols, mono- or di-C 2 - C 3 o-alkylamines, -C-C 3 o-alkylcyclohexanols or -C-C 3 n-alkylphenols with 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 the polyether amines, by subsequent reductive amination with ammonia, monoamines or polyamines are available.
  • poly-C 2 -C 6 -alkylene oxide amines or functional derivatives thereof can be used as polyether amines.
  • polyethers such products also have carrier oil properties. Typical examples of this are tridecanol or isotridecanol butoxylates, isononyl phenol butoxylates and polyisobutenol butoxylates and propoxylates as well as the corresponding reaction products with ammonia.
  • Additives containing carboxylic ester groups (g) are preferably esters of mono-, di- or tricarboxylic acids with long-chain alkanols or polyols, in particular those with a minimum viscosity of 2 mm / s at 100 ° C., as described in particular in DE-A-38 38 918 are described.
  • mono-, di- or tricarbon Acids can be aliphatic or aromatic acids; long-chain representatives with, for example, 6 to 24 carbon atoms are particularly suitable as ester alcohols or polyols.
  • esters are adipates, phthalates, isophthalates, terephthalates and trimellitates of isooctanol, isononanol, isodecanol and isotridecanol. Such products also have carrier oil properties.
  • Derivatives with aliphatic polyamines such as ethylene diamine, diethylene triamine, triethylene tetramine or tetraethylene pentamine are of particular interest.
  • Such gasoline fuel additives are described in particular in US-A-4,849,572.
  • Groupings (i) containing additives produced by Mannich reaction of substituted phenols with aldehydes and mono- or polyamines are preferably reaction products of polyisobutene-substituted phenols with formaldehyde and mono- or polyamines such as ethylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine or dimethylamino-propylamine ,
  • Such "polyisobutene Mannich bases" are described in particular in EP-A 831 141.
  • Particularly useful detergent additives are sold by BASF AG, Ludwigshafen, under the trade name Kerocom® PIBA. These contain polyisobutenamines dissolved in aliphatic C 1 -C 1 hydrocarbons.
  • Kerocom® PIBA polyisobutenamines dissolved in aliphatic C 1 -C 1 hydrocarbons.
  • the gasoline fuel additives according to the invention and / or additive gasoline fuels according to the invention can also contain other customary components and additives, such as, for example, carrier oils, corrosion inhibitors, demulsifiers and dyes.
  • Mineral carrier oils synthetic carrier oils and mixtures thereof which are compatible with the additive (s) and the petrol used are examples of useful carrier oils or carrier oil liquids.
  • Suitable mineral carrier oils are petroleum fractions such as kerosene or naphtha, bright stock or base oils with viscosities such as those from the SN 500-2000 class, but also aromatic hydrocarbons, paraffinic hydrocarbons and alkoxyalkanols.
  • Suitable synthetic carrier oils are polyolefins, (poly) esters, (poly) alkoxylates and in particular polyethers, aliphatic polyetheramines, alkylphenol-started polyethers and alkylphenol-started polyetheramines.
  • Suitable carrier oil systems are described for example in DE-A-38 38 918, DE-A-38 26 608, DE-A-41 42 241, DE-A-43 09 074, US-A-4, 877, 416 and EP- A-0 452 328, to which express reference is made here.
  • alkanol-started polyethers with about 10 to 35, for example about 15 to 30, C 3 -C 6 -alkylene oxide units, for example under propylene oxide, n-butylene oxide and i-butylene oxide units or mixtures thereof are selected.
  • corrosion inhibitors for example based on ammonium salts of organic carboxylic acids which tend to form films, or of 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 such as 2,4 -Diet. -butylphenol or 3, 5-di-tert. -butyl-4-hydroxyphenylpropionic acid, demulsifiers, antistatic agents, metallocenes such as ferrocene or methylcyclopentadienylmanganese tricarbonyl, others
  • Lubricity improvers such as certain fatty acids, alkenylsuccinic acid esters, bis (hydroxyalkyl) fatty amines or hydroxyacetamides and dyes (markers). If necessary, amines are also added to lower the pH of the fuel.
  • the fuel additive combinations according to the invention optionally in combination with one or more of the above-mentioned further fuel additives with the polar groups (a) to (i) and the other components mentioned, are metered into the fuel and develop their effect there.
  • the components or additives can be added to the fuel individually or as a previously prepared concentrate (“additive package”).
  • Solvents or diluents are aliphatic and aromatic hydrocarbons, e.g. Solvent naphtha or kerosene.
  • the fuel additive mixtures according to the invention are added to the fuel, for example, in an amount in the range from 10 to 150 ppm (mg / kg fuel), preferably 20 to 100 ppm (mg / kg fuel).
  • the further fuel additives with the polar groups (a) to (i) are usually added to the petrol in an amount of 10 to 5000 ppm, in particular 50 to 1000 ppm, and the other components and additives mentioned, if desired, in amounts customary for this.
  • the petrol to which the fuel additive mixtures according to the invention are added is not subject to any particular restrictions.
  • a fuel according to EN 228 is a fuel according to EN 228.
  • the fuel can be, for example, a petrol with an aromatic content of at most 42% by volume, such as 30 to 42% by volume and a maximum sulfur content of 150 ppm, e.g. 5 to 150 ppm.
  • the petrol can also have a maximum olefin content of 21% by volume, e.g. have from 6 to 21 vol .-%.
  • the benzene content can be a maximum of 1.0% by volume, e.g. 0.5 to 1.0% by volume; the oxygen content can e.g. are in the range from 1.0 to 2.7% by weight.
  • the alcohol and ether content in petrol is usually relatively low. Typical maximum contents are 3% by volume for methanol, 5% by volume for ethanol, 10% by volume for isopropanol, 7% by volume for tert-butanol, 10% by volume for isobutanol and with for ether 5 or more carbon atoms in the molecule 15 vol .-%.
  • the summer vapor pressure of petrol is usually a maximum of 70 kPa, especially 60 kPa (each at 37 ° C).
  • the research octane number ("RON") of gasoline is usually 90 to 100.
  • Motor octane number is 80 to 90.
  • HFRR device High Frequency Reciprocating Rig; HFR2 from PCS Instruments, London
  • vibrational wear tribometer such as described in EP-A-0 605 857. Measurement conditions adapted to petrol were chosen. The applicability of these test methods is documented in D. Margaroni, Industrial Lubrication and Tribology, Vol. 50, No. 3, May / June 1998, 108-118 and W.D. Ping, S. Korcek, H. Spikes, SAE Techn. Paper 962010, 51-59 (1996).
  • the gasoline used (typical gasoline according to EN 228) was gently distilled to 50% by volume of the original volume before the measurement. This 50% residue was used as a blank value test in the wear measuring device and was added according to the examples listed below with the fuel additive mixtures or additive components according to the invention. The resulting friction wear value is given in micrometers. The lower this value is, the lower the wear that occurs.
  • a fuel additive mixture according to the invention was produced by mixing the components MSA (maleic anhydride) / tridecylamine condensation product (50% by weight) and castor oil (technically, 50% by weight). The mixing of the components was advantageously carried out at approx. 50 ° C. The condensation product was introduced and then castor oil was slowly added with thorough stirring. The mixture was thoroughly stirred or rolled until a homogeneous mixture resulted. The condensation product was prepared beforehand by introducing MA (1.6 parts by weight) in solvent (5 parts by weight of solvent naphtha) and adding tridecylamine (3.4 parts by weight) in such a way that the reaction temperature Do not exceed 90 ° C.
  • Example 2 (comparison):

Abstract

L'invention concerne des mélanges d'additifs comprenant a) le produit de la réaction d'un acide dicarboxylique ou d'un dérivé de ce dernier avec une amine aliphatique à longue chaîne ; et b) un ester d'acide gras naturel. L'invention concerne également l'utilisation de ces mélanges d'additifs pour améliorer le pouvoir lubrifiant de carburants et la résistance à l'usure de moteurs. L'invention concerne en outre des compositions de carburant et de lubrifiant contenant lesdits mélanges d'additifs.
PCT/EP2000/011382 1999-11-17 2000-11-16 Substances ameliorant le pouvoir lubrifiant et compositions de carburant et de lubrifiant contenant lesdites substances WO2001036568A1 (fr)

Priority Applications (8)

Application Number Priority Date Filing Date Title
DK00985046T DK1230328T3 (da) 1999-11-17 2000-11-16 Smöreevneforbedrere og brændstof- og smörestof- sammensætninger indeholdende disse
DE2000508267 DE50008267D1 (de) 1999-11-17 2000-11-16 Schmierfähigkeitsverbesserer und diese enthaltende kraftstoff- und schmierstoffzusammensetzungen
AT00985046T ATE279497T1 (de) 1999-11-17 2000-11-16 Schmierfähigkeitsverbesserer und diese enthaltende kraftstoff- und schmierstoffzusammensetzungen
JP2001539048A JP2003514953A (ja) 1999-11-17 2000-11-16 潤滑性改良剤ならびにこれを含有する燃料組成物および潤滑剤組成物
KR1020027006338A KR20020052212A (ko) 1999-11-17 2000-11-16 윤활성 개선제 및 이를 포함하는 윤활제 조성물 및 연료
CA002391932A CA2391932A1 (fr) 1999-11-17 2000-11-16 Substances ameliorant le pouvoir lubrifiant et compositions de carburant et de lubrifiant contenant lesdites substances
EP00985046A EP1230328B1 (fr) 1999-11-17 2000-11-16 Substances ameliorant le pouvoir lubrifiant et compositions de carburant et de lubrifiant contenant lesdites substances
NO20022357A NO20022357L (no) 1999-11-17 2002-05-16 Smöreevne-forbedringsmiddel og et brensel og smöremiddelsammensetninger inneholdende nevnte middel

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19955354A DE19955354A1 (de) 1999-11-17 1999-11-17 Schmierfähigkeitsverbesserer und diese enthaltende Kraftstoff- und Schmierstoffzusammensetzungen
DE19955354.8 1999-11-17

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DE (2) DE19955354A1 (fr)
DK (1) DK1230328T3 (fr)
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Publication number Priority date Publication date Assignee Title
WO2017006167A1 (fr) 2015-07-06 2017-01-12 Rhodia Poliamida E Especialidades Ltda Compositions de diesel présentant un indice de cétane et des performances de pouvoir lubrifiant améliorés

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DE102004038113A1 (de) 2004-08-05 2006-03-16 Basf Ag Stickstoffhaltige heterocyclische Verbindungen als Reibverschleißvermindernder Zusatz zu Kraftstoffen
CA2551619A1 (fr) * 2006-07-07 2008-01-07 1692124 Ontario Inc. Additif a carburant
CN101205489B (zh) * 2006-12-18 2012-01-25 中国石油化工股份有限公司 一种燃料油添加剂组合物、其制备方法及其应用
FR3077299B1 (fr) * 2018-02-01 2020-10-30 Tropical Essence Sdn Bhd Additif pour huile a base de triglycerides

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US3961915A (en) * 1974-12-27 1976-06-08 Exxon Research And Engineering Company Synergistic additive in petroleum middle distillate fuel
US4211534A (en) * 1978-05-25 1980-07-08 Exxon Research & Engineering Co. Combination of ethylene polymer, polymer having alkyl side chains, and nitrogen containing compound to improve cold flow properties of distillate fuel oils
US5151205A (en) * 1991-05-13 1992-09-29 Texaco Inc. Chain and drive gear lubricant
WO1996018706A1 (fr) * 1994-12-13 1996-06-20 Exxon Chemical Patents Inc. Compositions de fuel-oil

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US3567644A (en) * 1968-05-21 1971-03-02 Chevron Res Hydraulic fluid containing 1,4,5,6,7,7-hexachlorobicyclo - (2.2.1) - hept - 5-ene-2-yl-methyl alkanoate base
US3961915A (en) * 1974-12-27 1976-06-08 Exxon Research And Engineering Company Synergistic additive in petroleum middle distillate fuel
US4211534A (en) * 1978-05-25 1980-07-08 Exxon Research & Engineering Co. Combination of ethylene polymer, polymer having alkyl side chains, and nitrogen containing compound to improve cold flow properties of distillate fuel oils
US5151205A (en) * 1991-05-13 1992-09-29 Texaco Inc. Chain and drive gear lubricant
WO1996018706A1 (fr) * 1994-12-13 1996-06-20 Exxon Chemical Patents Inc. Compositions de fuel-oil

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WO2017006167A1 (fr) 2015-07-06 2017-01-12 Rhodia Poliamida E Especialidades Ltda Compositions de diesel présentant un indice de cétane et des performances de pouvoir lubrifiant améliorés
WO2017006141A1 (fr) 2015-07-06 2017-01-12 Rhodia Poliamida E Especialidades Ltda Compositions de diesel présentant un indice de cétane et des performances de pouvoir lubrifiant améliorés
US11072753B2 (en) 2015-07-06 2021-07-27 Rhodia Poliamida E Especialidades S.A. Diesel compositions with improved cetane number and lubricity performances

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PT1230328E (pt) 2005-02-28
NO20022357L (no) 2002-06-26
EP1230328A1 (fr) 2002-08-14
EP1230328B1 (fr) 2004-10-13
ES2228644T3 (es) 2005-04-16
JP2003514953A (ja) 2003-04-22
ATE279497T1 (de) 2004-10-15
NO20022357D0 (no) 2002-05-16
KR20020052212A (ko) 2002-07-02
DE19955354A1 (de) 2001-05-23
DK1230328T3 (da) 2005-02-14
CA2391932A1 (fr) 2001-05-25
DE50008267D1 (de) 2004-11-18

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