Classifications

• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/003—Marking, e.g. coloration by addition of pigments
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/18—Organic compounds containing oxygen
  • C10L1/185—Ethers; Acetals; Ketals; Aldehydes; Ketones
  • C10L1/1857—Aldehydes; Ketones
• • 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
• • 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
  • C10L1/232—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M171/00—Lubricating compositions characterised by purely physical criteria, e.g. containing as base-material, thickener or additive, ingredients which are characterised exclusively by their numerically specified physical properties, i.e. containing ingredients which are physically well-defined but for which the chemical nature is either unspecified or only very vaguely indicated
  • C10M171/007—Coloured or dyes-containing lubricant compositions
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/08—Aldehydes; Ketones
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
  • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
  • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
  • C10M2215/068—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings having amino groups bound to polycyclic aromatic ring systems, i.e. systems with three or more condensed rings
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
  • C10N2040/00—Specified use or application for which the lubricating composition is intended
  • C10N2040/42—Flashing oils or marking oils

Definitions

• the present invention relates to fuel and lubricant additive concentrates which comprise at least one anthraquinone derivative as a marker, to the use of such concentrates for additizing mineral oils, and also to mineral oils which comprise such concentrates.
• additive concentrates also referred to herein below, following the relevant terminology, as packages
• packages which, in addition to a carrier oil and a mixture of different fuel additives, generally also comprise dyes and also, for invisible fiscal or manufacturer-specific marking, additionally markers.
• packages enable the supply of different mineral oil distributors from a pool of unadditized mineral oil, to which the company-specific additization, color and marker are imparted only, for example, while the mineral oil is being filled into appropriate transport containers, with the aid of their individual packages.
• the markers are usually substances which are either extracted from the mineral oil and subsequently converted to colored compounds by derivatization, or substances which exhibit absorption either in the visible or in the invisible wavelength region of the spectrum (for example in the NIR).
• Markers which have been proposed and find use per se, i.e. not just after preceding derivatization, include highly differing compound classes, for example phthalocyanines, naphthalocyanines, nickel-dithiolene complexes, aminium compounds of aromatic amines, methine dyes and azulenesquaric acid dyes (for example WO 94/02570 A1, WO 96/10620 A1), but also bisazo dyes (for example EP 256 460 A1).
• Anthraquinone derivatives for coloring gasoline or mineral oils are described in the documents U.S. Pat. Nos. 2,611,772, 2,068,372, EP 1 001 003 A1 and EP 1 323 811 A2.
• the fuel and lubricant additive concentrates (packages) mentioned at the outset have been found, which comprise at least one anthraquinone derivative as a marker.
• the components of the inventive packages are in particular:
• the component a) used is in particular anthraquinone derivatives which are selected from the group consisting of the compounds
• R 4 to R 8 are each independently hydrogen, R or NHR and
• C 1 -C 20 -Alkyl which is optionally interrupted by from 1 to 4 oxygen atoms in ether function include, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, 2-methylpentyl, heptyl, hept-3-yl, octyl, 2-ethylhexyl, isooctyl, nonyl, isononyl, decyl, isodecyl, undecyl, dodecyl, tridecyl, 3,5,5,7-tetramethylnonyl, isotridecyl (the above terms isooctyl, isononyl, isodecyl and isotridecyl are trivial names
• Useful C 5 -C 7 -cycloalkyl radicals include cyclopentyl, cyclohexyl and cycloheptyl. These cycloalkyls are optionally substituted by one or more, in particular up to three, C 1 -C 20 -alkyl groups, and the latter may optionally be interrupted by from 1 to 4 oxygen atoms in ether function. Examples of such C 1 -C 20 -alkyl groups optionally interrupted by oxygen atoms have already been listed above.
• Saturated, heterocyclic five- or six-membered radicals which are optionally substituted by one or more C 1 -C 20 -alkyl groups which are optionally interrupted by from 1 to 4 oxygen atoms in ether function are derived, for example, from pyrrolidine, 2- or 3-methylpyrrolidine, 2,4-dimethyl-3-ethylpyrrolidine, pyrazolidine, 2-, 3-, 4- or 5-methylpyrazolidine, imidazolidine, 2-, 3-, 4- or 5-methylimidazolidine, oxazolidine, 2-, 4- or 5-methyloxazolidine, isoxazolidine, 3-, 4- or 5-methylisoxazolidine, piperidine, 2-, 3-, 4-methyl- or -ethylpiperidine, 2,6-dimethylpiperidine, piperazine, 4-(C 1 -C 4 -alkyl)piperazine such as 4-methyl- or 4-ethylpiperazine, morpholine, thiomorpholine or thi
• NHR and NR 2 groups of the definition of the variables Z 1 and/or Z 2 , in the OR and NHR groups of the definition of the variables X, in the COOR group of the definition of the R 9 and R 10 radicals, in the NHR group of the definition of the variables R 3 and also R 4 to R 8 corresponds to an appropriate, optionally substituted, saturated, heterocyclic five- or six-membered radical, it is bonded to the particular heteroatom of the group in question via a carbon atom of the heterocyclic five- or six-membered ring.
• R alone in the definition of the variables R 1 and R 2 and the definition of the variables R 3 corresponds to an appropriate, optionally substituted, saturated, heterocyclic five- or six-membered radical.
• the bonding may either be via a carbon atom or a heteroatom of the heterocyclic five- or six-membered radical which are suitable for bonding.
• C 6 -C 10 -Aryls include in particular phenyl and naphthyl. These are optionally substituted by one or more halogen such as fluorine, chlorine or bromine, cyano, nitro, hydroxyl, amino, C 1 -C 20 -alkyl which is optionally interrupted by from 1 to 4 oxygen atoms in ether function, C 1 -C 20 -alkoxy, C 1 -C 20 -alkylamino or C 1 -C 20 -dialkylamino.
• halogen such as fluorine, chlorine or bromine
• cyano cyano
• nitro hydroxyl
• amino amino
• C 1 -C 20 -alkyl which is optionally interrupted by from 1 to 4 oxygen atoms in ether function
• C 1 -C 20 -alkoxy C 1 -C 20 -alkylamino or C 1 -C 20 -dialkylamino.
• C 1 -C 20 -alkyl radicals which are optionally interrupted by from 1 to 4 oxygen atoms in ether function
• C 1 -C 20 -alkyl radicals which are present in the C 1 -C 20 -alkoxy, C 1 -C 20 -alkylamino or C 1 -C 20 -dialkylamino groups have already been listed above by way of example.
• Heteroaryl radicals having from 3 to 12 carbon atoms which are optionally substituted by one or more C 1 -C 20 -alkyl which is optionally interrupted by from 1 to 4 oxygen atoms in ether function, C 1 -C 20 -alkoxy, C 1 -C 20 -alkylamino or C 1 -C 20 -dialkylamino are derived, for example, from pyrrole, furan, thiophene, pyrazole, isoxazole, isothiazole, imidazole, 1H-1,2,3-triazole, 1H-1,2,4-triazole, pyridine, pyrazine, pyridazine, 1H-azepine, 2H-azepine, oxazole, thiazole, 1,2,3-, 1,2,4- or 1,3,4-oxadiazole, 1,2,3-, 1,2,4- or 1,3,4-thiadiazole and also optionally the benzo or dibenz
• NHR and NR 2 groups of the definition of the variables Z 1 and/or Z 2 , in the OR and NHR groups of the definition of the variables X, in the COOR group of the definition of the R 9 and R 10 radicals, in the NHR group of the definition of the variables R 3 and also R 4 to R 8 corresponds to an appropriate, optionally substituted heteroaryl, it is bonded to the particular heteroatom of the group in question via a carbon atom of the heteroaryl.
• R alone in the definition of the variables R 1 and/or R 2 and the definition of the variables R 3 corresponds to an appropriate, optionally substituted heteroaryl.
• the bonding may either be via a carbon atom or a heteroatom of the heteroaryl which is suitable for bonding.
• C 6 -C 10 -Aryl-C 1 -C 4 -alkyls which are optionally substituted in the aryl radical by one or more halogen, cyano, nitro, hydroxyl, amino, C 1 -C 20 -alkyl which is optionally interrupted by from 1 to 4 oxygen atoms in ether function, C 1 -C 20 -alkoxy, C 1 -C 20 -alkylamino or C 1 -C 20 -dialkylamino include in particular benzyl, phenylethyl, 3-phenylpropyl and 4-phenylbutyl.
• C 1 -C 20 -alkyl radicals which are optionally interrupted by from 1 to 4 oxygen atoms in ether function
• C 1 -C 20 -alkyl radicals which are present in the C 1 -C 20 -alkoxy, C 1 -C 20 -alkylamino or C 1 -C 20 -dialkylamino groups have already been listed above by way of example.
• Heteroaryl-C 1 -C 4 -alkyls having from 3 to 12 carbon atoms in the heteroaryl radical, the latter optionally being substituted by one or more C 1 -C 20 -alkyl which is optionally interrupted by from 1 to 4 oxygen atoms in ether function, C 1 -C 20 -alkoxy, C 1 -C 20 -alkyl-amino or C 1 -C 20 -dialkylamino are derived, for example, from the heteroaryl radicals specified above which are bonded to the C 1 -C 4 -alkyl radicals either via a carbon atom or a heteroatom of the heteroaryl which is suitable for bonding.
• C 1 -C 20 -alkyl radicals which are optionally interrupted by from 1 to 4 oxygen atoms in ether function
• C 1 -C 20 -alkyl radicals which are present in the C 1 -C 20 -alkoxy, C 1 -C 20 -alkylamino or C 1 -C 20 -dialkylamino groups have already been listed above by way of example.
• Preferred inventive fuel and lubricant additive concentrates comprise anthraquinone derivatives of the formulae I, II and III where
• Anthraquinone derivatives of the formula I are in particular the compounds of the formulae Ia to If shown below:
• variables R are in each case independently, and in formula If the variable R is, C 1 -C 15 -alkyl which is optionally interrupted by from 1 to 4 oxygen atoms in ether function, and C 6 -C 10 -aryl which is optionally substituted by one or more C 1 -C 15 -alkyl which is optionally interrupted by from 1 to 4 oxygen atoms in ether function.
• the variables R are preferably selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, 2-methylpentyl, heptyl, hept-3-yl, octyl, 2-ethylhexyl, isooctyl, nonyl, isononyl, decyl, isodecyl, undecyl, dodecyl, tridecyl, 3,5,5,7-tetramethylnonyl, isotridecyl, tetradecyl, pentadecyl, methoxymethyl,
• the variables R are preferably selected from the group consisting of unsubstituted phenyl, the 2-, 3- and 4-monosubstituted, the 2,3-, 2,4- and 3,4-disubstituted and the 2,3,4-, 2,3,5-, 2,3,6-, 2,4,5-, 2,4,6- and 3,4,5-trisubstituted phenyl radicals which are substituted by the C 1 -C 15 -alkyl radicals which are optionally interrupted by oxygen in ether function and have been listed above by way of example.
• R radicals in the compounds of the formulae Ia to Ie are preferably the same.
• Anthraquinone derivatives of the formula II are in particular the compounds of the formulae IIa to IIc shown below:
• the variables R, R 1 and R 2 are each independently C 1 -C 15 -alkyl which is optionally interrupted by from 1 to 4 oxygen atoms in ether function, and C 6 -C 10 -aryl which is optionally substituted by one or more C 1 -C 15 -alkyl which is optionally interrupted by from 1 to 4 oxygen atoms in ether function.
• X in the formulae IIa to IIc either takes the meaning of two hydrogen atoms, two cyano groups in the 2,3- or 6,7-arrangement or two identical CH(R 9 )(R 10 ) groups in the 2,3- or 6,7-arrangement of the anthraquinone structure.
• the latter two CH(R 9 )(R 10 ) groups are either two CH(COOR) 2 , CH(CN)COOR or CH(CN) 2 groups, where the R radicals are preferably C 1 -C 15 -alkyl which is optionally interrupted by from 1 to 4 oxygen atoms in ether function, or C 6 -C 10 -aryl which is optionally substituted by one or more C 1 -C 15 -alkyl which is optionally interrupted by from 1 to 4 oxygen atoms in ether function.
• the variables R, R 1 and R 2 are preferably selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, 2-methylpentyl, heptyl, hept-3-yl, octyl, 2-ethylhexyl, isooctyl, nonyl, isononyl, decyl, isodecyl, undecyl, dodecyl, tridecyl, 3,5,5,7-tetramethylnonyl, isotridecyl, tetradecyl, pentadecyl,
• variables R, R 1 and R 2 are preferably selected from the group consisting of unsubstituted phenyl, the 2-, 3- and 4-monosubstituted, 2,3-, 2,4- and 3,4-disubstituted and the 2,3,4-, 2,3,5-, 2,3,6-, 2,4,5-, 2,4,6- and 3,4,5-trisubstituted phenyl radicals which are substituted by the C 1 -C 15 -alkyl radicals which are optionally interrupted by oxygen in ether function and are listed above by way of example.
• Anthraquinone derivatives of the formula III to be used in accordance with the invention are in particular the compounds of the formulae IIIa to IIId shown below: where
• R in the formulae IIIa to IIId is more preferably C 1 -C 15 -alkyl which is optionally interrupted by from 1 to 4 oxygen atoms in ether function, or C 6 -C 10 -aryl which is optionally interrupted by one or more C 1 -C 15 -alkyl which is optionally interrupted by from 1 to 4 oxygen atoms in ether function.
• R in the formulae IIIa to IIId is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, 2-methylpentyl, heptyl, hept-3-yl, octyl, 2-ethylhexyl, isooctyl, nonyl, isononyl, decyl, isodecyl, undecyl, dodecyl, tridecyl, 3,5,5,7-tetramethylnonyl, isotridecyl ,tetradecyl, pentadecyl, methoxymethyl, 2-ethylhexoxymethyl, 2-methoxyethyl, 2-ethoxyethyl, 2-
• the carrier oils used are typically viscous, high-boiling and in particular thermally stable liquids. They cover the hot metal surfaces, for example the intake valves, with a thin liquid film and thus prevent or delay the formation and deposition of decomposition products on the metal surfaces.
• base oils especially those of the Solvent Neutral (SN) 500 to 2000 viscosity class
• synthetic carrier oils based on olefin polymers having M N from 400 to 1800, in particular based on polybutene or polyisobutene (hydrogenated or nonhydrogenated), on poly-alpha-olefins or poly(internal olefins) and also synthetic carrier oils based on alk
• adducts, to be used as carrier oils, of ethylene oxide, propylene oxide and/or butylene oxide to polybutyl alcohols or polyisobutene alcohols are described for instance, in EP 277 345 A1; further polyalkene alcohol polyalkoxylates to be used in accordance with the invention are described in WO 00/50543 A1.
• Further carrier oils to be used in accordance with the invention also include polyalkene alcohol polyether amines, as detailed in WO 00/61708.
• Carburetors and intake systems of internal combustion engines, but also injection systems for fuel metering, are being contaminated to an increasing degree by impurities which are caused, for example, by dust particles from the air and uncombusted hydrocarbons from the combustion chamber.
• additives are added to the fuel to keep valves and carburetors or injection systems clean.
• Such detergents are generally used in combination with one or more carrier oils.
• the carrier oils exert an additional “wash function”, support and often promote the detergents in their action of cleaning and keeping clean, and can thus contribute to the reduction in the amount of detergents required.
• Customary detergents which find use in the inventive packages are listed, for example, in WO 00/50543 A1 and WO 00/61708 A1 and include:
• detergents and/or valve seat wear-inhibiting additives to be used in accordance with the invention are listed, for example, in WO 00/47698 A1 and include compounds which have at least one hydrophobic hydrocarbon radical having a number-average molecular weight (M N ) of from 85 to 20 000 and at least one polar moiety, and which are selected from:
• Such additives based on highly reactive polyisobutene which can be prepared from the polyisobutene (which may contain up to 20% by weight of n-butene units) by hydroformylation and reductive amination with ammonia, monoamines or polyamines, such as dimethylaminopropylamine, ethylenediamine, diethylenetriamine, triethylenetetramine or tetraethylenepentamine, are disclosed in particular in EP 244 616 A2.
• additives containing monoamino groups (i) are the compounds obtainable from polyisobutene epoxides by reaction with amines and subsequent dehydration and reduction of the amino alcohols, as described in particular in DE 196 20 262 A1.
• Additives containing nitro groups (ii), optionally in combination with hydroxyl groups, are preferably reaction products of polyisobutenes 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 96/03367 A1 and
• reaction products are generally mixtures of pure nitropolyisobutanes (e.g. ⁇ , ⁇ -dinitropolyisobutane) and mixed hydroxynitropolyisobutanes (e.g. ⁇ -nitro- ⁇ -hydroxypolyisobutane).
• Additives containing carboxyl groups or their alkali metal or alkaline earth metal salts are preferably copolymers of C 2 -C 40 -olefins with maleic anhydride which have a total molar mass of from 500 to 20 000 and of whose carboxyl groups some or all have been converted to the alkali metal or alkaline earth metal salts and any remainder of the carboxyl groups has been reacted with alcohols or amines.
• Such additives are disclosed in particular by EP 307 815 Al.
• Such additives serve mainly to prevent valve seat wear and can, as described in WO 87/01126 A1, advantageously be used in combination with customary detergents such as poly(iso)butenamines or polyetheramines.
• Additives containing sulfonic acid groups or their alkali metal or alkaline earth metal salts (v) are preferably alkali metal or alkaline earth metal salts of an alkyl sulfosuccinate, as described in particular in EP 639 632 A1.
• Such additives serve mainly to prevent valve seat wear and can be used advantageously in combination with customary detergents such as poly(iso)butenamines or polyetheramines.
• Additives containing polyoxy-C 2 -C 4 -alkylene moieties are preferably polyethers or polyetheramines which are obtainable by reaction of C 2 - to C 60 -alkanols, C 6 - to C 30 -alkanediols, mono- or di-C 2 -C 30 -alkylamines, C 1 -C 30 -alkylcyclohexanols or C 1 -C 30 -alkylphenols 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 the polyetheramines, by subsequent reductive amination with ammonia, monoamines or polyamines.
• Such products are described in particular in EP 310 875 A1, EP 356 725 A1, EP 700 985 A1 and U.S. Pat. No. 4, 877,416.
• polyethers such products also have carrier oil properties. Typical examples of these are tridecanol butoxylates, isotridecanol butoxylates, isononylphenol butoxylates and polyisobutenol butoxylates and propoxylates and also the corresponding reaction products with ammonia.
• Additives containing carboxylic ester groups (vii) are preferably esters of mono-, di- or tricarboxylic 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 38 38 918 A1.
• the mono-, di- or tricarboxylic acids used may be aliphatic or aromatic acids, and particularly suitable ester alcohols or ester polyols are long-chain representatives having, for example, from 6 to 24 carbon atoms.
• esters are adipates, phthalates, isophthalates, terephthalates and trimellitates of isooctanol, of isononanol, of isodecanol and of isotridecanol.
• Such products also have carrier oil properties.
• Particular interest attaches to derivatives with aliphatic polyamines such as ethylenediamine, diethylenetriamine, triethylenetetramine or tetraethylenepentamine.
• Such gasoline fuel additives are described in particular in U.S. Pat. No. 4, 849, 572.
• Additives containing moieties obtained by Mannich reaction of phenolic hydroxyl groups 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 dimethylaminopropylamine.
• Such “polyisobutene-Mannich bases” are described in particular in EP 831 141 A1.
• Dispersants as component c) are, for example, imides, amides, esters and ammonium and alkali metal salts of polyisobutenesuccinic anhydrides. These compounds find use especially in lubricant oils, but sometimes also as detergents in fuel compositions.
• the concentration of component a), i.e. the at least one anthraquinone derivative, in the inventive packages is typically selected in such a magnitude that, after addition of the package to the mineral oil, the desired concentration of marker(s) is present therein.
• Typical concentrations of the markers in the mineral oil are, for instance, in the range from 0.01 up to a few 10s of ppm by weight.
• Component b i.e. the at least one carrier oil
• Component b is present in the inventive packages typically in a concentration of from 1 to 50% by weight, in particular from 5 to 30% by weight, and
• the sum of their concentrations typically does not exceed 10% by weight, based on the total weight of the package (i.e. the total amount of components a) to c) and d)), the concentration of the corrosion inhibitors and demulsifiers being typically in the range of from in each case about 0.01 to 0.5% by weight of the total amount of the package.
• component d When, as component d), further markers other than anthraquinone derivatives are present in the inventive packages, their concentration is in turn based on the content that they are to have after addition of the packages in mineral oil. That which was stated for component a) applies mutatis mutandis.
• dyes are present in the inventive packages, their concentration is typically, for instance, between 0.1 to 5% by weight, based on the total amount of the package.
• the compounds 1 to 9 were synthesized starting from 1,4,5,8-tetrachloroanthraquinone and the appropriately substituted anilines by the method described in the document EP 0 323 184 A1.
• the trisubstituted compound was obtained as a by-product in the preparation of compound 8.
• the comparative compound used was the phthalocyanine of the following formula:
• test mixture used of a fuel and lubricant additive concentrate with the components contained therein and their particular proportions, is detailed below in Table 1: TABLE 1 Component Chemical composition % by weight Commercial Polyisobutenamine (PIBA); solution 70 detergent with PIBA content of 50% by weight Commercial Fatty alcohol propoxylate 15 carrier oil Commercial Dimerized and oligomerized fatty 0.1 corrosion acids protection Commercial Fatty alcohol ethoxylate 0.1 demulsifier Solvent Xylene 14.8
• the samples were transferred to 10 ml ampules, sealed in an airtight manner and stored in a water bath at 50° C.
• the comparative compound In the presence of carrier oil, the comparative compound exhibited a distinctly sharper decrease in the normalized extinction as a function of time than in the case of the presence of detergent. The values were therefore not reproduced.

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• Chemical Kinetics & Catalysis (AREA)
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• Organic Chemistry (AREA)
• Engineering & Computer Science (AREA)
• Health & Medical Sciences (AREA)
• Emergency Medicine (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Lubricants (AREA)

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• 2003
  • 2003-12-23 DE DE10361504A patent/DE10361504A1/de not_active Withdrawn
• 2004
  • 2004-12-22 JP JP2006546049A patent/JP2007515532A/ja active Pending
  • 2004-12-22 US US10/584,201 patent/US20070149415A1/en not_active Abandoned
  • 2004-12-22 AU AU2004309053A patent/AU2004309053B2/en not_active Ceased
  • 2004-12-22 KR KR1020067014028A patent/KR20060126710A/ko not_active Application Discontinuation
  • 2004-12-22 MY MYPI20045303A patent/MY143699A/en unknown
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  • 2004-12-22 CN CNA200480038844XA patent/CN1898365A/zh active Pending
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  • 2004-12-22 CA CA002549647A patent/CA2549647A1/en not_active Abandoned
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  • 2004-12-22 AR ARP040104860A patent/AR048665A1/es unknown
  • 2004-12-22 EP EP04804183A patent/EP1699907A1/de not_active Withdrawn
  • 2004-12-23 TW TW093140303A patent/TW200535234A/zh unknown
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