EP2007857A1 - Utilisation de rylènes comme marqueurs de liquides - Google Patents

Utilisation de rylènes comme marqueurs de liquides

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Publication number
EP2007857A1
EP2007857A1 EP07712294A EP07712294A EP2007857A1 EP 2007857 A1 EP2007857 A1 EP 2007857A1 EP 07712294 A EP07712294 A EP 07712294A EP 07712294 A EP07712294 A EP 07712294A EP 2007857 A1 EP2007857 A1 EP 2007857A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
alkoxy
substituted
aryl
interrupted
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP07712294A
Other languages
German (de)
English (en)
Inventor
Thomas Gessner
Sophia Ebert
Ruediger Sens
Martin Koenemann
Wolfgang Ahlers
Christos Vamvakaris
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Priority to EP07712294A priority Critical patent/EP2007857A1/fr
Publication of EP2007857A1 publication Critical patent/EP2007857A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • 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
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/06—Peri-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
    • C09B5/62—Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series
    • 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
    • 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

Definitions

  • the invention relates to the use of rylene compounds as markers for liquids, in particular of oils, such as mineral oils, liquids containing such rylene compounds, as well as a method for labeling liquids and for detecting labeled liquids.
  • liquid product streams in large-scale facilities such as oil refineries, mark and track it.
  • heating oil which is usually favored for tax purposes, can be differentiated from generally higher-taxed diesel oil.
  • markers are used which either absorb outside the visible region of the spectrum and / or emit radiation or which can still be detected in small quantities, without being due to their intrinsic color in the visible region of the image Spectral- to change the visual impression of the marked compared to the unlabeled liquid.
  • markers are to be detected directly by a spectroscopic method in the labeled mineral oil, markers can be used advantageously whose absorption and / or fluorescence in the wavelength range above about 600 nm, since mineral oils usually because of their Aromatengehalts- below this Wavelength itself have high absorption and / or fluorescence.
  • WO 94/02570 describes a process for labeling hydrocarbons or mineral oils with markers which absorb or fluoresce in the infrared region of the spectrum and can be detected thereby.
  • the object of the invention is thus to provide further compounds for use as markers for liquids, in particular for mineral oils, which avoid the known disadvantages of the prior art at least in some areas and favorable application properties, such as good solubility in the liquids and good detectability even in the smallest Quantities in the appropriately labeled liquids.
  • the invention therefore provides the use of rylene derivatives of the formula (I) as markers for liquids,
  • Ci-C 2 -alkyl, C 3 -C 2 o-Alken-2-yl or C 3 -C 2 o-alkyne-2-yl, whose alkyl chain in each case by one or more -O-, -S-, -NR 1 -, -CO- and / or -SO 2 - may be interrupted and by Cyan, C r C 6 alkoxy, -COOR 2 , -CONR 2 R 3 , aryl, by C r Ci ⁇ -alkyl or C 1 -C 6 -alkoxy may be substituted, and / or a 5- to 7-membered heterocyclic radical which is bonded via a nitrogen atom and which contains further heteroatoms and may be aromatic, may be monosubstituted or polysubstituted; or
  • Aryloxy, arylthio, hetaryloxy or hetarylthio, to which in each case further saturated or unsaturated 5- to 7-membered rings whose carbon skeleton is represented by one or more groups -O-, -S-, -NR 1 -, -N CR 1 -, -CO-, -SO- and / or -SO 2 - may be fused, the entire ring system being mono- or polysubstituted by the alkyl radicals (1), cycloalkyl radicals (2), aryl or hetaryl radicals ( 3) and / or the radicals (i) and / or (iv) mentioned therein may be substituted; or a 5 to 9-membered ring attached via a nitrogen atom, whose carbon chain may be interrupted by one or more moieties -O-, -S-, -NR 1 -, -CO- and / or -SO 2 -, to the one or two unsatur
  • C 1 -C 30 -alkyl whose carbon chain may be interrupted by one or more groups -O-, -S-, -NR 1 -, -CO- and / or -SO 2 - and which may be interrupted by cyano, hydroxy, nitro, C r C 6 alkoxy, -COOR 2, -CONR 2 R 3, aryl substituted by C r Ci ⁇ alkyl or C r C 6 - may be substituted alkoxy, and / or bonded via a nitrogen atom, 5- to 7- membered heterocyclic radical containing further heteroatoms and may be aromatic, mono- or polysubstituted;
  • Aryl or hetaryl each represented by Ci-Ci 8 alkyl, dC 6 alkoxy, cyano, nitro, halogen, - CONR 2 R 3 , -NR 2 COR 3 , -SO 2 NR 2 R 3 and / or aryl or Hetarylazo, which may be substituted by Ci-Cio-alkyl, Ci-C 6 -alkoxy or cyano, may be mono- or polysubstituted, or C r Ci 2 alkoxy, C r Ci 2 alkylthio or NR 3 R 4 ;
  • R 1 is identical or different hydrogen or C 1 -C 6 -alkyl
  • R 2 , R 3 , R 4 are the same or different hydrogen
  • C 1 -C 8 -alkyl whose carbon chain may be interrupted by one or more groups -O-, -S-, -CO-, -SO- and / or -SO 2 - and which is mono- or polysubstituted by d-Ci 2 Alkoxy, C 1 -C 6 -alkylthio, hydroxy, mercapto, halogen, cyano, nitro and / or - COOR 1 ;
  • Aryl or hetaryl to which in each case further saturated or unsaturated 5- to 7-membered rings, whose carbon skeleton may be interrupted by one or more groups -O-, -S-, -CO- and / or -SO 2 - be fused can, wherein the entire ring system may be mono- or polysubstituted by d-Ci 2 alkyl and / or the above, as substituents for alkyl radicals may be substituted; and R is the same or different hydrogen,
  • Sulfomethyl 2-sulfoethyl, 3-sulfopropyl, 4-sulfobutyl, 5-sulfopentyl, 6-sulfohexyl, 8-sulfooctyl, 10-sulfodecyl, 12-sulfododecyl and 14-sulfotetradecyl;
  • Pentoxy isopentoxy, neopentoxy, tert. Pentoxy and hexoxy;
  • B05 / 0831 PC Carbamoyl, methylaminocarbonyl, ethylaminocarbonyl, propylaminocarbonyl, butylaminocarbonyl, pentylaminocarbonyl, hexylaminocarbonyl, heptylaminocarbonyl, octylaminocarbonyl, nonylaminocarbonyl, decylaminocarbonyl and phenylaminocarbonyl;
  • Aminosulfonyl N, N-dimethylaminosulfonyl, N, N-diethylaminosulfonyl, N, N-dipropylaminosulfonyl, N, N-diisopropylaminosulfonyl, N, N-dibutylaminosulfonyl, N, N-diisobutylaminosulfonyl, N, N-di-sec.
  • Naphthalene derivatives according to the invention preferably carry 2 substituents X.
  • Perylene derivatives according to the invention preferably carry 2 substituents X.
  • Terry derivatives according to the invention preferably carry 2 or 4 substituents X.
  • Quarterrylene derivatives according to the invention preferably carry 2, 4 or 6 substituents X.
  • the rylene derivatives (I) are generally obtained in the form of product mixtures with different degrees of substitution or as isomers, which can be separated, if desired, for example by chromatography.
  • the rylene derivatives (I) are used in the form of the mixture resulting from the synthesis.
  • n is preferably 0.1, 2 or 3.
  • X is preferably the same or different
  • CrC 2 o-alkyl, C 3 -C 2 o-alkene-2-yl or C 3 -C 2 o-alkyne-2-yl, their alkyl chain in each case by one or more groups -O-, -S-, -NR 1 -, -CO- and / or -SO 2 - may be interrupted and by Cyan, C r C 6 alkoxy, -COOR 2 , -CONR 2 R 3 , aryl, by C r Ci ⁇ -alkyl or dC 6 Alkoxy, and / or a nitrogen atom bonded 5- to 7-membered heterocyclic radical containing further heteroatoms and may be aromatic, mono- or polysubstituted;
  • Ci-C 3 -alkyl whose carbon chain by one or more -O-, -S-, -NR 1 - moieties and which may be, by cyano, hydroxy -, -CO- and / or -SO 2
  • C 5 -C 8 -cycloalkyl whose carbon skeleton may be interrupted by one or more groups - O-, -S- and / or -NR 1 - and / or which may be mono- or polysubstituted by C 1 -C 6 -alkyl;
  • Aryl or hetaryl each represented by Ci-Ci 8 alkyl, CrC 6 alkoxy, cyano, nitro, halogen, -CONR 2 R 3 , -NR 2 COR 3 , -SO 2 NR 2 R 3 and / or aryl or Hetarylazo, which may be substituted by Ci-Cio-alkyl, Ci-C 6 -alkoxy or cyano, may be mono- or polysubstituted, or C r Ci 2 -alkoxy or NR 3 R 4 .
  • R 1 is preferably hydrogen or C 1 -C 6 -alkyl.
  • R 2 , R 3 , R 4 are preferably identical or different hydrogen
  • C 1 -C 8 -alkyl which may be substituted by C 1 -C 6 -alkoxy, halogen, hydroxyl, carboxyl and / or cyano;
  • Aryl or hetaryl which may be substituted by the above radicals for alkyl as well as by CrC 6 alkyl.
  • R is preferably dC 3 o-alkyl whose carbon chain may be interrupted by one or more groups -O-, -S-, -NR 1 -, -CO- and / or -SO 2 - and which may be interrupted by cyano, CrC 6 - Alkoxy, aryl which may be substituted by C 1 -C 8 -alkyl or C 1 -C 6 -alkoxy, and / or a nitrogen-bonded 5 to 7-membered heterocyclic radical which contains further heteroatoms and may be aromatic, on or may be substituted several times; C 5 -C 8 -cycloalkyl whose carbon skeleton may be interrupted by one or more groups -O-, -S- and / or -NR 1 - and / or which may be mono- or polysubstituted by C 1 -C 6 -alkyl;
  • Aryl or hetaryl by d-Ci 8 alkyl, dC 6 alkoxy, cyano, nitro, halogen, -CONR 2 R 3, -SO 2 NR 2 R 3, -COOR 2, -SO 3 R 2 and / or Aryl or Hetarylazo, which may be substituted by Ci-Ci O alkyl, CrC 6 alkoxy or cyano, may be mono- or polysubstituted.
  • n is more preferably 0, 1, 2 or 3.
  • X is more preferably identical or different, preferably equal to, NHR 3 - phenyloxy, phenylthio, phenylamino, pyrimidyloxy, pyrimidylthio, pyrrolidinyl or piperidinyl, each unsubstituted or substituted by one or more
  • R 1 is particularly preferably hydrogen or C 1 -C 6 -alkyl.
  • R 3 is particularly preferably hydrogen, C 1 -C 8 -alkyl which may be substituted by C 1 -C 6 -alkoxy, halogen, hydroxyl, carboxyl and / or cyano; Aryl or hetaryl, which may be substituted by the above radicals mentioned for alkyl as well as by dC 6 alkyl.
  • R is particularly preferably (C 4 -C 2 O) -alkyl or phenyl which is unsubstituted or substituted by one or more (C 1 -C 10) -alkyl groups.
  • n is very particularly preferably 0, 1, 2 or 3.
  • X is very particularly preferably identical or different, preferably equal to NH ( C 1 -C 10) -alkyl, phenoxy, phenylamino, pyrrolidinyl, piperidinyl, where the radicals mentioned are unsubstituted or in each case substituted by one to three (C 1 -C 6) -alkyl groups.
  • R is very particularly preferably (C 4 -C 2 O) -alky I or phenyl which is substituted by one or more groups (C 1 -C 8 ) -alkyl.
  • n is preferably 0, 1, 2 or 3.
  • R is particularly preferred
  • Preferred compounds of the formula (I) are furthermore those of the formula (IA)
  • Particularly preferred compounds of the formula (I) are those of the formula (IAa)
  • B05 / 0831 PC X is identical or different d-C 2 alkoxy, aryloxy, optionally substituted as in formula (I) substituted as indicated or bound via a nitrogen atom 5 to 9-membered ring, optionally, (I) modified as indicated in formula;
  • R, m have the meanings given in the formula (I).
  • Preferred compounds of the formula (I) are those of the formula (ID)
  • Preferred compounds of the formula (ID) are those of the formula (IDd)
  • a further preferred group of compounds of the formula (I) are those in which at least one group X is a radical of the formula
  • R b is the same or different
  • C 1 -C 8 -alkyl whose carbon chain may be interrupted by one or more groups -O-, -S-, -CO- and / or -SO 2 - and the one or more times by d-C 2 -alkoxy , C 1 -C 6 -alkylthio, hydroxy, mercapto, halogen, cyano, nitro and / or -COOR C may be substituted;
  • Aryl or hetaryl, to which in each case further saturated or unsaturated 5- to 7-membered rings, whose carbon skeleton may be interrupted by one or more groups - O-, -S-, -CO- and / or -SO 2 - be fused can, wherein the entire ring system one or more times by d-Ci 2 alkyl
  • Cs-C ⁇ -cycloalkyl whose carbon skeleton may be interrupted by one or more moieties - O-, -S- and / or -NR 1 - and / or which may be mono- or polysubstituted by C 1 -C 6 -alkyl;
  • Aryl or hetaryl each represented by Ci-Ci 8 alkyl, CrC 6 alkoxy, cyano, nitro, halogen, -CONR 2 R 3 , -NR 2 COR 3 , -SO 2 NR 2 R 3 and / or aryl or Hetarylazo, which may be substituted by Ci-Cio-alkyl, Ci-C 6 -alkoxy or cyano, may be mono- or polysubstituted.
  • cyclic amines from which the group X is derived in particular piperidines, pyrrolidines, piperazines, morpholines and thiomorpholines (1, 4-thiazines) may be mentioned, the piperidines, pyrrolidines, piperazines and morpholines are preferred and the piperidine particularly are preferred.
  • cyclic amines can be chemically modified, ie their carbon chain can be interrupted not only by -O-, -S- or -NR 1 - but also by -CO-, -SO- or -SO 2 -, they can be an or have two aromatic or saturated 4- to 7-membered fused rings whose carbon chain may also be interrupted by the groupings mentioned, and they can by the
  • B05 / 0831 PC be substituted alkyl, cycloalkyl and / or (Het) aryl radicals. However, preferred are the unmodified groups.
  • Suitable amines are:
  • Piperidine 2- or 3-methylpiperidine, 6-ethylpiperidine, 2,6- or 3,5-dimethylpiperidine, 2,2,6,6-tetramethylpiperidine, 4-benzylpiperidine, 4-phenylpiperidine, piperidin-4-ol, piperidine pyridine-4-carboxylic acid, piperidine-4-carboxylic acid methyl ester, piperidine-4-carboxylic acid ethyl ester, piperidine-4-carboxamide, 2,2,6,6-tetramethylpiperidin-4-one, 2,2,6,6-tetramethylpiperidine 4-ylamine, decahydroquinoline and decahydroisoquinoline;
  • Piperazine diketopiperazine, 1-benzylpiperazine, 1-phenethylpiperazine, 1-cyclohexylpiperazine, 1-phenylpiperazine, 1- (2,4-dimethylphenyl) piperazine, 1- (2-, 3- or 4-methoxyphenyl) -piperazine, 1- (2-, 3- or 4-ethoxyphenyl) piperazine, 1- (2-, 3- or 4-fluorophenyl) piperazine, 1- (2-, 3- or 4-chlorophenyl) piperazine, 1- ( 2-, 3- or 4-bromophenyl) -piperazine, 1-, 2- or 3-pyridin-2-ylpiperazine and 1-benzo [1,3] dioxol-4-ylmethylpiperazine;
  • quaterrylene compounds (n 3) into consideration, in which m is 0 (ie, the Quaterrylengerüst is unsubstituted) and the radicals R independently of one another in each case C 8 -C 8 alkyl or phenyl which is substituted twice by dC 4 alkyl on the other hand, mean those in which m is from 2 to 6, X has the meaning of phenoxy, phenylthio, pyrimidyloxy or pyrimidylthio, which may be substituted by Ci-C 4 alkyl, the radicals R for Cs C ⁇ -cycloalkyl or phenyl, pyridyl or pyrimidyl, which is in each case mono- or polysubstituted by C 1 -C 4 -alkoxy, -CONHR 1 or -NHCOR 1 , and R 1 is C 1 -C 4 -alkyl or phenyl which is represented by C i -
  • -NR 1 -, -CO- and / or -SO 2 - may be interrupted and / or by hydroxy, cyano, -COOR 1 , -SO 3 R 1 or Ci-C 6 alkoxy mono- or polysubstituted can be,
  • Cyan, -COOR 1 , -SO 3 R 1 or Ci-C 6 alkoxy may be monosubstituted or polysubstituted, and R has the meanings given in the formula (I).
  • the compounds of formula (I) are partially known and partly new. The invention therefore also relates to compounds of the formula (I) from the group:
  • the present invention furthermore relates to liquids which contain at least one compound of the formula (I) as a marker.
  • Suitable liquids which can be marked with the compounds of the formula (I) are preferably oils, such as mineral oils, vegetable and animal fatty oils and essential oils.
  • oils are natural oils, such as olive oil, soybean oil or sunflower oil, or natural or synthetic engine, hydraulic or gear oils, e.g. Vehicle engine oil or sewing machine oil, or brake fluids and mineral oils, which comprise according to the invention gasoline, kerosene, diesel oil and also heating oil.
  • mineral oils such as gasoline, kerosene, diesel oil or heating oil, in particular gasoline, diesel oil or heating oil.
  • the compounds of the formula (I) to be used as markers are added to the liquids in amounts such that reliable detection is ensured.
  • the (weight-related) total content of markers in the labeled liquid is about 0.1 to 5000 ppb, preferably 1 to 2000 ppb and particularly preferably 1 to 1000 ppb.
  • the compounds are generally added in the form of solutions (stock solutions).
  • suitable solvents for preparing these stock solutions are preferably aromatic hydrocarbons, such as toluene, xylene or higher-boiling aromatic mixtures.
  • a total concentration of the markers of from 0.5 to 50% by weight, based on the total weight of these stock solutions, is generally selected.
  • the compounds of formula (I) may optionally also be mixed with other markers / dyes, e.g. have been described in the beginning, can be used.
  • the total amount of the markers in the liquids is then usually in the range described above.
  • the invention also provides a process for the labeling of liquids, preferably oils, more preferably mineral oils, wherein the liquid is a compound of formula (I) is added.
  • the detection of the compounds of formula (I) in the liquids is carried out by conventional methods. Since these compounds usually have high absorbency and / or fluorescence, in the given case, e.g. a spectroscopic detection.
  • the compounds of the formula (I) generally have their absorption maximum in the range from 600 to 1000 nm and / or fluoresce in the range from 600 to 1200 nm and can thus easily be detected with suitable instruments.
  • the detection can be carried out in a manner known per se, for example by measuring the absorption spectrum of the liquids to be examined.
  • a semiconductor laser or a semiconductor diode having a wavelength in the spectral range from ⁇ max -100 nm to ⁇ max +20 nm.
  • ⁇ max means the wavelength of the absorption maximum of the marker.
  • the wavelength of the maximum emission is in the range of 620 to 1200 nm.
  • the fluorescent light thus generated is advantageously detected with a semiconductor detector, in particular with a silicon photodiode or a germanium photodiode.
  • Detection is particularly advantageous when there is an interference filter and / or an edge filter (with a short-wave transmission edge in the range from ⁇ max to ⁇ max +80 nm) in front of the detector and / or a polarizer.
  • the invention also provides a process for the identification of liquids which contain a compound of formula (I) in an amount sufficient to induce detectable fluorescence upon irradiation with radiation of a suitable wavelength,
  • the liquid is irradiated with electromagnetic radiation having a wavelength of 600 to 1000 nm, and b) the excited fluorescence radiation is detected with a device for detecting radiation in the near infrared range.
  • the rylene derivatives of the formula (I) can also be used as a component in additive concentrates (hereinafter also referred to as "packages"), which in addition to a carrier oil and a mixture of different fuel additives also generally contain dyes and Invisible fiscal or manufacturer-specific marking, additionally contain markers.
  • packages which make it possible for various mineral oil distributors to supply themselves from a “pool” of unadditivated mineral oil and only with
  • the carrier oils used are usually viscous, high-boiling and, in particular, thermostable liquids. They coat the hot metal surfaces, e.g. the inlet valves, with a thin film of liquid and prevent or delay the formation and deposition of decomposition products on the metal surfaces.
  • mineral carrier oils in particular those of the viscosity class "Solvent Neutral (SN) 500 to 2000"
  • synthetic carrier oils can be used as component b) of the fuel and lubricant additive concentrates
  • Polyisobutene base (hydrogenated or nonhydrogenated), of polyalphaolefins or polyinteralalefins, and synthetic carrier oils based on alkoxylated long-chain alcohols or phenols.
  • Adducts of ethylene oxide, propylene oxide and / or butylene oxide with polybutyl or polyisobutene alcohols to be used as carrier oils are as described in the document
  • EP 277 345 A1 further polyalkene alcohol polyalkoxylates to be used in the document
  • WO 00/50543 A1 describes.
  • Other carrier oils to be used are also polyalkene alcohol-polyetheramines, as listed in WO 00/61708.
  • mixtures of different carrier oils can also be used provided that they are compatible with one another and with the other components of the packages.
  • Carburettors and intake systems of internal combustion engines, but also injection systems for fuel metering, are increasingly burdened by impurities caused, for example, by dust particles from the air and unburned hydrocarbon radicals from the combustion chamber.
  • detergents 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 "washing function", often support and promote the detergents in their cleansing and pure-preserving action and can thus contribute to reducing the required amount of detergents.
  • carrier oils with detergent / dispersant effect are set out, for example, in the last-mentioned WO document.
  • Polyisobuteneamines which are obtainable according to EP-A 244 616 by hydroformylation of highly reactive polyisobutene and subsequent reductive amination with ammonia, monoamines or polyamines, such as dimethyleneaminopropylamine, ethylenediamine, diethylenetriamine, triethylenetetramine or tetraethylenepentamine,
  • Poly (iso) buteneamines which are obtainable by chlorination of polybutenes or polyisobutenes having double bonds predominantly in the ⁇ and ⁇ position and subsequent amination with ammonia, monoamines or the abovementioned polyamines,
  • Polyisobuteneamines which are obtainable according to DE-A 196 20 262 from polyisobutene epoxides by reaction with amines and subsequent dehydration and reduction of the amino alcohols,
  • Hydroxyl-containing polyisobuteneamines which are obtainable according to EP-A 476 485 by reacting polyisobutene epoxides with ammonia, monoamines or the abovementioned polyamines,
  • Polyetheramines which by reaction of C 2 - to C30 -alkanols, Ce- to C30-AI- kandiols, mono- or di-C 2 - to C 30 -alkylamines, C 1 - to C 5 -alkylcyclohexa-nolen or C to C 30- Alkylphenolen with 1 to 30 mol of ethylene oxide and / or propylene oxide and / or butylene oxide per hydroxyl or amino group and subsequent reductive amination with ammonia, monoamines or the above-mentioned polyamines are available, and
  • Polyisobutene Mannich bases which are obtainable according to EP-A 831 141 by reacting polyisobutene-substituted phenols with aldehydes and monoamines or the abovementioned polyamines.
  • detergents and / or valve seat wear-inhibiting additives to be used are listed, for example, in WO 00/47698 A1 and comprise 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 group , and which are selected from:
  • hydroxyl groups in combination with mono- or polyamino groups, where at least one nitrogen atom has basic properties (iv) carboxyl groups or their alkali metal or alkaline earth metal salts, (v) sulfonic acid groups or their alkali metal or alkaline earth metal salts, (vi) polyoxy-C 2 - to C 4 -alkylene groups which are terminated by hydroxyl groups, mono- or polyamino groups, where at least one nitrogen atom has basic properties, or are terminated by carbamate groups, (vii) carboxylic acid ester groups,
  • succinic anhydride-derived moieties having hydroxy and / or amino and / or amido and / or imido groups and (ix) moieties generated by Mannich reaction of phenolic hydroxyl groups with aldehydes and mono- or polyamines.
  • Such additives based on highly reactive polyisobutene which may contain 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 can be prepared, are known in particular from document EP 244 616 A2.
  • the preparation route is afforded by chlorination and subsequent amination or by oxidation of the double bond with air or ozone to carbonyl - or carboxyl compound and subsequent amination under reductive (hydrogenating) conditions.
  • amination the same amines as described above can be used for the reductive amination of the hydroformylated highly reactive polyisobutene.
  • Corresponding additives based on polypropene are described in particular in the document WO 94/24231 A1.
  • monoamino groups (i) containing additives are the polyisobutene epoxides by reaction with amines and subsequent dehydration and reduction of the amino alcohols obtainable compounds, as described in particular in the document DE 196 20 262 A1.
  • Hydroxyl groups in combination with mono- or polyamino groups (iii) containing additives are in particular reaction products of polyisobutene epoxides available
  • Carboxyl groups or their alkali metal or alkaline earth metal salts (iv) containing additives are preferably copolymers of C 2 -C 40 olefins with maleic anhydride having a total molecular weight of 500 to 20,000, their carboxyl groups wholly or partly to the alkali metal or alkaline earth metal salts and a remaining Rest of the carboxyl groups are reacted with alcohols or amines.
  • Such additives are known in particular from document EP 307 815 A1.
  • Such additives are mainly used to prevent valve seat wear and, as described in document WO 87/01 126 A1, may advantageously be used in combination with conventional detergents, such as poly (iso) butenamines or polyetheramines.
  • Sulfonic acid groups or their alkali metal or alkaline earth metal salts (v) containing additives are preferably alkali metal or alkaline earth metal salts of a Sulfobern- steinklaklalesters, as described in particular in EP 639 632 A1.
  • Such additives serve primarily to prevent valve seat wear and can be used to advantage in combination with conventional detergents such as poly (iso) buteneamines or polyetheramines.
  • Polyoxy-C 2 - to C 4 -alkylene (vi) containing additives are preferably polyether or polyetheramines, which by reaction of C 2 - to C ⁇ o-alkanols, Ce- to C3o-alkanediols, mono- or di-C 2 -C 3 - alkylamines, C 1 -C 30 -alkylcyclohexanols or C 1 -C 30 -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 polyetheramines, by subsequent reductive amination with ammonia, Monoamines or polyamines are available.
  • Such products are described in particular in EP 310 875 A1, EP 356 725 A1, EP 700 985 A1 and US Pat. No. 4,877,416.
  • polyethers such products also meet carrier oil properties. Typical examples thereof are tridecanol or isotridecanol butoxylates, isononylphenol butoxylates and also polyisobutenol butoxylates and propoxylates and the corresponding reaction products with ammonia.
  • Carboxyl ester groups (vii) containing additives are preferably esters of mono-, di- or tricarboxylic acids with long-chain alkanols or polyols, especially those having a minimum viscosity of 2 mm 2 / s at 100 0 C, as described in particular in DE 38 38 918 A1 are described.
  • mono-, di- or tricarboxylic acids it is possible to use aliphatic or aromatic acids; as ester alcohols or polyols, especially long-chain representatives with, for example, 6 to 24 C atoms are suitable.
  • esters are adipates, phthalates, isophthalates, terephthalates and trimellitates of iso-octanol, iso-nonanol, iso-decanol and of isotridecanol. Such products also meet carrier oil properties.
  • derivatives with aliphatic polyamines such as ethylenediamine, diethylenetriamine, triethylenetetramine or tetraethylenepentamine.
  • Such Otto fuel additives are described in particular in the document US 4,849,572.
  • Mannich reaction of phenolic hydroxyl groups with aldehydes and mono- or polyamines generated groupings (ix) containing additives 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 document EP 831 141 A1.
  • Dispersants as component c) are, for example, imides, amides, esters and ammonium and alkali metal salts of polyisobutene succinic anhydrides. These compounds find particular use in lubricating oils, but in some cases also as detergents in fuel compositions.
  • additives and auxiliaries which may optionally be present as component d) of the packing are organic solvents, e.g. Alcohols, such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol, sec-butanol, pentanol, isopentanol, neopentanol or hexanol, e.g. Glycols, such as 1, 2-ethylene glycol, 1, 2 or 1, 3-propylene glycol, 1, 2, 2,3 or 1, 4-butylene glycol, di- or triethylene glycol or di- or tripropylene glycol, e.g.
  • Alcohols such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol, sec-butanol, pentanol, isopentanol, neopentanol or hexanol
  • Glycols such as 1, 2-ethylene glycol, 1,
  • Ethers such as methyl tert-butyl ether, 1,2-ethylene glycol monomethyl or dimethyl ether, 1,2-ethylene glycol mono- or diethyl ether, 3-methoxy-propanol, 3-isopropoxy-propanol, tetrahydrofuran.
  • ketones such as acetone, methyl ethyl ketone or diacetone alcohol
  • esters such as methyl acetate, ethyl acetate, propyl acetate or butyl acetate
  • lactams such as N-methylpyrrolidinone (NMP)
  • NMP N-methylpyrrolidinone
  • Corrosion inhibitors for example based on film-forming ammonium salts of organic carboxylic acids or of heterocyclic aromatics in non-ferrous metal corrosion protection,
  • Antioxidants or stabilizers for example based on amines such as p-phenylenediamine, dicyclohexylamine or derivatives thereof or of phenols such as 2,4-di-tert-butylphenol or 3,5-di-tert-butyl-4-hydroxyphenylpropionic acid, Demulsifiers, antistatic agents,
  • Metallocenes such as ferrocene or methylcyclopentadienyl manganese tricarbonyl
  • lubricity additives such as certain fatty acids, alkenylsuccinic esters, bis (hydroxyalkyl) fatty amines, hydroxyacetamides or castor oil, amines for lowering the pH of the fuel, others from the rylene derivatives of the formula (I) and their preferred embodiments, various markers and dyes.
  • the concentration of component a), i. of the at least one rylene derivative of the formula (I) or its preferred embodiments, in the packages is usually chosen in such a height that after addition of the package to the mineral oil, the desired concentration of marker (s) is contained therein.
  • Typical concentrations of the marking substances in the mineral oil are approximately in the range of 0.01 to a few 10 ppm by weight.
  • Component b) i. the at least one carrier oil is usually in the packages in a concentration of 1 to 50, in particular 5 to 30 wt .-%, and component c), i. the at least one detergent and / or the at least one dispersant, usually in a concentration of 25 to 90 wt .-%, in particular 30 to 80 wt .-%, in each case based on the total amount of components a) to c) and optionally d), wherein the sum of the individual concentrations of the components a) to c) and optionally d) to 100 wt .-% complements.
  • corrosion inhibitors as component d), corrosion inhibitors, antioxidants or stabilizers, demulsifiers, antistatic agents, metallocenes, lubricity improvers and amines for lowering the pH of the fuel are contained in the packages, their total concentration usually amounts to not more than 10% by weight. -%, based on the total amount of the package (ie the total amount of components a) to c) and d)), wherein the concentration of the corrosion inhibitors and demulsifiers usually in the range of about 0.01 to 0.5 wt .-% of Total amount of the package is.
  • organic solvents are contained in the packages, their concentration in the sum usually amounts to not more than 20 wt .-%, based on the total amount of the package.
  • these solvents are obtained from solutions of the markers and / or dyes which are added to the packages with a view to a more precise meterability instead of the pure markers and / or dyes.
  • component d further labeling substances other than rylene derivatives of the formula (I) or their preferred embodiments are contained in the packages, their concentration is again measured at the content which they should have after addition of the packages in the mineral oil. The same applies to component a).
  • dyes are present in the packages according to the invention as component d), their concentration is usually about between 0.1 to 5 wt .-%, based on the total amount of the package.
  • the crude product (8.7 g) was dissolved in 140 ml of toluene-cyclohexane mixture (4: 1) and chromatographed on silica gel (70-200 ⁇ m). After removal of the solvent, 2.52 g (25% of theory) of dark blue powder having a melting point> 350 ° C. were obtained from a fraction which was uniform according to thin-layer chromatogram.
  • the precipitate was filtered off, washed with water and dried at 75 ° C in a vacuum oven.
  • the crude product (20.24 g) was refluxed in 100 ml of pyrrolidine for 7 hours (88 ° C). After cooling to room temperature, the reaction mixture was treated with a solution of 80 ml of water and 20 ml of methanol. The precipitate was filtered off, washed with 200 ml of 20% aqueous methanol, then with 300 ml of water and dried at 75 ° C in a vacuum oven.
  • the crude product thus obtained (17.29 g) was recrystallized from 173 ml of tetrahydronaphthalene.
  • the crude product (2.81 g) was dissolved in 50 ml of n-heptane / chloroform / acetone (55: 40: 5) and purified on silica gel (70-200 ⁇ m). 1, 16 g (41% of theory) of green powder having a melting point> 350 ° C. were obtained from a fraction which was uniform according to thin-layer chromatogram after removal of the solvent.
  • Example 8 N, N'-bis (2,6-diisopropylphenyl) -1, 6,9,14-tetrakis (2,6-diisopropylphenoxy) -terrenylene-3,4,11,12-tetracarboxylic diimide
  • NMP N-methylpyrrolidone
  • Example 9 N, N'-bis (2,6-diisopropylphenyl) -1, 6,7 (8), 11, 16,17 (18) -hexy (4-tert-octylphenoxy) -quaterrylene-3,4, 13,14-tetracarboxylic diimide

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Abstract

L'invention concerne l'utilisation de dérivés de rylène de la formule générale (I) comme marqueurs de liquides. Les symboles et indices sont tels que définis dans la description.
EP07712294A 2006-03-01 2007-02-23 Utilisation de rylènes comme marqueurs de liquides Withdrawn EP2007857A1 (fr)

Priority Applications (1)

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EP07712294A EP2007857A1 (fr) 2006-03-01 2007-02-23 Utilisation de rylènes comme marqueurs de liquides

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EP06110552 2006-03-01
PCT/EP2007/051745 WO2007099059A1 (fr) 2006-03-01 2007-02-23 Utilisation de rylènes comme marqueurs de liquides
EP07712294A EP2007857A1 (fr) 2006-03-01 2007-02-23 Utilisation de rylènes comme marqueurs de liquides

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US (1) US20100011656A1 (fr)
EP (1) EP2007857A1 (fr)
JP (1) JP2009528417A (fr)
KR (1) KR20080106276A (fr)
CN (1) CN101389737A (fr)
AU (1) AU2007220528A1 (fr)
BR (1) BRPI0708384A2 (fr)
CA (1) CA2643107A1 (fr)
IL (1) IL193420A0 (fr)
NO (1) NO20083694L (fr)
NZ (1) NZ570556A (fr)
WO (1) WO2007099059A1 (fr)
ZA (1) ZA200808278B (fr)

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KR20080106276A (ko) 2008-12-04
NO20083694L (no) 2008-09-29
NZ570556A (en) 2010-05-28
ZA200808278B (en) 2009-12-30
BRPI0708384A2 (pt) 2011-05-24
JP2009528417A (ja) 2009-08-06
US20100011656A1 (en) 2010-01-21
CN101389737A (zh) 2009-03-18
AU2007220528A1 (en) 2007-09-07
IL193420A0 (en) 2009-05-04
CA2643107A1 (fr) 2007-09-07

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