WO1995000606A1 - Verwendung von aminotriarylmethanen zum markieren von kohlenwasserstoffen sowie neue aminotriarylmethane - Google Patents
Verwendung von aminotriarylmethanen zum markieren von kohlenwasserstoffen sowie neue aminotriarylmethane Download PDFInfo
- Publication number
- WO1995000606A1 WO1995000606A1 PCT/EP1994/001941 EP9401941W WO9500606A1 WO 1995000606 A1 WO1995000606 A1 WO 1995000606A1 EP 9401941 W EP9401941 W EP 9401941W WO 9500606 A1 WO9500606 A1 WO 9500606A1
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- Prior art keywords
- alkyl
- optionally substituted
- independently
- hydrogen
- another
- Prior art date
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- UIWORXHEVNIOJG-UHFFFAOYSA-N CC1CCC(C)(C)CC1 Chemical compound CC1CCC(C)(C)CC1 UIWORXHEVNIOJG-UHFFFAOYSA-N 0.000 description 1
Classifications
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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
- C10L1/003—Marking, e.g. coloration by addition of pigments
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/49—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton
- C07C211/50—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton with at least two amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/08—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
- C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
- C07C217/84—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
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- 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
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/10—Amino derivatives of triarylmethanes
- C09B11/12—Amino derivatives of triarylmethanes without any OH group bound to an aryl nucleus
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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
- 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
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- 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
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- 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
-
- 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
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- 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
- C10N2040/30—Refrigerators lubricants or compressors lubricants
-
- 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
- C10N2040/32—Wires, ropes or cables lubricants
-
- 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
- C10N2040/34—Lubricating-sealants
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- 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
- C10N2040/36—Release agents or mold release agents
-
- 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
- C10N2040/38—Conveyors or chain belts
-
- 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
- C10N2040/40—Generators or electric motors in oil or gas winning field
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- 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
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- 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
- C10N2040/44—Super vacuum or supercritical use
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- 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
- C10N2040/50—Medical uses
Definitions
- the present invention relates to the use of aminotryl methanes of the formula I.
- R 1 and R 2 are the same or different and, independently of one another, each C ⁇ -Ci 3 alkyl, which can be interrupted by 1 to 3 oxygen atoms in ether function and is optionally substituted by amino or hydroxy, optionally substituted Phenyl or R 1 and R 2 together with the nitrogen atom connecting them a 5- or 6-membered saturated heterocyclic radical, which may have a further hetero atom, or R 1 also hydrogen,
- R 3 and R 4 are identical or different and independently of each voneinan ⁇ C ⁇ -C2o-alkyl tome by 1 to 4 Sauerstoffa ⁇ may be interrupted in ether function and, where appropriate, by amino, hydroxy or phenyl, or R 3 also hydrogen and
- X 1 and X 2 are the same or different and, independently of one another, each -C 1 -C 3 -alkyl, which can be interrupted by 1 to 3 oxygen atoms in ether function and is optionally substituted by amino or hydroxyl, a radical of the formula NR X R 2 , wherein R 1 and R 2 each have the above have meaning, or one of the two radicals X 1 and X 2 also denote hydrogen,
- the object of the present invention was to provide new marking agents for hydrocarbons.
- the new marking agents should be easily accessible and readily soluble in hydrocarbons. In addition, they should be easy to prove. Even very small amounts of markers should be made visible by a strong color reaction.
- aminotriarylmethanes of the formula I described at the outset are advantageously suitable for labeling hydrocarbons.
- substituted alkyl groups occur in the above formula I, they generally have 1 or 2 substituents.
- phenyl groups When substituted phenyl groups occur in the above formula I, e.g. Ci-C-j-alkyl or -C-alkoxy come into consideration.
- the phenyl groups generally have 1 to 3 substituents.
- R 1 and R 2 together with the nitrogen atom connecting them represent a 5- or 6-membered saturated heterocyclic radical, which may have a further heteroatom, for example pyrrolidinyl, piperidinyl, morpholinyl, piperazinyl or N- (C ⁇ -C Alkyl) piperazinyl come into consideration.
- R 1 , R 2 , R 3 , R 4 , X 1 and X 2 are, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, 2-methylpentyl, heptyl, octyl, 2-ethylhexyl, isooctyl, nonyl, isononyl, decyl, isodecyl,
- Undecyl, dodecyl, tridecyl, 3,5,5,7-tetramethylnonyl, isotridecyl (the above terms isooctyl, isononyl, isodecyl and iso- tridecyl are trivial names and come from the alcohols obtained after oxo synthesis - cf.
- R 3 and R 4 are furthermore, for example, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, benzyl, 1- or 2-phenylethyl, 3, 6, 9-trioxadodecyl, 3, 6, 9,12- Tetraoxatridecyl or 3,6,9,12-tetraoxatetradecyl.
- Aminotriarylmethanes of the formula I in which R 1 and R 2 independently of one another are each -C 1 -C 4 -alkyl or optionally substituted phenyl or R 1 are also hydrogen are preferably used for labeling hydrocarbons.
- aminotriarylmethanes of the formula I in which R 3 and R 4 independently of one another are each C 6 -C 3 alkyl, in particular C 6 -C 3 alkyl, which can be interrupted by 1 or 2 oxygen atoms in ether function , or R 3 also mean hydrogen, used for marking hydrocarbons.
- aminotriarylmethanes of the formula I in which X 1 and X 2 independently of one another are each C 1 -C 4 -alkyl, C 1 -C 4 -dialkylamino or one of the two radicals X 1 and X 2 also mean hydrogen for marking hydrocarbons used.
- the present invention further provides hydrocarbons containing one or more of the aminotriaryl methanes of the formula I. Preference is given to hydrocarbons containing one or more of the aminotriarylmethanes of the formula I in which R 1 and R 2 independently of one another are each C 1 -C 4 -alkyl or optionally substituted phenyl or R 1 are also hydrogen.
- Hydrocarbons in the sense of the invention are understood to mean aliphatic or aromatic hydrocarbons which are present in the liquid state under normal conditions.
- These are in particular mineral oils, for example fuels such as gasoline, kerosene or diesel oil, or oils such as heating oil or engine oil.
- the aminotriarylmethanes of formula I are particularly suitable for marking mineral oils for which marking is required, e.g. for tax reasons. In order to keep the costs of the marking low, the aim is to use the smallest possible amount of marking agent for the marking.
- aminotriaryl methanes of the formula I are used either in bulk or in the form of solutions.
- Organic solvents are suitable as solvents.
- Aromatic hydrocarbons such as toluene, xylene, dodecylbenzene, diisopropylnaphthalene or a mixture of higher aromatics, which is commercially available under the name Shellsol® AB (Shell), are preferably used.
- a concentration of aminotriarylmethane I of 20 to 80% by weight, based on the solution, is generally chosen.
- aminotriarylmethanes of the formula I to be used according to the invention it is very easy to detect marked hydrocarbons, even if the marking agents are only present in a concentration of approximately 10 ppm or less.
- the detection of the aminotriaryl methanes of the formula I used as marking agents in hydrocarbons is advantageously achieved if the mineral oil is treated with an aqueous alcoholic medium which contains a protonic acid and optionally a halide of the metals zinc, aluminum or tin.
- Suitable alcohols are e.g. Ethanol, propanol or 1-methoxypropan-2-ol. The use of ethanol is preferred.
- Suitable protonic acids for the process according to the invention are in particular so-called strong acids, i.e. Protonic acids whose pKa is ⁇ 3.5.
- strong acids i.e. Protonic acids whose pKa is ⁇ 3.5.
- examples of such acids are inorganic or organic acids, such as perchloric acid, hydroiodic acid, hydrochloric acid, hydrobromic acid, hydrofluoric acid, sulfuric acid, nitric acid, phosphoric acid, benzenesulfonic acid, naphthalenesulfonic acid, methanesulfonic acid, oxalic acid, maleic acid, chloroacetic acid, dichloroacetic acid, dichloroacetic acid or bromoacetic acid. In some cases it may be advantageous to use these acids e.g. by adding acetic acid.
- inorganic acids with hydrochloric acid or sulfuric acid being of particular importance.
- Suitable halides of the metals zinc, aluminum or tin are e.g. Zinc chloride, zinc bromide, aluminum chloride, aluminum bromide or tin tetrachloride.
- Zinc chloride is particularly noteworthy.
- the concentration of the protonic acid in the aqueous-alcoholic solution is generally 5 to 50% by weight, preferably 10 to 30% by weight.
- the concentration of metal halide is generally generally at 10 to 20 wt .-% and those of alcohol in general at 10 to 40 wt .-%.
- Preferred is a method for the detection of aminotriarylmethanes of the formula 1, -R 1 and R 2 independently of one another in each case C 1 -C 4 -alkyl or optionally substituted phenyl or R 1 is also hydrogen.
- R 3 and R 4 independently of one another are each C 6 -C 3 alkyl, which can be interrupted by 1 or 2 oxygen atoms in ether function, or R 3 also mean hydrogen.
- X 1 and X 2 independently of one another are each C 1 -C 4 -alkyl, C 1 -C 4 dialkylamino or one of the two radicals X 1 and X 2 also mean hydrogen.
- the present invention further provides amino triaryl methanes of the formula Ia
- R 1 and R 2 are identical or different and, independently of one another, are each C 1 -C 3 -alkyl which can be interrupted by 1 to 3 oxygen atoms in ether function and is optionally substituted by amino or hydroxyl, optionally substituted Phenyl or R 1 and R 2 together with the nitrogen atom connecting them a 5- or 6-membered saturated heterocyclic radical, the one may have further heteroatoms, or R 1 may also be hydrogen,
- Y 1 and Y 2 are identical or different and independently of each C ⁇ ⁇ C 2 o alkyl which tome by 1 to 4 Sauerstoffa ⁇ from each other is interrupted in ether function and is optionally substituted by amino, hydroxy or phenyl, or R 3 also Hydrogen and
- X 1 and X 2 are the same or different and, independently of one another, are each C 1 -C 3 -alkyl, which can be interrupted by 1 to 3 oxygen atoms in ether function and optionally substituted by amino or hydroxyl, a radical of the formula NR 1 R 2 , in which R 1 and R 2 each have the meaning given above, or one of the two radicals X 1 and X 2 also denotes hydrogen.
- Aminotriarylmethanes of the formula Ia are preferred, in which R 1 and R 2 independently of one another are each C 1 -C 4 -alkyl or optionally substituted phenyl or R 1 is also hydrogen.
- aminotriarylmethanes of the formula Ia in which Y 1 and Y 2 independently of one another are each C 6 -C 3 alkyl which is interrupted by 1 or 2 oxygen atoms in ether function, or R 3 is also hydrogen.
- aminotriarylmethanes of the formula Ia in which X 1 and X 2 independently of one another are each C 1 -C 4 -alkyl, C 1 -C 4 -dialkylamino or one of the two radicals X 1 and X 2 are also hydrogen.
- the new aminotriarylmethanes of the formula Ia can be prepared by methods known per se, such as those mentioned in EP-A-433 813, be preserved.
- R 3 , R 4 , Y 1 and Y 2 each have the abovementioned meaning, implement.
- the new aminotriarylmethanes of the formula Ia have good solubility in organic solvents and, as already stated above, are advantageously suitable for labeling hydrocarbons.
- the addition of the marking agent is 10 ppm.
- 20 ml of marked diesel fuel are adjusted to 2 with 20 ml of reagent solution (10% by weight zinc chloride solution in a water / ethanol mixture (60:40 v / v), pH value by adding 85% by weight acetic acid) shaken vigorously.
- the lower, aqueous phase is clearly recognizable.
- the aqueous phase can be measured photometrically against a solution of known concentration.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA002162252A CA2162252A1 (en) | 1993-06-21 | 1994-06-15 | Use of aminotriarylmethanes for marking hydrocarbons, and new aminotriarylmethanes |
EP94918872A EP0714429A1 (de) | 1993-06-21 | 1994-06-15 | Verwendung von aminotriarylmethanen zum markieren von kohlenwasserstoffen sowie neue aminotriarylmethane |
JP7502408A JPH08511551A (ja) | 1993-06-21 | 1994-06-15 | 炭化水素を標識するためのアミノトリアリールメタンの使用並びに新規のアミノトリアリールメタン |
US08/549,763 US5990327A (en) | 1993-06-21 | 1994-06-15 | Use of aminotriarylmethanes for marking hydrocarbons and novel aminotriarylmethanes |
NO955201A NO955201D0 (no) | 1993-06-21 | 1995-12-20 | Anvendelse av aminotriarylmetaner for markering av hydrokarboner, samt nye aminotriarylmetaner |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4320456A DE4320456A1 (de) | 1993-06-21 | 1993-06-21 | Verwendung von Aminotriarylmethanen zum Markieren von Kohlenwasserstoffen sowie neue Aminotriarylmethane |
DEP4320456.2 | 1993-06-21 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1995000606A1 true WO1995000606A1 (de) | 1995-01-05 |
Family
ID=6490779
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1994/001941 WO1995000606A1 (de) | 1993-06-21 | 1994-06-15 | Verwendung von aminotriarylmethanen zum markieren von kohlenwasserstoffen sowie neue aminotriarylmethane |
Country Status (7)
Country | Link |
---|---|
US (1) | US5990327A (de) |
EP (1) | EP0714429A1 (de) |
JP (1) | JPH08511551A (de) |
CA (1) | CA2162252A1 (de) |
DE (1) | DE4320456A1 (de) |
NO (1) | NO955201D0 (de) |
WO (1) | WO1995000606A1 (de) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7117187B2 (en) | 1996-11-04 | 2006-10-03 | Johnson & Johnson Pharmaceutical Reseach & Develpment, L.L.C. | Method, system and computer program product for non-linear mapping of multi-dimensional data |
WO2022161960A1 (en) | 2021-01-29 | 2022-08-04 | Basf Se | A method of marking fuels |
WO2022223384A1 (en) | 2021-04-20 | 2022-10-27 | Basf Se | A method of detecting one or more markers in a petroleum fuel using a photoacoustic detector |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7544216B2 (en) * | 2007-02-09 | 2009-06-09 | Milliken & Company | Unsubstituted and polymeric lactone colorants for coloring consumer products |
TWI516468B (zh) * | 2012-07-06 | 2016-01-11 | 羅門哈斯公司 | 三苯甲基化之烷基芳基醚 |
FR3104607B1 (fr) * | 2019-12-17 | 2022-10-21 | Total Sa | Marquage de composition |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB357179A (en) * | 1930-06-17 | 1931-09-17 | Patent Fuels & Color Corp | Improvements in the art of colouring gasoline or other petroleum distillates |
DE2333358B1 (de) * | 1973-06-30 | 1974-04-25 | Basf Ag | Farbstoffloesungen zum Faerben von Mineraloelprodukten |
DE3835489A1 (de) * | 1988-05-06 | 1990-04-19 | Alfred Dr Rer Nat Flath | Verwendung von additivmischungen als mittel zur erhoehung der verdampfungs- und verbrennungsgeschwindigkeit sowie der verbrennungsstabilitaet von in raketenbrennkammern oder hochleistungsbrennanlagen eingeduesten fluessigen treib- und brennstoffen |
EP0433813A2 (de) * | 1989-12-21 | 1991-06-26 | Bayer Ag | Triarylmethan-Farbbildner |
EP0438734A1 (de) * | 1990-01-22 | 1991-07-31 | BASF Aktiengesellschaft | Markierte Mineralöle sowie Verfahren zum Markieren von Mineralölen mittels basischer Farbstoffe |
US5207939A (en) * | 1990-08-23 | 1993-05-04 | Mobil Oil Corporation | Dihydrocarbyl substituted phenylenediamine-derived phenolic products as antioxidants |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5233048A (en) * | 1989-12-21 | 1993-08-03 | Bayer Aktiengesellschaft | Triarylmethane color formers |
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1993
- 1993-06-21 DE DE4320456A patent/DE4320456A1/de not_active Withdrawn
-
1994
- 1994-06-15 US US08/549,763 patent/US5990327A/en not_active Expired - Fee Related
- 1994-06-15 CA CA002162252A patent/CA2162252A1/en not_active Abandoned
- 1994-06-15 EP EP94918872A patent/EP0714429A1/de not_active Withdrawn
- 1994-06-15 WO PCT/EP1994/001941 patent/WO1995000606A1/de not_active Application Discontinuation
- 1994-06-15 JP JP7502408A patent/JPH08511551A/ja active Pending
-
1995
- 1995-12-20 NO NO955201A patent/NO955201D0/no not_active Application Discontinuation
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB357179A (en) * | 1930-06-17 | 1931-09-17 | Patent Fuels & Color Corp | Improvements in the art of colouring gasoline or other petroleum distillates |
DE2333358B1 (de) * | 1973-06-30 | 1974-04-25 | Basf Ag | Farbstoffloesungen zum Faerben von Mineraloelprodukten |
DE3835489A1 (de) * | 1988-05-06 | 1990-04-19 | Alfred Dr Rer Nat Flath | Verwendung von additivmischungen als mittel zur erhoehung der verdampfungs- und verbrennungsgeschwindigkeit sowie der verbrennungsstabilitaet von in raketenbrennkammern oder hochleistungsbrennanlagen eingeduesten fluessigen treib- und brennstoffen |
EP0433813A2 (de) * | 1989-12-21 | 1991-06-26 | Bayer Ag | Triarylmethan-Farbbildner |
EP0438734A1 (de) * | 1990-01-22 | 1991-07-31 | BASF Aktiengesellschaft | Markierte Mineralöle sowie Verfahren zum Markieren von Mineralölen mittels basischer Farbstoffe |
US5207939A (en) * | 1990-08-23 | 1993-05-04 | Mobil Oil Corporation | Dihydrocarbyl substituted phenylenediamine-derived phenolic products as antioxidants |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7117187B2 (en) | 1996-11-04 | 2006-10-03 | Johnson & Johnson Pharmaceutical Reseach & Develpment, L.L.C. | Method, system and computer program product for non-linear mapping of multi-dimensional data |
WO2022161960A1 (en) | 2021-01-29 | 2022-08-04 | Basf Se | A method of marking fuels |
WO2022223384A1 (en) | 2021-04-20 | 2022-10-27 | Basf Se | A method of detecting one or more markers in a petroleum fuel using a photoacoustic detector |
Also Published As
Publication number | Publication date |
---|---|
NO955201L (no) | 1995-12-20 |
EP0714429A1 (de) | 1996-06-05 |
DE4320456A1 (de) | 1994-12-22 |
NO955201D0 (no) | 1995-12-20 |
JPH08511551A (ja) | 1996-12-03 |
CA2162252A1 (en) | 1995-01-05 |
US5990327A (en) | 1999-11-23 |
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