WO1999055807A1 - Lubricants containing coumarin dyes - Google Patents
Lubricants containing coumarin dyes Download PDFInfo
- Publication number
- WO1999055807A1 WO1999055807A1 PCT/EP1999/002626 EP9902626W WO9955807A1 WO 1999055807 A1 WO1999055807 A1 WO 1999055807A1 EP 9902626 W EP9902626 W EP 9902626W WO 9955807 A1 WO9955807 A1 WO 9955807A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- lubricant
- coumarin dye
- coumarin
- lubricants
- dye
- Prior art date
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Classifications
-
- 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 lubricants containing coumarin dyes, a process for their preparation and their use as hydraulic oils or lubricants in
- R ⁇ and R 2 independently of one another are C ] -C -alkyl, in particular methyl and ethyl, 2 -
- R 3 to R 6 independently of one another are H, C 1 -C 4 -alkyl, in particular CH 3 and tert-butyl, halogen, in particular Cl, sulfonamide, in particular -SO 2 NH 2 and -SO 2 N (CH 3 ) 2 , C r C 4 alkylsulfonyl, in particular -SO C 2 H 5 , C -C -cycloalkyl, in particular cyclohexyl or Cg-Cio-aryl, in particular phenyl,
- R7 or CN means and
- X stands for O or S.
- Very particularly preferred coumarin dyes of the formula (I) are those which correspond to the formula (II)
- R 4 represents Cl or SO 2 NH 2 .
- Natural or refined mineral oils, synthetic hydrocarbons, alkylbenzenes, polyalphaolefins, polyalkylene glycols and polyesters are preferably used as lubricants.
- Lubricants with a viscosity of 5 to 200, in particular 10 to 100 cSt, at 40 ° C. are preferably used. It is preferred to use the coumarin dye in an amount of 0.0001 to 0.1%, preferably 0.001 to 0.03%, based on the lubricant.
- the invention further relates to a process for the preparation of the lubricants according to the invention, characterized in that a coumarin dye, if appropriate in the presence of suitable organic solvents, is introduced into the lubricant and then the optionally used organic solvent is removed from the lubricant, preferably thermally, in particular by distillation.
- a possible solvent is preferably an oil-compatible and easily distilled off solvent, in which the
- Coumarin dye is soluble at the same time.
- Aromatic hydrocarbons such as toluene or xylene can be mentioned as possible organic solvents.
- the coumarin dye is introduced into the lubricant as such or in dissolved form at a temperature of 15 ° C. to 220 ° C., in particular at -20 to 150 ° C., preferably by stirring.
- the invention further relates to the use of the lubricant containing coumarin dye as hydraulic oil, for example as a brake fluid or for incorporation in cooling fluids.
- Possible cooling liquids in this connection are, for example, fluorocarbons, chlorofluorocarbons and methane, ethane, propane, butane or pentane and their halogen and ether derivatives and their mixtures and also mixtures of fluorocarbons and chlorofluorocarbons as well as carbon dioxide and ammonia.
- the lubricant according to the invention is preferably used in hydraulic oils, in particular those made from natural or synthetic mineral oils.
- Lubricant according to the invention used in this way has the advantage that leaks in daylight or when illuminated with a lamp which emits at a wavelength between 380 and 500 nm can be identified by a greenish-yellow to orange fluorescence.
- the advantages mentioned at the beginning are to be mentioned. - 4 -
- refined mineral oil with different viscosities was colored with this dye.
- the following refined mineral oils were colored:
- Viscosity 15 cSt, measured at 40 ° C (Rando® HDZ 15 from Texaco)
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Abstract
It has been discovered that lubricants containing coumarin dyes and used especially as hydraulic oils or intended for introduction into coolants, are extremely well suited for indicating or detecting leaks in such hydraulic systems or cooling systems.
Description
1 - 1 -
Cumarinfarbstoffe enthaltende SchmiermittelLubricants containing coumarin dyes
Die Erfindung betrifft Cumarinfarbstoffe enthaltende Schmiermittel, ein Verfahren zu ihrer Herstellung sowie ihre Verwendung als Hydrauliköle oder Schmierstoffe inThe invention relates to lubricants containing coumarin dyes, a process for their preparation and their use as hydraulic oils or lubricants in
Kühlflüssigkeiten.Coolants.
Gemäß JP-A-61 023 695 und JP-A-59 176 641 wird die Verwendung von Benz- oxalylthiophenen bzw. Anthracen-Derivaten und in US-A-5 421 192 die Ver- wendung von Naphthalimiden als fluoreszierende Farbstoffe zur leichteren Detektion von undichten Stellen beschrieben. Die im Stand der Technik verwendeten Farbstoffe zeigen jedoch anwendungstechnische Nachteile, da sie eine ungenügende Stabilität, beispielsweise Oxidationsstabilität unter den Einsatzbedingungen zeigen oder sich schlecht beispielsweise in Hydrauliköle einarbeiten lassen. Ein weiterer Nachteil ist die geringe Farbstärke, mit der entsprechend hohe Einsatzmengen des Farbstoffs erforderlich werden und/oder das Detektieren an den entsprechenden Leckstellen mit zusätzlichen Hilfsmitteln, wie UV-Lampe usw. Es wurde nun gefunden, daß Cumarinfarbstoffe enthaltende Schmiermittel diese Nachteile nicht mehr aufweisen. Als bevorzugter Cumarinfarbstoff wird unsubstituiertes oder gegebenenfalls substi- tuiertes Cumarin eingesetzt. Besonders bevorzugt werden Cumarinfarbstoffe derAccording to JP-A-61 023 695 and JP-A-59 176 641 the use of benzoxalylthiophenes or anthracene derivatives and in US-A-5 421 192 the use of naphthalimides as fluorescent dyes for easier detection of leaks described. However, the dyes used in the prior art have disadvantages in terms of application technology, since they show insufficient stability, for example oxidation stability under the conditions of use, or are difficult to incorporate, for example, into hydraulic oils. Another disadvantage is the low color strength, with which correspondingly high amounts of the dye are required and / or the detection at the corresponding leak points with additional aids, such as UV lamps, etc. It has now been found that lubricants containing coumarin dyes no longer have these disadvantages . Unsubstituted or optionally substituted coumarin is used as the preferred coumarin dye. Coumarin dyes are particularly preferred
Formel (I) eingesetztFormula (I) used
(I),(I),
R^ und R2 unabhängig voneinander für C]-C -Alkyl, insbesondere für Methyl und Ethyl stehen,
2 -R ^ and R 2 independently of one another are C ] -C -alkyl, in particular methyl and ethyl, 2 -
R3 bis R6 unabhängig voneinander für H, Cj-C^Alkyl, insbesondere CH3 und tert.-Butyl, Halogen, insbesondere Cl, Sulfonamid, insbesondere -SO2NH2 und -SO2N(CH3)2, CrC4-Alkylsulfonyl, insbesondere -SO C2H5, C -C -Cycloalkyl, insbesondere Cyclohexyl oder Cg-Cio- Aryl, insbesondere Phenyl stehen,R 3 to R 6 independently of one another are H, C 1 -C 4 -alkyl, in particular CH 3 and tert-butyl, halogen, in particular Cl, sulfonamide, in particular -SO 2 NH 2 and -SO 2 N (CH 3 ) 2 , C r C 4 alkylsulfonyl, in particular -SO C 2 H 5 , C -C -cycloalkyl, in particular cyclohexyl or Cg-Cio-aryl, in particular phenyl,
R7 oder CN bedeutet undR7 or CN means and
X für O oder S steht.X stands for O or S.
Ganz besonders bevorzugte Cumarinfarbstoffe der Formel (I) sind solche, die der Formel (II) entsprechenVery particularly preferred coumarin dyes of the formula (I) are those which correspond to the formula (II)
(II),(II),
(H5C2)2N
(H 5 C 2 ) 2 N
worinwherein
R4 für Cl oder SO2NH2 steht.R 4 represents Cl or SO 2 NH 2 .
Diese Farbstoffe und ihre Herstellung sind bekannt. Sie werden beispielsweise in DE-A-28 44 299 offenbart.These dyes and their preparation are known. They are disclosed for example in DE-A-28 44 299.
Als Schmiermittel werden vorzugsweise natürliche oder raffinierte Mineralöle, synthetische Kohlenwasserstoffe, Alkylbenzole, Polyalphaolefine, Polyalkylen- glykole sowie Polyester eingesetzt. Bevorzugt werden Schmiermittel eingesetzt mit einer Viskosität von 5 bis 200, insbesondere 10 bis 100 cSt, bei 40°C.
Bevorzugt ist es, den Cumarinfarbstoff in einer Menge von 0,0001 bis 0,1 %, vorzugsweise von 0,001 bis 0,03 %, bezogen auf das Schmiermittel, einzusetzen.Natural or refined mineral oils, synthetic hydrocarbons, alkylbenzenes, polyalphaolefins, polyalkylene glycols and polyesters are preferably used as lubricants. Lubricants with a viscosity of 5 to 200, in particular 10 to 100 cSt, at 40 ° C. are preferably used. It is preferred to use the coumarin dye in an amount of 0.0001 to 0.1%, preferably 0.001 to 0.03%, based on the lubricant.
Die Erfindung betrifft weiterhin ein Verfahren zur Herstellung der erfin- dungsgemäßen Schmiermittel, dadurch gekennzeichnet, daß man einen Cumarinfarbstoff, gegebenenfalls in Gegenwart geeigneter organischer Lösungsmittel, in das Schmiermittel einbringt und anschließend das gegebenenfalls verwendete organische Lösungsmittel, vorzugsweise thermisch, insbesondere destillativ vom Schmiermittel entfernt. Als mögliches Lösungsmittel wird vorzugsweise ein mit Öl verträgliches und leicht abdestillierbares Lösungsmittel verwendet, in dem derThe invention further relates to a process for the preparation of the lubricants according to the invention, characterized in that a coumarin dye, if appropriate in the presence of suitable organic solvents, is introduced into the lubricant and then the optionally used organic solvent is removed from the lubricant, preferably thermally, in particular by distillation. A possible solvent is preferably an oil-compatible and easily distilled off solvent, in which the
Cumarinfarbstoff zugleich löslich ist. Als mögliche organische Lösungsmittel sind dabei aromatische Kohlenwasserstoffe wie beispielsweise Toluol oder Xylol zu nennen. Das Einbringen des Cumarinfarbstoffes in das Schmiermittel als solches oder in gelöster Form erfolgt bei einer Temperatur von 15°C bis 220°C, insbesondere bei -20 bis 150°C, vorzugsweise durch Rühren.Coumarin dye is soluble at the same time. Aromatic hydrocarbons such as toluene or xylene can be mentioned as possible organic solvents. The coumarin dye is introduced into the lubricant as such or in dissolved form at a temperature of 15 ° C. to 220 ° C., in particular at -20 to 150 ° C., preferably by stirring.
Die Erfindung betrifft weiterhin die Verwendung des Cumarinfarbstoff enthaltenden Schmiermittels als Hydrauliköl, beispielsweise als Bremsflüssigkeit oder zum Einarbeiten in Kühlflüssigkeiten. Als mögliche Kühlflüssigkeiten sind in dem Zusam- menhang zu nennen, beispielsweise Fluorkohlenwasserstoffe, Fluorchlorkohlenwasserstoffe und Methan, Ethan, Propan, Butan oder Pentan und deren Halogen- und Ether-Derivaten sowie deren Mischungen als auch Mischungen von Fluorkohlenwasserstoffen und Fluorchlorkohlenwasserstoffen sowie Kohlendioxid und Ammoniak. Bevorzugt wird das erfindungsgemäße Schmiermittel in Hydrau- likölen insbesondere in solchen aus natürlichen oder synthetischen Mineralölen eingesetzt. Derartig verwendetes erfindungsgemäßes Schmiermittel hat den Vorteil, daß undichte Stellen bei Tageslicht oder bei Beleuchtung mit einer Lampe, die bei einer Wellenlänge zwischen 380 und 500 nm emitiert durch eine grünlich-gelbe bis orange Fluoreszenz farblich erkannt werden kann. Im übrigen sind die eingangs erwähnten Vorteile zu nennen.
- 4 -The invention further relates to the use of the lubricant containing coumarin dye as hydraulic oil, for example as a brake fluid or for incorporation in cooling fluids. Possible cooling liquids in this connection are, for example, fluorocarbons, chlorofluorocarbons and methane, ethane, propane, butane or pentane and their halogen and ether derivatives and their mixtures and also mixtures of fluorocarbons and chlorofluorocarbons as well as carbon dioxide and ammonia. The lubricant according to the invention is preferably used in hydraulic oils, in particular those made from natural or synthetic mineral oils. Lubricant according to the invention used in this way has the advantage that leaks in daylight or when illuminated with a lamp which emits at a wavelength between 380 and 500 nm can be identified by a greenish-yellow to orange fluorescence. For the rest, the advantages mentioned at the beginning are to be mentioned. - 4 -
Beispielexample
Beispiel 1example 1
1000 Teile eines raffinierten Mineralöls Viskosität: 68 cSt, gemessen bei 40°C;1000 parts of a refined mineral oil Viscosity: 68 cSt, measured at 40 ° C;
(Hydrauliköl der Firma Texaco, Typ Rando® HDZ 68) werden mit einer Lösung von 0,05 Teilen des Farbstoffs der Formel (II) mit R = Cl in 3 Teilen Toluol versetzt. Nach Entfernen des Toluols durch Destillation wurde das Öl als Hydrauliköl eingesetzt. Undichte Stellen in dem Hydraulikkreislauf können mit einer grünlich- gelben Fluoreszenz an der Leckstelle erkannt werden.(Hydraulic oil from Texaco, type Rando® HDZ 68) are mixed with a solution of 0.05 part of the dye of formula (II) with R = Cl in 3 parts of toluene. After the toluene was removed by distillation, the oil was used as hydraulic oil. Leakages in the hydraulic circuit can be detected with a greenish-yellow fluorescence at the leak.
In analoger Weise wurde raffiniertes Mineralöl mit anderen Viskositäten mit diesem Farbstoff eingefärbt. So wurden die folgenden raffinierten Mineralöle eingefärbt:In a similar way, refined mineral oil with different viscosities was colored with this dye. The following refined mineral oils were colored:
Viskosität: 15 cSt, gemessen bei 40°C (Rando® HDZ 15 der Firma Texaco)Viscosity: 15 cSt, measured at 40 ° C (Rando® HDZ 15 from Texaco)
Viskosität: 22 cSt, gemessen bei 40°C (Rando® HDZ 22 der Firma Texaco) Viskosität: 32 cSt, gemessen bei 40°C (Rando® HDZ 32 der Firma Texaco) Viskosität: 46 cSt, gemessen bei 40°C (Rando® HDZ 46 der Firma Texaco) und Viskosität: 100 cSt, gemessen bei 40°C (Rando® HDZ 100 der Firma Texaco).Viscosity: 22 cSt, measured at 40 ° C (Rando® HDZ 22 from Texaco) Viscosity: 32 cSt, measured at 40 ° C (Rando ® HDZ 32 from Texaco) Viscosity: 46 cSt, measured at 40 ° C (Rando ® HDZ 46 from Texaco) and viscosity: 100 cSt, measured at 40 ° C (Rando® HDZ 100 from Texaco).
Beispiel 2Example 2
Analog Beispiel 1 wurde raffiniertes Mineralöl mit dem Farbstoff der Formel (II) mit R = SO2NH2 eingefärbt. Mit diesem Farbstoff wurden in gleicher Weise wie in Beispiel 1 raffinierte Mineralöle unterschiedlicher Viskositätsbereiche, wie oben beschrieben, eingefärbt.
Analogous to Example 1, refined mineral oil was colored with the dye of the formula (II) with R = SO 2 NH 2 . Refined mineral oils of different viscosity ranges, as described above, were colored with this dye in the same way as in Example 1.
Claims
- 5 - 5th
Patentansprücheclaims
Cumarinfarbstoff enthaltende Schmiermittel.Lubricants containing coumarin dye.
Schmiermittel gemäß Anspruch 1 enthaltend als Cumarinfarbstoff substituiertes oder unsubstituiertes Cumarin.Lubricants according to claim 1 containing substituted or unsubstituted coumarin as coumarin dye.
Schmiermittel gemäß Anspruch 1 enthaltend als Cumarinfarbstoff eine Verbindung der Formel (I)Lubricant according to claim 1 containing as coumarin dye a compound of formula (I)
(I),(I),
R1 und R2 unabhängig voneinander für Cι-C4-Alkyl, insbesondere für Methyl und Ethyl stehen,R 1 and R 2 independently of one another are C 1 -C 4 -alkyl, in particular methyl and ethyl,
R3 bis R6 unabhängig voneinander für H, Cι-C4-Alkyl, insbesondere CH3 und tert.-Butyl, Halogen, insbesondere Cl, Sulfonamid, insbesondere -SO2NH2 und -SO2N(CH3)2, C,-C4-Alkylsulfonyl, insbesondere -SO2C2H5, C4-C7-Cycloalkyl, insbesondere Cyclohexyl oder C6- Cj0-Aryl, insbesondere Phenyl stehen,R 3 to R 6 independently of one another for H, -CC 4 alkyl, in particular CH3 and tert-butyl, halogen, in particular Cl, sulfonamide, in particular -SO 2 NH 2 and -SO 2 N (CH 3 ) 2 , C , -C 4 alkylsulfonyl, in particular -SO 2 C 2 H 5 , C 4 -C 7 cycloalkyl, in particular cyclohexyl or C 6 - C j0 aryl, in particular phenyl,
R7 H oder CN bedeutet undR 7 denotes H or CN and
X für O oder S steht.
- 6 -X stands for O or S. - 6 -
4. Schmiermittel gemäß Anspruch 1, dadurch gekennzeichnet, daß als Cumarinfarbstoff eine Verbindung der Formel (II)4. Lubricant according to claim 1, characterized in that a compound of formula (II) as coumarin dye
(II),(II),
R4 für Cl oder SO2NH2 steht,R 4 represents Cl or SO 2 NH 2 ,
eingesetzt wird.is used.
5. Schmiermittel gemäß Anspruch 1, dadurch gekennzeichnet, daß der Cumarinfarbstoff in einer Menge von 0,0001 bis 0,1 %, bezogen auf das Schmiermittel, eingesetzt wird.5. Lubricant according to claim 1, characterized in that the coumarin dye is used in an amount of 0.0001 to 0.1%, based on the lubricant.
6. Schmiermittel gemäß Anspruch 1 enthaltend als Schmiermittel natürliches oder raffiniertes Mineralöl, synthetische Kohlenwasserstoffe, Alkylbenzole,6. Lubricant according to claim 1 containing as a lubricant natural or refined mineral oil, synthetic hydrocarbons, alkylbenzenes,
Polyalphaolefine, Polyalkylenglykole oder Polyester.Polyalphaolefins, polyalkylene glycols or polyesters.
7. Schmiermittel gemäß Anspruch 1, dadurch gekennzeichnet, daß das Schmiermittel eine Viskosität von 5 bis 200 cSt, bei 40°C, besitzt.7. Lubricant according to claim 1, characterized in that the lubricant has a viscosity of 5 to 200 cSt, at 40 ° C.
8. Verfahren zur Herstellung von Schmiermitteln gemäß Anspruch 1, dadurch gekennzeichnet, daß ein Cumarinfarbstoff, gegebenenfalls gelöst in einem organischen Lösungsmittel, in das Schmiermittel eingearbeitet wird, und anschließend gegebenenfalls verwendetes organisches Lösungsmittel entfernt wird.
Verwendung eines Cumarinfarbstoff enthaltenden Schmiermittels gemäß Anspruch 1 als Hydrauliköl oder zur Einbringung in Kühlflüssigkeiten.
8. A process for the production of lubricants according to claim 1, characterized in that a coumarin dye, optionally dissolved in an organic solvent, is incorporated into the lubricant, and then optionally used organic solvent is removed. Use of a lubricant containing coumarin dye according to claim 1 as hydraulic oil or for introduction into cooling liquids.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU38188/99A AU3818899A (en) | 1998-04-29 | 1999-04-19 | Lubricants containing coumarin dyes |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1998119020 DE19819020A1 (en) | 1998-04-29 | 1998-04-29 | Lubricants containing coumarin dyes |
| DE19819020.4 | 1998-04-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1999055807A1 true WO1999055807A1 (en) | 1999-11-04 |
Family
ID=7866080
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP1999/002626 WO1999055807A1 (en) | 1998-04-29 | 1999-04-19 | Lubricants containing coumarin dyes |
Country Status (3)
| Country | Link |
|---|---|
| AU (1) | AU3818899A (en) |
| DE (1) | DE19819020A1 (en) |
| WO (1) | WO1999055807A1 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6132636A (en) * | 1998-10-23 | 2000-10-17 | Allied Signal Inc | Leak-detecting refrigerant compositions containing oxazolyl-coumarin dyes |
| JP5972640B2 (en) * | 2012-03-30 | 2016-08-17 | 出光興産株式会社 | Lubricating oil composition for refrigerator |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB780622A (en) * | 1954-06-24 | 1957-08-07 | Gen Electric | Improvements in the stabilization of organo-siloxanes |
| EP0046250A1 (en) * | 1980-08-20 | 1982-02-24 | Bayer Ag | Dyestuff preparation and its use as a warning and signalling colour |
| US5681984A (en) * | 1996-07-22 | 1997-10-28 | Bright Solutions, Inc. | Leak detection in heating, ventilating, refrigeration, and air conditioning systems utilizing adsorptive materials |
-
1998
- 1998-04-29 DE DE1998119020 patent/DE19819020A1/en not_active Withdrawn
-
1999
- 1999-04-19 WO PCT/EP1999/002626 patent/WO1999055807A1/en active Application Filing
- 1999-04-19 AU AU38188/99A patent/AU3818899A/en not_active Abandoned
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB780622A (en) * | 1954-06-24 | 1957-08-07 | Gen Electric | Improvements in the stabilization of organo-siloxanes |
| EP0046250A1 (en) * | 1980-08-20 | 1982-02-24 | Bayer Ag | Dyestuff preparation and its use as a warning and signalling colour |
| US5681984A (en) * | 1996-07-22 | 1997-10-28 | Bright Solutions, Inc. | Leak detection in heating, ventilating, refrigeration, and air conditioning systems utilizing adsorptive materials |
Also Published As
| Publication number | Publication date |
|---|---|
| AU3818899A (en) | 1999-11-16 |
| DE19819020A1 (en) | 1999-11-04 |
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