EP0085949B1 - Stabilized trichloroethene and means for stabilizing trichloroethene - Google Patents
Stabilized trichloroethene and means for stabilizing trichloroethene Download PDFInfo
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- EP0085949B1 EP0085949B1 EP83101002A EP83101002A EP0085949B1 EP 0085949 B1 EP0085949 B1 EP 0085949B1 EP 83101002 A EP83101002 A EP 83101002A EP 83101002 A EP83101002 A EP 83101002A EP 0085949 B1 EP0085949 B1 EP 0085949B1
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- trichloroethene
- hydroxyanisole
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/22—Organic compounds
- C11D7/26—Organic compounds containing oxygen
- C11D7/261—Alcohols; Phenols
- C11D7/262—Alcohols; Phenols fatty or with at least 8 carbon atoms in the alkyl or alkenyl chain
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/50—Solvents
- C11D7/5004—Organic solvents
- C11D7/5018—Halogenated solvents
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
- D06L1/00—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods
- D06L1/02—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods using organic solvents
- D06L1/04—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods using organic solvents combined with specific additives
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/22—Organic compounds
- C11D7/24—Hydrocarbons
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/22—Organic compounds
- C11D7/26—Organic compounds containing oxygen
- C11D7/266—Esters or carbonates
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/22—Organic compounds
- C11D7/28—Organic compounds containing halogen
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/22—Organic compounds
- C11D7/32—Organic compounds containing nitrogen
- C11D7/3281—Heterocyclic compounds
Definitions
- a commonly used, well stabilizing additive for trichlorethylene is butylene oxide.
- Stabilizing mixtures containing nitriles, such as propionitrile, acrylonitrile and the like, have also proven useful for trichlorethylene, which is used as an auxiliary for paints.
- GB-A-932,138 claims a stabilizer system for trichlorethylene which contains as components an organic amine, an epoxy compound and a quaternary ammonium salt.
- the replacement of carcinogenic butylene oxide by non-toxic epoxides is not described, but in all examples, butylene oxide is emphasized.
- Example 2 describes a stabilizer mixture of butylene oxide, triethylamine, cetyltrimethylammonium bromide or trimethylammonium chloride, isopropanol, N-methylpyrrole and diisobutylene.
- a disadvantage of this stabilizer mixture is the addition of the quaternary ammonium salt described as essential, since these compounds cause severe corrosion when the stabilized trichlorethylene is applied.
- FR-A 1 233 249 describes a stabilizer mixture of amine and a combination of two different epoxides, the one being selected from butylene oxide, propylene oxide and 2-methylbutene oxide, the other styrene oxide, a-methylstyrene oxide, a-pinene oxide, lime mono- or can be dioxide.
- the problem of the use of toxic butylene oxide and its substitution by non-toxic epoxides is not described. Rather, Table (111) teaches substitution of butylene or propylene oxide.
- the object of the invention was to provide means for stabilizing trichlorethylene and thus stabilized trichlorethylene which does not contain the stabilizing additives mentioned above. Furthermore, it was an object of the invention to find agents for stabilizing trichlorethylene which can make appropriately formulated trichlorethylene suitable both as an auxiliary for paints and as a degreasing agent.
- the invention furthermore relates to stabilized trichorethylene which contains the stabilizer mixture according to the invention.
- the amount of stabilizer is generally between 3,200 and 25,000 ppm by weight, preferably 5,000 to 10,000 ppm by weight, in each case based on the total amount of stabilized trichloroethene.
- Amines boiling between 70 and 110 ° C at 1 bar are equivalent to diisopropylamine in the context of the invention. Examples of these are triethylamine and dimethylisobutylamine.
- the proportion of epoxides is preferably 4,000 to 6,000 ppm by weight.
- the BAM test was unresponsive.
- the accelerated oxidation test according to MIL-T-81533 A gave one. Service life of 1920 hours.
- the pH was 9.5 after 48 hours.
- the test liquid was colorless.
- the service life until the acidity limit of 0.02% by weight of HCl was reached was 240 hours.
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Abstract
Description
Bekanntlich muß Trichlorethan gegen die zersetzenden Einflüsse von Wärme, Licht, Luft, Feuchtigkeit und Metallen stabilisiert werden.As is known, trichloroethane must be stabilized against the decomposing effects of heat, light, air, moisture and metals.
Ein häufig eingesetzter, gut stabilisierender Zusatz für Trichlorethen ist Butylenoxid. Für Trichlorethen, das als Hilfsstoff für Lacke eingesetzt wird, haben sich ferner stabilisierende Mischungen, die Nitrile, wie Propionitril, Acrylnitril und dergleichen enthalten, bewährt.A commonly used, well stabilizing additive for trichlorethylene is butylene oxide. Stabilizing mixtures containing nitriles, such as propionitrile, acrylonitrile and the like, have also proven useful for trichlorethylene, which is used as an auxiliary for paints.
Es wurden nun in jüngster Zeit toxikologische Untersuchungen bekannt, die es angeraten sein lassen, Nitrile und namentlich Butylenoxid als stabilisierende Zusätze für Trichlorethen nicht mehr zu verwenden.Recently, toxicological studies have become known which make it advisable not to use nitriles and especially butylene oxide as stabilizing additives for trichloroethene.
Aus der Literatur sind eine Reihe von Stabilisatorsystemen zur Trichlorethylenstabilisierung bekannt. Die Problematik des Einsatzes von Butylenoxid bzw. Nitrilen zur Stabilisierung wird jedoch nicht erkannt.A number of stabilizer systems for trichlorethylene stabilization are known from the literature. However, the problem of using butylene oxide or nitriles for stabilization is not recognized.
In der GB-A-932,138 wird ein Stabilisatorsystem für Trichlorethylen beansprucht, das als Komponenten ein organisches Amin, eine Epoxidverbindung und ein quartäres Ammoniumsalz enthält. Der Ersatz des cancerogenen Butylenoxids durch nicht-toxische Epoxide wird nicht beschrieben, vielmehr wird in allen Beispielen Butylenoxid herausgehoben. In Beispiel 2 wird ein Stabilisatorgemisch aus Butylenoxid, Triethylamin, Cetyltrimethylammoniumbromid oder Trimethylammoniumchlorid, Isopropanol, N-Methylpyrrol und Diisobutylen beschrieben. Nachteilig bei diesem Stabilisatorgemisch wirkt sich von allem die Zugabe des als essentiell beschriebenen quartären Ammoniumsalzes aus, da diese Verbindungen bei der Applikation des stabilisierten Trichlorethylens starke Korrosion verursachen.GB-A-932,138 claims a stabilizer system for trichlorethylene which contains as components an organic amine, an epoxy compound and a quaternary ammonium salt. The replacement of carcinogenic butylene oxide by non-toxic epoxides is not described, but in all examples, butylene oxide is emphasized. Example 2 describes a stabilizer mixture of butylene oxide, triethylamine, cetyltrimethylammonium bromide or trimethylammonium chloride, isopropanol, N-methylpyrrole and diisobutylene. A disadvantage of this stabilizer mixture is the addition of the quaternary ammonium salt described as essential, since these compounds cause severe corrosion when the stabilized trichlorethylene is applied.
Die FR-A 1 233 249 beschreibt ein Stabilisatorgemisch aus Amin und einer Kombination zweier verschiedener Epoxide, wobei das eine aus Butylenoxid, Propylenoxid und 2-Methylbutenoxid enthaltenden Gruppe auszuwählen ist, das andere Styroloxid, a-Methylstyroloxid, a-Pinenoxid, Limonenmono- oder dioxid sein kann. Die Problematik des Einsatzes des toxischen Butylenoxids und dessen Substitution durch nicht-toxische Epoxide wird nicht beschrieben. Tabelle (111) lehrt vielmehr von der Substitution von Butylen- oder Propylenoxid weg.FR-A 1 233 249 describes a stabilizer mixture of amine and a combination of two different epoxides, the one being selected from butylene oxide, propylene oxide and 2-methylbutene oxide, the other styrene oxide, a-methylstyrene oxide, a-pinene oxide, lime mono- or can be dioxide. The problem of the use of toxic butylene oxide and its substitution by non-toxic epoxides is not described. Rather, Table (111) teaches substitution of butylene or propylene oxide.
In der DE―B 2 136 695 wird ein ternäres Stabilisatorgemisch bestehend aus Diisopropylamin, einem Phenol und einem Alkenoxid beansprucht. Als Alkenoxide werden ausdrücklich das toxische Butylenoxid bzw. Propylenoxid genannt. Eine Substitution dieser toxischen Epoxide wird nicht beschrieben.DE ― B 2 136 695 claims a ternary stabilizer mixture consisting of diisopropylamine, a phenol and an alkene oxide. Toxic butylene oxide or propylene oxide are expressly mentioned as alkene oxides. A substitution of these toxic epoxides is not described.
Die US―A 2,797,250 beansprucht ein Stabilisatorsystem bestehend aus einem aromatischen Amin und einem Epoxid, gegebenenfalls unter Zusatz von N-Methylpyrrol und Ethylacetat. Als bevorzugtes Epoxid wird Butylenoxid beansprucht. Die Problematik der Substitution von toxischem Butytenc bzw. toxischen Nitrilen bei der Trichlorethylenstabilisierung wird nicht beschrieben.The US 2,7 A 2,797,250 claims a stabilizer system consisting of an aromatic amine and an epoxide, optionally with the addition of N-methylpyrrole and ethyl acetate. Butylene oxide is claimed as the preferred epoxy. The problem of the substitution of toxic butytenc or toxic nitriles in trichlorethylene stabilization is not described.
Aufgabe der Erfindung war es, Mittel zur Stabilisierung von Trichlorethen und somit stabilisiertes Trichlorethen zur Verfügung zu stellen, das die obengenannten Stabilisierungszusätze nicht enthält. Weiterhin war es Aufgabe der Erfindung, Mittel zur Stabilisierung von Trichlorethen aufzufinden, die entsprechend formuliertes Trichlorethen sowohl als Hilfsstoff für Lacke als auch als Entfettungsmittel geeignet machen können.The object of the invention was to provide means for stabilizing trichlorethylene and thus stabilized trichlorethylene which does not contain the stabilizing additives mentioned above. Furthermore, it was an object of the invention to find agents for stabilizing trichlorethylene which can make appropriately formulated trichlorethylene suitable both as an auxiliary for paints and as a degreasing agent.
Gegenstand der Erfindung ist ein Mittel zur Stabilisierung von Trichlorethen, das durch die Kombination der folgenden Bestandteile gekennzeichnet ist:
- a) N-Methylpyrrol und/oder 2-tert.-Butylphenol und/oder 2.4-Ditert.-Butylphenol und/oder 4-Hydroxyanisol und/oder 2-tert.-Butyl-4-hydroxyanisol und/oder 3-tert.-Butyl-4-hydroxyanisol und/oder 2.6-Dimethylphenol.
- b) 2-Methyl-2.3-epoxybutan und/oder 2.3-Dimethyl-2.3-epoxybutan und/oder 3.3-Dimethyl-1.2-epoxybutan und/oder 1.2-Epoxypentan und/oder Cyclopentenoxid
- c) Diisobutylen
- d) Ethylacetat und/oder Propylacetat
- e) Diisopropylamin
- a) N-methylpyrrole and / or 2-tert-butylphenol and / or 2,4-di-tert-butylphenol and / or 4-hydroxyanisole and / or 2-tert.-butyl-4-hydroxyanisole and / or 3-tert.- Butyl-4-hydroxyanisole and / or 2,6-dimethylphenol.
- b) 2-methyl-2,3-epoxybutane and / or 2,3-dimethyl-2,3-epoxybutane and / or 3,3-dimethyl-1,2-epoxybutane and / or 1,2-epoxypentane and / or cyclopentene oxide
- c) diisobutylene
- d) ethyl acetate and / or propyl acetate
- e) diisopropylamine
Gegenstand der Erfindung ist weiterhin stabilisiertes Trichorethylen, das die erfindungsgemäße Stabilisatormischung enthält. Die Stabilisatormenge liegt in der Regel zwischen 3.200 und 25.000 Gew.ppm, vorzugsweise bei 5.000 bis 10.000 Gew.ppm, jeweils bezogen auf die Gesamtmenge stabilisierten Trichlorethens.The invention furthermore relates to stabilized trichorethylene which contains the stabilizer mixture according to the invention. The amount of stabilizer is generally between 3,200 and 25,000 ppm by weight, preferably 5,000 to 10,000 ppm by weight, in each case based on the total amount of stabilized trichloroethene.
Vorzugsweise enthält das erfindungsgemäß stabilisierte Trichlorethen.
- a1) 0-500 Gew.ppm N-Methylpyrrol
- a2) 0-500 Gew.ppm 2-tert.-Butylphenol und/oder 2.4-Di-tert.-Butylphenol und/oder 4-Hydroxyanisol und/oder 2-tert.-Butyl-4-hydroxyanisol und/oder 3-tert.-Butyl-4-hydroxyanisol und/oder 2.6-Dimethylphenol
- a1) 0-500 ppm by weight of N-methylpyrrole
- a2) 0-500 ppm by weight of 2-tert-butylphenol and / or 2,4-di-tert-butylphenol and / or 4-hydroxyanisole and / or 2-tert.-butyl-4-hydroxyanisole and / or 3-tert .-Butyl-4-hydroxyanisole and / or 2,6-dimethylphenol
mit der Maßgabe, daß die Komponenten gemäß a1 und a2 zumindest in einer Menge von 10 Gew.ppm vorliegen,
- b) 1.000―8.000 Gew.ppm 2-Methyl-2.3-epoxybutan und/oder 2.3-Dimethyl-2.3-epoxybutan und/oder 3.3-Dimethyi-1.2-epoxybutan und/oder 1.2-Epoxypentan und/oder Cyclopentenoxid
- c) 100-4.000 Gew.ppm Diisobutylen
- d) 2.000-3.000 Gew.ppm Ethylacetat und/oder Propylacetat
- e) 10-100 Gew.ppm Diisopropylamin
- b) 1,000-8,000 ppm by weight of 2-methyl-2,3-epoxybutane and / or 2,3-dimethyl-2,3-epoxybutane and / or 3,3-dimethyi-1,2-epoxybutane and / or 1,2-epoxypentane and / or cyclopentene oxide
- c) 100-4,000 ppm by weight diisobutylene
- d) 2,000-3,000 ppm by weight of ethyl acetate and / or propyl acetate
- e) 10-100 ppm by weight diisopropylamine
Amine, die bei 1 bar zwischen 70 und 110°C sieden, sind Diisopropylamin im Rahmen der Erfindung äquivalent. Beispiele hierfür sind Triethylamin und Dimethylisobutylamin.Amines boiling between 70 and 110 ° C at 1 bar are equivalent to diisopropylamine in the context of the invention. Examples of these are triethylamine and dimethylisobutylamine.
Vorzugsweise beträgt der Anteil un Epoxiden (gemäß b)) 4.000 bis 6.000 Gew.ppm.The proportion of epoxides (according to b)) is preferably 4,000 to 6,000 ppm by weight.
Bie erfindungsgemäßem Trichlorethen als Hilfsstoff für Lacke beträgt der Anteil an N-Methylpyrrol vorzugsweise maximal 10 Gew.ppm, besonders bevorzugt 0 oder 0 bis 5 Gew.ppm. Vorteilhafterweise wird die Menge eingesetzten Diisobutylens auf Menge und Art des Phenols abgestimmt:
- Bei 1.000 bis 3.000 Gew.ppm Diisobutylen beträgt die optimale Konzentration für
- 2-tert.-Butylphenol und 2.4-Ditert.-Butylphenol 200 bis 500 Gew.ppm und für
- 4-Hydroxyanisol 50 bis 100 Gew.ppm.
- At 1,000 to 3,000 ppm by weight diisobutylene, the optimal concentration for
- 2-tert-butylphenol and 2.4-di-tert-butylphenol 200 to 500 ppm by weight and for
- 4-hydroxyanisole 50 to 100 ppm by weight.
Bei Einsatz von 2-tert.-Butyl-4-hydroxyanisol werden vorzugsweise lediglich 10 bis 50 Gew.ppm neben 100 bis 200 Gew.ppm Diisobutylen zugegeben.When using 2-tert-butyl-4-hydroxyanisole, preferably only 10 to 50 ppm by weight in addition to 100 to 200 ppm by weight of diisobutylene are added.
Zur Prüfung auf Stabilität wurde das erfindungsgemäße Trichlorethen den drei folgenden Tests unterworfen:
- 1. Es wurde der beschleunigte Oxidationstest nach MIL-T-81533 A durchgeführt. Als Testapparatur diente ein mit 200 ml erfindungsgemäß stabilisierten Trichlorethens gefülltes Siedegefäß mit Rückflußkühler, das mittels einer 150-Watt-Glühlampe beheizt wurde. In die Testflüssigkeit wurde ein stetiger wasserdampfgesättigter Sauerstoffstrom (10 bis 12 Blasen pro Minute) geleitet.
- 1. The accelerated oxidation test according to MIL-T-81533 A was carried out. A boiling vessel filled with 200 ml of trichlorethylene stabilized according to the invention and with a reflux condenser was used as the test apparatus and was heated by means of a 150 watt incandescent lamp. A steady stream of oxygen saturated with water vapor (10 to 12 bubbles per minute) was passed into the test liquid.
Weiter war ein Streifen aus metallischem Aluminium so angeordnet, daß er zur Hälfte in die Testflüssigkeit eintauchte. Ein zweiter Aluminiumstreifen befand sich am Gefäßboden.Furthermore, a strip of metallic aluminum was arranged so that half of it was immersed in the test liquid. A second aluminum strip was on the bottom of the vessel.
Als Stabilitätskriterium wurde die Zeit herangezogen, die das stabilisierte Trichlorethen den obigen Testbedingungen ausgesetzt werden mußte, bis ein HCI-Gehalt von 0,02 Gew.% erreicht war. Der HCI-Gehalt wurde durch regelmäßige Probeentnahme und anschließende Titration mit 0,1 n NaOH gegen Phenolphthalein ermittelt.
- 2. DKH-Test: Es wurde die oben beschriebene Testanordnung benutzt, mit der Abänderung, daß anstatt der Aluminiumstreifen Stahlstreifen eingesetzt wurden.
- 2. DKH test: The test arrangement described above was used, with the modification that steel strips were used instead of the aluminum strips.
Nach 48 Stunden wurde auf pH-Wert und Farbe der Testflüssigkeit bonitiert. Ferner wurde die Standzeit bis zum Erreichen der Aciditätsgrenze von 0,02 Gew.% HCI-Gehalt ermittelt.
- 3. Als weitere Qualitätsprüfung diente eine von der Bundesanstalt für Materialprüfung vorgeschlagene. Testmethode (BAM-Test): Hierzu wurden 100 ml erfindungsgemäß stabilisierten Trichlorethens mit 100 ml Toluol vermischt und zusammen mit 18 g Aluminiumflitter einer Teilchengröße <0,5 mm und zusammen mit 0,7 g wasserfreien Aluminiumchlorids 18 Stunden am Rückfluß gekocht. Eine zweite, im übrigen gleiche Probe enthielt zusätzlich 1 g Zinkstearat und eine dritte Probe zusätzlich 10 ml Ölsäure. Schließlich wurden die drei beschriebenen Tests noch mit Destillaten des erfindungsgemäß stabilisierten Trichlorethens wiederholt. Das Prüfverfahren galt ist bestanden, wenn die keinem der beschriebenen Einzeltests exotherme Reaktionen auftraten.
- 3. Another quality check was one proposed by the Federal Institute for Material Testing. Test method (BAM test): For this purpose, 100 ml of trichlorethylene stabilized according to the invention were mixed with 100 ml of toluene and refluxed together with 18 g of aluminum flakes with a particle size of <0.5 mm and together with 0.7 g of anhydrous aluminum chloride for 18 hours. A second sample, which was otherwise the same, additionally contained 1 g zinc stearate and a third sample additionally 10 ml oleic acid. Finally, the three tests described were repeated with distillates of the trichlorethylene stabilized according to the invention. The test procedure has been passed if none of the individual tests described resulted in exothermic reactions.
Die Erfindung wird nun anhand von Beispielen und Vergleichsbeispielen näher erläutert. Die Daten beziehen sich auf die Ergebnisse der drei oben beschriebenen Tests. Das Zeichen (-) steht für keine Reaktion während des BAM-Tests.The invention will now be explained in more detail by means of examples and comparative examples. The data refer to the results of the three tests described above. The sign (-) stands for no reaction during the BAM test.
3 kg Trichlorethen wurden mit 0,9 g N-Methylpyrrol, 15 g 2-Methyl-2.3-epoxybutan, 8,3 g Diisobutylen, 8,3 g Ethylacetat und 0,08 Diisopropylamin versetzt.3 kg of trichlorethylene were mixed with 0.9 g of N-methylpyrrole, 15 g of 2-methyl-2,3-epoxybutane, 8.3 g of diisobutylene, 8.3 g of ethyl acetate and 0.08 diisopropylamine.
Der BAM-Test verlief ohne Reaktion. Der beschleunigte Oxidationstest nach MIL-T-81533 A ergab eine . Standzeit von 1920 Stunden.The BAM test was unresponsive. The accelerated oxidation test according to MIL-T-81533 A gave one. Service life of 1920 hours.
Weitere Ergebnisse von Tests, die analog Beispiel 1 durchgeführt wurden, werden in der nun folgenden Tabelle aufgeführt.
Es wurden 3 kg Trichlorethylen mit 0,66 g 2.4-Ditert.-Butylphenol, 13,5 g 2-Methyl-2.3-epoxybutan, 6 g Diisobutylen, 8,4 g Ethylacetat und 0,06 g Dissopropylamin versetzt.3 kg of trichlorethylene were mixed with 0.66 g of 2,4-di-tert-butylphenol, 13.5 g of 2-methyl-2,3-epoxybutane, 6 g of diisobutylene, 8.4 g of ethyl acetate and 0.06 g of dissopropylamine.
Das derart stabilisierte Trichlorethen wurde dem beschriebenen DKH-Test unterworfen.The trichloroethene stabilized in this way was subjected to the described DKH test.
Der pH-Wert betrug nach 48 Stunden 9,5. Die Testflüssigkeit war farblos. Die Standzeit bis zum Erreichen der Aciditätsgrenze von 0,02 Gew.% HCI betrug 240 Stunden.The pH was 9.5 after 48 hours. The test liquid was colorless. The service life until the acidity limit of 0.02% by weight of HCl was reached was 240 hours.
Weitere Ergebnisse von Tests, die analog Beispiel 5 durchgeführt wurden, sind in der nachfolgenden Tabelle aufgeführt.
Es wurde die gemäß Beispiel 5 beschriebene Formulierung dem DKH-Test unterworfen, mit der Abänderung, daß anstatt 220 ppm 2.4-Ditert.Butylphenol
- a) 220 ppm 2.6-Ditert.-Butylphenol
- b) 220 ppm Anisol
- c) 220 ppm 2.6-Dimethyl-p-Kresol
- d) 220 ppm 4-tert.-Amylphenol
- e) 220 ppm 2.6-ditert.-butyl-p-kresol
- f) 220 ppm 4-tert.-Butylphenol eingesetzt wurden.
- a) 220 ppm of 2,6-di-tert-butylphenol
- b) 220 ppm anisole
- c) 220 ppm 2,6-dimethyl-p-cresol
- d) 220 ppm 4-tert-amylphenol
- e) 220 ppm of 2,6-di-tert-butyl-p-cresol
- f) 220 ppm of 4-tert-butylphenol were used.
Die Ergebnisse sind in der folgenden Tabelle zusammengestellt.
Die Ergebnisse gemäß den Beispielen 1 bis 11 und den Vergleichsbeispielen zeigen die ausgezeichnete Stabilität des erfindungsgemäßen Trichlorethens gegenüber Leichtmetallen, wie Aluminium, die sich in den extrem hohen Standzeiten wiederspiegelt. Die DKH-Tests beweisen ferner, daß das erfindungsgemäß stabilisierte Trichlorethen nicht nur als Entfettungsmittel geeignet ist, sondern ebenso den Anforderungen gerecht wird, die an Trichlorethen als Hilfsstoff für Lacke zu stellen sind. Die Vergleichsversuche veranschaulichen, daß beim Ersatz der erfindungsgemäß einzusetzenden phenolischen Komponenten gegen strukturell ähnliche phenolische Verbindungen die erfindungsgemäße Aufgabenstellung nicht erreicht wird.The results according to Examples 1 to 11 and the comparative examples show the excellent stability of the trichlorethylene according to the invention against light metals, such as aluminum, which is reflected in the extremely long service life. The DKH tests further prove that the trichloroethene stabilized according to the invention is not only suitable as a degreasing agent, but also meets the requirements which are to be placed on trichloroethene as an auxiliary for paints. The comparative experiments illustrate that when the phenolic components to be used according to the invention are replaced by structurally similar phenolic compounds, the task according to the invention is not achieved.
Claims (4)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT83101002T ATE53565T1 (en) | 1982-02-05 | 1983-02-03 | STABILIZED TRIHLORETHENE AND TRIHLORETHENE STABILIZING AGENT. |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE3203907 | 1982-02-05 | ||
DE19823203907 DE3203907A1 (en) | 1982-02-05 | 1982-02-05 | STABILIZED TRICHLORETHEN AND AGENT FOR STABILIZING TRICHLORETHEN |
Publications (3)
Publication Number | Publication Date |
---|---|
EP0085949A2 EP0085949A2 (en) | 1983-08-17 |
EP0085949A3 EP0085949A3 (en) | 1984-07-18 |
EP0085949B1 true EP0085949B1 (en) | 1990-06-13 |
Family
ID=6154849
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP83101002A Expired - Lifetime EP0085949B1 (en) | 1982-02-05 | 1983-02-03 | Stabilized trichloroethene and means for stabilizing trichloroethene |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP0085949B1 (en) |
JP (1) | JPS58135827A (en) |
AT (1) | ATE53565T1 (en) |
CA (1) | CA1175220A (en) |
DE (2) | DE3203907A1 (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU2001296504A1 (en) * | 2000-11-03 | 2002-05-15 | Dow Global Technologies Inc. | Stabilizer and solvent compositions |
KR100754721B1 (en) * | 2002-04-26 | 2007-09-03 | 삼성전자주식회사 | Apparatus and method for transmitting and receiving multiplexed data in an orthogonal frequency division multiplexing communication system |
FR2861390B1 (en) * | 2003-10-24 | 2006-01-21 | Arkema | STABILIZATION OF TRANS-1,2-DICHLORETHYLENE |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2797250A (en) * | 1954-05-13 | 1957-06-25 | Du Pont | Stabilization of chlorinated hydrocarbons |
NL97773C (en) * | 1957-11-09 | |||
DE1136695B (en) * | 1957-11-15 | 1962-09-20 | Sicedison Spa | Stabilizing trichlorethylene against decomposition |
FR1233249A (en) * | 1958-08-15 | 1960-10-12 | Canadian Ind | Stabilization of halohydrocarbons, in particular to prevent the decomposition of trichlorethylene |
GB932138A (en) * | 1960-10-27 | 1963-07-24 | Canadian Ind | Stabilization of halogenated hydrocarbons used as metal degreasing solvents |
JPS494448B1 (en) * | 1970-12-23 | 1974-02-01 |
-
1982
- 1982-02-05 DE DE19823203907 patent/DE3203907A1/en not_active Withdrawn
- 1982-11-09 CA CA000415213A patent/CA1175220A/en not_active Expired
-
1983
- 1983-02-01 JP JP58013819A patent/JPS58135827A/en active Granted
- 1983-02-03 AT AT83101002T patent/ATE53565T1/en not_active IP Right Cessation
- 1983-02-03 EP EP83101002A patent/EP0085949B1/en not_active Expired - Lifetime
- 1983-02-03 DE DE8383101002T patent/DE3381638D1/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
CA1175220A (en) | 1984-10-02 |
EP0085949A2 (en) | 1983-08-17 |
JPS58135827A (en) | 1983-08-12 |
EP0085949A3 (en) | 1984-07-18 |
DE3203907A1 (en) | 1983-08-11 |
JPS6121604B2 (en) | 1986-05-28 |
DE3381638D1 (en) | 1990-07-19 |
ATE53565T1 (en) | 1990-06-15 |
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