EP0057925A1 - Fluorine containing alkylsulfobetaines, process for their production and their use - Google Patents

Fluorine containing alkylsulfobetaines, process for their production and their use Download PDF

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EP0057925A1
EP0057925A1 EP82100856A EP82100856A EP0057925A1 EP 0057925 A1 EP0057925 A1 EP 0057925A1 EP 82100856 A EP82100856 A EP 82100856A EP 82100856 A EP82100856 A EP 82100856A EP 0057925 A1 EP0057925 A1 EP 0057925A1
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Prior art keywords
fluorine
alkylsulfobetaines
carbon atoms
general formula
amine
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French (fr)
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EP0057925B1 (en
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Winfried Dr. Ehrl
Siegfried Jung
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Hoechst AG
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Hoechst AG
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    • A—HUMAN NECESSITIES
    • A62—LIFE-SAVING; FIRE-FIGHTING
    • A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
    • A62D1/00—Fire-extinguishing compositions; Use of chemical substances in extinguishing fires
    • A62D1/0071—Foams
    • A62D1/0085—Foams containing perfluoroalkyl-terminated surfactant

Definitions

  • the invention relates to fluorine-containing alkylsulfobetaines, a process for their preparation and their use.
  • R f is a perfluoroalkyl radical with 3 to 16 carbon atoms
  • R 1 and R 2 which may be the same or different, alkyl radicals or hydroxyalkyl radicals with 1 to 4 carbon atoms
  • a is zero or 1
  • R 1 and R 2 identical or different, in these compounds are preferably an alkyl radical or a hydroxyalkyl radical having 1 to 2 carbon atoms and a is 1.
  • the present invention also encompasses a process for the preparation of the fluorine-containing alkylsulfobetaines defined above, which is characterized in that a fluorine-containing amine of the general formula
  • R f , R 1 , R z , a and b have the meaning defined above, with a sulton of the general formula wherein c has the meaning defined above, in an organic solvent to react.
  • the fluorinated amines used as the starting compound are known; they can be prepared, for example, by methods such as those described in US Pat. No. 3,257,407, US Pat. No. 3,535,381, DE-AS 16 68 794, and DE-OS 17 68 939 or DE-OS 21 41 542 are described.
  • Propane sultone or butane sultone are used as sulfoalkylating agents.
  • the reaction is carried out in an organic solvent which must be inert to the reactants. Suitable solvents for the reaction are, for example, methanol, ethanol, butyl glycol, butyl diglycol or acetone.
  • the appropriate reaction temperature is in the range from 50 to 100 ° C., the reaction takes place under essentially pressure-free conditions. At these temperatures, the sulfoalkylation lasts between 1 and 10 hours. The sultons should not be used beyond the stoichiometrically required proportion, since they are toxic.
  • the fluorinated alkylsulfobetaines can be obtained in solid form by distilling off the solvent. However, the solution of the products in the organic solvent obtained from the sulfoalkylation can also be used for many applications.
  • the fluorine-containing alkylsulfobetaines of the formula defined above are distinguished by a considerable reduction in the surface tension (water / air) and in particular by a high surface-active activity at the interface between water and immiscible organic liquids, in particular hydrocarbons.
  • the fluorinated alkyl sulfatobetaines known from DE-OS 27 49 329 result in such a lowering of the interfacial tension water / immiscible organic liquid at the low application concentrations which occur in practice only when a synergistic second component, such as a fluorinated alkylammonium monoalkyl sulfate, is described in DE-OS 27 49 330, is present.
  • the fluorinated alkylsulfobetaines according to the invention are absolutely compatible with cationic, nonionic and anionic surfactants.
  • the fluorine-containing alkyl sulfobetaines according to the invention are also far superior in their hydrolysis stability to the known fluorine-containing alkyl sulfatobetaines.
  • the fluorine-containing alkylsulfobetaines according to the invention are suitable because of their good compatibility with other non-ionic surfactants, such as, for example, oxalkylated phenols, as post-stabilizers in the production of polytetrafluoroethylene dispersions and dispersions of other fluoropolymers or copolymers, furthermore as leveling agents for waxes, as cleaning enhancers in the chemical industry Cleaning and especially because of their good surface-active effectiveness as a mixture component in fire extinguishing agents.
  • non-ionic surfactants such as, for example, oxalkylated phenols
  • post-stabilizers in the production of polytetrafluoroethylene dispersions and dispersions of other fluoropolymers or copolymers, furthermore as leveling agents for waxes, as cleaning enhancers in the chemical industry Cleaning and especially because of their good surface-active effectiveness as a mixture component in fire extinguishing agents.
  • Example 2 The procedure is as in Example 1, but acetone is used instead of the ethanol. After filtration and drying, 298 g, corresponding to a yield of 97% of theory, of the compound of Example 1 are obtained. The determination of the amine number shows that the product still contains 0.5% free amine.
  • Example 2 The procedure is as in Example 1, but butyl glycol is used as the solvent instead of ethanol. 1715 g of the fluorine-containing amine referred to in Example 1 and 2100 g of butyl glycol are heated to 60 ° C. and 425 g of propane sultone are added dropwise at this temperature. The mixture is then stirred at 80 ° C for 3 hours. To obtain a 40% solution, 1000 g of water are added. The amine number determination shows that 0.4% free amine is still present.
  • Example 3 64 g (N-1,1,2-trihydroperfluoroalkenyl-2) -N-dimethylamine (in which the R f radical has the meaning given in Example 1), 18.2 g propane sultone and 83 ml Butylglycol implemented.
  • the sulfobetaine of the formula obtained contains 1.0% free amine according to the amine number.
  • the constitution of the sulfobetaines obtained was confirmed by their 1 H-NMR spectra and IR spectra.

Abstract

Es werden fluorhaltigeAlkylsulfobetaine der allgemeinen Formel <IMAGE> worin Rf einen Perfluoralkylrest mit 3 bis 16 C-Atomen, R1 und R2, die gleich oder verschieden sein können, Alkylreste oder Hydroxyalkylreste mit 1 bis 4 C-Atomen bedeuten, a Null oder 1 ist, b den Wert 1 für a = 1 und die Werte 1 bis 4 für a = 0 annimmt, sowie c 3 oder 4 ist, beschrieben. Diese werden hergestellt durch Umsetzung der entsprechenden fluorhaltigen Amine mit Propan- oder Butansulton in organischen Lösungsmitteln. Die Verbindungen zeichnen sich insbesondere durch hohe grenzflächenaktive Wirksamkeit an der Grenzfläche von Wasser zu nicht mischbaren organischen Flüssigkeiten und Verträglichkeit mit anderen Tensiden aus. Sie eignen sich als Nachbehandlungsmittel (Hilfsdispergatoren) für Dispersionen von Fluorpolymeren und als Mischungskomponenten in Feuerlöschmitteln.There are fluorine-containing alkylsulfobetaines of the general formula <IMAGE> where Rf is a perfluoroalkyl radical having 3 to 16 carbon atoms, R1 and R2, which may be the same or different, alkyl radicals or hydroxyalkyl radicals having 1 to 4 carbon atoms, a is zero or 1, b assumes the value 1 for a = 1 and the values 1 to 4 for a = 0, and c is 3 or 4. These are produced by reacting the corresponding fluorine-containing amines with propane or butane sultone in organic solvents. The compounds are distinguished in particular by high surface-active activity at the interface between water and immiscible organic liquids and compatibility with other surfactants. They are suitable as post-treatment agents (auxiliary dispersants) for dispersions of fluoropolymers and as mixture components in fire extinguishing agents.

Description

Die Erfindung betrifft fluorhaltige Alkylsulfobetaine, ein Verfahren zu deren Herstellung sowie deren Verwendung.The invention relates to fluorine-containing alkylsulfobetaines, a process for their preparation and their use.

Die neuen Verbindungen haben die allgemeine Formel

Figure imgb0001
worin Rf einen Perfluoralkylrest mit 3 bis 16 C-Atomen, R1 und R2, die gleich oder verschieden sein können, Alkylreste oder Hydroxyalkylreste mit 1 bis 4 C-Atomen bedeuten, a Null oder 1 ist, b den Wert 1 für a = 1 und die Werte 1 bis 4 für a = 0 annimmt, sowie c 3 oder 4 ist.The new compounds have the general formula
Figure imgb0001
 wherein R f is a perfluoroalkyl radical with 3 to 16 carbon atoms, R 1 and R 2 , which may be the same or different, alkyl radicals or hydroxyalkyl radicals with 1 to 4 carbon atoms, a is zero or 1, b is 1 for a = 1 and assumes the values 1 to 4 for a = 0, and c is 3 or 4.

Vorzugsweise bedeutet R1 und R2, gleich oder verschieden,in diesen Verbindungen einen Alkylrest oder einen Hydroxyalkylrest mit 1 bis 2 C-Atomen und a den Wert 1.R 1 and R 2 , identical or different, in these compounds are preferably an alkyl radical or a hydroxyalkyl radical having 1 to 2 carbon atoms and a is 1.

Die vorliegende Erfindung umfaßt auch ein Verfahren zur Herstellung der oben definierten fluorhaltigen Alkylsulfobetaine, das dadurch gekennzeichnet ist, daß man ein fluorhaltiges Amin der allgemeinen Formel

Figure imgb0002
The present invention also encompasses a process for the preparation of the fluorine-containing alkylsulfobetaines defined above, which is characterized in that a fluorine-containing amine of the general formula
Figure imgb0002

worin Rf, R1, Rz, a und b die oben definierte Bedeutung haben, mit einem Sulton der allgemeinen Formel

Figure imgb0003
worin c die oben definierte Bedeutung hat, in einem -organischen Lösungsmittel zur Reaktion bringt.wherein R f , R 1 , R z , a and b have the meaning defined above, with a sulton of the general formula
Figure imgb0003
 wherein c has the meaning defined above, in an organic solvent to react.

Die als Ausgangsverbindung eingesetzten fluorierten Amine sind bekannt, sie können beispielsweise nach Methoden hergestellt werden, wie sie in der US-PS 3 257 407, der US-PS 3 535 381, der DE-AS 16 68 794, der DE-OS 17 68 939 oder der DE-OS 21 41 542 beschrieben sind. Als Sulfoalkylierungsmittel dienen Propansulton oder Butansulton. Die Reaktion wird in einem organischen Lösungsmittel vorgenommen, das gegenüber - den Reaktionspartnern inert sein muß. Geeignete Lösungmittel für die Umsetzung sind beispielsweise Methanol, Ethanol, Butylglykol, Butyldiglykol oder Aceton. Die zweckmäßige Reaktionstemperatur liegt im Bereich von 50 bis 100 °C, die Reaktion erfolgt unter im wesentlichen drucklosen Bedingungen. Bei diesen Temperaturen dauert die Sulfoalkylierung zwischen 1 und 10 Stunden. Die Sultone sollten zweckmäßig nicht über den stöchiometrisch erforderlichen Anteil hinaus eingesetzt werden, da sie toxisch sind. Nach Beendigung der Sulfoalkylierung können die fluorierten Alkylsulfobetaine durch Abdestillieren des Lösungsmittels in fester Form gewonnen werden. Für viele Anwendungszwecke kann jedoch auch die aus der Sulfoalkylierung anfallende Lösung der Produkte im organischen Lösungsmittel eingesetzt werden.The fluorinated amines used as the starting compound are known; they can be prepared, for example, by methods such as those described in US Pat. No. 3,257,407, US Pat. No. 3,535,381, DE-AS 16 68 794, and DE-OS 17 68 939 or DE-OS 21 41 542 are described. Propane sultone or butane sultone are used as sulfoalkylating agents. The reaction is carried out in an organic solvent which must be inert to the reactants. Suitable solvents for the reaction are, for example, methanol, ethanol, butyl glycol, butyl diglycol or acetone. The appropriate reaction temperature is in the range from 50 to 100 ° C., the reaction takes place under essentially pressure-free conditions. At these temperatures, the sulfoalkylation lasts between 1 and 10 hours. The sultons should not be used beyond the stoichiometrically required proportion, since they are toxic. After the sulfoalkylation has ended, the fluorinated alkylsulfobetaines can be obtained in solid form by distilling off the solvent. However, the solution of the products in the organic solvent obtained from the sulfoalkylation can also be used for many applications.

Die Sulfoalkylierung kann auch mit Gemischen von fluorierten Aminen (a = Null und 1) durchgeführt werden.The sulfoalkylation can also be carried out with mixtures of fluorinated amines (a = zero and 1).

Die erfindungsgemäßen fluorhaltigen Alkylsulfobetaine der oben definierten Formel zeichnen sich durch eine beträchtliche Erniedrigung der Oberflächenspannung (Wasser/ Luft) und insbesondere durch eine hohe grenzflächenaktive Wirksamkeit an der Grenzfläche von Wasser zu nicht-mischbaren organischen Flüssigkeiten, insbesondere Kohlenwasserstoffen, aus. Die aus der DE-OS 27 49 329 bekannten fluorierten Alkylsulfatobetaine ergeben eine solche Erniedrigung der Grenzflächenspannung Wasser/nicht-mischbare organische Flüssigkeit bei den in der Praxis vorkommenden niedrigen Anwendungskonzentrationen nur dann, wenn eine synergistisch wirkende Zweitkomponente, wie beispielsweise ein fluoriertes Alkylammoniummonoalkylsulfat, beschrieben in der DE-OS 27 49 330, zugegen ist. Solche quaternären Ammoniumsalze sind jedoch mit anionischen Tensiden, wie sie beispielsweise in Feuerlöschmitteln vorkommen, nicht verträglich, hingegen sind die erfindungsgemäßen fluorierten Alkylsulfobetaine absolut verträglich mit kationischen, nicht-ionischen und anionischen Tensiden. Schließlich sind die erfindungsgemäßen fluorhaltigen Alkylsulfobetaine den bekannten fluorhaltigen Alkylsulfatobetainen auch in ihrer Hydrolysestabilität weit überlegen.The fluorine-containing alkylsulfobetaines of the formula defined above are distinguished by a considerable reduction in the surface tension (water / air) and in particular by a high surface-active activity at the interface between water and immiscible organic liquids, in particular hydrocarbons. The fluorinated alkyl sulfatobetaines known from DE-OS 27 49 329 result in such a lowering of the interfacial tension water / immiscible organic liquid at the low application concentrations which occur in practice only when a synergistic second component, such as a fluorinated alkylammonium monoalkyl sulfate, is described in DE-OS 27 49 330, is present. However, such quaternary ammonium salts are not compatible with anionic surfactants, such as those found in fire extinguishing agents, on the other hand, the fluorinated alkylsulfobetaines according to the invention are absolutely compatible with cationic, nonionic and anionic surfactants. Finally, the fluorine-containing alkyl sulfobetaines according to the invention are also far superior in their hydrolysis stability to the known fluorine-containing alkyl sulfatobetaines.

Die erfindungsgemäßen fluorhaltigen Alkylsulfobetaine eignen sich wegen ihrer guten Verträglichkeit mit anderen nicht-ionischen Tensiden, wie beispielsweise oxalkylierten Phenolen, als Nachstabilisierungsmittel bei der Herstellung von Polytetrafluorethylen-Dispersionen und Dispersionen anderer Fluorpolymerer oder -copolymerer, ferner als Verlaufmittel für Wachse, als Reinigungsverstärker in der chemischen Reinigung sowie insbesondere wegen ihrer guten grenzflächenaktiven Wirksamkeit als Mischungskomponenten in Feuerlöschmitteln.The fluorine-containing alkylsulfobetaines according to the invention are suitable because of their good compatibility with other non-ionic surfactants, such as, for example, oxalkylated phenols, as post-stabilizers in the production of polytetrafluoroethylene dispersions and dispersions of other fluoropolymers or copolymers, furthermore as leveling agents for waxes, as cleaning enhancers in the chemical industry Cleaning and especially because of their good surface-active effectiveness as a mixture component in fire extinguishing agents.

Nachfolgende Beispiele sollen die Erfindung näher erläuternThe following examples are intended to explain the invention in more detail

Beispiel 1 .Example 1 .

245 g (N-1,1,2-Trihydroperfluoralkenyl-2)-N-methylethanolamin, dessen perfluorierter Alkylrest Rf aus einem Gemisch verschiedener perfluorierter Alkyle folgender Zusammensetzung besteht:

  • 41 Gew.-% C5F11-
  • 40 Gew.-% C7F15-
  • 14 Gew.-% C9F19-
  • 5 Gew.-% C11F23-,
werden in 300 ml Ethanol gelöst,und unter Rühren wird bei 70 °C 60 g Propansulton zugetropft. Dann wird 3 Stunden unter Rückfluß gekocht und anschließend das Lösungsmittel abdestilliert. Man schlämmt das Produkt mit Aceton auf und filtriert den ausgefallenen Feststoff ab. Hierbei werden 210 g Produkt der Formel
Figure imgb0004
isoliert, was einer Ausbeute von 69 % der Theorie entspricht. Die Aminzahlbestimmung ergibt den Wert 0.245 g (N-1,1,2-trihydroperfluoroalkenyl-2) -N-methylethanolamine, the perfluorinated alkyl radical R f of which consists of a mixture of different perfluorinated alkyls of the following composition:
  • 41% by weight C 5 F 11 -
  • 40% by weight C 7 F 15 -
  • 14% by weight C 9 F 19 -
  • 5% by weight C 11 F 23 -,
are dissolved in 300 ml of ethanol, and 60 g of propane sultone are added dropwise at 70 ° C. while stirring. The mixture is then boiled under reflux for 3 hours and then the solvent is distilled off. The product is slurried with acetone and the precipitated solid is filtered off. 210 g of product of the formula
Figure imgb0004
 isolated, which corresponds to a yield of 69% of theory. The amine number determination gives the value 0.

Beispiel 2Example 2

Es wird gearbeitet wie in Beispiel 1, jedoch wird anstelle des Ethanols Aceton verwendet. Nach Filtration und Trocknung werden 298 g, entsprechend einer Ausbeute von 97 % der Theorie, der Verbindung des Beispiels 1 erhalten. Die Bestimmung der Aminzahl ergibt, daß das Produkt noch 0,5 % freies Amin enthält.The procedure is as in Example 1, but acetone is used instead of the ethanol. After filtration and drying, 298 g, corresponding to a yield of 97% of theory, of the compound of Example 1 are obtained. The determination of the amine number shows that the product still contains 0.5% free amine.

Beispiel 3Example 3

Es wird gearbeitet wie in Beispiel 1, jedoch wird anstelle von Ethanol Butylglykol als Lösungsmittel verwendet. 1715 g des in Beispiel 1 bezeichneten fluorhaltigen Amins und 2100 g Butylglykol werden auf 60 °C erwärmt und bei dieser Temperatur wird 425 g Propansulton zugetropft. Anschließ-end wird 3 Stunden bei 80 °C nachgerührt. Um eine 40 %ige Lösung zu erhalten, werden 1000 g Wasser zugesetzt. Die Aminzahlbestimmung ergibt, daß noch 0,4 % freies Amin vorhanden ist.The procedure is as in Example 1, but butyl glycol is used as the solvent instead of ethanol. 1715 g of the fluorine-containing amine referred to in Example 1 and 2100 g of butyl glycol are heated to 60 ° C. and 425 g of propane sultone are added dropwise at this temperature. The mixture is then stirred at 80 ° C for 3 hours. To obtain a 40% solution, 1000 g of water are added. The amine number determination shows that 0.4% free amine is still present.

Beispiel 4Example 4

Es werden gemäß der Arbeitsweise des Beispiels 3 40 g eines (N-1,1,2-Trihydroperfluoroctenyl-2)-N-methylethanol- amins, 12 g Propansulton und 52 ml Butylglykol umgesetzt. Das erhaltene Sulfobetain der Formel

Figure imgb0005
enthält laut Aminzahl noch 1,0 % freies Amin.40 g of a (N-1,1,2-trihydroperfluoroctenyl-2) -N-methylethanolamine, 12 g of propane sultone and 52 ml of butyl glycol are reacted according to the procedure of Example 3. The sulfobetaine of the formula obtained
Figure imgb0005
 contains 1.0% free amine according to the amine number.

Beispiel 5Example 5

Gemäß der Arbeitsweise des Beispiels 3 werden 51 g (N-1,1,2-Trihydroperfluordecenyl-2)-N-methylethanolamin, 12 g Propansulton und 63 ml Butylglykol umgesetzt. Das erhaltene Sulfobetain der Formel

Figure imgb0006
enthält laut Aminzahl noch 0,7 % freies Amin.According to the procedure of Example 3, 51 g (N-1,1,2-trihydroperfluorodecenyl-2) -N-methylethanolamine, 12 g propane sultone and 63 ml butyl glycol are reacted. The sulfobetaine of the formula obtained
Figure imgb0006
 contains 0.7% free amine according to the amine number.

Beispiel 6Example 6

Gemäß der Arbeitsweise des Beispiels 3 werden 60,5 g (N-1,1,2-Trihydroperfluordodecenyl-2)-N-methylethanolamin, 12 g Propansulton und 73 ml Butylglykol umgesetzt. Das erhaltene Sulfobetain der Formel

Figure imgb0007
enthält laut Aminzahl noch 1,5 % freies Amin.According to the procedure of Example 3, 60.5 g (N-1,1,2-trihydroperfluorododecenyl-2) -N-methylethanolamine, 12 g propane sultone and 73 ml butyl glycol are reacted. The sulfobetaine of the formula obtained
Figure imgb0007
 contains 1.5% free amine according to the amine number.

Beispiel 7Example 7

Gemäß der Arbeitsweise des Beispiels 3 werden 64 g (N-1,1,2-Trihydroperfluoralkenyl-2)-N-dimethylamin (worin der Rf-Rest die in Beispiel 1 genannte Bedeutung hat), 18,2 g Propansulton und 83 ml Butylglykol umgesetzt. Das erhaltene Sulfobetain der Formel

Figure imgb0008
enthält laut Aminzahl noch 1,0 % freies Amin.According to the procedure of Example 3, 64 g (N-1,1,2-trihydroperfluoroalkenyl-2) -N-dimethylamine (in which the R f radical has the meaning given in Example 1), 18.2 g propane sultone and 83 ml Butylglycol implemented. The sulfobetaine of the formula obtained
Figure imgb0008
 contains 1.0% free amine according to the amine number.

Beispiel 8Example 8

239,5 g (N-1,1,2-Trihydroperfluoralkenyl-2)-N-methylethanolamin (worin der Rf-Rest die in Beispiel 1 genannte Bedeutung hat) werden zusammen mit 68 g 1,4-Butansulton und 200 ml Methanol 4 Stunden zum Sieden erhitzt. Nach Abziehen des Lösungsmittels verbleibt als fester Rückstand ein Sulfobetain der Formel

Figure imgb0009
mit einer Aminzahl von 2,8. Dies entspricht einem Gehalt an 4 % freiem Amin.239.5 g (N-1,1,2-trihydroperfluoroalkenyl-2) -N-methylethanolamine (in which the R f radical has the meaning given in Example 1) together with 68 g of 1,4-butanesultone and 200 ml of methanol Heated to boiling for 4 hours. After the solvent has been stripped off, a sulfobetaine of the formula remains as a solid residue
Figure imgb0009
 with an amine number of 2.8. This corresponds to a 4% free amine content.

Beispiel 9Example 9

Gemäß der Arbeitsweise von Beispiel 3 werden 66 g N-1,1,2,2-Tetrahydroperfluoralkyl-N,N-dimethylamin der Formel

Figure imgb0010
worin der Rest Rf folgende Zusammensetzung aufweist:

  • 41 Gew.-% C6F13-
  • 40 Gew.-% C8F17-
  • 14 Gew.-% C10F21-
  • 5 Gew.-% C12F25-,
und 18,2 g Propansulton in 83 ml Butylglykol umgesetzt. Das erhaltene Sulfobetain der Formel
Figure imgb0011
enthält laut Aminzahl noch 1,5 % freies Amin.According to the procedure of Example 3, 66 g of N-1,1,2,2-tetrahydroperfluoroalkyl-N, N-dimethylamine of the formula
Figure imgb0010
 wherein the radical R f has the following composition:
  • 41% by weight C 6 F 13 -
  • 40% by weight C 8 F 17 -
  • 14% by weight C 10 F 21 -
  • 5% by weight C 12 F 25 -,
and 18.2 g of propane sultone in 83 ml of butyl glycol. The sulfobetaine of the formula obtained
Figure imgb0011
 contains 1.5% free amine according to the amine number.

Die Konstitution der erhaltenen Sulfobetaine wurde durch deren 1H-NMR-Spektren und IR-Spektren gesichert.The constitution of the sulfobetaines obtained was confirmed by their 1 H-NMR spectra and IR spectra.

Die folgende Tabelle zeigt die überlegenen Eigenschaften von wäßrigen Lösungen der erfindungsgemäßen Sulfobetaine hinsichtlich der Oberflächenspannung und der Grenz- flächenspannung gegen Cyclohexan im Vergleich zu fluorhaltigen Sulfatobetainen und zwei anerkannt guten Handelsprodukten, die gleichfalls Fluortenside sind und quaternäre Ammoniumgruppen enthalten:

Figure imgb0012
The following table shows the superior properties of aqueous solutions of sulfobetaines invention in terms of the surface tension and the G renz- surface tension against cyclohexane as compared to fluorine-containing Sulfatobetainen and two recognized good commercial products, which are also fluoro surfactants and contain quaternary ammonium groups:
Figure imgb0012

Claims (3)

1. Fluorhaltige Alkylsulfobetaine der allgemeinen Formel
Figure imgb0013
worin Rf einen Perfluoralkylrest mit 3 bis 16 C-Atomen, R1 und R2, die gleich oder verschieden sein können, Alkylreste oder Hydroxyalkylreste mit 1 bis 4 C-Atomen, bedeuten, a Null oder 1 ist, b den Wert 1 für a = 1 und die Werte 1 bis 4 für a = 0 annimmt, sowie c 3 oder 4 ist.1. Fluorine-containing alkylsulfobetaines of the general formula
Figure imgb0013
 wherein R f is a perfluoroalkyl radical with 3 to 16 carbon atoms, R 1 and R 2 , which may be the same or different, alkyl radicals or hydroxyalkyl radicals with 1 to 4 carbon atoms, a is zero or 1, b is 1 for a = 1 and assumes the values 1 to 4 for a = 0, and c is 3 or 4. 2. Verfahren zur Herstellung von fluorhaltigen Alkylsulfobetainen gemäß Anspruch 1, dadurch gekennzeichnet, daß man ein fluorhaltiges Amin der allgemeinen Formel
Figure imgb0014
worin Rf, R1, R2, a und b die in Anspruch 1 definierte Bedeutung haben, mit einem Sulton der allgemeinen Formel
Figure imgb0015
worin c die in Anspruch 1 definierte Bedeutung hat, in einem organischen Lösungsmittel zur Reaktion bringt.2. A process for the preparation of fluorine-containing alkylsulfobetaines according to claim 1, characterized in that a fluorine-containing amine of the general formula
Figure imgb0014
 wherein R f , R 1 , R 2 , a and b have the meaning defined in claim 1, with a sulton of the general formula
Figure imgb0015
 wherein c has the meaning defined in claim 1, in an organic solvent to react. 3. Verwendung der fluorhaltigen Alkylsulfobetaine gemäß Anspruch 1 als Komponente in Feuerlöschmitteln.3. Use of the fluorine-containing alkylsulfobetaines according to claim 1 as a component in fire extinguishing agents.
EP82100856A 1981-02-11 1982-02-06 Fluorine containing alkylsulfobetaines, process for their production and their use Expired EP0057925B1 (en)

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DE19813104766 DE3104766A1 (en) 1981-02-11 1981-02-11 "FLUORINE ALKYLSULFOBETAINE, METHOD FOR THE PRODUCTION AND USE THEREOF"
DE3104766 1981-02-11

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EP0057925A1 true EP0057925A1 (en) 1982-08-18
EP0057925B1 EP0057925B1 (en) 1984-08-15

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US (1) US4430272A (en)
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CA (1) CA1181418A (en)
DE (2) DE3104766A1 (en)
ES (1) ES509384A0 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
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US5648528A (en) * 1994-03-09 1997-07-15 Hoechst Aktiengesellschaft Saturated fluoroalkylamines and their derivatives, and mixtures thereof

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DE3260556D1 (en) 1984-09-20
JPS57150655A (en) 1982-09-17
ES8304929A1 (en) 1983-03-16
DE3104766A1 (en) 1982-09-02
CA1181418A (en) 1985-01-22
EP0057925B1 (en) 1984-08-15
US4430272A (en) 1984-02-07
JPH0150224B2 (en) 1989-10-27
ES509384A0 (en) 1983-03-16

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