EP0057925B1 - Fluorhaltige Alkylsulfobetaine, Verfahren zu deren Herstellung sowie deren Verwendung - Google Patents

Fluorhaltige Alkylsulfobetaine, Verfahren zu deren Herstellung sowie deren Verwendung Download PDF

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Publication number
EP0057925B1
EP0057925B1 EP82100856A EP82100856A EP0057925B1 EP 0057925 B1 EP0057925 B1 EP 0057925B1 EP 82100856 A EP82100856 A EP 82100856A EP 82100856 A EP82100856 A EP 82100856A EP 0057925 B1 EP0057925 B1 EP 0057925B1
Authority
EP
European Patent Office
Prior art keywords
alkylsulfobetaines
fluorine
general formula
amine
production
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
EP82100856A
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German (de)
English (en)
French (fr)
Other versions
EP0057925A1 (de
Inventor
Winfried Dr. Ehrl
Siegfried Jung
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hoechst AG
Original Assignee
Hoechst AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Hoechst AG filed Critical Hoechst AG
Publication of EP0057925A1 publication Critical patent/EP0057925A1/de
Application granted granted Critical
Publication of EP0057925B1 publication Critical patent/EP0057925B1/de
Expired legal-status Critical Current

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Classifications

    • 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 wherein R f , R 1 , R 2 , 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 according to the invention 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 2749329 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 2749330, is present.
  • the fluorinated alkylsulfobetaines according to the invention are absolutely compatible with cationic, nonionic and anionic surfactants.
  • the fluorine-containing alkylsulfobetaines according to the invention are also far superior in their hydrolysis stability to the known fluorine-containing alkylsulfatobetaines.
  • the fluorine-containing alkylsulfobetaines according to the invention are suitable because of their good compatibility speed with other non-ionic surfactants, such as oxalkylated phenols, as post-stabilizers in the production of polytetrafluoroethylene dispersions and dispersions of other fluoropolymers or copolymers, also as leveling agents for waxes, as cleaning enhancers in chemical cleaning and in particular because of their good surface-active activity as Mixture components in fire extinguishing agents.
  • non-ionic surfactants such as oxalkylated phenols
  • post-stabilizers in the production of polytetrafluoroethylene dispersions and dispersions of other fluoropolymers or copolymers, also as leveling agents for waxes, as cleaning enhancers in chemical cleaning and in particular because of their good surface-active activity as Mixture components 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. 1,715 g of the fluorine-containing amine referred to in Example 1 and 2,100 g of butyl glycol are heated to 60 ° C. and 425 g of propanesultone 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, 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.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Business, Economics & Management (AREA)
  • Emergency Management (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fire-Extinguishing Compositions (AREA)
EP82100856A 1981-02-11 1982-02-06 Fluorhaltige Alkylsulfobetaine, Verfahren zu deren Herstellung sowie deren Verwendung Expired EP0057925B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19813104766 DE3104766A1 (de) 1981-02-11 1981-02-11 "fluorhaltige alkylsulfobetaine, verfahren zu deren herstellung sowie deren verwendung"
DE3104766 1981-02-11

Publications (2)

Publication Number Publication Date
EP0057925A1 EP0057925A1 (de) 1982-08-18
EP0057925B1 true EP0057925B1 (de) 1984-08-15

Family

ID=6124529

Family Applications (1)

Application Number Title Priority Date Filing Date
EP82100856A Expired EP0057925B1 (de) 1981-02-11 1982-02-06 Fluorhaltige Alkylsulfobetaine, Verfahren zu deren Herstellung sowie deren Verwendung

Country Status (6)

Country Link
US (1) US4430272A (enrdf_load_stackoverflow)
EP (1) EP0057925B1 (enrdf_load_stackoverflow)
JP (1) JPS57150655A (enrdf_load_stackoverflow)
CA (1) CA1181418A (enrdf_load_stackoverflow)
DE (2) DE3104766A1 (enrdf_load_stackoverflow)
ES (1) ES509384A0 (enrdf_load_stackoverflow)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2575165B1 (fr) * 1984-12-26 1987-01-23 Atochem Telomeres fluores a groupements hydrophiles, leur procede de preparation et leur utilisation comme agents tensioactifs en milieu aqueux, notamment comme additifs aux emulseurs proteiniques anti-incendie
US4859349A (en) * 1987-10-09 1989-08-22 Ciba-Geigy Corporation Polysaccharide/perfluoroalkyl complexes
EP0671382B1 (de) * 1994-03-09 1998-10-14 Clariant GmbH Fluorhaltige Carboxylbetaine und Alkylsulfobetaine sowie deren Mischungen mit gesättigten Fluoralkyaminen
US5616273A (en) * 1994-08-11 1997-04-01 Dynax Corporation Synergistic surfactant compositions and fire fighting concentrates thereof
WO2004113391A2 (en) * 2003-06-23 2004-12-29 Neurochem (International) Limited Improved pharmaceutical drug candidates and methods for preparation thereof

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2764602A (en) 1954-04-21 1956-09-25 Minnesota Mining & Mfg Quaternary ammonium alkylperfluoroamides
US3535381A (en) 1967-05-22 1970-10-20 Pennwalt Corp Unsaturated fluoroalkyl amines and process for the preparation thereof
US3594411A (en) 1968-04-25 1971-07-20 Gulf Research Development Co Sulfobetaine detergents,and lubricants and cosmetics containing same
US3661776A (en) * 1970-08-24 1972-05-09 Minnesota Mining & Mfg Composition comprising a foam-forming fluoroaliphatic compound and a film-forming fluoroaliphatic compound
US3839425A (en) 1970-09-16 1974-10-01 Du Pont Perfluoroalkyletheramidoalkyl betaines and sulfobetaines
CA1077054A (en) 1975-04-02 1980-05-06 Eugene P. Gosselink Detergent compounds
US4000092A (en) 1975-04-02 1976-12-28 The Procter & Gamble Company Cleaning compositions
DE2658560C2 (de) * 1976-12-23 1979-02-01 Bayer Ag, 5090 Leverkusen Verfahren zur Herstellung von Tetraäthylammoniumperfluoralkylsulfonaten
DE2749329A1 (de) 1977-11-04 1979-05-10 Hoechst Ag Fluorhaltige alkyl-sulfato-betaine und verfahren zu deren herstellung
DE2749330C2 (de) 1977-11-04 1983-04-21 Hoechst Ag, 6230 Frankfurt Gemisch mit verbesserten oberflächenaktiven Eigenschaften
DD139577A1 (de) * 1978-11-09 1980-01-09 Bach Guenter Verfahren zur herstellung von n-sulfoalkyl-substituierten aminen
FR2453145B1 (enrdf_load_stackoverflow) * 1979-04-06 1981-03-27 Ugine Kuhlmann
US4283533A (en) 1979-11-09 1981-08-11 E. I. Du Pont De Nemours And Company N-type betaines of 2-hydroxy-1,1,2,3,3-pentahydroperfluoroalkylamines

Also Published As

Publication number Publication date
US4430272A (en) 1984-02-07
DE3260556D1 (en) 1984-09-20
JPH0150224B2 (enrdf_load_stackoverflow) 1989-10-27
JPS57150655A (en) 1982-09-17
ES8304929A1 (es) 1983-03-16
DE3104766A1 (de) 1982-09-02
EP0057925A1 (de) 1982-08-18
CA1181418A (en) 1985-01-22
ES509384A0 (es) 1983-03-16

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