Skip to main content
Erschienen in:
Buchtitelbild

2012 | OriginalPaper | Buchkapitel

Chemistry, Properties, and Uses of Commercial Fluorinated Surfactants

verfasst von : Robert C. Buck, Peter M. Murphy, Martial Pabon

Erschienen in: Polyfluorinated Chemicals and Transformation Products

Verlag: Springer Berlin Heidelberg

Aktivieren Sie unsere intelligente Suche, um passende Fachinhalte oder Patente zu finden.

search-config
loading …

Abstract

Fluorinated surfactants have been commercially available since the 1950s. The first available were perfluoroalkyl sulfonic acids. The unique properties e.g., surface tension lowering in aqueous systems, high chemical and thermal stability of these acids and their derivatives when used at low concentrations resulted in their widespread use in industrial processes and consumer uses. The most common commercially produced perfluorinated surfactants are the perfluoroalkyl acids. Subsequently, additional commercial processes were developed for synthesis of a range of per- and poly-fluorinated surfactants whose unique properties make them largely irreplaceable in many applications. The widespread use and disposal and the high stability of the perfluoroalkyl acids, which do not breakdown readily either abiotically or biotically in the environment, has resulted in widespread presence of PFAAs in the environment. This caused commercial production to shift toward short chain alternatives and new fluorinated moieties such as the per- and polyfluorinated ethers. Clearly, there remains a need for fluorinated surfactants in many industries to obtain the beneficial performance properties of these substances that cannot be achieved with other types of surfactants. The aim of this chapter is to provide an overview of the commercially relevant chemistry, properties, and uses of commercial fluorinated surfactants.

Sie haben noch keine Lizenz? Dann Informieren Sie sich jetzt über unsere Produkte:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

  • über 102.000 Bücher
  • über 537 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Finance + Banking
  • Management + Führung
  • Marketing + Vertrieb
  • Maschinenbau + Werkstoffe
  • Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

  • über 67.000 Bücher
  • über 390 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Maschinenbau + Werkstoffe




 

Jetzt Wissensvorsprung sichern!

Literatur
1.
Zurück zum Zitat Kissa E (2001) Fluorinated surfactants and repellents. Surfactant Science Series 97. Marcel Dekker, New York Kissa E (2001) Fluorinated surfactants and repellents. Surfactant Science Series 97. Marcel Dekker, New York
2.
Zurück zum Zitat Kissa E (1994) Fluorinated surfactants: synthesis-properties-applications. Surfactant Science Series 50. Marcel Dekker, New York Kissa E (1994) Fluorinated surfactants: synthesis-properties-applications. Surfactant Science Series 50. Marcel Dekker, New York
3.
Zurück zum Zitat Taylor CK (1999) Fluorinated surfactants in practice. Annu Surfact Rev 2:271–316 Taylor CK (1999) Fluorinated surfactants in practice. Annu Surfact Rev 2:271–316
4.
Zurück zum Zitat Lehmler HJ (2009) Production of fluorinated surfactants by electrochemical fluorination. Surfact Sci Ser 142:301–321 Lehmler HJ (2009) Production of fluorinated surfactants by electrochemical fluorination. Surfact Sci Ser 142:301–321
5.
Zurück zum Zitat Lehmler HJ (2005) Synthesis of environmentally relevant fluorinated surfactants-a review. Chemosphere 58(11):1471–1496CrossRef Lehmler HJ (2005) Synthesis of environmentally relevant fluorinated surfactants-a review. Chemosphere 58(11):1471–1496CrossRef
6.
Zurück zum Zitat Schultz MM, Barofsky DF, Field JA (2003) Fluorinated alkyl surfactants. Environ Eng Sci 20(5):487–501CrossRef Schultz MM, Barofsky DF, Field JA (2003) Fluorinated alkyl surfactants. Environ Eng Sci 20(5):487–501CrossRef
7.
Zurück zum Zitat Pabon M, Corpart JM (2002) Fluorinated surfactants: synthesis, properties, effluent treatment. J Fluorine Chem 114(2):149–156CrossRef Pabon M, Corpart JM (2002) Fluorinated surfactants: synthesis, properties, effluent treatment. J Fluorine Chem 114(2):149–156CrossRef
8.
Zurück zum Zitat Smart BE (1994) Characteristics of C-F systems. In: Banks RE, Smart BE, Tatlow JC (eds) Organofluorine chemistry. Plenum Publishing, New York, NY Smart BE (1994) Characteristics of C-F systems. In: Banks RE, Smart BE, Tatlow JC (eds) Organofluorine chemistry. Plenum Publishing, New York, NY
9.
Zurück zum Zitat Banks RE, Smart BE, Tatlow JC (1994) Organofluorine chemistry: principles and commercial applications. Plenum, New York Banks RE, Smart BE, Tatlow JC (1994) Organofluorine chemistry: principles and commercial applications. Plenum, New York
10.
Zurück zum Zitat Simons JH (1949) Electrochemical process for the production of fluorocarbons. J Electrochem Soc 95:47–59CrossRef Simons JH (1949) Electrochemical process for the production of fluorocarbons. J Electrochem Soc 95:47–59CrossRef
11.
Zurück zum Zitat Holzapfel W (1966) Uses of fluorinated chemicals. Fette, Seifen, Anstrichmittel 68(10):837–842 Holzapfel W (1966) Uses of fluorinated chemicals. Fette, Seifen, Anstrichmittel 68(10):837–842
12.
Zurück zum Zitat Grajeck EJ, Peterson WH (1959) Fluorochemicals: the new idea in textiles. Am Dyest Rep 48(13):37–39 Grajeck EJ, Peterson WH (1959) Fluorochemicals: the new idea in textiles. Am Dyest Rep 48(13):37–39
13.
Zurück zum Zitat Brown RE (1963) Fluorochemicals and packaging. Pap Ind 45:205–208 Brown RE (1963) Fluorochemicals and packaging. Pap Ind 45:205–208
14.
Zurück zum Zitat Lau C et al (2007) Perfluoroalkyl acids: a review of monitoring and toxicological findings. Tox Sci 99(2):366–394CrossRef Lau C et al (2007) Perfluoroalkyl acids: a review of monitoring and toxicological findings. Tox Sci 99(2):366–394CrossRef
15.
Zurück zum Zitat Butt CM et al (2010) Levels and trends of poly- and perfluorinated compounds in the arctic environment. Sci Total Environ 408(15):2936–2965CrossRef Butt CM et al (2010) Levels and trends of poly- and perfluorinated compounds in the arctic environment. Sci Total Environ 408(15):2936–2965CrossRef
16.
Zurück zum Zitat Houde M et al (2006) Biological monitoring of polyfluoroalkyl substances: a review. Environ Sci Technol 40(11):3463–3473CrossRef Houde M et al (2006) Biological monitoring of polyfluoroalkyl substances: a review. Environ Sci Technol 40(11):3463–3473CrossRef
17.
Zurück zum Zitat Rao NS, Baker BE (1994) Textile finishes & fluorosurfactants (in Organofluorine chemistry. Principles and commercial applications). Plenum, New York, pp 321–336 Rao NS, Baker BE (1994) Textile finishes & fluorosurfactants (in Organofluorine chemistry. Principles and commercial applications). Plenum, New York, pp 321–336
18.
Zurück zum Zitat Sianesi DG (1996) Perfluoropolyether (PFPEs) from perfluoroolefin photooxidation. (In Organofluorine Chemistry. Principles and Commerical Applications.) Plenum, New York, pp 431–462 Sianesi DG (1996) Perfluoropolyether (PFPEs) from perfluoroolefin photooxidation. (In Organofluorine Chemistry. Principles and Commerical Applications.) Plenum, New York, pp 431–462
19.
Zurück zum Zitat Thomas RR (2006) Other types of surfactants – fluorinated surfactants. (In Chemistry and Technology of Surfactants). Blackwell, Oxford, UK, pp 227–235 Thomas RR (2006) Other types of surfactants – fluorinated surfactants. (In Chemistry and Technology of Surfactants). Blackwell, Oxford, UK, pp 227–235
20.
Zurück zum Zitat M Company (1999) Fluorochemical use, distribution and release overview. US EPA Admin Record AR226-0550 M Company (1999) Fluorochemical use, distribution and release overview. US EPA Admin Record AR226-0550
21.
Zurück zum Zitat M Company (1995) 3M The Leader in Electrofluorination (3M Company Technical Bulletin) St. Paul, MN M Company (1995) 3M The Leader in Electrofluorination (3M Company Technical Bulletin) St. Paul, MN
22.
Zurück zum Zitat Arsenault G et al (2008) Some issues relating to the use of perfluorooctanesulfonate (PFOS) samples as reference standards. Chemosphere 70(4):616–625CrossRef Arsenault G et al (2008) Some issues relating to the use of perfluorooctanesulfonate (PFOS) samples as reference standards. Chemosphere 70(4):616–625CrossRef
23.
Zurück zum Zitat M Company (2000) Re: Phase-out Plan for POSF-based Products. US EPA Admin Record AR226-0588 M Company (2000) Re: Phase-out Plan for POSF-based Products. US EPA Admin Record AR226-0588
24.
Zurück zum Zitat Ritter SK (2010) Fluorochemicals go short. Chem Eng News 88(5):12–17CrossRef Ritter SK (2010) Fluorochemicals go short. Chem Eng News 88(5):12–17CrossRef
25.
Zurück zum Zitat Savu PM, Etienne SA (2001) Fluorochemical sulfonamide surfactants. EU Appl 2,001,027. 3M Innovative Properties Company, USA Savu PM, Etienne SA (2001) Fluorochemical sulfonamide surfactants. EU Appl 2,001,027. 3M Innovative Properties Company, USA
26.
Zurück zum Zitat Dams RJ et al. (2006) Compositions of monomeric surfactants. US Appl 2,006,148,671. 3M Innovative Properties Company, USA Dams RJ et al. (2006) Compositions of monomeric surfactants. US Appl 2,006,148,671. 3M Innovative Properties Company, USA
27.
Zurück zum Zitat Terrazas MS et al. (2006) Fluorochemical polymeric surfactants. US Appl 2,006,149,012. 3M Innovative Properties Company, USA Terrazas MS et al. (2006) Fluorochemical polymeric surfactants. US Appl 2,006,149,012. 3M Innovative Properties Company, USA
28.
Zurück zum Zitat Moore GGI, Dams RJ (2008) Fluorinated surfactants and method of making the same. World Appl 2,008,045,999,200,8. 3M Innovative Properties Company, USA Moore GGI, Dams RJ (2008) Fluorinated surfactants and method of making the same. World Appl 2,008,045,999,200,8. 3M Innovative Properties Company, USA
29.
Zurück zum Zitat Prevedouros K et al (2006) Sources, fate and transport of perfluorocarboxylates. Environ Sci Technol 40(1):32–44CrossRef Prevedouros K et al (2006) Sources, fate and transport of perfluorocarboxylates. Environ Sci Technol 40(1):32–44CrossRef
30.
Zurück zum Zitat Grottenmuller R et al. (2002) Process for the preparation of perfluorocarboxylic acids from perfluoroalkyl iodides and oxygen. EU Patent 1,172,350. Clariant, GmbH Grottenmuller R et al. (2002) Process for the preparation of perfluorocarboxylic acids from perfluoroalkyl iodides and oxygen. EU Patent 1,172,350. Clariant, GmbH
31.
Zurück zum Zitat Kasai PH (1995) Perfluoropolyethers with acid end groups: amphiphilicity and emulsification. J Appl Polym Sci 57(7):797–809CrossRef Kasai PH (1995) Perfluoropolyethers with acid end groups: amphiphilicity and emulsification. J Appl Polym Sci 57(7):797–809CrossRef
32.
Zurück zum Zitat Millauer H, Schwertfeger W, Siegemund G (1985) Hexafluoropropene oxide – a key compound of organofluorine chemistry. Angew Chem 97(3):164–182CrossRef Millauer H, Schwertfeger W, Siegemund G (1985) Hexafluoropropene oxide – a key compound of organofluorine chemistry. Angew Chem 97(3):164–182CrossRef
33.
Zurück zum Zitat Audenaert FA, Dams RJ (2006) Fluorinated polyether copolymer surfactants. World Appl 2,006,112,2. 3M Innovative Properties Company, USA Audenaert FA, Dams RJ (2006) Fluorinated polyether copolymer surfactants. World Appl 2,006,112,2. 3M Innovative Properties Company, USA
34.
Zurück zum Zitat Audenaert FA, Dams RJ, Tan LS (2005) Mixture of fluorinated polyethers, liquid compositions and surfactant use. US Appl 2,005,096,244. 3M Innovative Properties Company, USA Audenaert FA, Dams RJ, Tan LS (2005) Mixture of fluorinated polyethers, liquid compositions and surfactant use. US Appl 2,005,096,244. 3M Innovative Properties Company, USA
35.
Zurück zum Zitat Dams RJ et al. (2009) Preparation of fluorinated ether compounds used to reduce surface tension, make foam, and treat surfaces. World Appl 2,009,071,5. 3M Innovative Properties Company, USA Dams RJ et al. (2009) Preparation of fluorinated ether compounds used to reduce surface tension, make foam, and treat surfaces. World Appl 2,009,071,5. 3M Innovative Properties Company, USA
37.
Zurück zum Zitat Visca M et al. (2003) Aqueous fluoropolymer dispersions containing bifunctional fluorinated surfactants with reduced environmental impact. World Appl 2,003,279,9. Solvay Solexis S.p.A., Italy Visca M et al. (2003) Aqueous fluoropolymer dispersions containing bifunctional fluorinated surfactants with reduced environmental impact. World Appl 2,003,279,9. Solvay Solexis S.p.A., Italy
38.
Zurück zum Zitat Higuchi S et al. (2007) Aqueous polytetrafluoroethylene emulsions for fine powders and porous materials with good paste extrusion molding property. World Appl 2,007,046,345. Asahi Glass Co., Ltd., Japan Higuchi S et al. (2007) Aqueous polytetrafluoroethylene emulsions for fine powders and porous materials with good paste extrusion molding property. World Appl 2,007,046,345. Asahi Glass Co., Ltd., Japan
39.
Zurück zum Zitat Hintzer K et al. (2007) Method of making fluoropolymer dispersion. US Appl 2,007,015,864. 3M Innovative Properties Company, USA Hintzer K et al. (2007) Method of making fluoropolymer dispersion. US Appl 2,007,015,864. 3M Innovative Properties Company, USA
40.
Zurück zum Zitat Ishikawa T, Tsuda N, Yamamoto Y (2009) Preparation of fluoro ether carboxylic acids useful for surfactants and aqueous dispersion used thereof. US Appl 2,009,176,942. Daikin Industries, Ltd., Japan Ishikawa T, Tsuda N, Yamamoto Y (2009) Preparation of fluoro ether carboxylic acids useful for surfactants and aqueous dispersion used thereof. US Appl 2,009,176,942. Daikin Industries, Ltd., Japan
41.
Zurück zum Zitat Gordon SC (2011) Toxicological evaluation of ammonium 4,8-dioxa-3 H-perfluorononanoate, a new emulsifier to replace ammonium perfluorooctanoate in fluoropolymer manufacturing. Reg Tox Pharmacol 59(1):64–80 Gordon SC (2011) Toxicological evaluation of ammonium 4,8-dioxa-3 H-perfluorononanoate, a new emulsifier to replace ammonium perfluorooctanoate in fluoropolymer manufacturing. Reg Tox Pharmacol 59(1):64–80
42.
Zurück zum Zitat Dams RJ et al. (2002) Compositions comprising fluorinated polyether silanes for rendering substrates oil and water repellent. World Appl 2,002,030,848. 3M Innovative Properties Company, USA Dams RJ et al. (2002) Compositions comprising fluorinated polyether silanes for rendering substrates oil and water repellent. World Appl 2,002,030,848. 3M Innovative Properties Company, USA
43.
Zurück zum Zitat Dams RJ, Martin SJ, Flynn RM (2005) Fluorinated polyether isocyanate derived silane compositions with good oil and water repellency and stain resistance. US Appl 2,005,054,804. 3M Innovative Properties Company, USA Dams RJ, Martin SJ, Flynn RM (2005) Fluorinated polyether isocyanate derived silane compositions with good oil and water repellency and stain resistance. US Appl 2,005,054,804. 3M Innovative Properties Company, USA
44.
Zurück zum Zitat Jinks PA, Dams RJ (2009) Medicinal inhalation devices comprising multifunctional polyfluoropolyether silane applied to surface. World Appl 2,009,061,902. 3M Innovative Properties Company, USA Jinks PA, Dams RJ (2009) Medicinal inhalation devices comprising multifunctional polyfluoropolyether silane applied to surface. World Appl 2,009,061,902. 3M Innovative Properties Company, USA
45.
Zurück zum Zitat Moore GGI et al. (2003) Coating composition containing fluoro-containing polyether silane polycondensate with durable repellency to water, oil and stain. World Appl 2,003,040,209. 3M Innovative Properties Company, USA Moore GGI et al. (2003) Coating composition containing fluoro-containing polyether silane polycondensate with durable repellency to water, oil and stain. World Appl 2,003,040,209. 3M Innovative Properties Company, USA
46.
Zurück zum Zitat Kausch CM et al (2003) Surface tension and adsorption properties of a series of bola-amphiphilic poly(fluorooxetane)s. Langmuir 19(18):7182–7187CrossRef Kausch CM et al (2003) Surface tension and adsorption properties of a series of bola-amphiphilic poly(fluorooxetane)s. Langmuir 19(18):7182–7187CrossRef
47.
Zurück zum Zitat Kausch CM et al (2003) Interfacial rheological properties of a series of bolaamphiphilic poly(fluorooxetane)s. Langmuir 19(18):7354–7361CrossRef Kausch CM et al (2003) Interfacial rheological properties of a series of bolaamphiphilic poly(fluorooxetane)s. Langmuir 19(18):7354–7361CrossRef
48.
Zurück zum Zitat Kausch CM et al (2002) Synthesis, characterization, and unusual surface activity of a series of novel architecture, water-dispersible poly(fluorooxetane)s. Langmuir 18(15):5933–5938CrossRef Kausch CM et al (2002) Synthesis, characterization, and unusual surface activity of a series of novel architecture, water-dispersible poly(fluorooxetane)s. Langmuir 18(15):5933–5938CrossRef
49.
Zurück zum Zitat Dams R (1993) Fluorochemical surfactants for hostile environments. Spec Chem 13(1):4–6 Dams R (1993) Fluorochemical surfactants for hostile environments. Spec Chem 13(1):4–6
50.
Zurück zum Zitat Shinoda K, Hato M, Hayashi T (1972) The physicochemical properties of aqueous solutions of fluorinated surfactants. J Phys Chem 76(6):909–914CrossRef Shinoda K, Hato M, Hayashi T (1972) The physicochemical properties of aqueous solutions of fluorinated surfactants. J Phys Chem 76(6):909–914CrossRef
51.
Zurück zum Zitat Kunieda H, Shinoda K (1976) Krafft points, critical micelle concentrations, surface tension, and solubilizing power of aqueous solutions of fluorinated surfactants. J Phys Chem 80(22):2468–2470CrossRef Kunieda H, Shinoda K (1976) Krafft points, critical micelle concentrations, surface tension, and solubilizing power of aqueous solutions of fluorinated surfactants. J Phys Chem 80(22):2468–2470CrossRef
52.
Zurück zum Zitat Ngo THV et al (2010) Synthesis and comparative behaviour study of fluorocarbon and hydrocarbon cationic surfactants in aqueous media. J Fluorine Chem 131(6):704–708CrossRef Ngo THV et al (2010) Synthesis and comparative behaviour study of fluorocarbon and hydrocarbon cationic surfactants in aqueous media. J Fluorine Chem 131(6):704–708CrossRef
53.
Zurück zum Zitat Sharma SC, Shrestha LK, Aramaki K (2007) Interfacial properties of aqueous nonionic fluorocarbon surfactant solutions. J Dispersion Sci Technol 28(4):577–581CrossRef Sharma SC, Shrestha LK, Aramaki K (2007) Interfacial properties of aqueous nonionic fluorocarbon surfactant solutions. J Dispersion Sci Technol 28(4):577–581CrossRef
54.
Zurück zum Zitat Sagisaka M et al (2001) Effects of fluoroalkyl chain length and added moles of oxyethylene on aggregate formation of branched-tail fluorinated anionic surfactants. Colloids Surf A 183–185:749–755CrossRef Sagisaka M et al (2001) Effects of fluoroalkyl chain length and added moles of oxyethylene on aggregate formation of branched-tail fluorinated anionic surfactants. Colloids Surf A 183–185:749–755CrossRef
55.
Zurück zum Zitat Burdon J et al. (1957) Fluorinated sulphonic acids. Part I. Perfluoromethane-,octane-, and -decanesulfonic acids and their simple derivatives. J Chem Soc:2574–2578 Burdon J et al. (1957) Fluorinated sulphonic acids. Part I. Perfluoromethane-,octane-, and -decanesulfonic acids and their simple derivatives. J Chem Soc:2574–2578
56.
Zurück zum Zitat Segal L et al (1958) Oil- and water-repellent treatments for cotton with fluorochemicals. Tex Res J 28:233–241CrossRef Segal L et al (1958) Oil- and water-repellent treatments for cotton with fluorochemicals. Tex Res J 28:233–241CrossRef
57.
Zurück zum Zitat Philips FJ, Segal L, Loeb L (1957) Application of fluorochemicals to cotton fabrics to obtain oil- and water-repellent surfaces. Tex Res J 27:369–378CrossRef Philips FJ, Segal L, Loeb L (1957) Application of fluorochemicals to cotton fabrics to obtain oil- and water-repellent surfaces. Tex Res J 27:369–378CrossRef
58.
Zurück zum Zitat Kauck EA, Diesslin AR (1951) Some properties of perfluorocarboxylic acids. Ind Eng Chem 43(10):2332–2334CrossRef Kauck EA, Diesslin AR (1951) Some properties of perfluorocarboxylic acids. Ind Eng Chem 43(10):2332–2334CrossRef
59.
Zurück zum Zitat Fiala R (1982) Use of extinguishing agents in aircraft post-crash fire-fighting/rescue. AGARD Lect Ser 123:8/1–8/27 Fiala R (1982) Use of extinguishing agents in aircraft post-crash fire-fighting/rescue. AGARD Lect Ser 123:8/1–8/27
60.
Zurück zum Zitat Tuve RL, Jablonski EJ (1966) Perfluoro compounds as foams for hydrocarbon fires. US 3,258,423. United States Dept. of the Navy Tuve RL, Jablonski EJ (1966) Perfluoro compounds as foams for hydrocarbon fires. US 3,258,423. United States Dept. of the Navy
61.
Zurück zum Zitat Clarke M (1992) AFFFs – Fighting Aircraft Fires. Aircraft Engineer November 12–13 Clarke M (1992) AFFFs – Fighting Aircraft Fires. Aircraft Engineer November 12–13
62.
Zurück zum Zitat Moody CA, Field JA (2000) Perfluorinated surfactants and the environmental implications of their use in fire-fighting foams. Environ Sci Technol 34(18):3864–3870CrossRef Moody CA, Field JA (2000) Perfluorinated surfactants and the environmental implications of their use in fire-fighting foams. Environ Sci Technol 34(18):3864–3870CrossRef
63.
Zurück zum Zitat Pabon M, Corpart JM (1999) Fluorinated surfactants in fire fighting foams. Actualite Chimique 7:3–9 Pabon M, Corpart JM (1999) Fluorinated surfactants in fire fighting foams. Actualite Chimique 7:3–9
64.
Zurück zum Zitat Falk RA (1984) Perfluoroalkyl amphoteric compounds. EU Patent 1,152,51. Ciba-Geigy A-G, Switzerland Falk RA (1984) Perfluoroalkyl amphoteric compounds. EU Patent 1,152,51. Ciba-Geigy A-G, Switzerland
65.
Zurück zum Zitat Bertocchio R, Foulletier L (1971) Beta -[2-[2-(Perfluoroalkyl)ethylsulfonylamino]ethyl]dimethylammoniopropionates. DE 2120868. Ugine Kuhlmann, Germany Bertocchio R, Foulletier L (1971) Beta -[2-[2-(Perfluoroalkyl)ethylsulfonylamino]ethyl]dimethylammoniopropionates. DE 2120868. Ugine Kuhlmann, Germany
66.
Zurück zum Zitat Harkins WD, Feldman A (2009) Films. The spreading of liquids and the spreading coefficient. J Am Chem Soc 44:2665–2685CrossRef Harkins WD, Feldman A (2009) Films. The spreading of liquids and the spreading coefficient. J Am Chem Soc 44:2665–2685CrossRef
67.
Zurück zum Zitat Cortina T (2009) Aircraft rescue and firefighting requires the best foam available: AFFF. Asia-Pacific Fire Magazine June: 25–28 Cortina T (2009) Aircraft rescue and firefighting requires the best foam available: AFFF. Asia-Pacific Fire Magazine June: 25–28
68.
Zurück zum Zitat Figueredo RCR and Sabadini FALReE (1999) Science of foams – application in fire-fighting. Quim. Nova, 22(1) 126–130 Figueredo RCR and Sabadini FALReE (1999) Science of foams – application in fire-fighting. Quim. Nova, 22(1) 126–130
69.
Zurück zum Zitat Murphy PM, Hewat T (2008) Fluorosurfactants in enhanced oil recovery. Open Petroleum Eng J 1:58–61CrossRef Murphy PM, Hewat T (2008) Fluorosurfactants in enhanced oil recovery. Open Petroleum Eng J 1:58–61CrossRef
70.
Zurück zum Zitat M Company (1992) Fluorad® well stimulation additives. St. Paul, MN M Company (1992) Fluorad® well stimulation additives. St. Paul, MN
71.
Zurück zum Zitat Clark HB, Pike MT, Rengel GL (1982) Water-soluble fluorochemical surfactant well stimulation additives. J Pet Technol 34(7):1565–1569 Clark HB, Pike MT, Rengel GL (1982) Water-soluble fluorochemical surfactant well stimulation additives. J Pet Technol 34(7):1565–1569
72.
Zurück zum Zitat Clark HB (1980) Use of fluorochemical surfactants in nonaqueous stimulation fluids. J Pet Technol 32(10):1695–1697 Clark HB (1980) Use of fluorochemical surfactants in nonaqueous stimulation fluids. J Pet Technol 32(10):1695–1697
73.
Zurück zum Zitat Baran JR et al. (2009) Methods for treating hydrocarbon-bearing formations with fluorinated polymer compositions. World Appl 2,009,085,904. 3M Innovative Properties Company, USA Baran JR et al. (2009) Methods for treating hydrocarbon-bearing formations with fluorinated polymer compositions. World Appl 2,009,085,904. 3M Innovative Properties Company, USA
74.
Zurück zum Zitat Baran JR, Terrazas MS, Dams RJ (2009) Fluorinated anionic surfactants and fluoropolymers in well treatment fluids for petroleum recovery. World Appl 2,009,085,899,200,9. 3M Innovative Properties Company, USA Baran JR, Terrazas MS, Dams RJ (2009) Fluorinated anionic surfactants and fluoropolymers in well treatment fluids for petroleum recovery. World Appl 2,009,085,899,200,9. 3M Innovative Properties Company, USA
75.
Zurück zum Zitat Dams RJ, Baran JR, Wu YK (2010) Method of contacting hydrocarbon-bearing formations with fluorinated phosphate and phosphonate compositions. World Appl 2,010,080,353,201,0. 3M Innovative Properties Company, USA Dams RJ, Baran JR, Wu YK (2010) Method of contacting hydrocarbon-bearing formations with fluorinated phosphate and phosphonate compositions. World Appl 2,010,080,353,201,0. 3M Innovative Properties Company, USA
76.
Zurück zum Zitat Dams RJ (2010) Method of contacting hydrocarbon-bearing formations with fluorinated ether compositions. World Appl 2,010,080,473,201,0. 3M Innovative Properties Company, USA Dams RJ (2010) Method of contacting hydrocarbon-bearing formations with fluorinated ether compositions. World Appl 2,010,080,473,201,0. 3M Innovative Properties Company, USA
77.
Zurück zum Zitat Moore GGI, Dams RJ, Baran JR (2009) Preparation of fluorinated polymers for use in treating hydrocarbon-bearing formations. World Appl 2,009,085,936. 3M Innovative Properties Company, USA Moore GGI, Dams RJ, Baran JR (2009) Preparation of fluorinated polymers for use in treating hydrocarbon-bearing formations. World Appl 2,009,085,936. 3M Innovative Properties Company, USA
78.
Zurück zum Zitat Pope GA et al. (2009) Use of fluorocarbon surfactants to improve the productivity of gas and gas condensate wells. US Appl 2,009,062,155. Board of Regents, The University of Texas System, USA; 3M Innovative Properties Company, USA Pope GA et al. (2009) Use of fluorocarbon surfactants to improve the productivity of gas and gas condensate wells. US Appl 2,009,062,155. Board of Regents, The University of Texas System, USA; 3M Innovative Properties Company, USA
79.
Zurück zum Zitat Linert JG, Chasman JN (1993) Applications of fluorochemical surfactants in high-solids and water-borne coatings. Proc. Water-Borne, Higher-Solids, Powder Coat Symp:462–476 Linert JG, Chasman JN (1993) Applications of fluorochemical surfactants in high-solids and water-borne coatings. Proc. Water-Borne, Higher-Solids, Powder Coat Symp:462–476
80.
Zurück zum Zitat De Witte J, Piessens G, Dams R (1995) Fluorochemical intermediates, surfactants and their use in coatings. Surf Coat Int 78(2):63–64 De Witte J, Piessens G, Dams R (1995) Fluorochemical intermediates, surfactants and their use in coatings. Surf Coat Int 78(2):63–64
81.
Zurück zum Zitat Witte JD, Piessens G, Dams R (1994) Fluorochemical intermediates, surfactants and their use in coatings. Fluorine Coat., Int. Conf., Paper 17 Witte JD, Piessens G, Dams R (1994) Fluorochemical intermediates, surfactants and their use in coatings. Fluorine Coat., Int. Conf., Paper 17
82.
Zurück zum Zitat Linert JG, Chasman JN (1993) Applications of fluorochemical surfactants in high-solids and water-borne coatings. Am Paint Coatings J. December 20:37–43 Linert JG, Chasman JN (1993) Applications of fluorochemical surfactants in high-solids and water-borne coatings. Am Paint Coatings J. December 20:37–43
83.
Zurück zum Zitat Moore GGI et al. (2007) Compositions of fluorochemical surfactants and their use in coatings. US Appl 2,007,049,646. 3M Innovative Properties Co., USA Moore GGI et al. (2007) Compositions of fluorochemical surfactants and their use in coatings. US Appl 2,007,049,646. 3M Innovative Properties Co., USA
84.
Zurück zum Zitat Pike MT (1972) Fluorochemical surfactants for nonaqueous systems. Paint Varn Prod 62(3):27–32 Pike MT (1972) Fluorochemical surfactants for nonaqueous systems. Paint Varn Prod 62(3):27–32
85.
Zurück zum Zitat Meng J (2006) Novel applications for fluorosurfactants in low VOC coatings. FutureCoat Proc:051/1–051/6 Meng J (2006) Novel applications for fluorosurfactants in low VOC coatings. FutureCoat Proc:051/1–051/6
86.
Zurück zum Zitat Dams R (1995) Fluorochemical surfactants for inks. Pitture Vernici Eur 71(13):30–2 Dams R (1995) Fluorochemical surfactants for inks. Pitture Vernici Eur 71(13):30–2
87.
Zurück zum Zitat Ma Z et al. (2001) Color ink jet ink composition with fluorosurfactant. US6,436,180,200,1. Hewlett-Packard Co., USA Ma Z et al. (2001) Color ink jet ink composition with fluorosurfactant. US6,436,180,200,1. Hewlett-Packard Co., USA
88.
Zurück zum Zitat Wills RGA, Watt-Smith MJ, Walsh FC (2009) The use of fluorocarbon surfactants to improve the manufacture of PEM fuel cell electrodes. Fuel Cells 9(2):148–156CrossRef Wills RGA, Watt-Smith MJ, Walsh FC (2009) The use of fluorocarbon surfactants to improve the manufacture of PEM fuel cell electrodes. Fuel Cells 9(2):148–156CrossRef
89.
Zurück zum Zitat Mansouri HR et al (2007) Fluorinated polyether additives to improve the performance of urea-formaldehyde adhesives for wood panels. J Appl Polym Sci 106(3):1683–1688CrossRef Mansouri HR et al (2007) Fluorinated polyether additives to improve the performance of urea-formaldehyde adhesives for wood panels. J Appl Polym Sci 106(3):1683–1688CrossRef
90.
Zurück zum Zitat Bultman DA, Pike MT (1981) The use of fluorochemical surfactants in floor polish. Chem Times Trends 4(1):41–4 Bultman DA, Pike MT (1981) The use of fluorochemical surfactants in floor polish. Chem Times Trends 4(1):41–4
91.
Zurück zum Zitat Dams RJ, Terrazas MS (2008) Aqueous compositions of fluorinated surfactants and coating/cleaning use on surfaces and reducing surface tension of liquids. World Appl 2,008,147,796. 3M Innovative Properties Company, USA Dams RJ, Terrazas MS (2008) Aqueous compositions of fluorinated surfactants and coating/cleaning use on surfaces and reducing surface tension of liquids. World Appl 2,008,147,796. 3M Innovative Properties Company, USA
92.
Zurück zum Zitat Leach MJ, Niwata Y (1998) Cleaning composition comprising fluoro-surfactants. EU Patent 866115. Unilever PLC, UK Leach MJ, Niwata Y (1998) Cleaning composition comprising fluoro-surfactants. EU Patent 866115. Unilever PLC, UK
93.
Zurück zum Zitat Anich AT, Sierakowski MJ (1995) Mist suppressant for solvent extraction metal electrowinning. World Appl 9530783. Minnesota Mining and Manufacturing Co., USA Anich AT, Sierakowski MJ (1995) Mist suppressant for solvent extraction metal electrowinning. World Appl 9530783. Minnesota Mining and Manufacturing Co., USA
94.
Zurück zum Zitat Savu PM, Lamanna WM, Parent MJ (2005) Fluorinated sulfonamide surfactants for aqueous cleaning solutions. US Appl 2,005,197,273. 3M Innovative Properties Company, USA Savu PM, Lamanna WM, Parent MJ (2005) Fluorinated sulfonamide surfactants for aqueous cleaning solutions. US Appl 2,005,197,273. 3M Innovative Properties Company, USA
95.
Zurück zum Zitat Rengel GL, Perrault EW, Rambosek GM (1966) Fluorochemical sizing agent for wet-end addition. Tappi 49(2):76A–79A Rengel GL, Perrault EW, Rambosek GM (1966) Fluorochemical sizing agent for wet-end addition. Tappi 49(2):76A–79A
96.
Zurück zum Zitat Olson CC et al. (2005) Fluorochemical sizing. Sizing Pap. (3rd edn):151–178 Olson CC et al. (2005) Fluorochemical sizing. Sizing Pap. (3rd edn):151–178
97.
Zurück zum Zitat Schwartz C (1981) Oil resistance utilizing fluorochemicals. Sizing, Short Course Notes Tech. Assoc. Pulp Pap Ind:71–5 Schwartz C (1981) Oil resistance utilizing fluorochemicals. Sizing, Short Course Notes Tech. Assoc. Pulp Pap Ind:71–5
98.
Zurück zum Zitat Chad RM (1982) Use of fluorochemicals in reprographic paper grades. Coat Conf Proc:47–55 Chad RM (1982) Use of fluorochemicals in reprographic paper grades. Coat Conf Proc:47–55
99.
Zurück zum Zitat Allison MC (1984) Application of fluorochemicals in paper surface coatings. Pap Technol Ind 25(1):13–16 Allison MC (1984) Application of fluorochemicals in paper surface coatings. Pap Technol Ind 25(1):13–16
100.
Zurück zum Zitat Giatti R (1996) New fluorochemicals for greaseproof papers. Pap Technol 37(9):49–54 Giatti R (1996) New fluorochemicals for greaseproof papers. Pap Technol 37(9):49–54
101.
Zurück zum Zitat Deisenroth E et al (1998) The designing of a new grease repellent fluorochemical for the paper industry. Surf Coat Int 81(9):440–447CrossRef Deisenroth E et al (1998) The designing of a new grease repellent fluorochemical for the paper industry. Surf Coat Int 81(9):440–447CrossRef
102.
Zurück zum Zitat Liu Y, Jho C (2004) Sizing with fluorochemicals: internal application. J Pulp Pap Sci 30(2):45–49 Liu Y, Jho C (2004) Sizing with fluorochemicals: internal application. J Pulp Pap Sci 30(2):45–49
103.
Zurück zum Zitat Orem MW, Andrews RR (2004) Fluorinated surfactants in overcoat compositions and elements containing same. US Appl 2,004,137,385. Eastman Kodak Company, USA Orem MW, Andrews RR (2004) Fluorinated surfactants in overcoat compositions and elements containing same. US Appl 2,004,137,385. Eastman Kodak Company, USA
104.
Zurück zum Zitat Dams RJ, Arren DHC, Brandon M (1996) Fluoropolymers and fluorochemical surface active agents for improving the antistatic behavior of materials and light-sensitive material having improved antistatic behavior. EU Appl 1,994,071,819,96. Minnesota Mining and Manufacturing Co., USA Dams RJ, Arren DHC, Brandon M (1996) Fluoropolymers and fluorochemical surface active agents for improving the antistatic behavior of materials and light-sensitive material having improved antistatic behavior. EU Appl 1,994,071,819,96. Minnesota Mining and Manufacturing Co., USA
105.
Zurück zum Zitat D’Eon JC et al (2009) Perfluorinated phosphonic acids in Canadian surface waters and wastewater treatment plant effluent: discovery of a new class of perfluorinated acids. Environ Toxicol Chem 28(10):2101–2107CrossRef D’Eon JC et al (2009) Perfluorinated phosphonic acids in Canadian surface waters and wastewater treatment plant effluent: discovery of a new class of perfluorinated acids. Environ Toxicol Chem 28(10):2101–2107CrossRef
106.
Zurück zum Zitat U.S. Environmental Protection Agency (2006) Meeting with Registrant on Perfluorinated Chemical (Masurf-FS-780, Fluowet PL 80-B, and Fluowet PL-80) Use as Inerts. Letter from the Office of Pollution Prevention and Toxics to the Office of Pesticide Programs. U.S. EPA Public Docket AR226-3804 U.S. Environmental Protection Agency (2006) Meeting with Registrant on Perfluorinated Chemical (Masurf-FS-780, Fluowet PL 80-B, and Fluowet PL-80) Use as Inerts. Letter from the Office of Pollution Prevention and Toxics to the Office of Pesticide Programs. U.S. EPA Public Docket AR226-3804
107.
Zurück zum Zitat U.S. Federal Register (2006) Inert Ingredient; Revocation of the Tolerance Exemption for Mono- and Bis-(1 H, 1 H, 2 H, 2 H-perfluoroalkyl) Phosphates Where the Alkyl Group is Even Numbered and in the C6-C12 Range. 71(153):45408–45411 U.S. Federal Register (2006) Inert Ingredient; Revocation of the Tolerance Exemption for Mono- and Bis-(1 H, 1 H, 2 H, 2 H-perfluoroalkyl) Phosphates Where the Alkyl Group is Even Numbered and in the C6-C12 Range. 71(153):45408–45411
Metadaten
Titel
Chemistry, Properties, and Uses of Commercial Fluorinated Surfactants
verfasst von
Robert C. Buck
Peter M. Murphy
Martial Pabon
Copyright-Jahr
2012
Verlag
Springer Berlin Heidelberg
DOI
https://doi.org/10.1007/978-3-642-21872-9_1