Fluorinated sulfonic acids and derivatives thereof

• US 4,014,926 A
• Filed: 12/19/1975
• Issued: 03/29/1977
• Est. Priority Date: 12/19/1975
• Status: Expired due to Term

• Current Assignee: Ciba-Geigy Corporation (Novartis Ag)
• Original Assignee: Ciba-Geigy Corporation (Novartis Ag)
• Inventors: Dear, Robert Ernest Arthur, Kleiner, Eduard Karl
• Primary Examiner(s): Thomas, Jr., James O.
• Assistant Examiner(s): Chan, Nicky
• Application Number:
  US05/642,271
• Time in Patent Office: 466 Days
• Field of Search: 260/513 N, 260/513 F
• US Class Current: 562/105
• CPC Class Codes: C07C 303/22 from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups
• CPC Class Codes: C07C 309/10 with the oxygen atom of at least one of the etherified hydroxy groups further bound to an acyclic carbon atom
• CPC Class Codes: C07C 309/14 containing amino groups bound to the carbon skeleton
• CPC Class Codes: C07C 309/15 the nitrogen atom of at least one of the amino groups being part of any of the groups , X being a hetero atom, Y being any atom
• CPC Class Codes: C07C 309/17 containing carboxyl groups bound to the carbon skeleton
• CPC Class Codes: C07C 309/20 of an acyclic unsaturated carbon skeleton

Abstract

The invention is directed to fluorinated alkylamido sulfonic acids and salts of the formula ##STR1## where R_f is straigt or branched chain perfluoroalkyl of 1 to 18 carbon atoms or perfluoroalkyl substituted by perfluoroalkoxy of 2 to 6 carbon atoms, R₁ is hydrogen or lower alkyl and each of R₂, R₄ and R₅ is individually hydrogen or a hydrocarbon radical, and R₆ is alkylene, alkylenethioalkylene, alkyleneoxyalkylene or alkyleneiminoalkylene with a secondary or tertiary nitrogen atom. R₃ is hydrogen, alkyl, aryl or pyridyl, M is hydrogen, a monovalent alkali metal, an alkaline earth metal, an organic base or ammonium, and n is an integer corresponding to the valency of M. Said compounds are prepared by a base catalyzed addition reaction of the thiol, R_f -R₆ SH, to an alkyenylamido sulfonic acid salt. The compounds are useful as surfactants and as levelling agents in floor polish formulations.

Claims

1. A compound of the formula ##STR6## wherein R_f is a straight or branched chain perfluoroalkyl of 1 to 18 carbon atoms or said perfluoroalkyl substituted by perfluoroalkoxy of 2 to 6 carbons,

R₁ is hydrogen or lower alkyl,

R₂, r₄ and R₅ are independently hydrogen or alkyl group of 1 to 12 carbons,

R₃ is hydrogen or alkyl of 1 to 12 carbons,

R₆ is a straight or branched chain alkylene of 1 to 12 carbons, and

M is hydrogen, a monovalent alkali metal or an alkaline earth metal, and

n is an integer corresponding to the valency of M.

2. A compound of claim 1 wherein R₁, R₄ and R₅ are hydrogen, R₂ and R₃ are methyl, R₆ is straight or branched chain alkylene and M is hydrogen, sodium, potassium, or magnesium.

3. The compound of claim 1 which is 2-methyl-2-(3-[1,1,2,2-tetrahydroperfluorooctylthio]propionamide)-1-propanesulfonic acid, sodium salt.

4. The compound of claim 1 which is 2-methyl-2-(3-[1,1,2,2-tetrahydroperfluorooctylthio]propionamide)-1-propanesulfonic acid, potassium salt.

5. A compound of claim 2 which is in the form of a free acid.

6. Compounds of claim 1 which are a mixture of 2-methyl-2-(3-[1,1,2,2-tetrahydroperfluoroalkylthio]propionamide)-1-propane-sulfonic acid, sodium salts, wherein the perfluoroalkyl moiety is a mixture of C₆ F₁₃, C₈ F₁₇ and C₁₀ F₂₁.

7. A compound of claim 1 which is a magnesium salt of 2-methyl-2-(3-[1,1,2,2-tetrahydroperfluorooctylthio]propionamide)-1-propanesulfonic acid.

8. A compound of claim 1 which is a sodium, potassium or magnesium salt of 2-methyl-2-(3-[1,1,2,2-tetrahydroperfluorododecylthio]propionamide)-1-propanesulfonic acid.

9. A compound of claim 1 which is a sodium, potassium or magnesium salt of 2-methyl-2-(3-[1,1,2,2-tetrahydroperfluorodecylthio] propionamide)-1-propanesulfonic acid.