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US4098811A Expired / Lapsed US ⏱️ 0.0 years remaining

Perfluoroalkylthioamido amine and ammonium compounds

Assignee: BASF Corp
•
Filing: 1976-12-02
•
Granted: 1978-07-04
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Expires: 1996-12-02
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Abstract

Abstract The perfluoroalkylthio amidoalkyl amine or ammonium compounds having the structures ##STR1## where R f is a perfluoroalkyl, R 1 is alkylene or alkylene oxy or amino alkylene, R 2 is hydrogen or alkyl, R 3 and R 4 are independently alkyl or together form a heterocyclic ring, R 5 is hydrogen or alkyl, R 6 is hydrogen, oxide, alkyl or substituted alkyl, E is alkylene or polyoxyalkylene, X is an anion, y is 1 or 2 and z is 0 or 1, which can be prepared by the base-catalyzed addition of a perfluoroalkylthiol to an α,β-unsaturated amide. These compounds are useful as surfactants.

Inventors

  • 👤 Robert A. Falk

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-06 10:03
CPC Classifications
C; C11; C11D; C11D1/00; C11D1/004

Claims Analysis

Total Claims: 10
Claim 1
Independent Claim 312 words
A compound having the structure ##STR5## wherein R f is straight or branched chain perfluoroalkyl of 1 to 18 carbon atoms or said perfluoroalkyl substituted by perfluoroalkoxy of 2 to 6 atoms; R 1 is branched or straight chain alkylene of 1 to 12 carbon atoms, alkylenethioalkylene of 2 to 12 carbon atoms, alkyleneoxyalkylene of 2 to 12 carbon atoms of alkyleneiminoalkylene of 2 to 12 carbon atoms where the nitrogen atom contains as a third substituent hydrogen of alkyl of 1 to 6 carbon atoms; R 2 is hydrogen or straight or branched chain alkyl of 1 to 6 carbon atoms; R 3 and R 4 each is independently straight or branched chain alkylyl of 1 to 22 carbon atoms; R 5 is hydrogen or straight or branched chain alkyl of 1 to 6 carbon atoms, or R 5 is a covalent bond if a heterocyclic ring formed between the two nitrogens as defined below; R 6 is hydrogen or straight or branched chain alkyl of 1 to 22 carbon atoms that may also contain 1 or 2 hydroxyl groups, a free carboxylic acid group, an anionic function selected from sulfonate, sulfate, or carboxylate, or oxygen; E is a straight or branched chain alkylene of 1 to 12 carbon atoms or alkylene polyoxyalkylene of formula C.sub.m H.sub.2m (OC.sub.k H.sub.2k).sub.r where m is an integer of 1 to 12 k is an integer of 2 to 6 r is an integer of 1 to 40; X is an anion selected from the group consisting of Br, Cl, I, acetate, phosphate, sulfate, methosulfate or ethosulfate; y is 1 to 2, depending on the valence of X, and z is 0 or 1, with the proviso that when z is 0, y is 1 and R 6 must be oxygen or an anionic function; if z is 1 R 6 may not be oxygen.
Claim 2
Dependent Claim 312 words
A compound having the structure ##STR5## wherein R f is straight or branched chain perfluoroalkyl of 1 to 18 carbon atoms or said perfluoroalkyl substituted by perfluoroalkoxy of 2 to 6 atoms; R 1 is branched or straight chain alkylene of 1 to 12 carbon atoms, alkylenethioalkylene of 2 to 12 carbon atoms, alkyleneoxyalkylene of 2 to 12 carbon atoms of alkyleneiminoalkylene of 2 to 12 carbon atoms where the nitrogen atom contains as a third substituent hydrogen of alkyl of 1 to 6 carbon atoms; R 2 is hydrogen or straight or branched chain alkyl of 1 to 6 carbon atoms; R 3 and R 4 each is independently straight or branched chain alkylyl of 1 to 22 carbon atoms; R 5 is hydrogen or straight or branched chain alkyl of 1 to 6 carbon atoms, or R 5 is a covalent bond if a heterocyclic ring formed between the two nitrogens as defined below; R 6 is hydrogen or straight or branched chain alkyl of 1 to 22 carbon atoms that may also contain 1 or 2 hydroxyl groups, a free carboxylic acid group, an anionic function selected from sulfonate, sulfate, or carboxylate, or oxygen; E is a straight or branched chain alkylene of 1 to 12 carbon atoms or alkylene polyoxyalkylene of formula C.sub.m H.sub.2m (OC.sub.k H.sub.2k).sub.r where m is an integer of 1 to 12 k is an integer of 2 to 6 r is an integer of 1 to 40; X is an anion selected from the group consisting of Br, Cl, I, acetate, phosphate, sulfate, methosulfate or ethosulfate; y is 1 to 2, depending on the valence of X, and z is 0 or 1, with the proviso that when z is 0, y is 1 and R 6 must be oxygen or an anionic function; if z is 1 R 6 may not be oxygen.
Claim 3
Dependent Claim 71 words
A compound of claim 1 wherein R 2 is hydrogen or methyl, R 5 is hydrogen R 6 is hydrogen or straight chain alkyl of 1 to 3 carbon atoms, and E is a straight chain alkylene of 2 or 3 carbon atoms or alkylene polyoxyalkylene where m is an integer of 1 to 4 k is an integer of 2 to 4 r is an integer of 1 to 20.
Claim 4
Dependent Claim 59 words
A compound of claim 1 selected from the group consisting of R.sub.f CH.sub.2 CH.sub.2 SCH.sub.2 CHCH.sub.3 CONH(CH.sub.2).sub.3 N(CH.sub.3).sub.2 (r.sub.f CH.sub.2 CH.sub.2 SCH.sub.2 CHCH.sub.3 CONH(CH.sub.2).sub.3 N(CH.sub.3).sub.2 C.sub.2 H.sub.5).sup.+ C.sub.2 H.sub.5 SO.sub.4.sup.- r.sub.f CH.sub.2 CH.sub.2 SCH.sub.2 CHCH.sub.3 CONH(CH.sub.2).sub.3 N.sup.+ (CH.sub.3).sub.2 CH.sub.2 CO.sub.2.sup.- where R f is perfluoroalkyl of 6 to 12 carbon atoms or perfluoroalkoxyperfluoroalkyl of 4 to 12 carbon atoms.
Claim 5
Dependent Claim 25 words
A compound of claim 3 wherein R f is (CF 3 ) 2 CFO(CH 2 CF 2 ) y where y is 1 to 6.
Claim 6
Dependent Claim 8 words
The compound of claim 1 which is N-(3-Dimethylaminopropyl)-2-methyl-3-(1,1,2-tetrahydroperfluorodecanethio)-propionamide.
Claim 7
Dependent Claim 10 words
The compound of claim 1 which is 3-[2-Methyl-3-(1,1,2,2-tetrahydroperfluorodecanethio)propionamido] propyltrimethylammonium iodide.
Claim 8
Dependent Claim 8 words
The compound of claim 1 which is N-(3-Dimethylamino)propyl-2-methyl-3-(1,1,2,2-tetrahydroperfluoroalkanethio)-propionamide.
Claim 9
Dependent Claim 10 words
The compound of claim 1 which is 3-[2-methyl-3-(1,1,2,2-tetrahydroperfluorodecanethio)-propionamido] propyltrimethylammonium iodide.
Claim 10
Dependent Claim 11 words
The compound of claim 1 which is 3-[2-methyl-3-(1,1,2,2-tetrahydroperfluorodecanethio)-propionamido] propyldimethylethylammonium ethyl sulfate.

References Cited (Backward Citations)

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US2764602A Cited
US3093146A Cited
US3547995A Cited
US3555089A Cited
US3697564A Cited
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USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1981-07-03 1982-01-02 1982-07-04 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1985-07-03 1986-01-02 1986-07-04 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1989-07-03 1990-01-02 1990-07-04 $7700.00 Window Closed / Lapsed

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