IP Library Granted Patent US 8,263,800
Granted Patent B2
US 8,263,800 · App. 12/165,798 · Granted Sep 11, 2012

Partially fluorinated sulfonated surfactants

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Quick Facts
Patent No.
US 8,263,800
App. No.
12/165,798
Granted
Sep 11, 2012
Kind
B2
Abstract

The present invention comprises a compound comprising Formula 1A, 1B, or 1C (R a —O—CO—) 2 X  Formula 1A R a —O—CO—X—CO—O—(CH 2 CH 2 )R f   Formula 1B R a —O—CO—X—CO—O—R  Formula 1C wherein R a is the group R f (CH 2 CF 2 ) d —(C g H 2g )—; R f OCF 2 CF 2 —(C g H 2g )—; R f OCFHCF 2 O(CH 2 CH 2 O) v —(C g H 2g )—; R f OCFHCF 2 O(C w H 2w ); R f OCF(CF 3 )CONH—(C g H 2g ); or R f (CH 2 ) h [(CF 2 CF 2 ) i (CH 2 CH 2 ) j ] k ; R f is C c F (2c+1) ; d is 1 to about 3; g is 1 to 4; v is 1 to about 4; w is from about 3 to about 12; h is 1 to about 6; i, j, and k are each independently 1, 2, or 3, or a mixture thereof; provided that the total number of carbon atoms in group (vi) is from about 8 to about 22; X is a linear or branched difunctional alkyl sulfonate group —C e H (2e−1) (SO 3 M)-, wherein e is 2 or 3; M is a monovalent cation selected from the group consisting of hydrogen, ammonium, alkali metal, or alkaline earth metal; R is H or a linear or branched alkyl group C b H (2b+1) —; and b is from 1 to about 18.

Claims (37)

1. A compound of Formula 1A, 1B, or 1C

(R a —O—CO—) 2 X  Formula 1A

R a —O—CO—X—CO—O—(CH 2 CH 2 )R f   Formula 1B

R a —O—CO—X—CO—O—R  Formula 1C

wherein

R a is the group

(i) R f (CH 2 CF 2 ) d —(C g H 2g )—;

(ii) R f OCF 2 CF 2 —(C g H 2g )—;

(iii) R f OCFHCF 2 —O—(CH 2 CH 2 O) v —(C g H 2g )—;

(iv) R f OCFHCF 2 O(C w H 2w );

(v) R f OCF(CF 3 )CONH—(C g H 2g )—; or

(vi) R f (CH 2 ) h [(CF 2 CF 2 ) i (CH 2 CH 2 ) j ] k

each R f is independently C c F (2c+1) ;

c is 2 to about 6;

d is 1 to about 3;

g is 1 to 4;

v is 1 to about 4;

w is from about 3 to about 12;

h is 1 to about 6;

i, j, and k are each independently 1, 2, or 3, or a mixture thereof;

provided that the total number of carbon atoms in group (vi) is from about 8 to about 22;

X is a linear or branched difunctional alkyl sulfonate group

—C e H (2e−1) (SO 3 M)-,

wherein e is 2 or 3;

M is a monovalent cation selected from the group consisting of hydrogen, ammonium, and alkali metal;

R is H or a linear or branched alkyl group C b H (2b+1) —; and

b is from 1 to about 18.

2. The compound of claim 1 wherein R a is R f (CH 2 CF 2 ) d —(C g H 2g )—; R f OCF 2 CF 2 —(C g H 2g )—; R f OCFHCF 2 O(CH 2 CH 2 O) v —(C g H 2g )—; or R f OCFHCF 2 O(C w H 2w )—.

3. The compound of claim 1 wherein c is 3 or 4 or 6.

4. The compound of claim 1 wherein X is CH 2 CH(SO 3 M), CH 2 CH(CH 2 SO 3 M), CH(CH 3 )CH(SO 3 M), CH 2 CH(SO 3 M)CH 2 , or CH 2 CH(SO 3 M)CH 2 CH 2 .

5. The compound of claim 2 wherein d is 1, g is 2, and R f is C 3 F 7 or C 4 F 9 .

6. The compound of claim 5 wherein X is C 3 H 5 (SO 3 Na) or CH 2 CH(SO 3 Na).

7. The compound of claim 1 wherein R a is C 4 F 9 CH 2 CF 2 CH 2 CH 2 or C 3 F 7 CH 2 CF 2 CH 2 CH 2 .

8. A method of altering the surface behavior of a liquid comprising adding to the liquid a compound of claim 1 or a mixture thereof.

9. The method of claim 8 wherein the altering of surface behavior is lowering the surface tension.

10. The method of claim 8 wherein the surface behavior is selected from the group consisting of wetting, penetration, spreading, leveling, flowing, emulsifying, dispersing, repelling, releasing, lubricating, etching, bonding, and stabilizing.

11. The method of claim 8 wherein the liquid is a coating composition, latex, polymer, floor finish, ink, emulsifying agent, foaming agent, release agent, repellency agent, flow modifier, film evaporation inhibitor, wetting agent, penetrating agent, cleaner, grinding agent, electroplating agent, corrosion inhibitor, etchant solution, soldering agent, dispersion aid, microbial agent, pulping aid, rinsing aid, polishing agent, personal care composition, drying agent, antistatic agent, floor finish, or bonding agent.

Assignments (4)
RELEASE OF SECURITY INTEREST Recorded Apr 4, 2018
From: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: THE CHEMOURS COMPANY FC, LLC
Reel/Frame 045845/0913 →
SECURITY AGREEMENT Recorded Jun 10, 2015
From: THE CHEMOURS COMPANY FC LLC; THE CHEMOURS COMPANY TT, LLC
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 035839/0675 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 15, 2015
From: E. I. DU PONT DE NEMOURS AND COMPANY
To: THE CHEMOURS COMPANY FC, LLC
Reel/Frame 035432/0023 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 7, 2008
From: MURPHY, PETER MICHAEL; HEWAT, TRACY
To: E. I. DU PONT DE NEMOURS AND COMPANY
Reel/Frame 021356/0025 →