IP Library Granted Patent US 8,242,301
Granted Patent B2
US 8,242,301 · App. 12/758,280 · Granted Aug 14, 2012

Mixed fluoroalkyl-alkyl surfactants

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Quick Facts
Patent No.
US 8,242,301
App. No.
12/758,280
Granted
Aug 14, 2012
Kind
B2
Abstract

A surfactant of formula 1 (R f -A) a -Q-([B] k —R) b   Formula 1 wherein a and b are each independently 1 or 2; R f is a linear or branched perfluoroalkyl radical having from 2 to about 20 carbon atoms, optionally interrupted with at least one oxygen; R is a C 1 to C 20 linear, branched or cyclic alkyl, or a C 6 to C 10 aryl; B is —(CH 2 CHR 1 O) X —, k is 0 or 1, x is 1 to about 20, A is —(CH 2 ) m [(CHR 1 CH 2 O)] S —[(CH 2 ) m (CH) t CHOH(CH 2 ) m ] e —, wherein each m is independently 0 to 3, s is 0 to about 30, t is 0 or 1, and e is 0 or 1, R 1 is H or CH 3 , Q is: —OP(O)(O − M + )(O)—, —O—, —S—(CH 2 ) m —C(O)—O—, —SO 2 —O— —CH 2 CH 2 O—C(O)CH 2 C(OH)(V)CH 2 C(O)O—; —(CH 2 CH 2 O) X CH 2 CH(OH)—(CH 2 CH 2 O) X —(CH 2 ) m —Si[OSi(R 2 ) 3 ] 2 —, —SO 2 NR 2 —, —(CH 2 CH 2 O) Z C(O)CH(SO 3 − M + )CH 2 C(O)(OCH 2 CH 2 ) Z — wherein z is 1 to about 15, or a bond when s is a positive integer, V is —C(O)OR 3 and R 3 is H, CH 3 or R f ; R 2 is C 1 to C 4 alkyl, and M + is a Group 1 metal or an ammonium (NH X R 2 y ) + cation wherein x+y=4, and R 2 is C 1 to C 4 alkyl, provided that when Q is —OP(O)(O − M + )(O)— or when Q is —(CH 2 CH 2 O) Z —C(O)CH(SO 3 − M + )CH 2 C(O)(OCH 2 CH 2 ) Z —, then at least one of s or e is a positive integer.

Claims (54)

1. A method of lowering surface tension of a medium comprising contacting the medium with a surfactant of Formula 1

(R f -A) a -Q-([B] k —R) b   Formula 1

wherein

a and b are each independently 1 or 2;

R f is a linear or branched perfluoroalkyl radical having from 2 to 20 carbon atoms, optionally interrupted with at least one oxygen;

R is a C 1 to C 20 linear, branched or cyclic alkyl, or a C 6 to C 10 aryl;

B is —(CH 2 CHR 1 O) X —,

k is 0 or 1, x is 1 to 20,

A is —(CH 2 ) m [(CHR 1 CH 2 O)] S —[(CH 2 ) m (CH) t CHOH(CH 2 ) m ] e —,

wherein

each m is independently 0 to 3, s is 0 to 30, t is 0 or 1, and e is 0 or 1,

R 1 is H or CH 3 ,

Q is: —OP(O)(O − M + )(O)—,

—O—,

—S—(CH 2 ) m —C(O)—O—,

—SO 2 —O—

—CH 2 CH 2 O—C(O)CH 2 C(OH)(V)CH 2 C(O)O—;

—(CH 2 CH 2 O) X CH 2 CH(OH)—CH 2 O—(CH 2 CH 2 O) X —(CH 2 ) m —Si[OSi(R 2 ) 3 ] 2 —,

—SO 2 NR 2 —,

—(CH 2 CH 2 O) Z C(O)CH(SO 3 − M + )CH 2 C(O)(OCH 2 CH 2 ) Z — wherein z is 1 to 15, or

a bond when s is a positive integer,

V is —C(O)OR 3 and R 3 is H, CH 3 or R f ,

R 2 is C 1 to C 4 alkyl, and

M + is a Group 1 metal or an ammonium (NH X R 2 y ) + cation wherein x and y are each independently 0 to 4, and x+y=4, and R 2 is C 1 to C 4 alkyl,

provided that when Q is —OP(O)(O − M + )(O)— or when Q is —(CH 2 CH 2 O) Z —C(O)CH(SO 3 − M + )CH 2 C(O)(OCH 2 CH 2 ) Z —, then at least one of s or e is a positive integer.

2. The method of claim 1 wherein the medium 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 polish, or bonding agent.

3. The method of claim 2 wherein the medium is a floor polish.

4. The method of claim 1 wherein the lowering of surface tension enhances wetting and leveling of the medium on a floor.

5. A method of providing resistance to blocking to a coated substrate comprising adding to a coating base prior to deposition on the substrate a compound of Formula 1

(R f -A) a -Q-([B] k —R) b   Formula 1

wherein

a and b are each independently 1 or 2;

R f is a linear or branched perfluoroalkyl radical having from 2 to 20 carbon atoms, optionally interrupted with at least one oxygen;

R is a C 1 to C 20 linear, branched or cyclic alkyl, or a C 6 to C 10 aryl;

B is —(CH 2 CHR 1 O) X —,

k is 0 or 1, x is 1 to 20,

A is —(CH 2 ) m [(CHR 1 CH 2 O)] S —(CH 2 ) m (CH) t CHOH(CH 2 ) m ] e —,

wherein

each m is independently 0 to 3, s is 0 to 30, t is 0 or 1, and e is 0 or 1,

R 1 is H or CH 3 ,

Q is: —OP(O)(O − M + )(O)—,

—O—,

—S—(CH 2 ) m —C(O)—O—,

—SO 2 —O—

—CH 2 CH 2 O—C(O)CH 2 C(OH)(V)CH 2 C(O)O—;

—(CH 2 CH 2 O) X CH 2 CH(OH)—CH 2 O—(CH 2 CH 2 O) X —(CH 2 ) m Si[OSi(R 2 ) 3 ] 2 —,

—SO 2 NR 2 —,

—(CH 2 CH 2 O) Z C(O)CH(SO 3 − M + )CH 2 C(O)(OCH 2 CH 2 ) Z — wherein z is 1 to 15, or

a bond when s is a positive integer,

V is —C(O)OR 3 and R 3 is H, CH 3 or R f ,

R 2 is C 1 to C 4 alkyl, and

M is a Group 1 metal or an ammonium (NH X R 2 y ) + cation wherein x and y are each independently 0 to 4, and x+y=4, and R 2 is C 1 to C 4 alkyl,

provided that when Q is —OP(O)(O − M + )(O)— or when Q is —(CH 2 CH 2 O) Z —C(O)CH(SO 3 − M + )CH 2 C(O)(OCH 2 CH 2 ) Z —, then at least one of s or e is a positive integer.

6. The method of claim 5 wherein the coating base is a water dispersed coating, alkyd coating, Type I urethane coating, unsaturated polyester coating, or a floor polish.

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 INTEREST Recorded Apr 4, 2018
From: THE CHEMOURS COMPANY FC, LLC
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 045846/0011 →
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 →