IP Library Granted Patent US 8,809,209
Granted Patent B2
US 8,809,209 · App. 13/300,999 · Granted Aug 19, 2014

Fluorinated copolymers

Inventors: Joel M. Pollino (Elkton, MD); Anilkumar Raghavanpillai (Wilmington, DE); Brad M. Rosen (Philadelphia, PA); Siddhartha Shenoy (Wilmington, DE); Libby Xiaowei Hu (Exton, PA)
Assignee: E I du Pont de Nemours and Company
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Quick Facts
Patent No.
US 8,809,209
App. No.
13/300,999
Granted
Aug 19, 2014
Kind
B2
Abstract

A stain resistant, oil and water repellent composition comprising a copolymer prepared from fluorinated methacrylate, carbonate methacrylate, and methacrylic acid or salt thereof, a method of providing stain resistance, oil and water repellency to substrates, and a treated substrate.

Claims (40)

1. A composition comprising formula (I)

wherein

R f is C 2 to C 10 fluoroalkyl, optionally interrupted by one or more —O—, —CH 2 —, —CFH—, or combinations thereof;

n is an integer from 1 to 10;

A is a linear, branched, or cyclic carbonate of formula

wherein m is 1 to 10 and R 2 is a C 1 to C 10 linear, branched or cylic alkyl or aryl;

M + is H + , NH 4 + , Na + , Li + , Cs + , K + , or mixtures thereof;

a is 20 to 80 mol %;

b is 5 to 80 mol %; and

c is 0 to 70 mol %;

wherein the sum of a+b+c is equal to 100%.

2. A composition of claim 1 , wherein a is 20 to 80 mol %; b is 20 to 80 mol %; and c is 0 mol %.

3. A composition of claim 2 , wherein R f is C 4 to C 8 , n is 2 to 6, a is 35 to 60 mol %, b is 40 to 70 mol % and c is 0 mol %.

4. A composition of claim 1 , wherein M + is H, a is 20 to 60 mol %; b is 5 to 50 mol %; and c is 25 to 70 mol %.

5. A composition of claim 4 , wherein R f is C 4 to C 8 , n is 2 to 6, a is 30 to 45 mol %, b is 10 to 35 mol %, and c is 30 to 45 mol %.

6. A composition of claim 1 , wherein M + is NH 4 + , Na + , Li + , Cs + , K + , or mixtures thereof, a is 20 to 60 mol %; b is 5 to 50 mol %; and c is 25 to 70 mol %.

7. A composition of claim 6 , wherein R f is C 4 to C 8 , n is 2 to 6, a is 30 to 45 mol %, b is 10 to 35 mol %, and c is 30 to 45 mol %.

8. A composition of claim 1 , wherein the composition is in the form of a dispersion.

9. A composition of claim 2 wherein the composition is in the form of an organic dispersion.

10. A composition of claim 4 wherein the composition is in the form of an organic dispersion.

11. A composition of claim 6 wherein the composition is in the form of an aqueous dispersion.

12. A method of providing water repellency, oil repellency and stain resistance to a substrate surface comprising contacting the substrate surface with a copolymer of Formula I

wherein

R f is C 2 to C 10 fluoroalkyl, optionally interrupted by one or more —O—, —CH 2 —, —CFH—, or combinations thereof;

n is an integer from 1 to 10;

A is a linear, branched, or cyclic carbonate;

M + is H + , NH 4 + , Na + , Li + , Cs + , K + or mixtures thereof;

a is 20 to 80 mol %;

b is 5 to 80 mol %; and

c is 0 to 70 mol %,

wherein the sum of a+b+c is equal to 100%;

to provide stain resistance, oil and water repellency.

13. A method of claim 12 wherein the copolymer of Formula I is in the form of a dispersion.

14. A method of claim 12 wherein the contacting is by brushing, spraying, rollering, dipping, padding, doctor blade, wipe, dip techniques, or wet-on-wet procedure.

15. A method of claim 11 wherein the substrate is unglazed concrete, brick, tile, stone, grout, mortar, composite materials, gypsum board, marble, statuary, monuments, or wood.

16. A method of claim 11 wherein the substrate is woven and nonwoven fibers, yarns, fabrics, fabric blends, textiles, nonwovens, paper, leather, rugs or carpets.

17. A method of claim 16 , where the substrate is cotton, cellulose, wool, silk, polyamide, polyester, polyolefin, polyacrylonitrile, polypropylene, rayon, nylon, aramid, or acetate.

18. A substrate treated with a method of claim 11 , which is unglazed concrete, brick, tile, stone, grout, mortar, composite materials, gypsum board, marble, statuary, monuments, or wood.

19. A substrate treated with a method of claim 11 , which is woven and nonwoven fibers, yarns, fabrics, fabric blends, textiles, nonwovens, paper, leather, rugs or carpets.

20. A substrate treated with a method of claim 19 , which is cotton, cellulose, wool, silk, polyamide, polyester, polyolefin, polyacrylonitrile, polypropylene, rayon, nylon, aramid, or acetate.

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 Apr 17, 2012
From: POLLINO, JOEL M.; RAGHAVANPILLAI, ANILKUMAR; ROSEN, BRAD M.; SHENOY, SIDDHARTHA; HU, LIBBY XIAOWEI
To: E. I. DU PONT DE NEMOURS AND COMPANY
Reel/Frame 028056/0813 →
Continuity (2)
Provisional Application 61424219 · Dec 17, 2010
Related Publication 20120156417A1 · Jun 21, 2012