Fluorinated copolymers of (meth)acrylates and (meth)acrylic acid amine complexes
View Patent ↗A stain resistant, oil and water repellent copolymer comprising a copolymer prepared from fluorinated (meth)acrylate and amine salts of (meth)acrylic acid, and a method of providing stain resistance, oil and water repellency to substrates and a treated substrate.
1. A copolymer comprising formula (I)
wherein
R f is C 4 to C 6 fluoroalkyl, optionally interrupted by one or more —O —, —CH 2 —, —CFH—, or combinations thereof;
n is an integer from 1 to 10;
R 1 and R 2 are each independently H or CH 3 ;
R 3 is H, CH 3 , or CH 2 CH 3 ;
R 4 is H, CH 3 , or CH 2 CH 3 ;
R 5 is C 6 to C 18 alkyl or Y;
R 6 is H, CH 3 , or CH 2 CH 3 ;
R 7 is H, CH 3 , or CH 2 CH 3 ;
R 8 is H, CH 3 , CH 2 CH 3 , or Y;
wherein a, b, and c are defined such that either
a is 30 to 50 mol %, b is 1 to 10 mol %, and c is 45 to 65 mol %; or
a is 35 to 45 mol %, b is 0 mol %, and c is 55 to 65 mol %;
provided that (a+b+c) equals 100;
Y is
R 9 is each independently alkyl, alkyl alcohol, or hydrogen; and
m is 1 to 10.
2. A copolymer of claim 1 , wherein R 5 is C 6 to C 18 alkyl.
3. A copolymer of claim 1 , wherein R 5 is Y, wherein Y is
R 9 is each independently alkyl, alkyl alcohol, or hydrogen; and
m is 1 to 10.
4. A copolymer of claim 3 , wherein each R 9 is hydrogen.
5. A copolymer of claim 3 , wherein each R 9 is independently an alkyl.
6. A copolymer of claim 1 , wherein R 5 is C 6 to C 18 alkyl; R 8 is Y, wherein Y is
R 9 is each independently alkyl, alkyl alcohol, or hydrogen; and
m is 1 to 10.
7. A copolymer of claim 6 , wherein R 5 is C 6 to C 18 alkyl; R 8 is Y, wherein Y is —(CH 2 ) m —Si(OR 9 ) 3 ; R 9 is each independenly alkyl, alcohol, or hydrogen; and
m is 1 to 10.
8. A copolymer of claim 6 , wherein Y is
R 9 is each independently alkyl, alkyl alcohol, or hydrogen; and
m is 1 to 10.
9. A copolymer of claim 6 , wherein Y is
R 9 is each independently alkyl, alkyl alcohol, or hydrogen; and
m is 1 to 10.
10. A copolymer of claim 6 , wherein Y is
R 9 is each independently alkyl, alkyl alcohol, or hydrogen; and
m is 1 to 10.
11. A copolymer of claim 1 , wherein the copolymer is in the form of a 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 4 to C 6 fluoroalkyl, optionally interrupted by one or more —O—, —CH 2 —, —CFH—, or combinations thereof;
n is an integer from 1 to 10;
R 1 and R 2 are each independently H or CH 3 ;
R 3 is H, CH 3 , or CH 2 CH 3 ;
R 4 is H, CH 3 , or CH 2 CH 3 ;
R 5 is C 6 to C 18 alkyl or Y;
R 6 is H, CH 3 , or CH 2 CH 3 ;
R 7 is H, CH 3 , or CH 2 CH 3 ;
R 8 is H, CH 3 , CH 2 CH 3 , or Y;
wherein a, b, and c are defined such that either
a is 30 to 50 mol %, b is 1 to 10 mol %, and c is 45 to 65 mol %; or
a is 35 to 45 mol %, b is 0 mol %, and c is 55 to 65 mol %;
provided that (a+b+c) equals 100;
Y is
R 9 is each independently alkyl, alkyl alcohol, or hydrogen; and
m is 1 to 10.
13. A method of claim 12 wherein the copolymer of Formula I is in the form of an aqueous 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 12 wherein the substrate is unglazed concrete, brick, tile, stone, grout, mortar, composite materials, gypsum board, marble, statuary, monuments, or wood.
16. A substrate treated with a method of claim 12 , which is unglazed concrete, brick, tile, stone, grout, mortar, composite materials, gypsum board, marble, statuary, monuments, or wood.