F-POSS coatings and additives and methods of making same
View Patent ↗Fluorinated polyhedral oligomeric silsesquioxane (“F-POSS”) copolymers and terpolymers useful in the field of coatings for enhancing performance of materials surfaces. Also disclosed are methods for making such copolymers and terpolymers.
1. An F-POSS copolymer, comprising the formula:
(—(CH 2 CR 1 (C(O)O(CH 2 ) n F-POSS)) x -(CH 2 CR 1a (C(O)O(CH 2 ) n1 R 2 )) y —(CH 2 CR 1b (C(O)O(CH 2 ) n2 F-POSS)) x1 -(CH 2 CR 1c (C(O)O(CH 2 ) n3 CH 3 )) z ) p —,
wherein
R 1 , R 1a , R 1b and R 1c are each independently H or —CH 3 ;
R 2 is —OH or —NCO; and
n is an integer from 1 to 5;
n1 is an integer from 1 to 18;
n2 is an integer from 1 to 5;
n3 is an integer from 0 to 5;
p is an integer from 1 to about 10;
x is an integer from 1 to about 5;
x1 is an integer from 0 to about 3;
y is an integer from about 50 to about 1200; and
z is an integer from 0 to about 1000.
2. The F-POSS copolymer of claim 1 , wherein n is 3.
3. The F-POSS copolymer of claim 2 , wherein R 1 is —CH 3 .
4. The F-POSS copolymer of claim 3 , wherein R 1a is —CH 3 .
5. The F-POSS copolymer of claim 4 , wherein n1 is 2.
6. The F-POSS copolymer of claim 5 , wherein x1 is 0.
7. The F-POSS copolymer of claim 6 , wherein z is 0.
8. The F-POSS copolymer of claim 7 , wherein R 2 is —OH.
9. The F-POSS copolymer of claim 5 , wherein R 2 is —NCO.
10. The F-POSS copolymer of claim 9 , wherein z is an integer from about 50 to about 1000.
11. The F-POSS copolymer of claim 10 , wherein x1 is an integer from 1 to about 3.
12. The F-POSS copolymer of claim 11 , wherein R 1b is —CH 3 .
13. The F-POSS copolymer of claim 12 , wherein n2 is 3.
14. The F-POSS copolymer of claim 13 , wherein R 1c is —CH 3 .
15. The F-POSS copolymer of claim 14 , wherein n3 is 0.
16. A copolymer produced by a process, comprising:
copolymerizing an F-POSSMA monomer of the formula
CH 2 ═CR 1 (C(O)O(CH 2 ) n F-POSS)
wherein R 1 is H or —CH 3 , and n is an integer from 1 to 5, with an acrylate monomer of the formula I
CH 2 ═CR 1a (C(O)O(CH 2 ) n1 R 2 ) (I)
wherein
R 1a is H or —CH 3 ;
R 2 is —OH or —NCO;
and
n1 is an integer from 1 to 18;
and optionally an acrylate monomer of the formula II
CH 2 ═CR 1c (C(O)O(CH 2 ) n3 CH 3 ) (II)
wherein R 1c is H or —CH 3 ; and n3 is an integer from 0 to 5.
17. The copolymer of claim 16 , wherein the molar ratio of the acrylate monomer to the F-POSSMA monomer is from about 100:1 to about 800:1.
18. The copolymer of claim 16 , wherein the molar ratio of the acrylate monomers I and II to the F-POSSMA monomer is from about 40:1 to about 800:1.
19. A process for preparing an F-POSS copolymer, comprising:
contacting an F-POSS MA monomer of the formula
CH 2 ═CR 1 (C(O)O(CH 2 ) n F-POSS)
wherein R 1 is H or —CH 3 , and n is an integer from 1 to 5, with and acrylate monomer of the formula I
CH 2 ═CR 1a (C(O)O(CH 2 ) n1 R 2 ) (I)
wherein
R 1a is H or —CH 3 ;
R 2 is —OH or —NCO;
and
n1 is an integer from 1 to 18;
and optionally and acrylate monomer of the formula II
CH 2 ═CR 1c (C(O)O(CH 2 ) n3 CH 3 ) (II)
wherein R 1c is H or —CH 3 , and n3 is an integer from 0 to 5; in the presence of an initiator.