Fluorosilicone copolymers
Described herein, inter alia, are fluorosilicone polymers and copolymers; compositions comprising fluorosilicone polymers and copolymers; lenses, such as intraocular lenses, comprising fluorosilicone polymers and copolymers; and processes for making the fluorosilicone polymers and copolymers.
1. A copolymer of Formula (B):
wherein:
R 20 , R 21 , R 22 , R 23 , and R 24 are each independently hydrogen, fluorine, or C 1-4 alkyl substituted with at least one fluorine; wherein at least one of R 20 , R 21 , R 22 , R 23 , and R 24 is fluorine;
L 3 is independently a bond, —(CH 2 ) 2 —, or —CH(CH 3 )—;
R 30 , R 31 , R 32 , R 33 , R 34 , and R 35 are each independently —CH 3 or —CF 3 ;
m and n are each independently an integer from 1 to 50.
2. The copolymer of claim 1 , wherein R 20 and R 24 are hydrogen; and R 21 , R 22 , and R 23 are fluorine.
3. The copolymer of claim 1 , wherein L 3 is a bond.
4. The copolymer of claim 1 , wherein the ratio of min is from about 10:90 to about 90:10.
5. The copolymer of claim 1 having a number average molecular weight from about 2,000 to about 5,000.
6. A composition comprising a plurality of the copolymer of claim 1 .
7. The composition of claim 6 having a viscosity from about 500 cP to about 10,000 cP.
8. The composition of claim 6 having a refractive index from about 1.40 to about 1.50.
9. A lens comprising:
(i) an anterior portion comprising a refractive optical element;
(ii) a posterior portion; and
(iii) an enclosed cavity between the anterior portion and the posterior portion, wherein the enclosed cavity comprises the copolymer of claim 1 .
10. A method of treating a cataract in an eye of a patient in need thereof, the method comprising implanting an intraocular lens into the eye of the patient;
wherein the intraocular lens comprises:
(i) an anterior portion comprising a refractive optical element;
(ii) a posterior portion; and
(iii) an enclosed cavity between the anterior portion and the posterior portion, wherein the enclosed cavity comprises the copolymer of claim 1 .
11. A copolymer of Formula (A):
wherein:
R 1 , R 2 , R 3 , R 8 , R 9 , and R 10 are each independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;
R 4 and R 6 are each independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;
L 1 and L 2 are each independently a bond, substituted or unsubstituted alkylene, or substituted or unsubstituted heteroalkylene;
R 5 is independently R 5A -substituted aryl; wherein R 5A is independently fluorine;
R 7 is independently unsubstituted or R 7A -substituted alkyl, unsubstituted or R 7A -substituted heteroalkyl, unsubstituted or R 7A -substituted aryl, or unsubstituted or R 7A -substituted heteroaryl; wherein R 7A is independently fluorine, R 7B -substituted alkyl, or R 7B -substituted heteroalkyl; wherein R 7B is fluorine; and
m and n are each independently an integer from 1 to about 100.
12. The copolymer of claim 11 , wherein R 7 is independently unsubstituted or R 7A -substituted alkyl or unsubstituted or R 7A -substituted aryl; wherein R 7A is independently fluorine or R 7B -substituted alkyl; wherein R 7B is fluorine.
13. The copolymer of claim 11 , wherein R 7 is R 7A -substituted alkyl.
14. The copolymer of claim 11 , wherein:
R 1 , R 2 , R 3 , R 8 , R 9 , and R 10 are each independently hydrogen, unsubstituted C 1 -C 6 alkyl, C 1 -C 6 alkyl substituted with at least one fluorine, C 1 -C 6 alkyl substituted with a 6 membered aryl that is substituted with at least one fluorine, or 6 membered aryl substituted with at least one fluorine;
R 4 and R 6 are each independently hydrogen, substituted or unsubstituted C 1 -C 6 alkyl, or substituted or unsubstituted phenyl;
L 1 and L 2 are each independently a bond or a substituted or unsubstituted C 1 -C 6 alkylene;
R 5 is R 5A -substituted aryl;
R 5A is independently fluorine or C 1 -C 4 alkyl substituted with at least one fluorine;
R 7 is independently phenyl, unsubstituted C 1 -C 6 alkyl, or C 1 -C 6 alkyl substituted with at least one fluorine; and
m and n are each independently an integer from 1 to about 50.
15. The copolymer of claim 11 , wherein:
R 1 , R 2 , R 3 , R 8 , R 9 , and R 10 are each independently —CH 3 or —CF 3 ;
R 4 and R 6 are each independently unsubstituted C 1 -C 4 alkyl;
L 1 is a bond;
L 2 is unsubstituted C 1 -C 4 alkylene;
R 5 is phenyl substituted with 1 to 5 fluorine;
R 7 is R 7A -substituted C 1 -C 4 alkyl;
R 7A is fluorine; and
m and n are each independently an integer from 1 to about 50.
16. The copolymer of claim 11 , wherein the copolymer has a number average molecular weight of about 1,000 to about 6,000.
17. A composition comprising a plurality of the copolymer of claim 11 .
18. The composition of claim 17 having:
(a) a viscosity from about 500 cP to about 10,000 cP;
(b) a refractive index from about 1.40 to about 1.47;
(c) a light transmittance of at least 95% in the visible light range of 400 nm to 700 nm; or
(d) a combination of two or more of (a), (b), and (c).
19. A lens comprising:
(i) an anterior portion comprising a refractive optical element;
(ii) a posterior portion; and
(iii) an enclosed cavity between the anterior portion and the posterior portion, wherein the enclosed cavity comprises the copolymer of Formula (B):
wherein:
R 20 , R 21 , R 22 , R 23 , and R 24 are each independently hydrogen, fluorine, or C 1-4 alkyl substituted with at least one fluorine;
L 3 is independently a bond, —(CH 2 ) 2 —, or —CH(CH 3 )—;
R 30 , R 31 , R 32 , R 33 , R 34 , and R 35 are each independently —CH 3 or —CF 3 ;
m and n are each independently an integer from 1 to 50.
20. A method of treating a cataract in an eye of a patient in need thereof, the method comprising implanting an intraocular lens into the eye of the patient;
wherein the intraocular lens comprises:
(i) an anterior portion comprising a refractive optical element;
(ii) a posterior portion; and
(iii) an enclosed cavity between the anterior portion and the posterior portion, wherein the enclosed cavity comprises the copolymer of claim 11 .
21. The lens of claim 19 , wherein R 20 and R 24 are hydrogen; R 21 , R 22 , and R 23 are fluorine; and L 3 is a bond.
22. The lens of claim 19 , wherein R 20 , R 21 , R 22 , R 23 , and R 24 are hydrogen; and L 3 is a bond.
23. The lens of claim 19 , wherein the ratio of min is from about 10:90 to about 90:10.
24. The lens of claim 19 , wherein the copolymer has a number average molecular weight from about 2,000 to about 5,000.
25. The lens of claim 19 , wherein the anterior portion and the posterior portion comprise a silicone elastomer.
26. The lens of claim 19 , wherein the lens is an intraocular lens.
27. A method of treating a cataract in an eye of a patient in need thereof, the method comprising implanting the lens of claim 26 into the eye of the patient.
28. A method of treating a cataract in an eye of a patient in need thereof, the method comprising implanting an intraocular lens into the eye of the patient;
wherein the intraocular lens comprises:
(i) an anterior portion comprising a refractive optical element;
(ii) a posterior portion; and
(iii) an enclosed cavity between the anterior portion and the posterior portion, wherein the enclosed cavity comprises the copolymer of Formula (B):
wherein:
R 20 , R 21 , R 22 , R 23 , and R 24 are each independently hydrogen, fluorine, or C 1-4 alkyl substituted with at least one fluorine;
L 3 is independently a bond, —(CH 2 ) 2 —, or —CH(CH 3 )—;
R 30 , R 31 , R 32 , R 33 , R 34 , and R 35 are each independently —CH 3 or —CF 3 ;
m and n are each independently an integer from 1 to 50.
29. A lens comprising:
(i) an anterior portion comprising a refractive optical element;
(ii) a posterior portion; and
(iii) an enclosed cavity between the anterior portion and the posterior portion, wherein the enclosed cavity comprises a liquid silicone composition comprising a plurality of the copolymer of Formula (B), wherein the liquid silicone composition has a refractive index from about 1.40 to about 1.47, and wherein the copolymer of Formula (B) is:
wherein:
R 20 , R 21 , R 22 , R 23 , and R 24 are each independently hydrogen, fluorine, or C 1-4 alkyl substituted with at least one fluorine;
L 3 is independently a bond, —(CH 2 ) 2 —, or —CH(CH 3 )—;
R 30 , R 31 , R 32 , R 33 , R 34 , and R 35 are each independently —CH 3 or —CF 3 ; and
m and n are each independently an integer from 1 to 50.
30. The lens of claim 29 , wherein R 20 and R 24 are hydrogen; and R 21 , R 22 , and R 23 are fluorine; and L 3 is a bond.
31. The lens of claim 29 , wherein R 20 , R 21 , R 22 , R 23 , and R 24 are hydrogen; and L 3 is a bond.
32. The lens of claim 29 , wherein the ratio of min is from about 10:90 to about 90:10.
33. The lens of claim 29 , wherein the copolymer has a number average molecular weight from about 2,000 to about 5,000.
34. The lens of claim 29 , wherein the liquid silicone composition has a viscosity from about 500 cP to about 10,000 cP.
35. The lens of claim 29 , wherein the liquid silicone composition has a light transmittance of at least 95% in the visible light range of 400 nm to 700 nm.
36. The lens of claim 29 , wherein the liquid silicone composition has a refractive index from about 1.41 to about 1.46.
37. The lens of claim 29 , wherein the anterior portion and the posterior portion comprise a silicone elastomer.
38. The lens of claim 29 , wherein the lens is an intraocular lens.
39. A method of treating a cataract in an eye of a patient in need thereof, the method comprising implanting the lens of claim 38 into the eye of the patient.
40. A lens comprising:
(i) an anterior portion comprising a refractive optical element;
(ii) a posterior portion; and
(iii) an enclosed cavity between the anterior portion and the posterior portion, wherein the enclosed cavity comprises the copolymer of claim 11 .