FLUOROSILICONE POLYMERS, COMPOSITIONS, AND USES THEREOF
Fluorosilicone polymers and compositions comprising fluorosilicone polymers are useful in lenses, such as intraocular lenses.
1 . A polymer comprising a repeating unit of Formula (I):
wherein:
L 1 is independently a bond, substituted or unsubstituted alkylene, or substituted or unsubstituted heteroalkylene;
R 4 is independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;
R 5 is independently R 5A -substituted aryl, R 5A -substituted heteroaryl, R 5A -substituted alkyl, or R 5A -substituted heteroalkyl;
R 5A is independently fluorine, R 5B -substituted alkyl, or R 5B -substituted heteroalkyl; and
R 5B is fluorine.
2 . The polymer of claim 1 , wherein the repeating unit of Formula (I) is a repeating unit of Formula (IA):
wherein R 20 , R 21 , R 22 , R 23 , and R 24 are each independently hydrogen, fluorine, or C 1 -C 4 alkyl substituted with at least one fluorine.
3 . The polymer of claim 1 , wherein L 1 is a bond.
4 . The polymer of claim 1 , wherein
L 1 is —(CH 2 ) w CR a R b —,
w is an integer from 0 to 6;
R a is substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl; and
R b is substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.
5 . The polymer of claim 1 , wherein the repeating unit of Formula (I) is a repeating unit of Formula (IB):
6 . The polymer of claim 1 , wherein the repeating unit of Formula (I) is a repeating unit of Formula (IC):
7 . The polymer of claim 1 , further comprising a repeating unit of Formula (II):
wherein:
R 6 is independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;
L 2 is independently a bond, substituted or unsubstituted alkylene, or substituted or unsubstituted heteroalkylene; and
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;
R 7A is independently fluorine, R 7B -substituted alkyl, or R 7B -substituted heteroalkyl; and
R 7B is fluorine.
8 . The polymer of claim 7 , wherein the repeating unit of Formula (II) is a repeating unit of Formula (IIA):
9 . The polymer of claim 7 , having the structure 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; and
m and n are each independently an integer from 1 to about 100.
10 . The polymer of claim 9 , having the structure of Formula (A1):
wherein:
R 1 , R 2 , R 3 , R 1 , R 9 , and R 10 are each independently H, —CH 3 , or —CF 3 ; and
m and n are each independently an integer from 1 to 20.
11 . The polymer of claim 9 , having the structure of Formula (A2):
wherein m and n are each independently an integer from 2 to 18.
12 . The polymer of claim 9 , having the structure of Formula (A3):
wherein m and n are each independently an integer from 2 to 18.
13 . The polymer of claim 9 , having the structure of Formula (A5):
wherein m and n are each independently an integer from 2 to 18.
14 . The polymer of claim 1 having a number average molecular weight from about 500 to about 18,000.
15 . The polymer of claim 1 , wherein the ratio of m:n is from about 10:90 to about 90:10.
16 . The polymer of claim 1 , further comprising a repeating unit of Formula (III):
wherein:
R 11 is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;
L 5 is a bond, substituted or unsubstituted alkylene, or substituted or unsubstituted heteroalkylene; and
R 40 is a stabilizer moiety, hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.
17 . The polymer of claim 16 , having the structure of Formula (A1):
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;
m and n are each independently an integer from 1 to about 100; and
p is proportional to the total of m+n in a range of about 0.0001 to about 0.1.
18 . A composition comprising a plurality of the polymer of claim 1 .
19 . The composition of claim 18 , further comprising a stabilizer.
20 . 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 polymer of claim 1 .