Fluorosilicone polymers, compositions, and uses thereof
Described herein, inter alia, are fluorosilicone polymers; compositions comprising fluorosilicone polymers; and lenses comprising the polymers, and compositions.
1 . 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 composition comprising a copolymer, wherein the copolymer comprises a repeating unit of formula (I) and a repeating unit of formula (II),
wherein
(a) the repeating unit of formula (I) is
wherein:
L 1 is a bond, substituted or unsubstituted alkylene, or substituted or unsubstituted heteroalkylene;
R 4 is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;
R 5 is unsubstituted or R 5A -substituted aryl, unsubstituted or R 5A -substituted heteroaryl, unsubstituted or R 5A -substituted alkyl, or unsubstituted or R 5A -substituted heteroalkyl;
R 5A is fluorine, R 5B -substituted alkyl, or R 5B -substituted heteroalkyl; and
R 5B is fluorine; and
(b) the repeating unit of formula (II) is
wherein:
R 6 is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;
L 2 is a bond, substituted or unsubstituted alkylene, or substituted or unsubstituted heteroalkylene; and
R 7 is 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.
2 . The lens of claim 1 , wherein:
(a) in the repeating unit of formula (I):
L 1 is a bond;
R 4 is hydrogen, substituted or unsubstituted C 1-4 alkyl, or substituted or unsubstituted phenyl;
R 5 is unsubstituted phenyl or R 5A -substituted phenyl;
R 5A is fluorine, R 5B -substituted alkyl, or R 5B -substituted heteroalkyl; and
R 5B is fluorine; and
(b) in the repeating unit of formula (II):
R 6 is hydrogen, substituted or unsubstituted C 1-4 alkyl, or substituted or unsubstituted phenyl;
L 2 is a bond;
R 7 is R 7A -substituted alkyl;
R 7A is independently fluorine, R 7B -substituted alkyl, or R 7B -substituted heteroalkyl; and
R 7B is fluorine.
3 . The lens of claim 1 , wherein:
(a) in the repeating unit of formula (I):
L 1 is a bond;
R 4 is hydrogen, unsubstituted C 1-4 alkyl, or unsubstituted phenyl;
R 5 is unsubstituted phenyl;
(b) in the repeating unit of formula (II):
R 6 is hydrogen, unsubstituted C 1-4 alkyl, or unsubstituted phenyl;
L 2 is a bond;
R 7 is R 7A -substituted alkyl;
R 7A is independently fluorine or R 7B -substituted alkyl; and
R 7B is fluorine.
4 . The lens of claim 1 , wherein the repeating unit of formula (I) is a repeating unit of formula (IA):
wherein
L 1 is a bond;
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.
5 . The lens of claim 4 , wherein L 1 is a bond; R 20 and R 24 are hydrogen; and R 21 , R 22 , and R 23 are fluorine.
6 . The lens of claim 4 , wherein L 1 is a bond; and R 20 , R 21 , R 22 , R 23 , and R 24 are hydrogen.
7 . The lens of claim 4 , wherein the repeating unit of formula (II) is a repeating unit of formula (IIA):
8 . The lens of claim 1 , wherein the copolymer has a number average molecular weight of about 1,000 to about 6,000.
9 . The lens of claim 8 , wherein the copolymer has a number average molecular weight of about 1,000 to about 6,000.
10 . The lens of claim 1 , wherein wherein the composition has a viscosity from 500 cP to 10,000 cP.
11 . The lens of claim 10 , wherein wherein the composition has a viscosity from 500 cP to 5,000 cP.
12 . The lens of claim 1 , wherein the composition has a light transmittance of at least 90% in the visible light range of 400 nm to 700 nm.
13 . The lens of claim 12 , wherein the composition has a light transmittance of at least 96% in the visible light range of 400 nm to 700 nm.
14 . The lens of claim 1 , wherein the composition has a refractive index from 1.40 to 1.50.
15 . The lens of claim 14 , wherein the composition has a refractive index from 1.42 to 1.47.
16 . The lens of claim 1 , wherein the anterior portion and the posterior portion comprise a silicone elastomer.
17 . The lens of claim 1 , wherein the lens is an intraocular lens.
18 . A copolymer comprising a repeating unit of formula (I) and a repeating unit of formula (II), wherein
(a) the repeating unit of formula (I) is
wherein:
L 1 is a bond, substituted or unsubstituted alkylene, or substituted or unsubstituted heteroalkylene;
R 4 is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;
R 5 is R 5A -substituted phenyl; and
R 5A is fluorine; and
(b) the repeating unit of formula (II) is
wherein:
R 6 is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;
L 2 is a bond, substituted or unsubstituted alkylene, or substituted or unsubstituted heteroalkylene;
R 7 is 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.
19 . The copolymer of claim 18 , wherein the repeating unit of formula (I) is a repeating unit of formula (IA):
wherein
L 1 is a bond;
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, wherein at least one of R 20 , R 21 , R 22 , R 23 , and R 24 is fluorine; and
wherein the repeating unit of formula (II) is a repeating unit of formula (IIA):
20 . The copolymer of claim 19 , wherein L 1 is a bond; R 20 and R 24 are hydrogen; and R 21 , R 22 , and R 23 are fluorine.