High refractive index monomers and (co)polymers prepared therefrom
The present invention relates to high refractive index monomers according to formula (I) and (co)polymers comprising such high refractive index monomers. The 5 (co)polymers are highly suitable for the manufacture of optical articles, in particular flexible optical articles, more in particular intraocular lenses.
1. A high refractive index monomer according to formula (I):
wherein:
R 1 is H or CH 3 ;
X is O or S;
R 2 is independently H or linear or branched C 1 -C 6 alkyl;
n=3 to 10;
m=1- 10;
R 3 is linear or branched C 1 -C 3 alkylene;
Y is O or S;
p=0- 5;
R 4 is C 6 -C 18 aryl or heteroaryl;
q is 2 or 3;
o is 0 or 1;
when q=2, then o is 1;
when q=3; then o is 0; and
R 5 is independently H or linear or branched C 1 -C 6 alkyl.
2. The high refractive index monomer according to claim 1 , wherein n is 3-5.
3. The high refractive index monomer according to claim 1 , wherein m=1-5.
4. The high refractive index monomer according to claim 1 , wherein X is O.
5. The high refractive monomer according to claim 1 , wherein Y is S.
6. The high refractive index monomer according to claim 1 , wherein p is 0.
7. The high refractive index monomer according to claim 1 , wherein q is 2 and o is 1.
8. The high refractive index monomer according to claim 1 , wherein R 5 is H.
9. The high refractive index monomer according to claim 1 , wherein R 4 is phenyl.
10. The high refractive index monomer according to formula (II):
wherein:
R 1 is H or CH 3 ;
X is O or S;
R 2 is independently H or linear or branched C 1 -C 6 alkyl;
a=1 to 5;
R 3 is linear or branched C 1 -C 3 alkylene;
Y is O or S;
d=0-5;
R 4 is C 6 -C 18 aryl or heteroaryl;
b is 2 or 3;
c is 0 or 1;
when b=2, then c is 1;
when b=3; then c is 0; and
R 5 is independently H or linear or branched C 1 -C 6 alkyl.
11. The high refractive index monomer according to claim 10 , wherein a is 1 or 2.
12. The high refractive index monomer according to claim 10 , wherein d is 0.
13. The high refractive index monomer according to claim 10 , wherein b is 2 and c is 1.
14. The high refractive index monomer according to claim 10 , wherein X is 0.
15. The high refractive monomer according to claim 10 , wherein Y is S.
16. The high refractive index monomer according to claim 10 , wherein R 5 is H.
17. The high refractive index monomer according to claim 10 , wherein R 4 is phenyl.
18. A polymer comprising:
(a) a high refractive index monomer according to formula (I):
wherein:
R 1 is H or CH 3 ;
X is O or S;
R 2 is independently H or linear or branched C 1 -C 6 alkyl;
n=3 to 10;
m=1-10;
R 3 is linear or branched C 1 -C 3 alkylene;
Y is O or S;
p=0-5;
R 4 is C 6 -C 18 aryl or heteroaryl;
q is 2 or 3;
o is 0 or 1;
when q=2, then o is 1;
when q=3; then o is 0; and
R 5 is independently H or linear or branched C 1 -C 6 alkyl; or
(b) a high refractive index monomer according to formula (II):
wherein:
R 1 is H or CH 3 ;
X is O or S;
R 2 is independently H or linear or branched C 1 -C 6 alkyl;
a=1 to 5;
R 3 is linear or branched C 1 -C 3 alkylene;
Y is O or S;
d=0-5;
R 4 is C 6 -C 18 aryl or heteroaryl;
b is 2 or 3;
c is 0 or 1;
when b=2, then c is 1;
when b=3; then c is 0; and
R 5 is independently H or linear or branched C 1 -C 6 alkyl,
wherein said polymer have a glass transition temperature T g of less than 25° C.
19. The polymer according to claim 18 comprising a crosslinked homopolymer comprising the high refractive index monomers according to formulas (I) or (II).
20. The polymer according to claim 18 comprising a crosslinked copolymer comprising the high refractive index monomers according to formulas (I) or (II), at least a second acrylic monomer, and a crosslinking monomer.
21. The polymer according to claim 20 , wherein the second acrylic monomer is represented by formula (VIII):
wherein:
R 1 is H or CH 3 ;
R 4 is C 6 -C 18 aryl or heteroaryl;
R 6 is substituted or unsubstituted C 1 -C 6 alkylene;
X is as defined above;
Z is O, S or a direct bond; and
r is 0, 1, 2 or 3.
22. The polymer according to claim 20 , wherein the crosslinking monomer is a multifunctional (meth)acrylate monomer which comprises at least two (meth)acrylate moieties.
23. The polymer according to claim 20 , wherein the crosslinking monomer is represented by the general formula (IX):
wherein:
R 1 is H or CH 3 ;
R 7 is substituted or unsubstituted C 1 -C 300 alkyl, aryl, alkaryl, arylalkyl or heteroaryl;
X is as defined above; and
s=2, 3 or 4.
24. An intraocular lens comprising the polymer according to claim 18 .