Mono ethylenically unsaturated polymerizable group containing polycarbosiloxane monomers
View Patent ↗The present invention relates to polymeric compositions useful in the manufacture of biocompatible medical devices. More particularly, the present invention relates to certain monoethylenically unsaturated polymerizable group containing polycarbosiloxane monomers capable of polymerization to form polymeric compositions having desirable physical characteristics useful in the manufacture of ophthalmic devices.
1. A hydrogel contact lens comprising a polymerized monomer mix comprising a polymerizable monomer mixture comprising about 0.1 to about 75.8 percent by weight of
about 0 to about 41.2 percent by weight of a bulky siloxane monomer, about 0 to about 78 percent by weight of at least one hydrophilic monomer, about 0 to about 48.6 percent by weight of an alcohol, about 0.1 to about 29.9 weight percent of an mono ethylenically unsaturated polymerizable group containing polycarbosiloxane monomer, about 0.1 to about 1.0 percent by weight of an initiator and about 90 to about 200 parts per million of a visibility tint.
2. The hydrogel contact lens of claim 1 wherein the mono ethylenically unsaturated polymerizable group containing polycarbosiloxane monomer is a monomer having a structural formula (I):
wherein X is the residue of a ring opening agent or a capping agent; L is the same or different and is a linker group or a bond; V is an ethylenically unsaturated polymerizable group; R 1 , R 2 , R 3 , R 4 , R 5 , R 6 are independently H, alkyl, halo alkyl, heteroalkyl, cyclo alkyl, heterocyclo alkyl, alkenyl, halo alkenyl, or aromatic; R 7 and R 8 are independently H or alkyl wherein at least one of R 7 or R 8 is hydrogen; y is 2-7 and n is 1-100.
3. The hydrogel contact lens of claim 1 wherein the mono ethylenically unsaturated polymerizable group containing polycarbosiloxane monomer is a monomer having a structural formula (II)
wherein L is the same or different and is a linker group or a bond and V is an ethylenically unsaturated polymerizable group, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 9 are independently H, alkyl, halo alkyl, cyclo alkyl, heterocyclo alkyl, alkenyl, halo alkenyl, or aromatic, R 7 and R 8 are independently H or alkyl wherein at least one of R 7 or R 8 is hydrogen, y is 2-7 and n is 1-100.
4. The hydrogel contact lens of claim 2 wherein X is a residue of a ring opening agent selected from the group consisting of alkyl lithiums, alkoxides and trialkylsiloxylithiums.
5. The hydrogel contact lens of claim 2 or 3 wherein the linker group is selected from the group consisting of substituted or unsubstituted alkyl, alkyl ether, alkenyls, alkenyl ethers, halo alkyls, substituted or unsubstituted siloxanes, and monomers capable of propagating ring opening.
6. The hydrogel contact lens of claim 1 wherein the mono ethylenically unsaturated polymerizable group containing polycarbosiloxane monomer is a monomer having a structural formula (III):
wherein R 9 , R 10 and R 11 are independently H, alkyl, haloalkyl or other substituted alkyl groups, n is 1-100 and n 1 is 0-10.
7. The hydrogel contact lens of claim 1 wherein the mono ethylenically unsaturated polymerizable group containing polycarbosiloxane monomer is a monomer having a structural formula (IV):
wherein n is 1-100.
8. The hydrogel contact lens of claim 7 wherein n is 2-80.
9. The hydrogel contact lens of claim 7 wherein n is 3-20.
10. The hydrogel contact lens of claim 7 wherein n is 5-15.
11. The hydrogel contact lens of claim 2 or 3 wherein V is selected from the group consisting of acrylates, methacrylates, vinyl carbonates, O-vinyl carbamates, N-vinyl carbamates, acrylamides and methacrylamides.
12. The hydrogel contact lens of claim 2 wherein the mono ethylenically unsaturated polymerizable group containing polycarbosiloxane monomer is a monomer having a structural formula selected from the group consisting of the following structural formulae:
13. The hydrogel contact lens of claim 2 wherein the mono ethylenically unsaturated polymerizable group containing polycarbosiloxane monomer is a monomer having a structural formula selected from the group consisting of the following structural formulae:
wherein R 9 , R 10 and R 11 are independently H, alkyl, haloalkyl or other substituted alkyl groups and n is 1-100 and n 1 is 0-10.
14. The hydrogel contact lens of claim 2 wherein the mono ethylenically unsaturated polymerizable group containing polycarbosiloxane monomer is a monomer having a structural formula selected from the group consisting of the following structural formulae:
wherein n is 1-100 and X − is a counterion to provide an overall neutral charge.
15. The hydrogel contact lens of claim 2 wherein the mono ethylenically unsaturated polymerizable group containing polycarbosiloxane monomer is a monomer having the following structural formula: