Prepolymers for improved surface modification of contact lenses
View Patent ↗Provided are a novel class of fumaric- and itaconic-containing prepolymers and compositions comprising the prepolymers used in the manufacture of medical devices.
1. A prepolymer selected from the group consisting of compounds having the following formula:
YCO—CH═CHCOW(R 1 )(SiR 2 R 3 O) m (SiR 2 R 3 )(R 1 )WOCCH═CH—COY
CH 2 ═C(CH 2 COY)COW(R 1 )(SiR 2 R 3 O) m (SiR 2 R 3 )(R 1 )WOC(CH 2 COY)C═CH 2
and
CH 2 ═C(CH 2 COY)COW(R 1 )(SiR 2 R 3 O) m (SiR 2 R 3 )(R 1 )WOCCH 2 (COY)C═CH 2
wherein R 1 is selected from the group consisting of alkylenes and alkylenes containing ether linkages, R 2 and R 3 are independently alkyl or phenyl groups, unsubstituted or substituted with halogen and ether linkages, W is O or NH, m is an integer between 2 and 200, and Y is a residue derived from a reactive oligomer of hydrophilic monomers.
2. The prepolymer of claim 1 wherein R 1 contains 1-10 carbon atoms.
3. The prepolymer of claim 1 wherein the compound has the following formula:
YCO—CH═CHCOW(R 1 )(SiR 2 R 3 O) m (SiR 2 R 3 )(R 1 )WOCCH═CH—COY
wherein R 1 is selected from the group consisting of alkylenes and alkylenes containing ether linkages, R 2 and R 3 are methyl, m is an integer between 5 and 200, W is O and Y is a residue derived from a reactive oligomer derived from hydrophilic monomers selected from the group consisting of amide, hydroxyl and zwitterionic containing hydrophilic monomers and is in a trans configuration.
4. The prepolymer of claim 1 wherein the compound has the following formula:
YCO—CH═CHCOW(R 1 )(SiR 2 R 3 O) m (SiR 2 R 3 )(R 1 )WOCCH═CH—COY
wherein R 1 is selected from the group consisting of alkylenes and alkylenes containing ether linkages, R 2 and R 3 are methyl, m is an integer between 5 and 200, W is O and Y is a residue derived from a reactive oligomer derived from hydrophilic monomers selected from the group consisting of amide, hydroxyl and zwitterionic containing hydrophilic monomers and is in a cis configuration.
5. The prepolymer of claim 1 wherein the compound has the following formula:
CH 2 ═C(CH 2 COY)COW(R 1 )(SiR 2 R 3 O) m (SiR 2 R 3 )(R 1 )WOC(CH 2 COY)C═CH 2
or
CH 2 ═C(CH 2 COY)COW(R 1 )(SiR 2 R 3 O) m (SiR 2 R 3 )(R 1 )WOCCH 2 (COY)C═CH 2
wherein R 1 is selected from the group consisting of alkylenes and alkylenes containing ether linkages, R 2 and R 3 are methyl, m is an integer between 5 and 100, W is O and Y is a residue derived from a reactive oligomer derived from hydrophilic monomers selected from the group consisting of amide, hydroxyl and zwitterionic containing hydrophilic monomers.
6. The prepolymer of claim 1 wherein the compound has the following formula:
YCO—CH═CHCOW(R 1 )(SiR 2 R 3 O) m (SiR 2 R 3 )(R 1 )WOCCH═CH—COY
wherein R 1 is selected from the group consisting of alkylenes and alkylenes containing ether linkages, R 2 and R 3 are methyl, m is an integer between 5 and 200, W is O and Y is a residue derived from a reactive oligomer derived from an ethylenically unsaturated lactam containing monomer and is in a trans configuration.
7. The prepolymer of claim 1 wherein the compound has the following formula:
YCO—CH═CHCOW(R 1 )(SiR 2 R 3 O) m (SiR 2 R 3 )(R 1 )WOCCH═CH—COY
wherein R 1 is selected from the group consisting of alkylenes and alkylenes containing ether linkages, R 2 and R 3 are methyl, m is an integer between 5 and 200, W is O and Y is a residue derived from a reactive oligomer derived from an ethylenically unsaturated lactam containing monomer and is in a cis configuration.
8. The prepolymer of claim 1 wherein the compound has the following formula:
CH 2 ═C(CH 2 COY)COW(R 1 )(SiR 2 R 3 O) m (SiR 2 R 3 )(R 1 )WOC(CH 2 COY)C═CH 2
or
CH 2 ═C(CH 2 COY)COW(R 1 )(SiR 2 R 3 O) m (SiR 2 R 3 )(R 1 )WOCCH 2 (COY)C═CH 2
wherein R 1 is selected from the group consisting of alkylenes and alkylenes containing ether linkages, R 2 and R 3 are methyl, m is an integer between 5 and 100, W is O and Y is a residue derived from a reactive oligomer derived from an ethylenically unsaturated lactam containing monomer.
9. The prepolymer of claim 1 wherein the compound has the following formula:
YCO—CH═CHCOW(R 1 )(SiR 2 R 3 O) m (SiR 2 R 3 )(R 1 )WOCCH═CH—COY
wherein R 1 is selected from the group consisting of alkylenes and alkylenes containing ether linkages, R 2 and R 3 are methyl, m is an integer between 5 and 200, W is O and Y is a residue derived from a reactive oligomer derived from N-vinylpyrrolidone and is in a trans configuration.
10. The prepolymer of claim 1 wherein the compound has the following formula:
YCO—CH═CHCOW(R 1 )(SiR 2 R 3 O) m (SiR 2 R 3 )(R 1 )WOCCH═CH—COY
wherein R 1 is selected from the group consisting of alkylenes and alkylenes containing ether linkages, R 2 and R 3 are methyl, m is an integer between 5 and 200, W is O and Y is a residue derived from a reactive oligomer derived from N-vinylpyrrolidone and is in a cis configuration.
11. The prepolymer of claim 1 wherein the compound has the following formula:
CH 2 ═C(CH 2 COY)COW(R 1 )(SiR 2 R 3 O) m (SiR 2 R 3 )(R 1 )WOC(CH 2 COY)C═CH 2
or
CH 2 ═C(CH 2 COY)COW(R 1 )(SiR 2 R 3 O) m (SiR 2 R 3 )(R 1 )WOCCH 2 (COY)C═CH 2
wherein R 1 is selected from the group consisting of alkylenes and alkylenes containing ether linkages, R 2 and R 3 are methyl, m is an integer between 5 and 100, W is O and Y is a residue derived from a reactive oligomer derived from N-vinylpyrrolidone.