IP Library Granted Patent US 7,022,749
Granted Patent B2
US 7,022,749 · App. 10/665,957 · Granted Apr 4, 2006

High refractive index aromatic-based siloxane difunctional macromonomers

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Quick Facts
Patent No.
US 7,022,749
App. No.
10/665,957
Granted
Apr 4, 2006
Kind
B2
Abstract

Optically transparent, relatively high refractive index polymeric compositions and ophthalmic devices such as intraocular lenses, corneal inlays and contact lenses made therefrom are described herein. The preferred polymeric compositions are produced through the polymerization of one or more aromatic-based siloxane macromonomers or the copolymerization of one or more aromatic-based siloxane macromonomers with one or more non-siloxy aromatic-based monomers, non-aromatic-based hydrophobic monomers or non-aromatic-based hydrophilic monomers.

Claims (55)

1. A method of producing ophthalmic devices from polymeric compositions, said method comprising:

casting one or more of said polymeric compositions in a form of a rod;

lathing or machining said rod into disks; and

lathing or machining said disks into ophthalmic devices;

wherein said polymeric compositions are produced through a polymerization of one or more aromatic-based siloxane macromonomers having a formula of

wherein the R groups are the same or different aromatic-based substituents; each R group comprises an aromatic group having a linking group that covalently attaches the aromatic group to a silicon atom; R 1 is an aromatic-based substituent or an alkyl; x is a non-negative integer; and y and u are natural numbers; and wherein an attachment of the aromatic group to the silicon atom results from a hydrosilylation of an allylic functional group on the aromatic group.

2. A method of producing ophthalmic devices from polymeric compositions, said method comprising:

pouring one or more of said polymeric compositions into a mold prior to curing;

curing said one or more polymeric compositions; and

removing said one or more polymeric compositions from said mold following curing thereof;

wherein said polymeric compositions are produced through a polymerization of one or more aromatic-based siloxane macromonomers having a formula of

wherein the R groups are the same or different aromatic-based substituents; each R group comprises an aromatic group having a linking group that covalently attaches the aromatic group to a silicon atom; R 1 is an aromatic-based substituent or an alkyl; x is a non-negative integer; and y, and u are natural numbers; and wherein an attachment of the aromatic group to the silicon atom results from a hydrosilylation of an allylic functional group on the aromatic group.

3. A method of producing ophthalmic devices from polymeric compositions, said method comprising:

casting one or more of said polymeric compositions in a form of a rod;

lathing or machining said rod into disks; and

lathing or machining said disks into ophthalmic devices;

wherein said polymeric compositions are produced through a polymerization of one or more aromatic-based siloxane macromonomers having a formula of

with one or more non-siloxy aromatic-based monomers,

wherein the R groups are the same or different aromatic-based substituents; each R group comprises an aromatic group having a linking group that covalently attaches the aromatic group to a silicon atom; R 1 is an aromatic-based substituent or an alkyl; x is a non-negative integer; and y and u are natural numbers; and wherein an attachment of the aromatic group to the silicon atom results from a hydrosilylation of an allylic functional group on the aromatic group.

4. A method of producing ophthalmic devices from polymeric compositions, said method comprising:

casting one or more of said polymeric compositions in a form of a rod;

lathing or machining said rod into disks; and

lathing or machining said disks into ophthalmic devices;

wherein said polymeric compositions are produced through a polymerization of one or more aromatic-based siloxane macromonomers having a formula of

with one or more non-aromatic-based hydrophobic monomers,

wherein the R groups are the same or different aromatic-based substituents; each R group comprises an aromatic group having a linking group that covalently attaches the aromatic group to a silicon atom; R 1 is an aromatic-based substituent or an alkyl; x is a non-negative integer; and y, and u are natural numbers; and wherein an attachment of the aromatic group to the silicon atom results from a hydrosilylation of an allylic functional group on the aromatic group.

5. A method of producing ophthalmic devices from polymeric compositions, said method comprising:

casting one or more of said polymeric compositions in a form of a rod;

lathing or machining said rod into disks; and

lathing or machining said disks into ophthalmic devices;

wherein said polymeric compositions are produced through a polymerization of one or more aromatic-based siloxane macromonomers having a formula of

with one or more non-aromatic-based hydrophilic monomers,

wherein the R groups are the same or different aromatic-based substituents; each R group comprises an aromatic group having a linking group that covalently attaches the aromatic group to a silicon atom; R 1 is an aromatic-based substituent or an alkyl; x is a non-negative integer; and y, and u are natural numbers; and wherein an attachment of the aromatic group to the silicon atom results from a hydrosilylation of an allylic functional group on the aromatic group.

6. A method of producing ophthalmic devices from polymeric compositions, said method comprising:

pouring one or more of said polymeric compositions into a mold prior to curing;

curing said one or more polymeric compositions; and

removing said one or more polymeric compositions from said mold following curing thereof;

wherein said polymeric compositions are produced through a polymerization of one or more aromatic-based siloxane macromonomers having a formula of

with one or more non-siloxy aromatic-based monomers,

wherein the R groups are the same or different aromatic-based substituents; each R group comprises an aromatic group having a linking group that covalently attaches the aromatic group to a silicon atom; R 1 is an aromatic-based substituent or an alkyl; x is a non-negative integer; and y and u are natural numbers; and wherein an attachment of the aromatic group to the silicon atom results from a hydrosilylation of an allylic functional group on the aromatic group.

7. A method of producing ophthalmic devices from polymeric compositions, said method comprising:

pouring one or more of said polymeric compositions into a mold prior to curing;

curing said one or more polymeric compositions; and

removing said one or more polymeric compositions from said mold following curing thereof;

wherein said polymeric compositions are produced through a polymerization of one or more aromatic-based siloxane macromonomers having a formula of

with one or more non-aromatic-based hydrophobic monomers,

wherein the R groups are the same or different aromatic-based substituents; each R group comprises an aromatic group having a linking group that covalently attaches the aromatic group to a silicon atom; R 1 is an aromatic-based substituent or an alkyl; x is a non-negative integer; and y and u are natural numbers; and wherein an attachment of the aromatic group to the silicon atom results from a hydrosilylation of an allylic functional group on the aromatic group.

8. A method of producing ophthalmic devices from polymeric compositions, said method comprising:

pouring one or more of said polymeric compositions into a mold prior to curing;

curing said one or more polymeric compositions; and

removing said one or more polymeric compositions from said mold following curing thereof;

wherein said polymeric compositions are produced through a polymerization of one or more aromatic-based siloxane macromonomers having a formula of

with one or more non-aromatic-based hydrophilic monomers,

wherein the R groups are the same or different aromatic-based substituents; each R group comprises an aromatic group having a linking group that covalently attaches the aromatic group to a silicon atom; R 1 is an aromatic-based substituent or an alkyl: x is a non-negative integer; and y, and u are natural numbers; and wherein an attachment of the aromatic group to the silicon atom results from a hydrosilylation of an allylic functional group on the aromatic group.

9. The method of claim 1 , 2 , 3 , 4 , 5 , 6 , 7 , or 8 , wherein said ophthalmic devices are contact lenses.