High Refractive Index Ophthalmic Device Materials

• US 20090043006A1
• Filed: 07/24/2008
• Published: 02/12/2009
• Est. Priority Date: 07/25/2007
• Status: Active Grant

• Current Assignee: Alcon Incorporated
• Original Assignee: Alcon Incorporated
• Inventors: Freeman, Charles
• Granted Patent: US 7,790,824 B2
• Time in Patent Office: Days
• US Class Current: 523/106
• CPC Class Codes: C08F 220/1808 C8-(meth)acrylate, e.g. isooctyl (meth)acrylate or 2-ethylhexyl (meth)acrylate
• CPC Class Codes: C08F 222/102 of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
• CPC Class Codes: C08L 2666/24 Graft or block copolymers according to groups C08L51/00, C08L53/00 or C08L55/02; Derivatives thereof
• CPC Class Codes: C08L 33/04 Homopolymers or copolymers of esters C08L43/04 takes precedence
• CPC Class Codes: C08L 33/14 of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
• CPC Class Codes: C08L 53/00 Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
• CPC Class Codes: C08L 71/02 Polyalkylene oxides
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

High refractive index copolymers suitable for use in ophthalmic devices are disclosed. The copolymers comprise two or more aryl hydrophobic monomers and a non-polymerizable propylene oxide-ethylene oxide-propylene oxide block copolymer surfactant having a molecular weight of approximately 3600 and approximately 40% ethylene oxide units by weight. The copolymers have a reduced tendency to form glistenings when stored in water at physiological temperatures compared to similar copolymers lacking the non-polymerizable surfactant.

Claims

1. An ophthalmic device material comprising

a) two polymerizable monomers of structure (I):

2. The ophthalmic device material of claim 1 wherein the monomers of structure (I) are selected from the group consisting of:

2-ethylphenoxy methacrylate;

2-ethylphenoxy acrylate;

phenyl methacrylate;

phenyl acrylate;

benzyl methacrylate;

benzyl acrylate;

2-phenylethyl methacrylate;

2-phenylethyl acrylate;

3-phenylpropyl methacrylate;

3-phenylpropyl acrylate;

4-phenylbutyl methacrylate;

4-phenylbutyl acrylate;

4-methylphenyl methacrylate;

4-methylphenyl acrylate;

4-methylbenzyl methacrylate;

4-methylbenzyl acrylate;

2-2-methylphenylethyl methacrylate;

2-2-methylphenylethyl acrylate;

2-3-methylphenylethyl methacrylate;

2-3-methylphenylethyl acrylate;

2-4-methylphenylethyl methacrylate;

2-4-methylphenylethyl acrylate;

2-(4-propylphenyl)ethyl methacrylate;

2-(4-propylphenyl)ethyl acrylate;

2-(4-(1-methylethyl)phenyl)ethyl methacrylate;

2-(4-(1-methylethyl)phenyl)ethyl acrylate;

2-(4-methoxyphenyl)ethyl methacrylate;

2-(4-methoxyphenyl)ethyl acrylate;

2-(4-cyclohexylphenyl)ethyl methacrylate;

2-(4-cyclohexylphenyl)ethyl acrylate;

2-(2-chlorophenyl)ethyl methacrylate;

2-(2-chlorophenyl)ethyl acrylate;

2-(3-chlorophenyl)ethyl methacrylate;

2-(3-chlorophenyl)ethyl acrylate;

2-(4-chlorophenyl)ethyl methacrylate;

2-(4-chlorophenyl)ethyl acrylate;

2-(4-bromophenyl)ethyl methacrylate;

2-(4-bromophenyl)ethyl acrylate;

2-(3-phenylphenyl)ethyl methacrylate;

2-(3-phenylphenyl)ethyl acrylate;

2-(4-phenylphenyl)ethyl methacrylate;

2-(4-phenylphenyl)ethyl acrylate;

2-(4-benzylphenyl)ethyl methacrylate; and

2-(4-benzylphenyl)ethyl acrylate.

3. The ophthalmic device material of claim 1 wherein m is 2-4, Y is nothing or O, and Ar is phenyl.

4. The ophthalmic device material of claim 3 wherein the two monomers of structure (I) are 2-phenylethyl acrylate and 2-phenylethyl methacrylate.

5. The ophthalmic device material of claim 1 wherein the amount of non-polymerizable propylene oxide-ethylene oxide-propylene oxide block copolymer surfactant is 4.5-10.5% by weight.

6. The ophthalmic device material of claim 1 wherein the polymerizable cross-linking agent is selected from the group consisting of:

ethylene glycol dimethacrylate;

diethylene glycol dimethacrylate;

allyl methacrylate;

1,3-propanediol dimethacrylate;

1,6-hexanediol dimethacrylate;

1,4-butanediol dimethacrylate; and

their corresponding acrylates.

7. The ophthalmic device material of claim 1 wherein the polymerizable cross-linking agent is present in an amount of 0.2-0.5% by weight.

8. The ophthalmic device material of claim 1 wherein the polymerizable cross-linking agent is present in an amount of 2-0.5% by weight.

9. The ophthalmic device material of claim 1 further comprising an ultraviolet absorbing compound.

10. The ophthalmic device material of claim 1 further comprising a blue-light blocking dye.

11. An ophthalmic device comprising the ophthalmic device material of claim 1, wherein the ophthalmic device is selected from the group consisting of:

intraocular lenses;

contact lenses;

keratoprostheses;

intracorneal lenses;

corneal inlays or rings; and

glaucoma filtration devices.