Claims
- 1. A method of preparing an ophthalmic device material comprising the steps of
a) forming a copolymer having pendant oxirane groups by free radical copolymerization of a composition comprising (i) one or more aryl acrylic hydrophobic monomers of the formula 5wherein: X is H or CH3; m is2-4; Y is nothing, O, S, or NR wherein R is H, CH3, CnH2n+1(n=1-10) iso-OC3H7, C6H5, or CH2C6H5; and Ar is C6H5 which can be unsubstituted or substituted with H, CH3, C2H5, n-C3H7, iso-C3H7, OCH3, C6H11, Cl, Br, C6H5, or CH2C6H5; and (ii) a total of about 30% by weight or less of one or more compounds of the formula 6wherein X is H or CH3; and n is 1-4; and (b) reacting the copolymer containing pendant oxirane groups formed in step
(a) with one or more compounds of the formula W-T-H (III) wherein W is H, CH3(CH2)a, or Z(OCH2CH2)b; a is0-3; b is 1-5; Z is H or CH3(CH2)p; p is 0-3; and T is O, NH, S; provided that if T≠O, then W≠H.
- 2. The method of claim 1 wherein m is 2-4, Y is nothing or O, and Ar is phenyl in formula I.
- 3. The method of claim 1 wherein the one or more aryl acrylic hydrophobic compounds of formula I are selected from the group consisting of 2-phenoxyethyl acrylate; phenyl acrylate; benzyl acrylate; 2-phenylethyl acrylate; 3-phenylpropyl acrylate; 3-phenoxypropyl acrylate; 4-phenylbutyl acrylate; 4-phenoxybutyl acrylate; 4-methylphenyl acrylate; 4-methylbenzyl acrylate; 2-2-methylphenylethyl acrylate; 2-3-methylphenylethyl acrylate; 2-methylphenylethyl acrylate; 2-phenoxyethyl methacrylate; phenyl methacrylate; benzyl methacrylate; 2- phenylethyl methacrylate; 3- phenylpropyl methacrylate; 3-phenoxypropyl methacrylate; 4-phenylbutyl methacrylate; 4-phenoxybutyl methacrylate; 4-methylphenyl methacrylate; 4-methylbenzyl methacrylate; 2-2-methylphenylethyl methacrylate; 2-3-methylphenylethyl methacrylate; and 24-methylphenylethyl methacrylate.
- 4. The method of claim 1 wherein the total amount of the one or more aryl acrylic hydrophobic compounds of formula I is about 60% by weight or greater.
- 5. The method of claim 1 wherein the total amount of one or more compounds of formula II is about 10% by weight or less.
- 6. The method of claim 1 wherein T is O and a is 0-2.
- 7. The method of claim 6 wherein the one or more compounds of formula III is selected from the group consisting of methanol; ethanol; water; ethylene glycol; and diethylene glycol.
- 8. The method of claim 1 wherein the reaction of step (b) is carried out in the presence of a catalyst selected from the group consisting of sulfuric acid; paratoluene sulfonic acid; and BF3:OEt2.
- 9. The method of claim 1 wherein the reaction of step (b) is carried out in the presence of a swelling solvent.
- 10. The method of claim 9 wherein the swelling solvent is selected from the group consisting of anhydrous ketones and anhydrous C1 - C4 alcohols.
- 11. The method of claim 1 wherein the copolymer containing pendant oxirane groups formed in step (a) is swollen in a swelling solvent prior to step (b).
- 12. The method of claim 1 wherein the ophthalmic device material has a refractive index of at least about 1.50; a Tg from about −20 to +25° C.; and an elongation of at least 150%.
- 13. The method of claim 1 wherein the ophthalmic device is selected from the group consisting of intraocular lenses; contact lenses; keratoprostheses; corneal inlays; and corneal rings.
- 14. An ophthalmic device material made by the method of claim 1.
- 15. The method of claim 1 wherein T is O or S.
Parent Case Info
[0001] This application is a continuation-in-part application of U.S. Ser. No. 09/283,590, filed Apr. 1, 1999, which claims the benefit of U.S. Provisional Patent Application Serial No. 60/082,833, filed Apr. 23, 1998.
Provisional Applications (1)
|
Number |
Date |
Country |
|
60082833 |
Apr 1998 |
US |
Continuation in Parts (1)
|
Number |
Date |
Country |
Parent |
09283590 |
Apr 1999 |
US |
Child |
09954457 |
Sep 2001 |
US |