Renewable polymeric lens coating
View Patent ↗Disclosed are biomedical devices having a hydrophilic coating on a portion of a surface thereof, the biomedical device comprising: (a) a biomedical device obtained from a polymerization product of a monomeric mixture comprising (i) a polymerizable monomer containing a boronic acid moiety and an electron withdrawing moiety; and (ii) a biomedical device-forming comonomer; and (b) a hydrophilic reactive polymer having complementary reactive functionalities along the polymer chain, wherein the complementary reactive functionalities along the polymer chain of the hydrophilic reactive polymer of (b) bind with the boronic acid moieties of the biomedical device of (a), thereby producing a biocompatible coating which can be removed and re-applied to restore the surface properties of the biomedical device to substantially as-new condition. Methods for treating the biomedical device are also disclosed.
1. A biomedical device including a shaped article that is a polymerization product of a monomeric mixture comprising (i) a polymerizable monomer containing a boronic acid moiety and an electron withdrawing moiety; and (ii) a biomedical device-forming comonomer; said biomedical device including, on a surface of said shaped article, a hydrophilic reactive polymer having complementary reactive functionalities along the polymer chain, wherein the complementary reactive functionalities along the polymer chain of the hydrophilic reactive polymer bind the boronic acid moieties of the shaped article, thereby producing a biocompatible coating which can be removed and re-applied to restore the surface properties of the biomedical device to, and wherein the hydrophilic reactive polymer is selected from the group consisting of a copolymer derived from 2-vinyl-4,4-dimethyl-2-oxazolin-5-one and dimethylacrylamide, and a copolymer obtained by hydrolyzing a polymerization product of a monomer mixture comprising an ethylenically unsaturated epoxy-containing monomer.
2. The biomedical device of claim 1 , wherein the electron withdrawing moiety is —CF 3 , —NO 2 , —F, —Cl or —Br.
3. The biomedical device of claim 1 , wherein the polymerizable monomer containing a boronic acid moiety and an electron withdrawing moiety comprises a polymerizable ethylenically unsaturated containing aryl boronic acid.
4. The biomedical device of claim 1 , wherein the polymerizable monomer containing a boronic acid moiety is derived from 3-vinylphenylboronic acid or 3-methacrylamidophenylboronic acid.
5. The biomedical device of claim 1 , wherein the biomedical device-forming comonomer is a silicone-containing monomer.
6. The biomedical device of claim 1 , wherein the monomeric mixture further comprises at least one member selected from the group consisting of a hydrophilic monomer and a hydrophobic monomer.
7. The biomedical device of claim 6 , wherein the hydrophilic monomer is selected from the group consisting of an unsaturated carboxylic acid, vinyl lactam, amide, polymerizable amine, vinyl carbonate, vinyl carbamate, oxazolone monomer and mixtures thereof.
8. The biomedical device of claim 6 , wherein the hydrophilic monomer is selected from the group consisting of 2-hydroxyethylmethacrylate, 2-hydroxyethylacrylate, glyceryl methacrylate, N-vinyl pyrrolidone, N-vinyl-N-methyl acetamide, N,N-dimethyl methacrylamide, N,N-dimethylacrylamide, acrylic acid, methacrylic acid and mixtures thereof.
9. The biomedical device of claim 1 , wherein component (i) comprises about 0.1 to about 10 weight percent of the mixture and the biomedical device-forming comonomer component (ii) comprises about 5 to about 20 weight percent of the mixture.
10. The biomedical device of claim 1 , wherein the hydrophilic reactive polymer is a copolymer derived from 2-vinyl-4,4-dimethyl-2-oxazolin-5-one and dimethylacrylamide.
11. The biomedical device of claim 1 , wherein the hydrophilic reactive polymer is a copolymer obtained by hydrolyzing a polymerization product of a monomer mixture comprising an ethylenically unsaturated epoxy-containing monomer.
12. The biomedical device of claim 11 , wherein the copolymer further comprises monomeric units derived from a hydrophilic monomer selected from the group consisting of an aprotic hydrophilic monomer, protic hydrophilic monomer and mixtures thereof.
13. The biomedical device of claim 12 , wherein the aprotic hydrophilic monomer is selected from the group consisting of N,N-dimethylacrylamide, N,N-dimethyl methacrylamide, N-methylmethacrylamide, N-methylacrylamide, N-vinylpyrrolidinone, methoxypolyoxyethylene methacrylates and mixtures thereof.
14. The biomedical device of claim 12 , wherein the protic hydrophilic monomer is selected from the group consisting of methacrylic acid, 2-hydroxyethyl methacrylate and mixtures thereof.
15. The biomedical of claim 1 , wherein the biomedical device is in the form of a contact lens.