Packaging solutions
View Patent ↗Packaging systems for storing ophthalmic devices such as contact lenses and to methods for packaging such ophthalmic devices with solutions to improve the comfort of the lenses during wear are disclosed. A packaging system includes an ophthalmic device stored in an aqueous packaging solution comprising a brush copolymer comprising (a) monomeric units derived from an ethylenically unsaturated monomer containing one or more boronic acid moieties; and (b) monomeric units derived from an ethylenically unsaturated-containing hydrophilic macromonomer.
1. A method of preparing a package comprising a storable, sterile ophthalmic device, the method comprising:
(a) immersing an ophthalmic device in an aqueous packaging solution comprising a brush copolymer prepared by reacting a 3-methacrylamidophenylboronic acid with a methacrylated PVP macromer to provide a hydrophilic polymer intermediate; reacting the hydrophilic polymer intermediate with a triethylamine followed by the reactive addition of a methacryloyl chloride; removal of any Triethylamine hydrochloride formed; and isolation of a methacrylated polymeric backbone formed there by; and reacting the methacrylated polymeric backbone with a 3-methacylamidophenyl boronic acid and a DMA to provide a brush copolymer comprising (i) monomeric units derived from an ethylenically unsaturated monomer containing one or more boronic acid moieties; and (ii) monomeric units derived from an ethylenically unsaturated-containing hydrophilic macromonomer, wherein the solution has an osmolality of at least about 200 mOsm/kg and a pH in the range of about 6 to about 9;
(b) packaging the solution and the device in a manner preventing contamination of the device by microorganisms; and
(c) sterilizing the packaged solution and device.
2. The method of claim 1 , wherein the ophthalmic device is a contact lens.
3. The method of claim 1 , wherein the ophthalmic device is a silicone hydrogel contact lens.
4. The method of claim 1 , wherein the brush copolymer has a backbone of the monomeric units derived from an ethylenically unsaturated monomer containing one or more boronic acid moieties; and bristles of the monomeric units derived from an ethylenically unsaturated-containing hydrophilic macromonomer.
5. The method of claim 4 , wherein the backbone further comprises monomeric units derived from an ethylenically unsaturated monomer containing a tertiary-amine moiety; and monomeric units derived from an ethylenically unsaturated monomer containing a hydrophilic moiety capable of rendering the copolymer water-soluble.
6. The method of claim 1 , wherein the ethylenically unsaturated monomer containing one or more boronic acid moieties comprises an ethylenically unsaturated containing aryl boronic acid.
7. The method of claim 1 , wherein the ethylenically unsaturated monomer containing one or more boronic acid moieties is selected from the group consisting of 4-vinylphenylboronic acid, 3-methacrylamidophenylboronic acid, 3-acrylamidophenylboronic acid and mixtures thereof.
8. The method of claim 1 , wherein the hydrophilic macromonomer comprises units derived from a hydrophilic monomer selected from the group consisting of an unsaturated carboxylic acid, vinyl lactam, amide, polymerizable amine, vinyl carbonate, vinyl carbamate, oxazolone monomer and mixtures thereof.
9. The method of claim 1 , wherein the hydrophilic macromonomer is made using atom transfer radical polymerization (ATRP) or reversible addition-fragmentation chain transfer (RAFT) polymerization.
10. The method of claim 1 , wherein the hydrophilic macromonomer has a number average molecular weight of about 500 to about 200,000.
11. The method of claim 1 , wherein the brush copolymer further comprises monomeric units derived from an ethylenically unsaturated monomer containing a tertiary-amine moiety.
12. The method of claim 1 , wherein the brush copolymer further comprises monomeric units derived from an ethylenically unsaturated monomer containing a hydrophilic moiety capable of rendering the copolymer water-soluble.
13. The method of claim 1 , wherein the hydrophilic moiety is derived from a hydrophilic monomer selected from the group consisting of N-vinyl pyrrolidone, N-vinyl-N-methyl acetamide, N,N-dimethyl methacrylamide, N,N-dimethylacrylamide, and mixtures thereof.
14. The method of claim 1 , wherein the brush copolymer comprises about 1 to about 20 mole percent of the boronic acid-containing monomeric units, about 1 to about 20 mole percent of the monomeric units derived from an ethylenically unsaturated hydrophilic macromonomer, about 1 to about 20 mole percent of monomeric units derived from an ethylenically unsaturated monomer containing a tertiary-amine moiety, and about 40 to about 90 mole percent of monomeric units derived from an ethylenically unsaturated monomer containing a hydrophilic moiety capable of rendering the copolymer water-soluble.
15. The method of claim 1 , wherein the solution does not contain an effective disinfecting amount of a disinfecting agent.
16. The method of claim 1 , wherein the solution does not contain a germicide compound.
17. A packaging system for the storage of an ophthalmic device comprising a sealed container containing one or more unused ophthalmic devices immersed in an aqueous packaging solution comprising a brush copolymer prepared by reacting a 3-methacrylamidophenylboronic acid with a methacrylated PVP macromer to provide a hydrophilic polymer intermediate; reacting the hydrophilic polymer intermediate with a triethylamine followed by the reactive addition of a methacryloyl chloride; removal of any Triethylamine hydrochloride formed; and isolation of a methacrylated polymeric backbone formed there by; and reacting the methacrylated polymeric backbone with a 3-methacylamidophenyl boronic acid and a DMA to provide a brush copolymer comprising (i) monomeric units derived from an ethylenically unsaturated monomer containing one or more boronic acid moieties; and (ii) monomeric units derived from an ethylenically unsaturated-containing hydrophilic macromonomer, wherein the solution has an osmolality of at least about 200 mOsm/kg, a pH of about 6 to about 9 and is heat sterilized.
18. The packaging system of claim 17 , wherein the ophthalmic device is a contact lens.
19. The packaging system of claim 17 , wherein the package is heat sterilized subsequent to sealing of the package and the solution does not contain an effective disinfecting amount of a disinfecting agent or a germicide compound.
20. A packaging system for the storage of an ophthalmic device comprising:
(a) an aqueous packaging solution comprising a brush copolymer prepared by reacting a 3-methacrylamidophenylboronic acid with a methacrylated PVP macromer to provide a hydrophilic polymer intermediate; reacting the hydrophilic polymer intermediate with a triethylamine followed by the reactive addition of a methacryloyl chloride; removal of any Triethylamine hydrochloride formed; and isolation of a methacrylated polymeric backbone formed there by; and reacting the methacrylated polymeric backbone with a 3-methacylamidophenyl boronic acid and a DMA to provide a brush copolymer comprising (i) monomeric units derived from an ethylenically unsaturated monomer containing one or more boronic acid moieties; and (ii) monomeric units derived from an ethylenically unsaturated-containing hydrophilic macromonomer, wherein the solution has an osmolality of at east about 200 mOsm/kg and a pH in the range of about 6 to about 9;
(b) at least one ophthalmic device; and
(c) a container for holding the solution and ophthalmic device sufficient to preserve the sterility of the solution and ophthalmic device, wherein the solution does not contain an effective disinfecting amount of a disinfecting agent.