Brush copolymers
View Patent ↗Brush copolymers containing (a) monomeric units derived from an ethylenically unsaturated-containing monomer containing one or more boronic acid moieties; and (b) monomeric units derived from an ethylenically unsaturated-containing macromonomer having hydrophilic units and boronic acid units are disclosed.
1. A brush copolymer comprising (a) monomeric units derived from an ethylenically unsaturated boronic acid-containing monomer and (b) a macromonomer having hydrophilic units and boronic acid units.
2. The brush copolymer of claim 1 , having a backbone of the monomeric units derived from an ethylenically unsaturated boronic acid-containing monomer and bristles of macromonomer having hydrophilic units and boronic acid units.
3. The brush copolymer of claim 1 , wherein the macromonomer comprises hydrophilic units derived from a hydrophilic monomer selected from the group consisting of unsaturated carboxylic acids, vinyl lactams, amides, polymerizable amines, vinyl carbonates, vinyl carbamates, oxazolone monomers and mixtures thereof, and boronic acid units derived from a monomer selected from the group consisting of 4-vinylphenylboronic acid, 3-methacrylamidophenylboronic acid, 3-acrylamidophenylboronic acid and mixtures thereof.
4. The brush copolymer of claim 1 , wherein the macromonomer has a number average molecular weight of about 500 to about 200,000.
5. The brush copolymer of claim 1 , wherein the macromonomer comprises about 80 to about 99 mole percent of the hydrophilic units and about 1 to about 20 mole percent of the boronic acid-containing monomeric units.
6. The brush copolymer of claim 2 , 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 brush copolymer water-soluble.
7. A biomedical device having a coating on a surface thereof, the coating comprising the brush copolymer of claim 1 .
8. A biomedical device having a coating on a surface thereof, the coating comprising the brush copolymer of claim 2 .
9. The biomedical device of claim 7 , wherein the macromonomer comprises hydrophilic units derived from a hydrophilic monomer selected from the group consisting of unsaturated carboxylic acids, vinyl lactams, amides, polymerizable amines, vinyl carbonates, vinyl carbamates, oxazolone monomers and mixtures thereof, and boronic acid units derived from a monomer selected from the group consisting of 4-vinylphenylboronic acid, 3-methacrylamidophenylboronic acid, 3-acrylamidophenylboronic acid and mixtures thereof.
10. The biomedical device of claim 7 , wherein the macromonomer has a number average molecular weight of about 500 to about 200,000.
11. The biomedical device of claim 7 , wherein the macromonomer comprises about 80 to about 99 mole percent of the hydrophilic units and about 1 to about 20 mole percent of the boronic acid-containing monomeric units.
12. The biomedical device of claim 7 , wherein the brush copolymer further comprises monomeric units derived from an ethylenically unsaturated monomer containing a tertiary-amine moiety.
13. The biomedical device of claim 7 , wherein the brush copolymer further comprises monomeric units derived from an ethylenically unsaturated monomer containing a hydrophilic moiety capable of rendering the brush copolymer water-soluble.
14. The biomedical device of claim 8 , 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 brush copolymer water-soluble.
15. The biomedical device of claim 7 , wherein the brush copolymer comprises
about 1 to about 20 mole percent of the ethylenically unsaturated boronic acid-containing monomeric units,
about 1 to about 20 mole percent of the macromonomer having hydrophilic units and boronic acid units,
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 brush copolymer water-soluble.
16. The biomedical device of claim 7 , wherein the biomedical device is an ophthalmic lens.
17. The biomedical device of claim 16 , wherein the ophthalmic lens is a contact lens or an intraocular lens.
18. 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 one or more brush copolymers comprising (a) monomeric units derived from an ethylenically unsaturated boronic acid-containing monomer; and (b) monomeric units derived from an macromonomer having hydrophilic units and boronic acid units, 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.