SILICONE BIOMEDICAL DEVICE WITH POLYMERIZABLE GLYCOSAMINOGLYCANS

1 . A silicone biomedical device comprising a polymerization product of a biomedical device-forming mixture comprising:

(a) one or more grafted glycosaminoglycan polymers comprising a glycosaminoglycan having a polymer backbone and one or more side chains comprising an ethylenically unsaturated reactive-containing residue grafted onto the polymer backbone; and

(b) one or more silicone biomedical device-forming monomers comprising at least one hydrogen donating group.

2 . The silicone biomedical device according to claim 1 , wherein the one or more grafted glycosaminoglycan polymers are selected from the group consisting of chondroitin, chondroitin sulfate, dermatan, dermatan sulfate, heparin, heparan sulfate, heparosan, hyaluronan, and hyaluronic acid or a salt thereof.

3 . The silicone biomedical device according to claim 1 , wherein the one or more grafted glycosaminoglycan polymers have a degree of grafting ranging from about 2% to about 30%.

4 . The silicone biomedical device according to claim 1 , wherein the ethylenically unsaturated reactive-containing residue is a (meth)acrylate-containing residue.

5 . The silicone biomedical device according to claim 4 , wherein the one or more grafted glycosaminoglycan polymers have a degree of methacrylation ranging from about 0.5% to about 50%.

6 . The silicone biomedical device according to claim 1 , wherein the glycosaminoglycan is hyaluronic acid or a salt thereof and the ethylenically unsaturated reactive-containing residue is a (meth)acrylate-containing residue.

7 . The silicone biomedical device according to claim 1 , wherein the at least one hydrogen donating group include one or more of a hydroxy group, an amino group, a SH group and a carboxyl group.

8 . The silicone biomedical device according to claim 1 , wherein the at least one hydrogen donating group is OH or NH.

9 . The silicone biomedical device according to claim 1 , wherein the one or more silicone biomedical device-forming monomers comprise are one or more hydroxyl-functionalized silicone biomedical device-forming monomers.

10 . The silicone biomedical device according to claim 9 , wherein the one or more hydroxyl-functionalized silicone biomedical device-forming monomers comprise one or more monomers of Formulae I, II or III:

wherein:

n is an integer between 3 and 35, or between 4 and 25;

R 1 is hydrogen or C 1-6 alkyl;

R 2 , R 3 , and R 4 , are independently a substituted or unsubstituted C 1-6 alkyl group, a C 1-6 triC 1-6 alkylsiloxy group, a phenyl group, a naphthyl group, a substituted phenyl group, and a substituted naphthyl group;

R 5 is a hydroxyl group, an alkyl group containing one or more hydroxyl groups, or (CH 2 (CR 9 R 10 ) y O) x )—R 11 wherein y is 1 to 5, x is an integer of 1 to 100;

R 6 is a divalent group comprising up to 20 carbon atoms;

R 7 is a free radical reactive group;

R 8 is a divalent or trivalent group comprising up to 20 carbon atoms; and

R 9 -R 11 are independently hydrogen, an alkyl group having up to 10 carbon atoms optionally substituted with at least one polar functional group, or:

wherein R 1 , R 5 , R 7 and R 8 have the aforestated meanings.

11 . The silicone biomedical device according to claim 1 , wherein the one or more silicone biomedical device-forming monomers comprise one or more amino-functionalized silicone biomedical device-forming monomers.

12 . The silicone biomedical device according to claim 11 , wherein the one or more amino-functionalized silicone biomedical device-forming monomers are represented by a structure of Formula IV:

wherein R 1 , R 2 , R 3 and R 4 are independently hydrogen, an alkyl group, a halo alkyl group, a cycloalkyl group, a heterocycloalkyl group, an alkenyl group, a haloalkenyl group, an aryl group and a heteroaryl group; R 5 , R 6 and R 7 are independently a straight or branched alkyl group; x is from 1 to 6; and y is from 3 to 7.

13 . The silicone biomedical device according to claim 1 , wherein the one or more silicone biomedical device-forming monomers have a ratio of silicon atoms to hydrogen donating groups of from about 1:1 to about 9:1.

14 . The silicone biomedical device according to claim 1 , wherein the one or more silicone biomedical device-forming monomers have a ratio of silicon atoms to hydrogen donating groups of from about 1:1 to about 1:5.

15 . The silicone biomedical device according to claim 1 , wherein the silicone biomedical device-forming mixture comprises:

about 0.1 to about 1.0 wt. %, based on the total weight of the silicone biomedical device-forming mixture, of the one or more grafted glycosaminoglycan polymers; and

about 1 to about 30 wt. %, based on the total weight of the silicone biomedical device-forming mixture, of the one or more silicone biomedical device-forming monomers.

16 . The silicone biomedical device according to claim 1 , wherein the silicone biomedical device-forming mixture further comprises one or more non-silicone biomedical device-forming monomers.

17 . The silicone biomedical device according to claim 1 , having a water content of at least about 70 wt. %.

18 . The silicone biomedical device according to claim 1 , which is optically clear.

19 . The silicone biomedical device according to claim 1 , which is one of a silicone contact lens, a silicone intraocular lens or a silicone hydrogel.

20 . A method for making a silicone biomedical device comprising:

(a) providing a silicone biomedical device-forming mixture comprising (i) one or more grafted glycosaminoglycan polymers comprising a glycosaminoglycan having a polymer backbone and one or more side chains comprising an ethylenically unsaturated reactive-containing residue grafted onto the polymer backbone, and (ii) one or more silicone biomedical device-forming monomers comprising at least one hydrogen donating group;

(b) subjecting the mixture to polymerization conditions to provide a polymerized silicone biomedical device; and

(c) hydrating the polymerized silicone biomedical device.