Siloxane prepolymer containing pendant cationic and polymerizable groups
View Patent ↗The present invention relates to polymeric compositions useful in the manufacture of biocompatible medical devices. More particularly, the present invention relates to certain cationic random copolymers capable of polymerization to form polymeric compositions having desirable physical characteristics useful in the manufacture of ophthalmic devices. Such properties include the ability to extract the polymerized medical devices with water. This avoids the use of organic solvents as is typical in the art. The polymer compositions comprise polymerized siloxane prepolymer containing pendant cationic and polymerizable groups.
1. A contact lens comprising a polymerized monomer mixture comprising a cationic random copolymer bearing pendant free radical polymerizable cationic groups and at least a second monomer, wherein the at least one cationic random copolymer is of formula (I):
wherein R1 is selected from the group consisting of the following radicals of formulae II-IV:
with the proviso that R1 is at least one radical of formula IV, and further wherein x is 0 to 1000, y is 1 to 300, L can be the same or different and is selected from the group consisting of urethanes, carbonates, carbamates. carboxyl ureidos, sulfonyls, a straight or branched C1-C30 alkyl group, a C1-C30 fluoroalkyl group, a C1-C20 ester group, an alkyl ether, cycloalkyl ether, cycloalkenyl ether, aryl ether, arylalkyl ether, a polyether containing group, an ureido group, an amide group, an amine group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C3-C30 cycloalkenyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 arylalkyl group, a substituted or unsubstituted C5-C30 heteroaryl group, a substituted or unsubstituted C3-C30 heterocyclic ring, a substituted or unsubstituted C4-C30 heterocyclolalkyl group, a substituted or unsubstituted C6-C30 heteroarylalkyl group, a C5-C30 fluoroaryl group, or a hydroxyl substituted alkyl ether and combinations thereof; X is at least a single charged counter ion;
each R2, R3 and R5 are independently hydrogen, a straight or branched C1-C30 alkyl group, a C1-C30 fluoroalkyl group, a C1-C20 ester group, an alkyl ether, cycloalkyl ether, cycloalkenyl ether, aryl ether, arylalkyl ether, a polyether containing group, an ureido group, an amide group, an amine group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituded C3-C30 cycloalkenyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 arylqlkyl group, a substituted or unsubstituted C5-C30 heteroaryl group, a substituted or C3-C30 heterocyclic ring, a substituted or unsubstituted C4-C30 heterocyclolalkyl group, a substituted or unsubstituted C6-C30 heteroarylalkyl group, fluorine, a C5-C30 fluoroaryl group, or a hydroxyl group; and each R4 is independently H or a methyl radical, wherein the contact lens is a soft contact tens.
2. The soft contact lens of claim 1 , wherein the soft contact lens is a hydrogel contact lens.
3. The hydrogel soft contact lens of claim 2 , wherein the second monomer is selected from the group consisting of methacrylic acid, acrylic acid, 2-hydroxyethylmethacrylate, 2-hydroxyethylacrylate, N-vinyl pyrrolidone (NVP), vinyl lactams, methacrylamide, N,N-dimethylacrylamide, ethylene glycol dimethylacrylate, methyl methacrylate, allyl methacrylate, methacryloxypropyl tris(trimethylsiloxy)silane and mixtures thereof.