Process for making cationic hydrophilic siloxanyl monomers
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 monomers 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 polymeric compositions comprise polymerized cationic hydrophilic siloxanyl monomers prepared by the process disclosed herein.
1. A biomedical device obtained from a polymerization product of a monomer mixture comprising a water extractable biomedical device forming cationic non-hydroxyl-containing organosilicon-containing monomer, wherein the water extractable medical device forming cationic non-hydroxyl-containing organosilicon-containing monomer is obtained by the method comprising
(a) dissolving a hydride containing siloxane compound in a solvent or combination of solvents;
(b) treating the dissolved hydride containing siloxane compound with an allylic halide and a hydrosilation catalyst to form a first reaction mixture;
(c) heating the first reaction mixture under a nitrogen atmosphere for a sufficient time to result in the quantitative loss of reactants as determined by appropriate analytical technique thus providing a monomer mixture;
(d) cooling the monomer mixture;
(e) concentrating the cooled mixture;
(f) dissolving the cooled mixture in a solvent appropriate for nucleophilic substitution;
(g) treating the cooled mixture containing the solvent appropriate for nucleophilic substitution with a tertiary amino-vinyl compound to form a second reaction mixture;
(h) heating the second reaction mixture at a temperature sufficient to promote reaction without causing gelation;
(i) removing any remaining solvent to provide a product containing material; and,
(j) purifying the product containing material to yield the water extractable medical device forming cationic non-hydroxyl-containing organosilicon-containing monomer.
2. The biomedical device of claim 1 , wherein the hydride containing siloxane compound is tris(trimethylsiloxy) silane or a hydride terminated poly(dimethylsiloxane), the allylic halide is allyl bromide and the tertiary amino-vinyl compound is 2-(dimethylamino)ethyl methacrylate.
3. The biomedical device of claim 1 , wherein the monomer mixture further comprises a second comonomer.
4. The biomedical device of claim 1 , wherein the second monomer is selected from the group consisting of an unsaturated carboxylic acid, acrylic substituted alcohol, vinyl lactam, acrylamide, methacrylate, hydrophilic vinyl carbonate, hydrophilic vinyl carbamate monomer, hydrophilic oxazolone monomer and mixtures thereof.
5. The biomedical device of claim 3 , wherein the second monomer is selected from the group consisting of methacrylic acid, acrylic acid, 2-hydroxyethylmethacrylate, 2-hydroxyethylacrylate, N-vinyl pyrrolidone, N-vinyl caprolactone, methacrylamide, N,N-dimethylacrylamide, ethylene glycol dimethacrylate, methyl methacrylate, allyl methacrylate, 3-methacryloylpropyl tris(trimethylsiloxyl) silane and mixtures thereof.
6. The biomedical device of claim 1 , wherein the device is a contact lens.
7. The biomedical device of claim 6 , wherein the contact lens is a rigid gas permeable contact lens, a soft contact lens or a hydrogel contact lens.
8. The biomedical device of claim 1 , wherein the device is an intraocular lens.
9. The biomedical device of claim 1 , wherein the device is a corneal implant.
10. A biomedical device obtained from a polymerization product comprising a monomer mixture comprising a cationic non-hydroxyl-containing organosilicon-containing monomer, wherein the cationic organosilicon-containing monomer is obtained by a method comprising:
(a) treating a solution comprising a hydride containing siloxane compound in a first solvent with an allylic halide in the presence of a hydrosilation catalyst; and
(b) treating the product of step (a) with a tertiary amino-vinyl compound.
11. The biomedical device of claim 10 , wherein the hydride containing siloxane compound is tris(trimethylsiloxy) silane or a hydride terminated poly(dimethylsiloxane), the allylic halide is allyl bromide and the tertiary amino-vinyl compound is 2-(dimethylamino)ethyl methacrylate.
12. The biomedical device of claim 10 , wherein the monomer mixture further comprises a second comonomer.
13. The biomedical device of claim 10 , wherein the second comonomer is selected from the group consisting of an unsaturated carboxylic acid, acrylic substituted alcohol, vinyl lactam, acrylamide, methacrylate, hydrophilic vinyl carbonate, hydrophilic vinyl carbamate monomer, hydrophilic oxazolone monomer and mixtures thereof.
14. The biomedical device of claim 12 , wherein the monomer mixture further comprising in addition to the second monomer a hydrophobic monomer and a hydrophilic monomer.
15. The biomedical device of claim 10 , wherein the device is a contact lens.
16. The biomedical device of claim 10 , wherein the device is selected from the group consisting of heart valves, intraocular lenses, films, surgical devices, vessel substitutes, intrauterine devices, membranes, diaphragms, surgical implants, blood vessels, artificial ureters, artificial breast tissue, membranes for kidney dialysis machines, membranes for heart/lung machines, catheters, mouth guards, denture liners, ophthalmic devices, and contact lenses.