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 method of preparing a water extractable medical device forming monomer, the method comprising:
dissolving a hydride containing siloxane compound in a solvent or combination of solvents;
treating the dissolved hydride containing siloxane compound with an allylic halide and a hydrosilation catalyst to form a first reaction mixture;
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;
cooling the monomer mixture;
concentrating the cooled mixture;
dissolving the cooled mixture in a solvent appropriate for nucleophilic substitution;
treating the cooled mixture containing the solvent appropriate for nucleophilic substitution with a tertiary amino-vinyl compound to form a second reaction mixture;
heating the second reaction mixture at a temperature sufficient to promote reaction without causing gelation;
removing any remaining solvent to provide a product containing material; and,
purifying the product containing material to yield a water extractable medical device forming monomer.
2. The method of claim 1 wherein the hydride containing siloxane compound is tris(trimethylsiloxy) silane or a hydride terminated poly(dimethylsiloxane).
3. The method of claim 2 wherein the allylic halide is allyl bromide.
4. The method of claim 1 wherein the tertiary amino-vinyl compound is 2-(dimethylamino)ethyl methacrylate.
5. The method of claim 1 further comprising the step of reacting the water extractable medical device forming monomer with a second comonomer under polymerization conditions.
6. The method of claim 5 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.
7. The method of claim 5 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.
8. The method of claim 5 further comprising the step of extracting the polymerization product.
9. The method of claim 8 wherein the step of extracting is performed with non-flammable solvents.
10. The method of claim 8 wherein the step of extracting is performed with water.
11. The method of claim 8 further comprising the step of packaging and sterilizing the extracted polymerization product.
12. A method for preparing a cationic organosilicon-containing monomer, the 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.
13. The method of claim 12 wherein the hydride containing siloxane compound is tris(trimethylsiloxy) silane or a hydride terminated poly(dimethylsiloxane).
14. The method of claim 12 wherein the allylic halide is allyl bromide.
15. The method of claim 12 wherein the tertiary amino-vinyl compound is 2-(dimethylamino)ethyl methacrylate.
16. The method of claim 12 comprising concentrating the product of step (a) prior to step (b) and then dissolving the concentrated product in a second solvent.
17. The method of claim 12 further comprising:
heating the product of step (b) to a temperature sufficient to promote reaction without causing gelation; and
recovering the cationic organosilicon-containing monomer.
18. The method of claim 17 wherein the step of recovering comprises:
precipitating the cationic organosilicon-containing monomer; and
recovering the cationic organosilicon-containing monomer.
19. The method of claim 18 wherein precipitating is induced by cooling the solution from the temperature sufficient to promote reaction without causing gelation.
20. The method of claim 12 further comprising heating the product of step (b) to a temperature sufficient to promote reaction without causing gelation; cooling the solution to induce precipitation of the cationic organosilicon-containing monomer; and recovering the cationic organosilicon-containing monomer.
21. The method of claim 20 further comprising recrystallizing the recovered cationic organosilicon-containing monomer in a third solvent.