Biomedical devices
A biomedical device is disclosed which is a polymerization product of a mixture comprising (a) one or more difunctional isocyanates; (b) one or more polyalcohols; (c) one or more hydroxy-terminated polysiloxane prepolymers; and (d) one or more polyoxazoline polyols having a weight average molecular weight of equal to or greater than about 1000 Daltons.
1. A biomedical device which is a polymerization product of a mixture comprising:
(a) about 20 to about 60 weight percent, based on the total weight of the mixture, of one or more difunctional isocyanates;
(b) about 10 to about 70 weight percent, based on the total weight of the mixture, of one or more polyalcohols;
(c) about 10 to about 70 weight percent, based on the total weight of the mixture, of one or more hydroxy-terminated polysiloxane prepolymers; and
(d) about 5 to about 65 weight percent, based on the total weight of the mixture, of one or more polyoxazoline polyols having a weight average molecular weight of equal to or greater than about 1000 Daltons.
2. The biomedical device of claim 1 , wherein the one or more difunctional isocyanates comprise an aliphatic isocyanate, a cycloaliphatic isocyanate and an aromatic isocyanate.
3. The biomedical device of claim 1 , wherein the one or more difunctional isocyanates are of the formula OCN—R 1 —NCO, wherein R 1 is a linear or branched C 3 -C 18 -alkylene group, a C 6 -C 10 -arylene group, a C 7 -C 18 -aralkylene group, a C 6 -C 10 -arylene-C 1 -C 2 -alkylene-C 6 -C 10 -arylene group, a C 3 -C 8 -cycloalkylene group, a C 3 -C 8 -cycloalkylene-C 1 -C 6 -alkylene group, a C 3 -C 8 -cycloalkylene-C 1 -C 6 -alkylene-C 3 -C 8 -cycloalkylene group or a C 1 -C 6 -alkylene-C 3 -C 8 -cyclo-alkylene-C 1 -C 6 -alkylene group.
4. The biomedical device of claim 1 , wherein the one or more polyalcohols have from about 2 to about 50 carbon atoms and at least 2 hydroxy groups.
5. The biomedical device of claim 1 , wherein the one or more polyalcohols are selected from the group consisting of a diol, a triol, a tertiary amine polyalcohol, an alkoxylated polyalcohol, a polyether polyalcohol, and mixtures thereof.
6. The biomedical device of claim 1 , wherein the one or more hydroxy-terminated polysiloxane prepolymers are of the formula:
wherein each R, R 1 , R 2 , R 3 and R 4 group independently represents H or a hydrocarbyl group; p is an integer from 0 to 40; q is an integer from 0 to 40; z is an integer from 2 to 50; u is an integer from 1 to 100; y is an integer from 0 to 40; w is an integer from 0 to 40; v is an integer from 2 to 50; and each Q group independently represents a hydroxyl-containing reactive functional end group.
7. The biomedical device of claim 1 , wherein the one or more polyoxazoline polyols comprise one or more di-functional, tri-functional and tetra-functional polyoxazoline polyols.
8. The biomedical device of claim 7 , wherein the one or more di-functional polyoxazoline polyols are one or more polyoxazoline polyols having two oxazoline-containing hydroxyl groups per molecule.
9. The biomedical device of claim 7 , wherein the one or more tri-functional polyoxazoline polyols are one or more polyoxazoline polyols having three oxazoline-containing hydroxyl groups per molecule.
10. The biomedical device of claim 7 , wherein the one or more polyoxazoline polyols are one or more tetra-functional polyoxazoline polyols having four oxazoline-containing hydroxyl groups per molecule.
11. The biomedical device of claim 1 , wherein the one or more polyoxazoline polyols are of the formula:
wherein each R is a hydroxyl group; each R′ is independently an alkyl group, a haloalkyl group, an alkene group, an alkyne group, a cycloalkyl group, a halocycloalkyl group, an aryl group, a haloaryl group, an aralkyl group and a haloaralkyl group; Z is a divalent linkage and each of x and y are independently at least 1.
12. The biomedical device of claim 1 , wherein the mixture further comprises a catalytic amount of one or more catalysts.
13. The biomedical device of claim 1 , wherein the mixture comprises:
(a) about 30 to about 45 weight percent, based on the total weight of the mixture, of the one or more difunctional isocyanates;
(b) about 12 to about 20 weight percent, based on the total weight of the mixture, of the one or more polyalcohols;
(c) about 10 to about 50 weight percent, based on the total weight of the mixture, of the one or more hydroxy-terminated polysiloxane prepolymers; and
(d) about 10 to about 45 weight percent, based on the total weight of the mixture, of the one or more polyoxazoline polyols having a weight average molecular weight of equal to or greater than about 1000 Daltons.
14. The biomedical device of claim 1 , which is one of a contact lens or an intraocular lens.
15. The biomedical device of claim 1 , wherein the polymerization product is a thermosetting polymerization product.
16. A method of making a biomedical device, the method comprising:
(a) providing a mixture comprising:
(i) about 20 to about 60 weight percent, based on the total weight of the mixture, of one or more difunctional isocyanates;
(ii) about 10 to about 70 weight percent, based on the total weight of the mixture, of one or more polyalcohols;
(iii) about 10 to about 70 weight percent, based on the total weight of the mixture, of one or more hydroxy-terminated polysiloxane prepolymers; and
(iv) about 5 to about 65 weight percent, based on the total weight of the mixture, of one or more polyoxazoline polyols having a weight average molecular weight of equal to or greater than about 1000 Daltons;
(b) subjecting the mixture to polymerization conditions to provide a polymerized device; and
(c) hydrating the polymerized device.
17. The method of claim 16 , wherein the one or more difunctional isocyanates comprise an aliphatic isocyanate, a cycloaliphatic isocyanate and an aromatic isocyanate, the one or more polyalcohols have from about 2 to about 50 carbon atoms and at least 2 hydroxy groups, and the one or more polyoxazoline polyols are one or more di-functional, tri-functional or tetra-functional polyoxazoline polyols.
18. The method of claim 16 , wherein the one or more hydroxy-terminated polysiloxane prepolymers are of the general formula:
wherein each R, R 1 , R 2 , R 3 and R 4 group independently represents H or a hydrocarbyl group; p is an integer from 0 to 40; q is an integer from 0 to 40; z is an integer from 2 to 50; u is an integer from 1 to 100; y is an integer from 0 to 40; w is an integer from 0 to 40; v is an integer from 2 to 50; and each Q group independently represents a hydroxyl-containing reactive functional end group.
19. The method of claim 16 , wherein the one or more polyoxazoline polyols comprise one or more di-functional, tri-functional and tetra-functional polyoxazoline polyols.
20. A biomedical device which is a polymerization product of a mixture comprising:
(a) one or more difunctional isocyanates;
(b) one or more polyalcohols;
(c) one or more hydroxy-terminated polysiloxane prepolymers; and
(d) one or more polyoxazoline polyols having a weight average molecular weight of equal to or greater than about 1000 Daltons, wherein the one or more polyoxazoline polyols are one or more tetra-functional polyoxazoline polyols having four oxazoline-containing hydroxyl groups per molecule.
21. The biomedical device of claim 20 , wherein the mixture comprises:
(a) about 20 to about 60 weight percent, based on the total weight of the mixture, of the one or more difunctional isocyanates;
(b) about 10 to about 70 weight percent, based on the total weight of the mixture, of the one or more polyalcohols;
(c) about 3 to about 60 weight percent, based on the total weight of the mixture, of the one or more hydroxy-terminated polysiloxane prepolymers; and
(d) about 5 to about 65 weight percent, based on the total weight of the mixture, of the one or more polyoxazoline polyols having a weight average molecular weight of equal to or greater than about 1000 Daltons.