Hydrophilic silicone monomers, process for their preparation and thin films containing the same
View Patent ↗There is provided new mono-(meth)acrylate functionalized hydrophilic silicone monomers containing a polyether with branched linking group, useful in making water absorbing silicone-hydrogel films for contact lens applications. This invention also provides homo-polymers and copolymers made from the mono-(meth)acrylate functionalized hydrophilic silicone monomers described herein. Also provided is a process for producing the monomers and polymers described herein and contact lenses produced from the same.
1. A hydrogel composition comprising a silicone-containing monomer having the general formula:
R 3 Si—O[—Si(R)(Z)O] a —[SiR 2 O] b —SiR 3 (I)
or
wherein
a is 1 to about 50;
b is 0 to about 100;
each R is independently selected from the group consisting of monovalent aliphatic, cycloaliphatic or aromatic hydrocarbon groups of 1 to about 10 carbons and halogenated hydrocarbon groups of 1 to about 10 carbons;
Z is a polyether having the general formula:
—H 2 C—CH(R b )—(CH 2 ) n —O—(C 2 H 4 O) p —(C 3 H 6 O) q —(C 4 H 8 O) r —X
wherein
n is 1 to about 20;
p and q individually are 0 to about 100;
R b is an alkyl group having from 1 to about 4 carbon atoms;
r is 0 to about 50 and the sum of p+q+r is greater than 0; and
X is a polyether-capping group having the general formula:
wherein R 3 and R 4 independently are either hydrogen or a substituted or unsubstituted saturated monovalent hydrocarbon group of 1 to about 20 carbons.
2. The hydrogel composition of claim 1 , wherein at least one R comprises a fluorinated hydrocarbon or trialkylsilyloxy group.
3. The hydrogel composition of claim 1 , wherein each R independently comprises a saturated monovalent hydrocarbon group of from 1 to 6 carbon atoms or a phenyl group.
4. The hydrogel composition of claim 1 , wherein a+b is 1 to about 20 for formula (I) and 3 to about 20 for formula (II).
5. The hydrogel composition of claim 1 , wherein the silicone-containing monomer comprises a cyclic monomer.
6. The hydrogel composition of claim 1 , wherein the silicone-containing monomer has the following formula:
wherein b is 0 to about 100, and p is 1 to about 50.
7. The hydrogel composition of claim 6 , wherein b is from 0 to 2 and p is from 2 to about 15.
8. The hydrogel composition of claim 1 , wherein b is equal to 0 and the total number of carbon atoms present in Z is at least 6.
9. The hydrogel composition of claim 1 , wherein n is from 1 to 3 and R b is a methyl group.
10. The hydrogel composition of claim 1 , wherein the composition comprises monomers of the silicone-containing monomer having the same structure.
11. The hydrogel composition of claim 1 comprising the silicone-containing monomer and a second silicone-containing monomer of the Formula (I), and the silicone-containing monomer has a different structure than the second silicone-containing monomer.
12. The hydrogel composition of claim 1 comprising the silicone-containing monomer and at least one hydrophilic monomer.
13. The hydrogel composition of claim 12 , wherein the at least one hydrophilic monomer is chosen from a vinylic monomer, an acrylamide monomer, an acrylic monomer, or a combination of two or more thereof.
14. The hydrogel composition of claim 12 , wherein the at least one hydrophilic monomer is chosen from N-vinyl-pyrolidone, 2-hydroxy-ethyl-methacrylate, N,N-dimethylacrylamide, methacrylic acid, or a combination of two or more thereof.
15. The hydrogel composition of claim 12 , wherein the at least one hydrophilic monomer is a multifunctional crosslinker.
16. The hydrogel composition of claim 12 wherein the ratio of the silicone-containing monomer to the at least one hydrophilic monomer is from 1:100 to about 100:1.
17. A hydrogel film prepared from the hydrogel forming composition of claim 12 .
18. A hydrogel composition comprising (a) a silicone-containing monomer, and (b) at least one hydrophilic co-monomer, wherein the difference in solubility parameter between the silicone-containing monomer and the at least one hydrophilic co-monomer is less than about 7.7 (J/mol) 1/2 , and the silicone-containing monomer is of the formula:
R 3 Si—O[—Si(R)(Z)O] a —[SiR 2 O] b —SiR 3 (I)
or
wherein
a is 1 to about 50;
b is 0 to about 100;
each R is independently selected from the group consisting of monovalent aliphatic, cycloaliphatic or aromatic hydrocarbon groups of 1 to about 10 carbons and halogenated hydrocarbon groups of 1 to about 10 carbons;
Z is a polyether having the general formula:
—H 2 C—CH(R b )—(CH 2 ) n —O—(C 2 H 4 O) p —(C 3 H 6 O) q —(C 4 H 8 O) r —X
wherein
n is 1 to about 20;
p and q individually are 0 to about 100;
R b is an alkyl group having from 1 to about 4 carbon atoms;
r is 0 to about 50 and the sum of p+q+r is greater than 0; and
X is a polyether-capping group having the general formula:
wherein R 3 and R 4 independently are either hydrogen or a substituted or unsubstituted saturated monovalent hydrocarbon group of 1 to about 20 carbons.
19. The hydrogel composition of claim 18 , wherein the silicone-containing monomer has the formula
wherein b is 0 to about 100, and p is 1 to about 50; and the at least one hydrophilic co-monomer is chosen from N-vinyl-pyrolidone, 2-hydroxy-ethyl-methacrylate, N,N-dimethylacrylamide, methacrylic acid, or a combination of two or more thereof.
20. The hydrogel composition of claim 18 , wherein the composition is free of a solvent.
21. A hydrogel film prepared from the composition of claim 18 .
22. A contact lens comprising the hydrogel composition of claim 1 .