Hydrophilic silicone monomers, process for their preparation and thin films containing the same

• US 9,255,199 B2
• Filed: 02/18/2014
• Issued: 02/09/2016
• Est. Priority Date: 10/03/2008
• Status: Active Grant

• Current Assignee: Momentive Performance Materials Incorporated
• Original Assignee: Momentive Performance Materials Incorporated
• Inventors: Guyer, Kendall Louis, Lewis, Kenrick Martin, Umapathy, Senthilkumar, Saxena, Anubhav, Wang, Yi-Feng
• Primary Examiner(s): Salamon, Peter A
• Application Number:
  US14/182,709
• Publication Number:
  US 20140163135A1
• Time in Patent Office: 721 Days
• Field of Search: None
• US Class Current: 1/1
• CPC Class Codes: C07F 7/0838 Compounds with one or more Si-O-Si sequences compounds with a ring containing only alternating Si and O atoms, i.e. cyclosilanes C07F7/21
• CPC Class Codes: C07F 7/21 Cyclic compounds having at least one ring containing silicon, but no carbon in the ring
• CPC Class Codes: C08L 33/14 of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
• CPC Class Codes: G02C 7/04 Contact lenses for the eyes disinfection or sterilisation of contact lenses A61L12/00

Abstract

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.

Claims

1. A hydrogel composition comprising a silicone-containing monomer having the general formula:

R₃Si—

O[—

Si(R)(Z)O]_a—

[SiR₂O]_b—

SiR₃ 

 

(I)

or

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:

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.

22. A contact lens comprising the hydrogel composition of claim 1.

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:

R₃Si—

O[—

Si(R)(Z)O]_a—

[SiR₂O]_b—

SiR₃ 

 

(I)

or

19. The hydrogel composition of claim 18, wherein the silicone-containing monomer has the formula

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.