HYDROPHILIC SILICONE MONOMERS, PROCESS FOR THEIR PREPARATION AND THIN FILMS CONTAINING THE SAME

• US 20110181833A1
• Filed: 10/05/2009
• Published: 07/28/2011
• Est. Priority Date: 10/03/2008
• Status: Active Grant

• Current Assignee: Momentive Performance Materials Incorporated
• Original Assignee: Momentive Performance Materials Incorporated
• Inventors: Umapathy, Sentihikumar, Guyer, Kendall Louis, Lewis, Kenrick Martin, Saxena, Anubhav, Wang, Yi-Feng
• Granted Patent: US 8,686,099 B2
• Time in Patent Office: Days
• US Class Current: 351/160.H
• 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 a 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 mono-functional silicone-containing monomer having the general formula:

2. The monomer of claim 1 wherein at least one R comprises a fluorinated hydrocarbon or trialkylsilyloxy group.

3. The monomer 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 monomer of claim 1 wherein a+b is 1 to about 20 for the linear structure and 3 to about 20 for the cyclic structure.

5. The monomer of claim 1 wherein the monomer comprises a cyclic monomer.

6. The monomer of claim 1 wherein the silicone monomer has the following formula:

7. The monomer of claim 6 wherein b is from 0 to 2 and/or p is from 2 to about 15.

8. The monomer 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 monomer of claim 1, wherein n is from 1 to 3 and Rb is a methyl group.

10. A polymer comprising the reaction product of at least one monomer of claim 1.

11. A copolymer comprising the reaction product of at least 2 monomers of claim 1 wherein at least one of said monomers has a different structure than the at least one other monomer.

12. A copolymer comprising the reaction product of at least 1 monomer of claim 1 and at least 1 additional monomer selected from the group consisting of vinylic monomers, acrylamide monomers and acrylic monomers.

13. The copolymer of claim 12 wherein the vinylic monomer is N-vinyl-pyrolidone.

14. The copolymer of claim 12 wherein the acrylic monomer is 2-hydroxy-ethyl-methacrylate (HEMA).

15. The copolymer of claim 12 wherein the acrylamide monomer is N,N-dimethylacrylamide (DMA)

16. The copolymer of claim 12 wherein the additional monomer is a multifunctional crosslinker

17. The copolymer of claim 12 wherein the ratio of said monomer of claim 1 to said at least one additional monomer is from 1:

100 to about 100;

1

23. A silicone-hydrogel film comprising a polymer of claim 10.

24. A contact lens comprising the silicone-hydrogel film of claim 23.

25. The contact lens of claim 24 wherein such contact lenses exhibit a dynamic contact angle with water in the range of 80°

to 30° and

exhibits improved surface wettability compared to contact lenses comprising silicone-hydrogel films made using monomers having linear alkyl linked (meth)acrylated silicone polyether chains.

26. The contact lens of claim 24 wherein such contact lens possesses improved oxygen permeability compared to contact lenses comprising silicone-hydrogel films made using monomers having linear alkyl linked (meth)acrylated silicone polyether chains.

27. A solvent-free, clear, transparent mixture comprising a monomer of claim 1 and one or more hydrophilic co-monomers wherein the difference in solubility parameter between the monomer of claim 1 and the hydrophilic co-monomers is less than about 7.7 (J/mol)^1/2.

28. The mixture of claim 27, wherein the monomer of claim 1 has the formula

29. A silicone-hydrogel film prepared from the mixture of claim 27.

30. A contact lens comprising the silicone-hydrogel film of claim 29.

18. A process for producing a silicone-containing monomer comprising:

a) reacting a silicone-containing compound having the general formula;

R₃Si—

O—

[SiH(R)]_a[OSiR₂]_b—

OSiR₃

wherein

a is 1 to about 50;

b is 0 to about 100; and

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;

with at least one polyether having the general formula;

CH₂═

CHR^b—

(CH₂)_m—

(OC₂H₄)_p—

(OC₃H₆)_q—

(OC₄H₈)_r—

Y

wherein

m is 1 to about 20,

R^b is an alkyl having from 1 to about 4 carbons,

p and q individually are 0 to about 100;

r is 0 to about 50; and

Y is OH, a halogen or an epoxy group,

in the presence of a catalyst to produce a polyether siloxane; and

b) reacting said polyether siloxane with an alkylacryloyl compound having the general formula;

19. The process of claim 18 wherein said reaction of said polyether siloxane with said alkylacryloyl compound is done in the presence of a tertiary base or basic ionic exchange resin (IER) and a low boiling point solvent.

20. The process of claim 19 wherein the solvent is hexane, methyl ethyl ketone or acetone, dichloromethane or chloroform.

21. The process of claim 18 wherein R and X independently are hydrogen or methyl, b is 0, and q and r are 0;

and p is 0 to about 10.

22. The process of claim 18 wherein R and X is independently H or methyl, b is 0, Z is chlorine, p is from 1 to 20, and q and r are 0.