Contact Lenses Made With HEMA-Compatible Polysiloxane Macromers

• US 20140066540A1
• Filed: 08/27/2013
• Published: 03/06/2014
• Est. Priority Date: 08/28/2012
• Status: Active Grant

• Current Assignee: Coopervision International Limited (The Cooper Cos., Inc.)
• Original Assignee: Coopervision International Holding Company LP (The Cooper Cos., Inc.)
• Inventors: Chen, Charlie, Xu, Yuan, Liu, Yuwen, Zheng, Ying, Richardson, Paul, Ueyama, Hiroyuki, Dande, Prasad
• Granted Patent: US 9,322,959 B2
• Time in Patent Office: Days
• US Class Current: 523/107
• CPC Class Codes: C08G 77/20 containing silicon bound to unsaturated aliphatic groups C08G77/045 takes precedence
• CPC Class Codes: C08G 77/442 containing vinyl polymer sequences
• CPC Class Codes: C08G 77/46 containing polyether sequences
• CPC Class Codes: C08L 101/14 the macromolecular compounds being water soluble or water swellable, e.g. aqueous gels
• CPC Class Codes: C08L 33/10 Homopolymers or copolymers of methacrylic acid esters
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: C08L 83/06 containing silicon bound to oxygen-containing groups C08L83/12 takes precedence
• CPC Class Codes: C08L 83/12 containing polyether sequences
• CPC Class Codes: G02B 1/04 made of organic materials, e.g. plastics G02B1/08 takes precedence
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

Optically clear silicone hydrogel contact lenses are described that comprise a polymeric lens body that is the reaction product of a polymerizable composition comprising at least 25 wt. % of at least one hydroxyalkyl methacrylate; and at least 20 wt. % of at least one HEMA-compatible bifunctional polysiloxane comprising at least 6 siloxane groups and having an HLB value of at least 5 and/or a hydroxyl group content of at least 1 wt. %.

Claims

1. An optically clear silicone hydrogel contact lens comprising:

a polymeric lens body that is the reaction product of a polymerizable composition comprising;

a) at least 25 wt. % of at least one hydroxyalkyl methacrylate; and

b) at least 20 wt. % of at least one HEMA-compatible bifunctional polysiloxane comprising at least 6 siloxane groups,

wherein the HEMA-compatible bifunctional polysiloxane has an HLB value of at least 5, or has a hydroxyl group content of at least 1 wt. % based on the average molecular weight of the polysiloxane, or has both an HLB value of at least 5 and has a hydroxyl group content of at least 1 wt. %,

wherein the wt. % of the hydroxyalkyl methacrylate and the HEMA-compatible bifunctional polysiloxane is based on the total weight of polymerizable monomers in the composition.

2. The contact lens of claim 1, wherein the HEMA-compatible bifunctional polysiloxane has the structure of Formula 4:

3. The contact lens of claim 1, wherein the HEMA-compatible bifunctional polysiloxane has an HLB value of at least 7.

4. The contact lens of claim 1, wherein the HEMA-compatible bifunctional polysiloxane has an HLB value of less than 5 and a hydroxyl group content of at least 1 wt. %.

5. The contact lens of claim 4, wherein the HLB value is from 2 to 4 and hydroxyl group content is from 4 wt. % to 8 wt. %.

6. The contact lens of claim 1, wherein the polymerizable composition further comprises:

c) 1 to 65 wt. % diluent, wherein the wt. % of the diluent is based on the total weight of the polymerizable composition, and wherein the diluent comprises water, a low molecular weight polyethylene glycol (PEG), or a combination thereof.

7. The contact lens of claim 6, wherein the HEMA-compatible bifunctional polysiloxane requires water addition for optical clarity.

8. The contact lens of claim 1, wherein the polymerizable composition comprises from 0.1 wt. % up to about 5 wt. % methacrylic acid or acrylic acid.

9. The contact lens of claim 1, wherein the polymerizable composition comprises at least 35 wt. % of the hydroxyalkyl methacrylate.

10. The contact lens of claim 1, wherein the hydroxyalkyl methacrylate is 2-hydroxyethyl methacrylate (HEMA).

11. The contact lens of claim 1, having a Dk of at least 35.

12. The contact lens of claim 1, wherein the polymerizable composition comprises a monomer selected from methacrylic acid, acrylic acid, glycerol methacrylate, and combinations thereof.

13. The contact lens of claim 12, wherein the polymerizable composition optionally comprises a crosslinking agent, a polymerizable dye, or both a crosslinking agent and a polymerizable dye, and no other polymerizable components.

14. A method of manufacturing the optically clear contact lens of claim 1, comprising:

a) polymerizing the polymerizable composition to form the polymeric lens body; and

b) hydrating the polymeric lens body,

wherein the polymerizable composition is either diluent-free or comprises about 1 to 65 wt. % of a diluent consisting essentially of water or a low molecular weight PEG, or a combination thereof, wherein the wt. % of the diluent is based on the total weight of the polymerizable composition.

15. The method of claim 14, wherein the polymerizable composition is cured in a mold to form the polymeric lens body, and wherein the polymeric lens body is dry-delensed from the mold prior to hydrating the polymeric lens body.

16. A HEMA-compatible polysiloxane having the structure of Formula 4:

17. The HEMA-compatible polysiloxane of claim 16, wherein m is an integer of 6 to 60, n is an integer of 1 to 10, p is an integer of 10 to 30, and q is 0.

18. The HEMA-compatible polysiloxane of claim 16, wherein m is 0, n is an integer of 10 to 60, p is an integer of 0 to 6, and q is 0.

19. The HEMA-compatible polysiloxane of claim 18, wherein n is an integer of 20 to 40 and p is 0.

20. The HEMA-compatible polysiloxane of claim 16, wherein m is an integer of 6 to 60, n is an integer of 1 to 10, p is an integer of 1 to 40, and q is an integer of 1 to 10.

21. The HEMA-compatible polysiloxane of claim 16, wherein m is an integer of 6 to 50, n is an integer of 1 to 6, p is an integer of 8 to 20, and q is an integer of 2 to 8.

22. The HEMA-compatible polysiloxane of claim 16, having a purity of at least 90%.

23. The HEMA-compatible polysiloxane of claim 16, wherein k is 0.

24. A method of purifying a polysiloxane from a reaction product comprising the polysiloxane and an unreacted polyethylene glycol-containing reagent, said method comprising:

a) combining the reaction product with an organic solvent and water or an aqueous solution to make a mixture;

b) equilibrating the mixture into an organic layer and an aqueous layer; and

c) discarding the aqueous layer from the organic layer.

25. The method of claim 24, further comprising:

d) combining the organic layer from step (c) with water or aqueous solution and repeating the equilibrating and discarding steps one or more times.

26. The method of claim 24, wherein the equilibrating step comprises centrifuging the mixture.