Contact Lenses Made With HEMA-Compatible Polysiloxane Macromers

• US 20160185914A1
• Filed: 03/10/2016
• Published: 06/30/2016
• 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: Ueyama, Hiroyuki, Chen, Charlie, Xu, Yuan, Liu, Yuwen, Zheng, Ying, Richardson, Paul, Dande, Prasad
• Granted Patent: US 9,453,110 B2
• Time in Patent Office: Days
• US Class Current: 1/1
• 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

1-15. -15. (canceled)

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.