Contact lenses made with HEMA-compatible polysiloxane macromers

• US 9,322,959 B2
• Filed: 08/27/2013
• Issued: 04/26/2016
• 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: Chen, Charlie, Xu, Yuan, Liu, Yuwen, Zheng, Ying, Richardson, Paul, Dande, Prasad, Ueyama, Hiroyuki
• Primary Examiner(s): Salamon, Peter A
• Application Number:
  US14/010,609
• Publication Number:
  US 20140066540A1
• Time in Patent Office: 973 Days
• Field of Search: None
• 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. 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 7,

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 a hydroxyl group content of at least 1 wt. % based on the average molecular weight of the polysiloxane.

4. 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.

5. The contact lens of claim 4, wherein the HEMA-compatible bifunctional polysiloxane requires water addition for optical clarity.

6. 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.

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

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

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

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

11. The contact lens of claim 10, 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.

12. 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.

13. The method of claim 12, 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.