Non-reactive, hydrophilic polymers having terminal siloxanes and methods for making and using the same

• US 10,301,465 B2
• Filed: 10/03/2017
• Issued: 05/28/2019
• Est. Priority Date: 05/06/2010
• Status: Active Grant

• Current Assignee: Johnson & Johnson Vision Care Incorporated (Johnson & Johnson)
• Original Assignee: Johnson & Johnson Vision Care Incorporated (Johnson & Johnson)
• Inventors: Scales, Charles, Venkatasubban, Kunisi, Mahadevan, Shivkumar, Fadli, Zohra, Davis, Carrie, Healy, Brent Matthew
• Primary Examiner(s): Pepitone, Michael F
• Application Number:
  US15/723,434
• Publication Number:
  US 20180044518A1
• Time in Patent Office: 602 Days
• CPC Class Codes: C08F 226/10 N-Vinyl-pyrrolidone
• CPC Class Codes: C08F 290/068 Polysiloxanes
• CPC Class Codes: C08F 293/005 using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent
• CPC Class Codes: C08G 77/442 containing vinyl polymer sequences
• CPC Class Codes: C08L 39/06 Homopolymers or copolymers of N-vinyl-pyrrolidones
• CPC Class Codes: C08L 39/08 Homopolymers or copolymers of vinyl-pyridine
• CPC Class Codes: C08L 51/08 grafted on to macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon-to-carbon bonds
• CPC Class Codes: C08L 51/085 on to polysiloxanes
• 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
• CPC Class Codes: G02C 7/049 Contact lenses having special fitting or structural features achieved by special materials or material structures

Abstract

The present invention relates to compositions comprising at least one stable, near-monodisperse, non-reactive hydrophilic polymer comprising in said polymer'"'"'s backbone, a hydrophilic segment having a degree of polymerization of about 10 to about 1000, and a linear silicone segment at at least one terminal end of said non-reactive hydrophilic polymer, wherein said silicone segment comprises between about 6 and about 200 siloxy units, and said non-reactive hydrophilic polymer is associated, via the linear silicone block with a silicone hydrogel. The non-reactive hydrophilic polymers may be incorporated into the formulation from which the silicone hydrogel is made or may be contacted with the silicone hydrogel post formation.

Claims

1. An ophthalmic solution comprising at least one stable, non-reactive hydrophilic polymer comprising in said polymer'"'"'s backbone, a hydrophilic segment having a degree of polymerization of about 300 to about 10,000, and a linear silicone segment at at least one terminal end of said non-reactive hydrophilic polymer, wherein said silicone segment comprises between about 6 and about 200 siloxy units, wherein said non-reactive hydrophilic polymer is present in a contact angle reducing amount and said ophthalmic solution is transparent, wherein said polymer has a polydispersity of less than about 1.5.

2. The ophthalmic solution of claim 1 wherein said at least one stable, non-reactive hydrophilic polymer comprises 6 to 60 siloxy repeat units.

3. The ophthalmic solution of claim 1 wherein said at least one stable, non-reactive hydrophilic polymer further comprises 6 to 20 siloxy repeat units.

4. The ophthalmic solution of claim 1 wherein said at least one stable, non-reactive hydrophilic polymer is present in an amount between about 0.005 and about 2%.

5. The ophthalmic solution of claim 1 wherein said at least one stable, non-reactive hydrophilic polymer is present in an amount between about 0.01 and about 0.5 weight %.

6. The ophthalmic solution of claim 1 wherein said hydrophilic segment of said non-reactive hydrophilic polymer has a degree of polymerization between about 500 and about 10,000.

7. The ophthalmic solution of claim 1 wherein said hydrophilic segment of said non-reactive hydrophilic polymer has a degree of polymerization between about 500 and about 5000.

8. The ophthalmic solution of claim 1 wherein hydrophilic segment and linear silicone segment are present in said non-reactive hydrophilic polymer in a ratio, based upon the degree of polymerization, between 13:

1 and 500;

1.

9. The ophthalmic solution of claim 8 wherein the ratio of hydrophilic segment to linear silicone segment, based upon degree of polymerization is between 70:

1 and 200;

1.

10. An ophthalmic solution comprising at least one stable, non-reactive hydrophilic polymer comprising in said polymer'"'"'s backbone, a hydrophilic segment having a degree of polymerization of about 300 to about 10,000, and a linear silicone segment at at least one terminal end of said non-reactive hydrophilic polymer, wherein said silicone segment comprises between about 6 and about 200 siloxy units, wherein said non-reactive hydrophilic polymer is present in a contact angle reducing amount and said ophthalmic solution is transparent, and wherein said polymer is a polymer of Formula I:

11. The ophthalmic solution of claim 10 wherein

R₁ is selected from the group consisting of substituted and unsubstituted C_1-10 alkyl;

R₂-R₅ are independently selected from C₁-C₄ alkyl,

R₆ is selected from the group consisting aromatic groups of the following formulae;

12. The ophthalmic solution of claim 10 wherein R₁ is selected from the group consisting of substituted and unsubstituted C_1-4 alkyl and R₂-R₅ are methyl.

13. The ophthalmic solution of claim 10 wherein n is 6-12.

14. The ophthalmic solution of claim 10 wherein

R₁ is selected from the group consisting of substituted and unsubstituted C_1-10 alkyl;

R₂-R₅ are independently selected from C₁-C₄ alkyl,

R₆ is selected from the group consisting of alkylenes;

15. The ophthalmic solution of claim 10 wherein Z is selected from optionally substituted alkoxy, optionally substituted alkylthio, optionally substituted aryl, and optionally substituted benzyl.