Polymerizable polysiloxanes with hydrophilic substituents

• US 10,227,435 B2
• Filed: 12/13/2016
• Issued: 03/12/2019
• Est. Priority Date: 12/15/2015
• Status: Active Grant

• Current Assignee: Alcon Incorporated
• Original Assignee: Novartis Ag
• Inventors: Chang, Frank, DeSousa, Ryan, Huang, Jinyu
• Primary Examiner(s): Salamon, Peter A
• Application Number:
  US15/376,702
• Publication Number:
  US 20170166674A1
• Time in Patent Office: 819 Days
• Field of Search: None
• CPC Class Codes: C08F 290/068 Polysiloxanes
• CPC Class Codes: C08G 2210/00 Compositions for preparing hydrogels
• CPC Class Codes: C08G 77/12 containing silicon bound to hydrogen C08G77/045 takes precedence
• CPC Class Codes: C08G 77/14 containing silicon bound to oxygen-containing groups C08G77/045 takes precedence
• CPC Class Codes: C08G 77/20 containing silicon bound to unsaturated aliphatic groups C08G77/045 takes precedence
• CPC Class Codes: C08G 77/38 Polysiloxanes modified by chemical after-treatment C08G77/045 takes precedence
• CPC Class Codes: C08L 101/14 the macromolecular compounds being water soluble or water swellable, e.g. aqueous gels
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: G02B 1/043 Contact lenses

Abstract

The invention provides a hydrophilized polydiorganosiloxane vinylic crosslinker which comprises (1) a polydiorganosiloxane polymer chain comprising dimethylsiloxane units and hydrophilized siloxane unit having one methyl substituent and one monovalent C₁₀-C₅₀ organic substituent having two or three carboxy groups, wherein the molar ratio of the hydrophilized siloxane units to the dimethylsiloxane units is from about 0.035 to about 0.25, and (2) two terminal (meth)acryloyl groups. The hydrophilized polydiorganosiloxane vinylic crosslinker has a number average molecular weight of greater than 3000 Daltons. The present invention is also related to a silicone hydrogel contact lens, which comprises repeating units derived from a hydrophilized polydiorganosiloxane vinylic crosslinker of the invention. In addition, the invention provides a method for making silicone hydrogel contact lenses using a lens-forming formulation comprising hydrophilized polydiorganosiloxane vinylic crosslinker of the invention.

Claims

1. A hydrophilized polydiorganosiloxane vinylic crosslinker, comprising:

(1) a polydiorganosiloxane polymer chain comprising dimethylsiloxane units and hydrophilized siloxane unit having one methyl substituent and one monovalent C₁₀-C₅₀ organic substituent having at least two carboxy groups, wherein the molar ratio of the hydrophilized siloxane units to the dimethylsiloxane units is from about 0.035 to about 0.25;

(2) two terminal (meth)acryloyl groups, wherein the hydrophilized polydiorganosiloxane vinylic crosslinker has a number average molecular weight of at least about 3000 Daltons.

2. The hydrophilized polydiorganosiloxane vinylic crosslinker of claim 1, wherein the hydrophilized polydiorganosiloxane vinylic crosslinker is a polymer of formula (1)

3. The hydrophilized polydiorganosiloxane vinylic crosslinker of claim 2, wherein R₄ is of formula (2) in which n1 is 3, q1 is 1, R₇ is hydrogen, R₈ is a radical of

4. The hydrophilized polydiorganosiloxane vinylic crosslinker of claim 2, wherein R₄ is of formula (2) in which n1 is 3, q1 is 1, R₇ is a radical of

5. The hydrophilized polydiorganosiloxane vinylic crosslinker of claim 2, wherein R₄ is of formula (2) in which n1 is 3, q1 is 1, R₇ and R₈ are a radical of

6. The hydrophilized polydiorganosiloxane vinylic crosslinker of claim 3, wherein in formula (1) ω

1/υ

1 is from about 0.040 to about 0.18.

7. The hydrophilized polydiorganosiloxane vinylic crosslinker of claim 3, wherein the hydrophilized polydiorganosiloxane vinylic crosslinker has a number average molecular weight of from about 4000 Daltons to about 80,000 Daltons.

8. The hydrophilized polydiorganosiloxane vinylic crosslinker of claim 3, wherein in formula (1) X₀ is O.

9. The hydrophilized polydiorganosiloxane vinylic crosslinker of claim 3, wherein in formula (1) X₀ is NR′

in which R′

is hydrogen or C₁-C₁₀-alkyl.

10. The hydrophilized polydiorganosiloxane vinylic crosslinker of claim 4, wherein in formula (1) ω

1/υ

1 is from about 0.040 to about 0.18.

11. The hydrophilized polydiorganosiloxane vinylic crosslinker of claim 4, wherein the hydrophilized polydiorganosiloxane vinylic crosslinker has a number average molecular weight of from about 4000 Daltons to about 80,000 Daltons.

12. The hydrophilized polydiorganosiloxane vinylic crosslinker of claim 4, wherein in formula (1) X₀ is O.

13. The hydrophilized polydiorganosiloxane vinylic crosslinker of claim 3, wherein in formula (1) X₀ is NR′

in which R′

is hydrogen or C₁-C₁₀-alkyl.

14. The hydrophilized polydiorganosiloxane vinylic crosslinker of claim 5, wherein in formula (1) ω

1/υ

1 is from about 0.040 to about 0.18.

15. The hydrophilized polydiorganosiloxane vinylic crosslinker of claim 5, wherein the hydrophilized polydiorganosiloxane vinylic crosslinker has a number average molecular weight of from about 4000 Daltons to about 80,000 Daltons.

16. The hydrophilized polydiorganosiloxane vinylic crosslinker of claim 5, wherein in formula (1) X₀ is O.

17. The hydrophilized polydiorganosiloxane vinylic crosslinker of claim 5, wherein in formula (1) X₀ is NR′

in which R′

is hydrogen or C₁-C₁₀-alkyl.