Hydrophilized polydiorganosiloxane vinylic crosslinkers and uses thereof

• US 10,081,697 B2
• Filed: 12/13/2016
• Issued: 09/25/2018
• Est. Priority Date: 12/15/2015
• Status: Active Grant

• Current Assignee: Alcon Incorporated
• Original Assignee: Novartis Ag
• Inventors: Huang, Jinyu, Chang, Frank, Zhang, Steve Yun, Jing, Feng
• Primary Examiner(s): Salamon, Peter A
• Application Number:
  US15/376,700
• Publication Number:
  US 20170166673A1
• Time in Patent Office: 651 Days
• Field of Search: None
• CPC Class Codes: C08F 290/068 Polysiloxanes
• CPC Class Codes: C08G 77/12 containing silicon bound to hydrogen C08G77/045 takes precedence
• CPC Class Codes: C08G 77/16 to hydroxyl groups
• CPC Class Codes: C08G 77/20 containing silicon bound to unsaturated aliphatic groups C08G77/045 takes precedence
• CPC Class Codes: C08G 77/392 containing sulfur
• 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 units each having one methyl substituent and one monovalent C₄-C₄₀ organic radical substituent having two to six hydroxyl groups, wherein the molar ratio of the hydrophilized siloxane units to the dimethylsiloxane units is from about 0.035 to about 0.15, and (2) two terminal (meth)acryloyl groups. The hydrophilized polydiorganosiloxane vinylic crosslinker has a number average molecular weight of from about 3000 Daltons to about 80,000 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.

Claims

1. A polydiorganosiloxane vinylic crosslinker, comprising:

(1) a polydiorganosiloxane polymer chain comprising dimethylsiloxane units and siloxane unit having one methyl substituent and one monovalent C₄-C₄₀ organic radical substituent having two to six hydroxyl groups, wherein the molar ratio of the hydrophilized siloxane units to the dimethylsiloxane units is from about 0.035 to about 0.15;

(2) two terminal (meth)acryloyl groups, wherein the polydiorganosiloxane vinylic crosslinker has a number average molecular weight of from about 3000 Daltons to about 80,000 Daltons.

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

3. The polydiorganosiloxane vinylic crosslinker of claim 2, wherein R₄ is a monovalent radical of formula (2).

4. The polydiorganosiloxane vinylic crosslinker of claim 3, wherein R₄ is a monovalent radical of any one of formula (2a) to (2y)

5. The polydiorganosiloxane vinylic crosslinker of claim 2, wherein R₄ is a monovalent radical of formula (3).

6. The polydiorganosiloxane vinylic crosslinker of claim 5, wherein R₄ is a monovalent radical of any one of formula (3a) to (3y)

7. The polydiorganosiloxane vinylic crosslinker of claim 2, wherein R₄ is a monovalent radical of formula (4).

8. The polydiorganosiloxane vinylic crosslinker of claim 7, wherein R₄ is a monovalent radical of formula (4a) or (4b)

9. The polydiorganosiloxane vinylic crosslinker of claim 2, wherein R₄ is a monovalent radical of formula (5).

10. The polydiorganosiloxane vinylic crosslinker of claim 9, wherein R₄ is a monovalent radical of any one of formula (5a) to (5c)

11. The polydiorganosiloxane vinylic crosslinker of claim 2, wherein R₄ is a monovalent radical of formula (6).

12. The polydiorganosiloxane vinylic crosslinker of claim 11, wherein in formula (6) n1 is 3 and q1 is 1.

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

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

in which R′

is hydrogen or C₁-C₁₀-alkyl.

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

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

in which R′

is hydrogen or C₁-C₁₀-alkyl.

17. The polydiorganosiloxane vinylic crosslinker of claim 7, wherein in formula (1) X₀ is O.

18. The polydiorganosiloxane vinylic crosslinker of claim 7, wherein in formula (1) X₀ is NR′

in which R′

is hydrogen or C₁-C₁₀-alkyl.

19. The polydiorganosiloxane vinylic crosslinker of claim 9, wherein in formula (1) X₀ is O.

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

in which R′

is hydrogen or C₁-C₁₀-alkyl.

21. The polydiorganosiloxane vinylic crosslinker of claim 11, wherein in formula (1) X₀ is O.

22. The polydiorganosiloxane vinylic crosslinker of claim 11, wherein in formula (1) X₀ is NR′

in which R′

is hydrogen or C₁-C₁₀-alkyl.

23. The polydiorganosiloxane vinylic crosslinker of claim 2, wherein the polydiorganosiloxane vinylic crosslinker has a number average molecular weight of from about 4000 Daltons to about 50,000 Dalton.

24. The polydiorganosiloxane vinylic crosslinker of claim 2, wherein the polydiorganosiloxane vinylic crosslinker has a number average molecular weight of from about 5000 Daltons to about 25,000 Daltons.

25. The polydiorganosiloxane vinylic crosslinker of claim 2, wherein the polydiorganosiloxane vinylic crosslinker has a number average molecular weight of from about 6000 Daltons to about 18,000 Daltons.