Granted Patent B2

US 12,351,688 · App. 17/666,601 · Granted Jul 8, 2025

Inventors: Frank Chang (Cumming, GA); Troy Vernon Holland (Suwanee, GA); Houliang Tang (Alpharetta, GA); Adam K. Sniady (Lilburn, GA)

Assignee: Alcon Inc.

C08G77/04G02C7/04

Abstract

Claims (81)

1. A hydrophilized polydiorganosiloxane vinylic crosslinker, comprising:

(1) a polydiorganosiloxane segment comprising dimethylsiloxane units and at least one hydrophilized siloxane unit having one methyl substituent and one organic substituent having one phosphorylcholine moiety; and

(2) ethylenically-unsaturated groups.

2. The hydrophilized polydiorganosiloxane vinylic crosslinker of claim 1 , wherein the polydiorganosiloxane segment comprises from 6 to 500 dimethylsiloxane units.

3. The hydrophilized polydiorganosiloxane vinylic crosslinker of claim 2 , wherein the polydiorganosiloxane segment comprises from 3 to 80 hydrophilized siloxane units.

4. The hydrophilized polydiorganosiloxane vinylic crosslinker of claim 3 , wherein the ethylenically unsaturated groups are (meth)acryloyl groups.

5. The hydrophilized polydiorganosiloxane vinylic crosslinker of claim 3 , wherein the molar ratio of the hydrophilized siloxane units to the dimethylsiloxane units is from about 0.002 to about 0.50.

6. The hydrophilized polydiorganosiloxane vinylic crosslinker of claim 5 , wherein the hydrophilized polydiorganosiloxane vinylic crosslinker has a number average molecular weight of at least 1000 Daltons.

7. The hydrophilized polydiorganosiloxane vinylic crosslinker of claim 3 , wherein the hydrophilized polydiorganosiloxane vinylic crosslinker is defined by formula (1) or (2)

in which:

υ1 is an integer of from 6 to 500;

ω1 is an integer of from 3 to 80;

γ1 is an integer of from 1 to 78;

E 1 is a monovalent radical of

E 2 is a monovalent radical of

R 0 is hydrogen or methyl;

a1 is zero or 1;

X 0 is O or NR N1 ;

R N1 is hydrogen or a C 1 -C 6 alkyl;

L 0 is a C 2 -C 8 alkylene divalent radical or a divalent radical of

L 0 ′ is a C 2 -C 8 alkylene divalent radical;

L 0 ″ is C 3 -C 8 alkylene divalent radical;

X 1 is —O—, —NR N1 —, —NHCOO—, —OCONH—, —CONR N1 —, or —NR N1 CO—;

q1 is an integer of 1 to 20;

R PC is a monovalent radical of

L e is a divalent radical of

R 1 is a linear or branched C 1 -C 10 alkylene divalent radical;

R 2 is a linear or branched C 3 -C 10 alkylene divalent radical;

R 3 is a direct bond or a linear or branched C 1 -C 4 alkylene divalent radical;

n is an integer of 1 to 5;

R′ and R″ independently of each other are C 1 -C 8 alkyl or C 1 -C 8 hydroxyalkyl;

R″' is a C 1 -C 8 alkylene divalent radical;

T 1 is hydrogen, a hydroxyl group or a C 1 -C 4 alkoxy; and

T 2 is a C 1 -C 8 alkyl, a C 1 -C 8 hydroxyalkyl, R 4 —O—R 5 —, or —R PC —T 1 ;

R 4 is a C 1 -C 4 alkyl; and

R 5 is a C 2 -C 8 alkylene divalent radical.

8. The hydrophilized polydiorganosiloxane vinylic crosslinker of claim 7 , wherein in formula (1) or (2) υ1 is an integer of from 10 to 450.

9. The hydrophilized polydiorganosiloxane vinylic crosslinker of claim 8 , wherein in formula (1) or (2) ω1 is an integer of from 5 to 70.

10. The hydrophilized polydiorganosiloxane vinylic crosslinker of claim 8 , wherein the hydrophilized polydiorganosiloxane vinylic crosslinker is represented by formula (1).

11. The hydrophilized polydiorganosiloxane vinylic crosslinker of claim 10 , wherein in formula (1) a1 is zero.

12. The hydrophilized polydiorganosiloxane vinylic crosslinker of claim 11 , wherein in formula (1) X 0 is O.

13. The hydrophilized polydiorganosiloxane vinylic crosslinker of claim 11 , wherein in formula (1) X 0 is NR N1 .

14. The hydrophilized polydiorganosiloxane vinylic crosslinker of claim 8 , wherein the hydrophilized polydiorganosiloxane vinylic crosslinker is represented by formula (2).

15. The hydrophilized polydiorganosiloxane vinylic crosslinker of claim 14 , wherein in formula (2) X 0 is O.

16. The hydrophilized polydiorganosiloxane vinylic crosslinker of claim 15 , wherein in formula (2) X 0 is NR N1 .

17. A silicone hydrogel contact lens, comprising a crosslinked polymeric material that comprises units of a hydrophilized polydiorganosiloxane vinylic crosslinker, wherein the hydrophilized polydiorganosiloxane vinylic crosslinker comprises:

(1) a polydiorganosiloxane segment comprising from 6 to 500 dimethylsiloxane units and 3 to 80 hydrophilized siloxane units each having one methyl substituent and one organic substituent having one phosphorylcholine moiety; and

(2) ethylenically-unsaturated groups.

18. The silicone hydrogel contact lens of claim 17 , wherein the molar ratio of the hydrophilized siloxane units to the dimethylsiloxane units is from about 0.002 to about 0.50.

19. The silicone hydrogel contact lens of claim 17 , wherein, wherein the hydrophilized polydiorganosiloxane vinylic crosslinker has a number average molecular weight of at least 1000 Daltons.

20. The silicone hydrogel contact lens of claim 17 , wherein the hydrophilized polydiorganosiloxane vinylic crosslinker is defined by formula (1) or (2)

in which:

υ1 is an integer of from 6 to 500;

ω1 is an integer of from 3 to 80;

γ1 is an integer of from 1 to 78;

E 1 is a monovalent radical of

E 2 is a monovalent radical of

R 0 is hydrogen or methyl;

a1 is zero or 1;

X 0 is O or NR N1 ;

R N1 is hydrogen or a C 1 -C 6 alkyl;

L 0 is a C 2 -C 8 alkylene divalent radical or a divalent radical of

L 0 ′ is a C 2 -C 8 alkylene divalent radical;

L 0 ″ is C 3 -C 8 alkylene divalent radical;

X 1 is —O—, —NR N1 —, —NHCOO—, —OCONH—, —CONR N1 —, or —NR N1 CO—;

q1 is an integer of 1 to 20;

R PC is a monovalent radical of

L e is a divalent radical of

R 1 is a linear or branched C 1 -C 10 alkylene divalent radical;

R 2 is a linear or branched C 3 -C 10 alkylene divalent radical;

R 3 is a direct bond or a linear or branched C 1 -C 4 alkylene divalent radical;

n is an integer of 1 to 5;

R′ and R″ independently of each other are C 1 -C 8 alkyl or C 1 -C 8 hydroxyalkyl;

R″′ is a C 1 -C 8 alkylene divalent radical;

T 1 is hydrogen, a hydroxyl group or a C 1 -C 4 alkoxy; and

T 2 is a C 1 -C 8 alkyl, a C 1 -C 8 hydroxyalkyl, R 4 —O—R 5 —, or —R PC —T 1 ;

R 4 is a C 1 -C 4 alkyl; and

R 5 is a C 2 -C 8 alkylene divalent radical.

21. The silicone hydrogel contact lens of claim 20 , wherein in formula (1) or (2) υ1 is an integer of from 10 to 450.

22. The silicone hydrogel contact lens of claim 21 , wherein in formula (1) or (2) ω1 is an integer of from 5 to 70.

23. The silicone hydrogel contact lens of claim 17 , wherein the silicone hydrogel contact lens, when being fully hydrated, has an oxygen permeability (Dk) of at least about 40 barrers, a water content of from about 15% to about 70% by weight, and an elastic modulus of from about 0.20 MPa to about 1.8 MPa.

Assignments (2)

Continuity (2)

References Cited (108)