Zwitterionic double network hydrogels

Patent metadata

Field	Value
Publication number	US-12291652-B2
Application number	US-201917268310-A
Country	US
Kind code	B2
Filing date	Aug 14, 2019
Priority date	Aug 14, 2018
Publication date	May 6, 2025
Grant date	May 6, 2025

Abstract

Zwitterionic double network hydrogels, methods for making zwitterionic double network hydrogels, methods for using zwitterionic double network hydrogels, and articles made from and coated with zwitterionic double network hydrogels.

First claim

The embodiments of the invention in which an exclusive property or privilege is claimed are defined as follows:

1. A double network hydrogel, comprising:
(a) a first polymeric network comprising a first crosslinked zwitterionic polymer having from about 50 to about 100 mole percent zwitterionic moieties; and
(b) a second polymeric network comprising a second crosslinked zwitterionic polymer having from about 50 to about 100 mole percent zwitterionic moieties,
wherein the double network hydrogel has a compressive fracture stress of greater than about 0.9 MPa.

2. A double network hydrogel, comprising:
(a) a first polymeric network comprising a first chemically crosslinked zwitterionic polymer having from about 50 to about 100 mole percent zwitterionic moieties; and
(b) a second polymeric network comprising a second chemically crosslinked zwitterionic polymer having from about 50 to about 100 mole percent zwitterionic moieties.

3. The double network hydrogel of claim 1 , wherein the first crosslinked zwitterionic polymer is a poly(carboxybetaine), poly(sulfobetaine), poly(sulfabetaine), poly(phosphobetaine), poly(phosphorylcholine), poly(choline phosphate), poly(trimethylamine-N-oxide), or a latent derivative thereof.

4. The double network hydrogel of claim 1 , wherein the second crosslinked zwitterionic polymer is a poly(carboxybetaine), poly(sulfobetaine), poly(sulfabetaine), poly(phosphobetaine), poly(phosphorylcholine), poly(choline phosphate), poly(trimethylamine-N-oxide), or a latent derivative thereof.

5. The double network hydrogel of claim 1 , wherein the first crosslinked zwitterionic polymer is a poly(carboxybetaine) and the second crosslinked zwitterionic polymer is a poly(sulfobetaine).

6. The double network hydrogel of claim 1 , wherein the first crosslinked zwitterionic polymer is a poly(sulfobetaine) and the second crosslinked zwitterionic polymer is a poly(sulfobetaine).

7. The double network hydrogel of claim 1 , wherein the first crosslinked zwitterionic polymer is a poly(trimethylamine-N-oxide) and the second crosslinked zwitterionic polymer is a poly(sulfobetaine).

8. The double network hydrogel of claim 1 , wherein the first crosslinked zwitterionic polymer is a poly(phosphorylcholine) and the second crosslinked zwitterionic polymer is a poly(sulfobetaine).

9. The double network hydrogel of claim 1 , wherein the second crosslinked zwitterionic polymer is a poly(sulfobetaine).

10. The double network hydrogel of claim 1 having a tensile fracture stress greater than about 0.3 MPa, a tensile fracture strain greater than about 200%, or a Young's modulus greater than about 0.01 MPa.

11. The double network hydrogel of claim 1 , wherein the first polymeric network is chemically crosslinked or physically crosslinked, and the second polymeric network is chemically crosslinked or physically crosslinked.

12. The double network of claim 11 , wherein physically crosslinked is crosslinking between polymers through ionic interaction, hydrogen bonding, or dipole-dipole interaction.

13. The double network hydrogel of claim 1 having a fibrinogen binding level of less than about 20% relative to that of tissue culture polystyrene tested via a fibrinogen binding assay in which a polymer surface is incubated at 37° C. for 90 minutes with a 1.0 mg/mL fibrinogen solution in 0.15 M phosphate buffered saline at pH 7.4.

14. The double network hydrogel of claim 1 obtained by a two-step process, wherein the first polymeric network is formed, and then the first polymeric network is soaked to equilibrium in a solution comprising precursors of the second polymeric network, followed by the polymerization of the precursors to provide the double network.

15. The double network hydrogel of claim 1 obtained by a single-pot process, wherein the second polymeric network is formed by (a) monomer polymerization, (b) comonomer copolymerization, or (c) physical crosslinking of a zwitterionic polymer or zwitterionic copolymer in the presence of the first polymeric network.

16. An article of manufacture comprising, in whole or in part, a double network hydrogel of claim 1 .

17. A microgel, comprising a double network hydrogel of claim 1 .

18. A surface coating for a substrate, comprising a double network hydrogel of claim 1 .

19. The double network hydrogel of claim 2 , wherein the first crosslinked zwitterionic polymer is a poly(carboxybetaine), poly(sulfobetaine), poly(sulfabetaine), poly(phosphobetaine), poly(phosphorylcholine), poly(choline phosphate), poly(trimethylamine-N-oxide), or a latent derivative thereof.

20. The double network hydrogel of claim 2 , wherein the second crosslinked zwitterionic polymer is a poly(carboxybetaine), poly(sulfobetaine), poly(sulfabetaine), poly(phosphobetaine), poly(phosphorylcholine), poly(choline phosphate), poly(trimethylamine-N-oxide), or a latent derivative thereof.

21. The double network hydrogel of claim 2 , wherein the first crosslinked zwitterionic polymer is a poly(carboxybetaine) and the second crosslinked zwitterionic polymer is a poly(sulfobetaine).

22. The double network hydrogel of claim 2 , wherein the first crosslinked zwitterionic polymer is a poly(sulfobetaine) and the second crosslinked zwitterionic polymer is a poly(sulfobetaine).

23. The double network hydrogel of claim 2 , wherein the first crosslinked zwitterionic polymer is a poly(trimethylamine-N-oxide) and the second crosslinked zwitterionic polymer is a poly(sulfobetaine).

24. The double network hydrogel of claim 2 , wherein the first crosslinked zwitterionic polymer is a poly(phosphorylcholine) and the second crosslinked zwitterionic polymer is a poly(sulfobetaine).

25. The double network hydrogel of claim 2 , wherein the second crosslinked zwitterionic polymer is a poly(sulfobetaine).

26. The double network hydrogel of claim 2 having a tensile fracture stress greater than about 0.3 MPa, a tensile fracture strain greater than about 200%, or a Young's modulus greater than about 0.01 MPa.

27. The double network hydrogel of claim 2 having a fibrinogen binding level of less than about 20% relative to that of tissue culture polystyrene tested via a fibrinogen binding assay in which a polymer surface is incubated at 37° C. for 90 minutes with a 1.0 mg/mL fibrinogen solution in 0.15 M phosphate buffered saline at pH 7.4.

28. The double network hydrogel of claim 2 obtained by a two-step process, wherein the first polymeric network is formed, and then the first polymeric network is soaked to equilibrium in a solution comprising precursors of the second polymeric network, followed by the polymerization of the precursors to provide the double network.

29. The double network hydrogel of claim 2 obtained by a single-pot process, wherein the second polymeric network is formed by (a) monomer polymerization, (b) comonomer copolymerization, or (c) physical crosslinking of a zwitterionic polymer or zwitterionic copolymer in the presence of the first polymeric network.

30. An article of manufacture comprising, in whole or in part, a double network hydrogel of claim 2 .

31. A microgel, comprising a double network hydrogel of claim 2 .

32. A surface coating for a substrate, comprising a double network hydrogel of claim 2 .

33. The double network hydrogel of claim 1 , wherein the first cr

Assignees

• Univ Washington

Inventors

• Jiang Shaoyi
• Hung Hsiang-Chieh
• Dong Dianyu
• Tsao Caroline
• Tang Chenjue
• Macarthur Joel

Classifications

• A61L24/0031

  Hydrogels or hydrocolloids · CPC title

• C08J2433/24

  Homopolymers or copolymers of amides or imides · CPC title

• C08J2433/22

  Homopolymers or copolymers of nitriles containing four or more carbon atoms · CPC title

• C08J2433/14

  of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen · CPC title

• C08J2333/24

  Homopolymers or copolymers of amides or imides · CPC title