IP Library Granted Patent US 8,617,519
Granted Patent B2
US 8,617,519 · App. 13/177,613 · Granted Dec 31, 2013

Injectable cross-linked hydrogels for biomaterial applications

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Quick Facts
Patent No.
US 8,617,519
App. No.
13/177,613
Granted
Dec 31, 2013
Kind
B2
Abstract

An injectable hydrogel composition comprising: water; and poly(vinyl alcohol) chemically cross-linked with a second polymer to form a cross-linked resin, wherein the second polymer is selected from the group consisting of: a polyhydric alcohol compound, a polyvalent epoxy compound, a polyvalent amine compound, a dialdehyde compound, a diisocyanate compound, and mixtures thereof, wherein the cross-linked resin has a degree of cross-linking of from about 0.0001 mol/mL to about 0.002 mol/mL, and wherein the hydrogel is flowable when heated above its melting point.

Claims (24)

1. An injectable hydrogel composition comprising:

water; and

poly(vinyl alcohol) chemically cross-linked with a second polymer to form a cross-linked resin, wherein the second polymer is selected from the group consisting of: a polyhydric alcohol compound, a polyvalent epoxy compound, a polyvalent amine compound, a dialdehyde compound, a diisocyanate compound, and mixtures thereof,

wherein the cross-linked resin has a degree of chemical cross-linking of from about 0.0001 mol/mL to about 0.002 mol/mL, wherein the hydrogel is flowable when heated above its melting point, and wherein the hydrogel composition exhibits a swelling value of from about 1.033 to about 1.79 in a 0.16 MPa osmotic solution.

2. The hydrogel composition of claim 1 wherein the poly(vinyl alcohol) is present in the composition at a concentration of from about 14% (w/w) to about 21% (w/w).

3. The hydrogel composition of claim 1 wherein the second polymer is a polyvalent epoxy compound.

4. The hydrogel composition of claim 3 , wherein the polyvalent epoxy compound is poly(ethylene glycol) diglycidyl ether.

5. The hydrogel composition of claim 3 wherein the poly(ethylene glycol) diglycidyl ether is present in the composition at a concentration of from about 6% (w/w) to about 40% (w/w).

6. The hydrogel composition of claim 1 further comprising polyvinyl pyrrolidone.

7. The hydrogel composition of claim 6 wherein the poly(vinyl pyrrolidone) is present in the composition at a concentration of from about 0.14% (w/w) to about 0.22% (w/w).

8. The hydrogel composition of claim 4 wherein the poly(ethylene glycol) diglycidyl ether has a molecular weight of from about 526 Da to about 4600 Da.

9. The hydrogel composition of claim 1 further comprising an imaging agent.

10. The hydrogel composition of claim 9 , where the imaging agent is barium sulfate.

11. The hydrogel composition of claim 1 wherein the composition exhibits a swelling volume change of about 11% to about 17% in a 0.16 MPa osmotic solution.

12. The hydrogel composition of claim 1 wherein the composition has a viscosity of from about 11 Pa*s to about 77 Pa*s at a temperature of 95° C.

13. The hydrogel composition of claim 8 wherein the poly(ethylene glycol) diglycidyl has a molecular weight of about 526 Da and the composition has an elastic modulus of from about 0.03 MPa to about 1.8 MPa.

14. The hydrogel composition of claim 1 wherein the cross-linked resin has a degree of cross-linking of from about 0.0007 mol/mL to about 0.0011 mol/mL.

15. The hydrogel composition of claim 14 wherein the cross-linked resin has a degree of cross-linking of about 0.0009 mol/mL+/−0.0002 mol/mL.

16. The hydrogel composition of claim 1 wherein the second polymer is poly(ethylene glycol) at a concentration of from about 12% (w/w) to about 18% (w/w).

17. The hydrogel composition of claim 16 further comprising an imaging agent.

18. The hydrogel composition of claim 17 wherein the imaging agent is barium sulfate.

19. The hydrogel composition of claim 5 wherein the poly(ethylene glycol) diglycidyl ether is present in the composition at a concentration of from about 19% (w/w) to about 38% (w/w).

20. The hydrogel composition of claim 19 wherein the poly(ethylene glycol) diglycidyl ether is present in the composition at a concentration of from about 27% (w/w) to about 38% (w/w).

21. The hydrogel composition of claim 1 wherein hydrogel composition exhibits a swelling volume change of about 11% to about 17% in a 0.16 MPa osmotic solution.

Assignments (6)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 8, 2021
From: DREXEL UNIVERSITY
To: REGELTEC, INC.
Reel/Frame 054854/0336 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 28, 2018
From: DEPUY SYNTHES PRODUCTS, INC.
To: REGELTEC, INC
Reel/Frame 047871/0169 →
CHANGE OF NAME Recorded Dec 28, 2018
From: DEPUY SYNTHES PRODUCTS, LLC
To: DEPUY SYNTHES PRODUCTS, INC.
Reel/Frame 047994/0714 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 6, 2013
From: SYNTHES USA, LLC
To: DEPUY SPINE, LLC
Reel/Frame 030358/0945 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 6, 2013
From: DEPUY SPINE, LLC
To: HAND INNOVATIONS LLC
Reel/Frame 030359/0001 →
CHANGE OF NAME Recorded May 6, 2013
From: HAND INNOVATIONS LLC
To: DEPUY SYNTHES PRODUCTS, LLC
Reel/Frame 030359/0036 →