IP Library Granted Patent US 10,792,392
Granted Patent B2
US 10,792,392 · App. 16/656,311 · Granted Oct 6, 2020

Ionic polymer compositions

Inventors: Iraklis Kourtis (Arlington, MA); Jun Li (Winchester, MA); Lampros Kourtis (Cambridge, MA)
Assignee: Hyalex Orthopedics, Inc.
A61L27/34A61F2/0095A61F2/3099A61F2/30756A61F2/32A61F2/3804A61F2/389A61F2/3872A61F2/3877A61F2/4081A61F2/4202A61F2/4225A61F2/4241A61F2/4261A61F2/442A61F2/4405A61L27/18A61L27/26A61L27/48
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Quick Facts
Patent No.
US 10,792,392
App. No.
16/656,311
Granted
Oct 6, 2020
Kind
B2
Abstract

The present disclosure pertains to ionic polymer compositions, including semi- and fully interpenetrating polymer networks, methods of making such ionic polymer compositions, articles made from such ionic polymer compositions, and methods of making such articles and packaging for such articles.

Claims (26)

1. A packaged article comprising an orthopedic implant and a divalent-cation-containing solution contained within a sterile package, wherein the orthopedic implant comprises a crosslinked ionic polymer that comprises sulfonic-acid-derivatized groups, wherein the sulfonic-acid-derivatized groups are present at a surface of the crosslinked ionic polymer and extend from the surface into a bulk of the crosslinked ionic polymer by a distance of at least 500 microns, said crosslinked ionic polymer has a thickness of up to 10 mm, and the divalent-cation-containing solution comprises 0.5 to 5.0 mM calcium ions and 0.2 to 1.5 mM magnesium ions.

2. The packaged article of claim 1 , wherein the sulfonic-acid-derivatized groups are amino-sulfonic-acid-derivatized groups.

3. The packaged article of claim 2 , wherein the crosslinked-ionic polymer comprises a measurable amount of an amino sulfonic acid compound of the formula (H 2 N) x R(SO 3 H) y or a salt thereof, where R is an organic moiety, x is a positive integer and y is a positive integer.

4. The packaged article of claim 3 , wherein R is a hydrocarbon moiety.

5. The packaged article of claim 4 , wherein the hydrocarbon moiety is an alkane moiety, an alkene moiety, an alkyne moiety, an aromatic moiety, or a hydrocarbon moiety having a combination of two or more of alkane, alkene, alkyne and aromatic substituents.

6. The packaged article of claim 4 , wherein the hydrocarbon moiety is a C 1 -C 12 hydrocarbon moiety.

7. The packaged article of claim 2 , wherein the crosslinked-ionic polymer comprises a measurable amount of an amino sulfonic acid compound selected from taurine and taurine derivatives.

8. The packaged article of claim 1 , wherein the sulfonic-acid-derivatized groups are sulfonic-acid-derivatized carboxylic groups.

9. The packaged article of claim 8 , wherein the crosslinked ionic polymer further comprises underivatized carboxylic acid groups.

10. The packaged article of claim 9 , wherein the underivatized carboxylic acid groups correspond to one or more of the following: underivatized acrylic acid polymerized monomers within the ionic polymer, underivatized methacrylic acid polymerized monomers within the ionic polymer, underivatized crotonic acid polymerized monomers within the ionic polymer, underivatized linolenic acid polymerized monomers within the ionic polymer, underivatized maleic acid polymerized monomers within the ionic polymer, and underivatized fumaric acid polymerized monomers within the ionic polymer, and wherein the amino-sulfonic-acid-derivatized carboxylic acid groups correspond to one or more of amino sulfonic-acid-derivatized acrylic acid polymerized monomers within the ionic polymer, amino-sulfonic-acid-derivatized methacrylic acid polymerized monomers within the ionic polymer, amino-sulfonic-acid-derivatized crotonic acid polymerized monomers within the ionic polymer, amino-sulfonic-acid-derivatized linolenic acid polymerized monomers within the ionic polymer, amino-sulfonic-acid-derivatized maleic acid polymerized monomers within the ionic polymer, and amino-sulfonic-acid-derivatized fumaric acid polymerized monomers within the ionic polymer.

11. The packaged article of claim 1 , wherein the crosslinked-ionic polymer comprises a gradient in a concentration of the sulfonic-acid-derivatized groups.

12. The packaged article of claim 1 , wherein the sulfonic-acid-derivatized groups extend into the bulk of the crosslinked-ionic polymer by a distance of at least 1 mm.

13. The packaged article of claim 1 , wherein the sulfonic-acid-derivatized groups are present throughout greater than 20% of the thickness of the crosslinked-ionic polymer.

14. The packaged article of claim 1 , wherein the sulfonic-acid-derivatized groups are present throughout 100% of the thickness of the crosslinked-ionic polymer.

15. The packaged article of claim 1 , wherein a concentration of the sulfonic-acid-derivatized groups decreases by at least 10% from the point on the surface of the crosslinked-ionic polymer and at least one point in the bulk of the crosslinked-ionic polymer.

16. The packaged article of claim 1 , wherein a concentration of the sulfonic-acid-derivatized groups does not vary by more than +/−10% between any two points in the crosslinked-ionic polymer.

17. The packaged article of claim 9 , wherein a concentration of the sulfonic-acid-derivatized carboxylic acid groups and a concentration of the underivatized carboxylic acid groups do not vary by more than +/−10% between any two points in the crosslinked-ionic polymer.

18. The packaged article of claim 9 , wherein the crosslinked-ionic polymer comprises a gradient in a concentration of the sulfonic-acid-derivatized carboxylic acid groups and a gradient in a concentration of the underivatized carboxylic acid groups.

19. The packaged article of claim 9 , wherein a concentration of the sulfonic-acid-derivatized carboxylic acid groups decreases by at least 10% from the point on the surface of the crosslinked-ionic polymer and at least one point in the bulk of the crosslinked-ionic polymer, and wherein a concentration of the underivatized carboxylic acid groups increases by at least 10% from the point on the surface of the crosslinked-ionic polymer and at least one point in the bulk of the crosslinked-ionic polymer.

20. The packaged article of claim 9 , wherein a molar ratio of the sulfonic-acid-derivatized carboxylic acid groups to the underivatized carboxylic acid groups decreases by at least 10% from the point on the surface of the implant and at least one point in the bulk of the crosslinked-ionic polymer.

21. The packaged article of claim 1 , wherein the implant comprises an interpenetrating or semi-interpenetrating polymer network that comprises a first polymeric network comprising a first polymer and a second polymeric network comprising the ionic polymer.

22. The packaged article of claim 21 , wherein the first polymer is a hydrophobic polymer.

23. The packaged article of claim 21 , wherein the first polymer is a thermoplastic polymer.

24. The packaged article of claim 21 , wherein the interpenetrating or semi-interpenetrating polymer network has first and second surfaces, wherein the first surface has a composition corresponding to the first polymer and wherein a concentration of the sulfonic-acid-derivatized groups is at a maximum at the second surface and decreases to zero or substantially zero concentration within the bulk of the interpenetrating or semi-interpenetrating polymer network.

25. The packaged article of claim 1 , wherein the implant is configured to repair or replace cartilage in a joint in the body.

26. The packaged article of claim 25 , wherein the joint in the body is selected from a knee joint, a condyle, a patella, a tibial plateau, an ankle joint, an elbow joint, a shoulder joint, a finger joint, a thumb joint, a glenoid, a hip joint, an intervertebral disc, an intervertebral facet joint, a labrum, a meniscus, a metacarpal joint, a metatarsal joint, a toe joint, a temporomandibular joint, and a wrist joint, including portions thereof.

Assignments (2)
SECURITY INTEREST Recorded Feb 7, 2024
From: HYALEX ORTHOPAEDICS, INC.
To: CUSTOMERS BANK
Reel/Frame 066406/0253 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 12, 2020
From: KOURTIS, IRAKLIS; LI, JUN; KOURTIS, LAMPROS
To: HYALEX ORTHOPAEDICS, INC.
Reel/Frame 052922/0486 →
Continuity (4)
Continuation 16514279 · Jul 17, 2019
Continuation In Part 16246292 · Jan 11, 2019
Provisional Application 62699497 · Jul 17, 2018
Related Publication 20200046880A1 · Feb 13, 2020
Cited By (3)
US 12,202,788 US 12,623,212 US 12,686,743