IP Library Granted Patent US 11,771,802
Granted Patent B2
US 11,771,802 · App. 17/749,699 · Granted Oct 3, 2023

Ionic polymer compositions

Inventors: Iraklis Kourtis (Arlington, MA); Jun Li (Winchester, MA); Lampros Kourtis (Cambridge, MA)
Assignee: Hyalex Orthopaedics, 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 11,771,802
App. No.
17/749,699
Granted
Oct 3, 2023
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 (24)

1. A method of making a water-swellable interpenetrating polymer network (IPN) or semi-interpenetrating polymer network (semi-IPN) comprising sulfonic-acid-derivatized groups, comprising the steps of:

(1) providing an IPN or semi-IPN comprising a first polymeric network comprising a hydrophobic thermoset or thermoplastic polymer and second polymeric network comprising a precursor polymer, wherein the precursor polymer comprises carboxylic acid groups; and

( 2 ) reacting the carboxylic acid groups with a sulfonic-acid containing compound in the presence of a triazine-based coupling reagent to form sulfonic-acid-derivatized groups.

2. The method of claim 1 , wherein step (2) comprises:

(i) contacting the IPN or semi-IPN comprising a hydrophobic thermoset or thermoplastic polymer and the precursor polymer with the sulfonic-acid containing compound; and

(ii) contacting IPN or semi-IPN comprising a hydrophobic thermoset or thermoplastic polymer and the precursor polymer with the triazine-based coupling reagent.

3. The method of claim 1 , wherein step (2) comprises:

(i) contacting the IPN or semi-IPN comprising a hydrophobic thermoset or thermoplastic polymer and the precursor polymer with the triazine-based coupling reagent; and

(ii) contacting IPN or semi-IPN comprising a hydrophobic thermoset or thermoplastic polymer and the precursor polymer with the sulfonic-acid-containing compound.

4. The method of claim 1 , wherein step (2) comprises contacting the IPN or semi-IPN comprising a hydrophobic thermoset or thermoplastic polymer and the precursor polymer with the sulfonic-acid-containing compound and the triazine-based coupling reagent simultaneously.

5. The method of claim 1 , wherein the providing the IPN or semi-IPN comprising the first polymeric network comprising the hydrophobic thermoset or thermoplastic polymer and second polymeric network comprising the precursor polymer comprises:

providing a hydrophobic thermoset or thermoplastic polymer;

diffusing monomers comprising carboxylic-acid-group-containing monomers into the hydrophobic thermoset or thermoplastic monomer; and

polymerizing the monomers to form the precursor polymer.

6. The method of claim 1 , wherein the hydrophobic thermoset or thermoplastic polymer is a polyurethane.

7. The method of claim 6 , wherein the hydrophobic thermoset or thermoplastic polymer is polyetherurethane.

8. The method of claim 1 , wherein the sulfonic-acid derivatized groups are amino-sulfonic-acid-derivatized groups, and the sulfonic-acid-containing compound is amino sulfonic acid of formula (H 2 N) x R(SO 3 H) y or a salt thereof, wherein R is an organic moiety, x is a positive integer, and y is a positive integer.

9. The method of claim 8 , wherein R is a hydrocarbon moiety.

10. The method of claim 9 , 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.

11. The method of claim 10 , wherein the hydrocarbon moiety is a C 1 -C 12 hydrocarbon moiety.

12. The method of claim 11 wherein the amino sulfonic acid is taurine or a derivative thereof.

13. The method of claim 1 , wherein the precursor polymer is poly(acrylic acid), poly(methacrylic acid), poly(crotonic acid), poly(linolenic acid), poly(maleic acid), and poly(fumaric acid).

14. The method of claim 13 , wherein the precursor polymer is poly(acrylic acid).

15. The method of claim 1 , wherein the triazine-based coupling reagent is 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMTMM).

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 Apr 25, 2023
From: KOURTIS, IRAKLIS; LI, JUN; KOURTIS, LAMPROS
To: HYALEX ORTHOPAEDICS, INC.
Reel/Frame 063433/0632 →
Continuity (6)
Continuation 17391212 · Aug 2, 2021
Continuation 17091787 · Nov 6, 2020
Continuation 16514279 · Jul 17, 2019
Continuation In Part 16246292 · Jan 11, 2019
Provisional Application 62699497 · Jul 17, 2018
Related Publication 20220273846A1 · Sep 1, 2022