# US 10,869,950 B2 · Ionic polymer compositions

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- Number: US 10,869,950 B2
- Document ID: US10869950B2
- Status: Granted
- Kind: B2
- Application number: 16/514,279
- Filed: 2019-07-17
- Published: 2020-01-23
- Granted: 2020-12-22
- Earliest claimed: 2018-07-17
- Assignees: Hyalex Orthopaedics, Inc.
- Applicants: Hyalex Orthopaedics, Inc.
- Inventors: Iraklis Kourtis; Jun Li; Lampros Kourtis
- Web page: https://patentgrep.com/patent/US10869950B2

## CPC

- A61L 27/34: Macromolecular materials
- A61F 2/0095: {Packages or dispensers for prostheses or other implants (for intraocular lenses A61F2/1691; for dental surgery A61C19/02)}
- A61F 2/30756: {Cartilage endoprostheses (A61F2/3603 takes precedence)}
- A61F 2/3099: {for temporo-mandibular [TM, TMJ] joints (endoprostheses for mandibular reconstruction A61F2/2803)}
- A61F 2/32: for the hip
- A61F 2/3804: {for elbows}
- A61F 2/3872: {Meniscus for implantation between the natural bone surfaces}
- A61F 2/3877: {Patellae or trochleae}
- A61F 2/389: {Tibial components (A61F2/3868 takes precedence)}
- A61F 2/4081: {Glenoid components, e.g. cups}
- A61F 2/4202: {for ankles}
- A61F 2/4225: {for feet, e.g. toes}
- A61F 2/4241: {for hands, e.g. fingers}
- A61F 2/4261: {for wrists}
- A61F 2/4405: {for apophyseal or facet joints, i.e. between adjacent spinous or transverse processes (devices implanted between spinous or transverse processes A61B17/7062)}
- A61F 2/442: {Intervertebral or spinal discs, e.g. resilient (non-disc-shaped intervertebral inflatable pockets A61F2/441; non-disc-shaped intervertebral fusion implants A61F2/4455)}
- A61L 27/18: obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- A61L 27/26: Mixtures of macromolecular compounds
- A61L 27/48: with macromolecular fillers
- A61L 27/52: Hydrogels or hydrocolloids
- A61F 2/44: for the spine, e.g. vertebrae or spinal discs
- A61L 2400/18: Modification of implant surfaces in order to improve biocompatibility, cell growth, fixation of biomolecules, e.g. plasma treatment
- A61L 2430/24: for joint reconstruction
- A61L: METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES (preservation of bodies or disinfecting characterised by the agents employed A01N; preserving, e.g. sterilising, food or foodstuffs A23; preparations for medical, dental or toiletry purposes A61K)
- A61F: FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS (dental prosthetics A61C)

## 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

### Claim 1

An orthopedic implant comprising 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, and the crosslinked ionic polymer has a thickness of up to 10 mm.

### Claim 2 (depends on 1)

The orthopedic implant of claim 1, wherein the sulfonic-acid-derivatized groups are amino-sulfonic-acid-derivatized groups.

### Claim 3 (depends on 2)

The orthopedic implant of claim 2, wherein the crosslinked ionic polymer comprises a measurable amount of an amino sulfonic acid compound of the formula (H2N)xR(SO3H)y or a salt thereof, where R is an organic moiety, x is a positive integer and y is a positive integer.

### Claim 4 (depends on 3)

The orthopedic implant of claim 3, wherein R is a hydrocarbon moiety.

### Claim 5 (depends on 4)

The orthopedic implant 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.

### Claim 6 (depends on 4)

The orthopedic implant of claim 4, wherein the hydrocarbon moiety is a C1-C12 hydrocarbon moiety.

### Claim 7 (depends on 2)

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

### Claim 8 (depends on 1)

The orthopedic implant of claim 1, wherein the sulfonic-acid-derivatized groups are sulfonic-acid-derivatized carboxylic groups.

### Claim 9 (depends on 8)

The orthopedic implant of claim 8, wherein the crosslinked ionic polymer further comprises underivatized carboxylic acid groups.

### Claim 10 (depends on 9)

The orthopedic implant 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.

### Claim 11 (depends on 1)

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

### Claim 12 (depends on 1)

The orthopedic implant 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.

### Claim 13 (depends on 1)

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

### Claim 14 (depends on 1)

The orthopedic implant of claim 1, wherein the sulfonic-acid-derivatized groups are present throughout greater than 50% of the thickness of the crosslinked ionic polymer.

### Claim 15 (depends on 1)

The orthopedic implant of claim 1, wherein the sulfonic-acid-derivatized groups are present throughout greater than 75% of the thickness of the crosslinked ionic polymer.

### Claim 16 (depends on 1)

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

### Claim 17 (depends on 1)

The orthopedic implant 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.

### Claim 18 (depends on 1)

The orthopedic implant 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.

### Claim 19 (depends on 9)

The orthopedic implant 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.

### Claim 20 (depends on 9)

The orthopedic implant 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.

### Claim 21 (depends on 9)

The orthopedic implant 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.

### Claim 22 (depends on 9)

The orthopedic implant 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 crosslinked ionic polymer and at least one point in the bulk of the crosslinked ionic polymer.

### Claim 23 (depends on 1)

The orthopedic implant 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.

### Claim 24 (depends on 23)

The orthopedic implant of claim 23, wherein the first polymer is a hydrophobic polymer.

### Claim 25 (depends on 23)

The orthopedic implant of claim 23, wherein the first polymer is a thermoplastic polymer.

### Claim 26 (depends on 23)

The orthopedic implant of claim 23, wherein the first polymer is a polyurethane.

### Claim 27 (depends on 23)

The orthopedic implant of claim 23, 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.

### Claim 28 (depends on 1)

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

### Claim 29 (depends on 28)

The orthopedic implant of claim 28, 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.

### Claim 30

An interpenetrating or semi-interpenetrating polymer network that comprises a first polymeric network comprising a first polymer and a second polymeric network comprising a crosslinked ionic polymer that comprises sulfonic-acid-derivatized groups, wherein the sulfonic-acid-derivatized groups are present at a surface of the interpenetrating or semi-interpenetrating polymer network and extend into the interpenetrating or semi-interpenetrating polymer network by a distance of at least 500 microns, and the interpenetrating or semi-interpenetrating polymer network has a thickness of up to 10 mm.

### Claim 31 (depends on 30)

The interpenetrating or semi-interpenetrating polymer network of claim 30, wherein the sulfonic-acid-derivatized groups are amino-sulfonic-acid-derivatized groups.

### Claim 32 (depends on 30)

The interpenetrating or semi-interpenetrating polymer network of claim 30, wherein the sulfonic-acid-derivatized groups are sulfonic-acid-derivatized carboxylic groups.

### Claim 33 (depends on 30)

The interpenetrating or semi-interpenetrating polymer network of claim 30, wherein the crosslinked ionic polymer further comprises underivatized carboxylic acid groups.

### Claim 34 (depends on 30)

The interpenetrating or semi-interpenetrating polymer network of any of claim 30, wherein the first polymer is hydrophobic polymer.

### Claim 35 (depends on 30)

The interpenetrating or semi-interpenetrating polymer network of claim 30, wherein the first polymer is a thermoplastic polymer.

### Claim 36 (depends on 30)

The interpenetrating or semi-interpenetrating polymer network of claim 30, wherein the first polymer is a polyurethane.

### Claim 37 (depends on 36)

The interpenetrating or semi-interpenetrating polymer network of claim 36, wherein the polyurethane is a polyether urethane.

### Claim 38 (depends on 30)

The interpenetrating or semi-interpenetrating polymer network of claim 30, having 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.

### Claim 39 (depends on 34)

The interpenetrating or semi-interpenetrating polymer network of claim 34, wherein the hydrophobic polymer is a polyurethane and wherein at least a portion of the underivatized carboxylic acid groups correspond to underivatized acrylic acid polymerized monomers within the ionic polymer.

### Claim 40 (depends on 30)

The interpenetrating or semi-interpenetrating polymer network of claim 30, wherein the sulfonic-acid-derivatized groups are present throughout greater than 20% of the thickness of the interpenetrating or semi-interpenetrating polymer network.

### Claim 41 (depends on 30)

The interpenetrating or semi-interpenetrating polymer network of claim 30, wherein the sulfonic-acid-derivatized groups are present throughout greater than 50% of the thickness of the interpenetrating or semi-interpenetrating polymer network.

### Claim 42 (depends on 30)

The interpenetrating or semi-interpenetrating polymer network of claim 30, wherein the sulfonic-acid-derivatized groups are present throughout greater than 75% of the thickness of the interpenetrating or semi-interpenetrating polymer network.

### Claim 43 (depends on 30)

The interpenetrating or semi-interpenetrating polymer network of claim 30, wherein the sulfonic-acid-derivatized groups are present throughout 100% of the thickness of the interpenetrating or semi-interpenetrating polymer network.