# US 11,110,200 B2 · Ionic polymer compositions

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- Number: US 11,110,200 B2
- Document ID: US11110200B2
- Status: Granted
- Kind: B2
- Application number: 17/091,787
- Filed: 2020-11-06
- Published: 2021-02-25
- Granted: 2021-09-07
- 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/US11110200B2

## 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

A packaged article comprising an orthopedic implant and a divalent-cation-containing solution contained within a sterile package, wherein the orthopedic implant comprises an interpenetrating polymer network (IPN) or semi-IPN that comprises a first polymeric network comprising a hydrophobic thermoset or thermoplastic polymer and a second polymeric network comprising a polymer comprising carboxylic acid groups that are underivatized or sulfonic-acid-derivatized, and the divalent-cation-containing solution comprises 0.1 to 5 mM divalent metal cations comprising Ca2+.

### Claim 2 (depends on 1)

The packaged article of claim 1, wherein the IPN or semi-IPN has first and second surfaces, wherein the first surface has a composition corresponding to the hydrophobic thermoset or thermoplastic polymer and wherein a concentration of the carboxylic acid groups is at a maximum at the second surface and decreases to zero or substantially zero concentration within a bulk of the IPN or semi-IPN, and the carboxylic acid groups are underivatized carboxylic acid groups, sulfonic-acid-derivatized carboxylic acid groups, or a mixture thereof.

### Claim 3 (depends on 2)

The packaged article of claim 2, wherein the polymer having carboxylic acid groups comprises one or more monomers selected from acrylic acid, methacrylic acid, crotonic acid, linolenic acid, maleic acid, and fumaric acid.

### Claim 4 (depends on 3)

The packaged article of claim 3, wherein the carboxylic acid groups are underivatized.

### Claim 5 (depends on 3)

The packaged article of claim 3, wherein the carboxylic acid groups include sulfonic-acid derivatized carboxylic acid groups.

### Claim 6 (depends on 5)

The packaged article of claim 5, wherein the sulfonic-acid-derivatized carboxylic acid groups are amino-sulfonic-acid-derivatized carboxylic acid groups.

### Claim 7 (depends on 6)

The packaged article of claim 6, wherein the second polymeric network 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 8 (depends on 7)

The packaged article of claim 7, wherein R is a hydrocarbon moiety.

### Claim 9 (depends on 8)

The packaged article of claim 8, 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 10 (depends on 9)

The packaged article of claim 9, wherein the hydrocarbon moiety is a C1-C12 hydrocarbon moiety.

### Claim 11 (depends on 10)

The packaged article of claim 10, wherein the amino sulfonic acid is taurine or a derivative thereof.

### Claim 12 (depends on 6)

The packaged article of claim 6, wherein the carboxylic acid groups further include underivatized carboxylic acid groups.

### Claim 13 (depends on 6)

The packaged article of claim 6, wherein the IPN or semi-IPN comprises a gradient in a concentration of the sulfonic-acid-derivatized carboxylic acid groups.

### Claim 14 (depends on 13)

The packaged article of claim 13, wherein a concentration of the sulfonic-acid-derivatized carboxylic acid groups decreases by at least 10% from a point on the second surface of the IPN or semi-IPN to at least one point in the bulk of the IPN or semi-IPN.

### Claim 15 (depends on 13)

The packaged article of claim 13, wherein a concentration of the sulfonic-acid-derivatized carboxylic acid groups does not vary by more than +/−10% between any two points in the IPN or semi-IPN.

### Claim 16 (depends on 12)

The packaged article of claim 12, wherein the IPN or semi-IPN comprises a gradient in a concentration of the sulfonic-acid-derivatized carboxylic acid groups.

### Claim 17 (depends on 16)

The packaged article of claim 16, 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 IPN or semi-IPN.

### Claim 18 (depends on 16)

The packaged article of claim 16, wherein the second polymeric network 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 19 (depends on 16)

The packaged article of claim 16, wherein a concentration of the sulfonic-acid-derivatized carboxylic acid groups decreases by at least 10% from a point on the second surface of the IPN or semi-IPN to at least one point in a bulk of the IPN or semi-IPN, and wherein a concentration of the underivatized carboxylic acid groups increases by at least 10% from the point on the second surface of the IPN or semi-IPN to at least one point in the bulk of the IPN or semi-IPN.

### Claim 20 (depends on 16)

The packaged article of claim 16, wherein a molar ratio of the sulfonic-acid-derivatized carboxylic acid groups to the underivatized carboxylic acid groups decreases by at least 10% from a point on the second surface of the IPN or semi-IPN to at least one point in the bulk of the IPN or semi-IPN.

### Claim 21 (depends on 1)

The packaged article of claim 1, wherein the first polymeric network comprises polyurethane.

### Claim 22 (depends on 21)

The packaged article of claim 21, wherein the first polymeric network comprises polyetherurethane.

### Claim 23 (depends on 1)

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

### Claim 24 (depends on 23)

The packaged article of claim 23, wherein the joint in the body is 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, a wrist joint, or a portion thereof.