# US 11,077,228 B2 · Interpenetrating polymer networks

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- Number: US 11,077,228 B2
- Document ID: US11077228B2
- Status: Granted
- Kind: B2
- Application number: 16/251,966
- Filed: 2019-01-18
- Published: 2019-07-25
- Granted: 2021-08-03
- Earliest claimed: 2015-08-10
- Assignees: Hyalex Orthopaedics, Inc.
- Applicants: Hyalex Orthopaedics, Inc.
- Inventors: Lampros Kourtis; Iraklis Kourtis; Jun Li; Gary Li
- Web page: https://patentgrep.com/patent/US11077228B2

## CPC

- A61L 27/34: Macromolecular materials
- A61F 2/28: Bones
- A61L 27/26: Mixtures of macromolecular compounds
- A61L 27/52: Hydrogels or hydrocolloids
- C08F 283/006: {on to polymers provided for in C08G18/00 (C08F283/004 takes precedence)}
- C08F 285/00: Macromolecular compounds obtained by polymerising monomers on to preformed graft polymers
- C08G 18/48: Polyethers
- C08G 18/83: Chemically modified polymers
- C08J 3/246: {Intercrosslinking of at least two polymers}
- C08L 33/066: {containing -OH groups}
- C08L 33/26: Homopolymers or copolymers of acrylamide or methacrylamide
- C08L 75/04: Polyurethanes
- C08L 101/14: the macromolecular compounds being water soluble or water swellable, e.g. aqueous gels
- A61F 2/32: for the hip
- A61F 2/38: for elbows or knees
- A61F 2/40: for shoulders
- A61F 2/42: for wrists or ankles; for hands, e.g. fingers; for feet, e.g. toes
- A61L 2400/10: Materials for lubricating medical devices
- C08G 2270/00: Compositions for creating interpenetrating networks
- C08L 2205/04: containing interpenetrating networks
- 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)
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)

## Abstract

IPN compositions and methods of making the same are provided. The IPN compositions can include a water swellable, water permeable IPN or semi-IPN member with a first polymer network including a hydrophobic thermoset or thermoplastic polymer, a second polymer network including a non-ionic polymer, and a third polymer network including an ionic polymer containing sulfonic acid functional groups that are otherwise difficult to form composites with hydrophobic polymers. The IPN compositions can be used in orthopedic implants or in mechanical applications as a bearing material.

## Claims

### Claim 1

An interpenetrating polymer network (IPN) or semi-IPN member comprising a first polymer network including a hydrophobic thermoset or thermoplastic polymer including multiple subsets of polymer segments, a second polymer network comprising a polymerized non-ionic monomer, and a third polymer network including an ionic polymer containing sulfonic acid groups, wherein the second network is non-ionic, the third network is ionic, the second and third polymer networks are each formed within the same subset of polymer segments of the hydrophobic thermoset or thermoplastic polymer, and the first, second, and third polymer networks are not bonded to each other covalently.

### Claim 2 (depends on 1)

The IPN or semi-IPN member of claim 1, wherein the IPN or semi-IPN member comprises a lubricious surface having a coefficient of friction of less than about 0.1.

### Claim 3 (depends on 1)

The IPN or semi-IPN member of claim 1, wherein the first polymer network comprises a polyurethane.

### Claim 4 (depends on 1)

The IPN or semi-IPN member of claim 1, wherein the second polymer network comprises one or more polymerized non-ionic monomers selected from dimethylacrylamide (DMAA), acrylamide, N-isopropyl acrylamide (NIPAAm), hydroxyethyl acrylate, hydroxyethyl methacrylate, vinyl alcohol, methyl acrylate, hydroxyethyl acrylamide, hydroxyethyl methacrylamide, and N-vinyl pyrrolidone.

### Claim 5 (depends on 1)

The IPN or semi-IPN member of claim 1, wherein the second polymer network comprises a plurality of different monomers.

### Claim 6 (depends on 1)

The IPN or semi-IPN member of claim 1, wherein the ionic polymer containing sulfonic acid groups comprises a polymerized monomer having sulfonic acid functional groups.

### Claim 7 (depends on 1)

The IPN or semi-IPN member of claim 1, wherein the ionic polymer containing sulfonic acid groups comprises a polymerized macromer having sulfonic acid functional groups.

### Claim 8 (depends on 1)

The IPN or semi-IPN member of claim 1, wherein the ionic polymer containing sulfonic acid groups comprises a polymerized sulfonate-containing monomer selected from acrylamide methyl propane sulfonic acid (AMPS), 2-Propene-1-sulfonic acid, 1,3-Propanesulfone, 1,4 butane sulfone, anetholesulfonic acid, styrenesulfonic acid, vinyl sulfonic acid, 3-sulfopropyl acrylate, 3-sulfopropyl methacrylate, or 2-methyl-2-propene-1-sulfonic acid.

### Claim 9 (depends on 1)

The IPN or semi-IPN member of claim 1, wherein the second polymer network, the third polymer network, or both is polymerized in the presence of a cross-linker.

### Claim 10 (depends on 9)

The IPN or semi-IPN member of claim 9, wherein the cross-linker is selected from ethylene glycol dimethacrylate, ethylene glycol diacrylate, diethylene glycol dimethacrylate (or diacrylate), triethylene glycol dimethacrylate (or diacrylate), tetraethylene glycol dimethacrylate (or diacrylate), polyethylene glycol dimethacrylate, or polyethylene glycol diacrylate, methylene bisacrylamide, N,N′-(1,2-dihydroxyethylene) bisacrylamide, derivatives, or combinations thereof.

### Claim 11 (depends on 1)

An orthopedic implant comprising the IPN or semi-IPN of claim 1.

### Claim 12 (depends on 11)

The orthopedic implant of claim 11, wherein the orthopedic implant is adapted to fit an acromioclavicular joint, an ankle joint, a condyle, an elbow joint, a hand joint including a metacarpal joint, a finger joint, a thumb joint, a base of thumb joint, a glenoid, a hip joint including an acetabular joint, an intervertebral disc, a vertebral joint, including an intervertebral facet joint, a labrum, a meniscus, a foot joint, including a metatarsal joint and a toe joint, a patella, a tibial plateau, a jaw joint including a temporomandibular joint, a knee joint including a knee medial compartment joint, a patellofemoral joint, and a total knee joint, a knee meniscus, a shoulder joint including a labral joint, or a wrist joint and any portion thereof.

### Claim 13 (depends on 11)

The orthopedic implant of claim 11, wherein the orthopedic implant is selected from cartilage replacement devices, joint replacement devices, meniscal replacements, interpositional spaces, tendon or ligament replacement or augmentation devices, cartilage scaffolds, cartilage replacement plugs, cartilage stimulation plugs, bone filler implants to stimulate cartilage regeneration, and facet or vertebral disc implants.

### Claim 14 (depends on 11)

The orthopedic implant of claim 11, wherein the IPN or semi-IPN member comprises a bearing surface and an attachment zone.

### Claim 15 (depends on 14)

The orthopedic implant of claim 14, wherein the bearing surface has a coefficient of friction of less than about 0.1.

### Claim 16 (depends on 15)

The orthopedic implant of claim 15, comprising a bone interface member attached to the attachment zone.

### Claim 17 (depends on 16)

The orthopedic implant of claim 16, wherein the bone interface member comprises a metal.