# US 10,766,995 B2 · Polyurethanes

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- Number: US 10,766,995 B2
- Document ID: US10766995B2
- Status: Granted
- Kind: B2
- Application number: 15/537,386
- Filed: 2015-12-18
- Published: 2018-01-18
- Granted: 2020-09-08
- Earliest claimed: 2014-12-19
- Assignees: Strait Access Technologies Holdings (Pty) Ltd
- Applicants: Strait Access Technologies Holdings (Pty) Ltd
- Inventors: Arthur Coury; Deon Bezuidenhout; Jandré De Villiers; Johan Coetzee; David Gideon Conradie
- Web page: https://patentgrep.com/patent/US10766995B2

## CPC

- C08G 18/3206: {aliphatic}
- A61L 27/18: obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- A61L 27/507: {for artificial blood vessels (apparatus for applying cells on a blood vessel prosthesis A61F2/062)}
- C08G 18/3212: {containing cycloaliphatic groups}
- C08G 18/3228: {acyclic}
- C08G 18/3234: {cycloaliphatic}
- C08G 18/3243: {containing two or more aromatic rings}
- C08G 18/3246: {heterocyclic, the heteroatom being oxygen or nitrogen in the form of an amino group}
- C08G 18/3271: {Hydroxyamines}
- C08G 18/3281: {containing three hydroxy groups}
- C08G 18/3284: {containing four hydroxy groups}
- C08G 18/329: {containing aromatic groups}
- C08G 18/4854: {Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group}
- C08G 18/4858: {Polyethers containing oxyalkylene groups having more than four carbon atoms in the alkylene group}
- C08G 18/6208: {Hydrogenated polymers of conjugated dienes}
- C08G 18/6674: {with compounds of group C08G18/3203}
- C08G 18/6685: {with compounds of group C08G18/3225 or polyamines of C08G18/38}
- C08G 18/6688: {with compounds of group C08G18/3271}
- C08G 18/751: {containing only one cycloaliphatic ring}
- C08G 18/755: {and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate}
- C08G 18/758: {containing two or more cycloaliphatic rings}
- C08G 18/7621: {being toluene diisocyanate including isomer mixtures}
- C08G 18/765: {alpha, alpha, alpha', alpha', -tetraalkylxylylene diisocyanate or homologues substituted on the aromatic ring}
- C08G 18/7671: {containing only one alkylene bisphenyl group}
- A61L 2430/20: for reconstruction of the heart, e.g. heart valves
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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)

## Abstract

Partially crosslinked polyurethane polymers comprising diisocyanates and aliphatic hydrocarbon soft segments with a short-chain diol chain extender and a multifunctional amine and/or alcohol crosslinker to provide a polyurethane polymer with useful properties for the production of medical implant devices such as heart valves, are described. The polymers have an unexpected linear elastic region in a range from 5-100% and preferably between 10-35%. In some embodiments the polyurethanes are a thermally convertible gel formulation which may be converted to a liquid formulation by extended heating to render the polymer suitable for solvent processing techniques such as casting, spraying, spinning, etc. The invention also provides for living hinge polyurethane polymers which are thermally modifiable from a gel to a liquid and reaction injection moulded (RIM) polyurethanes with an enhanced flex life.

## Claims

### Claim 1

A medical implant device comprising a partially crosslinked polyurethane polymer made from reacting methylene diphenyl diisocyanate (MDI) and a hydrogenated polybutadiene diol (HPBD) soft segment having a functionality of 1.9 to 2.2 and a number average molecular weight of ˜1000-3000; said polymer comprising a chain extender, which is selected from one or more of a diamine, an alkanolamine, 1,4-butane diol (BDO), ethane diol (EDO), ethylene glycol, and hexane diol (HDO); said polymer further comprising a crosslinker; and said polymer having a linear elastic region in a range from 5 to 100%.

### Claim 2 (depends on 1)

A medical implant device as claimed in claim 1, wherein the chain extender comprises a diol selected from one or more of 1,4-butane diol (BDO), ethane diol (EDO), ethylene glycol, and hexane diol (HDO).

### Claim 3 (depends on 1)

A medical implant device as claimed in claim 1, wherein the crosslinker is selected from either or both of triethanolamine (TEOA) and trimethylol propane (TMP) in the range of 3 to 15% of the polymer (based on diisocyanate equivalents).

### Claim 4 (depends on 1)

The medical implant device as claimed in claim 1 wherein the chain extender comprises a diamine selected from the group consisting of hexamethylene diamine (HMDA), ethylene diamine (EDA), butane diamine (BDA), trimethyl hexamethylene diamine (TMDA), 4,4′-methylenebis(2-chloroaniline) (MOCA), dimeryl diamine and hydrogenated methylene dianiline (MDAH).

### Claim 5 (depends on 1)

A medical implant device as claimed in claim 1, wherein the chain extender comprises a diamine.

### Claim 6 (depends on 1)

The medical implant device as claimed in claim 1, wherein the chain extender comprises an alkanolamine selected from the group comprising ethanolamine, 3-amino-1-propanol, 4-amino-1-butanol and 4-amino-phenol.

### Claim 7 (depends on 6)

The medical implant device as claimed in claim 6 which is formed by a one or two-step process.

### Claim 8 (depends on 6)

The medical implant device as claimed in claim 6 which further includes a crosslinker selected from the group comprising a multifunctional amine and an alcohol crosslinker.

### Claim 9 (depends on 1)

A medical implant device as claimed in claim 1, having a thermally convertible gel formulation which is converted to a liquid formulation by extended heating to render the polymer suitable for solvent processing techniques.

### Claim 10 (depends on 9)

The medical implant device as claimed in claim 9, wherein the conversion of the gel to the liquid is achieved at a temperature range of 90-125° C.