Polyurethane/urea materials

Patent metadata

Field	Value
Publication number	US-11053342-B2
Application number	US-201615771719-A
Country	US
Kind code	B2
Filing date	Oct 28, 2016
Priority date	Oct 29, 2015
Publication date	Jul 6, 2021
Grant date	Jul 6, 2021

Abstract

The present disclosure provides soft block copolymer segments of Formula 1 for thermoplastic polyurethane or polyurethaneurea elastomer materials and their reaction products with divalent compounds, such as diisocyanates, chain extenders and optional additional polyols or polyamines. Also disclosed herein are methods for the production of the soft block copolymer segments, and possible applications of these materials in the formation of biomaterials for articles including medical devices such as implants, heart valves and drug delivery devices.

First claim

The invention claimed is:

1. A thermoplastic polyurethane or polyurethane urea elastomer material comprising a first plurality of soft segments, a second plurality of soft segments derived from a polyol, and a plurality of hard segments,
wherein
the first plurality of soft segments is derived from a macro-monomer having at least one copolymer segment of Formula 1;

wherein
A 1 is an endcapping group;
A 2 is hydrogen or an endcapping group;
each Y 1 and Y 2 independently comprises a group derived from a polyol or polyamine selected from a polysiloxane macrodiol, polysiloxane macrodiamine, polyether macrodiol, polycarbonate macrodiol, polyester macrodiol, or a polyhydrocarbon macrodiol;
each L 1 and L 2 is independently a divalent linking group;
each divalent linking group independently comprises a urethane or a urea;
n is an integer of 1 to 5;
t is 0 to 5; and
Q is represented by Formula A or Formula B:

wherein
R 1 , R 2 , R 3 , and R 4 are each independently selected from hydrogen and an optionally substituted straight chain, branched or cyclic, saturated or unsaturated hydrocarbon radical;
R 5 and R 6 are each independently selected from a straight chain, branched or cyclic, saturated or unsaturated hydrocarbon radical optionally interrupted with one or more heteroatoms independently selected from O, N and S;
m is an integer of 2 to 50;
X is a group selected from OC(O)O, C(O)O and O;
q is an integer of 1 to 50; and
r is an integer of 2 to 50;
and wherein the material has an ultimate tensile strength of at least about 20 MPa at about 23° C.

2. An article which is composed wholly or partly of the polyurethane or polyurethane urea elastomer material of claim 1 .

3. The article of claim 2 , wherein the article is selected from artificial leather, shoe soles, cable sheathing, varnishes, coatings, structural components for pumps or vehicles, mining ore screens, conveyor belts, laminating compounds, fibres, textiles, separation membranes, sealants, and adhesive components.

4. The article of claim 2 , wherein the article is a medical device.

5. The article of claim 4 , wherein the medical device is selected from an implant a cardiac pacemaker, defibrillator, catheter, heart valve, cardiac assist device, vascular graft and an implantable prosthesis, a cannula, extra-corporeal device, artificial organ, pacemaker lead, defibrillator lead, blood pump, balloon pump, A-V shunt, biosensor, membrane for cell encapsulation, drug delivery device, wound dressing, artificial joint, orthopaedic implant, and a soft tissue replacement.

6. The material of claim 1 , wherein the material has an ultimate tensile strength from about 25 MPa to about 50 MPa at about 23° C.

7. The material of claim 1 , wherein the material has an ultimate tensile strength from about 30 MPa to about 45 MPa at about 23° C.

8. The material of claim 1 , wherein the material has an ultimate tensile strength from about 30 MPa to about 40 MPa at about 23° C.

9. The material of claim 1 , wherein the material has an elongation at break of less than about 650% at about 23° C.

10. The material of claim 1 , wherein the material has an elongation at break of at least about 500% at about 23° C.

11. The material of claim 1 , wherein the material has an elongation at break from about 500% to about 1000% at about 23° C.

12. The material of claim 1 , wherein the material has an elongation at break from about 600% to about 700% at about 23° C.

13. The material of claim 1 , wherein the material has an elongation at break from about 600% to about 650% at about 23° C.

14. The material of claim 1 , wherein the material has:
(i) ultimate tensile strength from about 30 MPa to about 40 MPa at about 23° C.; and
(ii) elongation at break from about 600% to about 700% at about 23° C.

15. The material of claim 1 , wherein the material has a tear strength from about 62 N/mm to about 66 N/mm at about 23° C.

16. The material of claim 1 , wherein the material has a Young's modulus from about 15 MPa to about 30 MPa at about 23° C.

17. The material of claim 1 , wherein the material has a Young's modulus from about 15 MPa to about 25 MPa at about 23° C.

18. The material of claim 1 , wherein material is from about 20 wt % to about 60 wt % hard segment.

19. The material of claim 1 , wherein the polydispersity index of the material is ≤3.00.

20. The material of claim 1 , wherein the polydispersity index of the material is from 2.50 to 3.00.

21. The material of claim 1 , wherein the macro-monomer has at least one copolymer segment of Formula 1 having a molecular weight between about 400 g/mol and about 6000 g/mol.

22. The material of claim 1 , wherein the material has a number-average molecular weight of at least about 100,000 g/mol.

23. The material of claim 1 , wherein the material has a number-average molecular weight from about 100,000 g/mol to about 125,000 g/mol.

24. The material of claim 1 , wherein the material has a weight-average molecular weight of at least about 260,000 g/mol.

25. The material of claim 1 , wherein the material has a weight-average molecular weight from about 260,000 g/mol to about 355,000 g/mol.

Assignees

• Commw Scient Ind Res Org

Inventors

• Gunatillake Pathiraja Arachchillage
• Bown Mark
• Adhikari Raju

Classifications

• C08L2203/02

  for biomedical use · CPC title

• C08L83/12

  containing polyether sequences · CPC title

• C08G81/027

  containing polyester or polycarbonate sequences · CPC title

• C08G81/025

  containing polyether sequences · CPC title

• C08G77/46

  containing polyether sequences · CPC title