IP Library › Granted Patent US 11,608,408
Granted Patent B2
US 11,608,408 · App. 16/348,219 · Granted Mar 21, 2023

Polyurethane comprising graphene nano structure

Inventors: Michael Jae Lubitz (Waterford, MI); Andrew Schuster (Malcom, IA); Janine Luesing (Wyandotte, MI)
Assignee: BASF SE
C08G18/7671C08G18/10C08G18/12C08G18/1808C08G18/4018C08G18/4238C08G18/4277C08G18/48C08G18/4854C08G18/4887C08K3/042C08K5/0025C08K5/053C08K5/17C08K7/00C08L75/04C08K2201/005C08K2201/011C08L2207/04
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Quick Facts
Patent No.
US 11,608,408
App. No.
16/348,219
Granted
Mar 21, 2023
Kind
B2
Abstract

Described herein is a polyurethane including a reaction product of an isocyanate component, a polyol component, and graphene nano platelets. The graphene nano platelets are reacted in an amount of from about 0.1 to about 20% by weight, based on a total weight of the polyurethane. The graphene nano platelets have an average lateral dimension (x, y) of from about 1 to about 100 μm, an average through-plane dimension (z) of from about 5 to about 100 nm, and an oxygen content of from about 0.01 to about 10% by weight, based on a total weight of the graphene nano platelets.

Claims (60)

1. A polyurethane comprising a reaction product of:

an isocyanate component;

a polyol component;

an aromatic diol having from 8 to 24 carbon atoms; and

from about 0.1 to about 20% by weight, based on a total weight of the polyurethane, of graphene nano platelets, and an oxygen content of from about 0.01 to about 10% by weight based on a total weight of said graphene nano platelets.

2. A polyurethane as set forth in claim 1 wherein said graphene nano platelets have:

an oxygen content of from about 0.01 to about 5% by weight based on 100 percent by weight of the graphene nano platelets.

3. A polyurethane as set forth in claim 1 comprising about 0.1 to about 5% by weight of said graphene nano platelets based on the total weight of said polyurethane.

4. A polyurethane as set forth in claim 1 comprising:

an isocyanate prepolymer comprising the reaction product of said isocyanate component comprising an aromatic isocyanate, said polyol component, said aromatic diol having from 8 to 24 carbon atoms; and said graphene nano platelets; and

at least one of a polyol, a diol, or an amine.

5. A polyurethane as set forth in claim 1 wherein said polyol component comprises a polyether polyol.

6. A polyurethane as set forth in claim 1 wherein said polyol component comprises a polyester polyol.

7. A polyurethane as set forth in claim 1 wherein said polyol component comprises a polyol formed from tetrahydrofuran and/or caprolactone.

8. A polyurethane as set forth in claim 1 having a hard block content of from about 50 to about 95 molar %.

9. A polyurethane as set forth in claim 1 which is further defined as a polyurethane cast elastomer, a thermoplastic polyurethane elastomer, a polyurethane foam, or a polyurethane adhesive.

10. An isocyanate prepolymer having an isocyanate content of from about 4 to about 30% by weight, said prepolymer comprising a reaction product of:

an aromatic isocyanate;

a polyol;

an aromatic diol having from 8 to 24 carbon atoms; and

from about 0.1 to about 20% by weight, based on a total weight of the isocyanate prepolymer, of graphene nano platelets, and an oxygen content of from about 0.01 to about 10% by weight based on the total weight of said graphene nano platelets.

11. An isocyanate prepolymer as set forth in claim 10 wherein said graphene nano platelets have:

an oxygen content of from about 0.01 to about 5% by weight based on 100 percent by weight of the graphene nano platelets.

12. An isocyanate prepolymer as set forth in claim 10 comprising about 0.1 to about 5% by weight of said graphene nano platelets based on the total weight of said isocyanate prepolymer.

13. An isocyanate prepolymer as set forth in claim 10 having a weight average molecular weight (Mw) of from about 100 to about 5,000.

14. An isocyanate prepolymer as set forth in claim 10 having an isocyanate content from about 5 to about 20% by weight.

15. An isocyanate prepolymer as set forth in claim 10 wherein said polyol comprises a polyether polyol.

16. An isocyanate prepolymer as set forth in claim 10 wherein said polyol comprises a polyester polyol.

17. An isocyanate prepolymer as set forth in claim 10 wherein said aromatic isocyanate comprises methylene diphenyl diisocyanate and/or polymeric methylene diphenyl diisocyanate.

18. An isocyanate prepolymer as set forth in claim 10 wherein said polyol comprises a polyol formed from tetrahydrofuran and/or caprolactone.

19. An isocyanate prepolymer as set forth in claim 18 wherein said polyol formed from tetrahydrofuran and/or caprolactone is further defined as a block copolymer comprising polymerized polytetrahydrofuran and polycapralactone blocks.

20. A polyurethane elastomer comprising the reaction product of:

said isocyanate prepolymer as set forth in claim 18 ;

an aliphatic diol having from 2 to 12 carbon atoms and/or an amine; and

optionally one or more polyols;

wherein said polyurethane elastomer has a hard block content of from about 50 to about 95 molar % based on a total equivalent of said aliphatic diol and/or said amine divided by a total equivalent of NCO used to form said polyurethane elastomer.

21. A polyurethane elastomer comprising

said isocyanate prepolymer as set forth in claim 10 ;

wherein said polyurethane elastomer has a hard block content of from about 50 to about 95 molar % based on a total equivalent of said aromatic diol divided by a total equivalent of NCO used to form said polyurethane elastomer.

22. A thermoplastic polyurethane elastomer formed with the isocyanate prepolymer as set forth in claim 10 .

23. A method of forming an isocyanate prepolymer having a weight average molecular weight (Mw) of from about 100 to about 5,000 g/mol, said method comprising the step of reacting:

an aromatic isocyanate;

a polyol;

an aromatic diol having from 8 to 24 carbon atoms; and

from about 0.1 to about 20% by weight, based on a total weight of the isocyanate prepolymer, of graphene nano platelets, and an oxygen content of from about 0.01 to about 10% by weight based on a total weight of said graphene nano platelets.

24. A method as set forth in claim 23 wherein the step of reacting is substantially free of solvent.

25. A method as set forth in claim 23 wherein the aromatic isocyanate comprises methylene diphenyl diisocyanate and/or the polyol is selected from the group consisting of polyether polyols, polyester polyols, natural oil polyols, polydiene polyols, and combinations thereof.

26. A method as set forth in claim 23 wherein the graphene nano platelets have:

an oxygen content of from about 0.7 to about 5% by weight based on 100 percent by weight of the graphene nano platelets.

27. A method as set forth in claim 23 wherein the isocyanate prepolymer comprises about 0.1 to about 5% by weight of the graphene nano platelets, based on the total weight of the isocyanate prepolymer.

28. A method as set forth in claim 23 wherein the step of reacting the aromatic isocyanate, the polyol, and the graphene nano platelets includes the steps of:

adding the isocyanate into a reaction vessel;

mixing the polyol and the graphene nano platelets to form an isocyanate reactive mixture; and

incrementally adding the isocyanate reactive mixture to the reaction vessel.

29. A method as set forth in claim 23 further comprising the step of forming a cast elastomer by:

heating the isocyanate prepolymer to a temperature of 20 to 150° C.; and

combining the isocyanate prepolymer with an aliphatic diol having from 2 to 12 carbon atoms.

30. A method as set forth in claim 29 wherein the step of heating is further defined as heating the isocyanate prepolymer to a temperature of 50 to 130° C.

31. A method as set forth in claim 30 further comprising the step of post curing the cast elastomer at a temperature of from about 100 to about 200° C.

32. A method as set forth in claim 23 which is substantially free of solvent.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 6, 2023
From: LUESING, JANINE; LUBITZ, MICHAEL JAE; SCHUSTER, ANDREW
To: BASF CORPORATION
Reel/Frame 062891/0726 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 6, 2023
From: BASF CORPORATION
To: BASF SE
Reel/Frame 062891/0785 →
Continuity (2)
Provisional Application 62419753 · Nov 9, 2016
Related Publication 20190322789A1 · Oct 24, 2019