Granted Patent
B2
US 12,325,778 · App. 17/605,831 · Granted Jun 10, 2025
Urethane exchange catalysts and methods for reprocessing cross-linked polyurethane foams
Inventors:
David J. Fortman (Pittsburgh, PA); William R. Dichtel (Wilmette, IL); Daylan T. Sheppard (Evanston, IL); Kailong Jin (Minneapolis, MN); Christopher J. Ellison (Eden Prairie, MN)
C08J11/26B01J31/04B01J31/2234C08G18/12C08G18/14C08G18/242C08G18/42C08G18/4812C08G18/4833C08G18/7671B01J2531/54B01J2531/842C08G2110/0025C08J2375/06C08J2375/08
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Abstract
Disclosed herein are methods for reprocessing polyurethane compositions such as polyurethane foams. The method comprises introducing a polyurethane composition into a compounding device, heating the polyurethane composition to an effective bond-exchange temperature, and compounding the polyurethane composition for an effective bond-exchange time.
Claims (20)
1. A method for reprocessing a polyurethane composition, the method comprising introducing a polyurethane composition into a compounding device, heating the polyurethane composition to an effective bond-exchange temperature, and compounding the polyurethane composition for an effective bond-exchange time, wherein the polyurethane composition comprises a network polymer and an effective amount of a polyurethane exchange catalyst permeated within the network polymer, wherein the network polymer comprises a dynamic network formed from an isocyanate constitutional unit and a second constitutional unit having a hydroxyl group capable of reacting with an isocyanate group of the isocyanate constitutional unit to form a urethane bond.
2. A method of claim 1 , wherein the polyurethane composition is prepared from a polyurethane foam.
3. The method of claim 2 , further comprising providing the polyurethane composition by impregnating the polyurethane foam with the catalyst by swelling.
4. The method of claim 2 , further comprising providing the polyurethane composition by mixing the polyurethane foam with the catalyst.
5. The method of claim 2 , wherein the network polymer is formed in the presence of the catalyst.
6. The method of claim 1 , wherein the polyurethane exchange catalyst comprises a metal selected from Sn, Bi, Fe, Zr, Ti, Hf, Al, Zn, Cu, Ni, Co, Mn, V, Sc, Y, Ce, or Mo and a ligand coordinated with the metal atom.
7. The method of claim 6 , wherein the catalyst comprises DBTDL, Bi(neo) 3 , Fe(acac) 3 , Ti(OiPr) 2 (acac) 2 , Hf(acac) 4 , Zr(acac) 4 , Mn(acac) 2 , Bi(oct) 3 , Zn(tmhd) 2 , Zr(tmhd) 4 , or any combination thereof.
8. The method of claim 1 , wherein the effective amount of polyurethane exchange catalyst to total isocyanate functionality is less or equal to 5 mol %.
9. The method of claim 1 , wherein the second constitutional unit is a prepolymer molecule comprising a polyether, a polyester, a polycarbonate, a polyacrylate, a polyolefin, a polybutadiene, a polysulfide, or a polysiloxane.
10. The method of claim 1 , wherein the second constitutional unit is a branch unit having at least two hydroxyl groups each capable of reacting with the isocyanate group of the first constitutional unit to form the urethane bond.
11. The method of claim 10 , wherein the second constitutional unit further comprises one or more molecules selected from a polyether, a polyester, a polycarbonate, a polyacrylate, a polyolefin, a polybutadiene, a polysulfide, a polysiloxane, a plant-based oil, an alcohol, or an amine.
12. The method of claim 1 , wherein the isocyanate constitutional unit is an aromatic isocyanate constitutional unit.
13. The method of claim 1 , wherein the isocyanate constitutional unit comprises at least two isocyanate groups.
14. The method of claim 1 , wherein the effective bond-exchange temperature is less than or equal to 160° C.
15. The method of claim 1 , wherein the effective bond-exchange time is less than or equal to 12 minutes.
16. The method of claim 1 further comprising mechanically processing the polyurethane composition prior to heating.
17. The method of claim 1 , wherein the compounding device is a batch-service compounding device.
18. The method of claim 17 , wherein the compounding device is a mixer or a kneader.
19. The method of claim 1 , wherein the compounding device is a continuous-service compounding device.
20. The method of claim 19 , wherein the compounding device is a twin-screw extruder.
Assignments (3)
CONFIRMATORY LICENSE
Recorded Jan 30, 2025
From: NORTHWESTERN UNIVERSITY
To: NATIONAL SCIENCE FOUNDATION
Reel/Frame 070058/0133 →
ASSIGNMENT OF ASSIGNOR'S INTEREST
Recorded Oct 23, 2021
From: FORTMAN, DAVID J.
To: NORTHWESTERN UNIVERSITY; CORNELL UNIVERSITY
Reel/Frame 057887/0646 →
ASSIGNMENT OF ASSIGNOR'S INTEREST
Recorded Oct 23, 2021
From: DICHTEL, WILLIAM R.; SHEPPARD, DAYLAN T.
To: NORTHWESTERN UNIVERSITY
Reel/Frame 057887/0651 →
Continuity (2)
Provisional Application
62837606
· Apr 23, 2019
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