IP Library Granted Patent US 9,815,808
Granted Patent B2
US 9,815,808 · App. 15/442,829 · Granted Nov 14, 2017

Recovery of monomer from polyurethane materials by depolymerization

Inventors: Marc Andrew Hillmyer (Minneapolis, MN); Tessie Rose Panthani (Minneapolis, MN); Marie Elizabeth Vanderlaan (Minneapolis, MN); Deborah Kay Schneiderman (Minneapolis, MN); Alexander Michael Rauch Mannion (Minneapolis, MN); Derek Charles Batiste (Minneapolis, MN); Christopher Ward Macosko (Minneapolis, MN); Jay Z. Wang (Kildeer, IL); Frank S. Bates (Minneapolis, MN)
Assignee: REGENTS OF THE UNIVERSITY OF MINNESOTA
C07D309/30C08G81/027
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Quick Facts
Patent No.
US 9,815,808
App. No.
15/442,829
Granted
Nov 14, 2017
Kind
B2
Abstract

Methods for recovering monomers from polymers, such as polyurethanes (including thermoset polyurethanes) include heating the polymer to depolymerize the polymer and release the monomer. The monomer may be directly recovered. The polymer may include a poly(β-methyl-δ-valerolactone) (PMVL) block and the monomer recovered may be β-methyl-δ-valerolactone (MVL).

Claims (17)

1. A method for recovering β-methyl-δ-valerolactone (MVL) from a polyurethane polymer comprising poly(β-methyl-δ-valerolactone) (PMVL) block, the method comprising:

heating the polymer to cause depolymerization and release of the MVL from the PMVL block; and

recovering the released MVL.

2. A method according to claim 1 , wherein the polyurethane polymer is a thermoset polyurethane foam.

3. A method according to claim 1 , wherein recovering the MVL comprises recovering the MVL via distillation.

4. A method according to claim 1 , wherein heating the polymer causes release of 50% or more of the MVL, and wherein recovering the released MVL comprises recovering the MVL at a purity of 90% or greater.

5. A method according to claim 1 , wherein heating the polymer comprises heating the polymer in the absence of a polymerization catalyst.

6. A method according to claim 1 , wherein heating the polyurethane polymer comprises heating the polymer in the presence of a polymerization catalyst.

7. A method according to claim 5 , wherein the polymerization catalyst is a ring opening transesterification catalyst.

8. A method according to claim 1 , wherein heating the polyurethane polymer comprises heating the polymer at a temperature in a range from 150° C. to 300° C.

9. A method according to claim 1 , wherein heating the polyurethane polymer comprises heating the polymer at a temperature in a range from 180° C. to 240° C.

10. A method according to claim 1 , wherein at least a portion of the PMVL in the polyurethane polymer comprises a PMVL block having a number average molar mass (M n ) of 0.25 kg/mol or greater.

11. A method according to claim 1 , wherein the PMVL has a 14 C/ 12 C ratio greater than zero.

12. A method for recovering β-methyl-δ-valerolactone (MVL) from a polymer comprising poly(β-methyl-δ-valerolactone) (PMVL), the method comprising:

heating the polymer to cause depolymerization and release of the MVL from the PMVL; and

recovering the released MVL.

13. A method according to claim 12 , wherein the PMVL polymer is a block copolymer comprising a PMVL block.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 6, 2017
From: BATES, FRANK S.; MACOSKO, CHRISTOPHER WARD; PANTHANI, TESSIE ROSE; VANDERLAAN, MARIE ELIZABETH; WANG, JAY Z.; MANNION, ALEXANDER MICHAEL RAUCH
To: REGENTS OF THE UNIVERSITY OF MINNESOTA
Reel/Frame 043807/0247 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 10, 2017
From: HILLMYER, MARC ANDREW
To: REGENTS OF THE UNIVERSITY OF MINNESOTA
Reel/Frame 042318/0774 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 28, 2017
From: SCHNEIDERMAN, DEBORAH KAY; BATISTE, DEREK CHARLES
To: REGENTS OF THE UNIVERSITY OF MINNESOTA
Reel/Frame 042177/0832 →
CONFIRMATORY LICENSE Recorded Mar 29, 2017
From: UNIVERSITY OF MINNESOTA
To: NATIONAL SCIENCE FOUNDATION
Reel/Frame 042109/0959 →
Continuity (2)
Provisional Application 62301126 · Feb 29, 2016
Related Publication 20170247350A1 · Aug 31, 2017