Plastic waste-derived polymers and resins and methods of making the same

Patent metadata

Field	Value
Publication number	US-12030969-B2
Application number	US-202117371421-A
Country	US
Kind code	B2
Filing date	Jul 9, 2021
Priority date	Jul 13, 2020
Publication date	Jul 9, 2024
Grant date	Jul 9, 2024

Abstract

The present disclosure relates to a resin that includes a first repeat unit as defined by Structure (I)

where A is either a methyl group or a hydrogen atom, R 1 is a first bridging group, and is a covalent bond.

First claim

The invention claimed is:

1. A resin comprising:
a first repeat unit as defined by Structure (I),

wherein:
A is selected from the group consisting of a methyl group and a hydrogen atom,
R 1 comprises a first bridging group,
and
is a covalent bond.

2. The resin of claim 1 , wherein:
R 1 comprises at least one of

and
R 2 comprises a second bridging group.

3. The resin of claim 2 , wherein:
R 2 comprises at least one of

4. The resin of claim 2 , wherein:
R 1 is

5. The resin of claim 1 , further comprising a second repeat unit as defined by Structure (II),

6. The resin of claim 1 , comprising a tensile strength between about 20 MPa and about 100 MPa.

7. The resin of claim 1 , comprising a modulus between about 0.5 GPa and about 3.0 GPa.

8. The resin of claim 1 , comprising an elongation at break between about 0.1% and about 100%.

9. The resin of claim 1 , comprising a glass transition temperature between about 0° C. and about 250° C.

10. A method comprising:
reacting a first functionalized intermediate with a second functionalized intermediate to form a resin, wherein:
the first functionalized intermediate comprises

the second functionalized intermediate comprises

the resin comprises a first repeat unit as defined by Structure (I),

the resin further comprises a second repeat unit as defined by Structure (II),

A is selected from the group consisting of a methyl group and a hydrogen atom,
R 1 comprises a first bridging group,
is a covalent bond.

11. The method of claim 10 , further comprising:
prior to the reacting, in a first mixture comprising a deconstruction product and a reactant comprising an acrylate group or a methacrylate group, functionalizing the deconstruction product, wherein:
the deconstruction product comprises

and
the functionalizing produces the first functionalized intermediate and the second functionalized intermediate.

12. The method of claim 10 , wherein:
the reacting is performed using a second mixture of the first functionalized intermediate and the second functionalized intermediate, and
the first functionalized intermediate and the second functionalized intermediate are at a molar ratio between about 1:2 and about 1:1.

13. The method of claim 12 , wherein the second mixture has a viscosity between about 800 cP and 1200 cP at when measured at a temperature of about 25° C.

14. The method of claim 10 , wherein the reacting is performed at a temperature between 20° C. and 150° C.

15. The method of claim 10 , wherein the reacting is photoinitiated at a wavelength between 254 nm and 500 nm.

16. The method of claim 10 , wherein the reacting is photoinitiated using at least one of diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide (TPO), ethyl (2,4,6-trimethylbenzoyl) phenylphosphinate (TPO-L), or phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide (BAPO).

17. The method of claim 11 , further comprising:
prior to the functionalizing, deconstructing a plastic, wherein:
the deconstructing results in the forming of the deconstruction product.

18. The method of claim 17 , wherein the plastic comprises at least one of polyethylene terephthalate, glycol modified polyethylene terephthalate, polybutylene terephthalate, polytrimethylene terephthalate, polyethylene naphthalate, or polyethylene 2,5-furandicarboxylate.

Assignees

• Alliance Sustainable Energy

Inventors

• Wang Chen
• Beckham Gregg Tyler
• Rorrer Nicholas A

Classifications

• C08J11/14

  by treatment with steam or water · CPC title

• C08F236/14

  containing elements other than carbon and hydrogen · CPC title

• C08J2367/04

  Polyesters derived from hydroxy carboxylic acids, e.g. lactones (C08J2367/06 takes precedence) · CPC title

• C08L101/06

  containing oxygen atoms {(C08L101/025 takes precedence)} · CPC title

• C08F218/12

  with unsaturated alcohols containing three or more carbon atoms · CPC title