Methods for chemical degradation of epoxies using organic salts as catalysts

Patent metadata

Field	Value
Publication number	US-10696815-B2
Application number	US-201816004169-A
Country	US
Kind code	B2
Filing date	Jun 8, 2018
Priority date	Jun 9, 2017
Publication date	Jun 30, 2020
Grant date	Jun 30, 2020

Abstract

The subject matter disclosed herein is generally directed to methods of recycling epoxy polymers using organic salts as catalysts in an aqueous solution. Epoxy polymers and their composites are widely used in many fields such as coatings, adhesives, wind blades, automobiles, aeronautic vehicles, and sporting goods. However, the management of thermoset composite wastes is becoming a public concern as the out of service thermoset products build up. With the increasing awareness of environmental protection and the depleting of landfill sites, it is of great importance to develop an economically viable and environmentally-friendly recycling technology of thermoset materials that is suitable to industrial scale-up production. As such, there is a clear and present need for a novel solution that is environmentally friendly and scalable in the market.

First claim

What is claimed is:

1. A method for degradation of epoxy polymers in a chemical reaction comprising cleaving chemical bonds in a polymer using a solvent comprising one or more organic salts as a catalyst in an aqueous solution.

2. The method of claim 1 , wherein the polymer comprises a pure epoxy polymer.

3. The method of claim 1 , wherein the polymer comprises a fiber reinforced epoxy.

4. The method of claim 3 , wherein the fiber reinforced epoxy comprises glass or carbon fibers.

5. The method of claim 1 , wherein the polymer is a coating or adhesive.

6. The method of claim 1 , further comprising reducing the polymer to particles or fragments before cleaving chemical bonds, such as by chopping, slicing, shredding, crushing, pulverizing, or any combination thereof.

7. The method of claim 1 , further comprising heating the reaction to a reaction temperature above the glass transition (T g ) temperature of the polymer and below the temperature wherein the polymer burns, wherein swelling of the polymer with the solvent takes place.

8. The method of claim 7 , wherein the reaction temperature is about 100 to 270° C.

9. The method of claim 7 , wherein the reaction temperature is about 150 to 250° C.

10. The method of claim 1 , wherein the reaction time is about 1 to 15 hours.

11. The method of claim 1 , wherein the reaction time is about 3 to 6 hours.

12. The method of claim 1 , wherein the organic salt comprises an anion and cation,
wherein the cation is selected from the group consisting of Zn 2+ , Fe 3+ , Fe 2+ , Cu 2+ , Cu + , Cr 3+ , Cr 2+ , Mn 2+ , Mn 3+ , Ni 3+ , Sn 2+ , Sn 4+ , Pb 2+ , and Pb 4+ ions, and
wherein the anion is selected from the group consisting of acetate (CH 3 COO—), formate (HCOO—), propionate (C 2 H 5 COO—), octoate, ethanedioate ([C 2 O 4 ] 2− ), and organic sulphonic acid ions.

13. The method of claim 1 , wherein the polymer comprises amine-cured epoxies or anhydride-cured epoxies.

14. The method of claim 1 , wherein the weight fraction of catalyst in the aqueous solution of the solvent is about 3 to 30 wt %.

15. The method of claim 1 , wherein the weight fraction of polymer in the solvent is about 5 to 80 wt %.

16. The method of claim 1 , further comprising recovering decomposed matrix polymer (DMP) from the reaction.

17. The method of claim 3 , further comprising recovering decomposed matrix polymer (DMP) and fiber from the reaction.

18. The method of claim 16 , further comprising using the recovered DMP as a curing agent in the preparation of cured epoxy or in the preparation of polyurethane.

19. The method of claim 17 , further comprising using the recovered DMP as a curing agent in the preparation of cured epoxy or in the preparation of polyurethane.

20. The method of claim 1 , wherein the reaction pressure is about 0.5 to 4 MPa.

Assignees

• Univ Washington State

Inventors

• Zhang Jinwen
• Liu Tuan
• Xin Junna

Classifications

• C08J11/16 Primary

  by treatment with inorganic material (C08J11/14 takes precedence) · CPC title

• Y02W30/62

  Plastics recycling; Rubber recycling · CPC title

• C08J2363/00

  Characterised by the use of epoxy resins; Derivatives of epoxy resins · CPC title

• C08J11/28

  by treatment with organic compounds containing nitrogen, sulfur or phosphorus · CPC title

• C08J11/26 Primary

  containing carboxylic acid groups, their anhydrides or esters · CPC title