Recovery and reuse of acid digested amine/epoxy-based composite matrices

Patent metadata

Field	Value
Publication number	US-12460063-B2
Application number	US-202017761856-A
Country	US
Kind code	B2
Filing date	Sep 18, 2020
Priority date	Sep 18, 2019
Publication date	Nov 4, 2025
Grant date	Nov 4, 2025

Abstract

A method for recycling matrix residues includes steps of degrading a target epoxy to form matrix residues, collecting the matrix residues, and adding the matrix residues into a polymer-forming formulation. Characteristically, the polymer-forming formulation includes multifunctional anhydride monomers and polyfunctional co-reactant monomers.

First claim

What is claimed is:

1 . A method for recycling matrix residues, the method comprising:
degrading a target epoxy to form matrix residue materials; collecting the matrix residue materials; and adding the matrix residue materials into a polymer-forming formulation, the polymer-forming formulation including multifunctional anhydride monomers and polyfunctional co-reactant monomers, wherein the matrix residues are a filler for the polymer-forming formulation.

2 . The method of claim 1 wherein the target epoxy is an amine-cured epoxy.

3 . The method of claim 1 wherein the polymer-forming formulation is an anhydride-based formulation.

4 . The method of claim 1 wherein the target epoxy is contacted with an acidic solution for a predetermined time period to form a reacted mixture.

5 . The method of claim 4 wherein the acidic solution includes hydrogen peroxide and acetic acid.

6 . The method of claim 5 wherein the reacted mixture is neutralized.

7 . The method of claim 6 wherein viscous liquids and/or solid powder residues are precipitated from the reacted mixture.

8 . The method of claim 5 wherein matrix residues are obtained from the reacted mixture by evaporation of the acetic acid.

9 . The method of claim 4 wherein the acidic solution contains acetic acid and is exposed to oxygen.

10 . The method of claim 9 wherein the reacted mixture is neutralized.

11 . The method of claim 9 wherein matrix residues are obtained from the reacted mixture by evaporation of the acetic acid.

12 . The method of claim 1 wherein the target epoxy is contacted with a neutral solution for a predetermined time period to form a reacted mixture.

13 . The method of claim 12 wherein the neutral solution includes benzyl alcohol.

14 . The method of claim 1 wherein the matrix residues are an activator for the polymer-forming formulation of a thermoset resin system, the matrix residues including amine or hydrazine functional groups.

15 . The method of claim 14 wherein the thermoset resin system is an anhydride-based formulation.

16 . The method of claim 14 wherein the matrix residues are present in an amount of about 1 to 20 weight percent of the polymer-forming formulation.

17 . The method of claim 14 wherein the target epoxy is formed from a multifunctional amine-containing epoxide monomer.

18 . The method of claim 17 wherein the multifunctional amine-containing epoxide monomer is selected from the group consisting of triglycidyl-p-aminophenol, tetraglycidyl-4,4′-diaminodiphenylmethane, and combinations thereof.

19 . The method of claim 14 wherein the matrix residues include reside of multifunctional amine-containing epoxide monomers or hydrazine functionalized derivatives thereof.

20 . A method for recycling matrix residues, the method comprising:
degrading a target epoxy to form matrix residue materials; collecting the matrix residue materials; adding the matrix residue materials into a polymer-forming formulation, the polymer-forming formulation including multifunctional anhydride monomers and polyfunctional co-reactant monomers; and contacting the target epoxy with an acidic solution for a predetermined time period to form a reacted mixture, wherein the acidic solution includes acetic acid and is exposed to oxygen.

21 . The method of claim 20 , wherein the target epoxy is an amine-cured epoxy.

22 . The method of claim 20 , wherein the polymer-forming formulation is an anhydride-based formulation.

23 . The method of claim 20 , wherein the matrix residues are an activator for the polymer-forming formulation of a thermoset resin system, the matrix residues including amine or hydrazine functional groups.

24 . The method of claim 23 , wherein the target epoxy is formed from a multifunctional amine-containing epoxide monomer.

25 . The method of claim 24 , wherein the multifunctional amine-containing epoxide monomer is selected from the group consisting of triglycidyl-p-aminophenol, tetraglycidyl-4,4′-diaminodiphenylmethane, and combinations thereof.

26 . A method for recycling matrix residues, the method comprising:
degrading a target epoxy to form matrix residue materials; collecting the matrix residue materials; adding the matrix residue materials into a polymer-forming formulation, the polymer-forming formulation including multifunctional anhydride monomers and polyfunctional co-reactant monomers; and contacting the target epoxy with an acidic solution for a predetermined time period to form a reacted mixture, wherein the acidic solution includes hydrogen peroxide and acetic acid and wherein matrix residues are obtained from the reacted mixture by evaporation of the acetic acid.

27 . The method of claim 26 , wherein the target epoxy is an amine-cured epoxy.

28 . The method of claim 26 , wherein the polymer-forming formulation is an anhydride-based formulation.

29 . The method of claim 26 , wherein the matrix residues are an activator for the polymer-forming formulation of a thermoset resin system, the matrix residues including amine or hydrazine functional groups.

30 . The method of claim 29 , wherein the target epoxy is formed from a multifunctional amine-containing epoxide monomer.

31 . The method of claim 30 , wherein the multifunctional amine-containing epoxide monomer is selected from the group consisting of triglycidyl-p-aminophenol, tetraglycidyl-4,4′-diaminodiphenylmethane, and combinations thereof.

Assignees

• Univ Southern California

Inventors

• Williams Travis J
• Nutt Steven
• Ma Yijia
• Navarro Carlos

Classifications

• C08J2363/00

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

• C08J11/16

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

• C08G59/50

  Amines · CPC title

• C08G59/4035

  Hydrazines; Hydrazides · CPC title

• C08G59/20

  characterised by the epoxy compounds used · CPC title