Method of forming of a robust network of epoxy material through Diels-Alder reaction

Patent metadata

Field	Value
Publication number	US-10647810-B2
Application number	US-201615751807-A
Country	US
Kind code	B2
Filing date	Aug 9, 2016
Priority date	Aug 11, 2015
Publication date	May 12, 2020
Grant date	May 12, 2020

Abstract

Thermally reworkable epoxy resins prepared through a Diels-Alder reaction are described herein. A maleimide component is reacted with an electron donating component having a furan ring attached to an epoxy ether to produce the epoxy resins. The epoxy component generated by this method can be cured with different diamines lo form a robust network of epoxy material. The robust epoxy material is used as a reversible thermoset and as an adhesive. The robust epoxy network is heated at 90° C. temperature in a retro Diels-Alder fashion to produce colorless starting materials of the maleimide component and the furan component.

First claim

What is claimed is:

1. A method of making a thermally reworkable epoxy material, the method comprising:
a) forming a first product by reacting a maleimide component with an electron donating component, wherein the maleimide component comprises:

wherein: R 1 =tetramethyl (bis-propyl)-disiloxane, or carbamate;
R′=hydrogen or methyl,
R″=hydrogen or methyl,
R′″=hydrogen or methyl, and
R″″=hydrogen or methyl, and

b) curing the first product with an amine component to form a final product, wherein the final product is a thermally reworkable epoxy material.

2. A method of making a thermally reworkable epoxy material, the method comprising:
a) forming a first product by reacting a maleimide component with an electron donating component, wherein the maleimide component comprises:

wherein: R 1 =tetramethyl (bis-propyl)-disiloxane,
R′=hydrogen or methyl,
R″=hydrogen or methyl,
R′″=hydrogen or methyl, and
R″″=hydrogen or methyl, and

b) curing the first product with an amine component to form a final product, wherein the final product is a thermally reworkable epoxy material.

3. The method of claim 2 , wherein the electron donating component comprises a furan component.

4. The method of claim 2 , wherein the electron donating component comprises a furan component having the structure:

wherein R 2 is an epoxy ether.

5. The method of claim 4 , wherein R 2 of the furan component comprises the structure:

wherein an epoxide end of R 2 functions as an electron receiving group.

6. The method of claim 2 , wherein the first product comprises the structure:

wherein: R 1 =tetramethyl (bis-propyl)-disiloxane,
R′=hydrogen or methyl,
R″=hydrogen or methyl,
R′″=hydrogen or methyl, and
R″″=hydrogen or methyl.

7. The method of claim 2 , wherein the amine component comprises a diamine having one or more of the following structures:

wherein: n=1-50, 10-50, 20-30, 20-50; 35-50 or 40-50.

8. The method of claim 7 , wherein the diamine component functions as a curing agent.

9. The method of claim 2 , wherein the first product is formed at a temperature range of about 90° C. to 110° C.

10. The method of claim 2 , wherein the first product is formed between about 20 minutes to 40 minutes after mixing of the maleimide component and the electron donating component, wherein the maleimide component reacts with the electron donating component to form the first product.

11. The method of claim 2 , Wherein the first product is formed without the presence of a solvent.

12. The method of claim 2 , wherein the first product formed is a colorless liquid.

13. The method of claim 2 , wherein first product formed with a range of yield of about 90% to 99%.

14. The method of claim 2 , wherein the first product is care with the amine at a temperature range of about 20° C. to 25° C.

15. The method of claim 2 , wherein the thermally reworkable epoxy material is an adhesive.

16. The method of claim 15 , wherein the adhesive has an E-modulus of about 205.213 MPa at a concentration of 0.0294 (g) of the thermally reworkable epoxy material after curing for about 5 days at a temperature range of about 20° C. to 30° C.

17. The method of claim 15 , wherein the adhesive has an E-modulus of about 200.646 M Pa at a concentration of 0.0294 (g) of the thermally reworkable epoxy material after curing at a temperature of about 100° C. after reclamping in an oven.

18. The method of claim 15 , wherein the adhesive has an E-modulus of about 251.535 at a concentration of 0.0294 (g) of the thermally reworkable epoxy material after curing at a temperature of about 110° C. after reclamping in an oven.

19. The method of claim 2 , wherein the thermally reworkable epoxy material was heated to produce the original maleimide component and the electron donating component through a retro Diels-Alder reaction.

20. The method of claim 19 , wherein the retro Diels-Alder reaction was performed at a temperature range of about 90° C. to 115° C.

Assignees

• Univ Arizona

Inventors

• Loy Douglas A
• Mcfadden Peter
• Bagge Robb E

Classifications

• C08G59/26

  heterocyclic · CPC title

• C08G59/504

  containing an atom other than nitrogen belonging to the amine group, carbon and hydrogen · CPC title

• C09J163/00

  Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins · CPC title

• C08G59/24

  carbocyclic · CPC title

• C08G59/306 Primary

  containing silicon · CPC title