Biobased materials derived from cyclic monoterpenes

Patent metadata

Field	Value
Publication number	US-12304978-B2
Application number	US-202217805708-A
Country	US
Kind code	B2
Filing date	Jun 7, 2022
Priority date	Jun 7, 2022
Publication date	May 20, 2025
Grant date	May 20, 2025

Abstract

A process, a composition, and an article of manufacture are disclosed. The process includes generating a cyclic monoterpene derivative. The generating includes oxidizing a cyclic monoterpene to generate a ketone derivative and oxidizing the ketone derivative to form a lactone derivative. The composition and the article of manufacture include a polymer having monomer repeat units derived from a lactone derivative of a cyclic monoterpene.

First claim

What is claimed is:

1. A process, comprising:
generating a cyclic monoterpene derivative, the generating comprising:
oxidizing a cyclic monoterpene to generate a ketone derivative;
oxidizing the ketone derivative to form a lactone derivative; and
epoxidizing the lactone derivative; and

reacting the epoxidized lactone derivative to form a polycarbonate.

2. The process of claim 1 , wherein the cyclic monoterpene is an endocyclic alkene.

3. The process of claim 2 , wherein the oxidizing the cyclic monoterpene comprises reacting the cyclic monoterpene with potassium permanganate (KMnO 4 ).

4. The process of claim 1 , wherein the cyclic monoterpene is an exocyclic alkene.

5. The process of claim 4 , wherein the oxidizing the cyclic monoterpene comprises reacting the cyclic monoterpene with selenium dioxide (SeO 2 ).

6. A composition, comprising:
a polycarbonate comprising monomer repeat units derived from a derivative of a cyclic monoterpene, the derivative generated in a process comprising:
oxidizing a cyclic monoterpene to generate a ketone derivative;
oxidizing the ketone derivative to form a lactone derivative; and
epoxidizing the lactone derivative.

7. The composition of claim 6 , wherein a plurality of the monomer repeat units have at least one sidechain functional group.

8. The composition of claim 6 , wherein each of the monomer repeat units has two reactive sites.

9. The composition of claim 6 , wherein the cyclic monoterpene is an endocyclic alkene.

10. The composition of claim 9 , wherein the oxidizing the cyclic monoterpene comprises reacting the cyclic monoterpene with potassium permanganate (KMnO 4 ).

11. The composition of claim 6 , wherein the cyclic monoterpene is an exocyclic alkene.

12. The composition of claim 11 , wherein the oxidizing the cyclic monoterpene comprises reacting the cyclic monoterpene with selenium dioxide (SeO 2 ).

13. An article of manufacture, comprising:
a polycarbonate comprising monomer repeat units derived from a derivative of a cyclic monoterpene, the derivative generated in a process comprising:
oxidizing a cyclic monoterpene to generate a ketone derivative;
oxidizing the ketone derivative to form a lactone derivative; and
epoxidizing the lactone derivative.

14. The article of manufacture of claim 13 , wherein a plurality of the monomer repeat units have at least one sidechain functional group.

15. The article of manufacture of claim 13 , wherein each of the monomer repeat units has two reactive sites.

16. The process of claim 1 , wherein the reacting the epoxidized lactone derivative to form the polycarbonate comprises a ring-opening copolymerization of the epoxidized lactone derivative with carbon dioxide.

17. The process of claim 1 , further comprising generating acrylate reactive groups on the polycarbonate.

18. The process of claim 17 , further comprising forming sidechains at the acrylate reactive groups.

19. The composition of claim 9 , wherein the oxidizing the cyclic monoterpene comprises reacting the cyclic monoterpene with chromium trioxide (CrO 3 ).

20. The composition of claim 9 , wherein the oxidizing the cyclic monoterpene comprises reacting the cyclic monoterpene with dichlorotetrakis(pyridine) cobalt and oxygen.

Assignees

• IBM

Inventors

• Kobilka Brandon M
• Wertz Jason T
• Czaplewski-Campbell Sarah K
• Campbell Eric J

Classifications

• C07C49/543

  to a six-membered ring · CPC title

• C01G45/1214

  containing alkali metals · CPC title

• C01B19/004

  Oxides; Hydroxides · CPC title

• C07C13/00

  Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings · CPC title

• C07B33/00

  Oxidation in general · CPC title