Electrically conducting polyamides

Patent metadata

Field	Value
Publication number	US-12152106-B2
Application number	US-202117347050-A
Country	US
Kind code	B2
Filing date	Jun 14, 2021
Priority date	Jun 15, 2020
Publication date	Nov 26, 2024
Grant date	Nov 26, 2024

Abstract

A new, thermally stable conducting material, poly(3-amino-1H-pyrazole-4-carboxylate), can be used in a variety of applications such as thermoelectrics, electron acceptors in light-harvesting (photovoltaic) materials, and thermally stable conducting energetic materials. Related compounds include poly 3-amino-5-chloro-1H-pyrazole-4-carboxylate, poly 3-amino-5-bromo-1H-pyrazole-4-carboxylate, poly 3-amino-5-fluoro-1H-pyrazole-4-carboxylate, poly 3-amino-5-iodo-1H-pyrazole-4-carboxylate, poly 3, 5-diamino-1H-pyrazole-4-carboxylate, poly 3-amino-5-NHR 1 -1H-pyrazole-4-carboxylate, poly 3-amino-5-NR 2 -1H-pyrazole-4-carboxylate, or poly 3-amino-5-hydroxy-1H-pyrazole-4-carboxylate.

First claim

The invention claimed is:

1. A material comprising poly(3-amino-1H-pyrazole-4-carboxylate).

2. The material of claim 1 , wherein the poly(3-amino-1H-pyrazole-4-carboxylate) has from 2 to 20 repeat units.

3. A method of preparing poly(3-amino-1H-pyrazole-4-carboxylate) comprising:
reacting 3-amino-1H-pyrazole-4-carboxylate with an aqueous solution of R1 hydroxide; then
adding R2 persulfate; and then
allowing a reaction to form a product comprising poly(3-amino-1H-pyrazole-4-carboxylate),
wherein R1 denotes one singly charged cation and R2 denotes either (a) two singly charged cations or (b) one doubly charged cation.

4. The method of claim 3 , wherein said R1 hydroxide is potassium hydroxide and said R2 persulfate is sodium persulfate.

5. The method of claim 3 , wherein said R1 hydroxide is potassium hydroxide and said R2 persulfate is copper persulfate.

6. The method of claim 3 , further comprising extraction of the product with a non-aqueous solvent.

7. The method of claim 6 , wherein the non-aqueous solvent is N-methyl pyrrolidone.

8. A material comprising a compound selected from the group consisting of poly(3-amino-1H-pyrazole-4-carboxylate), poly(3-amino-5-chloro-1H-pyrazole-4-carboxylate), poly(3-amino-5-bromo-1H-pyrazole-4-carboxylate), poly(3-amino-5-fluoro-1H-pyrazole-4-carboxylate), poly(3-amino-5-iodo-1H-pyrazole-4-carboxylate), poly(3,5-diamino-1H-pyrazole-4-carboxylate), poly(3-amino-5-NHR-1H-pyrazole-4-carboxylate), poly(3-amino-5-N(R) 2 -1H-pyrazole-4-carboxylate), poly(3-amino-5-hydroxy-1H-pyrazole-4-carboxylate), and poly(3-amino-5-OR-1H-pyrazole-4-carboxylate),
wherein R is an alkyl or aromatic group.

9. The material of claim 8 , wherein said compound comprises from 2 to 20 repeat units.

10. A method of preparing the material of claim 8 , comprising:
reacting a monomer with an aqueous solution of R1 hydroxide; then
adding R2 persulfate; and then
allowing a reaction to form a product comprising said material,
wherein R1 denotes one singly charged cation and R2 denotes either (a) two singly charged cations or (b) one doubly charged cation;
wherein the monomer is selected from the group consisting of 3-amino-1H-pyrazole-4-carboxylate, 3-amino-5-chloro-1 H-pyrazole-4-carboxylate, 3-amino-5-bromo-1H-pyrazole-4-carboxylate, 3-amino-5-fluoro-1H-pyrazole-4-carboxylate, 3-amino-5-iodo-1H-pyrazole-4-carboxylate, 3,5-diamino-1H-pyrazole-4-carboxylate, 3-amino-5-NHR-1H-pyrazole-4-carboxylate, 3-amino-5-N(R) 2 -1H-pyrazole-4-carboxylate, 3-amino-5-hydroxy-1H-pyrazole-4-carboxylate, and 3-amino-5-OR-1H-pyrazole-4-carboxylate,
and wherein R is an alkyl or aromatic group.

11. The method of claim 10 , wherein the R1 hydroxide is selected from the group consisting of potassium hydroxide and sodium hydroxide, and wherein the R2 persulfate is selected from the group consisting of sodium persulfate and copper persulfate.

12. A material comprising a compound selected from the group consisting of poly(3-amino-5-chloro-1 H-pyrazole-4-carboxylate), poly(3-amino-5-bromo-1H-pyrazole-4-carboxylate), poly(3-amino-5-fluoro-1H-pyrazole-4-carboxylate), poly(3-amino-5-iodo-1H-pyrazole-4-carboxylate), poly(3,5-diamino-1H-pyrazole-4-carboxylate), poly(3-amino-5-NHR-1H-pyrazole-4-carboxylate), poly(3-amino-5-N(R) 2 -1H-pyrazole-4-carboxylate), poly(3-amino-5-hydroxy-1H-pyrazole-4-carboxylate), and poly(3-amino-5-OR-1H-pyrazole-4-carboxylate),
wherein R is an alkyl or aromatic group,
and wherein the material is formed by chemical derivatization of poly(3-amino-1H-pyrazole-4-carboxylate).

Assignees

• Us Gov Sec Navy

Inventors

• Martin Brett D
• Deschamps Jeffrey R
• Depriest Jeffrey C
• Giles Ian D

Classifications

• C08G73/0616

  with only two nitrogen atoms in the ring · CPC title

• C08G69/12 Primary

  with both amino and carboxylic groups aromatically bound · CPC title

• C08G69/08 Primary

  derived from amino-carboxylic acids · CPC title