Emulsion polymerization of nitriles and other compounds

Patent metadata

Field	Value
Publication number	US-11732385-B2
Application number	US-201916396862-A
Country	US
Kind code	B2
Filing date	Apr 29, 2019
Priority date	Apr 30, 2018
Publication date	Aug 22, 2023
Grant date	Aug 22, 2023

Abstract

The present disclosure relates to a method that includes polymerizing a nitrile with an acrylate ester to form a copolymer, in a mixture that includes water and an alcohol (R2—OH), according to the following reactionwhere R1 includes at least one of a first aliphatic group or hydrogen, R2 comprises at least one of a second aliphatic group or hydrogen, 100≤m≤4000, and 1≤n≤4000. In some embodiments of the present disclosure, the mixture may be an emulsion.

First claim

What is claimed is:

1. A method comprising:
reacting a monomer having the structure

 with ammonia to form a mixture comprising acrylonitrile, an alcohol, and water; and
polymerizing the acrylonitrile with at least a portion of the monomer remaining in the mixture to form a copolymer having the structure

 wherein:
R 1 comprises at least one of a first aliphatic group or hydrogen,
100≤m≤4000, and
1≤n≤4000.

2. The method of claim 1 , wherein the mixture is an emulsion.

3. The method of claim 1 , wherein the copolymer comprises

4. The method of claim 1 , wherein the copolymer contains randomly dispersed repeat units derived from the acrylonitrile and randomly dispersed repeat units derived from the monomer.

5. The method of claim 3 , wherein the copolymer has a molecular weight between about 5.4 kDa and about 600 kDa.

6. The method of claim 1 , wherein the mixture further comprises a surfactant.

7. The method of claim 1 , wherein the mixture further comprises a chain transfer agent (CTA).

8. The method of claim 1 , wherein the copolymer has a peak temperature between about 200° C. and about 400° C., as determined by differential scanning calorimetry.

9. The method of claim 1 , wherein the polymerizing is performed at a temperature between about 25° C. and about 100° C.

10. The method of claim 1 , wherein the copolymer has an end group comprising at least one of an alkyl group or an alkoxy group.

11. The method of claim 1 , further comprising converting the copolymer to a carbon fiber.

12. The method of claim 3 , wherein the copolymer comprises a molar ratio of a repeat unit derived from the acrylonitrile (AN) to a repeat unit derived from the monomer (M) between about 96:4 and about 97:3.

Assignees

• Alliance Sustainable Energy
• Ut Battelle Llc

Inventors

• Meek Kelly Marie
• Eaton Todd R
• Rorrer Nicholas A
• Karp Eric M
• Naskar Amit Kumar

Classifications

• D01F9/22 Primary

  from polyacrylonitriles · CPC title

• C01B32/05

  Preparation or purification of carbon not covered by groups C01B32/15, C01B32/20, C01B32/25, C01B32/30 · CPC title

• C07C253/22

  by reaction of ammonia with carboxylic acids with replacement of carboxyl groups by cyano groups · CPC title

• C07C255/08

  Acrylonitrile; Methacrylonitrile · CPC title

• C08F2/26

  anionic · CPC title