IP Library Granted Patent US 11,732,385
Granted Patent B2
US 11,732,385 · App. 16/396,862 · Granted Aug 22, 2023

Emulsion polymerization of nitriles and other compounds

Inventors: Kelly Marie Meek (Golden, CO); Todd R. Eaton (Denver, CO); Nicholas A. Rorrer (Golden, CO); Eric M. Karp (Denver, CO); Amit Kumar Naskar (Knoxville, TN)
Assignees: Alliance for Sustainable Energy, LLC; UT-Battelle, LLC
D01F9/22C01B32/05C07C253/22C07C255/08C08F2/26C08F220/44
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Quick Facts
Patent No.
US 11,732,385
App. No.
16/396,862
Granted
Aug 22, 2023
Kind
B2
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 (R 2 —OH), according to the following reaction where R 1 includes at least one of a first aliphatic group or hydrogen, R 2 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.

Claims (19)

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.

Assignments (4)
CHANGE OF NAME Recorded Dec 16, 2025
From: ALLIANCE FOR SUSTAINABLE ENERGY, LLC
To: ALLIANCE FOR ENERGY INNOVATION, LLC
Reel/Frame 073993/0276 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 21, 2022
From: MEEK, KELLY MARIE; NASKAR, AMIT KUMAR
To: UT-BATTELLE, LLC
Reel/Frame 059665/0072 →
CONFIRMATORY LICENSE Recorded May 17, 2019
From: NATIONAL RENEWABLE ENERGY LABORATORY
To: UNITED STATES DEPARTMENT OF ENERGY
Reel/Frame 049212/0432 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 14, 2019
From: EATON, TODD R.; RORRER, NICHOLAS A.; KARP, ERIC M.
To: ALLIANCE FOR SUSTAINABLE ENERGY, LLC
Reel/Frame 049176/0358 →
Continuity (2)
Provisional Application 62664383 · Apr 30, 2018
Related Publication 20190330400A1 · Oct 31, 2019