IP Library Granted Patent US 9,758,905
Granted Patent B2
US 9,758,905 · App. 14/440,411 · Granted Sep 12, 2017

Process of making carbon fibers derived from lignin/carbon residue

Inventors: Bassam Alnasleh (Parma Heights, OH); Ching-Feng Chang (Strongsville, OH); Omer Gul (Olmsted Falls, OH); Andrew Hausner (Parma Heights, OH); Robert Miller (Southaven, MS); Orest Adrianowycz (Broadview Heights, OH)
Assignee: GrafTech International Holdings Inc.
D01F9/17C07G1/00C08H6/00C08L97/005D01F9/145C08L95/00
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Quick Facts
Patent No.
US 9,758,905
App. No.
14/440,411
Granted
Sep 12, 2017
Kind
B2
Abstract

A method of making a carbon fiber comprising esterification of a lignin precursor with an acid, acid anhydride, or acyl halide, thereby forming a reduced T g lignin. Mixing the reduced T g lignin with a carbon residue selected from the group of coal based raw material, petroleum based raw material and combinations thereof, thereby forming a fiber precursor mixture; and spinning the fiber precursor mixture into a fiber. A method of making a carbon fiber comprising esterification of a lignin with an acid derivative, thereby forming a reduced T g lignin. Mixing the reduced T g lignin with a pitch, thereby forming a fiber precursor mixture; and spinning the fiber precursor mixture into a fiber. A method of making a carbon fiber comprising lowering the T g of a lignin material, thereby forming a reduced T g lignin. Mixing the reduced T g lignin with a carbon residue, thereby forming a fiber precursor mixture and spinning the fiber precursor mixture into a fiber.

Claims (22)

1. A method of making a carbon fiber comprising:

a. lowering the T g of a lignin material, thereby forming a reduced T g lignin;

b. mixing the reduced T g lignin with a carbon residue, thereby forming a fiber precursor mixture; and

c. spinning the fiber precursor mixture into a fiber.

2. The method of claim 1 , wherein the lowering comprises reacting the lignin with an alkylating agent.

3. The method of claim 1 , wherein the lowering comprises the esterification of the lignin.

4. The method of claim 1 , wherein the lowering comprises reacting the lignin with a compound having at least one of the following of a propyl group or longer alkyl chain, an aromatic group, and combinations thereof.

5. The method of claim 1 , wherein the lowering comprises reacting the lignin with a halogenated compound or an acid anhydride.

6. The method of claim 1 , wherein the carbon residue is selected from group comprising decant oil, decant oil based pitches, coal tar pitches, petroleum pitches, coal tar distillates and combinations thereof.

7. The method of claim 1 , wherein the T g of the reduced T g lignin is within 50° C. of the T g of the carbon residue.

8. The method of claim 1 , wherein the reduced T g lignin is formed by esterification of a lignin with an acid derivative and wherein the carbon residue is from a pitch.

9. The method of claim 8 , wherein the acid derivative includes at least one of the following of a propyl group or longer alkyl chain, an aromatic group, and combinations thereof.

10. The method of claim 8 , wherein the acid derivative comprises a halogenated compound, or an anhydride.

11. The method of any of claim 8 , wherein the T g of the reduced T g lignin is within 50° C. of the T g of the carbon residue.

12. The method of claim 1 , wherein the reduced T g lignin is formed by esterification of a lignin precursor with an acid, acid anhydride, alkyl halide, or acyl halide, and wherein the carbon residue is selected from the group of coal based raw material, petroleum based raw material and combinations thereof.

13. The method of claim 12 wherein the acid comprises an acid having a longer alkyl chain than acetic acid.

14. The method of claim 12 , wherein the acid includes an ethyl group or longer alkyl chain.

15. The method of claim 12 wherein the acid includes one or more selected from the group of compounds having 4 to 22 carbon atoms and a terminal carboxylic functional group.

16. The method of claim 12 , wherein the reduced T g lignin and the carbon residue have a similar polarity, whereby the carbon residue and lignin have a compatible viscoelastic state at a same point in time in the method.

17. The method of claim 12 , wherein the carbon residue comprises coal tar pitch or decant oil.

18. The method of claim 12 , wherein the carbon residue is selected from group comprising decant oil, decant oil based pitches, coal tar pitches, petroleum pitches, coal tar distillates and combinations thereof.

19. The method of claim 12 , wherein the T g of the reduced T g lignin is within 50° C. of the T g of the carbon residue.

Assignments (10)
SECURITY INTEREST Recorded Dec 23, 2024
From: GRAFTECH INTERNATIONAL HOLDINGS INC.
To: GLAS AMERICAS LLC
Reel/Frame 069666/0444 →
TERMINATION AND RELEASE OF PATENT SECURITY AGREEMENT (REEL 064075 FRAME 0455) Recorded Dec 23, 2024
From: U.S. BANK TRUST COMPANY
To: GRAFTECH INTERNATIONAL HOLDINGS INC.
Reel/Frame 069762/0491 →
TERMINATION AND RELEASE OF PATENT SECURITY AGREEMENT (REEL 054724 FRAME 0588 AND 063798 FRAME 0928) Recorded Dec 23, 2024
From: U.S. BANK TRUST COMPANY
To: GRAFTECH INTERNATIONAL HOLDINGS INC.
Reel/Frame 069762/0518 →
SECURITY INTEREST Recorded Dec 23, 2024
From: GRAFTECH INTERNATIONAL HOLDINGS INC.
To: U.S. BANKS TRUST COMPANY, NATIONAL ASSOCIATION
Reel/Frame 072905/0497 →
SECURITY INTEREST Recorded Dec 23, 2024
From: GRAFTECH INTERNATIONAL HOLDINGS INC.
To: U.S. BANKS TRUST COMPANY, NATIONAL ASSOCIATION
Reel/Frame 072905/0832 →
SECURITY INTEREST Recorded Jun 27, 2023
From: GRAFTECH INTERNATIONAL HOLDINGS INC.
To: U.S. BANK TRUST COMPANY, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 064075/0455 →
SECURITY INTEREST Recorded Dec 22, 2020
From: GRAFTECH INTERNATIONAL HOLDINGS INC.
To: U.S. BANK NATIONAL ASSOCIATION, AS AGENT
Reel/Frame 054724/0588 →
RELEASE OF SECURITY INTEREST Recorded Feb 12, 2018
From: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
To: GRAFTECH INTERNATIONAL HOLDINGS INC.
Reel/Frame 045308/0567 →
SECURITY INTEREST Recorded Feb 12, 2018
From: GRAFTECH INTERNATIONAL HOLDINGS INC.
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 045308/0591 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 8, 2017
From: ADRIANWYCZ, OREST L.; ALNASLEH, BASSAM; CHANG, CHING-FENG; GUL, OMER; MILLER, ROBERT E.; HAUSNER, ANDREW
To: GRAFTECH INTERNATIONAL HOLDINGS INC.
Reel/Frame 043226/0387 →
Continuity (2)
Provisional Application 61727190 · Nov 16, 2012
Related Publication 20150284880A1 · Oct 8, 2015