IP Library Granted Patent US 11,742,523
Granted Patent B2
US 11,742,523 · App. 17/162,987 · Granted Aug 29, 2023

Electrolyte solutions

Inventors: Jefferson Thomas Ebert (Houston, TX); Benjamin Haseltine (Houston, TX)
Assignee: Ascend Performance Materials Operations LLC
H01M10/0569H01M10/0525H01M10/0567H01M10/0568H01M2300/0034
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 11,742,523
App. No.
17/162,987
Granted
Aug 29, 2023
Kind
B2
Abstract

An electrolyte solution comprising an ionic component, a base solvent, and an additive package. The additive package comprises a trinitrile compound and a cyclic carbonate. The electrolyte solution comprises symmetric linear carbonate in an amount greater than 19 wt %, based on the total weight of the electrolyte solution.

Claims (45)

1. An electrolyte solution comprising:

an ionic component;

a base solvent comprising symmetric linear carbonate; and

an additive package comprising:

a trinitrile compound having a chemical structure C x H 2−1 (CN) 3 , wherein x is from 4 to 10; and

a cyclic carbonate compound having a chemical structure:

wherein R 1 , R 2 R 3 , R 4 , R 6 , and R 6 are independently selected from hydrogen, halogen, (C 1 -C 10 )alkyl, or (C 1 -C 10 ) haloalkyl,

wherein the electrolyte solution comprises symmetric linear carbonate in an amount greater than 25 wt % based on the total weight of the electrolyte solution.

2. The electrolyte solution of claim 1 , wherein the symmetric linear carbonate comprises diethyl carbonate, or dimethyl carbonate, or combinations thereof, and wherein the diethyl carbonate, or dimethyl carbonate, or combinations thereof is present in an amount greater than 25 wt %, based on the total weight of the electrolyte solution.

3. The electrolyte solution of claim 1 , wherein the cyclic carbonate compound is vinylene carbonate or ethylene carbonate.

4. The electrolyte solution of claim 1 , wherein the cyclic carbonate compound is fluoroethylene carbonate.

5. The electrolyte solution of claim 1 , wherein the electrolyte solution comprises less than 30 wt % total cyclic carbonates.

6. The electrolyte solution of claim 1 , wherein the electrolyte solution comprises less than 30 wt % ethylene carbonate.

7. The electrolyte solution of claim 1 , wherein the electrolyte solution comprises less than 6 wt % fluoroethylene carbonate.

8. The electrolyte solution of claim 1 , wherein the electrolyte solution further comprises asymmetric linear carbonates in an amount less than 50 wt %.

9. The electrolyte solution of claim 1 , wherein the electrolyte solution further comprises ethylmethyl carbonate in an amount less than 50 wt %.

10. The electrolyte solution of claim 1 , wherein the trinitrile compound comprises tricyanohexane.

11. The electrolyte solution of claim 1 , wherein a weight ratio of the cyclic carbonate compound to the trinitrile compound is from 0.5:1 to 5:1.

12. The electrolyte solution of claim 1 , wherein the additive package further comprises a sulfonate.

13. The electrolyte solution of claim 1 , wherein the trinitrile compound comprises tricyanohexane, wherein the carbonate compound comprises vinylidene carbonate, and wherein the solution demonstrates a voltage drop of less than 0.25 V.

14. The electrolyte solution of claim 1 , further comprising methylene methane disulfonate or fluoroethylene carbonate or combinations thereof.

15. The electrolyte solution of claim 1 , wherein the electrolyte solution exhibits a first cycle coulombic efficiency greater than 0.85 over 20 cycles.

16. The electrolyte solution of claim 1 , wherein the electrolyte solution exhibits an impedance growth of less than 20% over 25 cycles.

17. An electrolyte solution comprising:

an ionic component;

a base solvent; and

an additive package comprising:

a trinitrile compound having a chemical structure C x H 2x−1 (CN) 3 , wherein x is from 4 to 10; and

a sulfonate compound having a chemical structure:

wherein a and b are independently from 1 to 4,

wherein the electrolyte solution comprises symmetric linear carbonates in an amount greater than 25 wt %, based on the total weight of the electrolyte solution; and

wherein the electrolyte solution exhibits a first cycle coulombic efficiency greater than 0.85 over 20 cycles and/or an impedance growth of less than 20% over 25 cycles.

18. The electrolyte solution of claim 17 , wherein the trinitrile compound comprises tricyanohexane.

19. A secondary cell comprising:

a cathode, optionally having a cathode active material comprising a lithium-containing transition metal composite oxide;

an anode optionally comprising graphite; and

an electrolyte solution comprising:

an ionic component;

a base solvent; and

an additive package comprising:

a trinitrile compound having a chemical structure C x H 2−1 (CN) 3 , wherein x is from 4 to 10; and

a cyclic carbonate compound having a chemical structure:

wherein R 1 , R 2 R 3 , R 4 , R 6 , and R 6 are independently selected from hydrogen, halogen, (C 1 -C 10 )alkyl, or (C 1 -C 10 )haloalkyl,

wherein the electrolyte solution comprises symmetric linear carbonate in an amount greater than 25 wt %, based on the total weight of the electrolyte solution.

20. The secondary cell of claim 19 , wherein the cell demonstrates a 5 day gas generation value of less than 4.9 mL when operated at 4.48 volts.

Assignments (6)
RELEASE OF SECURITY INTEREST Recorded Dec 23, 2025
From: WILMINGTON SAVINGS FUND SOCIETY, FSB
To: ASCEND PERFORMANCE MATERIALS OPERATIONS LLC
Reel/Frame 074050/0090 →
SECURITY INTEREST Recorded Dec 23, 2025
From: ASCEND PERFORMANCE MATERIALS OPERATIONS LLC
To: WILMINGTON SAVINGS FUND SOCIETY, FSB
Reel/Frame 074056/0183 →
SECURITY INTEREST Recorded Dec 19, 2025
From: ASCEND PERFORMANCE MATERIALS OPERATIONS LLC
To: WELLS FARGO BANK, NATIONAL ASSOCIATION
Reel/Frame 074007/0183 →
SECURITY INTEREST Recorded Apr 10, 2025
From: BANK OF AMERICA, N.A.
To: WILMINGTON SAVINGS FUND SOCIETY, FSB
Reel/Frame 070811/0705 →
SECURITY INTEREST Recorded Dec 8, 2022
From: ASCEND PERFORMANCE MATERIALS OPERATIONS LLC
To: WELLS FARGO CAPITAL FINANCE, LLC
Reel/Frame 062094/0172 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 25, 2021
From: EBERT, JEFFERSON THOMAS; HASELTINE, BENJAMIN
To: ASCEND PERFORMANCE MATERIALS OPERATIONS LLC
Reel/Frame 056341/0859 →