IP Library Granted Patent US 10,650,938
Granted Patent B2
US 10,650,938 · App. 15/746,573 · Granted May 12, 2020

Siloxane copolymer and solid polymer electrolyte comprising such siloxane copolymers

Inventors: Karthikeyan Sivasubramanian (Bangalore, IN); Neeraj Gupta (Bangalore, IN)
Assignee: MOMENTIVE PERFORMANCE MATERIALS INC.
H01B1/122C07F7/188C08G65/336C08G77/045C08G77/18C08G77/46C08G77/485H01G9/028H01G9/2009H01G11/56H01M10/052H01M10/0565H01M2300/0082Y02E60/13
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 10,650,938
App. No.
15/746,573
Granted
May 12, 2020
Kind
B2
Abstract

A silicone polyether for use in forming a solid polymer electrolyte film, the silicone polyether comprising a heterocyclic moiety. The silicone polyether comprising the heterocyclic moiety may be used to provide an electrolyte composition suitable for use in an electrochemical device. The silicone polyether comprising a heterocyclic moiety may also be used to form a solid polymer electrolyte that may be used to form a solid polymer electrolyte film, which may be suitable for use in electrochemical devices.

Claims (34)

1. A silicone polyether of one of the Formula (1) or Formula (2):

where R 1 and R 2 are independently chosen from a C1-C10 alkyl, a C6-C30 aryl, or an alkoxy of the formula —OR 13 , where R 13 is a C1-C10 alkyl; R 3 is a C1-C10 alkylene; each occurrence of R 4 , R 5 , and R 6 is independently chosen from hydrogen or a C1-C10 alkyl; R 7 is a C2-C10 alkylene; R 8 is a C1-C10 alkylene; R 9 is a C1-C10 alkyl; R 10 is a C1-C10 alkylene; R 11 and R 12 are independently chosen from a C1-C10 alkyl, a C6-C30 aryl or an alkoxy of the formula —OR 13 , where R 13 is a C1-C10 alkyl; X is chosen from O, S, N—R 14 or P—R 15 , where R 14 and R 15 are independently chosen from hydrogen or a C1-C10 alkyl; and n is 2-50.

2. The silicone polyether of claim 1 , wherein R 4 , R 5 , and R 6 in Formula (1) are each hydrogen.

3. The silicone polyether of claim 1 , wherein R 1 and R 2 in Formula (1) are independently chosen from methyl, ethyl, propyl, or butyl.

4. The silicone polyether of claim 1 , wherein R 1 and R 2 in Formula (1) are each methyl.

5. The silicone polyether of claim 1 , wherein R 4 , R 5 , and R 6 in Formula (1) are each hydrogen, and R 1 and R 2 in Formula (1) are each methyl.

6. The silicone polyether of claim 1 , wherein R 4 , R 5 , and R 6 in Formula (2) are each hydrogen.

7. The silicone polyether of claim 1 , wherein R 1 , R 2 , R 11 , and R 12 in Formula (2) are independently chosen from methyl, ethyl, propyl or butyl.

8. The silicone polyether of claim 1 , wherein R 1 , R 2 , R 11 , and R 12 in Formula (2) are each methyl.

9. The silicone polyether of claim 1 , wherein R 4 , R 5 , and R 6 in Formula (2) are each hydrogen, and R 1 , R 2 , R 11 , and R 12 in Formula (2) are each methyl.

10. The silicone polyether of claim 1 , wherein X is O.

11. The silicone polyether of claim 1 wherein the silicone polyether is of the formula:

12. An electrolyte composition comprising (i) a silicone polyether, and (ii) a salt, the silicone polyether being chosen from a compound of one of the Formula (1) or Formula (2):

or a combination of two or more thereof; where R 1 and R 2 are independently chosen from a C1-C10 alkyl, a C6-C30 aryl, or an alkoxy of the formula 0R 13 , where R 13 is a C1-C10 alkyl; R 3 is a C1-C10 alkylene; each occurrence of R 4 , R 5 , and R 6 is independently chosen from hydrogen or a C1-C10 alkyl; R 7 is a C2-C10 alkylene; R 8 is a C1-C10 alkylene; R 9 is a C1-C10 alkyl; R 10 is a C1-C10 alkylene; and R 1-2 are independently chosen from a C1-C10 alkyl, a C6-C30 aryl or an alkoxy of the formula —OR 13 , where R 13 is a C1-C10 alkyl; X is chosen from O, S, N—R 14 or P—R 15 , where R 14 and R 15 are independently chosen from H or a C1-C10 alkyl; and n is an integer from 2-50.

13. The electrolyte composition of claim 12 , wherein R 4 , R 5 , and R 6 in the silicone polyether of Formula (1) are each hydrogen.

14. The electrolyte composition of claim 12 , wherein R 1 and R 2 in the silicone polyether of Formula (1) are independently chosen from methyl, ethyl, propyl or butyl.

15. The electrolyte composition of claim 12 , wherein R 1 and R 2 in the silicone polyether of Formula (1) are each methyl.

16. The electrolyte composition of claim 12 , wherein R 4 , R 5 , and R 6 are each hydrogen, and R 1 and R 2 are each methyl in the silicone polyether of Formula (1).

17. The electrolyte composition of claim 12 , wherein R 4 , R 5 , and R 6 in the silicone polyether of Formula (2) are each hydrogen.

18. The electrolyte composition of claim 12 , wherein R 1 , R 2 , R 11 , and R 12 in the silicone polyether of Formula (2) are independently chosen from methyl, ethyl, propyl or butyl.

19. The electrolyte composition of claim 12 , wherein R 1 , R 2 , R 11 , and R 12 in the silicone polyether of Formula (2) are each methyl.

20. The electrolyte composition of claim 12 , wherein R 4 , R 5 , and R 6 are each hydrogen, and R 1 , R 2 , R 11 , and R 12 in the silicone polyether of Formula (2) are each methyl.

21. The electrolyte composition of claim 12 , wherein X is O.

22. The electrolyte composition of claim 12 wherein the silicone polyether is chosen from:

or a combination thereof.

23. The electrolyte composition of claim 12 , wherein the salt is a lithium salt.

24. The electrolyte composition of claim 23 , wherein the lithium salt is chosen from LiClO 4 , LiCF 3 SO 3 , LiBF 4 , LiPF 6 , LiAsF 6 , LiN(SO 2 C2F 5 ) 2 , Li(CF 3 SO 2 )2N, Li(CF 3 SO 2 )3C, LiN(SO 2 C2F 5 )2, lithium alkyl fluorophosphates, organoborate salts, or a combination of two or more thereof.

25. The electrolyte composition of claim 12 , further comprising (iii) a solid polymer.

26. The electrolyte composition of claim 25 , wherein the solid polymer is chosen from polyacrylonitrile (PAN), poly(methyl methacrylate) (PMMA), poly(vinylidene fluoride) (PVDF), poly(vinylidene fluoride-co-hexafluoropropylene), polystyrene, polyvinyl chloride, poly(alkyl methacrylate), poly(alkyl acrylate), styrene butadiene rubber (SBR), poly(vinyl acetate), poly(ethylene oxide) (PEO), or a combination of two or more thereof.

27. The electrolyte composition of claim 25 , further comprising (iv) a plasticizer, wherein the plasticizer is chosen from an alkyl carbonate, a cyclic carbonate, a glyme, a polyalkylene glycol dialkyl ether, or a combination of two or more thereof.

28. The electrolyte composition of claim 12 , wherein the electrolyte composition has an ionic conductivity of about 1×10 −5 S/cm or greater.

29. The electrolyte composition of claim 12 , wherein the electrolyte composition has an ionic conductivity of about 1×10 −4 S/cm or greater.

30. The electrolyte composition of claim 12 , wherein the electrolyte composition has an ionic conductivity of about 1×10 −2 S/cm to about 1×10 −4 S/cm.

31. An electrochemical device comprising the electrolyte composition of claim 12 .

Assignments (10)
RELEASE OF SECURITY INTEREST IN PATENTS PREVIOUSLY RECORDED AT REEL/FRAME (063213/0472) Recorded Oct 22, 2025
From: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 073168/0715 →
RELEASE OF SECURITY INTEREST Recorded Jul 18, 2025
From: KOOKMIN BANK NEW YORK BRANCH
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 072039/0906 →
FIRST LIEN TERM LOAN PATENT SECURITY AGREEMENT Recorded Mar 31, 2023
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 063213/0472 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS Recorded Mar 31, 2023
From: BNP PARIBAS
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 063259/0133 →
RELEASE OF SECURITY INTEREST Recorded Mar 30, 2023
From: KOOKMIN BANK NEW YORK
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 063197/0373 →
SECURITY INTEREST Recorded Mar 30, 2023
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: KOOKMIN BANK NEW YORK BRANCH
Reel/Frame 063197/0475 →
ABL PATENT AGREEMENT Recorded Jun 5, 2019
From: MOMENTIVE PERFORMANCE MATERIALS INC.; MOMENTIVE PERFORMANCE MATERIALS GMBH
To: CITIBANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 049388/0252 →
FIRST LIEN TERM LOAN PATENT AGREEMENT Recorded Jun 5, 2019
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: BNP PARIBAS, AS ADMINISTRATIVE AGENT
Reel/Frame 049387/0782 →
SECOND LIEN TERM LOAN PATENT AGREEMENT Recorded Jun 5, 2019
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: KOOKMIN BANK, NEW YORK BRANCH, AS ADMINISTRATIVE AGENT
Reel/Frame 049388/0220 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 2, 2018
From: SIVASUBRAMANIAN, KARTHIKEYAN; GUPTA, NEERAJ
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 044810/0821 →