IP Library Granted Patent US 9,923,243
Granted Patent B2
US 9,923,243 · App. 14/371,491 · Granted Mar 20, 2018

Silicone epoxy ether compositions, methods for making same and uses therefor

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Quick Facts
Patent No.
US 9,923,243
App. No.
14/371,491
Granted
Mar 20, 2018
Kind
B2
Abstract

The present invention relates to silicone epoxy compositions, methods for making same and uses therefore. In one embodiment, the silicone epoxy ether compositions of the present invention are silane epoxy polyethers that contain at least one epoxy functionality. In another embodiment, the silicone epoxy ether compositions of the present invention are siloxane epoxy polyethers that contain at least one epoxy functionality. In still another embodiment, the present invention relates to silicone epoxy polyether compositions that are suitable for use as an electrolyte solvent in a lithium-based battery, an electrochemical super-capacitors or any other electrochemical device.

Claims (49)

1. A silicon-containing polyether electrolyte solvent composition comprising:

(a) at least one compound selected from the compositions represented by the following structure:

M 1 a M 2 b D 1 c D 2 d T 1 e T 2 f Q g

wherein M 1 is selected from R 1 R 2 R 3 SiO 1/2 or M′ a monovalent organic radical containing one or more heteroatoms O, N and/or S; wherein M 2 is selected from R 4 R 5 R 6 SiO 1/2 ; wherein D 1 is selected from R 7 R 8 SiO 2/2 or D′ a divalent organic radical containing one or more heteroatoms O, N and/or S; wherein D 2 is selected from R 9 R 10 SiO 2/2 ; wherein T 1 is selected from R 11 SiO 3/2 or T′ a trivalent organic radical containing one or more heteroatoms O, N and/or S; wherein T 2 is selected from R 13 SiO 3/2 ; wherein Q is selected from SiO 4/2 or Q′ a tetravalent organic radical containing one or more heteroatoms O, N and/or S;

R 1 , R 2 , R 3 , R 5 , R 6 , R 7 , R 8 , R 10 , and R 11 are each independently selected from monovalent hydrocarbon radicals having from 1 to about 10 carbon atoms; monovalent hydrocarbon heteroatom-containing radicals having from 1 to about 10 carbon atoms wherein the one or more heteroatoms are selected from one or more halogens, O, N, or combinations of any two or more thereof; or monovalent polyalkylene oxide residuals;

R 4 , R 9 and R 13 are each independently selected from monovalent radicals that contain an oxirane moiety, with the proviso that at least one of R 1 , R 2 , R 3 , R 5 , R 6 , R 7 , R 8 , R 10 , R 11 , M′, D′, T′ or Q′ contains a polyalkylene oxide residual if none of R 4 , R 9 and R 13 contains a polyalkylene oxide residual;

and wherein a, b, c, d, e, f, and g are independently selected from either zero or a positive integer subject to the provisos that 0<a+b+c+d+e+f+g<50 and b+d+f+g>0.

2. The composition of claim 1 , wherein the polyalkylene oxide is selected from group represented by the following structure:

—(CH 2 CH 2 O) m (CH 2 CH(CH 3 )O) n (CH 2 CH 2 CH 2 O) z —

wherein m is a positive integer; wherein n and z are independently either zero or a positive integer, with the proviso that 0<m+n+z<20.

3. The composition of claim 1 , wherein the composition is an electrolytic solvent for at least one lithium salt.

4. The composition of claim 3 , wherein the lithium salt is selected from one or more of LiClO 4 , LiCF 3 SO 3 , LiBF 4 , LiPF 6 , LiAsF 6 , LiN(SO 2 CF 3 ) 2 , LiTFSI, LIBOB), or combinations of any two or more thereof.

5. The composition of claim 3 , wherein the lithium salt is LiPF 6 .

6. The composition of claim 1 , wherein the composition is an electrolytic solvent for at least one lithium salt and wherein the electrolytic solvent is capable of solubilizing up to about 2 M of the one or more lithium salts.

7. The composition of claim 1 , wherein the composition is an electrolytic solvent for at least one lithium salt and wherein the electrolytic solvent is capable of solubilizing up to about 1.9 M of the one or more lithium salts.

8. The composition of claim 1 , wherein the composition is an electrolytic solvent for at least one lithium salt and wherein the electrolytic solvent is capable of solubilizing up to about 1.8 M of the one or more lithium salts.

9. The composition of claim 1 , wherein the composition is an electrolytic solvent for at least one lithium salt and wherein the electrolytic solvent is capable of solubilizing up to about 1.7 M of the one or more lithium salts.

10. The composition of claim 1 , wherein the composition is an electrolytic solvent for at least one lithium salt and wherein the electrolytic solvent is capable of solubilizing up to about 1.5 M of the one or more lithium salts.

11. The composition of claim 1 , wherein the composition is an electrolytic solvent for at least one lithium salt and wherein the electrolytic solvent is capable of solubilizing up to about 1.2 M of the one or more lithium salts.

12. The composition of claim 1 , wherein the composition is an electrolytic solvent for at least one lithium salt and wherein the electrolytic solvent is capable of solubilizing up to about 1 M of the one or more lithium salts.

13. The composition of claim 1 , wherein the combination of a composition in accordance with claim 1 and at least one lithium salts yields a solution having an ionic conductivity of greater than about 0.5 mS/cm at room temperature.

14. The composition of claim 1 , wherein the combination of a composition in accordance with claim 1 and at least one lithium salts yields a solution having an ionic conductivity of greater than about 1 mS/cm at room temperature and wherein such solution is free of one or more alkyl carbonate compounds.

15. The composition of claim 1 , wherein the electrolyte solvent composition further comprises from about 1 percent by volume to about 10 percent by volume of one or more of a compound selected from allyl glycidyl ethers, diethylene glycol monomethylethers, allyl methoxy polyethers, or any combination of two or more thereof in combination with the one or more silicon-containing polyether compounds.

16. The composition of claim 1 , wherein the electrolyte solvent composition further comprises at least one alkyl carbonate compound in combination with one or more silicon-containing polyether compounds.

17. The composition of claim 16 , wherein the at least one alkyl carbonate is selected from ethylene carbonate, dimethyl carbonate, or mixtures thereof.

18. The composition of claim 16 , wherein the at least one alkyl carbonate is present in a range of about 20 to about 50 percent by volume based on the total volume of the one or more silicon-containing polyether compounds and the one or more alkyl carbonates.

19. The silicon-containing polyether electrolyte solvent composition of claim 1 comprising:

(a) at least one compound selected from the compositions represented by the Formulas (IV) and/or (V):

wherein the PEG portion of the compound of Formula (V) represents —(OCH 2 CH 2 ) 4 OCH 3 .

20. The composition of claim 19 , wherein the composition is an electrolytic solvent for at least one lithium salt selected from LiClO 4 , LiCF 3 SO 3 , LiBF 4 , LiPF 6 , LiAsF 6 , LiN(SO 2 CF 3 ) 2 , LiTFSI, LiBOB, or combinations of any two or more thereof.

21. The composition of claim 20 , wherein the lithium salt is selected from one or more of LiPF 6 , LiBOB and/or LiTFSI.

22. The composition of claim 20 , wherein the lithium salt is LiPF6.

23. The composition of claim 19 , wherein the composition is an electrolytic solvent for at least one lithium salt and wherein the electrolytic solvent is capable of solubilizing up to about 2 M of the one or more lithium salts.

24. The composition of claim 19 , wherein the composition is an electrolytic solvent for at least one lithium salt and wherein the electrolytic solvent is capable of solubilizing up to about 1.9 M of the one or more lithium salts.

25. The composition of claim 19 , wherein the composition is an electrolytic solvent for at least one lithium salt and wherein the electrolytic solvent is capable of solubilizing up to about 1.8 M of the one or more lithium salts.

26. The composition of claim 19 , wherein the composition is an electrolytic solvent for at least one lithium salt and wherein the electrolytic solvent is capable of solubilizing up to about 1.7 M of the one or more lithium salts.

27. The composition of claim 19 , wherein the composition is an electrolytic solvent for at least one lithium salt and wherein the electrolytic solvent is capable of solubilizing up to about 1.5 M of the one or more lithium salts.

28. The composition of claim 19 , wherein the composition is an electrolytic solvent for at least one lithium salt and wherein the electrolytic solvent is capable of solubilizing up to about 1.2 M of the one or more lithium salts.

29. The composition of claim 19 , wherein the composition is an electrolytic solvent for at least one lithium salt and wherein the electrolytic solvent is capable of solubilizing up to about 1 M of the one or more lithium salts.

30. The composition of claim 19 , wherein the combination of a composition in accordance with claim 1 and at least one lithium salts yields a solution having an ionic conductivity of greater than about 1 mS/cm at room temperature.

31. The composition of claim 19 , wherein the combination of a composition in accordance with claim 1 and at least one lithium salts yields a solution having an ionic conductivity of greater than about 1 mS/cm at room temperature and wherein such solution is free of one or more alkyl carbonate compounds.

32. The composition of claim 19 , wherein the composition of Formula (IV) is synthesized according to the following reaction scheme:

33. The composition of claim 19 , wherein the composition of Formula (V) is synthesized according to the following reaction scheme:

34. The composition of claim 19 , wherein the electrolyte solvent composition further comprises from about 1 percent by volume to about 10 percent by volume of one or more of a compound selected from allyl glycidyl ethers, diethylene glycol monomethylethers, allyl methoxy polyethers, or any combination of two or more thereof in combination with the one or more silicon-containing polyether compounds.

35. The composition of claim 19 , wherein the electrolyte solvent composition further comprises at least one alkyl carbonate compound in combination with one or more silicon-containing polyether compounds.

36. The composition of claim 35 , wherein the at least one alkyl carbonate is selected from ethylene carbonate, dimethyl carbonate, or mixtures thereof.

37. The composition of claim 35 , wherein the at least one alkyl carbonate is present in a range of about 20 to about 50 percent by volume based on the total volume of the one or more silicon-containing polyether compounds and the one or more alkyl carbonates.

38. An electrochemical device comprising the composition of claim 1 .

39. An electrochemical device comprising the composition of claim 19 .

Assignments (18)
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 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS Recorded Mar 31, 2023
From: BNP PARIBAS
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 063259/0133 →
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 →
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 →
RELEASE OF SECURITY INTEREST Recorded Nov 11, 2020
From: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 054336/0279 →
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 →
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 →
RELEASE OF SECURITY INTEREST Recorded May 15, 2019
From: BOKF, NA
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 049249/0271 →
RELEASE OF SECURITY INTEREST Recorded May 15, 2019
From: BOKF, NA
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 049194/0085 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 1, 2016
From: GUPTA, NEERAJ; SIVASUBRAMANIAN, KARTHIKEYAN; PHUKAN, MONJIT
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 038760/0855 →
NOTICE OF CHANGE OF COLLATERAL AGENT - ASSIGNMENT OF SECURITY INTEREST IN INTELLECTUAL PROPERTY - SECOND LIEN Recorded Mar 6, 2015
From: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A. AS COLLATERAL AGENT
To: BOKF, NA, AS SUCCESSOR COLLATERAL AGENT
Reel/Frame 035137/0263 →
NOTICE OF CHANGE OF COLLATERAL AGENT - ASSIGNMENT OF SECURITY INTEREST IN INTELLECTUAL PROPERTY Recorded Mar 6, 2015
From: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A. AS COLLATERAL AGENT
To: BOKF, NA, AS SUCCESSOR COLLATERAL AGENT
Reel/Frame 035136/0457 →
SECURITY INTEREST Recorded Jan 13, 2015
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 034759/0723 →
SECURITY INTEREST Recorded Oct 27, 2014
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS COLLATERAL AGENT
Reel/Frame 034066/0662 →
SECURITY INTEREST Recorded Oct 27, 2014
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS COLLATERAL AGENT
Reel/Frame 034066/0570 →