IP Library › Granted Patent US 12,230,751
Granted Patent B2
US 12,230,751 · App. 17/681,034 · Granted Feb 18, 2025

Nitrile-substituted silanes and electrolyte compositions and electrochemical devices containing them

Inventors: Jose Adrian Pena Hueso (Madison, WI); David Osmalov (Madison, WI); Jian Dong (Madison, WI); Monica Usrey (Madison, WI); Michael Pollina (Madison, WI); Robert C. West (Madison, WI)
Assignee: Silatronix, Inc
H01M10/056C07F7/081C07F7/12C07F7/1804H01G11/58H01G11/60H01G11/62H01M10/0525H01M10/0569H01M2300/0002H01M2300/0028H01M2300/0031H01M2300/0034Y02E60/10Y02E60/13Y02P70/50
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 12,230,751
App. No.
17/681,034
Granted
Feb 18, 2025
Kind
B2
Abstract

Described herein are liquid, organosilicon compounds that including a substituent that is a cyano (—CN), cyanate (—OCN), isocyanate (—NCO), thiocyanate (—SCN) or isothiocyanate (—NCS). The organosilicon compounds are useful in electrolyte compositions and can be used in any electrochemical device where electrolytes are conventionally used.

Claims (21)

1. An electrolyte composition comprising a compound having a structure as shown in Formula III:

wherein R 1 , R 2 , and R 3 are the same or different and are independently selected from the group consisting of C 1 to C 6 linear or branched alkyl and halogen, and wherein at least one of R 1 , R 2 , or R 3 is halogen;

“Spacer” is selected from the group consisting of C 1 to C 6 alkylene, alkenylene, and alkynylene; and

R 4 is selected from the group consisting of cyano (—CN), cyanate (—OCN), isocyanate (—NCO), thiocyanate (—SCN) and isothiocyanate (—NCS);

in combination with a lithium-containing salt,

wherein the electrolyte composition undergoes no more than about 6% thermal decomposition when held at a temperature of about 150° C. for about 1 hour, with LiPF 6 as the lithium-containing salt.

2. The electrolyte composition of claim 1 , wherein R 1 , R 2 , and R 3 are selected from the group consisting of C 1 to C 3 alkyl, chloro, and fluoro.

3. The electrolyte composition of claim 1 , wherein at least one of R 1 , R 2 , and R 3 is fluorine.

4. The electrolyte composition of claim 1 , wherein at least two of R 1 , R 2 , and R 3 are halogen.

5. The electrolyte composition of claim 1 , wherein at least two of R 1 , R 2 , and R 3 are fluorine.

6. The electrolyte composition of claim 1 , wherein R 4 is cyano.

7. The electrolyte composition of claim 6 , wherein at least one of R 1 , R 2 , and R 3 is fluorine.

8. The electrolyte composition of claim 1 , wherein R 4 is cyanate.

9. The electrolyte composition of claim 8 , wherein at least one of R 1 , R 2 , and R 3 is fluorine.

10. The electrolyte composition of claim 1 , wherein R 4 is isocyanate.

11. The electrolyte composition of claim 10 , wherein at least one of R 1 , R 2 , and R 3 is fluorine.

12. The electrolyte composition of claim 1 , wherein R 4 is thiocyanate.

13. The electrolyte composition of claim 12 , wherein at least one of R 1 , R 2 , and R 3 is fluorine.

14. The electrolyte composition of claim 1 , wherein R 4 is isothiocyanate.

15. The electrolyte composition of claim 14 , wherein at least one of R 1 , R 2 , and R 3 is fluorine.

16. An electrochemical device comprising an electrolyte composition as recited in claim 1 .

Assignments (1)
CHANGE OF NAME Recorded May 12, 2025
From: SILATRONIX, INC.
To: ORBIA FLUOR & ENERGY MATERIALS USA, INC.
Reel/Frame 071269/0662 →
Continuity (5)
Continuation 15813243 · Nov 15, 2017
Continuation 15219952 · Jul 26, 2016
Continuation 14295779 · Jun 4, 2014
Provisional Application 61830851 · Jun 4, 2013
Related Publication 20220181674A1 · Jun 9, 2022
References Cited (42)
US 3053874A · Pepe et al. · 1962 [cited by applicant]
US 3128297A · Bank et al. · 1964 [cited by applicant]
US 4730073A · Takago et al. · 1988 [cited by applicant]
US 5247110A · Bank · 1993 [cited by applicant]
US 5374757A · Bank et al. · 1994 [cited by applicant]
US 20070059588A1 · Lee · 2007 [cited by examiner]
US 20070065728A1 · Zhang et al. · 2007 [cited by applicant]
US 20090208809A1 · Hamrock et al. · 2009 [cited by applicant]
US 20110266490A1 · West et al. · 2011 [cited by applicant]
US 20120315536A1 · Bhat et al. · 2012 [cited by applicant]
US 20130022861A1 · Miyagi et al. · 2013 [cited by examiner]
US 20130236777A1 · Taki et al. · 2013 [cited by applicant]
US 20140356735A1 · Pena Hueso et al. · 2014 [cited by applicant]
US 20150203516A1 · Zhang · 2015 [cited by applicant]
US 20170283443A1 · Syvret et al. · 2017 [cited by applicant]
CN 101859913A · 2010 [cited by examiner]
CN 102924495A · 2013 [cited by applicant]
CN 102504058A · 2014 [cited by applicant]
CN 102504058B · 2014 [cited by applicant]
EP 0653429A1 · 1995 [cited by applicant]
GB 772986A · 1957 [cited by applicant]
GB 778272A · 1957 [cited by applicant]
JP 270508A · 1987 [cited by applicant]
JP 032361 · 1991 [cited by examiner]
JP 2000243440A · 2000 [cited by applicant]
JP 2000342440 · 2000 [cited by applicant]
JP 2001524312A · 2001 [cited by applicant]
JP 07188259A · 2005 [cited by applicant]
JP 2014051447A · 2014 [cited by applicant]
SU 352554 · 1973 [cited by applicant]
Examiner's Answer mailed Aug. 20, 2021 in parent U.S. Appl. No. 15/813,243 (Year: 2021). [cited by examiner]
PTAB Decision mailed Jan. 7, 2022 in parent U.S. Appl. No. 15/813,243 (Year: 2022). [cited by examiner]
Machine translation of CN 101859913A, Yong et al. (Year: 2010). [cited by examiner]
Machine translation of JP 2000-243440, Toriida et al. (Year: 2000). [cited by examiner]
Database GPD [Online] Mintel, compound summary for CIS 220790741 Schembl 8087246, XPo55297907, retrieved from www.gnpd.com, Database accession No. CID 22079074, Abstract. [cited by applicant]
Kricheldorf, H. R. “Synthese und Eigenschaften N-silylierter cyclischer Urethane sowie deren isomerer Isocyanate und Isothiocyanate.” [cited by applicant]
Matsuhashi, Hayao, et al. “Palladium catalyzed cross-coupling reaction of functionalized alkyltrifluorosilanes with aryl halides.” [cited by applicant]
Pubchem. Compound Summary for: CID 4589186. Create Date: Sep. 16, 2005. [retrieved on Nov. 6, 2014]. Retrieved from the Internet. <URL: https://pubchem.ncbi.nlm.nih.gov/compound/4589186?from=summary>. entire document. [cited by applicant]
Pubchem. Compound Summary for: CID 22079074. Create Date: Dec. 5, 2007. [retrieved on Nov. 6, 2014]. Retrieved from the Internet. <URL: https://pubchem.ncbi.nlm.nih.gov/compound/22079074?from=summary>. entire document. [cited by applicant]
Pubchem. Substance record for SID 77858884. Deposit Date: Jun. 12, 2009, [retrieved on Jan. 15, 2016]. Retrieved from the Internet. URL:https://puchem.ncbi.nim.nih.gov/substance/77858884. Entire document. [cited by applicant]
Pubchem. Compound Summary for: CID 57848168. Create Date: Aug. 19, 2012. [retrieved on Nov. 6, 2014]. Retrieved from the Internet. RL: https://pubchem.ncbi.nlm.nih.gov/compound/57848168?from=summary>. entire document. [cited by applicant]
Scholl, Roger L., Gary E. Maciel, and W. Kenneth Musker. “Silicon-29 chemical shifts of organosilicon compounds.” [cited by applicant]