IP Library Granted Patent US 8,778,534
Granted Patent B2
US 8,778,534 · App. 12/501,946 · Granted Jul 15, 2014

Phosphonium ionic liquids, compositions, methods of making and batteries formed there from

Inventors: J. Adrian Hawkins (Denver, CO); David A. Hudgins (Englewood, CO); Levi J. Irwin (Denver, CO)
Assignee: eSionic ES, Inc.
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Quick Facts
Patent No.
US 8,778,534
App. No.
12/501,946
Granted
Jul 15, 2014
Kind
B2
Abstract

The invention generally encompasses phosphonium ionic liquids and compositions and their use in many applications, including but not limited to: as electrolytes in electronic devices such as memory devices including static, permanent and dynamic random access memory, as battery electrolytes, as a heat transfer medium, fuel cells and electrochromatic devices, among other applications. In particular, the invention generally relates to phosphonium ionic liquids, compositions and molecules possessing structural features, wherein the molecules exhibit superior combination of thermodynamic stability, low volatility, wide liquidus range and ionic conductivity. The invention further encompasses methods of making such phosphonium ionic liquids, compositions and molecules, and operational devices and systems comprising the same.

Claims (121)

1. A battery, comprising:

a positive electrode;

a negative electrode;

a separator between said positive and negative electrode; and

an electrolyte comprising an ionic liquid composition, the ionic liquid composition comprising: a phosphonium based cation of the formula:

and;

one or more anions comprised of any one or more of the following: − O 3 SCF 3 , − O 2 CCF 3 , − O 2 CCF 2 CF 2 CF 3 , CF 3 BF 3 − , C(CN) 3 − , PF 6 − , − O 3 SCH 3 , − O 3 SCF 2 CF 2 CF 3 , − O 2 CH, − O 2 CC 6 H 5 , − OCN, CO 3 2− , or − N(CN) 2 .

2. The battery of claim 1 wherein the electrolyte is a solution and further contains a solvent.

3. The battery of claim 1 wherein one or more of the hydrogen atoms in one or more of the alkyl groups are substituted by fluorine atoms.

4. A battery, comprising:

a positive electrode;

a negative electrode;

a separator between said positive and negative electrode; and

an electrolyte comprising an ionic liquid composition, the ionic liquid composition comprising: one or more phosphonium based cations of the general formula:

R 1 R 2 R 3 R 4 P

wherein: R 1 , R 2 , R 3 and R 4 are each independently an alkyl group comprised of 1 to 4 carbons, and one or more anions, wherein the ionic liquid composition exhibits thermodynamic stability up to a temperature of approximately 375° C., and ionic conductivity up to 10 mS/cm.

5. A battery comprising:

a positive electrode;

a negative electrode;

a separator between said positive and negative electrode; and

an electrolyte comprising an ionic liquid composition, the ionic liquid composition comprising one or more phosphonium based cations of the following formulas:

Cation

R1

R2

R3

R4

P +

Methyl

Methyl

Methyl

Ethyl

P +

Methyl

Methyl

Methyl

Propyl

P +

Methyl

Methyl

Methyl

i-Propyl

P +

Methyl

Methyl

Ethyl

Propyl

P +

Methyl

Methyl

Ethyl

i-Propyl

P +

Methyl

Ethyl

Ethyl

Propyl

P +

Methyl

Ethyl

Ethyl

i-Propyl

P +

Methyl

Ethyl

i-Propyl

i-Propyl

P +

Ethyl

Ethyl

Propyl

i-Propyl

P +

Ethyl

Ethyl

Ethyl

Propyl

P +

Ethyl

Ethyl

Ethyl

i-Propyl

P +

Propyl

Propyl

Propyl

Methyl

P +

Propyl

Propyl

Propyl

Ethyl

P +

Propyl

Propyl

Propyl

i-Propyl

P +

i-Propyl

i-Propyl

i-Propyl

Methyl

P +

i-Propyl

i-Propyl

i-Propyl

Ethyl

P +

i-Propyl

i-Propyl

i-Propyl

Propyl

and;

one or more anions, wherein the one or more anions are comprised of any one or more of the following: − O 3 SCF 3 , − O 2 CCF 3 , − O 2 CCF 2 CF 2 CF 3 , CF 3 BF 3 − , C(CN) 3 − , PF 6 − , − O 3 SCH 3 , − O 3 SCF 2 CF 2 CF 3 , − O 2 CH, − O 2 CC 6 H 5 , − OCN, CO 3 2− , or − N(CN) 2 .

6. The battery of claim 5 wherein one or more of the hydrogen atoms in one or more of the alkyl groups are substituted by fluorine atoms.

7. A battery, comprising:

a positive electrode;

a negative electrode;

a separator between said positive and negative electrode; and

an electrolyte comprising an ionic liquid composition, the ionic liquid composition comprising: a phosphonium based cation of the formula:

and;

one or more anions comprised of any one of more of the following anion mixtures: 1NO 3 − /1O 3 SCF 3 − , 3NO 3 − /1O 3 SCF 3 − , 1NO 3 − /3O 3 SCF 3 − , 1NO 3 − /1N(SO 2 CF 3 ) 2 − , 1NO 3 − /1PF 6 − , 1O 3 SCF 3 − /1N(SO 2 CF 3 ) 2 − , 1O 3 SCF 3 − /1O 3 SC 6 H 4 CH 3 − , 3O 3 SCF 3 − /1O 3 SC 6 H 4 CH 3 − , 1O 3 SCF 3 − /1O 3 SCF 2 CF 2 CF 3 − , 1O 3 SC 6 H 4 CH 3 − /3O 3 SCH 3 − , 1O 3 SC 6 H 4 CH 3 − /1O 3 SCF 2 CF 2 CF 3 − , 3O 3 SC 6 H 4 CH 3 − /1O 3 SCF 2 CF 2 CF 3 − , or 1O 3 SC 6 H 4 CH 3 − /3O 3 SCF 2 CF 2 CF 3 − .

Assignments (5)
MERGER Recorded Apr 27, 2015
From: ESIONIC ES, INC.
To: ESIONIC CORP.
Reel/Frame 035503/0093 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 29, 2013
From: ZETTACORE, INC.
To: ZETTACORE HOLDINGS, LLC
Reel/Frame 030308/0279 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 29, 2013
From: ZETTACORE HOLDINGS, LLC
To: ZETTACORE IONIC LIQUID, INC.
Reel/Frame 030308/0422 →
CHANGE OF NAME Recorded Apr 29, 2013
From: ZETTACORE IONIC LIQUID, INC.
To: ESIONIC ES, INC.
Reel/Frame 030312/0028 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 28, 2009
From: HAWKINS, J. ADRIAN; HUDGINS, DAVID A.; IRWIN, LEVI J.
To: ZETTACORE, INC.
Reel/Frame 023293/0512 →
Continuity (2)
Provisional Application 61080650 · Jul 14, 2008
Related Publication 20100009255A1 · Jan 14, 2010