IP Library Granted Patent US 9,735,411
Granted Patent B2
US 9,735,411 · App. 14/723,132 · Granted Aug 15, 2017

Polymer for use as protective layers and other components in electrochemical cells

Inventors: Veronika G. Viner (Tucson, AZ); Sven Fleischmann (Ludwigshafen, DE)
Assignees: Sion Power Corporation; BASF SE
H01M2/1673C08G75/00H01M2/1653H01M4/13H01M4/134H01M4/38H01M4/382H01M10/052H01M10/0525H01M10/0565H01M2/145H01M4/366H01M2300/0085
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Quick Facts
Patent No.
US 9,735,411
App. No.
14/723,132
Granted
Aug 15, 2017
Kind
B2
Abstract

Polymers for use as protective layers and other components in electrochemical cells are provided. In some embodiments, the electrochemical cell is a lithium-based electrochemical cell.

Claims (53)

1. An electrochemical cell comprising:

a cathode;

an electroactive layer, wherein the electroactive layer comprises an anode active material; and

a polymer layer comprising a polymer comprising polymerized units of a first type of monomer comprising at least two thiol groups, a second type of monomer comprising at least one vinyl group or at least one alkynyl group, and an optional third type of monomer, wherein the polymer layer is arranged between the cathode and the electroactive layer comprising the anode active material.

2. The electrochemical cell of claim 1 , wherein:

(a) the first type of monomer comprises two thiol groups or three thiol groups; and

(b) the second type of monomer comprises 1-3 vinyl groups or 1-3 alkynyl groups.

3. The electrochemical cell of claim 1 , wherein the first type of monomer is a compound of Formula (A) or Formula (B),

HS-L 1 -SH  (A)

R a C(L 2 SH) 3   (B)

wherein:

L 1 or L 2 is optionally substituted alkylene, optionally substituted heteroalkylene, optionally substituted cycloalkylene, optionally substituted heterocycloalkylene, optionally substituted arylene, or optionally substituted heteroarylene; and

R a is H, alkyl, or -L 2 SH.

4. The electrochemical cell of claim 3 , wherein the first type of monomer is a compound of Formula (A), wherein L 1 is —(C 2 -C 3 -alkylene oxide) n -(C 2 -C 3 -alkylene)- or —(C 2 -C 3 -alkylene oxide) n -C(O)—(C 2 -C 3 -alkylene)-, wherein the C 2 -C 3 -alkylene oxide is independently ethylene oxide or 1,2-propylene oxide, wherein n is an integer from 1 to 100.

5. The electrochemical cell of claim 3 , wherein the first type of monomer is a compound of Formula (B), wherein L 2 is —(C 1 -C 3 -alkylene)-(C 2 -C 3 -alkylene oxide) n -(C 1 -C 3 -alkylene)- or —(C 1 -C 3 -alkylene)-(C 2 -C 3 -alkylene oxide) n -OC(O)—(C 1 -C 3 -alkylene) wherein the C 2 -C 3 -alkylene oxide is independently ethylene oxide or 1,2-propylene oxide, —R a is H or alkyl, and n is an integer from 1 to 10.

6. The electrochemical cell of claim 1 , wherein the second type of monomer is a compound of Formula (C),

X 1 -L 3 -R b   (C)

wherein:

X 1 is —CR c ═CH 2 or —C≡CH;

L 3 is optionally substituted alkylene, optionally substituted heteroalkylene, optionally substituted cycloalkylene, optionally substituted heterocycloalkylene, optionally substituted arylene, optionally substituted heteroarylene, —(CO)—, —(CO)O—, —(CO)NH—, —C═NH—,

—NH—, —C(OH)—, —O—, or —S—;

R b is optionally substituted alkyl, optionally substituted heteroalkyl, optionally substituted cycloalkyl, optionally substituted heterocycloalkyl, optionally substituted aryl, or optionally substituted heteroaryl; and

R c is H or alkyl,

or

wherein the second type of monomer is a compound of Formula (D),

X 2 -L 4 -X 3   (D)

wherein:

X 2 and X 3 are —CR d ═CH 2 or —C≡CH;

L 4 is optionally substituted alkylene, optionally substituted heteroalkylene, optionally substituted cycloalkylene, optionally substituted heterocycloalkylene, optionally substituted arylene, optionally substituted heteroarylene, —(CO)—, —(CO)O—, —(CO)NH—, —C═NH—, —NH—, —C(OH)—, —O—, or —S—; and

R d is H or alkyl.

7. The electrochemical cell of claim 6 , wherein L 3 or L 4 comprises an alkylene oxide chain.

8. The electrochemical cell of claim 6 , wherein L 4 has the structure,

wherein each n is independently 0-10 and R 6 is optionally substituted alkylene, optionally substituted heteroalkylene, optionally substituted cycloalkylene, optionally substituted heterocycloalkylene, optionally substituted arylene, or optionally substituted heteroarylene,

or, wherein L 4 is —(O)—(C 2 -C 3 -alkylene oxide) n -, wherein the C 2 -C 3 -alkylene oxide is independently ethylene oxide or 1,2-propylene oxide, and n is an integer from 1 to 10,

or,

wherein L 4 has the structure,

wherein:

R 7 is optionally substituted alkylene, optionally substituted heteroalkylene, optionally substituted cycloalkylene, optionally substituted heterocycloalkylene, optionally substituted arylene, or optionally substituted heteroarylene.

9. The electrochemical cell of claim 1 , wherein the second type of monomer is one of the following compounds,

wherein n is an integer from 1-100.

10. The electrochemical cell of claim 1 , wherein the polymer of the polymer layer comprises the third type of monomer, and wherein the third type of monomer comprises at least one functional group(s) reactive with a thiol group.

11. The electrochemical cell of claim 10 , wherein the third type of monomer is a compound of Formula (E),

R e -L 5 -R f   (E)

wherein L 5 is alkylene, arylene, arylene-alkylene-arylene, or alkylene-arylene-alkylene, any of which is optionally substituted, and R e and R f are isocyanate groups, cyanate ester groups, thiocyanate groups, isothiocyanate groups, or epoxy groups.

12. The electrochemical cell of claim 1 , wherein the polymer layer is arranged as a protective layer, as an electrolyte, or as a separator.

13. The electrochemical cell according to claim 1 , wherein the electroactive layer comprises lithium.

14. The electrochemical cell according to claim 13 , wherein the cathode comprises elemental sulfur.

15. The electrochemical cell of claim 4 , wherein the first type of monomer is the compound

16. The electrochemical cell of claim 5 , wherein the first type of monomer is the compound

wherein n is an integer from 1 to 10.

17. The electrochemical cell of claim 7 , wherein L 3 or L 4 comprises an alkylene oxide chain comprising a copolymer of ethylene oxide and 1,2-propylene oxide.

18. The electrochemical cell of claim 10 , wherein the at least one functional group(s) reactive with a thiol group is an isocyanate group, a cyanate ester group, a thiocyanate group, a isothiocyanate group, or an epoxy group.

19. The electrochemical cell of claim 10 , wherein the third type of monomer is one of the following compounds

Assignments (3)
CONFIRMATORY ASSIGNMENT Recorded Dec 10, 2019
From: BASF SE
To: SION POWER CORPORATION
Reel/Frame 051238/0514 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 10, 2017
From: VINER, VERONIKA G.
To: SION POWER CORPORATION
Reel/Frame 041221/0657 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 10, 2017
From: FLEISCHMANN, SVEN
To: BASF SE
Reel/Frame 041221/0660 →
Continuity (2)
Provisional Application 62005667 · May 30, 2014
Related Publication 20150349310A1 · Dec 3, 2015