IP Library Granted Patent US 8,906,548
Granted Patent B2
US 8,906,548 · App. 12/899,163 · Granted Dec 9, 2014

Actinic and electron beam radiation curable electrode binders and electrodes incorporating same

Inventors: Gary E. Voelker (Bumpass, VA); John Arnold (Pittstown, NJ)
Assignees: Miltec Corporation; Actega Radcure, Inc.
H01M4/0404H01M4/13H01M4/139H01M4/621H01M4/622H01G11/86H01M4/1391H01M4/1393H01M4/625H01M10/0525Y02E60/122Y02T10/7011H01M2220/30
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Quick Facts
Patent No.
US 8,906,548
App. No.
12/899,163
Granted
Dec 9, 2014
Kind
B2
Abstract

A process for manufacturing an electrode utilizing electron beam (EB) or actinic radiation to cure electrode binding polymers is provided. A process is also disclosed for mixing specific actinic or EB radiation curable chemical precursors with electrode solid particles, application of the mixture to an electrode current collector, followed by the application of actinic or EB radiation to the current collector for curing the polymer, thereby binding the electrode material to the current collector. Lithium ion batteries, electric double layer capacitors, and components produced therefrom are also provided.

Claims (66)

1. An electrode comprising a current collector and a polymeric layer adhered to a surface of the current collector, the polymeric layer comprising a crosslinked matrix, the crosslinked matrix including a crosslink reaction product of a rubber oligomer precursor reacted with an electron beam or actinic radiation curable crosslinking agent, the rubber oligomer precursor comprising a backbone and a reactive functionality pendent to the backbone, the reactive functionality of the precursor comprising carboxy functionality, acrylate functionality, vinyl functionality, vinyl ether functionality, meth(acrylate) functionality, or epoxy functionality, the functionality of the precursor being reacted with the crosslinking agent such that the crosslinked matrix includes the crosslinking agent covalently bonded to the rubber oligomer, the crosslinked matrix being electron beam or actinic radiation cured, the polymeric layer further comprising particulate material, wherein the polymeric layer is conductive, wherein the electrode is adjacent to an additional layer, and the additional layer comprises an electrolyte.

2. The electrode according to claim 1 , wherein the rubber oligomer that is covalently bonded to crosslinking agent includes at least one of isoprene monomer units, butadiene monomer units, cyclopentadiene monomer units, ethylidene norbornene monomer units, vinyl norbornene monomer units, or combinations thereof.

3. The electrode according to claim 1 , wherein the rubber oligomer precursor is a (meth)acrylated rubber oligomer having a carboxylated isoprene backbone of the formula:

wherein m is between about 100 and about 1500, and n is between 1 and about 20.

4. The electrode according to claim 1 , wherein the rubber oligomer precursor is a (meth)acrylated rubber oligomer having a carboxylated butadiene backbone of the formula:

wherein m is between about 10 and about 1000, and n is between 1 and about 20.

5. The electrode according to claim 1 , wherein the rubber oligomer precursor is a (meth)acrylated rubber oligomer having a butadiene backbone of the formula:

wherein n is between about 5 and about 2000.

6. The electrode according to claim 1 , wherein the particulate material comprises carbon.

7. The electrode according to claim 6 , wherein the carbon is graphene, activated carbon, graphite, low sulfur graphite, carbon nanotubes, or combinations thereof.

8. The electrode according to claim 1 , wherein the particulate material comprises a metal oxide salt.

9. The electrode according to claim 1 , wherein the polymeric layer defines a thickness between about 1 and about 500 microns.

10. A battery comprising the electrode of claim 1 .

11. The battery according to claim 10 , wherein the battery is a lithium ion battery.

12. An electric double layer capacitor comprising the electrode of claim 1 .

13. The electrode according to claim 1 , wherein the crosslinking agent is a reactive diluent.

14. The electrode according to claim 1 , wherein the polymeric layer further comprises a photoinitiator.

15. An electrode comprising a current collector and a polymeric layer adhered to a surface of the current collector, the polymeric layer comprising a crosslinked matrix, the crosslinked matrix including a crosslink reaction product of a rubber oligomer precursor reacted with an electron beam or actinic radiation curable crosslinking agent, the rubber oligomer precursor comprising a backbone and a reactive functionality pendent to the backbone, the rubber oligomer precursor having a melt viscosity at 38° C. of less than about 2000 Pascal seconds, the reactive functionality of the precursor comprising carboxy functionality, acrylate functionality, vinyl functionality, vinyl ether functionality, meth(acrylate) functionality, or epoxy functionality, the functionality of the precursor being reacted with the crosslinking agent such that the crosslinked matrix includes the crosslinking agent covalently bonded to the rubber oligomer, the crosslinked matrix being electron beam or actinic radiation cured, the polymeric layer further comprising particulate material that is encapsulated within the crosslinked matrix, wherein the polymeric layer is conductive, wherein the electrode is adjacent to an additional layer, and the additional layer comprises an electrolyte.

16. The electrode according to claim 15 , wherein the rubber oligomer that is covalently bonded to crosslinking agent includes at least one of isoprene monomer units, butadiene monomer units, cyclopentadiene monomer units, ethylidene norbornene monomer units, vinyl norbornene monomer units, or combinations thereof.

17. The electrode according to claim 15 , wherein the rubber oligomer precursor is a (meth)acrylated rubber oligomer having a butadiene backbone of the formula:

wherein n is between about 5 and about 2000.

18. The electrode according to claim 15 , wherein the polymeric layer defines a thickness between about 1 and about 500 microns.

19. The electrode according to claim 15 , wherein the crosslinking agent is a reactive diluent.

20. The electrode according to claim 15 , wherein the polymeric layer further comprises a photoinitiator.

21. A battery comprising the electrode of claim 15 .

22. The battery according to claim 21 , wherein the battery is a lithium ion battery.

23. An electrode comprising a current collector and a polymeric layer adhered to a surface of the current collector, the polymeric layer comprising a crosslinked matrix, the crosslinked matrix including a crosslink reaction product of a rubber oligomer precursor reacted with an electron beam or actinic radiation curable crosslinking agent, the rubber oligomer precursor comprising a backbone and a reactive functionality pendent the backbone, the reactive functionality of the precursor comprising carboxy functionality, acrylate functionality, vinyl functionality, vinyl ether functionality, meth(acrylate) functionality, or epoxy functionality, the functionality of the precursor being reacted with the crosslinking agent such that the crosslinked matrix includes the crosslinking agent covalently bonded to the rubber oligomer, the crosslinked matrix being electron beam or actinic radiation cured, the polymeric layer further comprising particulate material, wherein the polymeric layer is conductive, wherein the particular material comprises a lithium compound.

24. The electrode according to claim 23 , wherein the rubber oligomer that is covalently bonded to crosslinking agent includes at least one of isoprene monomer units, butadiene monomer units, cyclopentadiene monomer units, ethylidene norbornene monomer units, vinyl norbornene monomer units, or combinations thereof.

25. The electrode according to claim 23 , wherein the rubber oligomer precursor is a (meth)acrylated rubber oligomer having a butadiene backbone of the formula:

wherein n is between about 5 and about 2000.

26. The electrode according to claim 23 , wherein the electrode is adjacent to an additional layer.

27. The electrode according to claim 26 , wherein the additional layer is a second electrode or a separator.

28. The electrode according to claim 26 , wherein the additional layer comprises an electrolyte.

29. The electrode according to claim 23 , wherein the polymeric layer defines a thickness between about 1 and about 500 microns.

30. A battery comprising the electrode of claim 23 .

31. The battery according to claim 30 , wherein the battery is a lithium ion battery.

32. An electrode comprising a current collector and a polymeric layer adhered to a surface of the current collector, the polymeric layer comprising a crosslinked matrix, the crosslinked matrix including a crosslink reaction product of a rubber oligomer precursor reacted with an electron beam or actinic radiation curable crosslinking agent, the rubber oligomer precursor comprising a backbone and a reactive functionality pendent the backbone, the rubber oligomer precursor having a melt viscosity at 38° C. of less than about 2000 Pascal seconds, the reactive functionality of the precursor comprising carboxy functionality, acrylate functionality, vinyl functionality, vinyl ether functionality, meth(acrylate) functionality, or epoxy functionality, the functionality of the precursor being reacted with the crosslinking agent such that the crosslinked matrix includes the crosslinking agent covalently bonded to the rubber oligomer, the crosslinked matrix being electron beam or actinic radiation cured, the polymeric layer further comprising particulate material that is encapsulated within the crosslinked matrix, the particulate material comprising a lithium compound, wherein the polymeric layer is conductive.

33. The electrode according to claim 32 , wherein the rubber oligomer that is covalently bonded to crosslinking agent includes at least one of isoprene monomer units, butadiene monomer units, cyclopentadiene monomer units, ethylidene norbornene monomer units, vinyl norbornene monomer units, or combinations thereof.

34. The electrode according to claim 32 , wherein the rubber oligomer precursor is a (meth)acrylated rubber oligomer having a butadiene backbone of the formula:

wherein n is between about 5 and about 2000.

35. The electrode according to claim 32 , wherein the electrode is adjacent to an additional layer.

36. The electrode according to claim 35 , wherein the additional layer is a second electrode or a separator.

37. The electrode according to claim 35 , wherein the additional layer comprises an electrolyte.

38. The electrode according to claim 32 , wherein the polymeric layer defines a thickness between about 1 and about 500 microns.

39. The electrode according to claim 32 , wherein the crosslinking agent is a reactive diluent.

40. The electrode according to claim 32 , wherein the polymeric layer further comprises a photoinitiator.

41. A battery comprising the electrode of claim 32 .

42. The battery according to claim 32 , wherein the battery is a lithium ion battery.

43. A battery comprising an electrode, the electrode of the battery comprising a current collector and a polymeric layer adhered to a surface of the current collector, the polymeric layer comprising a crosslinked matrix, the crosslinked matrix including a crosslink reaction product of a rubber oligomer precursor reacted with an electron beam or actinic radiation curable crosslinking agent, the rubber oligomer precursor comprising a backbone and a reactive functionality pendent the backbone, the reactive functionality of the precursor comprising carboxy functionality, acrylate functionality, vinyl functionality, vinyl ether functionality, meth(acrylate) functionality, or epoxy functionality, the functionality of the precursor being reacted with the crosslinking agent such that the crosslinked matrix includes the crosslinking agent covalently bonded to the rubber oligomer, the crosslinked matrix being electron beam or actinic radiation cured, the polymeric layer further comprising particulate material, wherein the polymeric layer is conductive.

44. The battery according to claim 43 , wherein the rubber oligomer that is covalently bonded to crosslinking agent includes at least one of isoprene monomer units, butadiene monomer units, cyclopentadiene monomer units, ethylidene norbornene monomer units, vinyl norbornene monomer units, or combinations thereof.

45. The battery according to claim 43 , wherein the rubber oligomer precursor is a (meth)acrylated rubber oligomer having a butadiene backbone of the formula:

wherein n is between about 5 and about 2000.

46. The battery according to claim 43 , wherein the electrode is adjacent to an additional layer.

47. The battery according to claim 46 , wherein the additional layer is a second electrode or a separator.

48. The battery according to claim 43 , wherein the polymeric layer defines a thickness between about 1 and about 500 microns.

49. The battery according to claim 43 , wherein the battery is a lithium ion battery.

50. A battery comprising an electrode, the electrode of the battery comprising a current collector and a polymeric layer adhered to a surface of the current collector, the polymeric layer comprising a crosslinked matrix, the crosslinked matrix including a crosslink reaction product of a rubber oligomer precursor reacted with an electron beam or actinic radiation curable crosslinking agent, the rubber oligomer precursor comprising a backbone and a reactive functionality pendent the backbone, the rubber oligomer precursor having a melt viscosity at 38° C. of less than about 2000 Pascal seconds, the reactive functionality of the precursor comprising carboxy functionality, acrylate functionality, vinyl functionality, vinyl ether functionality, meth(acrylate) functionality, or epoxy functionality, the functionality of the precursor being reacted with the crosslinking agent such that the crosslinked matrix includes the crosslinking agent covalently bonded to the rubber oligomer, the crosslinked matrix being electron beam or actinic radiation cured, the polymeric layer further comprising particulate material that is encapsulated within the crosslinked matrix, wherein the polymeric layer is conductive.

51. The battery according to claim 50 , wherein the rubber oligomer that is covalently bonded to crosslinking agent includes at least one of isoprene monomer units, butadiene monomer units, cyclopentadiene monomer units, ethylidene norbornene monomer units, vinyl norbornene monomer units, or combinations thereof.

52. The battery according to claim 50 , wherein the rubber oligomer precursor is a (meth)acrylated rubber oligomer having a butadiene backbone of the formula:

wherein n is between about 5 and about 2000.

53. The battery according to claim 50 , wherein the electrode is adjacent to an additional layer.

54. The battery according to claim 53 , wherein the additional layer is a second electrode or a separator.

55. The battery according to claim 50 , wherein the polymeric layer defines a thickness between about 1 and about 500 microns.

56. The battery according to claim 50 , wherein the crosslinking agent is a reactive diluent.

57. The battery according to claim 50 , wherein the polymeric layer further comprises a photoinitiator.

58. The battery according to claim 50 , wherein the battery is a lithium ion battery.

Assignments (4)
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS Recorded Jun 26, 2015
From: USB AG, STAMFORD BRANCH, AS COLLATERAL AGENT
To: DUCOMMUN AEROSTRUCTURES, INC.; DUCOMMUN TECHNOLOGIES, INC. (N/K/A DUCOMMUN LABARGE TECHNOLOGIES, INC.); MILTEC CORPORATION; DUCOMMUN LABARGE TECHNOLOGIES, INC.
Reel/Frame 036020/0476 →
PATENT SECURITY AGREEMENT Recorded Jun 29, 2011
From: MILTEC CORPORATION
To: UBS AG, STAMFORD BRANCH, AS COLLATERAL AGENT
Reel/Frame 026524/0608 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 16, 2010
From: ARNOLD, JOHN
To: ACTEGA RADCURE, INC.
Reel/Frame 025499/0049 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 15, 2010
From: VOELKER, GARY E.
To: MILTEC CORPORATION
Reel/Frame 025505/0063 →
Continuity (2)
Provisional Application 61249382 · Oct 7, 2009
Related Publication 20110081575A1 · Apr 7, 2011