IP Library › Granted Patent US 12,291,592
Granted Patent B2
US 12,291,592 · App. 17/980,792 · Granted May 6, 2025

Ion-conducting bio-based polymers from raw lignocellulosic biomass

Inventors: Thomas H. Epps, III (Bear, DE); Angela L. Holmberg (Somerville, MA); Kaleigh H. Nicastro (Newark, DE); Shu Wang (Newark, DE); Basudeb Saha (Newark, DE); Li Shuai (Blacksburg, VA); Dionisios G. Vlachos (Newark, DE); Melody A. Morris (Elkton, MD)
Assignee: University Of Delaware
C08F293/005B32B27/302B32B27/308C07C41/18C07C41/38C07C67/14C07C69/618C08G83/005C09J7/38C09J7/385C09J7/387C09J9/02C09J125/18C09J133/08C09J153/00H01M4/622H01M10/0565C08F212/24C08F220/1806C08F2438/01C08G2170/40C08H8/00C09J2203/33C09J2301/414C09J2400/163C09J2400/226C09J2400/283C09J2433/00C09J2453/00C09J2471/00C09J2497/00H01M2300/0082
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Quick Facts
Patent No.
US 12,291,592
App. No.
17/980,792
Granted
May 6, 2025
Kind
B2
Abstract

Disclosed herein is a bio-based copolymer comprising in polymerized form (i) at least one polymerizable bio-based monomer containing one phenolic hydroxyl group which has been derivatized to provide at least one polymerizable functional group which is an ethylenically unsaturated functional group (such as a [meth]acrylate group), where the precursors of the polymerizable bio-based monomers are derived from raw lignin-containing biomass, and (ii) at least one ion-conducting co-monomer other than the bio-based monomer. Also disclosed herein are binders comprising the bio-based copolymer, electrodes comprising the binder, polymer electrolytes comprising the bio-based copolymer and an electrochemical device comprising an electrode in electrical contact with a polymer electrolyte, wherein at least one of the electrode and the polymer electrolyte comprises the bio-based copolymer.

Claims (44)

1. A bio-based polymer comprising:

(i) at least one bio-based polymeric block, the at least one bio-based polymeric block comprising: at least one bio-based monomer having a structure corresponding to formula (II):

wherein R 1 is hydrogen, methyl, ethyl, n-propyl, i-propyl, propylene, formyl, a propanoate salt, a propanoate ester, an acetate salt, or an acetate ester,

wherein R 2 is a substituent comprised of at least one polymerizable functional group which is an ethylenically unsaturated functional group, and

wherein R 3 and R 4 are independently selected from hydrogen or methoxy,

wherein at least one of R 1 , R 3 , and R 4 is not hydrogen; and

(ii) at least one ion-conducting, co-monomer-based polymeric block,

wherein the at least one ion-conducting co-monomer-based polymeric block comprises a poly((oligo-oxyethylene) [meth]acrylate) block, and wherein the bio-based polymer is a diblock, bio-based polymer having the following structure (III) or a triblock polymer having the following structure (IV):

wherein x is in the range of 2-1000; n in the range of 10-500; and m in the range of 10-1000; R 1 is hydrogen, methyl, ethyl, n-propyl, i-propyl, propylene, formyl, a propanoate salt, a propanoate ester, an acetate salt, or an acetate ester; and R 3 and R 4 are independently selected from hydrogen or methoxy.

2. A binder for a battery comprising the bio-based polymer of claim 1 .

3. An electrode comprising the binder of claim 2 and an electrode active material.

4. A polymer electrolyte comprising the bio-based polymer of claim 1 and at least one salt.

5. The polymer electrolyte of claim 4 , wherein the at least one salt comprises at least one lithium salt selected from the group consisting of LiBr, LiCl, LiClO 4 , LiPF 6 , LiAsF 6 , LiSbF 6 , LiBF 4 , LiCF 3 SO 3 , LiN(FSO 2 ) 2 , LiN(CF 3 SO 2 ) 2 , LiN(C 2 F 5 SO 2 ) 2 , LiC 6 F 3 N 4 , LiC(CF 3 SO 2 ) 3 , Li 2 B 10 Cl 10 , LiB(OCH 3 ) 4 , LiB(C 2 O 4 ) 2 , LiB(CN) 4 , LiBC 2 O 4 F 2 , LiB(C 3 O 4 F) 2 , lithium acetate, and LiAlCl 4 .

6. An electrochemical device comprising an electrode in electrical contact with a polymer electrolyte, wherein at least one of the electrode and the polymer electrolyte comprises the bio-based copolymer polymer of claim 1 .

7. A bio-based polymer comprising in polymerized form:

(i) at least one bio-based monomer having a structure corresponding to formula (II):

wherein R 1 is hydrogen, methyl, ethyl, n-propyl, i-propyl, propylene, formyl, a propanoate salt, a propanoate ester, an acetate salt, or an acetate ester,

wherein R 2 is a substituent comprised of at least one polymerizable functional group which is an ethylenically unsaturated functional group, and

wherein R 3 and R 4 are independently selected from hydrogen or methoxy,

wherein at least one of R 1 , R 3 , and R 4 is not hydrogen; and

(ii) at least one ion-conducting co-monomer other than the bio-based monomer,

wherein the at least one ion-conducting co-monomer is a co-polymerizable co-monomer comprising at least one of (oligo-oxyethylene) [meth]acrylate, styrene trifluoromethanesulfonylimide lithium salt, 1-(3-(methacryloyloxy)-propylsulfonyl)-1-(trifluoromethylsulfonyl) imide lithium salt, and 3-sulfopropyl methacrylate lithium salt, and wherein the bio-based polymer is a random, statistical, graft, star, brush, block, or cyclic copolymer.

8. A binder for a battery comprising the bio-based polymer of claim 7 .

9. An electrode comprising the binder of claim 8 and an electrode active material.

10. A polymer electrolyte comprising the bio-based polymer of claim 7 and at least one salt.

11. The polymer electrolyte of claim 10 , wherein the at least one salt comprises at least one lithium salt selected from the group consisting of LiBr, LiCl, LiClO 4 , LiPF 6 , LiAsF 6 , LiSbF 6 , LiBF 4 , LiCF 3 SO 3 , LiN(FSO 2 ) 2 , LiN(CF 3 SO 2 ) 2 , LiN(C 2 F 5 SO 2 ) 2 , LiC 6 F 3 N 4 , LiC(CF 3 SO 2 ) 3 , Li 2 B 10 Cl 10 , LiB(OCH 3 ) 4 , LiB(C 2 O 4 ) 2 , LiB(CN) 4 , LiBC 2 O 4 F 2 , LiB(C 3 O 4 F) 2 , lithium acetate, and LiAlCl 4 .

12. An electrochemical device comprising an electrode in electrical contact with a polymer electrolyte, wherein at least one of the electrode and the polymer electrolyte comprises the bio-based polymer of claim 5 .

13. A bio-based polymer comprising in polymerized form:

(i) at least one bio-based monomer having a structure corresponding to formula (II):

wherein R 1 is hydrogen, methyl, ethyl, n-propyl, i-propyl, propylene, formyl, a propanoate salt, a propanoate ester, an acetate salt, or an acetate ester,

wherein R 2 is a substituent comprised of at least one polymerizable functional group which is an ethylenically unsaturated functional group, and

wherein R 3 and R 4 are independently selected from hydrogen or methoxy,

wherein at least one of R 1 , R 3 , and R 4 is not hydrogen; and

(ii) at least one ion-conducting, co-monomer other than the bio-based monomer

wherein the at least one bio-based monomer comprises:

(i) a phenol [meth]acrylate selected from the group consisting of cresol [meth]acrylate, 4-ethylphenol [meth]acrylate, 4-propylphenol [meth]acrylate, 4-hydroxybenzaldehyde [meth]acrylate, and 3-(4-hydroxyphenol) propanoate [meth]acrylate;

(ii) a monomethoxyphenol [meth]acrylate selected from the group consisting of guaiacol (monomethoxy-substituted phenol) [meth]acrylate, 4-ethylguaiacol [meth]acrylate, creosol [meth]acrylate, 4-propylguaiacol [meth]acrylate, vanillin [meth]acrylate, and methyl homovanillate [meth]acrylate (methyl 2-(4-hydroxy-3-methoxyphenyl) acetate [meth]acrylate);

(iii) a dimethoxyphenol [meth]acrylate selected from the group consisting of syringol (dimethoxy-substituted phenol) [meth]acrylate, 4-methylsyringyl[meth]acrylate, 4-ethylsyringyl[meth]acrylate, 4-n-propylsyringyl[meth]acrylate, 4-i-propylsyringyl[meth]acrylate, 4-propylenesyringyl[meth]acrylate, 4-formylsyringyl[meth]acrylate, 4-propanoatesyringyl[meth]acrylate salt, 4-propanoatesyringyl[meth]acrylate ester, 4-acetatesyringyl[meth]acrylate salt, and 4-acetatesyringyl[meth]acrylate ester; or

(iv) combinations thereof.

14. A binder for a battery comprising the bio-based polymer of claim 13 .

15. An electrode comprising the binder of claim 14 and an electrode active material.

16. A polymer electrolyte comprising the bio-based polymer of claim 13 and at least one salt.

17. The polymer electrolyte of claim 16 , wherein the at least one salt comprises at least one lithium salt selected from the group consisting of LiBr, LiCl, LiClO 4 , LiPF 6 , LiAsF 6 , LiSbF 6 , LiBF 4 , LiCF 3 SO 3 , LiN(FSO 2 ) 2 , LiN(CF 3 SO 2 ) 2 , LiN(C 2 F 5 SO 2 ) 2 , LiC 6 F 3 N 4 , LiC(CF 3 SO 2 ) 3 , Li 2 B 10 Cl 10 , LiB(OCH 3 ) 4 , LiB(C 2 O 4 ) 2 , LiB(CN) 4 , LiBC 2 O 4 F 2 , LiB(C 3 O 4 F) 2 , lithium acetate, and LiAlCl 4 .

18. An electrochemical device comprising an electrode in electrical contact with a polymer electrolyte, wherein at least one of the electrode and the polymer electrolyte comprises the bio-based polymer of claim 11 .

Assignments (2)
CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNEE ADDRESS PREVIOUSLY RECORDED AT REEL: 63149 FRAME: 775. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Jul 10, 2023
From: EPPS, THOMAS H., III; HOLMBERG, ANGELA L.; NICASTRO, KALEIGH H.; WANG, SHU; SAHA, BASUDEB; SHUAI, LI; VLACHOS, DIONISIOS G.; MORRIS, MELODY A.
To: UNIVERSITY OF DELAWARE
Reel/Frame 064237/0663 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 23, 2023
From: EPPS, III, THOMAS H.; HOLMBERG, ANGELA L.; NICASTRO, KALEIGH H.; WANG, SHU; SAHA, BASUDEB; SHUAI, LI; VLACHOS, DIONISIOS G.; MORRIS, MELODY A.
To: UNIVERSITY OF DELAWARE
Reel/Frame 063149/0775 →
Continuity (6)
Division 16243718 · Jan 9, 2019
Continuation In Part 15208135 · Jul 12, 2016
Provisional Application 62713571 · Aug 2, 2018
Provisional Application 62615040 · Jan 9, 2018
Provisional Application 62191551 · Jul 13, 2015
Related Publication 20230113164A1 · Apr 13, 2023
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