Freestanding ion gel and method for preparing the same

Patent metadata

Field	Value
Publication number	US-11623971-B2
Application number	US-202016997254-A
Country	US
Kind code	B2
Filing date	Aug 19, 2020
Priority date	Aug 23, 2019
Publication date	Apr 11, 2023
Grant date	Apr 11, 2023

Abstract

Disclosed is preparation of a freestanding ion gel having high stability and high ionic conductivity based on surface-activity ionic liquids. Further, disclosed is a solid electrolyte using the ion gel. A method for preparing the freestanding ion gel include mixing a surface-activity ionic liquid having an alkyl group having 8 or greater carbon atoms, a crosslinking agent, water and oil with each other to form a bicontinuous microemulsion mixture; ii) adding an initiator to the mixture; and iii) curing the mixture using ultraviolet (UV) or thermal energy to form a freestanding ion gel.

First claim

What is claimed is:

1. A method for preparing a freestanding ion gel, the method comprising:
i) mixing a surface-activity ionic liquid having an alkyl group having 8 or greater carbon atoms, a crosslinking agent, water and oil with each other to form a bicontinuous microemulsion mixture;
ii) adding an initiator to the mixture; and
iii) curing the mixture using ultraviolet (UV) or thermal energy to form a freestanding ion gel,
wherein the surface-activity ionic liquid includes a combination of a cation and an anion, and
wherein the anion is selected from the group consisting of hexafluoroantimonate; methylsulfate; ethylsulfate; acetate; and bis(trifluoromethylsulfonyl)amide.

2. The method of claim 1 , wherein i) further includes adding a surfactant to the mixture.

3. The method of claim 1 , wherein the bicontinuous microemulsion mixture forms a percolation structure in which all of ion conductive domains are connected to each other.

4. The method of claim 1 ,
wherein the cation is selected from the group consisting of an imidazolium-based cation; a pyridinium-based cation; a piperidinium-based cation; a pyrrolidinium-based cation; an ammonium-based cation; a phosphonium-based cation; and a sulfonium-based cation.

5. The method of claim 1 , wherein the crosslinking agent is selected from the group consisting of di(ethylene glycol) dimethacrylate; di(trimethylolpropane) tetraacrylate; divinylbenzene; ethylene glycol dimethacrylate; trimethylolpropane triacrylate;
trimethylolpropane ethoxylate triacrylate; 1,3-butanediol diacrylate 1,4-butanediol diacrylate; 1,3-butanediol dimethacrylate; 1,4-butanediol dimethacrylate; 1,6-hexanediol dimethacrylate; 1,6-hexanediol diacrylate; 1,6-hexanediol ethoxylate diacrylate; 1,10-decanediol dimethacrylate; 1,4-phenylene dimethacrylate; glycerol 1,3-diglycerolate diacrylate; neopentyl glycol diacrylate; and N, N′-methylenebiscacrylamide.

6. The method of claim 1 , wherein i) further includes adding, to the mixture, a polymerizable ionic liquid having a functional group introduced thereto, thereby to improve mechanical strength of the freestanding ion gel.

7. The method of claim 4 , wherein the polymerizable ionic liquid having the functional group introduced thereto includes a combination of a cation and an anion,
wherein the cation is selected from the group consisting of 1-(2-acryloyloxyundecyl)-3-methylimidazolium; 1-methyl-3-(undec-10-enyl)-imidazolium; 1-(11-acryloyloxyundecyl)-1-methylpyrrolidinium; and 3-(11-acryloyloxyundecyl)-1-ethyl-2-phenyl-imidazolium.

8. The method of claim 1 , wherein the initiator includes a photo-initiator or a thermal-initiator,
wherein the photo-initiator is selected from the group consisting of 2-hydroxy-2-methylpropiophenone; 2-hydroxy-4′-hydroxyethoxy-2-methylpropiophenone; 1-hydroxycyclohexyl phenyl ketone; 2,2-dimethoxy-2-phenylacetophenone; 2,2-diethoxyacetophenone; 1-hydroxycyclohexyl phenyl ketone; benzophenone; 2-benzyl-2-(dimethylamino)-1-4-(4-morpholinyl)phenyl-1-butanone; diphenyl(2,4,6-trimethylbenzoyl)-phosphine oxide; 2,4,6-trimethylbenzoyl diphenylphosphine oxide; 2,4,6-trimethylbenzoyl-diphenyl phosphinate; and bis(2,4,6-trimethylbenzoyl)-phenyl phosphineoxide, and
wherein the thermal-initiator is selected from the group consisting of dibenzoyl peroxide; succinic acid peroxide; dilauroyl peroxide; didecanoyl peroxide; t-amyl peroxypivalate; t-butyl peroxypivalate; 2,5-dimethyl-2.5 bis(2-ethyl-hexanoylper oxy) hexane; dibenzoyl peroxide; 4,4′-azobis(4-cyanovaleric acid), 1,1′-azobis(cyclohexane carbonitrile), azobisisobutyronitrile; and 2,2′-azobis (2-methylpropionamidine)dihydrochloride.

9. A freestanding ion gel prepared using the method of claim 1 .

10. A solid electrolyte containing a freestanding ion gel prepared using the method of claim 1 .

11. A method for preparing a freestanding ion gel, the method comprising:
i) mixing 1-tetradecyl-3-methylimidazolium chloride as a surface-activity ionic liquid, 6-hexanediol diacrylate as a crosslinking agent, 1-butanol, 1-octene as an oil, and water with each other to form a bicontinuous microemulsion mixture;
ii) adding 2-hydroxy-2-methylpropiophenone as a photo-initiator to the mixture; and
iii) curing the mixture using ultraviolet (UV) curing to form a freestanding ion gel.

12. The method of claim 11 , wherein i) further includes adding, to the mixture, a polymerizable ionic liquid having a functional group introduced thereto, thereby to improve mechanical strength of the freestanding ion gel, wherein the polymerizable ionic liquid having the functional group introduced thereto includes 1-(2-acryloyloxyundecyl)-3-methylimidazolium bromide.

13. A method for preparing a freestanding ion gel, the method comprising:
i) mixing a surface-activity ionic liquid having an alkyl group having 8 or greater carbon atoms, a crosslinking agent, water and oil with each other to form a bicontinuous microemulsion mixture;
ii) adding an initiator to the mixture; and
iii) curing the mixture using ultraviolet (UV) or thermal energy to form a freestanding ion gel,
wherein the surface-activity ionic liquid includes a combination of a cation and an anion, and
wherein the cation is selected from the group consisting of 1-(11-acryloyloxyundecyl)-1-methylpyrrolidinium; and 3-(11-acryloyloxyundecyl)-1-ethyl-2-phenyl-imidazolium.

14. The method of claim 13 , wherein i) further includes adding a surfactant to the mixture.

15. The method of claim 13 , wherein the anion is selected from the group consisting of chloride; bromide; iodide; hexafluorophosphate; tetrafluoroborate; hexafluoroantimonate; trifluoromethanesulfonate; methylsulfate; ethylsulfate; acetate; thiocyanate; dicyanamide; and bis(trifluoromethylsulfonyl)amide.

16. The method of claim 13 , wherein the crosslinking agent is selected from the group consisting of di(ethylene glycol) dimethacrylate; di(trimethylolpropane) tetraacrylate; divinylbenzene; ethylene glycol dimethacrylate; trimethylolpropane triacrylate; trimethylolpropane ethoxylate triacrylate; 1,3-butanediol diacrylate 1,4-butanediol diacrylate; 1,3-butanediol dimethacrylate; 1,4-butanediol dimethacrylate; 1,6-hexanediol dimethacrylate; 1,6-hexanediol diacrylate; 1,6-hexanediol ethoxylate diacrylate; 1,10-decanediol dimethacrylate; 1,4-phenylene dimethacrylate; glycerol 1,3-diglycerolate diacrylate; neopentyl glycol diacrylate; and N, N′-methylenebiscacrylamide.

17. The method of claim 13 , wherein i) further includes adding, to the mixture, a polymerizable ionic liquid having a functional group introduced thereto, thereby to improve mechanical strength of the freestanding ion gel.

18. The method of claim 13 , wherein the initiator includes a photo-initiator or a thermal-initiator,
wherein the photo-initiator is selected from the group consisting of 2-hydroxy-2-methylpropiophenone; 2-hydroxy-4′-hydroxyethoxy-2-methylpropiophenone; 1-hydroxycyclohexyl phenyl ketone; 2,2-dimethoxy-2-phenylacetophenone; 2,2-diethoxyacetophenone; 1-hydroxycyclohexyl phenyl ketone; benzophenone; 2-benzyl-2-(dimethylamino)-1-4-(4-morpholinyl)phenyl-1-butanone; diphenyl(2,4,6-trimethylbenzoyl)-phosphine oxide; 2,4,6-trimethylbenzoyl diphenylphosphine oxide; 2,4,6-trimethylbenzoyl-diphenyl phosphinate; and bis(2,4,6-trimethylbenzoyl)-phenyl phosphineoxide,
wherein the thermal-initiator is selected from the group consisting of dibenzoyl peroxide; succinic acid peroxide; dilauroyl peroxide; didecanoyl peroxide; t-amyl peroxypivalate; t-butyl peroxypivalate; 2,5-dimethyl-2.5 bis(2-ethyl-hexanoylper oxy) hexane; dibenzoyl peroxide; 4,4′-azobis(4-

Assignees

• Research & Business Found Sungkyunkwan Univ
• Kunsan National Univ Industry Univ Cooperation Foundation

Inventors

• Yi Gi Ra
• Lee Min Jae
• Kang Tae Hui
• Ahn Yeon Ho
• Kim Duk Joon

Classifications

• C08K5/20

  Carboxylic acid amides · CPC title

• C08F222/102 Primary

  of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate · CPC title

• C08K5/3445

  Five-membered rings · CPC title

• C08J3/075 Primary

  Macromolecular gels · CPC title

• C08K5/06

  Ethers; Acetals; Ketals; Ortho-esters · CPC title