Polymeric ionic liquid and process for producing a polymer membrane including the same

Patent metadata

Field	Value
Publication number	US-9893380-B2
Application number	US-201514867946-A
Country	US
Kind code	B2
Filing date	Sep 28, 2015
Priority date	Sep 28, 2015
Publication date	Feb 13, 2018
Grant date	Feb 13, 2018

Abstract

A polymeric ionic liquid has a formula (I),

where A 1 , A 2 , B, k, Q, and Z are as defined in the specification. An intermediate polymer for making the polymeric ionic liquid, a process for producing the polymeric ionic liquid, a process for producing a polymer membrane including the polymeric ionic liquid, a process for preparing a gel polymer electrolyte including the polymer membrane, and a binder including the polymeric ionic liquid are also disclosed.

First claim

What is claimed is:

1. A polymeric ionic liquid having a formula (I) for use as an electrolyte

where:
Q is

k is an integral greater than zero;
B is

Z is alkyl or a hydrogen atom when each of B and Q is —CH 2 —, and
Z is

when B is

 and
A 1 and A 2 are independently selected for each repeating unit, wherein A 1 and A 2 are independently alkyl or a hydrogen atom when B is

 and
wherein A 1 and A 2 are independently

when each of B and Q is —CH 2 —,
with the proviso that in at least one repeating unit, at least one of A 1 and A 2 is not

with the proviso that when A 1 is

A 2 is not

 and
with the proviso that when A 1 is

A 2 is not

in which g is an integral not less than 1,
Y − is PF 6 − , BF 4 − ,

 ClO 4 − , or a halide anion,
Y 1 is a halogen atom,
and X + is

in which R, R′, R″, R′″ are each independently —CH 3 , —CH 2 CH 3 , —CH 2 CH 2 CH 3 , —CH 2 CH 2 CH 2 CH 3 , —CH 2 CH 2 OCH 3 , or —CH 2 CH 2 OCH 2 CH 2 OCH 3 .

2. The polymeric ionic liquid according to claim 1 , wherein Q is

3. The polymeric ionic liquid according to claim 2 , wherein each of B and Q is —CH 2 —, A 1 and A 2 being independently

and
Z being a hydrogen atom.

4. A process for producing a polymeric ionic liquid according to claim 1 , comprising the steps of:
(a) preparing a phenolic epoxy resin having a formula (III)

where
Q is

k is an integral greater than zero,
B is

A″ is alkyl or a hydrogen atom when B is

 and is

 when each of B and Q is —CH 2 —, in which g is an integral not less than 1, and
Z″ is alkyl or a hydrogen atom when each of B and Q is —CH 2 —, and is

 when B is

 and
(b) subjecting the phenolic epoxy resin to a ring opening reaction using a first compound which is selected from the group consisting of hydrogen halide, substituted or non-substituted pyridine, substituted or non-substituted imidazole, substituted or non-substituted piperidine, substituted or non-substituted pyrrolidine, tertiary amine, tertiary phosphine, and combinations thereof.

5. The process according to claim 4 , wherein in step (b), the first compound is hydrogen halide, and is used in the ring opening reaction to thereby obtain an intermediate polymer, the process further comprising the step (c) of reacting the intermediate polymer with a second compound to obtain a polymeric ionic liquid precursor, the second compound being selected from the group consisting of substituted or non-substituted pyridine, substituted or non-substituted imidazole, substituted or non-substituted piperidine, substituted or non-substituted pyrrolidine, tertiary amine, tertiary phosphine, and combinations thereof.

6. The process according to claim 5 , further comprising the step (d) of subjecting the polymeric ionic liquid precursor to an anion replacement reaction using an alkali metal salt so as to obtain a polymeric ionic liquid.

7. The process according to claim 6 , wherein the alkali metal salt is selected from the group consisting of potassium hexafluorophosphate (KPF 6 ), bis(trifluoromethane)sulfonimide lithium salt (LiTFSI), lithium tetrafluoroborate (LiBF 4 ), dodecylbenzene sulfonic acid sodium salt (NaDBSA), lithium trifluoromethanesulfonate (LiCF 3 SO 3 ), and combinations thereof.

8. The process according to claim 7 , wherein the alkali metal salt is potassium hexafluorophosphate (KPF 6 ) or bis(trifluoromethane)sulfonimide lithium salt (LiTFSI).

9. A process for preparing a gel polymer electrolyte, comprising a step of soaking a polymer membrane including the polymeric ionic liquid as claimed in claim 1 , with a lithium-ion containing electrolyte.

10. The process according to claim 9 , wherein the lithium-ion containing electrolyte includes lithium hexafluorophosphate.

11. A binder for a lithium battery electrode, comprising the polymeric ionic liquid as claimed in claim 1 .

Assignees

• Univ Nat Cheng Kung
• Rising Chemical Co Ltd

Inventors

• Kuo Ping Lin
• Chen Szu Ting
• Hsu Huang Ming
• Tsao Chih Hao
• Hsu Chun Han
• Chien Li Hsuan

Classifications

• H01M4/622

  being polymers · CPC title

• H01M10/0568

  characterised by the solutes · CPC title

• C08G59/02

  Polycondensates containing more than one epoxy group per molecule · CPC title

• B01J41/13

  obtained otherwise than by reactions only involving unsaturated carbon-to-carbon bonds · CPC title

• H01M10/0565 Primary

  Polymeric materials, e.g. gel-type or solid-type · CPC title