Method for producing semiconducting single-walled carbon nanotube dispersion

Patent metadata

Field	Value
Publication number	US-12006218-B2
Application number	US-202017776738-A
Country	US
Kind code	B2
Filing date	Nov 13, 2020
Priority date	Nov 15, 2019
Publication date	Jun 11, 2024
Grant date	Jun 11, 2024

Abstract

In one aspect, provided is a method for producing a semiconducting single-walled carbon nanotube dispersion. This method allows semiconducting single-walled carbon nanotubes to be separated from a single-walled carbon nanotube mixture containing semiconducting single-walled carbon nanotubes and metallic single-walled carbon nanotubes in an aqueous medium, and yet requires only an easily available separation agent and a simple operation.
One aspect of the present disclosure relates to a method for producing a semiconducting single-walled carbon nanotube dispersion. The method includes (A) preparing a single-walled carbon nanotube dispersion to be separated that contains single-walled carbon nanotubes composed of semiconducting single-walled carbon nanotubes and metallic single-walled carbon nanotubes, an aqueous medium, and a copolymer containing a constitutional unit A derived from a monomer represented by the following formula (1) and a constitutional unit B derived from a monomer represented by the following formula (3), and (B) centrifuging the single-walled carbon nanotube dispersion to be separated and then collecting a supernatant containing the semiconducting single-walled carbon nanotubes from the centrifuged single-walled carbon nanotube dispersion

CH 2 ═CH—COOM  (1)

CH 2 ═CR 5 —COO—(CH 2 CH 2 O) q —H  (3).

First claim

The invention claimed is:

1. A method for producing a semiconducting single-walled carbon nanotube dispersion, comprising:
(A) preparing a single-walled carbon nanotube dispersion to be separated that contains single-walled carbon nanotubes composed of semiconducting single-walled carbon nanotubes and metallic single-walled carbon nanotubes, an aqueous medium, and a copolymer containing a constitutional unit A derived from a monomer represented by the following formula (1) and a constitutional unit B derived from a monomer represented by the following formula (3); and
(B) centrifuging the single-walled carbon nanotube dispersion to be separated and then collecting a supernatant containing the semiconducting single-walled carbon nanotubes from the centrifuged single-walled carbon nanotube dispersion,
CH 2 ═CH—COOM  (1)

where M represents a hydrogen atom, a metal atom, or a group with a structure represented by the following formula (2):

where R 1 , R 2 , R 3 , and R 4 each independently represent a hydrogen atom or an alkyl group having 1 to 2 carbon atoms and optionally containing a hydroxyl group,
CH 2 ═CR 5 —COO—(CH 2 CH 2 O) q —H  (3)

where R 5 represents a hydrogen atom or a methyl group, and q represents an average number of moles of an ethyleneoxy group added and is 2 to 120.

2. The method for producing a semiconducting single-walled carbon nanotube dispersion according to claim 1 , wherein a content of the constitutional unit A in all constitutional units of the copolymer is 55 mol % or more and less than 100 mol %.

3. The method for producing a semiconducting single-walled carbon nanotube dispersion according to claim 1 , wherein a content of the constitutional unit B in all constitutional units of the copolymer is more than 0 mol % and 45 mol % or less.

4. The method for producing a semiconducting single-walled carbon nanotube dispersion according to claim 1 , wherein a total content of the constitutional unit A and the constitutional unit B in all constitutional units of the copolymer is 80 mol % or more and 100 mol % or less.

5. The method for producing a semiconducting single-walled carbon nanotube dispersion according to claim 1 , wherein a molar ratio (A/B) of the constitutional unit A to the constitutional unit B in the copolymer is 1.2 or more and 300 or less.

6. The method for producing a semiconducting single-walled carbon nanotube dispersion according to claim 1 , wherein an average diameter of the single-walled carbon nanotubes used for preparing the single-walled carbon nanotube dispersion to be separated in the process (A) is 0.5 nm or more and 2 nm or less.

7. The method for producing a semiconducting single-walled carbon nanotube dispersion according to claim 1 , wherein separability of the semiconducting single-walled carbon nanotubes in the supernatant obtained in the process (B) is 1.3 or more, and
the separability of the semiconducting single-walled carbon nanotubes (semiconducting SWCNTs) is a value determined by the following formula

I
S

(

peak
⁢

intensity
⁢

of
⁢

absorption
⁢

wavelength

specific
⁢

to
⁢

semiconducting
⁢

SWCNTs

)

I
M

(

peak
⁢

intensity
⁢

of
⁢

absorption
⁢

wavelength

specific
⁢

to
⁢

metallic
⁢

SWCNTs

)

=

Separability
⁢

of
⁢

semiconducting
⁢

SWCNTs
.

8. A method for producing semiconducting single-walled carbon nanotubes, comprising:
filtering the semiconducting single-walled carbon nanotube dispersion obtained by the method according to claim 1 and collecting the semiconducting single-walled carbon nanotubes.

9. A method for producing semiconducting single-walled carbon nanotubes, comprising:
drying the semiconducting single-walled carbon nanotube dispersion obtained by the method according to claim 1 to give a mixture containing the semiconducting single-walled carbon nanotubes and the copolymer; and
removing the copolymer from the mixture and collecting the semiconducting single-walled carbon nanotubes.

10. A method for producing semiconducting single-walled carbon nanotubes, comprising:
obtaining the semiconducting single-walled carbon nanotubes without performing a further separation treatment of the semiconducting single-walled carbon nanotube dispersion obtained by the method according to claim 1 .

11. The method for producing a semiconducting single-walled carbon nanotube dispersion according to claim 1 , wherein M represents a hydrogen atom in the formula (1).

12. The method for producing a semiconducting single-walled carbon nanotube dispersion according to claim 1 , wherein q is 3 or more and 12 or less in the formula (3).

13. The method for producing a semiconducting single-walled

Assignees

• Kao Corp

Inventors

• Hiraishi Atsushi

Classifications

• C09D11/50

  Sympathetic, colour changing or similar inks · CPC title

• C09D11/037

  characterised by the pigment · CPC title

• C08F2800/20

  as weight or mass percentages · CPC title

• C08F2800/10

  as molar percentages · CPC title

• C08F220/68

  Esters · CPC title