Surface-modified nanodiamond, surface-modified nanodiamond dispersion liquid, and resin dispersion

Patent metadata

Field	Value
Publication number	US-11046834-B2
Application number	US-201816494624-A
Country	US
Kind code	B2
Filing date	Apr 3, 2018
Priority date	Apr 7, 2017
Publication date	Jun 29, 2021
Grant date	Jun 29, 2021

Abstract

To provide a surface-modified nanodiamond including an N-substituted or unsubstituted amino group having excellent reactivity with other compounds; and having excellent dispersibility in dispersion media and resins. The surface-modified nanodiamond according to the present invention is a surface-modified nanodiamond including a surface-modifying group on a surface of a nanodiamond particle, wherein the surface-modifying group includes a group represented by Formula (1) below, wherein reference signs in Formula (1) below are as described in the present specification.

First claim

The invention claimed is:

1. A surface-modified nanodiamond comprising a surface-modifying group on a surface of a nanodiamond particle, wherein the surface-modifying group comprises a group represented by Formula (1):

where R a represents an alkylene group having from 1 to 12 carbons, R b and R c each represent a hydrogen atom, an alkyl group having from 1 to 3 carbons, an aryl group, or an aralkyl group, and R d represents an identical or different alkyl group having from 1 to 3 carbons; a bond of an oxygen atom bonded to an atomic bond indicated by a wavy line in Formula (1) is identical or different and bonds to a hydrogen atom, an alkyl group having from 1 to 3 carbons, an acyl group, or a silicon atom in another group represented by Formula (1); n is 0, 1, or 2; m is 1, 2, or 3; and m+n≤3; and ND in Formula (1) represents the nanodiamond particle;
wherein at least one of R b and R c represents an alkyl group having 1 to 3 carbon atoms or a phenyl group.

2. The surface-modified nanodiamond according to claim 1 , wherein the nanodiamond particle is a detonation nanodiamond particle.

3. A surface-modified nanodiamond dispersion liquid comprising the surface-modified nanodiamond described in claim 1 and a dispersion medium.

4. The surface-modified nanodiamond dispersion liquid according to claim 3 , wherein a median size of the surface-modified nanodiamond is 50 nm or less.

5. The surface-modified nanodiamond dispersion liquid according to claim 4 , wherein the surface-modified nanodiamond dispersion liquid comprises zirconium, and a ratio of the zirconium, in terms of Zr element, is 0.01 wt. % or greater based on a total content of the surface-modified nanodiamond and the zirconium, in terms of Zr element, contained in the surface-modified nanodiamond dispersion liquid.

6. A resin dispersion comprising the surface-modified nanodiamond described in claim 1 and a resin.

7. The resin dispersion according to claim 6 , wherein the resin dispersion comprises zirconium, and a ratio of the zirconium, in terms of Zr element, is 0.01 wt. % or greater based on a total content of the surface-modified nanodiamond and the zirconium, in terms of Zr element, contained in the resin dispersion.

8. The surface-modified nanodiamond according to claim 1 , obtained by subjecting a nanodiamond particle and a silane coupling agent comprising a hydrocarbon group comprising an N-substituted or unsubstituted amino group to condensation reaction.

9. The surface modified nanodiamond according to claim 1 , wherein Ra in Formula (1) is a propylene group.

10. The surface-modified nanodiamond according to claim 1 , wherein R b and R c in Formula (1) are each a hydrogen atom, an alkyl group having from 1 to 3 carbons, or a phenyl group.

11. The surface-modified nanodiamond according to claim 9 , wherein R b and R c in Formula (1) are each a hydrogen atom, an alkyl group having from 1 to 3 carbons, or a phenyl group, wherein at least one of R b and R c represents an alkyl group having 1 to 3 carbon atoms or a phenyl group.

12. The surface-modified nanodiamond according to claim 1 , wherein n in Formula (1) is 0.

13. The surface-modified nanodiamond according to claim 11 , wherein n in Formula (1) is 0.

14. The surface-modified nanodiamond according to claim 13 , wherein the nanodiamond particle is a detonation nanodiamond particle.

15. The surface-modified nanodiamond dispersion liquid according to claim 3 , wherein a content of the surface-modified nanodiamond is from 0.001 to 10 wt. %.

16. A surface-modified nanodiamond dispersion liquid comprising the surface-modified nanodiamond described in claim 14 and a dispersion medium.

17. The surface-modified nanodiamond dispersion liquid according to claim 16 , wherein the surface-modified nanodiamond dispersion liquid comprises zirconium, and a ratio of the zirconium, in terms of Zr element, is 0.01 wt. % or greater based on a total content of the surface-modified nanodiamond and the zirconium, in terms of Zr element, contained in the surface-modified nanodiamond dispersion liquid.

18. The surface-modified nanodiamond dispersion liquid according to claim 17 , wherein a content of an additional component is 30 wt. % or less based on a total amount of the surface-modified ND dispersion liquid.

19. The surface-modified nanodiamond dispersion liquid according to claim 18 , wherein a content of the surface-modified nanodiamond is from 0.001 to 10 wt. %.

20. The resin dispersion according to claim 6 , wherein a content of the surface-modified nanodiamond is from 0.0001 to 10 wt. %.

21. The surface-modified nanodiamond according to claim 1 , wherein the compound of Formula (1) is trimethoxy[3-(phenylamino)propyl]trimethoxysilane or [3-(N,N-dimethylamino)propyl]trimethoxysilane.

Assignees

• Daicel Corp

Inventors

• Umemoto Kouichi

Classifications

• C08K3/04

  Carbon · CPC title

• C08K9/06 Primary

  with silicon-containing compounds · CPC title

• B82Y30/00

  Nanotechnology for materials or surface science, e.g. nanocomposites · CPC title

• C01B32/26 Primary

  Preparation (by using ultra-high pressure B01J3/06; by crystal growth C30B29/04) · CPC title

• C01B32/28 Primary

  After-treatment, e.g. purification, irradiation, separation or recovery · CPC title