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

Patent metadata

Field	Value
Publication number	US-11167993-B2
Application number	US-201816607048-A
Country	US
Kind code	B2
Filing date	Jun 6, 2018
Priority date	Jun 19, 2017
Publication date	Nov 9, 2021
Grant date	Nov 9, 2021

Abstract

The present invention is to provide a surface-modified nanodiamond having excellent affinity for an organic solvent and a resin and having high dispersibility in an organic solvent and in a resin. The surface-modified nanodiamond according to an embodiment of the present invention has a structure in which a surface of a nanodiamond particle is modified by a group represented by Formula (1) below. In Formula (1), R1 represents an aliphatic hydrocarbon group having 6 or more carbons. R2 and R3 may be the same or different and are each a hydrogen atom, an aliphatic hydrocarbon group having from 1 to 3 carbons, or a group represented by Formula (2) below.

First claim

The invention claimed is:

1. A nanodiamond liquid dispersion comprising:
a surface-modified nanodiamond in a concentration of 0.0001 to 10 mass %; and
an organic solvent in a content of 90 mass % or greater,
the surface-modified nanodiamond and the organic solvent being present in a total content of 95 mass % or greater,
wherein the surface-modified nanodiamond have a structure in which a surface of a nanodiamond particle is modified by a group represented by Formula (1):

where R 1 represents an aliphatic hydrocarbon group having 6 or more carbons, an atomic bond indicated by a wavy line bonds to the surface of the nanodiamond particle, and R 2 and R 3 may be the same or different and are each a hydrogen atom, an aliphatic hydrocarbon group having from 1 to 3 carbons, or a group represented by Formula (2):

where R 1 is as described above, R 5 and R 6 may be the same or different and each represent a hydrogen atom or an aliphatic hydrocarbon group having from 1 to 3 carbons, m and n may be the same or different and each represent an integer of 0 or greater, an atomic bond extending toward left from a silicon atom bonds to an oxygen atom, and an atomic bond indicated by a wavy line bonds to the surface of the nanodiamond particle.

2. The nanodiamond liquid dispersion according to claim 1 , wherein the organic solvent is an aromatic hydrocarbon.

3. The nanodiamond liquid dispersion according to claim 1 , wherein a median diameter of the surface-modified nanodiamond included in the organic solvent is 100 nm or less.

4. The nanodiamond liquid dispersion according to claim 1 , wherein the nanodiamond liquid dispersion has properties below:
in a case where a liquid component is removed from the nanodiamond liquid dispersion to produce a powdered surface-modified nanodiamond and the powdered surface-modified nanodiamond is redispersed in the organic solvent to prepare a nanodiamond liquid dispersion having a solid content concentration of 1 wt. %, a particle diameter (D50) of the surface-modified nanodiamond in the prepared nanodiamond liquid dispersion is from 10 to 100 nm.

5. The nanodiamond liquid dispersion according to claim 2 , wherein a median diameter of the surface-modified nanodiamond included in the organic solvent is 100 nm or less.

6. A nanodiamond liquid dispersion according to claim 1 , wherein R 1 in formula (1) is an alkyl group having from 14 to 25 carbons.

7. The nanodiamond liquid dispersion according to claim 6 , wherein a median diameter of the surface-modified nanodiamond included in the organic solvent is 100 nm or less.

8. The nanodiamond liquid dispersion according to claim 6 , wherein a concentration of the surface-modified nanodiamond is from 0.0001 to 10 mass %.

9. The nanodiamond liquid dispersion according to claim 6 , wherein the nanodiamond liquid dispersion has properties below:
in a case where a liquid component is removed from the nanodiamond liquid dispersion to produce a powdered surface-modified nanodiamond and the powdered surface-modified nanodiamond is redispersed in the organic solvent to prepare a nanodiamond liquid dispersion having a solid content concentration of 1 wt. %, a particle diameter (D50) of the surface-modified nanodiamond in the prepared nanodiamond liquid dispersion is from 10 to 100 nm.

Assignees

• Daicel Corp

Inventors

• Umemoto Kouichi

Classifications

• C08K9/06

  with silicon-containing compounds · CPC title

• C09C3/12

  Treatment with organosilicon compounds {(C09C3/006 takes precedence)} · CPC title

• C08K3/04

  Carbon · CPC title

• B82Y40/00

  Manufacture or treatment of nanostructures · CPC title

• C09D17/00

  Pigment pastes, e.g. for mixing in paints (artists' paints C09D5/06) · CPC title