IP Library › Granted Patent US 12,351,464
Granted Patent B2
US 12,351,464 · App. 17/605,596 · Granted Jul 8, 2025

Nanodiamond dispersion composition

Inventors: Norihiro Kimoto (Tokyo, JP); Kouichi Umemoto (Tokyo, JP); Takeru Kashiwagi (Tokyo, JP)
Assignee: DAICEL CORPORATION
C01B32/28C08K3/04C08K5/101C08K9/06C09C3/041C09C3/08C09C3/12C01P2002/88C01P2004/62C01P2004/64C01P2006/22C01P2006/60C08K2201/011C09K3/1472
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 12,351,464
App. No.
17/605,596
Granted
Jul 8, 2025
Kind
B2
Abstract

Provided is a nanodiamond dispersion composition having excellent dispersibility of nanodiamond particles in an organic dispersion medium even when the organic dispersion medium has a small SP value. The nanodiamond dispersion composition according to an embodiment of the present invention includes an organic dispersion medium, nanodiamond particles dispersed in the organic dispersion medium, and a fatty acid ester dispersing agent. The fatty acid ester dispersing agent preferably has a mass loss rate of 20% or less when held in an air atmosphere at a temperature of 200° C. for 180 minutes. The fatty acid ester dispersing agent preferably has an acid value of 40 mgKOH/g or less.

Claims (25)

1. A nanodiamond dispersion composition comprising:

an organic dispersion medium;

a nanodiamond particle dispersed in the organic dispersion medium; and

a fatty acid ester dispersing agent, wherein an average molecular weight Mp of the fatty acid ester dispersing agent is from 5,100 to 8,200, wherein the nanodiamond particle includes a surface-modified nanodiamond.

2. The nanodiamond dispersion composition according to claim 1 , wherein the fatty acid ester dispersing agent has a mass loss rate of 20% or less when the fatty acid ester dispersing agent is held in an air atmosphere at a temperature of 200° C. for 180 minutes.

3. The nanodiamond dispersion composition according to claim 1 , wherein the fatty acid ester dispersing agent has an acid value of 40 mgKOH/g or less.

4. The nanodiamond dispersion composition according to claim 1 , wherein the nanodiamond particle has an average dispersed particle size from 2 to 240 nm.

5. The nanodiamond dispersion composition according to claim 1 , having a haze value of 5 or less.

6. The nanodiamond dispersion composition according to claim 1 , wherein the organic dispersion medium has a SP value from 6.0 to 12.0 (cal/cm 3 ) 1/2 .

7. The nanodiamond dispersion composition according to claim 1 , having a viscosity from 0.2 to 120 mPa's at 25° C.

8. The nanodiamond dispersion composition according to claim 1 , wherein a content ratio of the nanodiamond particles is from 0.01 to 5.0 mass %.

9. The nanodiamond dispersion composition according to claim 1 , wherein the surface-modified nanodiamond is a nanodiamond particle of which surface is modified by a group represented by Formula (I):

—X—R  (I)

where in Formula (I), X represents —Si—, —NH—, —O—, —O—C(═O)—, —C(═O)—O—, —NH—C(═O)—, —C(═O)—NH—, or —S—, and a bond extending left from X binds to the nanodiamond particle; and

R represents a monovalent organic group, and an atom that binds to X is a carbon atom.

10. The nanodiamond dispersion composition according to claim 9 , wherein X in Formula (I) represents —Si—, —NH—, —O—, or —O—C(═O)—.

11. The nanodiamond dispersion composition according to claim 9 , wherein a number of carbon atoms in the monovalent organic group is from 4 to 25.

12. The nanodiamond dispersion composition according to claim 9 , wherein in Formula (I), X is —NH—, and R is a monovalent organic group containing from 8 to 20 carbon atoms.

13. The nanodiamond dispersion composition according to claim 9 , wherein in Formula (I), X is —NH—, and R is a monovalent organic group containing a hydrocarbon group having 4 or more carbon atoms in a straight chain.

14. The nanodiamond dispersion composition according to claim 9 , wherein in Formula (I), R includes a hydrocarbon group having 4 or more carbon atoms in a straight chain.

15. The nanodiamond dispersion composition according to claim 9 , wherein the surface-modified nanodiamond particle is surface-modified by a compound containing an organic group or a functional group containing an organic group.

16. The nanodiamond dispersion composition according to claim 9 , wherein the organic group is an organic group having 4 or more carbons.

17. The nanodiamond dispersion composition according to claim 1 , wherein the fatty acid ester dispersing agent has an amine value of 5 mgKOH/g or less.

18. The nanodiamond dispersion composition according to claim 1 , wherein a content of the fatty acid ester dispersing agent with respect to 100 parts by mass of a total amount of the nanodiamond particle in the nanodiamond dispersion composition is from 10 to 10000 parts by mass.

19. The nanodiamond dispersion composition according to claim 1 , wherein a content ratio of the fatty acid ester dispersing agent with respect to a total amount of a dispersing agent contained in the nanodiamond dispersion composition is 90 mass % or greater.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 22, 2021
From: KIMOTO, NORIHIRO; UMEMOTO, KOUICHI; KASHIWAGI, TAKERU
To: DAICEL CORPORATION
Reel/Frame 057876/0039 →
Priority Claims (1)
JP 2019-101168 · May 30, 2019 · national
Continuity (1)
Related Publication 20220259048A1 · Aug 18, 2022
References Cited (32)
US 7300958B2 · Kataoka et al. · 2007 [cited by applicant]
US 8507414B2 · Takahama et al. · 2013 [cited by applicant]
US 8598098B2 · Nakagawa et al. · 2013 [cited by applicant]
US 8658578B2 · Hsin · 2014 [cited by examiner]
US 10766776B2 · Makino et al. · 2020 [cited by applicant]
US 11167993B2 · Umemoto · 2021 [cited by applicant]
US 20050008560A1 · Kataoka et al. · 2005 [cited by applicant]
US 20080248979A1 · Nakagawa · 2008 [cited by examiner]
US 20110059876A1 · Takahama · 2011 [cited by examiner]
US 20160060563A1 · Kim · 2016 [cited by examiner]
US 20200123012A1 · Makino et al. · 2020 [cited by applicant]
US 20200189916A1 · Umemoto · 2020 [cited by applicant]
US 20230331959A1 · Kimoto · 2023 [cited by examiner]
US 20240240101A1 · Kimoto · 2024 [cited by examiner]
JP 20051983A · 2005 [cited by applicant]
JP 2008179738A · 2008 [cited by applicant]
JP 2010128669A · 2010 [cited by applicant]
JP 201184609A · 2011 [cited by applicant]
JP 2013117016A · 2013 [cited by applicant]
JP 5364588B2 · 2013 [cited by applicant]
JP 2017186234A · 2017 [cited by applicant]
JP 201644092A · 2018 [cited by applicant]
WO WO2009128258A1 · 2009 [cited by applicant]
WO WO2018235599A1 · 2018 [cited by applicant]
Krueger et al., Advanced Functional Materials, (2012), v22, p. 890-906. [cited by examiner]
“Poly(glycidyl methacrylate) Mn 10K-20K”, Sigma-Aldrich Catalog, downloaded Dec. 16, 2024. [cited by examiner]
“Polymethyl methacrylate (PMMA), 100k”, ALFA Chemistry product catalog, downloaded Dec. 16, 2024. [cited by examiner]
Japanese Office Action for Japanese Application No. 2021-522262, dated Apr. 2, 2024. [cited by applicant]
Extended European Search Report dated Aug. 23, 2023 for Application No. 20813703.4. [cited by applicant]
Kim et al., “Friction, Wear, and Scuffing Characteristics of Marine Engine Lubricants with Nanodiamond Particles”, Tribology Transactions, vol. 59, No. 6, 2016 (Published online Jul. 7, 2016), pp. 1098-1103 (7 pages tot… [cited by applicant]
International Preliminary Report on Patentability and Written Opinion of the International Searching Authority for International Application No. PCT/JP2020/019893, dated Nov. 16, 2021, with an English translation. [cited by applicant]
International Search Report for International Application No. PCT/JP2020/019893, dated Jul. 21, 2020, with an English translation. [cited by applicant]