Dispersant and composition

Patent metadata

Field	Value
Publication number	US-12163086-B2
Application number	US-202217687785-A
Country	US
Kind code	B2
Filing date	Mar 7, 2022
Priority date	May 25, 2021
Publication date	Dec 10, 2024
Grant date	Dec 10, 2024

Abstract

The present disclosure relates to a dispersant containing a specific compound having a fluorene skeleton, and a composition using the same.

First claim

What is claimed is:

1. A dispersant comprising a compound represented by the following Chemical Formula 1:

wherein each of X 1 and X 2 is an aromatic ring, each of R 1 , R 2 , R 3 and R 4 is a substituent, each of a, b, c, and d is an integer of 0 to 4, each of R 5 and R 6 is an aliphatic chain, each of n and m is an integer of 2 to 20, each of Y 1 and Y 2 is a bonding group represented by the following Chemical Formula 2, and each of Z 1 and Z 2 is a terminal group represented by the following Chemical Formula 3 or 4,

wherein R 7 is an O, N, or S atom, R 8 is an aliphatic chain, and —* represents a site for linking to Z 1 or Z 2 ,

wherein R 9 is an aliphatic chain,

wherein R 10 is an aliphatic chain, and
wherein at least one of R 1 , R 2 , R 3 and R 4 in Chemical Formula 1 is selected from the group consisting of a halogen group, a cyano group, a nitro group, a hydroxy group, a C 1 to C 10 alkyl group, a C 1 to C 10 alkoxy group, a C 2 to C 10 alkene group, a C 2 to C 10 alkyne group, and a C 4 to C 10 alkenyne group.

2. The dispersant of claim 1 , wherein at least one of X 1 and X 2 in Chemical Formula 1 is selected from the group consisting of a benzene ring, a naphthalene ring, and a biphenyl ring.

3. The dispersant of claim 1 , wherein at least one of X 1 and X 2 in Chemical Formula 1 is a benzene ring.

4. The dispersant of claim 1 , wherein at least one of R 5 and R 6 in Chemical Formula 1 is a C 2 to C 6 saturated hydrocarbon chain.

5. The dispersant of claim 1 , wherein at least one of R 5 and R 6 in Chemical Formula 1 is selected from the group consisting of (CH 2 —CH 2 )—, —(CH 2 —CH 2 —CH 2 )—, —(CH 2 —CH 2 —CH 2 —CH 2 )—, —(CH 2 —CH 2 —CH 2 —CH 2 —CH 2 )—, and —(CH 2 —CH 2 —CH 2 —CH 2 —CH 2 —CH 2 )—.

6. The dispersant of claim 1 , wherein the C 1 to C 10 alkyl group is selected from the group consisting of a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, a 1-methyl-butyl group, a 1-ethyl-butyl group, a pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a hexyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 4-methyl-2-pentyl group, a 3,3-dimethylbutyl group, a 2-ethylbutyl group, a heptyl group, a 1-methylhexyl group, an octyl group, a nonyl group, and a decyl group.

7. The dispersant of claim 1 , wherein the C 1 to C 10 alkoxy group is selected from the group consisting of methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, tert-butoxy, sec-butoxy, pentyloxy, neopentyloxy, isopentyloxy, hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, octyloxy, nonyloxy, and decyloxy.

8. The dispersant of claim 1 , wherein the C 2 to C 10 alkene group is selected from the group consisting of a vinyl group, a 1-propenyl group, and a 1-butenyl group.

9. The dispersant of claim 1 , wherein the C 2 to C 10 alkyne group is selected from the group consisting of an ethynyl group, a 1-propynyl group, and a 1-butynyl group.

10. The dispersant of claim 1 , wherein the C 4 to C 10 alkenyne group is selected from the group consisting of a pent-1-en-4-yne group, and a pent-3-en-1-yne group.

11. The dispersant of claim 1 , wherein at least one of a, b, c, and d in Chemical Formula 1 is an integer of 0.

12. The dispersant of claim 1 , wherein in Chemical Formula 2, R 7 is an O atom and R 8 is a C 2 to C 6 saturated hydrocarbon chain.

13. The dispersant of claim 1 , wherein R 9 in Chemical Formula 3 is a C 2 to C 6 saturated hydrocarbon chain.

14. The dispersant of claim 1 , wherein R 10 in Chemical Formula 4 is a C 2 to C 6 saturated hydrocarbon chain.

15. The dispersant of claim 1 , wherein the compound represented by Chemical Formula 1 comprises a compound represented by the following Chemical Formula 5:

wherein each of n and m is an integer of 2 to 20.

16. The dispersant of claim 1 , wherein the compound represented by Chemical Formula 1 comprises a compound represented by the following Chemical Formula 6:

wherein each of n and m is an integer of 2 to 20.

17. A composition comprising:
zirconia nanoparticles subjected to a surface treatment with a dispersant; and
a solvent,
wherein the dispersant is the dispersant of claim 1 .

18. The composition of claim 17 , wherein the dispersant is adsorbed to the surface of the zirconia nanoparticle.

19. The composition of claim 17 , wherein the solvent is selected from the group consisting of tetrahydrofuran, methylene chloride, and chloroform.

20. A dispersant comprising a compound represented by the following Chemical Formula 1:

wherein each of X 1 and X 2 is an aromatic ring, each of R 1 , R 2 , R 3 and R 4 is a substituent, each of a, b, c, and d is an integer of 0 to 4, each of R 5 and R 6 is an aliphatic chain, each of n and m is an integer of 2 to 20, each of Y 1 and Y 2 is a bonding group represented by the following Chemical Formula 2, and each of Z 1 and Z 2 is a terminal group represented by the following Chemical Formula 3 or 4,

wherein R 7 is an O, N, or S atom, R 8 is an aliphatic chain, and —* represents a site for linking to Z 1 or Z 2 ,

wherein R 9 is an aliphatic chain,

wherein R 10 is an aliphatic chain,
wherein at least one of X 1 and X 2 in Chemical Formula 1 is selected from the group consisting of a benzene ring, a naphthalene ring, and a biphenyl ring,
wherein at least one of R 5 and R 6 in Chemical Formula 1 is a C 2 to C 6 saturated hydrocarbon chain,
wherein in Chemical Formula 2, R 7 is an O atom and R 8 is a C 2 to C 6 saturated hydrocarbon chain,
wherein R 9 in Chemical Formula 3 is a C 2 to C 6 saturated hydrocarbon chain, and
wherein R 10 in Chemical Formula 4 is a C 2 to C 6 saturated hydrocarbon chain.

Assignees

• Samsung Electro Mech

Inventors

• Kim Young O
• Yoon Chang Hyun
• Lim Eun Jung
• Lee Jung Hyun
• Lee Choon Keun

Classifications

• C09C1/00

  Treatment of specific inorganic materials other than fibrous fillers (tenebrescent materials C09K9/00; luminescent materials C09K11/00); Preparation of carbon black · CPC title

• C01P2004/64

  Nanometer sized, i.e. from 1-100 nanometer · CPC title

• C01P2002/82

  by IR- or Raman-data · CPC title

• C09C3/08

  Treatment with low-molecular-weight {non-polymer} organic compounds {(C09C3/006, C09C3/048 take precedence)} · CPC title

• C09K23/34

  Higher-molecular-weight carboxylic acid esters (esters of higher fatty acids with hydroxyalkylated sulfonic acids or salts thereof C09K23/06) · CPC title