Inorganic oxide sol dispersed in hydrocarbon and production method therefor

Patent metadata

Field	Value
Publication number	US-11549019-B2
Application number	US-202117639978-A
Country	US
Kind code	B2
Filing date	Jul 6, 2021
Priority date	Jul 7, 2020
Publication date	Jan 10, 2023
Grant date	Jan 10, 2023

Abstract

A sol of inorganic oxide particles is stably dispersed in a hydrophilic organic solvent containing a hydrocarbon such as a paraffinic hydrocarbon or a naphthenic hydrocarbon. The sol contains a dispersion medium containing an organic solvent containing a C6-18 paraffinic hydrocarbon, a C6-18 naphthenic hydrocarbon, or a mixture of these, a C4-8 alcohol having a carbon chain with a carbon-carbon bond in the molecule in an amount of 0.1 to 5% by mass in the entire dispersion medium, and inorganic oxide particles having an average particle diameter of 5 to 200 nm as measured by dynamic light scattering as a dispersoid, wherein the inorganic oxide particles contain a C1-3 alkyl group bonded to a silicon atom and a C4-18 alkyl group. The paraffinic hydrocarbon is a normal paraffinic hydrocarbon or an isoparaffinic hydrocarbon. The naphthenic hydrocarbon is a saturated aliphatic cyclic hydrocarbon substitutable with a C1-10 alkyl group.

First claim

The invention claimed is:

1. A sol comprising inorganic oxide particles as a dispersoid; and a dispersion medium containing an organic solvent containing a C 6-18 paraffinic hydrocarbon, a C 6-18 naphthenic hydrocarbon, or a mixture of these, and a C 4-8 alcohol having a carbon-carbon bond in the molecule, wherein:
the alcohol is contained in an amount of 0.1 to 5% by mass in the entire dispersion medium, the inorganic oxide particles have an average particle diameter of 5 to 200 nm as measured by dynamic light scattering, and the inorganic oxide particles contain a silicon atom bonded to a C 1-3 alkyl group and a silicon atom bonded to a C 4-18 alkyl group on a surface of the inorganic oxide particles.

2. The sol according to claim 1 , wherein the inorganic oxide particles contain a silane compound in which a C 4-18 alkyl group is bonded to a silicon atom and a silane compound in which a C 1-3 alkyl group is bonded to a silicon atom in proportions by mole of 1:0.1 to 30 in terms of silicon atom.

3. The sol according to claim 1 , wherein the paraffinic hydrocarbon is a normal paraffinic hydrocarbon or an isoparaffinic hydrocarbon.

4. The sol according to claim 1 , wherein the naphthenic hydrocarbon is a saturated aliphatic cyclic hydrocarbon substitutable with a C 1-10 alkyl group.

5. The sol according to claim 1 , wherein the alcohol is n-butanol, n-pentanol, or n-hexanol.

6. The sol according to claim 1 , wherein the inorganic oxide particles are particles of an oxide of at least one metal selected from the group consisting of Si, Ti, Fe, Cu, Zn, Y, Zr, Nb, Mo, In, Sn, Sb, Ta, W, Pb, Bi, and Ce.

7. The sol according to claim 6 , wherein the inorganic oxide particles are silica particles, zirconia particles, or titania particles.

8. The sol according to claim 6 , wherein the inorganic oxide particles are metal oxide particles having a core-shell structure in which the surface of a core particle formed of at least one metal oxide selected from the group consisting of tin oxide, zirconium oxide, and titanium oxide is coated with at least one selected from among silica, tin oxide, antimony oxide, and tungsten oxide.

9. The sol according to claim 1 , wherein the inorganic oxide particles are coated with a silane compound of the following
R 1 a Si(R 2 ) 4-a   Formula (1)

wherein R 1 is an alkyl group, a halogenated alkyl group, an alkenyl group, or an organic group having an epoxy group, a (meth)acryloyl group, a mercapto group, an amino group, a ureido group, or a cyano group, and is bonded to a silicon atom via an Si—C bond; at least one R is a C 4-18 alkyl group and is bonded to a silicon atom via an Si—C bond; R 2 is an alkoxy B group, an acyloxy group, or a halogen group; and a is an integer of 1 to 3.

10. The sol according to claim 9 , wherein the inorganic oxide particles are coated with at least one silane compound selected from the group consisting of silane compounds of Formula (1) and the following Formulae (2) and (3):
[R 3 b Si(R 4 ) 3-b ] 2 Y c   Formula (2)

R 5 d Si(R 6 ) 4-d   Formula (3)

wherein R 3 and R 5 are each a C 1-3 alkyl group and bonded to a silicon atom via an Si—C bond; R 4 and R 6 are each an alkoxy group, an acyloxy group, or a halogen group; Y is an alkylene group, an NH group, or an oxygen atom; at least one R 3 and at least one R 5 are a C 1-3 alkyl group and bonded to a silicon atom via an Si—C bond; b is an integer of 1 to 3; c is an B integer of 0 or 1; and d is an integer of 1 to 3.

11. The sol according to claim 1 , wherein, when the concentration of the inorganic oxide particles is 50% by mass or less, the viscosity at 20° C. of the sol is 1.0 to 10.0 times the viscosity at 20° C. of the organic solvent containing the C 6-18 paraffinic hydrocarbon, the C 6-18 naphthenic hydrocarbon, or a mixture of these, which serves as the dispersion medium.

12. The sol according to claim 11 , wherein, when the concentration of the inorganic oxide particles is 5 to 50% by mass, the viscosity at 20° C. of the sol is 1.0 to 10.0 times the viscosity at 20° C. of the organic solvent containing the C 6-18 paraffinic hydrocarbon, the C 6-18 naphthenic hydrocarbon, or a mixture of these, which serves as the dispersion medium.

13. A production method for the sol according to claim 9 , the method comprising the following steps (A) to (D):
step (A): a step of preparing a sol containing a C 4-8 alcohol having a carbon-carbon bond in the molecule in an amount of 15% by mass or more in the entire dispersion medium, from a sol containing, as a dispersoid, inorganic oxide particles having an average particle diameter of 5 to 200 nm as measured by dynamic light scattering, and an aqueous solvent or a C 1-3 alcohol as a dispersion medium;
step (B): a step of adding a silane compound of the following Formula (1) to the sol prepared in the step (A), and allowing reaction to proceed at a temperature of 20° C. to the boiling point of the dispersion medium for 0.1 to 6 hours;
step (C): a step of adding a C 6-18 paraffinic hydrocarbon, a C 6-18 naphthenic hydrocarbon, or a mixture of these to the sol prepared in the step (B), and removing water and/or the alcohol to the outside of the system; and
step (D): a step of adding at least one silane compound selected from the group consisting of silane compounds of the following Formulae (2) and (3) to the sol prepared in the step (C) if necessary, and allowing reaction to proceed at a temperature of 20° C. to the boiling point of the dispersion medium for 0.1 to 6 hours:
R 1 a Si(R 2 ) 4-a   Formula (1)

[R 3 b Si(R 4 ) 3-b ] 2 Y c   Formula (2)

R 5 d Si(R 6 ) 4-d   Formula (3)

in Formula (1), R is an alkyl group, a halogenated alkyl group, an alkenyl group, or an organic group having an epoxy group, a (meth)acryloyl group, a mercapto group, an amino group, a ureido group, or a cyano group, and is bonded to a silicon atom via an Si—C bond; at least one R is a C 4-18 alkyl group and is bonded to a silicon atom via an Si—C bond; R 2 is an alkoxy group, an acyloxy group, or a halogen group; and a is an integer of 1 to 3; and, in Formulae (2) and (3), R 3 and R 5 are each a C 1-3 alkyl group and bonded to a silicon atom via an Si—C bond; R 4 and R 6 are each an alkoxy group, an acyloxy group, or a halogen group; Y is an alkylene group, an NH group, or an oxygen atom; at least one R 3 and at least one R 5 are a C 1-3 alkyl group and bonded to a silicon atom via an Si—C bond; b is an integer of 1 to 3; c is B an integer of 0 or 1; and d is an integer of 1 to 3.

14. The production method according to claim 13 , wherein the method further comprises the following step (E) after the step (D):
step (E): a step of adding a C 8-18 paraffinic hydrocarbon, a C 8-18 naphthenic hydrocarbon, or a mixture of these, and removing the alcohol.

Assignees

• Nissan Chemical Corp

Inventors

• Maeta Tomoya
• Suemura Naohiko
• Yoshitake Keiko

Classifications

• B01J13/0039

  Post treatment · CPC title

• C01P2004/82

  two phases having the same anion, e.g. both oxidic phases · CPC title

• C01B33/145 Primary

  Preparation of hydroorganosols, organosols or dispersions in an organic medium · CPC title

• C09C3/12 Primary

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

• C01P2004/62

  Submicrometer sized, i.e. from 0.1-1 micrometer · CPC title