Surface treatment agent and method for manufacturing surface treatment body

Patent metadata

Field	Value
Publication number	US-12163087-B2
Application number	US-202017595797-A
Country	US
Kind code	B2
Filing date	Jun 4, 2020
Priority date	Jun 21, 2019
Publication date	Dec 10, 2024
Grant date	Dec 10, 2024

Abstract

Please substitute the new Abstract submitted herewith for the original Abstract: The present disclosure provides a surface treatment agent capable of not only being prepared by dissolving raw materials in a short time but also exerting a good water repellency imparting effect, and a method for manufacturing a surface treated body with the use of the surface treatment agent. The surface treatment agent according to the present disclosure includes the following components: (I) at least one kind selected from the group consisting of silicon compounds represented by the following formulas (1) and (2); (II) at least one kind selected from the group consisting of a nitrogen-containing heterocyclic compound represented by the following general formula (3), a nitrogen-containing heterocyclic compound represented by the following general formula (4) and imidazole; (III) an organic solvent; and (IV) at least one kind selected from the group consisting of silicon compounds represented by the following formulas (5) and (6).

First claim

The invention claimed is:

1. A surface treatment agent for surface treatment of a workpiece, comprising the following components:
(I) at least one kind selected from the group consisting of silicon compounds represented by the following general formulas [1] and [2];
(II) at least one kind selected from the group consisting of a nitrogen-containing heterocyclic compound represented by the following general formula [3], a nitrogen-containing heterocyclic compound represented by the following general formula [4] and imidazole;
(III) an organic solvent; and
(IV) at least one kind selected from the group consisting of silicon compound represented by the following general formulas [5] and [6]
(R 1 ) a (H) b Si[N(R 2 )C(═O)R 3 ] 4-a-b   [1]

where R 1 is each independently a C 1 -C 18 monovalent hydrocarbon group in which a part or all of hydrogen atoms may be substituted by a fluorine atom; R 2 is each independently a group selected from the group consisting of a C 1 -C 6 alkyl group in which a part or all of hydrogen atoms may be substituted by a fluorine atom, and a hydrogen atom; R 3 is each independently a C 1 -C 6 alkyl group in which a part or all of hydrogen atoms may be substituted by a fluorine atom; a is an integer of 1 to 3; b is an integer of 0 to 2; and the sum of a and b is 1 to 3,
(R 4 ) c (H) d Si[OC(R 5 )═NSi(R 6 ) e (H) 3-e ] 4-c-d   [2]

where R 4 and R 6 are each independently a C 1 -C 18 monovalent hydrocarbon group in which a part or all of hydrogen atoms may be substituted by a fluorine atom; R 5 is each independently a group selected from the group consisting of a C 1 -C 6 alkyl group in which a part or all of hydrogen atoms may be substituted by a fluorine atom, and a hydrogen atom; c is an integer of 1 to 3; d is an integer of 0 to 2; e is an integer of 1 to 3; and the sum of c and d is 1 to 3,

where R 7 and R 8 are each independently a divalent organic group consisting of carbon and/or nitrogen and hydrogen, in which the total number of carbon and nitrogen atoms is 1 to 9; and, in the case where the total number of carbon and nitrogen atoms is 2 or greater, there may exit a carbon atom that does not form a ring,

where R 9 is a C 1 -C 6 alkyl group in which a part of all of hydrogen atoms may be substituted by a fluorine atom, a trialkylsilyl group having a C 1 -C 8 alkyl group in which a part of all of hydrogen atoms may be substituted by a fluorine atom, a C 2 -C 6 alkenyl group in which a part of all of hydrogen atoms may be substituted by a fluorine atom, a C 1 -C 6 alkoxy group in which a part of all of hydrogen atoms may be substituted by a fluorine atom, an amino group, an alkylamino group having a C 1 -C 6 alkyl group in which a part of all of hydrogen atoms may be substituted by a fluorine atom, a dialkylamino group having a C 1 -C 6 alkyl group in which a part of all of hydrogen atoms may be substituted by a fluorine atom, a C 1 -C 6 aminoalkyl group in which a part of all of hydrogen atoms may be substituted by a fluorine atom, a nitro group, a cyano group, a phenyl group, a benzyl group, or a halogen atom; and R 10 , R 11 and R 12 are each independently a C 1 -C 6 alkyl group in which a part or all of hydrogen atoms may be substituted by a fluorine atom, or a hydrogen atom,
(R 13 ) f (H) g Si[OC(═O)R 14 ] 4-f-g   [5]

where R 13 is each independently a C 1 -C 18 monovalent hydrocarbon group in which a part or all of hydrogen atoms may be substituted by a fluorine atom; R 14 is each independently a C 1 -C 6 alkyl group in which a part or all of hydrogen atoms may be substituted by a fluorine atom; f is an integer of 1 to 3; g is an integer of 0 to 2; and the sum of f and g is 1 to 3,
(R 15 ) h (H) i SiX 4-h-i   [6]

where R 15 is each independently a C 1 -C 18 monovalent hydrocarbon group in which a part or all of hydrogen atoms may be substituted by a fluorine atom; X is each independently a halogen atom, an alkylsulfonate group, or a perfluoroalkylsulfonate group; h is an integer of 1 to 3; i is an integer of 0 to 2; and the sum of h and i is 1 to 3.

2. The surface treatment agent according to claim 1 , wherein an amount of the component (IV) contained relative to the amount of the component (I) is more than or equal to 0.001 and less than 1 in terms of molar ratio.

3. The surface treatment agent according to claim 1 , wherein the component (IV) comprises at least one kind of silicon compound represented by the general formula [5] in which f is 3; and R 14 is a C 1 -C 6 fluorine-containing alkyl group.

4. The surface treatment agent according to claim 1 , wherein the component (IV) comprises (CH 3 ) 3 SiOC(═O)CF 3 .

5. The surface treatment agent according to claim 1 , wherein the component (IV) comprises a silicon compound represented by the general formula [6] in which h is 3; i is 0; and R 15 is a C 1 -C 6 alkyl group or a C 1 -C 6 fluorine-containing alkyl group.

6. The surface treatment agent according to claim 1 , wherein the component (IV) comprises a silicon compound represented by the general formula [6] in which X is a chlorine atom.

7. The surface treatment agent according to claim 1 , wherein the component (IV) comprises (CH 3 ) 3 SiCl.

8. The surface treatment agent according to claim 1 , wherein a concentration of the component (II) is 0.05 to 10 mass % with respect to a total amount of the components (I) to (IV).

9. The surface treatment agent according to claim 1 , wherein the component (II) is liquid at 25° C. and 1.0 atmospheric pressure.

10. The surface treatment agent according to claim 1 , wherein, in the general formula [4], R 9 is a C 1 -C 4 alkyl group or a trimethylsilyl group, and R 10 , R 11 and R 12 are hydrogen atoms, respectively.

11. The surface treatment agent according to claim 1 , wherein the component (II) is at least one selected from the group consisting of N-methylimidazole, N-ethylimidazole, N-propylimidazole, N-butylimidazole and trimethylsilylimidazole.

12. The surface treatment agent according to claim 1 , wherein the concentration of the component (I) is 0.1 to 35 mass % with respect to the total amount of the components (I) to (IV).

13. The surface treatment agent according to claim 1 , wherein the component (I) comprises at least one kind of silicon compound represented by the general formula [1] in which a is 3; R 2 is a methyl group; and R 3 is a C 1 -C 6 fluorine-containing alkyl group.

14. The surface treatment agent according to claim 1 , wherein the component (I) comprises (CH 3 ) 3 SiN(CH 3 )C(═O)CF 3 .

15. The surface treatment agent according to claim 1 , wherein the component (I) comprises at least one kind of silicon compound represented by the general formula [2] in which c and e are each 3; and R 5 is a methyl group or a trifluoromethyl group.

16. The surface treatment agent according to claim 1 , wherein the component (I) comprises (CH 3 ) 3 SiOC(CF 3 )═NSi(CH 3 ) 3 .

17. The surface treatment agent according to claim 1 , wherein the organic solvent is an aprotic solvent.

18. A method for manufacturing a surface treated body, comprising bringing the surface treatment agent according to claim 1 into contact with a surface of a workpiece and thereby surface treating the workpiece.

Assignees

• Central Glass Co Ltd

Inventors

• Fukui Yuki
• Okumura Yuzo
• Terui Yoshiharu
• Kumon Soichi

Classifications

• H10P95/00

  Generic processes or apparatus for manufacture or treatments not covered by the other groups of this subclass · CPC title

• H10P70/20

  Cleaning during device manufacture · CPC title

• G03F7/40 Primary

  Treatment after imagewise removal, e.g. baking · CPC title

• C09D183/08

  containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen · CPC title

• G03F7/16

  Coating processes; Apparatus therefor (applying coatings to base materials in general B05; applying photosensitive compositions to base for photographic purposes G03C1/74) · CPC title