Method for manufacturing coating material

Patent metadata

Field	Value
Publication number	US-10570291-B2
Application number	US-201715785113-A
Country	US
Kind code	B2
Filing date	Oct 16, 2017
Priority date	Oct 20, 2016
Publication date	Feb 25, 2020
Grant date	Feb 25, 2020

Abstract

A method for manufacturing a coating material containing a condensate of a hydrolytic silane compound includes a process of obtaining a condensate of a fluorine-containing hydrolytic silane compound and a process of causing the condensate to react with fluoroalcohol.

First claim

What is claimed is:

1. A method for manufacturing a coating material containing a condensate of a hydrolytic silane compound, the method comprising:
a step of obtaining a condensate of a fluorine-containing hydrolytic silane compound; and
a step of causing the condensate to react with fluoroalcohol,
wherein a condensation degree of the condensate is 40% or more.

2. The method for manufacturing a coating material according to claim 1 , wherein the fluoroalcohol contains two or more kinds of fluoroalcohols.

3. The method for manufacturing a coating material according to claim 1 , wherein
the step of obtaining the condensate includes:
a step of mixing the fluorine-containing hydrolytic silane compound and a solvent; and
a step of heating a mixture obtained in the mixing step to obtain a solution containing the condensate, and
the step of causing the condensate to react with fluoroalcohol includes:
a step of adding the fluoroalcohol to the solution containing the condensate; and
a step of heating a mixture obtained in the step of adding the fluoroalcohol.

4. The method for manufacturing a coating material according to claim 3 , wherein the solvent used in the mixing step does not contain fluoroalcohol.

5. The method for manufacturing a coating material according to claim 3 , wherein both the step of obtaining the solution containing the condensate and the step of heating the mixture obtained in the step of adding the fluoroalcohol are performed by heating and refluxing.

6. The method for manufacturing a coating material according to claim 1 , wherein the fluorine-containing hydrolytic silane compound is a compound having a fluorine-containing group selected from the group consisting of a perfluoroalkyl group, a perfluoroaryl group, and a perfluoropolyether group.

7. The method for manufacturing a coating material according to claim 1 , wherein the fluorine-containing hydrolytic silane compound is a compound represented by Formula (1):
(R f ) a —Si(R) b X (4-a-b)   (1)

wherein, in Formula (1), R f represents an alkyl group having one or more fluorine atoms or an aryl group having one or more fluorine atoms, R represents a non-hydrolytic substituent, X represents a hydrolytic substituent, a is 1 or 2, b is an integer of 0 to 2, and a+b is an integer of 1 to 3.

8. The method for manufacturing a coating material according to claim 1 , wherein the fluorine-containing hydrolytic silane compound is at least one of compounds represented by Formulae (3) to (6):

wherein, in Formulae (3) to (6), Rp represents a perfluoropolyether group, A and A 1 each independently represent an organic group having 1 to 12 carbon atoms, X 1 represents a hydrolytic substituent, Y 1 and R 1 each independently represent a non-hydrolytic substituent, Z 1 represents a hydrogen atom or an alkyl group, Q 1 represents a divalent linking group, c is an integer of 1 to 3, m is an integer of 1 to 4, n is 1 or 2, and Q 2 represents a divalent linking group in a case of n=1 and represents a trivalent linking group in a case of n=2.

9. The method for manufacturing a coating material according to claim 8 , wherein the perfluoropolyether group represented by Rp in Formulae (3) to (6) above is represented by Formula (2):

wherein, in Formula (2), o, p, q, and r each independently represent an integer of 0 to 30 and at least one of o, p, q, and r is an integer of 2 or more.

10. The method for manufacturing a coating material according to claim 1 , wherein a condensate of the fluorine-containing hydrolytic silane compound and a photosensitive group-containing hydrolytic silane compound is obtained in the step of obtaining the condensate.

11. The method for manufacturing a coating material according to claim 10 , wherein the photosensitive group-containing hydrolytic silane compound is a compound having an epoxy group represented by Formula (12):
R c —Si(R 2 ) d X 2 (3-d)   (12)

wherein, in Formula (12), R C represents a non-hydrolytic substituent having an epoxy group, R 2 represents a non-hydrolytic substituent, X 2 represents a hydrolytic substituent, and d is an integer of 0 to 2.

12. The method for manufacturing a coating material according to claim 1 , wherein the fluoroalcohol is at least one of compounds represented by Formulae (14) to (16):
(R f1 ) j —(R 3 ) k —OH  (14)

HO—(R f1 ) j —(R 3 ) k —OH  (15)

((R f1 ) j —O) l —(R 3 ) k —OH  (16)

wherein, in formulae (14) to (16), R f1 represents a fluoroalkyl group or a perfluoroaryl group having 3 or more fluorine atoms, R 3 represents a non-hydrolytic substituent, j is 1 or 2, k is an integer of 0 to 2, l is 1 or 2, and j+k is an integer of 1 to 3.

13. The method for manufacturing a coating material according to claim 1 , further comprising:
a dilution step of diluting the obtained solution with a diluent solvent after the step of causing the condensate to react with fluoroalcohol.

14. The method for manufacturing a coating material according to claim 13 , wherein the diluent solvent is a same fluoroalcohol as the fluoroalcohol used in the heating.

15. The method for manufacturing a coating material according to claim 13 , wherein a concentration of a solid content containing the hydrolytic silane compound before the heating in the solution obtained in the dilution step is 0.1 to 30% by mass.

16. A method for manufacturing a coating material containing a condensate of a hydrolytic silane compound, the method comprising:
a step of obtaining a condensate of a fluorine-containing hydrolytic silane compound; and
a step of causing the condensate to react with fluoroalcohol,
wherein the step of obtaining the condensate includes:
a step of mixing the fluorine-containing hydrolytic silane compound and a solvent; and
a step of heating a mixture obtained in the mixing step to obtain a solution containing the condensate, and
wherein the step of causing the condensate to react with fluoroalcohol includes:
a step of adding the fluoroalcohol to the solution containing the condensate; and
a step of heating a mixture obtained in the step of adding the fluoroalcohol.

17. A method for manufacturing a coating material containing a condensate of a hydrolytic silane compound, the method comprising:
a step of obtaining a condensate of a fluorine-containing hydrolytic silane compound; and
a step of causing the condensate to react with fluoroalcohol,
wherein the fluorine-containing hydrolytic silane compound is at least one of compounds represented by Formulae (3) to (6):

wherein, in Formulae (3) to (6), Rp represents a perfluoropolyether group, A and A 1 each independently represent an organic group having 1 to 12 carbon atoms, X 1 represents a hydrolytic substituent, Y 1 and R 1 each independently represent a non-hydrolytic substituent, Z 1 represents a hydrogen atom or an alkyl group, Q 1 represents a divalent linking group, c is an integer of 1 to 3, m is an integer of 1 to 4, n is 1 or 2, and Q 2 represents a divalent linking group in a case of n=1 and represents a trivalent linking group in a case of n=2.

Assignees

• Canon Kk

Inventors

• Hamade Yohei

Classifications

• C08L83/08

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

• C08G77/385

  containing halogens · CPC title

• C08G77/18

  to alkoxy or aryloxy groups · CPC title

• C09D183/08

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

• C09D5/1625 Primary

  organic · CPC title