Fluoromonomer and fluorooligomer compounds, photopolymerizable composition, and hydrophobic film using the same

Patent metadata

Field	Value
Publication number	US-10995215-B2
Application number	US-201816032712-A
Country	US
Kind code	B2
Filing date	Jul 11, 2018
Priority date	Jul 12, 2017
Publication date	May 4, 2021
Grant date	May 4, 2021

Abstract

The present disclosure relates to novel fluoromonomer and fluorooligomer compounds, a photopolymerizable composition including these compounds, methods for producing these compounds, and a hydrophobic film using the photopolymerizable composition.

First claim

We claim:

1. A fluoromonomer compound, represented by the following Chemical Formula 2:

wherein in the Chemical Formula 2,
k is an integer of from 1 to 5.

2. A fluorooligomer compound, represented by the following Chemical Formula 3:

wherein in the Chemical Formula 3,
R 1 and R 2 are each independently,

and
k is an integer of from 1 to 5.

3. A photopolymerizable composition, comprising the fluorooligomer compound according to claim 2 and a photoinitiator.

4. The photopolymerizable composition of claim 3 , further comprising
a fluoromonomer compound selected from the group consisting of a compound represented by the following Chemical Formula 1, a compound represented by the following Chemical Formula 2, and combinations thereof:

wherein in the Chemical Formula 1,
n is an integer of 1 to 5;

wherein in the Chemical Formula 2,
k is an integer of from 1 to 5.

5. The photopolymerizable composition of claim 3 ,
wherein the composition comprises the fluorooligomer compound of from 10 to 99 parts by weight and the photoinitiator of from 1 to 10 parts by weight.

6. The photopolymerizable composition of claim 4 ,
wherein the composition comprises the fluorooligomer compound of from 10 to 50 parts by weight, the photoinitiator of from 1 to 10 parts by weight, and the fluoromonomer compound of from 60 to 80 parts by weight.

7. A hydrophobic film, formed by photopolymerization and photo-curing of the photopolymerizable composition according to claim 3 .

8. The hydrophobic film of claim 7 ,
wherein the photopolymerizable composition further comprises a fluoromonomer compound selected from the group consisting of a compound represented by the following Chemical Formula 1, a compound represented by the following Chemical Formula 2, and combinations thereof:

wherein in the Chemical Formula 1,
n is an integer of 1 to 5;

wherein in the Chemical Formula 2,
k is an integer of from 1 to 5.

9. The hydrophobic film of claim 7 ,
wherein the photopolymerizable composition comprises the fluorooligomer compound of from 10 to 99 parts by weight and the photoinitiator of from 1 to 10 parts by weight.

10. The hydrophobic film of claim 7 ,
wherein the photopolymerizable composition comprises the fluorooligomer compound of from 10 to 50 parts by weight, the photoinitiator of from 1 to 10 parts by weight, and the fluoromonomer compound of from 60 to 80 parts by weight.

11. A method for producing a fluoromonomer compound, comprising
mixing a second fluorine-containing compound represented by the following Chemical Formula 5 and a third fluorine-containing compound represented by the following Chemical Formula 6 to obtain a first mixture;
mixing a basic material and an organic solvent to obtain a second mixture; and
adding the second mixture to the first mixture followed by controlling pH thereof to react the second fluorine-containing compound with the third fluorine-containing compound so as to obtain the fluoromonomer compound according to claim 1 :

wherein in the Chemical Formula 6,
k is an integer of from 1 to 5.

12. The method for producing a fluoromonomer compound of claim 11 ,
wherein the controlling pH is performed by adding an acidic material.

13. A method for producing a photopolymerizable oligomer compound, comprising
a) mixing a second fluorine-containing compound represented by the following Chemical Formula 5 and a third fluorine-containing compound represented by the following Chemical Formula 6 to obtain a first mixture:

wherein in the Chemical Formula 6, k is an integer of from 1 to 5;
b) mixing a basic material and an organic solvent to obtain a second mixture;
c) adding the second mixture to the first mixture followed by controlling pH thereof to react the second fluorine-containing compound with the third fluorine-containing compound so as to obtain a fluoromonomer compound represented by the following Chemical Formula 2;

wherein in the Chemical Formula 2, k is an integer of from 1 to 5;
d) mixing an acrylate compound including a hydroxy group and a solvent to obtain a third mixture;
e) adding a compound including a cyanate group to the third mixture to synthesize an acrylate compound including a cyanate group; and
f) adding the fluorinated monomer compound represented by the Chemical Formula 2 to the acrylate compound including the cyanate group to synthesize the photopolymerizable oligomer compound according to claim 2 .

14. The method for producing a photopolymerizable oligomer compound of claim 13 ,
wherein the controlling pH in the step c) is performed by adding an acidic material.

15. The method for producing a photopolymerizable oligomer compound of claim 13 ,
wherein the acrylate compound including a hydroxy group in the step d) is a compound represented by the following Chemical Formula 7:

and
the compound including a cyanate group is a compound represented by the following Chemical Formula 8, and the acrylate compound including a cyanate group is a compound represented by the following Chemical Formula 9 in the step e):

16. The method for producing a photopolymerizable oligomer compound of claim 13 ,
wherein the solvent in the step d) includes a solvent selected from the group consisting of butyl acetate, ethyl acetate, dimethyl formamide, acetone, and combinations thereof.

Assignees

• Ewha University—Industry Collaboration Found

Inventors

• Kim Myung Hwa
• Kim Won-Suk
• Jang Hye Su
• Lee Yejung
• Yun Ye-Seul
• Kwon Yong-Ju
• Kim Saeah

Classifications

• C09D4/00 Primary

  Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16} · CPC title

• C08L75/14 Primary

  Polyurethanes having carbon-to-carbon unsaturated bonds · CPC title

• C08G18/2885

  containing halogen atoms · CPC title

• C09D175/16

  having terminal carbon-to-carbon unsaturated bonds · CPC title

• C08F222/225

  the ester chains containing seven or more carbon atoms · CPC title