Surface coating material, coating film, and hydrophilic oil repellent member

Patent metadata

Field	Value
Publication number	US-10364360-B2
Application number	US-201515329426-A
Country	US
Kind code	B2
Filing date	Jul 30, 2015
Priority date	Jul 30, 2014
Publication date	Jul 30, 2019
Grant date	Jul 30, 2019

Abstract

A surface coating material is provided for forming a hydrophilic oil repellent layer on at least a part of the surface of a substrate, and the surface coating material includes one or more fluorine-based compounds represented by the following formulas (1) to (4), a binder, and a solvent.

First claim

The invention claimed is:

1. A surface-coating material which forms a hydrophilic/oil-repellent layer on at least a part of the surface of a substrate, comprising:
one or more fluorine-based compounds represented by the following formulas (2) to (4);
a binder; and
a solvent;

in the above formula (2), Rf 1 and Rf 2 each represent a linear or branched perfluoroalkyl group having 1 to 6 carbon atoms, which are the same as or different from each other; Rf 3 represents a linear or branched perfluoroalkylene group having 1 to 6 carbon atoms;
in the above formulas (3) and (4), Rf 4 , Rf 5 , and Rf 6 each represent a linear or branched perfluoroalkylene group having 1 to 6 carbon atoms, which are the same as or different from each other; Z includes any one of an oxygen atom, a nitrogen atom, a CF 2 group, and a CF group;
in the above formulas (2) and (4), R represents a linking group which is a divalent organic group;
in the above formulas (2) to (4), X is any one hydrophilicity imparting group selected from the group consisting of anion type hydrophilicity imparting groups, cation type hydrophilicity imparting groups, and amphoteric type hydrophilicity imparting groups;
the anion type hydrophilicity imparting groups have —CO 2 M 1 , —SO 3 M 1 , —OSO 3 M 1 , —OP(OH)O 2 M 1 , —OPO 3 M 1 2 , ═O 2 PO 2 M 1 , or —PO(OH) y (OM 1 ) 2-y at the terminal,
wherein M 1 represents an alkali metal, an alkali earth metal, Mg, Al, or R 1 R 2 R 3 R 4 N + ; R 1 to R 4 are hydrogen atoms or each independently a linear or branched alkyl group having 1 to 20 carbon atoms, and preferably having 1 to 10 carbon atoms, and y represents an integer of 0 to 2 and
the above-described structure of the terminal shows a case where M 1 is monovalent, and in a case where M 1 is divalent, two identical anions are bonded to M 1 , or two different types of anions are bonded to M 1 ;
the cation type hydrophilicity imparting groups have —N + R 5 R 6 R 7 .Cl − , —N + R 5 R 6 R 7 . Br − , —N + R 5 R 6 R 7 .I − , —N + R 5 R 6 R 7 .CH 3 SO 3 − , —N + R 5 R 6 R 7 .R 7 SO 4 − , —N + R 5 R 6 R 7 .NO 3 − , (—N + R 5 R 6 R 7 ) 2 CO 3 2− , or (—N + R 5 R 6 R 7 ) 2 SO 4 2− at the terminal,
wherein R 5 to R 7 are hydrogen atoms or each independently a linear or branched alkyl group having 1 to 20 carbon atoms, and preferably having 1 to 10 carbon atom; and
the amphoteric type hydrophilicity imparting group has a carboxy betaine type —N + R 8 R 9 (CH 2 ) n CO 2 − , a sulfobetaine type —N + R 8 R 9 (CH 2 ) n SO 3 − , an amine oxide type —N + R 8 R 9 O − , or phosphobetaine type —OPO 3 − (CH 2 ) n N + R 8 R 9 R 10 at the terminal,
wherein n is an integer of 1 to 5, R 8 and R 9 are hydrogen atoms or alkyl groups having 1 to 10 carbon atoms, and R 10 is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms or an alkylene group having 1 to 10 carbon atoms.

2. The surface coating material according to claim 1 ,
wherein the mass composition ratio between the fluorine-based compound and the solvent is within a range of 0.05 to 50:99.95 to 50.

3. The surface coating material according to claim 1 ,
wherein the binder includes any one of a resin, and water glass.

4. The surface coating material according to claim 3 , wherein the resin is a water soluble resin.

5. The surface coating material according to claim 1 ,
wherein the mass composition ratio between the fluorine-based compound and the binder is within a range of 0.2 to 99.9:99.8 to 0.1.

6. The surface coating material according to claim 1 ,
wherein the solvent is water, an organic solvent, or a mixture of water and an organic solvent.

7. A coating film, comprising:
one or more fluorine-based compounds represented by the formulas (2) to (4) in claim 1 ; and
a binder.

8. A hydrophilic oil repellent member, comprising:
a substrate; and
a hydrophilic oil repellent layer provided on a part or all of the surface of the substrate,
wherein the hydrophilic oil repellent layer includes one or more fluorine-based compounds represented by the formulas (2) to (4) in claim 1 .

9. The hydrophilic oil repellent member according to claim 8 ,
wherein the hydrophilic oil repellent layer further includes a binder.

10. The hydrophilic oil repellent member according to claim 9 ,
wherein the binder is an organic binder or an inorganic binder.

11. The hydrophilic oil repellent member according to claim 8 ,
wherein the substrate is any one or a combination of two or more selected from the group consisting of glass, plastic, metal, ceramics, stainless steel, aluminum, wood, stone, cement, concrete, fiber, cloth, paper, and leather.

12. The hydrophilic oil repellent member according to claim 8 ,
wherein the substrate is a PET film or a glass plate.

13. The hydrophilic oil repellent member according to claim 12 ,
wherein the total light transmittance is 90% or greater.

14. The hydrophilic oil repellent member according to claim 8 ,
wherein a static contact angle for water on the surface of the substrate provided with a hydrophilic oil repellent layer is 15° or less, and a static contact angle for hexadecane is 65° or greater.

15. The hydrophilic oil repellent member according to claim 8 ,
wherein the substrate is a kitchen utensil used in a kitchen or a sanitary utensil used in a sanitary facility.

16. The hydrophilic oil repellent member according to claim 8 ,
wherein the substrate is an oil contamination protection tool for preventing sticking of oils.

17. A surface coating material which forms a hydrophilic oil repellent layer on at least a part of the surface of a substrate, comprising:
one or more fluorine-based compounds represented by the following formulas (1);
a binder; and
a solvent;

wherein in the above formulas (1), Rf 1 and Rf 2 each represents a linear or branched perfluoroalkyl group having 1 to 6 carbon atoms, which are the same as or different from each other, and Rf 3 represents a linear or branched perfluoroalkylene group having 1 to 6 carbon atoms;
in the above formulas (1), X represents anion type hydrophilicity imparting groups and
the anion type hydrophilicity imparting groups have CO 2 M 1 , OP(OH)O 2 M 1 , OPO 3 M 1 2 , ═O 2 PO 2 M 1 , or PO(OH) y (OM 1 ) 2-y , wherein M 1 represents an alkali metal, an alkali earth metal, Mg, Al, or R 1 R 2 R 3 R 4 N + ; R 1 to R 4 -are each independently a hydrogen atom or a linear or branched alkyl group having 1 to 20 carbon atoms, and preferably having 1 to 10 carbon atoms, and y represents an integer of 0 to 2;
wherein the above-described structure of the terminal shows a case where M 1 is monovalent, and in a case where M 1 is divalent, two identical anions are bonded to M 1 , or two different types of anions are bonded to M 1 .

18. The surface coating material according to claim 17 ,
wherein the mass composition ratio between the fluorine-based compound and the solvent is within a range of 0.05 to 50:99.95 to 50.

19. The surface coating material according to claim 17 ,
wherein the binder includes any one of a resin, and water glass.

20. The surface coating material according to claim 17 ,
wherein the mass composition ratio between the fluorine-based compound and the binder is within a range of 0.2 to 99.9:99.8 to 0.1.

Assignees

• Mitsubishi Materials Corp
• Mitsubishi Mat Electronic Chemicals Co Ltd

Inventors

• Uotani Masakazu
• Koshiyama Hiroshi
• Kamiya Takeshi
• Honda Tsunetoshi
• Sato Kosei
• Fujita Masato
• Takano Daisuke

Classifications

• A41D19/01558

  using a layer of grip improving material (A41D19/01552 takes precedence) · CPC title

• C09D201/00

  Coating compositions based on unspecified macromolecular compounds · CPC title

• C09D5/00

  Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced {(electrically insulating plastics, resins or waxes H01B3/30)}; Filling pastes · CPC title

• C09D7/40

  Additives · CPC title

• A43B7/12

  Special watertight footwear (overshoes A43B3/16) · CPC title