Hydrophilic oil repellent and production method of same, surface coating material, coating film, resin composition, oil-water separation filter material, and porous body

Patent metadata

Field	Value
Publication number	US-10208210-B2
Application number	US-201515329408-A
Country	US
Kind code	B2
Filing date	Jul 29, 2015
Priority date	Jul 30, 2014
Publication date	Feb 19, 2019
Grant date	Feb 19, 2019

Abstract

The hydrophilic oil repellent includes one or more types of nitrogen-containing fluorine-based compounds. The nitrogen-containing fluorine-based compound includes 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 in the molecule.

First claim

The invention claimed is:

1. A hydrophilic oil repellent, comprising:
one or more nitrogen-containing fluorine-based compounds represented by the following formulas (1) to (4):

wherein in the above formulas (1) and (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, and 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, and 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; and
in the above formulas (1) to (4), X is:
an anion type hydrophilic imparting group having “—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 ,” wherein M 1 represents an alkali metal, an alkali earth metal, Mg, Al, or R 1 R 2 R 3 R 4 N + , and wherein 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 y represents an integer of 0 to 2, at a terminal, or
a cation type hydrophilicity imparting group having “—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− ”, wherein R 5 to R 7 are hydrogen atoms or each independently a linear or branched alkyl group having 1 to 20 carbon atoms, at a terminal,
or
an amphoteric hydrophilicity imparting group having any one terminal of a carboxybetaine type, a sulfobetaine type, an amine oxide type, and a phosphobetaine type.

2. A production method of the hydrophilic oil repellent according to claim 1 ,
wherein a carboxylic acid halide or a sulfonic acid halide having a nitrogen-containing perfluoroalkyl group represented by the following formula (5) or (6) is used as a raw material:

wherein in the above formula (5), 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, and Rf 3 represents a linear or branched perfluoroalkylene group having 1 to 6 carbon atoms;
in the above formula (6), 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, and Z includes any one of an oxygen atom, a nitrogen atom, a CF 2 group, and a CF group;
in the above formulas (5) and (6), Y represents CO or SO 2 ; and
in the above formulas (5) and (6), A represents any one halogen atom selected from the group consisting of fluorine, chlorine, bromine, and iodine.

3. A surface coating material, comprising:
the hydrophilic oil repellent according to claim 1 ; and
a solvent,
wherein the mass composition ratio between the hydrophilic oil repellent and the solvent is within a range of 0.2 to 50:99.8 to 50.

4. The surface coating material according to claim 3 ,
wherein the solvent is water, an alcohol, or a mixture of water and an alcohol.

5. The surface coating material according to claim 3 , further comprising:
a binder,
wherein the mass composition ratio between the hydrophilic oil repellent 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 3 ,
wherein the binder includes any one of a resin, and water glass.

7. The surface coating material according to claim 6 , wherein the resin is a water soluble resin.

8. A coating film, comprising:
the hydrophilic oil repellent according to claim 1 .

9. The coating film according to claim 8 , further comprising:
a binder,
wherein the mass composition ratio between the hydrophilic oil repellent and the binder is within a range of 0.2 to 99.9:99.8 to 0.1.

10. An oil-water separation filter material, comprising:
any one or more of the coating film according to claim 8 .

11. A resin composition, comprising:
the hydrophilic oil repellent according to claim 1 ; and
a resin,
wherein the mass composition ratio between the hydrophilic oil repellent and the resin is within a range of 0.2 to 99.9:99.8 to 0.1.

12. A porous body, comprising:
the hydrophilic oil repellent according to claim 1 .

13. A porous body,
wherein the hydrophilic oil repellent according to claim 1 is bonded with a resin or a vitreous material.

Assignees

• Mitsubishi Materials Corp
• Mitsubishi Mat Electronic Chemicals Co Ltd

Inventors

• Fujita Masato
• Uotani Masakazu
• Kamiya Takeshi
• Honda Tsunetoshi
• Takano Daisuke

Classifications

• C07C309/04

  containing only one sulfo group · CPC title

• C02F1/40

  Devices for separating or removing fatty or oily substances or similar floating material (cleaning or keeping clear the surface of open water from oil or like materials E02B15/04; devices in sewers for separating liquid or solid substances from sewage E03F5/14, e.g. for use in drains leading to the sewer E03F5/16) · CPC title

• C07C303/38

  by reaction of ammonia or amines with sulfonic acids, or with esters, anhydrides, or halides thereof · CPC title

• C09D5/16

  Antifouling paints; Underwater paints · CPC title

• C08L101/00

  Compositions of unspecified macromolecular compounds · CPC title