Methods of material hydrophilization by siloxanes containing nitrilopoly (methylenephosphonic acid) or derivatives thereof

Patent metadata

Field	Value
Publication number	US-9314816-B2
Application number	US-201213708682-A
Country	US
Kind code	B2
Filing date	Dec 7, 2012
Priority date	Dec 7, 2011
Publication date	Apr 19, 2016
Grant date	Apr 19, 2016

Abstract

A method of imparting hydrophilicity to a surface of a material, which comprises providing a base material comprising a surface; applying and chemically fixing a siloxane oligomer represented by Chemical Formula 1 to the surface of the base material to form a siloxane-modified surface; and applying a phosphonic acid compound represented by Chemical Formula 2 to the siloxane-modified surface and carrying out a reaction therebetween to form an organosiloxane coating:

wherein in Chemical Formula 1,
R 1 , R 2 , and R 3 are the same or different, and are each independently hydrogen or a C1 to C3 alkyl group,
A is a single bond or a C1 to C5 alkylene group, and
n ranges from 2 to 30;

GN[CH 2 PO 3 H 2 ] 2   Chemical Formula 2

wherein in Chemical Formula 2,
G is —CH 2 PO 3 H 2 , a group represented by Chemical Formula 3, or a group represented by Chemical Formula 4 as defined herein.

First claim

What is claimed is:

1. A method of imparting hydrophilicity to a surface of a material, which comprises:
providing a base material comprising a surface;
applying and chemically fixing a siloxane oligomer represented by Chemical Formula 1 to the surface of the base material to form a siloxane-modified surface; and
applying a phosphonic acid compound represented by Chemical Formula 2 to the siloxane-modified surface and carrying out a reaction therebetween to form an organosiloxane coating:

wherein in Chemical Formula 1,
R 1 , R 2 , and R 3 are the same or different, and are each independently hydrogen or a C1 to C3 alkyl group,
A is a single bond or a C1 to C5 alkylene group, and
n ranges from 2 to 30;
GN[CH 2 PO 3 H 2 ] 2   Chemical Formula 2

wherein in Chemical Formula 2,
G is —CH 2 PO 3 H 2 , a group represented by Chemical Formula 3, or a group represented by Chemical Formula 4:

wherein in Chemical Formula 3,
m is an integer ranging from 2 to 8; and

wherein in Chemical Formula 4,
a and b are the same or different and are each independently integers ranging from 2 to 6.

2. The method of claim 1 , wherein the base material is an organic material, an inorganic material, or an organic-inorganic hybrid material, and comprises a hydroxyl group, a carboxyl group, or a combination thereof on the surface thereof.

3. The method of claim 2 , further comprising subjecting the base material to a corona treatment, an ultraviolet (UV) treatment, a plasma treatment, or a chemical treatment using hydrogen peroxide, hexafluoride isopropanol, or an acid to have a hydroxyl group, a carboxyl group, or a combination thereof on its surface before applying and chemically fixing the siloxane oligomer represented by Chemical Formula 1 to the surface of the base material.

4. The method of claim 1 , wherein the siloxane oligomer represented by Chemical Formula 1 is oligo(aminopropyl)ethoxysilane, oligo(aminopropyl)methoxysilane, oligo(aminoethyl)methoxysilane, oligo(aminoethyl)ethoxysilane, oligo(aminobutyl)ethoxysilane, oligo(aminobutyl)methoxysilane, oligo(aminopentyl)ethoxysilane, oligo(aminopentyl)methoxysilane, or a combination thereof.

5. The method of claim 1 , wherein the siloxane oligomer represented by Chemical Formula 1 has an n value ranging from 4 to 16.

6. The method of claim 1 , wherein the phosphonic acid compound represented by Chemical Formula 2 is nitrilotri(methylenephosphonic acid), ethylenebis(nitrilodimethylene)tetraphosphonic acid, hexamethylenediamine-N,N,N′,N′-tetrakis(methylphosphonic acid), diethylenetriaminepentakis(methylphosphonic acid) a derivative of the foregoing phosphonic acid compounds, or a combination thereof.

7. The method of claim 1 , wherein the applying and chemically fixing the siloxane oligomer to the surface of the base material comprises wetting the surface of the base material with a solution comprising the siloxane oligomer to provided a wetted surface, and drying, heating, or drying and heating the wetted surface.

8. The method of claim 7 , wherein preparing the solution comprising the siloxane oligomer comprises dissolving the siloxane oligomer represented by Chemical Formula 1 in a C1 to C10 alcohol in an amount of about 0.05 to about 10 wt % based on a total weight of the solution.

9. The method of claim 8 , wherein the applying the phosphonic acid compound to the siloxane modified surface and carrying out the reaction therebetween comprises wetting the siloxane modified surface with a solution comprising the phosphonic acid compound to provide a wetted surface, and drying, heating, or drying and heating the wetted surface.

10. The method of claim 9 , wherein preparing the solution comprising the phosphonic acid compound comprises dissolving the phosphonic acid compound represented by Chemical Formula 2 in a C1 to C10 alcohol in an amount of about 1 to about 30 wt % based on a total weight of the solution.

Assignees

• Samsung Electronics Co Ltd

Inventors

• Izmailov Boris Alexandrovich
• Rodlovskaya Elena Nikolaevna
• Markova Galy Dmitrievna
• Baranov Oleg Valerievich
• Vasnev Valeri Alexandrovich
• Jung Won-Cheol

Classifications

• Y10T428/31663

  As siloxane, silicone or silane · CPC title

• Y10T428/31612

  As silicone, silane or siloxane · CPC title

• C09D183/08 Primary

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

• C03C2217/75

  Hydrophilic and oleophilic coatings · CPC title

• C08J7/12

  Chemical modification · CPC title