# US 2010/0167168 A1 · Hydrophilic Adjuvant

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- Number: US 2010/0167168 A1
- Document ID: US20100167168A1
- Status: Published application
- Kind: A1
- Application number: 12/086,519
- Filed: 2006-12-15
- Published: 2010-07-01
- Earliest claimed: 2005-12-15
- Assignees: LG Chem, Ltd.
- Inventors: Dong-Pyo Kim; Lan-Young Hong; Jung Hye Won; Yong Su Park; Chong Kyu Shin
- Web page: https://patentgrep.com/patent/US20100167168A1

## CPC

- C09K 3/18: for application to surfaces to minimize adherence of ice, mist or water thereto (rendering particulate materials free flowing, in general, e.g. making them hydrophobic B01J2/30); Thawing or antifreeze materials for application to surfaces (used in liquids for heat-transfer, heat-exchange or heat-storage or for the production of heat or cold other than by combustion, e.g. radiator liquids, C09K5/00)
- C09D 7/45: Anti-settling agents
- C09D 7/62: modified by treatment with other compounds
- C08K 3/22: of metals
- C08K 7/24: inorganic
- C08K 9/04: Ingredients treated with organic substances {(treated with macromolecular compounds C08K9/08)}
- Y10T 428/13: Hollow or container type article [e.g., tube, vase, etc.]
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION

## Abstract

Disclosed is an adjuvant capable of imparting a hydrophilic or superhydrophilic function to various materials or interfaces. The hydrophilic adjuvant comprises: a composite metal oxide containing Si and at least one metal element selected from the group consisting of Ti(IV), Zr(IV), Sn(IV) and Al(III); and a hydrophilic group-containing organic compound physically or chemically bonded with the Ti(IV), Zr(IV), Sn(IV) or Al of the composite metal oxide.

## Claims

### Claim 1

A hydrophilic adjuvant comprising:
a composite metal oxide containing Si and at least one metal element selected from the group consisting of Ti(IV), Zr(IV), Sn(IV) and Al(III); and
a hydrophilic group-containing organic compound physically or chemically bonded with the Ti(IV), Zr(IV), Sn(IV) or Al of the composite metal oxide.

### Claim 2 (depends on 1)

The hydrophilic adjuvant of claim 1, wherein the composite metal oxide has a meso-porous structure.

### Claim 3 (depends on 2)

The hydrophilic adjuvant of claim 2, wherein the composite metal oxide has a hollow tubular meso-porous structure.

### Claim 4 (depends on 3)

The hydrophilic adjuvant of claim 3, wherein the hydrophilic group-containing organic compound is physically or chemically bonded inside the hollow of the composite metal oxide having the hollow tubular meso-porous structure.

### Claim 5 (depends on 1)

The hydrophilic adjuvant of claim 1, wherein the hydrophilic group of the hydrophilic group-containing organic compound is selected from the group consisting of sulfonate salt, sulfonic acid, carboxylate salt, carboxylic acid, phosphate salt, phosphoric acid and hydroxy (OH).

### Claim 6 (depends on 1)

The hydrophilic adjuvant of claim 1, wherein the hydrophilic group-containing organic compound contains a functional group selected from the group consisting of hydroxy (OH), amine and phosphate, which are functional groups capable of forming a physical or chemical bond with the Ti(IV), Zr(IV), Sn(IV) or Al of the composite metal oxide.

### Claim 7 (depends on 1)

The hydrophilic adjuvant of claim 1, wherein the hydrophilic group-containing organic compound is a chelating agent capable of forming a coordination bond with the Ti(IV), Zr(IV), Sn(IV) or Al of the composite metal oxide.

### Claim 8 (depends on 1)

The hydrophilic adjuvant of claim 1, wherein the hydrophilic group-containing organic compound is selected from the group consisting of disodium 1,2-dihydroxybenzene-3,5-disulfonate, sodium 1,2-dihydroxy-3-sulfonate, sodium 1,2-dihydroxy-4-sulfonate, sodium 1,2-dihydroxy-5-sulfonate, disodium 1,2-dihydroxy-4-chlorobenzene-3,5-disulfonate, disodium 1,2-dihydroxy-6-chlorobenzene-3,5-disulfonate, 1,2-dihydroxybenzene-3,5-disulfonic acid, 1,2-dihydroxy-3-sulfonic acid, 1,2-dihydroxy-4-sulfonic acid, 1,2-dihydroxy-5-sulfonic acid, 1,2-dihydroxy-4-chlorobenzene-3,5-disulfonic acid, 1,2-dihydroxy-6-chlorobenzene-3,5-disulfonic acid, disodium 1,2-dihydroxybenzene-3,5-dicarboxylate, sodium 1,2-dihydroxy-3-carboxylate, sodium 1,2-dihydroxy-4-carboxylate, sodium 1,2-dihydroxy-5-carboxylate, disodium 1,2-dihydroxy-4-chlorobenzene-3,5-dicarboxylate, disodium 1,2-dihydroxy-6-chlorobenzene-3,5-dicarboxylate, 1,2-dihydroxybenzene-3,5-dicarboxylic acid, 1,2-dihydroxy-3-carboxylic acid, 1,2-dihydroxy-4-carboxylic acid, 1,2-dihydroxy-5-carboxylic acid, 1,2-dihydroxy-4-chlorobenzene-3,5-dicarboxylic acid, 1,2-dihydroxy-6-chlorobenzene-3,5-dicarboxylic acid, disodium 1,2-dihydroxybenzene-3,5-diphosphate, sodium 1,2-dihydroxy-3-phosphate, sodium 1,2-dihydroxy-4-phosphate, sodium 1,2-dihydroxy-5-phosphate, disodium 1,2-dihydroxy-4-chlorobenzene-3,5-diphosphate, disodium 1,2-dihydroxy-6-chlorobenzene-3,5-diphosphate, 1,2-dihydroxybenzene-3,5-diphosphoric acid, 1,2-dihydroxybenzene-3-phosphoric acid, 1,2-dihydroxybenzene-4-phosphoric acid, 1,2-dihydroxybenzene-5-phosphoric acid, 1,2-dihydroxy-4-chlorobenzene-3,5-diphosphoric acid, 1,2-dihydroxy-6-chlorobenzene-3,5-diphosphoric acid, dihexadecyl phosphate, monododecylphosphate, and Nafion (tetrafluoroethylene-perfluoro-3,6-dioxa-4-methyl-7-octenesulfonic acid copolymer).

### Claim 9 (depends on 1)

The hydrophilic adjuvant of claim 1, wherein the composite metal oxide is formed by:
(1) hydrolyzing a silane compound represented by Formula 1 to form a silica dispersion, adding thereto a compound represented by Formula 2, or a mixture thereof, and subjecting the resulting dispersion to a polymerization reaction; or
(2) polymerizing the silane compound represented by Formula 1 with the compound represented by Formula 2, or a mixture thereof:
R′4−nSiRn [Formula 1]
wherein R is independently selected from among C1-C6 alkoxy, hydroxy (OH) and halogen elements, n is an integer of 1-4, and R′ is independently selected from among C1-C6 alkyl containing or not containing an unsaturated functional group, vinyl and hydrogen (H); and
AaBbOc [Formula 2]
wherein A is Ti(IV), Zr(IV), Sn(IV) or Al(III), B is halogen, hydroxy (OH), C1-C6 alkoxy, or C5-C10 β-diketonate, a is 1 or 2, b is 4, 3 or 2, and c is 0 or 1.

### Claim 10 (depends on 2)

The hydrophilic adjuvant of claim 2, wherein the composite metal oxide having the mesoporous structure is formed by polymerizing a precursor(s) containing at least one element selected from the group consisting of Si, Ti(IV), Zr(IV), Sn(IV) and Al(III), in the presence of a solvent and a surfactant.

### Claim 11 (depends on 10)

The hydrophilic adjuvant of claim 10, wherein the solvent is one or more selected from the group consisting of ethanol, water, isopropyl alcohol, methanol and ethyl acetate.

### Claim 12 (depends on 10)

The hydrophilic adjuvant of claim 10, wherein the surfactant is a nonionic surfactant represented by Formula 3 or an ionic surfactant represented by Formula 4:
EOxPOyEOx [Formula 3]
wherein x=5-40%, y=90-20%, 2x+y=100%, EO=ethylene oxide, and PO=propylene oxide; and
(CnH2n+1)(CH3)3NX1 [Formula 4]
wherein n=12-18, and X1═Cl or Br.

### Claim 13 (depends on 1)

The hydrophilic adjuvant of claim 1, further comprising a silane coupling agent.

### Claim 14 (depends on 3)

The hydrophilic adjuvant of claim 3, wherein the silane coupling agent is a compound represented by Formula 5, or a mixture thereof:
(R1(CH2)m)dSi(OR2)4−d, [Formula 5]
wherein m is an integer of 0-5, d is an integer of 1-3, R1 is selected from among (meth)acrylate, vinyl, epoxy, amine, hydroxy, benzyl, phenyl and glycidoxypropyl, R2 is C1-C5 hydrocarbon.

### Claim 15 (depends on 13)

The hydrophilic adjuvant of claim 13, further comprising a multifunctional organic compound represented by Formula 6:
R3(EO)kR4 [Formula 6]
wherein EO is ethylene oxide, k is an integer of 3-400, R3 is selected from among OH, C1-C15 (meth)acrylate, C1-C15 di(meth)acrylate, C1-C15 tri(meth)acrylate and C1-C15 vinyl, and R4 is selected from among hydrogen, C1-C3 (meth)acrylate and C1-C3 vinyl.

### Claim 16 (depends on 15)

The hydrophilic adjuvant of claim 15, wherein the silane coupling agent, the multifunctional organic compound, or both, is bound to the composite metal oxide.

### Claim 17 (depends on 1)

The hydrophilic adjuvant of claim 1, which is used as one component of a coating solution to be coated on a substrate.

### Claim 18 (depends on 1)

The hydrophilic adjuvant of claim 1, which is used as one component of a film formulation in a film forming process.

### Claim 19 (depends on 1)

A substrate having a coating layer formed using a hydrophilic adjuvant set forth in claim 1.

### Claim 20 (depends on 19)

The substrate of claim 19, which has anti-fog performance due to the hydrophilic adjuvant.

### Claim 21 (depends on 19)

The substrate of claim 19, which is an optical lens.

### Claim 22 (depends on 1)

An electrolyte membrane in which a hydrophilic adjuvant set forth in claim 1 is used as one component of a coating solution for forming an electrolyte membrane or as one component of an electrolyte membrane-forming formulation.

### Claim 23 (depends on 22)

The electrolyte membrane of claim 22, which is an electrolyte membrane for fuel cells.

### Claim 24 (depends on 1)

An electrolyte for fuel cells, which contains a hydrophilic adjuvant set forth in claim 1, and an electrode catalyst.