# US 11,028,287 B2 · Moisture-curable omniphobic coatings

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- Number: US 11,028,287 B2
- Document ID: US11028287B2
- Status: Granted
- Kind: B2
- Application number: 15/903,386
- Filed: 2018-02-23
- Published: 2019-01-31
- Granted: 2021-06-08
- Earliest claimed: 2017-03-03
- Assignees: The Government of the United States of America, as represented by the Secretary of the Navy
- Applicants: The Government of the United States of America, as represented by the Secretary of the Navy
- Inventors: Erick B. Iezzi
- Web page: https://patentgrep.com/patent/US11028287B2

## CPC

- C09D 183/08: containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
- C08G 18/0885: {using additives, e.g. absorbing agents}
- C08G 18/289: {containing silicon}
- C08G 18/3893: {containing silicon}
- C08G 18/73: acyclic
- C08G 18/792: {formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates}
- C08G 18/837: {by silicon containing compounds}
- C08L 75/02: Polyureas
- C09D 5/00: 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
- C09D 175/02: Polyureas
- C23C 26/00: Coating not provided for in groups C23C2/00 - C23C24/00
- C08G 2150/00: Compositions for coatings
- 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)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- C23C: COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL (making metal-coated products by extrusion B21C23/22; covering with metal by connecting pre-existing layers to articles, see the relevant places, e.g. B21D39/00, B23K; metallising of glass C03C; metallising mortars, concrete, artificial stone, ceramics or natural stone C04B41/00; enamelling of, or applying a vitreous layer to, metals C23D; treating metal surfaces or coating of metals by electrolysis or electrophoresis C25D; single-crystal film growth C30B; by metallising textiles D06M11/83; decorating textiles by locally metallising D06Q1/04)

## Abstract

An omniphobic material and its method of making by: providing an alkoxysilane-terminated polyurea, and reacting by a moisture-curing reaction the polyurea and a fluorinated material having one or more alkoxy or hydroxyl groups.

## Claims

### Claim 1

A composition comprising a polymer made by a method comprising:
providing an alkoxysilane-terminated polyurea;
wherein the alkoxysilane-terminated polyurea is a reaction product of a mixture consisting of an aliphatic polyisocvanate having at least 2 isocyanate groups and an amino-functional alkoxysilane of the formula NH(R3)(CH2)nSi(R2)x(OR1)3-x; wherein x is 1, 2, or 3; wherein x is 0, 1, or 2;
wherein each R1 and R2 is an alkyl group; and
wherein R3 is aryl, alkyl, an ester-containing alkyl, or a fluorinated alkyl group; and
reacting by a moisture-curing reaction the polyurea and a fluorinated material having one or more alkoxy or hydroxyl groups.

### Claim 2 (depends on 1)

The composition of claim 1;
wherein the fluorinated material is a fluoroalkyl alkoxysilane having the formula
(R4O)3Si(CX2)nCX3;
wherein each X is —H or —F;
wherein at least one X is —F; and
wherein each R4 is —H or an alkyl group.

### Claim 3 (depends on 2)

The composition of claim 2, wherein the fluoroalkyl alkoxysilane comprises a perfluoroalkyl group.

### Claim 4 (depends on 2)

The composition of claim 2, wherein the fluoroalkyl alkoxysilane is (3,3,3-trifluoropropyl)trimethoxysilane, nonafluorohexyltrimethoxysilane, (tridecafluoro-1,1,2,2-tetrahydrooctyl)triethoxysilane, (tridecafluoro-1,1,2,2-tetrahydrooctyl)trimethoxysilane, perfluorododecyl-1H,1H,2H,2H-triethoxysilane, perfluorotetradecyl-1H,1H,2H,2H-triethoxysilane, triethoxy(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-1-octyl)silane, [perfluoro(polypropyleneoxy)] methoxypropyltrimethoxysilane, or a combination thereof.

### Claim 5 (depends on 1)

The composition of claim 1, wherein the fluorinated material is a reaction product of a fluoroalkyl alkoxysilane and fumed silica.

### Claim 6 (depends on 1)

The composition of claim 1, wherein the fluorinated material is a reaction product of a fluoroalkyl alkoxysilane and a hydroxyl-functional polymeric particle.

### Claim 7 (depends on 1)

The composition of claim 1, wherein the fluorinated material is a fluorinated organic polymer with hydroxyl functionality.

### Claim 8 (depends on 1)

The composition of claim 1, wherein the fluorinated material is a fluorinated silicone polymer with hydroxyl functionality.

### Claim 9 (depends on 1)

The composition of claim 1, wherein the reaction includes up to 50 wt % of the fluorinated material.

### Claim 10 (depends on 1)

The composition of claim 1, further comprising:
a reactive diluent, an alkyl-functional alkoxysilane, tetraethoxysilane, tetramethoxysilane, or an alkoxy-functional polysiloxane.

### Claim 11 (depends on 1)

The composition of claim 1, further comprising:
an amino-functional alkoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-aminopropylmethyldiethoxysilane, or N-methyl-3-aminopropyltrimethoxysilane.

### Claim 12 (depends on 1)

The composition of claim 1, further comprising:
a catalyst, a filler, a solvent, a pigment, a wetting/dispersing agent, a flow/leveling agent, or a thickening agent.

### Claim 13 (depends on 1)

The composition of claim 1, further comprising:
a reactive diluent, an alkyl-functional alkoxysilane, tetraethoxysilane, tetramethoxysilane, an alkoxy-functional polysiloxane, a catalyst, a filler, a solvent, a pigment, a wetting/dispersing agent, a flow/leveling agent, or a thickening agent.

### Claim 14

A method comprising:
providing a composition comprising:
an alkoxysilane-terminated polyurea;
wherein the alkoxysilane-terminated polyurea is a reaction product of a mixture consisting of an aliphatic polyisocyanate having at least 2 isocyanate groups and an amino-functional alkoxysilane of the formula NH(R3)(CH2)nSi(R2)x(OR1)3−x; wherein n is 1, 2, or 3; wherein x is 0, 1, or 2;
wherein each R1 and R2 is an alkyl group; and
wherein R3 is aryl, alkyl, an ester-containing alkyl, or a fluorinated alkyl group;
and
a second amino-functional alkoxysilane selected from the group consisting of 3-aminopropyltrimethoxysilane, 3-aminopropyltri ethoxy silane, 3-aminopropylmethyldi ethoxy silane, or N-methyl-3-aminopropyltrimethoxysilane; and
reacting by a moisture-curing reaction the polyurea and a fluorinated material having one or more alkoxy or hydroxyl groups.

### Claim 15

A method comprising:
providing an alkoxysilane-terminated polyurea;
wherein the alkoxysilane-terminated polyurea is a reaction product of a mixture consisting of an aliphatic polyisocvanate having at least 2 isocyanate groups and an amino-functional alkoxysilane of the formula NH(R3)(CH2)nSi(R2)x(OR1)3-x; wherein n is 1, 2, or 3; wherein x is 0, 1, or 2;
wherein each R1 and R2 is an alkyl group; and
wherein R3 is aryl, alkyl, an ester-containing alkyl, or a fluorinated alkyl group; and
reacting by a moisture-curing reaction the polyurea and a fluorinated material having one or more alkoxy or hydroxyl groups.

### Claim 16 (depends on 15)

The method of claim 15;
wherein the fluorinated material is a fluoroalkyl alkoxysilane having the formula
(R4O)3Si(CX2)nCX3;
wherein each X is —H or —F;
wherein at least one X is —F; and
wherein each R4 is —H or an alkyl group.

### Claim 17 (depends on 16)

The method of claim 16, wherein the fluoroalkyl alkoxysilane comprises a perfluoroalkyl group.

### Claim 18 (depends on 16)

The method of claim 16, wherein the fluoroalkyl alkoxysilane is (3,3,3-trifluoropropyl)trimethoxysilane, nonafluorohexyltrimethoxysilane, (tridecafluoro-1,1,2,2-tetrahydrooctyl)triethoxysilane, (tridecafluoro-1,1,2,2-tetrahydrooctyl)trimethoxysilane, perfluorododecyl-1H,1H,2H,2H-triethoxysilane, perfluorotetradecyl-1H,1H,2H,2H-triethoxysilane, triethoxy(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-1-octyl)silane, [perfluoro(polypropyleneoxy)] methoxypropyltrimethoxysilane, or a combination thereof.

### Claim 19 (depends on 15)

The method of claim 15, wherein the fluorinated material is a reaction product of a fluoroalkyl alkoxysilane and fumed silica.

### Claim 20 (depends on 15)

The method of claim 15, wherein the fluorinated material is a reaction product of a fluoroalkyl alkoxysilane and a hydroxyl-functional polymeric particle.

### Claim 21 (depends on 15)

The method of claim 15, wherein the fluorinated material is a fluorinated organic polymer with hydroxyl functionality.

### Claim 22 (depends on 15)

The method of claim 15, wherein the fluorinated material is a fluorinated silicone polymer with hydroxyl functionality.

### Claim 23 (depends on 15)

The method of claim 15, wherein the reaction includes up to 50 wt % of the fluorinated material.

### Claim 24 (depends on 15)

The method of claim 15, further comprising:
applying the alkoxysilane-terminated polyurea and the fluorinated material to a substrate by a spray, brush, roll, or dip method.

### Claim 25 (depends on 24)

A coating made by the method of claim 24.

### Claim 26 (depends on 14)

The method of claim 14;
wherein the fluorinated material is a fluoroalkyl alkoxysilane having the formula
(R4O)3Si(CX2)nCX3;
wherein each X is —H or —F;
wherein at least one X is —F; and
wherein each R4 is —H or an alkyl group.

### Claim 27

A composition comprising:
a polymer made by a method comprising;
providing an alkoxysilane-terminated polyurea;
wherein the alkoxysilane-terminated polyurea is a reaction product of a mixture consisting of an aliphatic polyisocyanate having at least 2 isocyanate groups and an amino-functional alkoxysilane of the formula NH(R3)(CH2)nSi(R2)x(OR1)3-x; wherein n is 1, 2, or 3; wherein x is 0, 1, or 2;
wherein each R1 and R2 is an alkyl group; and
wherein R3 is aryl, alkyl, an ester-containing alkyl, or a fluorinated alkyl group; and
reacting by a moisture-curing reaction the polyurea and a fluorinated material having one or more alkoxy or hydroxyl groups; and an amino-functional alkoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-aminopropylmethyldiethoxysilane, or N-methyl-3-aminopropyltrimethoxysilane.

### Claim 28 (depends on 27)

The composition of claim 27;
wherein the fluorinated material is a fluoroalkyl alkoxysilane having the formula
(R4O)3Si(CX2)nCX3;
wherein each X is —H or —F;
wherein at least one X is —F; and
wherein each R4 is —H or an alkyl group.

### Claim 29 (depends on 27)

The composition of claim 27, wherein the fluorinated material is a reaction product of a fluoroalkyl alkoxysilane and fumed silica, a reaction product of a fluoroalkyl alkoxysilane and a hydroxyl-functional polymeric particle, a fluorinated organic polymer with hydroxyl functionality, or a fluorinated silicone polymer with hydroxyl functionality.

### Claim 30 (depends on 14)

The method of claim 14, wherein the fluorinated material is a reaction product of a fluoroalkyl alkoxysilane and fumed silica, a reaction product of a fluoroalkyl alkoxysilane and a hydroxyl-functional polymeric particle, a fluorinated organic polymer with hydroxyl functionality, or a fluorinated silicone polymer with hydroxyl functionality.

### Claim 31 (depends on 14)

The method of claim 14, further comprising:
applying the alkoxysilane-terminated polyurea and the fluorinated material to a substrate by a spray, brush, roll, or dip method.

### Claim 32 (depends on 31)

A coating made by the method of claim 31.

### Claim 33 (depends on 1)

The polymer of claim 1, wherein the aliphatic polyisocyanate is a hexamethylene diisocyanate trimer.

### Claim 34 (depends on 15)

The method of claim 15, wherein the aliphatic polyisocyanate is a hexamethylene diisocyanate trimer.