# US 8,785,679 B2 · Hydrophilic biocidal coatings

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- Number: US 8,785,679 B2
- Document ID: US8785679B2
- Status: Granted
- Kind: B2
- Application number: 13/881,540
- Filed: 2012-12-10
- Published: 2014-06-12
- Granted: 2014-07-22
- Earliest claimed: 2012-12-10
- Assignees: Empire Technology Development LLC
- Applicants: Empire Technology Development LLC
- Inventors: Glen Leon Brizius; Phillip Kent Montgomery
- Web page: https://patentgrep.com/patent/US8785679B2

## CPC

- A01N 47/44: Guanidine; Derivatives thereof
- A01N 57/12: containing acyclic or cycloaliphatic radicals
- C08G 73/0206: {Polyalkylene(poly)amines}
- C08G 73/0226: {Quaternisation of polyalkylene(poly)amines}
- C09D 5/1637: {Macromolecular compounds}
- C09D 133/12: Homopolymers or copolymers of methyl methacrylate
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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)

## Abstract

Hydrophilic, biocidal coating compositions and methods to make and use the compositions are disclosed. The coatings include compounds with quaternary amine polyethylene glycol groups and polyaminoalkyl biguanide groups as substituents. The compounds when incorporated in paints provide hydrophilic, self-cleaning and biocidal property to the coating.

## Claims

### Claim 1

A compound having the formula I
wherein E is phosphorus, bismuth, arsenic or vanadium;
R1 is
wherein A is alkyl, substituted alkyl, cycloalkyl, heteroalkyl, aryl, heteroaryl or substituted aryl;
R2 is —CH2— or —CH(—CH3)—;
R3 is
wherein n is an integer from 2 to 20; and
R4 is H, vinyl, propenyl, butenyl, pentenyl, or hexenyl.

### Claim 2 (depends on 1)

The compound of claim 1, wherein
E is phosphorus;
R1 is
R2 is —CH2—;
R3 is polyaminopropyl biguanide; and
R4 is vinyl.

### Claim 3

A method of making a biocidal compound of formula I,
wherein E is phosphorus, bismuth, arsenic or vanadium;
R1 is
wherein A is alkyl, substituted alkyl, cycloalkyl, heteroalkyl, aryl, heteroaryl, or substituted aryl;
R2 is —CH2— or —CH(—CH3)—;
R3 is
wherein n is an integer from 2 to 20; and
R4 is H, vinyl, propenyl, butenyl, pentenyl, or hexenyl;
the method comprising;
contacting an inorganic halide with an end-capped quaternary amine polyethylene glycol of the following formula:
wherein A is alkyl, substituted alkyl, cycloalkyl, heteroalkyl, aryl, heteroaryl or substituted aryl; and an amino acid to form an intermediate compound; and
contacting the intermediate compound with a polyaminoalkyl biguanide of the following formula:
wherein n is an integer from 2 to 20;
to form the biocidal compound.

### Claim 4 (depends on 3)

The method of claim 3, wherein the inorganic halide is a halide of phosphorus, bismuth, arsenic or vanadium.

### Claim 5 (depends on 3)

The method of claim 3, wherein the amino acid is serine, threonine or its derivatives.

### Claim 6 (depends on 3)

The method of claim 3, wherein contacting the inorganic halide with the end-capped polyethylene glycol and the amino acid comprises contacting the inorganic halide, the end-capped polyethylene glycol and the amino acid in the presence of a weak base.

### Claim 7 (depends on 3)

The method of claim 3, wherein contacting the intermediate compound with the polyaminoalkyl biguanide comprises contacting the intermediate compound and the polyaminoalkyl biguanide in the presence of an oxidant.

### Claim 8 (depends on 3)

The method of claim 3, wherein contacting the intermediate compound with the polyaminoalkyl biguanide comprises contacting the intermediate compound and the polyaminoalkyl biguanide at a temperature of about 0° C. to about 30° C.

### Claim 9

A method of making a paint polymer, the method comprising:
contacting an inorganic halide with an end-capped quaternary amine polyethylene glycol of the following formula:
wherein A is alkyl, substituted alkyl, cycloalkyl, heteroalkyl, aryl, heteroaryl or substituted aryl;
and an amino acid
to form an intermediate compound; and contacting the intermediate compound with a polyaminoalkyl biguanide of the following formula:
wherein n is an integer from 2 to 20;
to form a biocidal compound;
contacting the biocidal compound with an alkene to form a monomer having the formula I:
wherein E is phosphorus, bismuth, arsenic or vanadium;
R1 is
wherein A is alkyl, substituted alkyl, cycloalkyl, heteroalkyl, aryl, heteroaryl, or substituted aryl;
R2 is —CH2— or —CH(—CH3)—;
R3 is
wherein n is an integer from 2 to 20; and
R4 is vinyl, propenyl, butenyl, pentenyl, or hexenyl;
and incorporating the monomer into a polymer to form a paint.

### Claim 10 (depends on 9)

The method of claim 9, wherein the inorganic halide is a halide of phosphorus, bismuth, arsenic or vanadium.

### Claim 11 (depends on 9)

The method of claim 9, wherein the amino acid is serine, threonine or its derivatives.

### Claim 12 (depends on 9)

The method of claim 9, wherein the alkene is ethylene, propene, butene, pentene or hexene.

### Claim 13 (depends on 9)

The method of claim 9, wherein contacting the inorganic halide with the end-capped polyethylene glycol and the amino acid comprises contacting the inorganic halide, the end-capped polyethylene glycol and the amino acid in the presence of a weak base.

### Claim 14 (depends on 9)

The method of claim 9, wherein contacting the intermediate compound with the polyaminoalkyl biguanide comprises contacting the intermediate compound and the polyaminoalkyl biguanide in the presence of an oxide.

### Claim 15 (depends on 9)

The method of claim 9, wherein contacting the intermediate compound with the polyaminoalkyl biguanide comprises contacting the intermediate compound and the polyaminoalkyl biguanide at a temperature of about 0° C. to about 30° C.

### Claim 16 (depends on 9)

The method of claim 9, wherein incorporating the monomer comprises copolymerizing the monomer with an acrylate to form the polymer.

### Claim 17

A coating composition comprising:
an acrylic polymer comprising a monomeric unit of formula I
wherein E is phosphorus, bismuth, arsenic or vanadium;
R1 is
wherein A is alkyl, substituted alkyl, cycloalkyl, heteroalkyl, aryl, heteroaryl or substituted aryl;
R2 is —CH2— or —CH(—CH3)—;
R3 is
wherein n is an integer from 2 to 20; and
R4 is vinyl, propenyl, butenyl, pentenyl, or hexenyl.

### Claim 18 (depends on 17)

The composition of claim 17, wherein the acrylic polymer is an alkyl methacrylate polymer, an allyl methacrylate polymer, a thioethyl methacrylate polymer, vinyl methacrylate polymer, vinyl benzene polymer, 2-hydroxyethyl acrylate polymer, butyl acrylate polymer, 2-ethylhexyl acrylate polymer or a combination thereof.

### Claim 19 (depends on 17)

The composition of claim 17, wherein the coating is configured to provide a hydrophilic, self-cleaning and biocidal property when applied on a substrate.