# US 2016/0135463 A9 · Selenium-based biocidal formulations and methods of use thereof

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- Number: US 2016/0135463 A9
- Document ID: US20160135463A9
- Status: Published application
- Kind: A9
- Application number: 13/762,147
- Filed: 2013-02-07
- Published: 2016-05-19
- Earliest claimed: 2009-02-03
- Assignees: Selenium, Ltd.
- Applicants: Selenium, Ltd.
- Inventors: Ted W. Reid; Julian Spallholz; Robert Eugene Hanes
- Web page: https://patentgrep.com/patent/US20160135463A9

## CPC

- A01N 55/00: Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur (containing organo-phosphorus compounds A01N57/00)
- A01N 25/10: Macromolecular compounds
- A61K 9/0014: {Skin, i.e. galenical aspects of topical compositions (non-active ingredients are additionally classified in A61K47/00; A61K9/0009, A61K9/0021, A61K9/7015, A61K9/7023 take precedence; cosmetic preparations A61K8/00, A61Q; preparations for wound dressings or bandages A61L26/00)}
- A61K 9/0051: {Ocular inserts or implants}
- A61K 31/095: Sulfur, selenium, or tellurium compounds, e.g. thiols
- A61K 31/26: Cyanate or isocyanate esters; Thiocyanate or isothiocyanate esters
- A61K 31/655: Azo (—N=N—), diazo (=N2), azoxy (>N—O—N< or N(=O)—N<), azido (—N3) or diazoamino (—N=N—N<) compounds
- A61K 33/04: Sulfur, selenium or tellurium; Compounds thereof
- A61L 15/46: Deodorants or malodour counteractants, e.g. to inhibit the formation of ammonia or bacteria
- A61L 29/16: Biologically active materials, e.g. therapeutic substances {(A61L29/048 takes precedence)}
- A61L 2300/102: Metals or metal compounds, e.g. salts such as bicarbonates, carbonates, oxides, zeolites, silicates
- A61L 2300/404: Biocides, antimicrobial agents, antiseptic agents
- 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
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61L: METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES (preservation of bodies or disinfecting characterised by the agents employed A01N; preserving, e.g. sterilising, food or foodstuffs A23; preparations for medical, dental or toiletry purposes A61K)

## Abstract

Biocidal compositions containing organoselenium compounds are disclosed, as well as methods of producing and using same.

## Claims

### Claim 1

A composition, comprising:
a substrate having a surface; and
a biocidal composition disposed on the surface of the substrate and/or impregnated throughout the substrate, the biocidal composition having the formula:
wherein the grafting agent is a first functional group that attaches the biocidal composition to the substrate, and wherein the grafting agent is selected from the group consisting of vinyl, acrylate, methacrylate, acrylamide, vinyl, alcohol, amine, carboxylic acid, ester, amide, ether, acid chloride, N-hydroxysuccinimide activated esters, and combinations thereof;
wherein the linker group is a second functional group that modulates solubility of the biocidal composition, wherein the linker group contains 2-20 carbons and is selected from the group consisting of linear aliphatic chains, branched aliphatic chains, ring structures, and combinations thereof; and
wherein the properties group is a third functional group that modulates physical properties of the biocidal composition, the properties group selected from the group consisting of alcohols, amines, carboxylic acids, and combinations thereof.

### Claim 2 (depends on 1)

The composition of claim 1, wherein the biocidal composition is permanently attached to the substrate, whereby the biocidal composition is substantially unable to leach from the substrate.

### Claim 3 (depends on 1)

The composition of claim 1, wherein the biocidal composition is effective against at least one of a gram positive bacterial strain, a gram negative strain, a virus, a fungus, an algae, and a mold.

### Claim 4 (depends on 2)

The composition of claim 2, wherein the biocidal composition is effective against at least one gram positive bacterial strain and at least one gram negative strain, wherein the gram positive strain is Staphylococcus aureus and the gram negative strain is Pseudomonas aeruginosa.

### Claim 5 (depends on 1)

The composition of claim 1, wherein the biocidal composition is effective against at least one gram positive bacterial strain, at least one gram negative strain, at least one virus, at least one fungus, at least one algae, and at least one mold.

### Claim 6 (depends on 2)

The composition of claim 2, wherein the biocidal composition inhibits formation of bacterial biofilms on the substrate.

### Claim 7 (depends on 1)

The composition of claim 1, wherein the selenium compound of the biocidal composition is present in a range of from about 0.01 micrograms to about 100 micrograms of elemental selenium per square centimeter of surface area.

### Claim 8 (depends on 1)

The composition of claim 1, wherein the grafting agent is a methacrylate compound.

### Claim 9 (depends on 8)

The composition of claim 8, wherein the biocidal composition is diselanediylbis(2-hydroxypropane-3,1-diyl)bis(2-methylacrylate).

### Claim 10 (depends on 1)

The composition of claim 1, wherein the biocidal composition is 3,3′-diselanediylbis(propane-1,2-diol).

### Claim 11 (depends on 1)

The composition of claim 1, wherein the grafting agent is an acrylate polymer, and wherein the biocidal composition is non-covalently associated with the substrate.

### Claim 12 (depends on 1)

The composition of claim 1, wherein the selenium anion Se— and free radical species are generated when the biocidal composition comes into contact with a surface of a living cell and/or living organism, whereby the selenium anion Se— remains permanently attached to the substrate and the free radical species inhibits and/or inactivates said living cell and/or living organism, thereby inhibiting growth of the living cell and/or living organism on the substrate.

### Claim 13 (depends on 1)

The composition of claim 1, wherein the substrate is a solid substrate formed of a thermoplastic polymer, and wherein the grafting agent of the biocidal composition covalently attaches to the thermoplastic polymer when the polymer is in a molten form.

### Claim 14 (depends on 1)

The composition of claim 1, wherein the substrate is a semi-permeable substrate, and wherein the grafting agent of the biocidal composition forms a covalent network within the semi-permeable substrate.

### Claim 15 (depends on 14)

The composition of claim 14, wherein the covalent network formed by the grafting agent of the biocidal composition is substantially not attached to the semi-permeable substrate by a covalent bond, and wherein branches of the covalent network are interdigitated.

### Claim 16 (depends on 14)

The composition of claim 14, wherein the grafting agent of the biocidal composition covalently attaches to the semi-permeable substrate.

### Claim 17 (depends on 1)

The composition of claim 1, wherein the substrate is a liquid substrate.

### Claim 18 (depends on 1)

The composition of claim 1, wherein the substrate is selected from the group consisting of catheters, bandages, adhesive tapes, fabrics, fibers, plastics, cellulose pads, protein pads, carbohydrate pads, contact lenses, diapers, membranes, membrane spacers, implants, tubing, beverage tubing, medical tubing, paints, coatings, and combinations thereof.

### Claim 19

A thermoplastic polymer masterbatch composition, comprising:
a grafted biocidal composition uniformly dispersed in at least one thermoplastic polymer, the amount of the grafted biocidal composition ranging from about 1% to about 20% by weight, the grafted biocidal composition having the formula:
wherein the grafting agent is a first functional group that attaches the biocidal composition to the substrate, and wherein the grafting agent is selected from the group consisting of vinyl, acrylate, methacrylate, acrylamide, vinyl, alcohol, amine, carboxylic acid, ester, amide, ether, acid chloride, N-hydroxysuccinimide activated esters, and combinations thereof;
wherein the linker group is a second functional group that modulates solubility of the biocidal composition, wherein the linker group contains 2-20 carbons and is selected from the group consisting of linear aliphatic chains, branched aliphatic chains, ring structures, and combinations thereof; and
wherein the properties group is a third functional group that modulates physical properties of the biocidal composition, the properties group selected from the group consisting of alcohols, amines, carboxylic acids, and combinations thereof.

### Claim at position 20

-21. (canceled)