# US 8,784,793 B2 · Conformable solvent-based bandage and coating material

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- Number: US 8,784,793 B2
- Document ID: US8784793B2
- Status: Granted
- Kind: B2
- Application number: 13/947,844
- Filed: 2013-07-22
- Published: 2013-11-14
- Granted: 2014-07-22
- Earliest claimed: 2005-08-17
- Assignees: Rochal Industries, LLP
- Applicants: Rochal Industries LLP
- Inventors: Ann Beal Salamone; Joseph C. Salamone
- Web page: https://patentgrep.com/patent/US8784793B2

## CPC

- A61L 26/0019: {obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds}
- A61K 31/785: Polymers containing nitrogen
- A61L 24/0021: {Plasticisers}
- A61L 24/043: {Mixtures of macromolecular materials}
- A61L 24/06: obtained by reactions only involving carbon-to-carbon unsaturated bonds {(A61L24/043, A61L24/046 take precedence)}
- A61P 7/04: Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
- 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)
- 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)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

A biological coating material that includes a polymerizable polyacrylate monomer; a volatile liquid; a polymer selected from a synthetic rubber, a natural rubber, and a thermoplastic elastomer. The biological liquid coating material forms a coating or bandage in the form of a film that when applied and adhered to a surface or to the skin of a user inhibits the application surface from adhering to another surface.

## Claims

### Claim 1

A biological coating composition comprising:
a polymerizable cyanoacrylate monomer present in an amount of about 0.5 wt % to 40 wt %;
a volatile liquid having a solubility parameter of 4.9-12.5 (cal/cm3)1/2; and
a siloxysilane-containing polymer comprising an addition polymerizable monomer selected from the group consisting of acrylates, methacrylates, fluorinated siloxanes, fluorinated itaconates, fluorinated methacrylates, fluorinated acrylates and combinations thereof;
wherein the coating composition forms an adherent, conformable polymer coating when applied to a biological surface; and
wherein the volatile liquid volatilizes at room or body temperature.

### Claim 2 (depends on 1)

The biological coating composition of claim 1, wherein the biological surface is a surgical site, skin, or mucous membrane.

### Claim 3 (depends on 2)

The biological coating composition of claim 2, wherein the coating composition forms an adherent, conformable polymer coating when applied to hydrated skin.

### Claim 4 (depends on 1)

The biological coating composition of claim 1, further comprising a second polymer selected from the group consisting of a synthetic rubber, a natural rubber, and a thermoplastic elastomer.

### Claim 5 (depends on 4)

The biological coating composition of claim 4, wherein the second polymer comprises a rubber selected from the group consisting of a diene, styrene, acrylonitrile, and mixture thereof.

### Claim 6 (depends on 1)

The biological coating composition of claim 1, wherein the polymerizable cyanoacrylate monomer is present in an amount of about 0.5 wt % to 32 wt %.

### Claim 7 (depends on 6)

The biological coating composition of claim 6, wherein the volatile liquid is present in an amount of about 10 wt % to about 99.9 wt %.

### Claim 8 (depends on 1)

The biological coating composition of claim 1, wherein the volatile liquid is selected from the group consisting of volatile linear and cyclic siloxanes, volatile polydimethylsiloxanes, isooctane, octane, and combinations thereof.

### Claim 9 (depends on 8)

The biological coating composition of claim 8, wherein the volatile liquid comprises a liquid selected from the group consisting of hexamethyldisiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, octamethyltrisiloxanes, and combinations thereof.

### Claim 10 (depends on 1)

The biological coating composition of claim 1, wherein the polymerizable cyanoacrylate monomer component comprises an alpha-cyanoacrylate monomer.

### Claim 11 (depends on 10)

The biological coating composition of claim 10, wherein the alpha-cyanoacrylate monomer comprises at least one of n-butyl cyanoacrylate and 2-octyl cyanoacrylate.

### Claim 12 (depends on 1)

The biological coating composition of claim 1, wherein the siloxysilane-containing polymer further comprises a siloxysilane monomer selected from the group consisting of:
3-methacryloyloxypropyltris(trimethylsiloxy)silane,
3-methacryloyloxypropylpentamethyldisiloxane,
3-methaciyloyloxypropylbis(trimethylsiloxy)methylsilane,
3-methacryloyloxypropyltris(vinyldimethylsiloxy)silane,
3-methacryloyloxymethylbis(trimethylsiloxy)(pentamethyldisiloxanyl)silane-,
3-methacryloyloxyethyltris(pentamethyldisiloxanyl)silane,
methacryloyloxymethylbis(trimethylsiloxy)methylsilane,
methacryloyloxymethyltris(trimethylsiloxy)silane,
3-methacryloyloxypropylheptacyclopentyl-T8-silsesquioxane,
3-methacryloyloxypropylheptaisobutyl-T8-silsesquioxane,
3-acryloyloxypropylmethylbis(trimethylsiloxy)silane,
3-acryloyloxypropyltris(trimethylsiloxy)silane,
3-methacryloyloxypropyl-1,1,1-triphenyl-3,3-dimethyldisiloxane,
3-methacrylamidopropyltris(trimethylsiloxy)silane,
3-acrylamidopropyltris(trimethylsiloxy)silane,
p-vinylphenyltris(trimethylsiloxy)silane,
p-vinylbenzyltris(trimethylsiloxy)silane,
vinyloxyethyltris(trimethylsiloxy)silane,
vinylnonyldimethyl(trimethylsiloxy)silane,
vinylnonyltris(trimethylsiloxy)silane,
vinylmethylbis(trimethylsiloxy)silane,
vinylpentamethyldisiloxane,
O-(vinyloxyethyl)-N-(tris[trimethylsiloxy]silylpropyl)urethane,
vinylphenylbis(trimethylsiloxy)silane,
vinyltris(dimethylsiloxy)silane,
vinyltris(trimethylsiloxy)silane,
vinyl-terminated polydimethylsiloxane,
polydimethylsiloxane monoacrylate,
polydimethylsiloxane monomethacrylate,
polymethylphenylsiloxane monoacrylate,
polymethylphenylsiloxane monomethacrylate,
3-acryloyloxypropyltris(polydimethylsiloxanyl)silane, and
combinations thereof.

### Claim 13 (depends on 1)

The biological coating composition of claim 1, wherein the siloxysilane-containing polymer is present in an amount ranging from about 0.01 wt-% to about 99.5 wt-%.

### Claim 14

A biological coating composition comprising:
a polymerizable cyanoacrylate monomer present in an amount of about 0.5 wt % to 40 wt %;
a volatile liquid having a solubility parameter of 4.9-12.5 (cal/cm3)1/2; and
a polymer selected from the group consisting of polycyanoacrylate, polycaprolactone, polyorthoester, polyalkyl acrylate, copolymers of alkyl acrylate and vinyl acetate, polyalkyl methacrylates, copolymers of alkyl methacrylates and butadiene, copolymers of acrylate and methacrylate monomers, and combinations thereof;
wherein the coating composition forms an adherent, conformable polymer coating when applied to a biological surface; and
wherein the volatile liquid volatilizes at room or body temperature.

### Claim 15 (depends on 14)

The biological coating composition of claim 14, wherein the biological surface is a surgical site, skin, or mucous membrane.

### Claim 16 (depends on 15)

The biological coating composition of claim 15, wherein the coating composition forms an adherent, conformable polymer coating when applied to hydrated skin.

### Claim 17 (depends on 14)

The biological coating composition of claim 14, further comprising a second polymer selected from the group consisting of a synthetic rubber, a natural rubber, and a thermoplastic elastomer.

### Claim 18 (depends on 17)

The biological coating composition of claim 17, wherein the second polymer comprises a rubber selected from the group consisting of a diene, styrene, acrylonitrile, and mixture thereof.

### Claim 19 (depends on 14)

The biological coating composition of claim 14, wherein the polymerizable cyanoacrylate monomer is present in an amount of about 0.5 wt % to 32 wt %.

### Claim 20 (depends on 19)

The biological coating composition of claim 19, wherein the volatile liquid is present in an amount of about 10 wt % to about 99.9 wt %.

### Claim 21 (depends on 14)

The biological coating composition of claim 14, wherein the volatile liquid is selected from the group consisting of volatile linear and cyclic siloxanes, volatile polydimethylsiloxanes, isooctane, octane, and combinations thereof.

### Claim 22 (depends on 21)

The biological coating composition of claim 21, wherein the volatile liquid comprises a liquid selected from the group consisting of hexamethyldisiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, octamethyltrisiloxanes, and combinations thereof.

### Claim 23 (depends on 14)

The biological coating composition of claim 14, wherein the polymerizable cyanoacrylate monomer component comprises an alpha-cyanoacrylate monomer.

### Claim 24 (depends on 23)

The biological coating composition of claim 23, wherein the alpha-cyanoacrylate monomer comprises at least one of n-butyl cyanoacrylate and 2-octyl cyanoacrylate.

### Claim 25 (depends on 14)

The biological coating composition of claim 14, further comprising a siloxysilane-containing polymer.

### Claim 26 (depends on 25)

The biological coating composition of claim 25, wherein the siloxysilane-containing polymer comprises a monomer selected from the group consisting of:
3-methacryloyloxypropyltris(trimethylsiloxy)silane,
3-methacryloyloxypropylpentamethyldisiloxane,
3-methacryloyloxypropylbis(trimethylsiloxy)methylsilane,
3-methacryloyloxypropyltris(vinyldimethylsiloxy)silane,
3-methacryloyloxymethylbis(trimethylsiloxy)(pentamethyldisiloxanyl)silane-,
3-methacryloyloxyethyltris(pentamethyldisiloxanyl)silane,
methacryloyloxymethylbis(trimethylsiloxy)methylsilane,
methacryloyloxymethyltris(trimethylsiloxy)silane,
3-methacryloyloxypropylheptacyclopentyl-T8-silsesquioxane,
3-methacryloyloxypropylheptaisobutyl-T8-silsesquioxane,
3-acryloyloxypropylmethylbis(trimethylsiloxy)silane,
3-acryloyloxypropyltris(trimethylsiloxy)silane,
3-methacryloyloxypropyl-1,1,1-triphenyl-3,3-dimethyldisiloxane,
3-methacrylamidopropyltris(trimethylsiloxy)silane,
3-acrylamidopropyltris(trimethylsiloxy)silane,
p-vinylphenyltris(trimethylsiloxy)silane,
p-vinylbenzyltris(trimethylsiloxy)silane,
vinyloxyethyltris(trimethylsiloxy)silane,
vinylnonyldimethyl(trimethylsiloxy)silane,
vinylnonyltris(trimethylsiloxy)silane,
vinylmethylbis(trimethylsiloxy)silane,
vinylpentamethyldisiloxane,
O-(vinyloxyethyl)-N-(tris[trimethylsiloxy]silylpropyl)urethane,
vinylphenylbis(trimethylsiloxy)silane,
vinyltris(dimethylsiloxy)silane,
vinyltris(trimethylsiloxy)silane,
vinyl-terminated polydimethylsiloxane,
polydimethylsiloxane monoacrylate,
polydimethylsiloxane monomethacrylate,
polymethylphenylsiloxane monoacrylate,
polymethylphenylsiloxane monomethacrylate,
3-acryloyloxypropyltris(polydimethylsiloxanyl)silane, and
combinations thereof.

### Claim 27 (depends on 25)

The biological coating composition of claim 25, wherein the siloxysilane-containing polymer is present in an amount ranging from about 0.01 wt-% to about 99.5 wt-%.
