EP0949933A1

EP0949933A1 - Use of cyanoacrylate adhesives for providing a protective barrier film for the skin

Info

Publication number: EP0949933A1
Application number: EP96925489A
Authority: EP
Inventors: Patrick J. Tighe; Richard J. Greff; Michael M. Byram; Leonard V. Barkey, Jr.
Original assignee: Medlogic Global Corp
Current assignee: Flowers Park Ltd
Priority date: 1996-07-25
Filing date: 1996-07-25
Publication date: 1999-10-20
Also published as: AU6598696A; EP0949933A4; CA2263460A1

Abstract

A cyanoacrylate adhesive is applied onto skin area prone to exposure to discharge by patients suffering from incontinence so as to shield the skin from direct contact with the discharge. The adhesive can also be applied over medicant that has been applied onto skin surface and onto skin along the periphery of a stoma.

Description

USE OF CYANOACRYLATE ADHESIVES FOR PROVIDING A PROTECTIVE BARRIER FILM FOR

THE SKIN

BACKGROUND OF THE INVENTION

Field of the Invention

This invention is directed to methods of forming a protective barrier layer on skin that is exposed to urine or fecal waste and is particularly suited for individuals suffering from incontinence, by use of a cyanoacrylate adhesive. The cyanoacrylate adhesive to be used can be stored in dispensers for single or repeated/intermittent use and can be applied to the skin by spraying, painting, etc. of die adhesive.

State of the Art

Cyanoacrylate adhesives have been suggested for a variety of adhesive purposes including glues and surgical adhesives. In particular, cyanoacrylate adhesives of formula I: _Q

I i

CH_j-C-COR

I

CN wherein R is an alkyl or o&er suitable substituents are disclosed in U.S. Patent Nos. 3,527,224; 3,591,676; 3,667,472; 3,995,641; 4,035,334; and 4,650,826. Typically, when used as adhesives for living tissues, the R substituent is alkyl of from 2 to 6 carbon atoms and most often is butyl (e.g., n-butyl).

The suggested medical uses for cyanoacrylate adhesives include surgical environments wherein the cyanoacrylate adhesives are utilized, e.g., as an alternative to sutures or as a hemostat. Other suggested uses for these adhesives include their use in inhibiting blister and pressure ulcer formation, as described in U.S. Patent No. 5,306,490, and U.S. Patent Application Serial No. 08/082,927.

This invention is directed to the discovery ±at cyanoacrylates can be used to form in situ a protective barrier layer or coating over skin, including intact skin, to inhibit long term adverse effects of skin exposure to urine and/or fecal matter commonly encountered in patients suffering from incontinence.

In contrast to die mediods of diis invention, Snyder U.S. Patent No. 4,379,863 describes e use of a composition to form a protective barrier film on skin. The composition comprises polymerized materials in me form of acrylate resins that are applied to the skin; die protective barrier firm is formed upon evaporation of the solvent. The protective barrier film so formed, however, has a variety of deficiencies associated with me use of prepolymerized films including weak adherence of the film to the skin and the inability to produce a film having a contour that closely matches the contour of me skin on which me film is applied.

SUMMARY OF THE INVENTION This invention is drawn to methods for preventing infections and/or skin irritation by shielding skin, which can include intact skin, that is prone to exposure to microorganisms and other deleterious agents, with a protective barrier layer that is derived by polymerizing a cyanoacrylate adhesive to form an adhesive polymer coating. The inventive technique prevents die protected skin from the deleterious conditions associated with exposure to moisture and contaminants which otherwise would also be exacerbated by friction on die affected skin caused by contact wim omer skin and/or clothing. Further, me technique prevents skin break down caused by irritating body fluids which include, for example, discharge, perspiration and digestive juices from a stoma. The methods involve applying cyanoacrylate adhesive, particularly n-butyl cyanoacrylate adhesive, onto skin areas to form a flexible, waterproof, gas (e.g., CO₂ and O₂) permeable polymer layer over die skin areas. In turn, diis polymer layer increases skin integrity while reducing the risk of infection by microorganisms. The method is particularly suited for individuals who suffer from incontinence or who require the use of ostomy appliances.

Accordingly, in one of its method aspects, diis invention is directed to a metibod for shielding a patient's skin from discharge caused by incontinence, which memod comprises: applying to a surface skin area prone to exposure to said discharge a sufficient amount of a cyanoacrylate adhesive so as to cover said area; and polymerizing die cyanoacrylate adhesive so as to form a flexible, waterproof, adhesive polymer coating which adheres to die area where me adhesive was applied, wherein the cyanoacrylate, in moπomeric form, is represented by formula I: O

8

CH_j-C-COR _

I ^L

CN where R is selected from the group consisting of: alkyl of 2 to 10 carbon atoms, alkenyl of 2 to 10 carbon atoms, cycloalkyl groups of from 5 to 8 carbon atoms, phenyl,

2-emoxyemyI,

3-medιoxy butyl, and a substituent of die formula:

wherein each R' is independendy selected from die group consisting of: hydrogen and methyl, and R" is selected from die group consisting of: alkyl of from 1 to 6 carbon atoms, alkenyl of from 2 to 6 carbon atoms, alkynyl of from 2 to 6 carbon atoms, cycloalkyl of from 3 to 8 carbon atoms, aralkyl selected from the group consisting of benzyl, methylbenzyl and phenylemyl, phenyl, and phenyl substituted wim 1 to 3 substituents selected from me group consisting of hydroxy, chloro, bromo, nitro, alkyl of 1 to 4 carbon atoms, and alkoxy of from 1 to 4 carbon atoms.

In anodier aspect, me invention is directed to methods of providing a protective covering over a medicament that has been applied onto skin or for skin along me periphery of a stoma which mediods comprise applying me cyanoacrylate adhesive onto me medicament or skin and polymerizing said adhesive.

Preferably R is alkyl of from 2 to 10 carbon atoms and more preferably alkyl of from 2 to 8 carbon atoms. Even more preferably, R is butyl, pentyl or octyl and most preferably, R is n-butyl or iso-butyl.

In a preferred embodiment, me amount of cyanoacrylate applied is at least 0.02 milliliter (ml), and preferably from about 0.02 to about 0.3 ml, of cyanoacrylate adhesive per square centimeter of skin which is to be covered. In anodier preferred embodiment, die cyanoacrylate adhesive to be applied to die skin has a viscosity of from greater than 2 to about 3000 centipoise at 20°C. More preferably, ie cyanoacrylate adhesive is in monomeric form and has a viscosity of from greater dian 2 to about 100 centipoise at 20°C. It is contemplated that pastes and gels having viscosities of up to 50,000 centipoise at 20°C can also be employed.

The term "cyanoacrylate adhesive" refers to adhesive formulations comprising cyanoacrylate monomers of formula I:

where R is selected from the group consisting of alkyl of 2 to 10 carbon atoms, alkenyl of 2 to 10 carbon atoms, cycloalkyl groups of from 5 to 8 carbon atoms, phenyl, 2-emoxyetiιyl, 3-methoxybutyl, and a substituent of the formula:

R' O π.

I I

-C— C— OR"

I

R'

where each R' is independentiy selected from e group consisting of hydrogen and mediyl and R" is selected from the group consisting of alkyl of from 1 to 6 carbon atoms; alkenyl of from 2 to 6 carbon atoms; alkynyl of from 2 to 6 carbon atoms; cycloalkyl of from 3 to 8 carbon atoms; aralkyl selected from die group consisting of benzyl, memylbenzyl and phenylediyl; phenyl; and phenyl substimted wim 1 to 3 substitoents selected from e group consisting of hydroxy, chloro, bromo, nitro, alkyl of 1 to 4 carbon atoms, and alkoxy of from 1 to 4 carbon atoms. Preferably, R is an alkyl group of from 2 to 10 carbon atoms including ediyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, n-pentyl, iso-pentyl, n-hexyl, iso-hexyl, 2-etiryIhexyl, n-heptyl, octyl, nonyl, and decyl. More preferably, R is butyl, pentyl or octyl and most preferably, R is n-butyl or iso-butyl.

These cyanoacrylate adhesives are known in me art and are described in, for example, U.S. Patent Nos. 3,527,224; 3,591,676; 3,667,472; 3,995,641; 4,035,334; and 4,650,826 the disclosures of each are incorporated herein by reference in their entirety.

Preferred cyanoacrylate adhesives for use in die invention are n-butyl-2-cyanoacrylate and iso-butyl-2-cyanoacrylate.

The cyanoacrylate adhesives described herein rapidly polymerize in die presence of water vapor or tissue protein, and me n-butyl-cyanoacrylate is capable of bonding to human skin tissue without causing histoxicity or cytotoxicity.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS This invention relates to cyanoacrylate adhesives which are used to form a protective barrier layer on skin, including more preferably, intact skin. (As used herein, me term "skin" can include eitiier intact skin or broken down skin, or both, wherein die broken down skin is caused, for example, by moisture, friction, maceration, disease, ostomy devices, or combinations tiiereof.) The cyanoacrylate adhesive which is applied to die skin can be monomeric or partially polymeric. In general, partially polymerized cyanoacrylate adhesives are liquid polymers having a higher viscosity tiian tiiat of me corresponding monomer and, merefore, are better suited for those applications which are intended to be specific for a particular skin area. In other words, less viscous materials are more likely to "run" (i.e., flow) into areas where application was not intended.

The cyanoacrylate adhesives used herein preferably have a viscosity of from greater than 2 to about 3000 centipoise and more preferably from greater tiian 2 to about 100 centipoise at 20°C. It is contemplated, however, tihat pastes and gels having viscosities of up to about 50,000 centipoise at 20°C can also be employed and will make for easier skin application. Fumed silica can be used to achieve a viscosity between 1500- 50,000.

The specific viscosity of die formulation depends on die amount and degree of partially polymerized cyanoacrylate adhesive employed as well as additives which are employed in die formulation to enhance or decrease viscosity. Such factors are readily ascertainable by die skilled artisan. For example, methods for preparing partially polymerized cyanoacrylate adhesives are disclosed, for example, by Rabinowitz, U.S. Patent No. 3,527,224 which is incorporated herein by reference in its entirety. Additives which can be incorporated into die formulation enhance its viscosity include polymers such as polymethyl methacrylates (PMMA) and polymerized cyanoacrylates as disclosed in U.S. Patent Nos. 3,654,239 and 4,038,345 bo of which are incorporated herein by reference in their entirety.

Monomeric forms of cyanoacrylate adhesives are often preferred where application is to be made to a large surface area. This preference results from the fact that these forms are less viscous and, accordingly, will permit more facile large surface area application. Mixtures of monomeric forms of cyanoacrylate adhesive and partially polymerized forms of cyanoacrylate adhesive can also be used to prepare a formulation having intermediate viscosities. For purposes of diis invention, monomeric or partially polymerized n-butyl-2-cyanoacrylate or iso-butyl-2-cyanoacrylate is a particularly preferred adhesive and is capable of effectively bonding human skin tissue without causing histoxicity or cytotoxicity.

Upon contact witii skin moisture and tissue protein, me cyanoacrylate adhesives will polymerize or, in the case of partially polymerized cyanoacrylate adhesives, will further polymerize, at ambient conditions (skin temperature) over about 10 to 60 seconds to provide a solid layer which forms over and strongly adheres to me surface of die skin. The resulting adhesive polymer layer or coating is flexible and waterproof diereby forming a protective layer which increases underlying skin integrity and reduces irritation to die surface skin area arising from shearing forces, moisture, friction, etc. In addition, die protective layer is an effective barrier against exposure to microorganisms, acids, caustics and enzymes and o er deleterious materials present in human waste. (These harmful substances are collectively referred to as "human discharge'' or "discharge'' and includes urine and fecal wastes as well as other fluid components which may be incorporated merein, e.g., blood and perspiration.) Thus die protective layer is particularly useful for individuals suffering from incontinence. In addition, for patients who use ostomy appliances, a protective layer can be applied on me skin surrounding die stoma (or otiier artificial passage for bodily elimination). The protective layer also serves to reduce maceration of the skin caused by die ostomy appliances.

It is contemplated tiat d e inventive methods can be used by diemselves or can be employed in conjunction wim existing regimens for inhibiting infections. For instances, in the case of incontinence patients, prior to formation of die protective layer, the intact skin can be cleaned, dried, and a bacteriostat (preferably water based) can be applied to die skin as further means of preventing infection.

The cyanoacrylate adhesive can also be applied as a protective layer over medicament, e.g. cortisone tiiat has been applied to die skin. Preferably, die medicament is water based. The protective layer will adhere to die skin and afford a water resistant barrier film over die medicament. In one embodiment, after die medicament has been applied over a wound, die cyanoacrylate adhesive can be applied over me medicament and at least a portion of die skin surface along die periphery of die wound (or medicament). It is preferable to extend die protective layer on e skin up to about 1 centimeters from the periphery of die medicament and more preferably at least 5 centimeters.

The cyanoacrylate adhesive is applied to provide an effectively tiiick coating over d e human skin tissue prone to be exposed to human discharge in the case of incontinence. Generally, the cyanoacrylate adhesive provides an adhesive coating over die entire skin area prone to exposure which, when set, is waterproof and satisfactorily flexible and adherent to die tissue whhout peeling or cracking. As is apparent, the tinckness of die adhesive coating should be sufficient to afford a barrier against die various microorganisms and chemicals found in d e discharge. In a particularly preferred embodiment, the dύckness of the adhesive coating is from about 0.1 millimeter to about 0.5 millimeter and even more preferably from about 0.1 millimeter to about 0.3 millimeter. Preferably, the adhesive coating has a thickness of less than about 0.5 millimeter (mm), and more preferably the coating has a tiήckness of less tiian about 0.3 mm. It is understood that the adhesive coating, for any application, can be as thick as desired, but within practical limitations that are readily determined by a person skilled in the art. Moreover, witii the present invention successive layers of adhesive coatings can be formed, if desired. The adhesive coating can be formed by applying at least about 0.02 mi of cyanoacrylate adhesive per square centimeter of skin and more preferably from about 0.02 to about 0.2 ml of cyanoacrylate adhesive per square centimeter of skin and even more preferably from about 0.02 to about 0.1 ml of cyanoacrylate adhesive per square centimeter of skin. As is apparent, the amount of cyanoacrylate adhesive applied depends on, among odier things, die concendration of die monomers and/or partially polymerized prepolymers used, and thickness of die protective coating desired. When die concentration is low and/or a tiήck coating is desired, die amount of cyanoacrylate adhesive applied can reach 0.2 ml per square centimeter of skin or higher.

FORMULATIONS The cyanoacrylate adhesive formulations employed herein generally comprise monomeric and/or partially polymerized compounds of formula I described above and are sometimes referred to herein as simply cyanoacrylate adhesives. These formulations are liquid in nature and, upon contact w h surface skin proteins and moisture, will polymerize to provide a solid film or layer over the skin surface.

The formulations may additionally comprise one or more optional additives such as colorants, perfumes, anti-diffusion agents, plasticizers, modifying agents and stabilizers. In practice, each of these optional additives should be both miscible and compatible with die cyanoacrylate adhesive. Compatible additives are tiiose that do not prevent d e use of the cyanoacrylate adhesives for their intended use.

In general, colorants are added so tiiat die polymerized film will contain a discrete and discernable color. Perfumes are added to provide a pleasant smell to the formulation. Stabilizers, such as sulfur dioxide, are added to minimize la situ polymerization in containers during storage. Each of these additives is conventional. For example, suitable stabilizers are disclosed in U.S. Patent No. 4,650,826 die disclosure of which is incorporated herein by reference in its entirety. Plasticizers, such as dioctylphdialate (about 18% - about 25% by weight, preferably about 20%) or tri(p-cresyl)phosphate, can also be added in order to enhance die flexibility of die resulting polymer layer. Suitable plasticizers are disclosed in U.S. Patent Nos. 2,784,127, and 4,444,933 the disclosures of all of tiiese patents are incorporated herein by reference in tiieir entirety.

The amount of each of tiiese optional additives employed in die cyanoacrylate adhesive is an amount necessary to achieve die desired effect.

The formulation is generally stored in an applicator for use in a single dose application or for use in repeated applications. Single dose applicators include those having breakable or removable seals that prevent moisture, including atmospheric moisture, from contacting me formulation and causing in situ polymerization.

For repeated and intermittent usage, minimal exposure to atmospheric moisture is required. This can be achieved by devices having very narrow outlets and low initial deadspace. One applicator for such repeated intermittent use is described in U.S. Patent No. 4,958,748 which is incorporated herein by reference.

Another applicator comprises a conventional spray applicator wherein the cyanoacrylate adhesive is sprayed onto d e surface skin area prone to exposure to human waste. The spray rate of die applicator can be controlled so that application of a metered quantity of adhesive per unit area of skin surface over a set period of time is controlled. Still another applicator comprises a brush or solid paddle applicator wherein die cyanoacrylate adhesive is "painted" onto die surface skin area prone to skin breakdown.

A preferred applicator for repeated and intermittent usage is an applicator suitable for me non-sterile storage and metered dispersement of a cyanoacrylate adhesive after opening of the applicator wherein die applicator is characterized as having a resealable opening of no more than about 0.008 square inches (0.0516 square centimeters) so as to permit die metered dispersement of die adhesive from die applicator and which is capable of multiple administrations of die adhesive and is further characterized as having reseating means such as a cap which e her tightiy mates with the applicator or which screws onto die applicator.

Preferably, me opening of the applicator is about 0.0016 to about 0.003 square inches (about 0.0103 to about 0.0194 square centimeters).

In another preferred embodiment, the walls of the applicator are made of a pliable material, so that upon application of pressure onto die walls, the walls depress sufficientiy to force die adhesive contained in the applicator dirough die opening. Preferably, the applicator is manufactured wim its opening covered by a metal foil or other similar construction which closes diis opening until die device is ready for use. The opening is then reinstated by use of a pin or similar device which punctures e covering.

In applicators suitable for repeated intermittent uses, the cyanoacrylate adhesive is stored at ambient conditions and is selected to be bacteriostatic. See, for example, Rabinowitz et al., U.S. Patent No. 3,527,224. When the selected adhesive is bacteriostatic, prolonged storage at ambient conditions can be achieved widiout regard to me sterility of the formulation. METHODOLOGY With respect to individuals suffering from incontinence, die methods of diis invention provide for die in situ formation of a polymeric layer of cyanoacrylate adhesive over skin areas likely to be exposed to human discharge and, accordingly, are prone to skin breakage which can further lead to infection. The methods of diis invention involve application of die above-described formulations to surface skin areas, that are prone to be exposed to human discharge, under conditions suitable for polymerizing die adhesive so as to form a protective coating. In general, sufficient amounts of cyanoacrylate adhesive are employed to cover (i.e., coat) die entire area that is prone to exposure, such as around the buttocks and thighs. The coating is preferably extended by at least about 1 centimeter and preferably by at least about 5 centimeters beyond die area expected to be exposed. (A similar strategy is employed for patients using ostomy appliances. Specifically, the adhesive coating is formed on skin around die periphery of an artificial passage (e.g., stoma) where the ostomy appliance is positioned.)

The adhesive polymer coating should be maintained in a unbroken manner over the entire area prone to exposure. This can be assured by careful application of die adhesive onto die skin. However, in a preferred embodiment, after the initial layer of adhesive has cured to provide for an adhesive polymer coating, a second, preferably thinner, layer is applied over die adhesive polymer coating. Additional amounts of cyanoacrylate adhesive can be applied as needed to maintain an unbroken protective covering over die surface skin areas.

Sufficient cyanoacrylate adhesive is preferably employed to form a coating of less than about 0.5 mm thick and more preferably at least about 0.1 mm thick. Such coatings can be formed by applying at least about 0.02 ml of cyanoacrylate adhesive per square centimeter of skin surface area.

The amount of cyanoacrylate adhesive applied onto die skin surface area can be controlled by die amount of adhesive packaged in a single dose product or by use of a multiple use dispenser which governs die amount of material applied onto a unit area of surface skin. In diis regard, the dispenser described by Otake, U.S. Patent No. 4,958,748, which is incorporated by reference in its entirety, is particularly advantageous because it dispenses die adhesive in a controlled dropwise manner. O er methods for die controlled dispersement of die cyanoacrylate adhesive are as described above including, by way of example, a conventional spray applicator, a brush or solid paddle applicator, and die like.

Upon application of die cyanoacrylate adhesive, the surface skin moisture, tissue protein, and temperature are sufficient to initiate polymerization of die adhesive upon application. Thereafter, die skin surface is maintained under suitable conditions to allow polymerization to proceed to formation of an adhesive coating.

In general, the particular length of time required for polymerization will vary depending on factors such as die amount of adhesive applied, me temperature of d e skin, the moisture content of the skin, the surface area of skin, and die like. However, in a preferred embodiment, polymerization is generally complete within about 10 to about 60 seconds while die skin is maintained at ambient conditions. During dis period, the person to whom application of me cyanoacrylate adhesive has been made merely allows the adhesive to form a coating while minimizing any action to prevent die adhesive from being dislodged from that portion of die skin where it was applied or to adhere to unintended objects. Excess adhesive polymer can be removed with acetone (nail polish remover) which can be readily conducted except in d e case where die adhesive polymer binds to a sensitive skin part (e.g., die eye lids) where it should be removed by a health care professional.

After the adhesive coating has formed, the coating strongly adheres to e skin, is flexible and waterproof, tiiereby forming a protective coating which enhances die integrity of die underlying skin and protects die skin from exposure to human waste. Accordingly, the coating inhibits skin breakdown in the incontinent patient because the intact skin no longer is exposed to d e human waste and because skin breakage is inhibited, subsequent infection of the broken skin is also inhibited. Furthermore, the protective coating also significantiy reduces die amount of frictional stress the skin is subject to.

In general, die coating will adhere to the skin for a period of more than 24 hours and preferably for about at least 2-4 days after which time it sloughs off. Additional applications can be made if desired.

Because die cyanoacrylate adhesive polymer coating is waterproof and will not wash off, die patient is not prevented from bathing and omer activities involving exposure to water during die period the adhesive layer protects diis skin area.

The following examples illustrate certain embodiments of die invention but is not meant to limit the scope of the claims in any way. EXAMPLES fixqmpfe 1 A cyanoacrylate adhesive formulation is prepared in monomeric form using n-butyl α-cyanoacrylate about 20% by weight dioctylphthlate and about 200 ppm SO₂. The formulation also contains a blue colorant to readily ascertain where it has been applied. The formulation is applied onto die buttocks/coccyx area in an amount of 0.1 milliliter per square centimeter of treated skin using a gloved finger and, after application, die skin is maintained at ambient condition until a polymer coating forms in about 30 to 120 seconds.

After die application of die cyanoacrylate adhesive layer on die skin has formed die polymer coating will protect me skin from feces and urine, while allowing die patient to wear a diaper-like garment commonly worn by patients with incontinence.

Example 2

The same formulation as described in Example 1 is applied under female breasts, and allowed to form a polymer coating. The flexible, waterproof coating prevents sweat sores from developing.

Example 3 The same formulation of Example 1 can be applied to die skin surface around die stoma (i.e. to the small intestines) to help protect the skin area from irritation by digestive juices, urine, or adhesives from the stoma bag (which is usually made of plastic).

From the foregoing description, various modifications and changes in the composition and method will occur to those skilled in the art. All such modifications coming within die scope of die appended claims are intended to be included therein.

Claims

WHAT IS CLAIMED IS:

1. A method for shielding a patient's skin from urine or fecal wastes caused by incontinence, which method comprises: applying to a surface skin area which comes in contact witii such urine or fecal wastes a sufficient amount of a cyanoacrylate adhesive to cover said area from said urine and/or fecal wastes; and polymerizing die cyanoacrylate adhesive so as to form a flexible, waterproof, adhesive polymer coating which adheres to die area where die adhesive was applied, wherein the cyanoacrylate, in monomeric form, is represented by formula I: O

where R is selected from the group consisting of: alkyl of 2 to 10 carbon atoms, alkenyl of 2 to 10 carbon atoms, cycloalkyl groups of from 5 to 8 carbon atoms, phenyl,

2-ethoxy ethyl, 3-medιoxybutyl, and a substituent of die formula:

wherein each R' is independently selected from the group consisting of: hydrogen and methyl, and R" is selected from the group consisting of: alkyl of from 1 to 6 carbon atoms, alkenyl of from 2 to 6 carbon atoms, alkynyl of from 2 to 6 carbon atoms, cycloalkyl of from 3 to 8 carbon atoms, aralkyl selected from me group consisting of benzyl, methylbenzyl and phenylediyl, phenyl, and phenyl substimted with 1 to 3 substituents selected from the group consisting of hydroxy, chloro, bromo, nitro, alkyl of 1 to 4 carbon atoms, and alkoxy of from 1 to 4 carbon atoms.

2. A method according to Claim 1 wherein R is alkyl of from 2 to 8 carbon atoms.

3. A method according to Claim 2 wherein R is butyl, pentyl or octyl.

4. A method according to Claim 3 wherein R is n-butyl or iso- butyl.

5. A method according to Claim 1 wherein said adhesive is applied in an amount of at least 0.02 ml of cyanoacrylate adhesive per square centimeter of skin which is to be covered.

6. A method according to Claim 5 wherein the cyanoacrylate adhesive is applied in an amount of from about 0.02 ml to about 0.2 ml per square centimeter of skin.

7. A method according to Claim 6 wherein the cyanoacrylate adhesive is applied in an amount of from about 0.02 ml to about 0.1 ml per square centimeter of skin.

8. A method according to Claim 1 wherein the cyanoacrylate adhesive has a viscosity of from greater than 2 to about 3000 centipoise at 20°C.

9. A method according to Claim 8 wherein me cyanoacrylate adhesive has a viscosity of from greater than 2 to about 1 0 centipoise at 20°C.

10. A method according to Claim 1 wherein the cyanoacrylate adhesive is applied from a single use applicator.

11. A method according to Claim 1 wherein, prior to applying the cyanoacrylate adhesive onto the surface skin area, the method comprises of applying a bacteriostat onto me surface skin area.

12. A method for providing a protective covering over a medicant on a patient, which method comprises: applying a medicament onto the skin; applying onto said medicament and onto surface skin along the periphery of said medicament, a sufficient amount of a cyanoacrylate adhesive so as to cover said medicament and surface skin; and polymerizing the cyanoacrylate adhesive so as to form a flexible, waterproof, adhesive polymer coating which adheres to the surface skin where the adhesive was applied, wherein the cyanoacrylate, in monomeric form, is represented by formula I:

O

I i.

CH_j-C-COR

!

CN where R is selected from the group consisting of: alkyl of 2 to 10 carbon atoms, alkenyl of 2 to 10 carbon atoms, cycloalkyl groups of from 5 to 8 carbon atoms, phenyl, 2-ethoxyethyl, 3-medιoxybutyl, and a substituent of d e formula:

wherein each R' is mdependendy selected from die group consisting of: hydrogen and methyl, and R" is selected from the group consisting of: alkyl of from 1 to 6 carbon atoms, alkenyl of from 2 to 6 carbon atoms, alkynyl of from 2 to 6 carbon atoms, cycloalkyl of from 3 to 8 carbon atoms, aralkyl selected from the group consisting of benzyl, methylbenzyl and phenylediyl, phenyl, and phenyl substimted witii 1 to 3 substiments selected from the group consisting of hydroxy, chloro, bromo, nitro, alkyl of 1 to 4 carbon atoms, and alkoxy of from 1 to 4 carbon atoms.

13. A method according to Claim 12 wherein R is alkyl of from 2 to 8 carbon atoms.

14. A method according to Claim 13 wherein R is butyl, pentyl or octyl.

15. A method according to Claim 14 wherein R is n-butyl or iso- butyl.

16. A method for providing a protective covering on skin along me periphery of a patient's stoma which method comprises: applying onto said skin along die periphery of die stoma a sufficient amount of a cyanoacrylate adhesive so as to cover said skin; and polymerizing the cyanoacrylate adhesive so as to form a flexible, waterproof, adhesive polymer coating which adheres to me skin surface where the adhesive was applied, wherein die cyanoacrylate, in monomeric form, is represented by formula I:

2-edιoxyedιyl,

3-methoxybutyl, and a substituent of the formula: wherein each R' is mdependendy selected from the group consisting of: hydrogen and methyl, and R" is selected from the group consisting of: alkyl of from 1 to 6 carbon atoms, alkenyl of from 2 to 6 carbon atoms, alkynyl of from 2 to 6 carbon atoms, cycloalkyl of from 3 to 8 carbon atoms, aralkyl selected from the group consisting of benzyl, methylbenzyl and phenylediyl, phenyl, and phenyl substituted with 1 to 3 substiments selected from die group consisting of hydroxy, chloro, bromo, nitro, alkyl of 1 to 4 carbon atoms, and alkoxy of from 1 to

4 carbon atoms.

17. A method according to Claim 16 wherein R is alkyl of from 2 to 8 carbon atoms.

18. A mediod according to Claim 17 wherein R is butyl, pentyl or octyl.

19. A mediod according to Claim 18 wherein R is n-butyl or iso- butyl.