WO1993020829A1 - Methods for retarding blister formation by use of cyanoacrylate adhesives - Google Patents
Methods for retarding blister formation by use of cyanoacrylate adhesives Download PDFInfo
- Publication number
- WO1993020829A1 WO1993020829A1 PCT/US1993/003716 US9303716W WO9320829A1 WO 1993020829 A1 WO1993020829 A1 WO 1993020829A1 US 9303716 W US9303716 W US 9303716W WO 9320829 A1 WO9320829 A1 WO 9320829A1
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- WO
- WIPO (PCT)
- Prior art keywords
- cyanoacrylate adhesive
- adhesive
- carbon atoms
- cyanoacrylate
- skin
- Prior art date
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- 239000004830 Super Glue Substances 0.000 title claims abstract description 68
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 40
- 238000000034 method Methods 0.000 title claims description 32
- 230000000979 retarding effect Effects 0.000 title description 7
- FGBJXOREULPLGL-UHFFFAOYSA-N ethyl cyanoacrylate Chemical compound CCOC(=O)C(=C)C#N FGBJXOREULPLGL-UHFFFAOYSA-N 0.000 claims abstract description 51
- 230000037081 physical activity Effects 0.000 claims abstract description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 32
- 206010020649 Hyperkeratosis Diseases 0.000 claims description 31
- 239000000853 adhesive Substances 0.000 claims description 23
- 230000001070 adhesive effect Effects 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 8
- -1 2-ethoxyethyl Chemical group 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 230000002401 inhibitory effect Effects 0.000 claims description 6
- 229920001651 Cyanoacrylate Polymers 0.000 claims description 5
- MWCLLHOVUTZFKS-UHFFFAOYSA-N Methyl cyanoacrylate Chemical compound COC(=O)C(=C)C#N MWCLLHOVUTZFKS-UHFFFAOYSA-N 0.000 claims description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000006178 methyl benzyl group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 210000003491 skin Anatomy 0.000 description 39
- 239000000203 mixture Substances 0.000 description 16
- 238000009472 formulation Methods 0.000 description 13
- 238000006116 polymerization reaction Methods 0.000 description 7
- 239000000654 additive Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 3
- 210000004872 soft tissue Anatomy 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 210000002615 epidermis Anatomy 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 230000007794 irritation Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
- 201000006082 Chickenpox Diseases 0.000 description 1
- 206010046980 Varicella Diseases 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229950010048 enbucrilate Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 230000036512 infertility Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000003894 surgical glue Substances 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/74—Synthetic polymeric materials
- A61K31/765—Polymers containing oxygen
- A61K31/78—Polymers containing oxygen of acrylic acid or derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61B—DIAGNOSIS; SURGERY; IDENTIFICATION
- A61B17/00—Surgical instruments, devices or methods, e.g. tourniquets
- A61B17/00491—Surgical glue applicators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
- A61L24/04—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials
- A61L24/06—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S526/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S526/936—Physiological use, e.g. pharmaceutical, veterinary, dental
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S602/00—Surgery: splint, brace, or bandage
- Y10S602/904—Film-forming bandage material
Definitions
- the present invention is directed to methods for retarding blister formation by use of cyanoacrylate adhesives that can be applied to skin areas prone to blistering prior to blister formation.
- Cyanoacrylate adhesives have been suggested for a variety of adhesive purposes including glues and surgical adhesives.
- R is an alkyl or other 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.
- the R substituent is alkyl of from 2 to 6 carbon atoms and most often is butyl.
- cyanoacrylate adhesives have been limited to surgical environments wherein the cyanoacrylate adhesives are utilized as an alternative to sutures and are employed in a sterile environment. Specifically, in surgical environments, the cyanoacrylate adhesive is applied to separate sections of soft tissue.
- the cyanoacrylate adhesive in the presence of water found in soft tissue, bonds to the skin as well as polymerizes so as to join separate sections of soft tissue together.
- the present invention is a result of the discovery that application of cyanoacrylate adhesives to blister prone areas and subsequent polymerization results in the formation of an artificial callus over the blister prone area thereby retarding the formation of blisters in these areas. More particularly, the application of cyanoacrylate adhesives is only to the surface of the skin and not to cut areas of skin.
- the present invention is directed to methods for inhibiting blister formation by application of a cyanoacrylate adhesive to the skin area prone to blistering prior to blister formation.
- the present invention is directed to a method for inhibiting blister formation arising from friction during physical activities which method comprises: applying, either prior to or during physical activities but prior to blister formation, a quantity of cyanoacrylate adhesive to a surface area of uncut skin which is prone to blister formation, which quantity of cyanoacrylate adhesive is sufficient to form an artificial callus; and maintaining the cyanoacrylate adhesive under conditions which polymerize the adhesive thereby forming an artificial callus which adheres to the surface area of uncut skin where the adhesive was applied.
- the cyanoacrylate, in monomeric form is represented by formula I:
- R is selected from the group consisting of alkyl of 1 to 10 carbon atoms, alkenyl of 2 to 10 carbon atoms, cycloalkyl groups of from 5 to 8 carbon atoms, phenyl, 2-ethoxyethyl, 3-methoxybutyl, and a substituent of the formula:
- 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 the group consisting of benzyl, methylbenzyl and phenylethyl; phenyl; and phenyl substituted 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.
- R is alkyl of from 1 to 10 carbon atoms and more preferably alkyl of from 2 to 6 carbon atoms. Most preferably, R is n-butyl.
- the present invention is directed to a method for inhibiting blister formation arising from friction during physical activities which method comprises: applying, either prior to or during physical activities but prior to blister formation, at least 0.02 milliliter (ml) of cyanoacrylate adhesive per square centimeter of surface area of uncut skin which is prone to blister formation; and - maintaining the cyanoacrylate adhesive under conditions which polymerize the adhesive thereby forming an artificial callus which adheres to the surface area of uncut skin where the adhesive was applied wherein the cyanoacrylate, in monomeric form, is represented by formula II:
- the cyanoacrylate adhesive to be applied to the skin has a viscosity of from about 2 to about 1000 centipoise at 20°C. More preferably, the cyanoacrylate adhesive is in monomeric form and has a viscosity of from about 2 to about 20 centipoise at 20°C.
- cyanoacrylate adhesive refers to adhesives based on cyanoacrylate monomers of formula I:
- R is selected from the group consisting of alkyl of 1 to 10 carbon atoms, alkenyl of 2 to 10 carbon atoms, cycloalkyl groups of from 5 to 8 carbon atoms. phenyl, 2-ethoxyethyl, 3-methoxybutyl, and a substituent of the formula:
- 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 the group consisting of benzyl, methylbenzyl and phenylethyl; phenyl; and phenyl substituted with 1 to 3 substituents selected from the group consisting of hydroxy, chloro, bromo, nitro, alkyl of l to 4 carbon atoms, and alkoxy of from 1 to 4 carbon atoms.
- R is an alkyl group of from 1 to 10 carbon atoms including methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, n-pentyl, iso-pentyl, n-hexyl, iso-hexyl, 2-ethylhexyl, n-heptyl, octyl, nonyl, and decyl. More preferably, R is butyl and most preferably, R is n-butyl.
- artificial callus refers to a layer of polymerized cyanoacrylate adhesive formed over and strongly adhering to a defined surface area of skin.
- blister refers to an elevation of the epidermis containing a watery liquid which arises from friction during physical exertion as opposed to some type of disease condition (e.g., chicken pox). Contrarily, the term “blister” does -not refer to irritated skin areas which have not yet blistered (i.e., formed a watery liquid under the epidermis).
- the cyanoacrylate adhesive can be applied to irritated skin areas prior to blister formation as a means for preventing further irritation and, thereby, for retarding blister formation.
- the cyanoacrylate adhesive to be applied onto the skin can be monomeric or partially polymeric.
- partially polymerized cyanoacrylate adhesives are liquid polymers having a higher viscosity than that of the corresponding monomer and, therefore, 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 about 2 to about 1000 centipoise and more preferably from about 2 to about 20 centipoise at 20°C.
- the specific viscosity of the formulation depends on the amount and degree of partially polymerized cyanoacrylate adhesive employed. Such factors are readily ascertainable by the skilled artisan. For example, methods for preparing partially polymerized cyanoacrylate adhesives are disclosed, for example, by Rabinowitz, U.S. Patent No. 3,527,224. Monomeric forms of cyanoacrylate adhesives are often preferred where application is to be made to a large surface. This preference results from the fact that those 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.
- the cyanoacrylate adhesives Upon contact with skin moisture, the cyanoacrylate adhesives will polymerize or, in the case of partially polymerized cyanoacrylate adhesives, will further polymerize, at ambient conditions (skin temperature) over 10 seconds to 60 seconds to provide for a solid layer which forms over and strongly adheres to the surface of the skin.
- This polymer layer serves as an artificial callus and protects the underlying skin against blistering in much the same way as does a natural callus.
- the artificial callus because of its strong binding affinity to skin and because of the durability of the polymerized cyanoacrylate adhesive serves as a substitute for human calluses.
- sufficient cyanoacrylate adhesive is applied onto the surface of the skin to provide for an artificial callus having sufficient thickness to inhibit blister formation.
- the artificial callus has a thickness of at least about 0.1 millimeter (mm) and more preferably at least about 0.3 mm.
- the artificial callus has a thickness ranging from about 0.1 mm to about 0.5 mm and even more preferably from about 0.1 to 0.3 mm. Normally, thicknesses greater than about 0.5 mm are not preferred because shearing forces may disrupt the adhesive formed.
- the artificial callus is preferably formed by application of at least 0.02 ml of cyanoacrylate adhesive per square centimeter of skin.
- cyanoacrylate adhesive formulations employed herein generally comprise monomeric and/or partially polymerized compounds of formula I described above. These compositions are liquid in nature and upon contact with skin moisture will polymerize to provide a solid film or layer over the skin surface.
- the formulations may additionally contain one or more optional additives such as colorants, perfumes, and stabilizers.
- optional additives such as colorants, perfumes, and stabilizers.
- each of these optional additives should be both miscible and compatible with the cyanoacrylate adhesive.
- Compatible additives are those that do not prevent the use of the cyanoacrylate adhesives for their intended use.
- colorants are added so that the polymerized film will contain a discrete and discernable color.
- Perfumes are added to provide a pleasant smell to the formulation.
- Stabilizers are added to minimize in situ polymerization in containers during storage.
- suitable.stabilizers are disclosed in U.S. Patent No. 4,650,826.
- 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 the formulation and causing in situ polymerization.
- the cyanoacrylate adhesive is stored at ambient conditions and is selected to be bacterio ⁇ static. See, for example, Rabinowitz et al., U.S. Patent No. 3,527,224.
- the selected adhesive is bacteriostatic, prolonged storage at ambient conditions is without regard to the sterility of the formulation because there is no adverse build-up of bacteria during storage.
- the above-described formulations are applied onto the skin surface area under conditions suitable for polymerizing the adhesive so as to form an artificial callus.
- sufficient amounts of cyanoacrylate adhesive are employed to permit formation of an artificial callus having a sufficient thickness to inhibit blister formation.
- the artificial callus has a thickness of at least about 0.1 mm and more preferably at least about 0.3 mm.
- Such artificial calluses are formed by applying at least about 0.02 ml of cyanoacrylate adhesive per square centimeter of skin surface area and preferably from about 0.02 ml to about 0.5 ml of cyanoacrylate adhesive per square centimeter of skin surface area.
- the amount of cyanoacrylate adhesive employed does not exceed about 0.05 ml per square centimeter. At concentrations in excess of the maximum preferred concentration, it can, in some cases, take too long for the artificial callus to form, and the resulting callus is subject to shear forces. Additionally, higher concentrations of adhesive create polymers having less than desirable skin adherence and durability characteristics.
- the amount of cyanoacrylate adhesive applied onto the skin surface area can be controlled by the amount of adhesive packaged in a single dose product or by use of a multiple use dispenser which governs the amount of material applied onto the skin.
- the dispenser described by Otake, U.S. Patent No. 4,958,748 is particularly advantageous because it dispenses the adhesive in a controlled drop-wise manner.
- the cyanoacrylate adhesive is applied prior to blister formation. That is, the cyanoacrylate adhesive is applied onto the blister prone areas of the skin prior to initiation of physical activity which would be expected to result in the formation of blisters. Additionally, the cyanoacrylate adhesive can be applied onto blister prone areas at some point during physical activity when blister prone areas begin exhibiting some of the classic signs of blister formation (i.e., irritation, perceived heat and- so forth) .
- the surface skin moisture and temperature are sufficient to initiate polymerization of the adhesive upon application. Thereafter, the skin surface is maintained under suitable conditions to allow polymerization to proceed to formation of an artificial callus.
- polymerization is generally complete within about 10 to about 60 seconds while the skin is maintained at ambient conditions. During this period, the person to whom application of the cyanoacrylate adhesive has been made merely allows the adhesive to form a callus while minimizing any action to prevent the adhesive from being dislodged from that portion of the skin where it was applied (e.g., washing his hands, placing socks on his feet) or to adhere to unintended objects (e.g., gripping an object immediately after application of the adhesive) .
- the callus After the artificial callus has formed, the callus strongly adheres to the skin, is flexible and waterproof thereby permitting the person to conduct the intended activity. In general, the artificial callus will adhere to the skin for a period of about 2-3 days after which time it sloughs off. However, if it is desirable to remove the artificial callus prior to its sloughing off, the artificial callus can be removed with acetone (nail polish remover) .
- the methods of this invention are useful in retarding the formation of blisters.
- the methods of this invention result in the formation of artificial calluses which inhibit blister formation.
- the methods of this invention are particularly suited for retarding blister formation in people who are prone to blister formation.
- Example 1 A cyanoacrylate adhesive formulation was prepared in monomeric form using n-butyl ⁇ -cyano- acrylate of formula II above. The formulation was placed into the dispensing device described by Otake, U.S. Patent No. 4,958,748. Three drops of the formulation were placed drop-wise onto the palm of the hand in an area prone to blister formation of about 2 square centimeters in area so as to provide about 0.02 ml of adhesive per square centimeter. The hand was held palm up for about 1 minute. At this time an artificial callus had formed over this surface.
Abstract
A cyanoacrylate adhesive is applied to the skin areas prone to blistering either prior to or during physical activities but prior to blister formation.
Description
METHODS FOR RETARDING BLISTER FORMATION BY USE OF CYANOACRYLATE ADHESIVES
BACKGROUND OF THE INVENTION
Field of the Invention
The present invention is directed to methods for retarding blister formation by use of cyanoacrylate adhesives that can be applied to skin areas prone to blistering prior to blister formation.
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:
wherein R is an alkyl or other 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.
The suggested medical uses for cyanoacrylate adhesives have been limited to surgical environments wherein the cyanoacrylate adhesives are utilized as an alternative to sutures and are employed in a sterile environment. Specifically, in surgical environments, the cyanoacrylate adhesive is applied to separate sections of soft tissue. The cyanoacrylate adhesive.
in the presence of water found in soft tissue, bonds to the skin as well as polymerizes so as to join separate sections of soft tissue together.
SUMMARY OF THE INVENTION
The present invention, generally speaking, is a result of the discovery that application of cyanoacrylate adhesives to blister prone areas and subsequent polymerization results in the formation of an artificial callus over the blister prone area thereby retarding the formation of blisters in these areas. More particularly, the application of cyanoacrylate adhesives is only to the surface of the skin and not to cut areas of skin.
Thus, it can be understood that the present invention is directed to methods for inhibiting blister formation by application of a cyanoacrylate adhesive to the skin area prone to blistering prior to blister formation. Accordingly, in one of its method aspects, the present invention is directed to a method for inhibiting blister formation arising from friction during physical activities which method comprises: applying, either prior to or during physical activities but prior to blister formation, a quantity of cyanoacrylate adhesive to a surface area of uncut skin which is prone to blister formation, which quantity of cyanoacrylate adhesive is sufficient to form an artificial callus; and maintaining the cyanoacrylate adhesive under conditions which polymerize the adhesive thereby forming an artificial callus which adheres to the surface area of uncut skin where the adhesive was applied.
wherein the cyanoacrylate, in monomeric form, is represented by formula I:
where R is selected from the group consisting of alkyl of 1 to 10 carbon atoms, alkenyl of 2 to 10 carbon atoms, cycloalkyl groups of from 5 to 8 carbon atoms, phenyl, 2-ethoxyethyl, 3-methoxybutyl, and a substituent of the formula:
where 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 the group consisting of benzyl, methylbenzyl and phenylethyl; phenyl; and phenyl substituted 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.
Preferably R is alkyl of from 1 to 10 carbon atoms and more preferably alkyl of from 2 to 6 carbon atoms. Most preferably, R is n-butyl.
In another of its method aspects, the present invention is directed to a method for inhibiting blister formation arising from friction during physical activities which method comprises:
applying, either prior to or during physical activities but prior to blister formation, at least 0.02 milliliter (ml) of cyanoacrylate adhesive per square centimeter of surface area of uncut skin which is prone to blister formation; and - maintaining the cyanoacrylate adhesive under conditions which polymerize the adhesive thereby forming an artificial callus which adheres to the surface area of uncut skin where the adhesive was applied wherein the cyanoacrylate, in monomeric form, is represented by formula II:
0
In a preferred embodiment, the cyanoacrylate adhesive to be applied to the skin has a viscosity of from about 2 to about 1000 centipoise at 20°C. More preferably, the cyanoacrylate adhesive is in monomeric form and has a viscosity of from about 2 to about 20 centipoise at 20°C.
As used herein, the following terms have the following meanings:
The term "cyanoacrylate adhesive" refers to adhesives based on cyanoacrylate monomers of formula I:
O
where R is selected from the group consisting of alkyl of 1 to 10 carbon atoms, alkenyl of 2 to 10 carbon atoms, cycloalkyl groups of from 5 to 8 carbon atoms.
phenyl, 2-ethoxyethyl, 3-methoxybutyl, and a substituent of the formula:
where 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 the group consisting of benzyl, methylbenzyl and phenylethyl; phenyl; and phenyl substituted with 1 to 3 substituents selected from the group consisting of hydroxy, chloro, bromo, nitro, alkyl of l to 4 carbon atoms, and alkoxy of from 1 to 4 carbon atoms.
Preferably, R is an alkyl group of from 1 to 10 carbon atoms including methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, n-pentyl, iso-pentyl, n-hexyl, iso-hexyl, 2-ethylhexyl, n-heptyl, octyl, nonyl, and decyl. More preferably, R is butyl and most preferably, R is n-butyl.
These cyanoacrylate adhesives are known in the 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 term "artificial callus" refers to a layer of polymerized cyanoacrylate adhesive formed over and strongly adhering to a defined surface area of skin.
The term "blister" refers to an elevation of the epidermis containing a watery liquid which arises from friction during physical exertion as opposed to some type of disease condition (e.g., chicken pox). Contrarily, the term "blister" does -not refer to irritated skin areas which have not yet blistered (i.e., formed a watery liquid under the epidermis). In this invention, the cyanoacrylate adhesive can be applied to irritated skin areas prior to blister formation as a means for preventing further irritation and, thereby, for retarding blister formation.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
The cyanoacrylate adhesive to be applied onto the skin can be monomeric or partially polymeric. In general, partially polymerized cyanoacrylate adhesives are liquid polymers having a higher viscosity than that of the corresponding monomer and, therefore, 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 about 2 to about 1000 centipoise and more preferably from about 2 to about 20 centipoise at 20°C. The specific viscosity of the formulation depends on the amount and degree of partially polymerized cyanoacrylate adhesive employed. Such factors are readily ascertainable by the skilled artisan. For example, methods for preparing partially polymerized cyanoacrylate adhesives are disclosed, for example, by Rabinowitz, U.S. Patent No. 3,527,224.
Monomeric forms of cyanoacrylate adhesives are often preferred where application is to be made to a large surface. This preference results from the fact that those 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.
Upon contact with skin moisture, the cyanoacrylate adhesives will polymerize or, in the case of partially polymerized cyanoacrylate adhesives, will further polymerize, at ambient conditions (skin temperature) over 10 seconds to 60 seconds to provide for a solid layer which forms over and strongly adheres to the surface of the skin. This polymer layer serves as an artificial callus and protects the underlying skin against blistering in much the same way as does a natural callus.
The artificial callus, because of its strong binding affinity to skin and because of the durability of the polymerized cyanoacrylate adhesive serves as a substitute for human calluses.
In general, sufficient cyanoacrylate adhesive is applied onto the surface of the skin to provide for an artificial callus having sufficient thickness to inhibit blister formation. In a preferred embodiment, the artificial callus has a thickness of at least about 0.1 millimeter (mm) and more preferably at least about 0.3 mm. In another preferred embodiment, the artificial callus has a thickness ranging from about 0.1 mm to about 0.5 mm and even more preferably from about 0.1 to 0.3 mm. Normally, thicknesses greater
than about 0.5 mm are not preferred because shearing forces may disrupt the adhesive formed.
In another preferred embodiment, the artificial callus is preferably formed by application of at least 0.02 ml of cyanoacrylate adhesive per square centimeter of skin.
Various parts of the human body are prone to blister formation, including the grip portions of hands and the base of feet. During physical exertion, these parts of the body can be subject to friction by such activities as walking/jogging (feet) , shoveling (hands) . The all too familiar result of such activities, particularly in people not accustomed to such activities, is the formation of blisters in those areas prone to blister formation.
Formulations The cyanoacrylate adhesive formulations employed herein generally comprise monomeric and/or partially polymerized compounds of formula I described above. These compositions are liquid in nature and upon contact with skin moisture will polymerize to provide a solid film or layer over the skin surface.
The formulations may additionally contain one or more optional additives such as colorants, perfumes, and stabilizers. In practice, each of these optional additives should be both miscible and compatible with the cyanoacrylate adhesive. Compatible additives are those that do not prevent the use of the cyanoacrylate adhesives for their intended use.
In general, colorants are added so that the polymerized film will contain a discrete and
discernable color. Perfumes are added to provide a pleasant smell to the formulation. Stabilizers are added to minimize in situ polymerization in containers during storage. Each of these additives are conventional. For example, suitable.stabilizers are disclosed in U.S. Patent No. 4,650,826.
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 the 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.
In applicators suitable for repeated intermittent uses, the cyanoacrylate adhesive is stored at ambient conditions and is selected to be bacterio¬ static. See, for example, Rabinowitz et al., U.S. Patent No. 3,527,224. When the selected adhesive is bacteriostatic, prolonged storage at ambient conditions is without regard to the sterility of the formulation because there is no adverse build-up of bacteria during storage.
Methodology The above-described formulations are applied onto the skin surface area under conditions suitable for polymerizing the adhesive so as to form an
artificial callus. In general, sufficient amounts of cyanoacrylate adhesive are employed to permit formation of an artificial callus having a sufficient thickness to inhibit blister formation. In a preferred embodiment, the artificial callus has a thickness of at least about 0.1 mm and more preferably at least about 0.3 mm. Such artificial calluses are formed by applying at least about 0.02 ml of cyanoacrylate adhesive per square centimeter of skin surface area and preferably from about 0.02 ml to about 0.5 ml of cyanoacrylate adhesive per square centimeter of skin surface area.
In another preferred embodiment, the amount of cyanoacrylate adhesive employed does not exceed about 0.05 ml per square centimeter. At concentrations in excess of the maximum preferred concentration, it can, in some cases, take too long for the artificial callus to form, and the resulting callus is subject to shear forces. Additionally, higher concentrations of adhesive create polymers having less than desirable skin adherence and durability characteristics.
The amount of cyanoacrylate adhesive applied onto the skin surface area can be controlled by the amount of adhesive packaged in a single dose product or by use of a multiple use dispenser which governs the amount of material applied onto the skin. In this regard, the dispenser described by Otake, U.S. Patent No. 4,958,748 is particularly advantageous because it dispenses the adhesive in a controlled drop-wise manner.
For inhibiting the formation of blisters, the cyanoacrylate adhesive is applied prior to blister formation. That is, the cyanoacrylate adhesive is
applied onto the blister prone areas of the skin prior to initiation of physical activity which would be expected to result in the formation of blisters. Additionally, the cyanoacrylate adhesive can be applied onto blister prone areas at some point during physical activity when blister prone areas begin exhibiting some of the classic signs of blister formation (i.e., irritation, perceived heat and- so forth) .
Upon application of the cyanoacrylate adhesive, the surface skin moisture and temperature are sufficient to initiate polymerization of the adhesive upon application. Thereafter, the skin surface is maintained under suitable conditions to allow polymerization to proceed to formation of an artificial callus.
In general, the particular length of time required for polymerization will vary depending upon factors such as the amount of adhesive applied, the temperature of the skin, the moisture content of the skin and the like. However, in a preferred embodiment, polymerization is generally complete within about 10 to about 60 seconds while the skin is maintained at ambient conditions. During this period, the person to whom application of the cyanoacrylate adhesive has been made merely allows the adhesive to form a callus while minimizing any action to prevent the adhesive from being dislodged from that portion of the skin where it was applied (e.g., washing his hands, placing socks on his feet) or to adhere to unintended objects (e.g., gripping an object immediately after application of the adhesive) . After the artificial callus has formed, the callus strongly adheres to the skin, is flexible and waterproof thereby permitting the person to conduct the intended activity.
In general, the artificial callus will adhere to the skin for a period of about 2-3 days after which time it sloughs off. However, if it is desirable to remove the artificial callus prior to its sloughing off, the artificial callus can be removed with acetone (nail polish remover) .
It can now be understood that the methods of this invention are useful in retarding the formation of blisters. In particular, the methods of this invention result in the formation of artificial calluses which inhibit blister formation. As such, the methods of this invention are particularly suited for retarding blister formation in people who are prone to blister formation.
The following example illustrates certain embodiments of the invention but is not meant to limit the scope of the claims in any way.
Example 1 A cyanoacrylate adhesive formulation was prepared in monomeric form using n-butyl α-cyano- acrylate of formula II above. The formulation was placed into the dispensing device described by Otake, U.S. Patent No. 4,958,748. Three drops of the formulation were placed drop-wise onto the palm of the hand in an area prone to blister formation of about 2 square centimeters in area so as to provide about 0.02 ml of adhesive per square centimeter. The hand was held palm up for about 1 minute. At this time an artificial callus had formed over this surface.
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 the scope of the appended claims are intended to be included therein.
Claims
1. A method for inhibiting blister formation arising from friction during physical activities which method comprises: applying, either prior to or during physical activities but prior to blister formation, a quantity of cyanoacrylate adhesive to a surface area of uncut skin which is prone to blister formation, which quantity of cyanoacrylate adhesive is sufficient to form an artificial callus; and maintaining the cyanoacrylate adhesive under conditions which polymerize the adhesive thereby forming an artificial callus which adheres to the surface area of uncut skin where the adhesive was applied; wherein the cyanoacrylate, in monomeric form, is represented by formula I:
where R is selected from the group consisting of alkyl of 1 to 10 carbon atoms, alkenyl of 2 to 10 carbon atoms, cycloalkyl groups of from 5 to 8 carbon atoms, phenyl, 2-ethoxyethyl, 3-methoxybutyl, and a substituent of the formula:
where 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 the group consisting of benzyl, methylbenzyl and phenylethyl; phenyl; and phenyl substituted 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 6 carbon atoms.
3. A method according to Claim 2 wherein R is butyl.
4. A method according to Claim 3 wherein R is n-butyl.
5. A method for inhibiting blister formation arising from friction during physical activities which method comprises: applying, either prior to or during physical activities but prior to blister formation, at least 0.02 ml of cyanoacrylate adhesive per square centimeter of surface area of uncut skin which is prone to blister formation; and maintaining the cyanoacrylate adhesive under conditions which polymerize the adhesive thereby forming an artificial callus which adheres to the surface area of uncut skin where the adhesive was applied wherein the cyanoacrylate, in monomeric form, is represented by formula II:
O CH2=C-C IIO(CH2)3CH3. II
CN
6. The method according to Claim 1 wherein the cyanoacrylate adhesive has a viscosity of from about 2 to about 1000 centipoise at 20°C.
7. The method according to Claim 6 wherein the cyanoacrylate adhesive has a viscosity of from about 2 to about 20 centipoise at 20°C.
8. The method according to Claim 5 wherein the cyanoacrylate adhesive has a viscosity of from about 2 to about 1000 centipoise at 20°C.
9. The method according to Claim 8 wherein the cyanoacrylate adhesive has a viscosity of from about 2 to about 20 centipoise at 20°C.
10. The method according to Claim 1 wherein the cyanoacrylate adhesive is applied at a concentration of at least 0.02 ml per square centimeter of surface area of uncut skin.
11. The method according to Claim 5 wherein the cyanoacrylate adhesive is applied at a concentration of from about 0.02 ml to about 0.05 ml per square centimeter of surface area of uncut skin.
12. The method of Claim 10 wherein the cyanoacrylate adhesive is applied at a concentration of from about 0.02 ml to about 0.05 ml per square centimeter of surface area of uncut skin.
13. The method of Claim 1 wherein the cyanoacrylate adhesive is polymerized by maintaining the cyanoacrylate adhesive on the uncut skin surface for a period of from about 10 to 60 seconds and at ambient skin temperature.
14. The method of Claim 5 wherein the cyanoacrylate adhesive is polymerized by maintaining the cyanoacrylate adhesive on the uncut skin surface for a period of from about 10 to 60 seconds and at ambient skin temperature.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US07/871,558 US5306490A (en) | 1992-04-20 | 1992-04-20 | Methods for retarding blister formation by use of cyanoacrylate adhesives |
US07/871,558 | 1992-04-20 |
Publications (1)
Publication Number | Publication Date |
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WO1993020829A1 true WO1993020829A1 (en) | 1993-10-28 |
Family
ID=25357705
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/US1993/003716 WO1993020829A1 (en) | 1992-04-20 | 1993-04-20 | Methods for retarding blister formation by use of cyanoacrylate adhesives |
Country Status (3)
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US (1) | US5306490A (en) |
AU (1) | AU4033093A (en) |
WO (1) | WO1993020829A1 (en) |
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US5306490A (en) | 1994-04-26 |
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