JPH0649066B2 - Medical adhesive sheet or tape - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to a medical pressure-sensitive adhesive sheet or tape, particularly a medical pressure-sensitive adhesive sheet in which an acrylic pressure-sensitive adhesive layer having hydrophilicity and antibacterial property is provided on a substrate. Or about tape.

(Prior art) As a pressure-sensitive adhesive for medical adhesive sheets or tapes such as patches and adhesive plasters containing a drug in the adhesive, the adhesive to the skin is good and the aging resistance is excellent, and the drug contained is altered. Acrylic pressure-sensitive adhesives have been most frequently used conventionally because they have excellent properties such as not causing irritation and not irritating the skin. The acrylic pressure-sensitive adhesive usually contains an acrylic acid ester (co) polymer or a (co) polymer of an acrylic acid ester and a methacrylic acid ester as a main component.
If necessary, various other monomers are copolymerized to obtain an acrylic pressure-sensitive adhesive having desired properties. Such monomers include (meth) acrylic acid, (meth) acrylamide, (meth) acrylic acid hydroxyalkyl ester, (meth) acrylic acid polyalkylene glycol ester, (meth) acrylic acid glycidyl ester, (meth) Acrylic acid alkoxyalkyl ester, vinyl acetate, etc. For example, a copolymer containing acrylic acid as a copolymer component has good adhesiveness at room temperature. Japanese Patent Office Sho 52
Japanese Patent No. 31405 discloses a patch containing a steroidal anti-inflammatory agent in an adhesive, and the adhesive is a copolymer of alkyl acrylate and acrylic acid. Japanese Patent Application Laid-Open No. 52-18813 also discloses a patch containing a steroidal anti-inflammatory agent as an adhesive, and the adhesive is an alkyl acrylate, (meth) acrylic acid, methyl methacrylate or acetic acid. It is a copolymer composed of vinyl and polyfunctional monomers. Further, JP-A-57-77167 discloses a patch containing nitroglycerin as a drug, and the adhesive is a copolymer of methacrylic acid dodecyl ester, (meth) acrylic acid and vinyl acetate. is there. In addition, JP-A-56-45412
Japanese Patent Publication discloses a drug-containing patch using an adhesive having high drug solubility. The adhesive is a (meth) acrylic ester having an ether bond in the molecule, (meth)
It is a copolymer of acrylic acid and (meth) acrylic acid alkyl ester.

As described above, the medical sheet or tape using the acrylic adhesive has various excellent characteristics such as good adhesion to the skin surface. However, since the above-mentioned conventional acrylic adhesive is essentially insoluble in water or poor in hydrophilicity, such a sheet or tape using the adhesive has the following drawbacks.

It is difficult to attach the sheet or tape to the wet (or wet) surface to be attached. For example, it has poor adhesion to the sweating skin surface. If the amount of sweat is high even after application, remove it.

It is not possible to wash off the adhesive that has extruded from the periphery of the applied sheet or tape to the outside, or the adhesive that remains on the skin surface residue after peeling the sheet or tape with water.

For example, water-soluble drugs in the form of sodium salts, potassium salts, ammonium salts, hydrochlorides, etc. are usually soluble only in water or alcohol. Therefore, it is difficult to dissolve such a drug in an adhesive, and thus it is difficult to prepare an adhesive sheet or tape containing the drug.

Adhesives have poor water absorption capacity and poor breathability, so if a sheet or tape is applied to the skin for a long time, stuffiness may occur. As a result, the skin is easily sensitized to slight irritation caused by a drug and causes a rash.

Bacteria, fungi and other miscellaneous bacteria cause abnormal breeding on the part where the stuffiness has occurred, and rashes due to secondary sensitization are likely to occur.

In order to impart hydrophilicity to acrylic pressure-sensitive adhesives, copolymerization of hydrophilic monomers such as (meth) acrylic acid, acrylamide, and hydroxyalkyl (meth) acrylate has also been carried out. However, such a hydrophilic monomer will not show hydrophilicity unless the adhesive is copolymerized in an amount of 60 mol% or more. When 60 mol% or more of the hydrophilic monomer is copolymerized, the balance between the adhesiveness of the pressure-sensitive adhesive and the internal cohesive force is lost, and as a result, an adhesive residue phenomenon occurs.
Furthermore, the original excellent properties of the acrylic adhesive such as aging resistance and skin irritation are impaired.

(Problems to be Solved by the Invention) The present invention solves the above-mentioned conventional drawbacks, and an object thereof is to provide an acrylic pressure-sensitive adhesive layer having hydrophilicity on a substrate, To provide a medical adhesive sheet or tape having excellent properties.

A sheet or tape that can adhere even to wet (wet) skin surface and does not easily peel off even if it sweats during application.

A sheet or tape that can be easily washed off with water, even if the adhesive sticks out around the sheet or tape when applied and remains on the skin surface after peeling.

An adhesive that can dissolve and contain a water-soluble drug that could not be dissolved in an acrylic adhesive and contained, for example, a drug having a salt form such as sodium salt, potassium salt, ammonium salt, or hydrochloride in a high concentration. Sheets or tapes with agents

A sheet or tape that does not cause stuffiness during application because the pressure-sensitive adhesive has a water-absorbing capacity and / or water permeability, and therefore does not cause rash caused by this stuffiness.

Still another object of the present invention is to provide a medical pressure-sensitive adhesive sheet or tape in which the pressure-sensitive adhesive itself has a bactericidal or antibacterial action and secondary sensitization caused by the growth of microorganisms does not cause a rash. is there. Still another object of the present invention is to provide a medical pressure-sensitive adhesive sheet or tape having a pressure-sensitive adhesive layer provided on the surface thereof, which has the inherent advantages of an acrylic pressure-sensitive adhesive in addition to the above-mentioned excellent properties.

(Means for Solving Problems) The medical adhesive sheet or tape of the present invention is (meth)
A medical pressure-sensitive adhesive sheet or tape in which a layer of a pressure-sensitive adhesive containing a copolymer containing an acrylamide derivative as a main component is provided on at least one side of a substrate, wherein the (meth) acrylamide derivative is a quaternary The saturated hydrocarbon group having an ammonium salt is a monomer in which one of the amide hydrogen atoms of (meth) acrylamide is substituted, whereby the above object is achieved.

The copolymer, which is the main component of the pressure-sensitive adhesive used in the medical pressure-sensitive adhesive sheet or tape of the present invention, contains a (meth) acrylamide derivative as a copolymerization component. This (meta)
An acrylamide derivative is a radical-reactive monomer in which a saturated hydrocarbon group having a quaternary ammonium salt is substituted with one of the amide hydrogen atoms of (meth) acrylamide,
It has the following structural formula: (Wherein R ₁ is H or CH ₃ ; R ₂ is a saturated hydrocarbon group having 1 to 6 carbon atoms; R ₃ , R ₄ and R ₅ are alkyl groups having 1 to 3 carbon atoms; and X is a halogen atom. is there).

Of the compounds represented by the above structural formula, preferred examples include 3 (acrylamido) propyltrimethylammonium chloride, 3 (methacrylamido) propyltrimethylammonium chloride, 3 (acrylamido) isopentyltrimethylammonium chloride,
3 (methacrylamido) propyldimethylethylammonium chloride and the like. Such (meth) acrylamide derivatives are, for example, aminoalkyl (meth)
It can be obtained by adding an alkyl halide to acrylamide. As the halogen of the alkyl halide, Cl, Br,
I etc. are mentioned.

The copolymer, which is the main component of the pressure-sensitive adhesive, includes the second copolymer in addition to the first copolymerization component composed of the (meth) acrylamide derivative.
It contains a copolymerization component. The main component of the second copolymerization component is an alkyl acrylate having 12 or less carbon atoms in the alkyl group and / or a vinyl alcohol fatty acid ester having 12 or less carbon atoms in the alkyl group of the fatty acid. It accounts for 50 mol% or more of the polymerization component. The balance of the second copolymerization component is selected from the group consisting of methacrylic acid alkyl ester, vinylpyrrolidone, diacetone acrylamide, N-alkyl (meth) acrylamide and N-alkoxyalkyl (meth) acrylamide, hydroxyalkyl (meth) acrylate. It is at least one monomer.

The above copolymer contains the first copolymerization component and the second copolymerization component in a molar ratio of 2 to 98 to 60 to 40. First
When the amount of the copolymerization component is too small, the hydrophilicity of the obtained copolymer is insufficient. If the amount is excessive, the water absorbency of the copolymer is too large, so that the adhesive absorbs moisture during storage or when it is prepared into a sheet or tape, and the properties of the adhesive change.

Thus, the content of the first copolymerization component controls the degree of hydrophilicity of the copolymer, and as the proportion of the first copolymerization component increases, the properties of the copolymer change from hydrophilicity to water solubility. However, the degree of hydrophilicity of the copolymer also differs depending on the type of the alkyl group of the acrylic acid alkyl ester or the fatty acid alkyl group of the vinyl alcohol fatty acid ester of the second copolymerization component. For example, when the second copolymerization component is an alkyl acrylate, the smaller the carbon number of the alkyl group, the higher the degree of hydrophilicity.
Further, when the methacrylic acid alkyl ester is added to the second copolymerization component, the degree of hydrophilicity tends to decrease as compared with the case where only the acrylic acid alkyl ester is used. Also, when a water-soluble monomer such as vinylpyrrolidone or diacetone acrylamide is added to the second copolymerization component, the hydrophilicity of the copolymer increases. As described above, the degree of hydrophilicity of the copolymer can be adjusted depending on the kind of the monomer used as the second copolymerization component.

Further, the copolymer containing the first copolymerization component and the second copolymerization component has hydrophilicity and bactericidal (anti) bacterial properties. The bactericidal (anti-) bactericidal property is uniquely increased as the molar ratio of the first copolymerization component is increased.

When a small amount of a polyfunctional monomer is added to the above-mentioned first copolymerization component and second copolymerization component to carry out the copolymerization, the internal cohesive force of the obtained copolymer can be improved. The polyfunctional monomer is a monomer in which (meth) acrylic acid ester groups are substituted at two or more positions at the ends of the molecule. For example, 1-6-
Hexane glycol dimethacrylate is preferably used. When a polyfunctional monomer is contained, a slight amount of cross-linking (fine cross-linking) occurs during the copolymerization, so that the internal cohesive force of the copolymer increases. Therefore, even if a large amount of the plasticizer described later is added, the copolymer does not fluidize, and thus a pressure-sensitive adhesive having a large adhesive force can be obtained. The polyfunctional monomer is added at a ratio of 0.8% by weight or less based on the total polymerizable monomers during the polymerization. If the amount is excessive, the solubility of the resulting copolymer in a solvent such as alcohol or water becomes poor.

The first copolymerization component and the second copolymerization component, and optionally a polyfunctional monomer, are subjected to a polymerization reaction by an ordinary polymerization method such as a solution polymerization method, an emulsion polymerization method or a suspension polymerization method. , A copolymer is obtained. Among them, the solution polymerization method is preferably used. When carrying out solution polymerization, a solvent capable of dissolving the first polymerization component and the second polymerization component at least under the polymerization temperature conditions is selected. As such a solvent,
Alcohol solvents such as methyl alcohol, ethyl alcohol and isopropyl alcohol are preferably used.
Depending on the composition of the monomers to be copolymerized, ethyl acetate,
Methyl ethyl ketone, toluene, etc. may be added in small amounts.

In order to obtain the copolymer, the above-mentioned monomer, catalyst and solvent are charged into a reactor equipped with a reflux condenser and the reaction is carried out while heating and stirring in an inert gas atmosphere. In order to obtain a highly viscous polymer, it is necessary to make the concentration of the monomer in the reaction solution at the initial stage of polymerization as high as possible.
It is adjusted to 90% by weight. As the polymerization reaction proceeds, the viscosity of the reaction solution gradually rises as in the case of normal solution polymerization. When the viscosity of the reaction solution rises rapidly and stirring becomes difficult, a solvent is added appropriately to maintain the reaction solution in an appropriate viscosity state. The catalyst is
A usual radical polymerization catalyst is used. An azobis-based catalyst is particularly preferably used in consideration of the solvent system.
The amount of catalyst is usually in the range of 0.1 to 0.5 mol% based on the total number of monomers. The catalyst is preferably added to the reaction system in appropriate divided portions according to the progress of the polymerization reaction. The reaction time varies depending on the kind of the monomer, but is usually 50 to 80 ° C, preferably 60 to 70 ° C. For example, the first half of the polymerization reaction is 60 ℃
A method in which the reaction is carried out under relatively mild conditions before and after, and the reaction is carried out under temperature conditions around 70 ° C in the latter half is preferably used.
It is preferable to carry out the polymerization reaction for 40 hours or more from the start of the polymerization in order to increase the polymerization rate.

When the copolymer solution thus obtained is applied as it is, depending on the composition of the copolymer, the coating film may become tough and may not function as an adhesive. However, when a suitable plasticizer is added to it, the copolymer becomes soft and tacky. The internal cohesive force also becomes appropriate, and it has viscoelastic properties. As the plasticizer, a water-soluble or hydrophilic liquid having a high boiling point and / or a water-soluble substance having a large water retention property is used. Such plasticizers include, for example, glycerin; diglycerin; propylene glycol; trimethylene glycol; α-butylene glycol; 2.3-butylene glycol; β-butylene glycol; α-amylene glycol; 2.3-
Amylene glycol; 2.4-Amylene glycol; 1
4-Amylene glycol; 1.5-pentanediol; trimethylolethane; polyethylene glycol;
Polypropylene glycol; sugars such as starch sugar and sucrose;
Sorbit; urea; cationic surfactants such as long-chain alkyltrimethylammonium chloride; nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkyl ester, fatty acid diethanolamide, sorbitan alkyl ester; dimethylalkyl betaine, etc. Amphoteric surfactants; liquid amino acids and the like. Of these plasticizers, glycerin and diglycerin are preferably used. Two or more kinds of plasticizers may be mixed and used.

The amount of the plasticizer is the molar ratio of the first copolymerization component and the second copolymerization component, the type and composition of the second copolymerization component, the type of plasticizer,
It depends on the thickness of the pressure-sensitive adhesive layer, the desired degree of tackiness, etc., but is usually 0 to 150% by weight of the copolymer, preferably 40
Is in the range of up to 80% by weight. In other words, the adhesive contains 40-100% by weight of the copolymer and 60% of the plasticizer.
It is contained in a proportion of 0% by weight. The amount of the plasticizer is determined within the above range, mainly by the molar ratio of the first copolymerization component and the second copolymerization component in the copolymer. For example, when butyl acrylate is used as the second copolymerization component and the adhesiveness of the resulting sheet or tape is set to the same level as that of commercially available cellophane tape, the amount of the plasticizer is the same as that of the first copolymerization component and the second copolymerization component.
It changes as follows depending on the molar ratio with the copolymerization component. The molar ratio of the first copolymerization component and the second copolymerization component is 10: 90,3
In the case of 0:70 and 60:40, the plasticizer is contained in the adhesive in a proportion of 0 to 20,30 to 40,40 to 60% by weight, respectively. Although such a value is a guideline for the amount of plasticizer, in practice the degree of tackiness of an adhesive is expressed by combining many factors, so the amount of plasticizer can be determined by testing depending on each case. .
It should be noted that if the plasticizer is added too much, the water absorbency of the pressure-sensitive adhesive becomes too large.

The pressure-sensitive adhesive is usually prepared by adding the above-mentioned copolymer and, if necessary, a plasticizer, but in addition to this, a filler, a polymer additive, etc. are contained within a range that does not impair the characteristics of the copolymer. It may have been done.

The pressure-sensitive adhesive thus obtained has appropriate hydrophilicity, water absorption, and moisture permeability, and also has bactericidal (antibacterial) properties and electrical conductivity. Although there are still many unclear points regarding the mechanism of action, it is speculated that the (meth) acrylamide derivative, which is the first copolymerization component, is one of the main causes of such effects. In the copolymer, the unique properties of the (meth) acrylamide derivative, such as hydrophilicity, are utilized, and the viscoelasticity is exerted by the acrylic acid alkyl ester as the second copolymerization component. It is considered that the components are copolymerized and a molecular chain is formed. In such a copolymer, the polarity of the (meth) acrylamide derivative is considered to be remarkably enhanced. Therefore, even if the second copolymerization component mainly composed of an acrylic acid alkyl ester having poor hydrophilicity is contained in the copolymer in a proportion of 50 mol% or more, the copolymer shows strong hydrophilicity. . Such a copolymer is water-soluble or capable of absorbing a large amount of water, and has properties close to those of a polymer composed only of a (meth) acrylamide derivative, such as being completely soluble in an alcohol solvent. The copolymer can also be made compatible with water-soluble substances such as glycerin in equal weight or more. Such water-soluble substances act as plasticizers and exert the adhesive properties of the adhesive sufficiently. To do.

The adhesive layer is formed on at least one side of the substrate to obtain a desired medical adhesive sheet or tape. When a sheet or tape intended for treatment with a drug is obtained, the drug is mixed in the adhesive. Drugs include anti-inflammatory agents, anti-inflammatory analgesics, antihistamines, anti-allergic agents, bactericidal / antibacterial agents, antifungal agents, blood pressure reducing agents, coronary vasodilators, sedatives, stimulants, anti-vehicle sickness agents, anesthetics, etc. There is.

Examples of the base material include polyurethane, polyurethane-polyamino acid cocondensate, polyethylene, ethylene-vinyl acetate copolymer, ethylene-acrylic acid ester copolymer,
Polyvinyl chloride, non-plastic soft polyvinyl chloride (internal copolymer or blend system), polypropylene, nylon,
Polyester, soluble polyvinyl alcohol, insolubilized polyvinyl alcohol, insolubilized polyvinyl acetal, regenerated cellulose, cellulose ester, cellulose ether, silicone rubber, foamed polyethylene, foamed polyurethane, foamed ethylene-vinyl acetate copolymer, etc. are molded into a film or sheet. Used. In addition, paper, non-woven fabric, woven fabric, knitted fabric, etc. made of natural fibers or synthetic fibers can be used, and a breathable substrate or a non-breathable substrate is appropriately selected according to the purpose. .
Further, it is also possible to use the above-mentioned film, woven fabric or the like in an appropriate combination to perform heavy bonding (lamination) and use as a laminate. For example, a laminate of a stretchable nonwoven fabric made of polyurethane fibers and a polyurethane film, or a laminate of the above nonwoven fabric and a silicone rubber film is preferably used. The laminate having such a structure is excellent in gas permeability and therefore easily permeates water vapor and oxygen, and, on the other hand, has a property of not permeating liquid. In addition, it has excellent mechanical wilting resistance (pasting workability),
Familiar with the skin.

A thin polyurethane film or the like is usually formed by a casting method on a mount (process paper). Since the formed film is highly elastic, in order to maintain the original shape of the substrate through the subsequent processing, it is preferable that the film is processed with the process paper attached. By doing so, for example, it becomes easy to apply an adhesive to the film and to cut the obtained final product into a desired length. It is recommended that the prepared sheet or tape be peeled off after the application because it is easier to apply it on the skin when the application paper remains attached.

The method for forming the pressure-sensitive adhesive or the pressure-sensitive adhesive layer containing a drug on the substrate can be performed by a known method. For example, a direct coating method in which a solution containing a pressure-sensitive adhesive is directly applied to the surface of a base material and dried; the pressure-sensitive adhesive solution is once applied to a flat endless belt having a releasable surface and dried, and then a base is applied to this surface. A direct transfer method or the like is used in which the material is pressure-bonded and peeled off to transfer the adhesive to the surface of the base material. In addition, an indirect transfer method in which a pressure-sensitive adhesive solution is once coated on release paper, dried, and then a substrate is pressure-bonded to the coated surface is also suitably used. In the case of the indirect transfer method, the patch is provided with the release paper attached. A sheet or tape prepared by a method other than the indirect transfer method has its adhesive layer surface covered or protected with silicone release paper or the like, if necessary. Since the adhesive is hydrophilic, if the substrate is made of a hydrophobic material such as polyethylene, polypropylene, polyethylene terephthalate (PET), etc.
It is preferable to perform a corona discharge treatment or the like. The sheet or tape thus obtained is appropriately cut into a desired shape.

The sheet or tape of the present invention is preferably used for medical purposes, such as the following applications: It is directly attached to a wound on a human body to easily protect the wound.

Gauze or a pad for dressing the wound is fixed on the skin surface or used as a large plaster (dressing tape) with gauze.

It is affixed to the surgical site in advance, and surgery is performed from above. In this way, when used as a drape, it is possible to eliminate excessive pre-operative disinfection and prevent infection due to infiltration of various bacteria into the wound during surgery.

When instilling a long time, blood washing, or inserting a tube such as a catheter into the body, fix these intravenous injection needles and tubes on the skin surface.

Fix or protect a fractured part such as a fractured part for the required time so that it does not move.

Keep a member such as a colostomy firmly in place.

By including the drug in the adhesive, it can be used as a therapeutic sheet or tape for the purpose of transdermal absorption therapy.

It is used for beauty purposes such as deep wrinkling of the face, fixing and shaping of hair.

(Function) The pressure-sensitive adhesive used in the present invention has the characteristics of a conventional acrylic pressure-sensitive adhesive and is excellent in hydrophilicity. Therefore, it is possible to adhere the sheet or tape to the wet (wet) skin surface, and it does not easily peel off even if it sweats during application. This is a characteristic that cannot be obtained with conventional acrylic adhesives and rubber adhesives.
Also, when the sheet or tape is attached, for example, if the adhesive sticks out to the surroundings due to the movement of the body or the adhesive remains on the skin after peeling, it can be easily washed and removed with water. is there. In addition, water-soluble drugs such as alkali metal salts, ammonium salts,
A drug in the form of a salt such as hydrochloride can be dissolved at a high concentration. Therefore, a medical adhesive sheet or tape containing a water-soluble drug, which has been difficult to prepare conventionally, can be easily obtained.

The pressure-sensitive adhesive used for the sheet or tape has excellent water absorption and moisture permeability, and its ability is more than 5 times that of conventional acrylic pressure-sensitive adhesives. Therefore, even if a sheet or tape in which a pressure-sensitive adhesive layer is provided on a base material that is impermeable to water vapor is attached to the skin for a long time, almost no rash due to stuffiness is observed. If the substrate itself is permeable to water vapor,
No stuffiness occurs. Furthermore, the adhesive has bactericidal (antibacterial) properties depending on the proportion of the acrylamide derivative in the copolymer, which is the main component of the adhesive. for that reason,
Even if stuffiness occurs during application of the sheet or tape, bacteria and the like do not grow abnormally in that part, and therefore rash due to secondary sensitization does not occur.

Furthermore, since the adhesive has conductivity, it has a large antistatic effect. For example, when a conventional roll-shaped adhesive tape using a highly electrically insulating base material such as polyethylene or polypropylene is unwound, the tape may be charged with static electricity of several thousand to tens of thousands of volts. Therefore, it may adhere to another object or cause a spark discharge before being attached to the object. Sparking also creates a risk of ignition, for example in operating rooms using anesthetic ethers. On the other hand, when the sheet or tape of the present invention is used, there is no such danger because the adhesive has no electrostatic property.

If a polyfunctional monomer is added during the preparation of the copolymer, a pressure-sensitive adhesive having a further excellent internal cohesive force can be obtained due to slight crosslinking. A sheet or tape using such an adhesive does not cause a so-called adhesive cracking phenomenon or adhesive residue phenomenon regardless of the film thickness of the adhesive.

(Examples) The present invention will be described with reference to Examples.

Example 1 Preparation of (A) Copolymer: 6 (g) of 3 (methacrylamido) propyltrimethylammonium chloride as a (meth) acrylamide derivative (first copolymerization component) and butyl acrylate as a second copolymerization component. 89.6 g
(0.7 mol), 0.16-g (0.05 mol%) of 1,6-hexane glycol dimethacrylate as a polyfunctional monomer, and 70 g of ethyl alcohol as a solvent were charged in a reaction vessel (1) under a N ₂ stream, The polymerization reaction was initiated at 60 ° C with stirring. As the polymerization catalyst, 0.33 g of azobisisobutyronitrile was used. The catalyst was dissolved in 100 ml of ethyl acetate, 10 ml of which was added to the reaction vessel to initiate the polymerization. The catalyst solution is added every 4 hours after the start of the polymerization reaction.
10 ml each was added and the reaction was continued for 24 hours. Then, the reaction temperature was adjusted to 70 ° C., and 10 ml of the catalyst solution was added every 3 hours. If the viscosity of the reaction solution increased significantly during the polymerization reaction, especially at the beginning of the polymerization, stirring could become difficult and gelation or runaway reaction might occur. Therefore, 20 to 30 ml of ethyl alcohol was added as appropriate. In this way, the apparent viscosity of the reaction solution was kept below 20,000 cps (centipoise). After the addition of the solvent solution was completed, stirring was continued at the same temperature (70 ° C), and the reaction was terminated 44 hours after the start of the polymerization. The obtained reaction liquid was a colorless and transparent viscous liquid, and the concentration of the contained copolymer was 31.2% and the viscosity was 24,000 cps at 21 ° C.

(B) Preparation of pressure-sensitive adhesive solution: The coating film obtained by coating and drying the copolymer solution obtained in (A) was a slightly hard and non-tacky transparent film. Diglycerin 4 was added as a plasticizer to 100 g of the polymer component in the copolymer solution thus obtained.
7 g was added. Further, it was diluted with ethyl alcohol to obtain an adhesive solution having a polymer concentration of 26% and a viscosity of about 10,000 cps.

(C) Preparation of adhesive sheet: A 33 μm thick polyether polyurethane film was used as a substrate. This film was formed on one side of the process paper by the casting method, and the subsequent processing was performed with the process paper attached.
This process paper is a laminate of high-density bleached kraft paper (80 g / m ² ) and a stretched polypropylene film having a thickness of 30 μm. The polyether-based polyurethane film as the base material is formed on the polypropylene surface side of the process paper.
The base material is in close contact with the process paper, and excessive elongation of the base material during processing is suppressed.

The pressure-sensitive adhesive solution obtained in (A) was applied onto a silicone release paper for pressure-sensitive adhesive transfer coating while controlling the coating gap so that the thickness after drying was 25 μm. This was dried with hot air at 80 ° C. for 4 minutes. The dry adhesive surface and the polyurethane surface of the base material were overlapped with each other, and the space between the two pressure rolls was permeated and pressure-bonded. In this way, an adhesive sheet composite comprising process paper-base material-adhesive-release paper was obtained by the indirect transfer coating method in which the adhesive layer was formed on the release paper and the adhesive layer was transferred to the substrate. This pressure sensitive adhesive sheet composite is cut into a desired size and handled in the form of a composite until use. The adhesive sheet is attached to the target surface by peeling off the release paper at the time of use and adhering to the target surface, or by peeling off the process paper on the back surface after attaching. Remove only the release paper of the composite,
After applying a wound protector such as gauze to a part of the adhesive surface,
Another release paper can be applied to make a bandage with gauze.

The pressure-sensitive adhesive sheet obtained in this example is capable of protecting the wound and preventing infection from the wound by directly adhering to the wound and covering the wound, and is also used for adhesion of the wound. In addition, it is also used to fix and hold medical equipment such as intravenous needles, catheters, colostomys, etc. at a specified location on the human body for a specified time. Furthermore, before the operation, attach it to a relatively large area including the surgical site,
It can also be used as a drape for surgery.

(D) Performance evaluation of adhesive sheet: (1) Adhesion to wet surface of adhesive sheet obtained in (C), (2) Water vapor permeability, and (3) Sterilization of adhesive The test was conducted at. The results are shown in the table below. Each test method is as follows.

(1) Adhesion to wet surface: The pressure-sensitive adhesive sheet composite obtained in the item (C) was cut into a tape having a width of 15 mm and a length of about 200 mm to obtain a pressure-sensitive adhesive tape composite. As the adherend used in the test, a laminate of cellophane and polyethylene film (thickness 50 μm) was used. The cellophane surface side of this laminate was used as the surface to be adhered, and the surface to be adhered was lightly rubbed several times with gauze sufficiently containing water to make it wet. Then, the release paper of the adhesive tape composite was peeled off to expose the adhesive surface. The tape adhesive surface was adhered to the adhered surface within 1 minute after wetting the adhered surface so that about 80 mm or more from the tip of the tape was in contact. However, the other end of the tape is open without bonding. Then, a 2 kg rubber-covered roller was reciprocated once from above the bonded portion to pressurize and press it. Ten minutes after the adhesive tape was pressed onto the adherend, the adherend was hung vertically with the adhesive end of the adhesive tape facing down and the open end facing up. Then, fold the other end (open end) of the adhesive tape 180 °, peel the adhesive tape downward about 20 mm from the folding point, and then apply 10
A load of 0 g was applied. With this load, the time required for peeling the tape adhered to the adherend surface by 50 mm was measured.
This test was performed at 21 ° C.

(2) Water vapor permeability: 20 to 30 ml of distilled water was put into a glass bottle having an opening diameter of 48 mm. The pressure-sensitive adhesive sheet composite obtained in the item (C) was cut into a larger size than the opening of the glass bottle. The release paper was peeled off from the adhesive sheet composite, and the adhesive surface was attached to the periphery so as to cover the opening evenly. Next, while gradually peeling off the process paper, the edge of the adhesive sheet was slightly stretched and attached to the periphery of the opening, and the opening was sealed with the adhesive sheet. A vinyl tape was wrapped around the sealed glass bottle opening several times to complete the attachment state around the opening with an adhesive sheet. After weighing the glass bottle whose opening was sealed with an adhesive sheet to a unit of 0.01 g, it was placed in an atmosphere of 40 ° C and 30% relative humidity for 24 hours.
Left for hours. This was weighed again and the amount of water reduction was calculated. From this value, the amount of water vapor permeation (g) per 1 m ^{2 of the} adhesive sheet was calculated. Water vapor permeability of the base material of the pressure-sensitive adhesive sheet used here was ^{2530g / m 2 / 24Hv / 40} ℃.

(3) Bactericidal property of adhesive: The adhesive sheet composite obtained in (C) is cut into 5 cm square pieces, the release paper is peeled off, and a bacterial cell stock solution containing Staphylococcus aureus on the surface of the adhesive. , The cells were applied so that the amount of cells was about 10 ⁵ . This was left at 35 ° C. for 2 hours in an atmosphere having a humidity such that the surface of the adhesive was not dried. Then, the process paper was removed, and the obtained adhesive sheet was transferred to 100 ml of a separately prepared known cell culture medium and shaken for about 1 minute to transfer the bacteria from the surface of the adhesive to the medium. The number of cells transferred to the medium was measured by a usual method and compared with the number of cells at the time of application. A similar test was performed using Pseudomonas aeruginosa and E. coli instead of S. aureus.

Comparative Example 1 (A) Preparation of adhesive solution: 2-ethylhexyl acrylate 173.0 g (0.94 mol), acrylic acid 4.3 g (0.06 mol) and ethyl acetate 80 g were charged into a reaction vessel, and Example 1
A copolymer was synthesized according to the item (A). However, the amount of azobisisobutyronitrile was 0.41 g. The obtained copolymer solution is transparent and its polymer concentration is 33.1%, 21
The viscosity at ° C was 26,900 cps. When this copolymer solution was applied and dried to form a pressure-sensitive adhesive layer, so-called stringing phenomenon and adhesive residue phenomenon occurred due to lack of internal cohesive force. Therefore, to the copolymer solution, 8 g of a diisocyanate compound (addition product of hexamethylene isocyanate and alkylene glycol) having a molecular weight of about 500 per 100 g of the polymer component was added as a crosslinking agent. Further, it was diluted with ethyl acetate to obtain an adhesive solution with a polymer concentration of 26%.

(B) Preparation of pressure-sensitive adhesive sheet: Using the pressure-sensitive adhesive solution (6 hours after preparation) obtained in the item (A) of this comparative example, a pressure-sensitive adhesive sheet composite was prepared according to the method of the item (C) of Example 1. . However, after the adhesive solution was applied and dried, it was cured at 90 ° C for 10 minutes.

(C) Performance evaluation of pressure-sensitive adhesive sheet: Performed in the same manner as in item (D) of Example 1. The results are shown in the table below.

Comparative Example 2 For comparison with the copolymer obtained in Example 1, (meth)
A copolymer using a typical vinylpyrrolidone as a water-soluble monomer instead of an acrylamide derivative was obtained.

(A) Preparation of adhesive solution: N-vinyl-2-pyrrolidone
33.3 g (0.3 mol), butyl acrylate 89.6 g (0.7 mol), 1.6-hexane glycol dimethacrylic acid ester 0.127 g and ethyl acetate 55 g were charged into a reaction vessel, and the mixture was prepared according to the procedure in Example 1 (A). A polymer was synthesized. The resulting reaction solution was slightly opalescent, had a solids concentration of 28.6% and a viscosity at 21 ℃ of 21,600 cps.
Met. The pressure-sensitive adhesive layer obtained by applying and drying this solution has a considerable viscosity, but since it seems that the adhesive force is still insufficient, a plasticizer was added. Polypropylene glycol was used as a plasticizer, and was added at a ratio of 15 g to 100 g of the polymer component of the copolymer solution. Furthermore, it was diluted with ethyl acetate to obtain an adhesive solution with a polymer concentration of 25%.

(B) Preparation of adhesive sheet: An adhesive sheet composite was prepared by the method of Example 1 (C) using the adhesive solution obtained in this Comparative Example (A).

(C) Performance evaluation of pressure-sensitive adhesive sheet: Performed in the same manner as in item (D) of Example 1. The results are shown in the table below.

Example 2 Preparation of (A) Copolymer: The same as in Example 1 (A).

(B) Preparation of pressure-sensitive adhesive solution: The same as in Example 1 (B).

(C) Preparation of adhesive sheet: Washi paper (50 g / 50 g) made of rayon / manila hemp fiber (70:30) as a base material and having a thickness of 120 μm
m ² ) was used. The pressure-sensitive adhesive solution obtained in the item (B) of this Example was applied and dried on a release paper for pressure-sensitive adhesive transfer coating so that the thickness after drying was 40 μm. Two sheets of release paper having such a pressure-sensitive adhesive layer were prepared and pressure-bonded with the pressure-sensitive adhesive layer inside with the base material sandwiched between them to obtain a sandwich-shaped double-sided pressure-sensitive adhesive sheet.

Such a double-sided pressure-sensitive adhesive sheet is used in the state of a sheet or cut into a tape shape as appropriate. For example, it is suitably used for holding and fixing a menstrual pad, fixing overlapping portions of diapers, fixing the end portion of a bandage or the like.

Example 3 Preparation of (A) Copolymer: 3 (acrylamide) propyltrimethylammonium chloride 51.8 g (0.25 mol) as a (meth) acrylamide derivative, and 2-ethylhexyl acrylate 55.2 g (0.3 mol) as a second copolymerization component. Example 1 (A) was also charged with 38.7 g (0.45 mol) of vinyl acetate, 0.05 g (0.015 mol%) of trimethylolpropane trimethacrylate as a polyfunctional monomer, and 70 g of ethyl alcohol as a solvent.
The polymerization reaction was carried out in the same manner as in the above section. The obtained reaction liquid was transparent, the polymer concentration was 30.6%, and the viscosity at 21 ° C was 20,900 cps.

(B) Preparation of pressure-sensitive adhesive solution: 20 g of glycerin and 30 g of polypropylene glycol as a plasticizer were added to 100 g of the polymer component in the copolymer solution obtained in the item (A). Further, it was diluted with isopropyl alcohol to obtain an adhesive solution having a polymer concentration of 26%.

(C) Preparation of pressure-sensitive adhesive sheet: A film in which unplasticized soft polyvinyl chloride (softness: 100% polyvinyl chloride dioctyl phthalate (DOP) 43 phr equivalent product) is calendered to a thickness of 75 μm is used as a base material. I was there. The adhesive solution obtained in the section (A) of this example has a thickness of 25 μm after drying.
Was coated on a release paper so that By the indirect transfer coating method, a pressure-sensitive adhesive layer was formed on the above-mentioned substrate according to the item (C) of Example 1 to obtain a pressure-sensitive adhesive sheet having a pressure-sensitive adhesive layer surface protected by release paper.

Such an adhesive sheet is suitably used as a gauze-attached first-aid bandage or a wound bandage. To make a bandage,
For example, while peeling off the release paper, a release agent is applied to the back surface of the base material, wound on a roll core, and then cut into 10 to 20 mm wide slices. For example, polyoctadecyl ethylene urea is used as a release agent, and usually about 0.2 g per 1 m ²
Is applied to the surface of the substrate. The pressure-sensitive adhesive sheet of this embodiment is also used as a pressure-sensitive drape for a sheet having a size of 25 to 1000 cm ² .

Example 4 Preparation of (A) Copolymer: 10 (3.6 mol) of 3 (acrylamido) propyltrimethylammonium chloride as a (meth) acrylamide derivative, and 73.6 g (0.4 mol) of 2-ethylhexyl acrylate as a second copolymerization component. Then, 16.9 g (0.1 mol) of diacetone acrylamide, 0.25 g (0.08 mol%) of polyethylene glycol dimethacrylic acid ester as a polyfunctional monomer, and 110 g of ethyl alcohol as a solvent were charged in a reaction vessel, and the procedure of Example 1 (A) was performed. The polymerization reaction was carried out in the same manner as in. However, the amount of the catalyst was 0.41 g, and this was dissolved in 50 ml of ethyl acetate and 50 ml of ethyl alcohol before use. The obtained copolymer solution was a slightly pale yellow transparent solution, and the polymer concentration was 33.8% and the viscosity at 21 ℃ was 23,200.
It was cps.

(B) Preparation of drug-containing pressure-sensitive adhesive solution: The copolymer solution obtained in (A) is applied and dried to obtain a slightly hard resin-like coating film having no tackiness.

Then, 40 g of glycerin and polyethylene glycol (molecular weight about 500) were added to the obtained copolymer solution as plasticizers.
g was added to 100 g of polymer component. Benzalkonium chloride 1.0g, dibasic sodium phosphate 3.0g
And 0.5 g of acrinol was prepared, these were dissolved in a small amount of water and added to the copolymer solution. Furthermore, it was diluted with this ethyl alcohol to obtain a drug-containing adhesive solution having a polymer concentration of 28%.

(C) Preparation of pressure-sensitive adhesive sheet: thickness of ethylene-vinyl acetate (70:30) copolymer as a substrate formed by T-die extrusion method
A 45 μm film was used. This film has been previously subjected to corona discharge treatment on one side. Example (B)
The thickness of the adhesive solution containing the drug obtained in Section 30 after drying is 30μ
It was coated on release paper so that it would be m. By the indirect transfer coating method, a pressure-sensitive adhesive layer was formed on the above-mentioned substrate according to the item (C) of Example 1 to obtain a pressure-sensitive adhesive sheet having a pressure-sensitive adhesive layer surface protected by release paper.

The pressure-sensitive adhesive sheet of this example has bactericidal and antifungal properties, and thus is suitable for use in athlete's foot diseases and fungal skin diseases. When the pressure-sensitive adhesive sheet is used, it is cut into a desired size and used.

Example 5 Preparation of (A) Copolymer: The same as in Example 4 (A).

(B) Preparation of drug-containing adhesive solution: 30 g of diglycerin, 30 g of octadecyltrimethylammonium chloride and 10 g of polypropylene glycol as a plasticizer were added to 100 g of the polymer component in the copolymer solution obtained in this Example (A). added. Further, 4.0 g of diphenhydramine hydrochloride, which is an antihistamine, was added as a drug and diluted with ethyl alcohol to obtain a drug-containing adhesive solution having a polymer concentration of 28%.

(C) Preparation of pressure-sensitive adhesive sheet: Dry bond method of non-woven fabric composed of polyether-based polyurethane fibers (average fiber length 18 mm, weight 30 g per m ^{2 of} non-woven fabric) as a base material and polyether-based polyurethane film (thickness 20 μm) Was used. The drug-containing pressure-sensitive adhesive solution obtained in the item (B) of this Example was applied onto release paper so that the thickness after drying was 40 μm. Using this, an indirect transfer coating method was used to form a pressure-sensitive adhesive layer on the non-woven fabric side of the substrate according to the item of Example 1 (C).

Example 6 Preparation of (A) Copolymer: 3 (acrylamide) isopentyltrimethylammonium chloride 46.5 g (0.2 mol) as a (meth) acrylamide derivative, butyl acrylate 76.8 g (0.6 mol) as a second copolymerization component, and N
-Vinyl-2-pyrrolidone 22.2 g (0.2 mol), 1.6-hexane glycol diacrylic acid ester 0.181 g (0.08 mol%) as a polyfunctional monomer, and ethyl alcohol 85 g as a solvent were charged into a reaction vessel. Example 1 (A)
Polymerization reaction was carried out according to the method described in the item 1. However, the amount of catalyst is 0.
It was 41 g. The obtained copolymer solution was a colorless transparent viscous liquid, the polymer concentration was 29.3%, and the viscosity at 21 ° C was 28,300 cps.

(B) Preparation of drug-containing pressure-sensitive adhesive solution: 35 g of glycerin as a plasticizer was added to 100 g of the polymer component in the copolymer solution obtained in the item (A) of this Example. Further, as an agent, an anti-inflammatory analgesic agent comprising 5.0 g of salocol, 2.0 g of methyl salicylate, 5.0 g of 1-menthol, 1.0 g of dl-camphor, 0.1 g of thymol and 0.5 g of glycyrrhetinic acid was added. Further dilute with ethyl alcohol to give a polymer concentration of 28
% Drug-containing adhesive solution was obtained.

(C) Preparation of pressure-sensitive adhesive sheet: A woven fabric having lateral stretchability, in which cotton yarn was used as the warp system and spandex core yarn was used as the weft system, was used as the base material. One side of this base material was quilled, and then a sealing / priming process was performed. For sealing and undercoating, a toluene solution of a graft polymer (trade name MG-30; grafting rate 30%) in which methyl methacrylate was graft-polymerized on natural rubber was used with a kiss roll coater, and the graft polymer was 1 m. ^It was applied in an amount of 30 g per ² parts. Next, the drug-containing pressure-sensitive adhesive solution obtained in the item (B) of this Example was applied onto release paper so that the thickness after drying was 80 μm. Using this, an indirect transfer coating method was used to form a pressure-sensitive adhesive layer on the processed surface of the substrate according to the item of Example 1 (C). In this way, an anti-inflammatory and analgesic pressure-sensitive adhesive sheet having the surface of the pressure-sensitive adhesive layer protected by a release paper was obtained.

Example 7 (A) Preparation of adhesive solution: 3 (acrylamide) isopentyltrimethylammonium chloride 81.4 g (0.35 mol) as a (meth) acrylamide derivative, butyl acrylate 70.4 g (0.55 mol) as a second copolymerization component, and EXAMPLE 1 19.8 g (0.1 mol) of 2-ethylhexyl methacrylate, 0.113 g (0.05 mol%) of 1.6-hexane glycol diacrylate as a polyfunctional monomer and 75 g of isopropyl alcohol as a solvent were charged in a reaction vessel. The polymerization reaction was carried out according to the method of section (A).
However, the amount of the catalyst was 0.41 g, and this was dissolved in 50 ml of ethyl acetate and 50 ml of isopropyl alcohol before use. The obtained copolymer solution was a transparent solution having a polymer concentration of 30.3% and a viscosity at 21 ° C of 25,200 cps.

(B) Preparation of drug-containing adhesive solution: 30 g of glycerin as a plasticizer and dimethylalkylbetaine (trade name Anon AB; manufactured by NOF CORPORATION) as a plasticizer per 100 g of the polymer component in the copolymer solution obtained in this Example (A). ) 30 g was added. As the drug, 10.0 g of diclofenac sodium, which is an anti-inflammatory agent, was used, and this was dissolved in a small amount of water and added to the copolymer solution. Furthermore, it was diluted with isopropyl alcohol to obtain a drug-containing adhesive solution having a polymer concentration of 28%.

(C) Preparation of pressure-sensitive adhesive sheet: As a substrate, a film having a thickness of 50 μm and made of a copolycondensate of ether polyurethane and γ-alkyl-1-glutamate (80:20) was used.
This film was cast on one side of the process paper, and processing was performed with the process paper attached. The process paper is of the same quality as that used in Example 1 (C). The drug-containing pressure-sensitive adhesive solution obtained in the item (B) of this example was applied onto release paper so that the thickness after drying was 40 μm. A pressure-sensitive adhesive layer was formed on the substrate by the indirect transfer coating method according to Example 1 (C). When the thus obtained adhesive sheet composite (adhesive sheet having process paper and release paper) is used, the release paper is peeled off and temporarily attached to the affected area of the skin, and the process paper is peeled off and then re-pressed. Preferably.

Example 8 (A) Preparation of copolymer: 3 (methacrylamido) propylmethylammonium chloride 33.1 g (0.15 mol) as a (meth) acrylamide derivative, and 2-ethylhexyl acrylate 36.8 g (0.2) as a second copolymerization component. Mol), butyl acrylate 51.2 g (0.4 mol), diacetone acrylamide 25.4 g (0.15 mol) and N-vinyl-2-pyrrolidone 11.1 g (0.10 mol), polyethylene glycol dimethacrylate as a polyfunctional monomer
0.28 g (0.03 mol%) and 80 g of ethyl alcohol and 10 g of ethyl acetate as a solvent were charged in a reaction vessel, and a polymerization reaction was carried out according to the method of Example 1 (A). However, the amount of catalyst was 0.41 g. The obtained copolymer solution was a colorless and transparent solution having a polymer concentration of 31.9% and a viscosity at 21 ° C of 22,100 cps.

(B) Preparation of pressure-sensitive adhesive solution: 20 g of glycerin, 25 g of polypropylene glycol and octadecyltrimethylammonium chloride (cationic AB; NOF Corporation) as a plasticizer per 100 g of the polymer component in the copolymer solution obtained in the section (A) of this Example. 10 g) was added. Further, it was diluted with isopropyl alcohol to obtain an adhesive solution having a polymer concentration of 26.0%.

(C) Preparation of adhesive sheet: A soft polyethylene film having a thickness of 60 μm was used as a substrate. This film has been previously subjected to corona discharge treatment on one side. The pressure-sensitive adhesive solution obtained in the section (B) of this Example had a thickness of 40 after drying.
It was coated on a release paper so as to have a thickness of μm. By the indirect transfer coating method, a pressure-sensitive adhesive layer was formed on the above-mentioned substrate according to the item (C) of Example 1 to obtain a pressure-sensitive adhesive sheet having a pressure-sensitive adhesive layer surface protected by release paper.

Such an adhesive sheet is used not only as a so-called vinyl bandage, but also for protecting and treating the inflamed part of the oral cavity and for holding and fixing it in a predetermined place such as an artificial anus for a long time.

Example 9 Preparation of (A) Copolymer: 2 (3 g) of (methacrylamido) propyltrimethylammonium chloride as a (meth) acrylamide derivative, butyl acrylate 64.0 (0.5 mol) as a second copolymerization component, and Example 2 73.6 g (0.4 mol) of 2-ethylhexyl acrylate, 0.100 g (0.04 mol%) of 1.6-hexane glycol dimethacrylate as a polyfunctional monomer, and 80 g of isopropyl alcohol as a solvent were charged in a reaction vessel. The polymerization reaction was carried out according to the method of section 1 (A). However, the amount of the catalyst was 0.38 g, and a mixed solvent of isopropyl alcohol and ethyl acetate (60:40) was used as a diluting solvent. The resulting copolymer solution had a polymer concentration of 28.7
%, A colorless transparent solution having a viscosity at 21 ° C. of 21,400 cps.

(B) Preparation of adhesive solvent: 20 g of glycerin and 10 g of glycerin monostearate as a plasticizer were added to 100 g of the polymer component of the copolymer solution obtained in the item (A) of this Example. Further, the mixture was diluted with a mixed solution of isopropyl alcohol and ethyl acetate (1: 1) to obtain an adhesive solution having a polymer concentration of 25.0%.

(C) Preparation of adhesive tape: average fiber length of 20 mm as base material
Rayon non-woven fabric (thickness 150 μm; about 40 g per 1 m ² )
Was used. This rayon nonwoven fabric has a release treatment on one side in advance. This stripping treatment was performed by applying a methyl ethyl ketone solution as a stripping agent using a gravure coater and drying. As the release agent, an AB type block polymer (Modiper F; manufactured by NOF Corporation) containing a fluorinated alkyl group as one component was used. This release agent was made into 30% methyl ethyl ketone solution, and 1.3g / m on rayon non-woven fabric.
^It was applied so as to be ² .

The pressure-sensitive adhesive solution obtained in the item (B) of this example was coated on a release paper so that the thickness after drying was 40 μm. The release paper is peeled off while transferring the adhesive layer coated on the release paper to the non-release treated surface side of the above base material, and the obtained adhesive sheet is wound on a paper roll core body by about 10 m (standard length). I took it. This roll-shaped pressure-sensitive adhesive sheet was appropriately cut into slices so as to have a desired width such as 10 mm, 15 mm, and 25 mm to obtain a pressure-sensitive adhesive tape.

The roll-shaped adhesive tape obtained in this example can be used as a plaster for various purposes. For example, it is preferably used for holding / fixing gauze for treating an injured part, pulling / fixing for adhering a small wound, and preventing / fixing the bandage by winding the bandage treatment part from the outside. In addition to such medical use, it is preferably used for beauty purposes such as wrinkling of the face and bundling of hair.

(Effects of the Invention) According to the present invention, the acrylic adhesive having the excellent characteristics of the acrylic adhesive, such as excellent adhesiveness, high internal cohesive force, and low deterioration, is also excellent in hydrophilicity. A medical adhesive sheet or tape having an adhesive can be obtained. Since this adhesive has hydrophilicity, it can adhere a sheet or tape to a wet (wet) skin surface, and does not easily peel off even if it sweats during application. Even if the adhesive sticks out to the surroundings when the sheet or tape is attached, or if the adhesive remains on the skin after peeling, it can be easily washed and removed with water. A water-soluble drug can be dissolved in the adhesive at a high concentration.
Therefore, it is possible to easily obtain a therapeutic adhesive sheet or tape containing a high amount of a water-soluble drug, which has been difficult to prepare conventionally.

This adhesive has excellent water absorption and moisture permeability, so that even if a sheet or tape is applied to the skin for a long time, rash due to stuffiness hardly occurs. Furthermore, since the adhesive itself has bactericidal (antibacterial) properties, it does not cause irritation due to secondary sensitization of bacteria and the like. Further, since the adhesive itself has conductivity, it has a large antistatic effect. Therefore, for example, when the roll-shaped adhesive tape is rewound, it may be attached to an unintended object due to static electricity, or there is a risk of ignition due to spark discharge. Absent.

Such an adhesive sheet or tape for medical use is used as a sheet-shaped or tape-shaped adhesive plaster for protecting an injured part or fixing a fractured part, etc. Fixed on the skin surface,
It is also suitably used for fixing / adhering a medical member such as an artificial anus to a predetermined place. It can also be used for drape during surgery. It can also be used as a patch containing various drugs, and in particular, a patch containing a water-soluble drug in a high content can be easily obtained. It is also used for beauty purposes such as deepening wrinkles on the face, fixing and shaping hair.

Claims (8)

[Claims] 1. A medical pressure-sensitive adhesive sheet or tape in which a layer of a pressure-sensitive adhesive containing a copolymer containing a (meth) acrylamide derivative as a copolymerization component as a main component is provided on at least one side of a base material. (Meth) acrylamide derivative has 4
A saturated hydrocarbon group having a primary ammonium salt is (meth)
Substituted with one of the amide hydrogen atoms of acrylamide,
A medical adhesive sheet or tape which is a monomer of the following general formula. (Wherein R ₁ is H or CH ₃ ; R ₂ is a saturated hydrocarbon group having 1 to 6 carbon atoms; R ₃ , R ₄ and R ₅ are alkyl groups having 1 to 3 carbon atoms; and X is a halogen atom. is there.) 2. The copolymer, in addition to the copolymerization component composed of the (meth) acrylamide derivative, an acrylic acid alkyl ester having an alkyl group having 12 or less carbon atoms as a second copolymerization component and / or Claims containing a monomer whose main component is a vinyl alcohol fatty acid ester in which the alkyl group of the fatty acid has 12 or less carbon atoms
The sheet or tape described in the item. 3. The sheet or tape according to claim 1, wherein the first copolymerization component is contained in the copolymer in a proportion of 2 mol% to 60 mol%. 4. The method according to claim 1, wherein the second copolymerization component is contained in the copolymer in a proportion of 98 mol% to 40 mol%. Sheet or tape. 5. The sheet or tape according to claim 2, wherein the second copolymerization component contains the acrylic acid alkyl ester and / or the vinyl alcohol fatty acid ester in a proportion of 50 mol% or more. . 6. The sheet or tape according to claim 1, wherein the adhesive contains a plasticizer having an affinity for water. 7. The adhesive comprises 40 to 10 of the copolymer.
A sheet or tape according to claim 1 or 6, containing 0% by weight and a plasticizer in an amount of 60 to 0% by weight. 8. The sheet or tape according to claim 1, wherein the adhesive contains a drug.