JPH09176604A - Self-adhesive composition and patch prepared by using the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a self-adhesive compsn. excellent in self-adhesive power, cohesive power, water resistance, sticking properties, etc., by mixing an N- vinyl-2-pyrrolidone copolymer with a maleic anhydride monoalkyl ester polymer. SOLUTION: This self-adhesive compsn. is prepd. by mixing a water-insol. copolymer having N-vinyl-2-pyrrolidone units (e.g. an N-vinyl-2-pyrrolidone/2- ethylhexyl acrylate copolymer) with a polymer having maleic anhydride monoalkyl ester unit (e.g. a monobutyl ester of a methoxyethylene/maleic anhydride copolymer). The addition of a cross-linker (e.g. a metal alcoholate) to the compsn. server to improve the cohesive power, etc., of the compsn. If necessary additives such as a plasticizer (e.g. butyl stearate) and a tackifier (e.g. a hydrogenated rosin ester) may be added further. The obtd. compsn. is useful for producing a patch.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a pressure-sensitive adhesive composition having excellent patchability and low skin irritation, and a patch using the same.

[0002]

BACKGROUND OF THE INVENTION Patches are preparations that are continuously administered by being applied to the skin and percutaneously absorbing the drug. Therefore, the absorbability of the drug and the adhesiveness to the skin are important performances. There is.

The time for applying such a patch varies depending on the preparation, but it is generally 24 hours and 48 for a long one.
Some take time. In the meantime, it is necessary to make sure that it is in close contact with the skin and that the required amount of drug is absorbed.

However, during application, the adhesive may be peeled off due to insufficient adhesive strength, or conversely, the adhesive strength may be so strong that irritation may occur on the skin during peeling. In addition, there are many problems such as stickiness at the time of application and adhesive residue on the skin due to lack of cohesive strength, and it is not easy to provide a patch having good adhesive properties.

In order to solve such problems, a patch has been disclosed in which the pressure-sensitive adhesive layer is composed of a pressure-sensitive adhesive base, a plasticizer, silicic acid anhydride and a drug (JP-A-3-291218). However, in order to obtain a sufficient cohesive force, a large amount of silicic acid anhydride is required, and since the silicic acid anhydride has a low bulk density, it tends to scatter, and it is difficult to handle it accurately and cleanly.

Further, silicic acid anhydride easily aggregates and precipitates in a solvent, and it has been difficult to uniformly mix a large amount of silicic acid anhydride.

In order to achieve the same object, a pressure-sensitive adhesive composition comprising a pressure-sensitive adhesive comprising a copolymer having an amide compound as a constituent and a polymer having maleic anhydride as a constituent. A percutaneous absorption preparation used is disclosed (JP-A-7-26231).

In this preparation, a sufficient amount of cohesive force can be obtained with a small amount of a polymer containing maleic anhydride as a constituent, and it is easy to uniformly mix them. However, since maleic anhydride is hydrolyzed with water to open the ring, it is hydrolyzed due to perspiration and moisture divergence during application to lower the cohesive force, and the stable cohesive force imparting effect cannot be maintained. In addition, it was necessary to pay attention to the humidity control during storage.

Further, conventionally, a polymer having maleic anhydride as a constituent component has been mainly used in combination with a water-soluble polymer substance, and has been used for plasters such as poultices and poultices. However, since these patches use a water-soluble polymer, the plaster easily slumps due to heat, sweat, etc., and is crosslinked with polyvalent metal ions, etc., or a complex is formed using an additive to maintain shape retention. It was necessary to raise the height and prevent sagging.

As a patch composition using such a sagging prevention means, a patch composition containing a water-soluble polymer and a primary alcohol monoester of a methoxyethylene-maleic anhydride copolymer is disclosed. (Japanese Patent Laid-Open No. 63-
135328). However, in the case of this patch composition, the cohesive force is insufficient, and the cohesive force is not sufficient, and the cohesive force cannot be maintained especially when a plasticizer is added. In addition, in the case of long-term application or application during exercise, the adhesive strength is poor, so that peeling occurs during application and the application area required for drug administration cannot be secured.

[0011]

SUMMARY OF THE INVENTION In view of the above, the present invention has a good adhesive force and a stable cohesive force, has low skin irritation, has a well-balanced adhesive property, and is also water resistant. An object is to provide an excellent pressure-sensitive adhesive composition and a patch using the same.

[0012]

The pressure-sensitive adhesive composition of the present invention comprises a water-insoluble copolymer containing N-vinyl-2-pyrrolidone as a constituent and a monoalkyl ester of maleic anhydride as a constituent. It is characterized by being united. Further, the patch of the present invention is characterized in that a pressure-sensitive adhesive layer comprising the above-mentioned pressure-sensitive adhesive composition and a drug is laminated on one surface of a support. Hereinafter, the present invention will be described in detail.

The copolymer used in the present invention is not particularly limited as long as it is a water-insoluble copolymer having N-vinyl-2-pyrrolidone as a constituent component, and examples thereof include alkyl acrylate and methacrylic acid. Copolymer with alkyl ester (hereinafter, these are abbreviated as "(meth) acrylic acid alkyl ester"); Copolymer with ethylene and vinyl acetate; Polybutene, polyisoprene, styrene-isoprene-styrene copolymer Examples thereof include N-vinyl-2-pyrrolidone adducts of rubber-based polymers such as polymers, and copolymers with (meth) acrylic acid esters are particularly preferable.

When the content of N-vinyl-2-pyrrolidone is low, the effect of imparting cohesive force by the addition of the polymer having a monoalkyl ester of maleic anhydride as a constituent component is hardly exhibited, and when the content is high, the adhesive force is increased. Since the water resistance of the pressure-sensitive adhesive becomes poorer as it lowers, it is 1-60% in the copolymer.
Weight% is preferable, and more preferably 5 to 30% by weight.

The above-mentioned (meth) acrylic acid alkyl ester is not particularly limited as long as it is copolymerizable,
For example, methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate,
Hexyl (meth) acrylate, octyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, isooctyl (meth) acrylate, decyl (meth) acrylate, isodecyl (meth) acrylate, lauryl (meth) acrylate , (Meth) tridecyl acrylate, (meth)
Examples thereof include stearyl acrylate and the like, and these may be used alone or in combination.

In the above-mentioned copolymer of (meth) acrylic acid alkyl ester, a polyfunctional monomer is added in an amount of 0.005 to 0.1% in the copolymer for the purpose of enhancing the cohesive force of the copolymer (adhesive).
You may copolymerize in the range of 5 weight%.

The polyfunctional monomer is not particularly limited, and examples thereof include 1,6-hexane glycol dimethacrylate, tetraethylene glycol diacrylate, trimethylolpropane triacrylate, divinylbenzene, divinyltoluene and diallyl phthalate.

In order to prepare a copolymer with the above-mentioned (meth) acrylic acid alkyl ester, usually, solution polymerization of the required monomer is carried out in the presence of a polymerization initiator, but the polymerization form is not limited to this. The polymerization reaction conditions are appropriately selected mainly depending on the type of monomer.

For example, when carrying out solution polymerization, ethyl acetate or other general polymerization solvent is added to a predetermined amount of a required monomer, and azobis type or peroxide type is added in a reactor equipped with a stirrer and a cooling device. In the presence of a polymerization initiator such as the above, the reaction may be performed in a nitrogen atmosphere at 70 to 90 ° C. for 8 to 40 hours.
The monomers and solvent may be added all at once,
You may divide and input appropriately. It is preferable to add the polymerization initiator appropriately in divided portions according to the progress of the reaction.

Examples of the azobis-based polymerization initiator include 2,2'-azobisisobutyronitrile and 1,1 '.
-Azobis (cyclohexane-1-carbonitrile),
2,2'-azobis (2,4-dimethylvaleronitrile) and the like can be mentioned. Examples of the peroxide type polymerization initiator include lauroyl peroxide, benzoyl peroxide, di (t-
Butyl) peroxide and the like.

The polymer containing a monoalkyl ester of maleic anhydride as a constituent component added to the pressure-sensitive adhesive is not particularly limited as long as it contains a monoalkyl ester of maleic anhydride. Generally, a copolymer and an adduct with maleic anhydride as follows are first obtained, and then reacted with an alcohol to obtain a polymer having a monoalkyl ester of maleic anhydride as a constituent component. Is not limited to this.

In order to obtain a stable cohesive force, it is preferable to carry out complete esterification because the remaining maleic anhydride moiety reacts with water to cause a decrease in cohesive force. In addition, since the water resistance is increased by the progress of alkylesterification of maleic anhydride even with a small amount, sufficient water resistance can be obtained if it progresses by 50% or more. It is not impossible to use.

Examples of copolymers and adducts with maleic anhydride include copolymers with vinyl ethers such as methoxyethylene and ethoxyethylene; methyl (meth) acrylate, ethyl (meth) acrylate and the like (meta ) Copolymers with acrylic acid alkyl esters; copolymers with styrene; copolymers with polyolefins such as polyethylene and polypropylene; rubber-based polymers such as polybutadiene, polyisoprene, and styrene-isoprene-styrene block copolymers. Examples thereof include maleic anhydride adducts, copolymers with methoxyethylene, copolymers with styrene and maleic anhydride adducts of polyisoprene are preferably used, and among them, copolymers with methoxyethylene are more preferable. It is preferably used.

The molecular weight of the polymer having a monoalkyl ester of maleic anhydride as a constituent is not particularly limited,
Preferably 5000-500000, more preferably
It is 20,000 to 100,000.

Examples of the above-mentioned copolymer of methoxyethylene and maleic anhydride include GANTREZ AN.
(Manufactured by I.S.P.) are commercially available. As grades thereof, AN-119 (intrinsic viscosity 0.1 to 0.5, molecular weight 20000), AN-139 (intrinsic viscosity 1.0 to 1.
4, molecular weight 41,000), AN-149 (intrinsic viscosity 1.
5 to 2.0, molecular weight 50000) and AN-169 (intrinsic viscosity 2.6 to 3.5, molecular weight 67,000) and the like can be mentioned, and AN-119 and AN-139 are preferable.

Examples of the monoalkyl ester of the above-mentioned copolymer of methoxyethylene and maleic anhydride include:
GANTREZ ES (manufactured by I.S.P.) is commercially available, and grades thereof include ES-225 (ethyl ester, 50% ethanol solution), ES-335 (isopropyl ester, 50% isopropanol solution), E.
S-425 (n-butyl ester, 50% ethanol solution), ES-435 (50% isopropanol solution) and the like can be mentioned, and any of them can be preferably used, but particularly preferably ES-225 and ES-425. is there. This GAN
The molecular weight of TREZ ES is 2500 for ES-225.
0, ES-425 is about 30,000.

When the content of the polymer containing the monoalkyl ester of maleic anhydride as a constituent is low, the effect of improving the cohesive strength is low, and when it is high, the cohesive strength of the pressure-sensitive adhesive is improved but the pressure-sensitive adhesive strength is decreased. 0.1 to 200 parts by weight, and more preferably 1 to 100 parts by weight, relative to 100 parts by weight of a water-insoluble copolymer having N-vinyl-2-pyrrolidone as a constituent component. However, there is no limitation in blending more or less than this range in order to obtain good adhesive physical properties.

In the present invention, it is preferable that the pressure-sensitive adhesive composition contains a crosslinking agent. As the cross-linking agent, for example, an isocyanate compound, an organic peroxide,
Organic metal salt, metal alcoholate, metal chelate compound,
Examples thereof include polyfunctional compounds and the like, and are not particularly limited as long as they generally cause chemical crosslinking. Of these, isocyanate compounds are preferred.

The amount of the cross-linking agent added is 1 to 500 parts by weight, more preferably 5 parts by weight, based on 100 parts by weight of the polymer having a monoalkyl ester of maleic anhydride as a constituent.
２００200 parts by weight.

A method for mixing and homogenizing the water-insoluble copolymer containing N-vinyl-2-pyrrolidone as a constituent and the polymer containing a monoalkyl ester of maleic anhydride as a constituent is as follows. A water-insoluble copolymer having vinyl-2-pyrrolidone as a constituent and a polymer having a monoalkyl ester of maleic anhydride as a constituent are mixed,
Although the method of adding the crosslinking agent immediately before the coating step is adopted, the crosslinking agent may be added at the same time when the polymer is mixed.

Examples of the mixing method include a rotary stirring device such as a ball mill and a rotor mill, a rotary blade stirring device such as a propeller mixer, a disper mixer, a paddle mixer and an anchor mixer, and a kneading device such as a planetary mixer. Examples include, but are not limited to, mixing using a stirrer.

If desired, the pressure-sensitive adhesive used in the present invention may contain additives such as tackifiers and plasticizers. Examples of the tackifier include rosin-based resins such as hydrogenated rosin ester, terpene-based resins, petroleum-based resins,
A coumarone-indene resin, a terpene-phenol resin, etc. are mentioned, Preferably it is a rosin resin.

Examples of the plasticizer include cetyl octanoate, hexyl laurate, isopropyl myristate, octyldodecyl myristate, isopropyl palmitate, butyl stearate, octyl stearate, octyl hydroxystearate, ethyl oleate, olein. Fatty acid esters of monohydric alcohols such as decyl acid and myristyl lactate; dibasic acid esters such as diisopropyl adipate, dioctyl adipate, diethyl sebacate, dioctyl sebacate, dioctyl succinate; diethyl phthalate, diheptyl phthalate, phthalic acid Phthalic acid diesters such as octyl; triethyl citrate; propylene glycol dicaprate, glyceryl trioctanoate, tri (octanoic acid / decanoic acid) glyceryl, medium chain fatty acid triglyceride Fatty acid esters of polyhydric alcohols such as lid and fatty acids corresponding to these fatty acid esters; polyhydric alcohols such as glycerin and diglycerin; alkylene glycols having 4 or more carbon atoms; polyalkylene glycols such as polyethylene glycol and polypropylene glycol; allyl alkyl alcohols. Low molecular weight polymethyl vinyl ether; triacetin; liquid polysaccharides;
Liquid cationic surfactants such as alkyl trimethyl ammonium chloride having 12 or more carbon atoms; nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkyl ester, fatty acid diethanolamide, sorbitan alkyl ester, sorbitan polyoxyethylene alkyl ester Agents; amphoteric surfactants such as dimethyl betaine; liquid amino acids and the like, and one or more of these may be added.

Of these, isopropyl myristate, isopropyl palmitate, diethyl sebacate, diisopropyl adipate, fatty acid esters such as medium-chain fatty acid triglyceride, polyethylene glycol, triacetin and triethyl citrate are preferable.

When the content of the above-mentioned plasticizer is small, a sufficient plasticizing effect cannot be obtained, and when it is large, the cohesive force and the adhesive force of the pressure-sensitive adhesive are lowered, so that the content in the pressure-sensitive adhesive composition is 0.1 to 50.
It is preferably in the range of% by weight, more preferably 1-40.
% By weight.

If desired, a filler or the like may be added to the above-mentioned pressure-sensitive adhesive in order to impart further cohesive force. Light silicic acid anhydride or the like is preferably used as the filler.

The drug used in the present invention is not particularly limited as long as it can permeate the biological membrane transdermally.
Antipyretic analgesic and anti-inflammatory agent, steroidal anti-inflammatory agent, vasodilator,
Vasoconstrictor, antiarrhythmic agent, antihypertensive agent, antitussive expectorant, anti-neoplastic agent, general anesthetic, local anesthetic, hypnotic / analgesic agent,
Narcotics, stimulants / stimulants, psychiatric agents, autonomic agents,
Antiepileptics, antispasmodics, antispasmodics, hormones, antihistamines, anticoagulants, hemostatics, skeletal muscle relaxants, antiparkinson agents, respiratory stimulants, diuretics, choleretic agents, peptic ulcer treatments, urine Reproductive and anal agents, parasitic skin disease agents, emollients, vitamins, liver disease agents, addictive agents, gout remedies, diabetic agents, mineral agents, antibiotics, chemotherapeutic agents, etc. Can be mentioned. The specific examples are shown below.

Examples of the antipyretic analgesic and anti-inflammatory agent include acetaminophen, phenacetin, mefenamic acid, diclofenac sodium, flufenamic acid, aspirin, sodium salicylate, aminopyrine, alclofenac, ibuprofen, naproxen, flurpiprofen, ketoprofen, amphu. Enac sodium, mepyrizole, indomethacin, pentazocine, piroxicam and the like can be mentioned.

Examples of steroidal anti-inflammatory agents include:
Hydrocortisone, triamcinolone, dexamethasone, betamethasone, prednisolone and the like can be mentioned. Examples of the vasodilator include diltiazem hydrochloride, pentaerythritol tetranitrate, isosorbide nitrate, trazipyr, nicorandil, nitroglycerin, prenylamine lactate, molsidomine, amyl nitrite, tolazoline hydrochloride, and the like.As the vasoconstrictor, for example, Examples thereof include phenylephrine hydrochloride.

Examples of antiarrhythmic agents include procainamide hydrochloride, lidocaine hydrochloride, propranolol hydrochloride,
Examples thereof include alprenolol hydrochloride, atenolol, nadolol, metoprolol tartrate, adimarin, disopyramide, and mexiletine hydrochloride.

Examples of the antihypertensive agent include ecarazine hydrochloride, indapamide, clonidine hydrochloride, pnitrolol hydrochloride, labetalol hydrochloride, captopril, guanabenz acetate, meptamate, betaninidine sulfate and the like.

Examples of the antitussive expectorant include carbetapentane citrate, cloperastine, oxerazine tannate, cloptinol hydrochloride, clofedanol hydrochloride, noscapine hydrochloride, ephedrine hydrochloride, isoproterenol hydrochloride, chlorprenaline hydrochloride, methoxyphene hydrochloride. Examples include namin, procaterol hydrochloride, tulobuterol hydrochloride, clenbuterol hydrochloride, and ketotifen fumarate.

Examples of the anti-malignant tumor agents include cyclophosphamide, fluorouracil, degafur, mitomycin C, procarbazine hydrochloride, doxyfluridine,
Ranimustine and the like can be mentioned.

Examples of general anesthetics include thiopental sodium and pentobarbital sodium, and examples of local anesthetics include ethyl aminobenzoate, tetracaine hydrochloride, procaine hydrochloride, dipcaine hydrochloride, oxyprocaine hydrochloride, and hydrochloric acid. Examples of the hypnotic / analgesic include bromvalerylurea, amobarbital, and phenobarbital.

The narcotics include, for example, morphine hydrochloride, codeine phosphate, cocaine hydrochloride, pethidine hydrochloride, etc., and the stimulants / stimulants include, for example, methamphetamine hydrochloride etc., and the psychiatric agents include, for example, ,
Examples thereof include chlorpromazine hydrochloride, thioridazine, meprobamate, imipramine hydrochloride, chlordiazepoxide diazepam, and the like. Examples of agents for autonomic nerve include neostigmine bromide, bethanechol chloride and the like.

Examples of the antiepileptic agent include phenytoin sodium, etc., examples of the antispasmodic agent include methylatropine bromide, scopolamine, etc., and examples of the antispasmodic agent include difendole hydrochloride, betahistine mesylate and the like. Can be mentioned.

The hormonal agents include, for example, propylthiouracil, thiamazole, metenolone acetate, estradiol, estriol, progesterone, etc., and the antihistamines include, for example, diphenonehydramine hydrochloride, chlorpheniramine maleate, promethazine, Examples thereof include cyproheptadine hydrochloride and diphenylpyraline hydrochloride.

Examples of the blood coagulation inhibitor include warfarin potassium, ticlopidine hydrochloride and the like, and examples of the hemostatic agent include ethanesylate and the like.
Examples of the skeletal muscle relaxant include suxamethonium hydrochloride, eperisone hydrochloride and the like.

Examples of anti-Parkinson's agents include amantadine hydrochloride and the like. Examples of the respiratory stimulants include lobeline hydrochloride, dimorphoramine, naloxone hydrochloride and the like. Examples of the diuretic include hydroflumethiazide, isosorbide, furosemide and the like.

Examples of choleretic agents include ursodesoxycholic acid, osalmid and the like. Examples of the therapeutic agent for peptic ulcer include glycopyrronium bromide, proglumide, cetraxate hydrochloride, cimetidine, spizofron and the like. As urogenital and anal agents,
Examples include hexamine, sparteine, dinoprost, ritodrine hydrochloride and the like.

Examples of the agent for parasitic skin disease include salicylic acid, ciclopirox olamine, croconazole hydrochloride and the like. Examples of the emollient include urea and the like. Examples of the vitamin agent include calcitriol, thiamine hydrochloride, sodium riboflavin phosphate, pyridoxine hydrochloride, nicotinamide, panthenol, ascorbic acid and the like.

Examples of agents for liver diseases include tiopronin and the like. Examples of the drug for addiction include cinnamide and the like. As a therapeutic agent for gout,
For example, colchicine, probenecid, sulfinpyrazone and the like can be mentioned. Examples of the antidiabetic agent include, for example, tolptamide, chlorpropamide, glymidine sodium,
Glypsol, buformin hydrochloride, insulin and the like can be mentioned.

Examples of the inorganic preparations include calcium chloride, potassium iodide, sodium iodide and the like. Examples of the antibiotic include benzylpenicillin potassium, propicillin potassium, cloxacillin sodium, ampicillin sodium, bacampyricin hydrochloride,
Carbenicillin sodium, cephaloridine, cefoxitin sodium, erythromycin, chloramphenicol, tetracycline, kanamycin sulfate, cycloserine and the like can be mentioned. Examples of the chemotherapeutic agent include isoniaside, pyrazinamide, ethionamide and the like.

The content of the above-mentioned drug is appropriately determined depending on the kind of the drug and the purpose of use of the preparation. When the content is low, the drug efficacy is lowered, and when it is high, the tackiness is lowered and the drug is compatible with the adhesive. 0.01 to 5 in the pressure-sensitive adhesive composition because it becomes difficult
It is preferably 0% by weight. However, there is no particular problem even if the drug exists in the pressure-sensitive adhesive layer in a supersaturated state or in a state in which crystals are precipitated. Further, the drug may be encapsulated with an absorption enhancer, or a drug storage layer may be provided.

The support used in the patch of the invention is preferably one which is impermeable or hardly permeable to the drug and is flexible, and examples thereof include cellulose acetate, ethyl cellulose, polyethylene, polypropylene and polyvinyl chloride. ,
Vinyl acetate-vinyl chloride copolymer, ethylene-methyl acrylate copolymer, ethylene-vinyl acetate copolymer,
Ethylene-vinyl acetate-carbon monoxide copolymer, ethylene-butyl acrylate-carbon monoxide copolymer, polyvinylidene chloride, polyurethane, nylon, polyethylene terephthalate, resin films such as polybutylene terephthalate, aluminum sheet and the like, These may be a single-layer sheet or a laminated sheet, and may be laminated with a woven fabric or a non-woven fabric.

Further, for the purpose of enhancing the adhesiveness to the pressure-sensitive adhesive layer, surface treatment such as corona treatment or plasma discharge treatment may be performed, or anchor coating treatment may be performed with an anchor agent.

The thickness of the support is not particularly limited,
It is preferably 500 μm or less, more preferably 5 to 15
0 μm.

The thickness of the pressure-sensitive adhesive layer used in the patch of the present invention is not particularly limited, but if it becomes thin, the drug must be added at a high concentration, and as a result, the adhesive strength will decrease. When the thickness is increased, the drug present in the pressure-sensitive adhesive layer near the support is less likely to diffuse to the pressure-sensitive adhesive surface and the drug release property is lowered, so that the thickness is preferably 10 to 200 μm.

In the production of the patch of the present invention, a conventionally known method for producing an adhesive tape can be used. A typical example thereof is a solvent coating method, and other examples include a hot melt coating method and an emulsion coating method.

When the solvent coating is carried out, for example, a solution obtained by dissolving or dispersing a predetermined amount of a polymer containing a pressure-sensitive adhesive, a drug and a monoalkyl ester of maleic anhydride in a solvent such as ethyl acetate. A method of coating and drying on a support, a method of coating on a release paper and drying, and then transferring onto a support are preferably used.

Conventionally, a polymer containing maleic anhydride as a constituent, which has been used for improving the cohesive strength of a pressure-sensitive adhesive comprising a copolymer containing N-vinyl-2-pyrrolidone as a constituent, for example, the following formula The compound represented by [1] is hydrolyzed by contact with water such as evaporation of water or perspiration from the skin during application due to the presence of the anhydrous portion thereof to open the ring to form water-soluble maleic acid. Become.

The polymer having the ring-opened maleic acid as a constituent (the following formula [2]) has no effect of improving the cohesive force with respect to the pressure-sensitive adhesive, and the cohesive force is lowered. This is because the cohesive force applied to the maleic anhydride before hydrolysis is lost, and if a plasticizer or the like is added to the pressure-sensitive adhesive layer, the degree of decrease in the cohesive force is remarkable. This causes a problem in use, such as stickiness of the pressure-sensitive adhesive and adhesive residue on the skin when the patch is peeled off. In addition, it is necessary to be careful about humidity control when storing the patch,
Maintaining a stable cohesive force is difficult.

Polymers having a monoalkyl ester of maleic anhydride used as a component in the present invention, for example, the following formula [3] is generally prepared by reacting a maleic anhydride moiety of the following formula [1] with an alcohol. It is a ring-opened product, has a cohesive force imparting action, is water-insoluble, and the cohesive force does not decrease during application. This is because by opening the maleic anhydride portion in advance, it is possible to impart a stable cohesive force before and after application without changing to maleic acid due to water evaporation or perspiration from the skin during application. It is a thing. Further, since the monoalkyl ester of maleic anhydride itself is insoluble in water, even if a large amount is added to the pressure-sensitive adhesive layer, it does not become sticky due to water evaporation or perspiration from the skin during application.

[0064]

Embedded image

In the formula, X represents a copolymer portion. R is
Represents an alkyl group. n represents the number of repetitions.

The addition of a cross-linking agent, which is an important constituent of the present invention, increases the cohesive force by cross-linking a polymer having a monoalkyl ester of maleic anhydride as a constituent to increase the cohesive force. By the synergistic action with the imparting action, the cohesive force of the system can be greatly improved.

The present invention makes it possible to improve the cohesive strength of the pressure-sensitive adhesive layer and adjust the pressure-sensitive adhesive strength, and it is possible to provide a low-skin irritation patch having extremely good adhesiveness.

The present invention will be described in more detail with reference to the following examples, but the present invention is not limited to these examples.

Example 1 200 parts by weight of 2-ethylhexyl acrylate, 160 parts by weight of octyl acrylate, 40 parts by weight of N-vinyl-2-pyrrolidone and 400 parts by weight of ethyl acetate were added to a separable flask equipped with a stirrer and a reflux cooling device. The temperature was raised to 80 ° C. while stirring and purging with nitrogen. A solution prepared by dissolving 2 parts by weight of lauroyl peroxide in 100 parts by weight of cyclohexane was divided into 10 parts, and 1 was added to a separable flask to initiate polymerization. The remaining 9 was added at 1-hour intervals from the second hour after the start of the reaction, and after the addition was completed, the reaction was further continued for 2 hours. In order to adjust the viscosity, 50 parts by weight of ethyl acetate was added 5 times every 2 hours after the reaction was started. After completion of the reaction, the mixture was cooled, and then ethyl acetate was added to the mixture to obtain a solid content concentration of 3
An adhesive solution having 0% by weight and a viscosity of 4.3 × 10 4 cps was obtained (“adhesive solution A”).

To the resulting pressure-sensitive adhesive solution A, a monobutyl ester of methoxyethylene-maleic anhydride copolymer (G
ANTREZ ES-425, I.S. S. (Manufactured by Company P) was added so as to be 1 part by weight with respect to 100 parts by weight of the solid content of the pressure-sensitive adhesive solution A, and the whole solution was uniformly stirred by a rotor mill to obtain a mixed solution. The obtained mixed liquid was applied onto a siliconized polyethylene terephthalate film having a thickness of 35 μm so that the thickness of the adhesive layer after drying would be 80 μm, and dried in an oven at 60 ° C. for 30 minutes to obtain polyethylene terephthalate / ethylene- The pressure-sensitive adhesive layer was laminated on the polyethylene terephthalate layer of the vinyl acetate copolymer laminated film to obtain a tape sample of the pressure-sensitive adhesive composition.

Example 2 In Example 1, monobutyl ester of methoxyethylene-maleic anhydride copolymer (GANTREZ ES) was used.
-425, I.I. S. (Manufactured by Company P) is a solid content of the adhesive solution A 1
A tape sample of the pressure-sensitive adhesive composition was obtained in the same manner as in Example 1 except that 10 parts by weight was added to 00 parts by weight.

Example 3 In Example 1, the monoethyl ester of methoxyethylene-maleic anhydride copolymer (GANTREZ ES) was used.
-225, I.S. S. (Manufactured by Company P) is a solid content of the adhesive solution A 1
A tape sample of the pressure-sensitive adhesive composition was obtained in the same manner as in Example 1 except that 30 parts by weight was added to 00 parts by weight.

Example 4 302 parts by weight of 2-ethylhexyl acrylate, 98 parts by weight of N-vinyl-2-pyrrolidone and 400 parts of ethyl acetate
Part by weight was supplied to a separable flask equipped with a stirrer and a reflux cooling device, and the temperature was raised to 80 ° C. while stirring and purging with nitrogen. 2 parts by weight of lauroyl peroxide and 10 parts of cyclohexane
The solution dissolved in 0 parts by weight was divided into 10 parts, and 1 was added to a separable flask to start polymerization. The remaining 9 was added at 1-hour intervals from the second hour after the start of the reaction, and after the addition was completed, the reaction was further continued for 2 hours. To control the viscosity, 50 parts by weight of ethyl acetate was added every 2 hours after the reaction was started.
It was added twice. After completion of the reaction, the mixture was cooled, and ethyl acetate was added to the mixture to give a solid content of 35% by weight and a viscosity of 1.5 × 10 4 c.
A PSA adhesive solution was obtained ("Adhesive Solution B").

The resulting adhesive solution B was mixed with monoethyl ester of methoxyethylene-maleic anhydride copolymer (G
ANTREZ ES-225, I.D. S. (Manufactured by Company P) was added so as to be 5 parts by weight with respect to 100 parts by weight of the solid content of the adhesive solution B, and the whole liquid was uniformly stirred with a dissolver to obtain a mixed liquid. The obtained mixed liquid was applied onto a siliconized polyethylene terephthalate film having a thickness of 35 μm so that the thickness of the adhesive layer after drying would be 80 μm, and dried in an oven at 60 ° C. for 30 minutes to obtain polyethylene terephthalate / ethylene- The pressure-sensitive adhesive layer was laminated on the polyethylene terephthalate layer of the vinyl acetate copolymer laminated film to obtain a tape sample of the pressure-sensitive adhesive composition.

Example 5 240 parts by weight of 2-ethylhexyl acrylate, 160 parts by weight of N-vinyl-2-pyrrolidone and 40 parts of ethyl acetate
0 part by weight was supplied to a separable flask equipped with a stirrer and a reflux cooling device, and the temperature was raised to 80 ° C. while stirring and purging with nitrogen. 2 parts by weight of lauroyl peroxide to 1 part of cyclohexane
The solution dissolved in 00 parts by weight was divided into 10 parts, 1 of which was added to a separable flask to initiate polymerization. The remaining 9 was added at 1-hour intervals from the second hour after the start of the reaction, and after the addition was completed, the reaction was further continued for 2 hours. To control the viscosity, 50 parts by weight of ethyl acetate was added every 2 hours after the reaction was started.
It was added twice. After completion of the reaction, the mixture was cooled, and ethyl acetate was added to the mixture to give a solid content of 35% by weight and a viscosity of 2.9 × 10 4 c.
A ps adhesive solution was obtained ("Adhesive Solution C").

Separately, a methoxyethylene-maleic anhydride copolymer (G
ANTREZ AN-119, I.S. S. 50g)
Then, 450 g of ethanol (boiling point: 78 ° C.) and a slight amount of concentrated hydrochloric acid were added thereto, and the mixture was heated and stirred under reflux conditions for 8 hours to carry out ethyl esterification of the methoxyethylene-maleic anhydride copolymer. . The solvent of this solution was removed by drying to obtain a colorless and transparent monoethyl ester of a methoxyethylene-maleic anhydride copolymer (confirmed by IR). The above-mentioned monoethyl ester of methoxyethylene-maleic anhydride copolymer was added to the solid content 10 of the pressure-sensitive adhesive solution C.
20 parts by weight was added to 0 parts by weight, and the whole solution was uniformly stirred with a dissolver to obtain a mixed solution. The obtained mixed liquid was applied onto a siliconized polyethylene terephthalate film having a thickness of 35 μm so that the thickness of the adhesive layer after drying would be 80 μm, and dried in an oven at 60 ° C. for 30 minutes to obtain polyethylene terephthalate / ethylene- The pressure-sensitive adhesive layer was laminated on the polyethylene terephthalate layer of the vinyl acetate copolymer laminated film to obtain a tape sample of the pressure-sensitive adhesive composition.

Example 6 220 parts by weight of 2-ethylhexyl acrylate, 160 parts by weight of octyl acrylate, 20 parts by weight of N-vinyl-2-pyrrolidone and 400 parts by weight of ethyl acetate were added to a separable flask equipped with a stirrer and a reflux cooling device. The temperature was raised to 80 ° C. while stirring and purging with nitrogen. A solution prepared by dissolving 2 parts by weight of lauroyl peroxide in 100 parts by weight of cyclohexane was divided into 10 parts, and 1 was added to a separable flask to initiate polymerization. The remaining 9 was added at 1-hour intervals from the second hour after the start of the reaction, and after the addition was completed, the reaction was further continued for 2 hours. In order to adjust the viscosity, 50 parts by weight of ethyl acetate was added 5 times every 2 hours after the reaction was started. After completion of the reaction, the mixture was cooled, and then ethyl acetate was added to the mixture to obtain a solid content concentration of 3
An adhesive solution having 0% by weight and a viscosity of 3.2.times.10@4 cps was obtained ("Adhesive solution D").

Monoethyl ester of styrene-maleic anhydride copolymer was added to the obtained pressure-sensitive adhesive solution D in an amount of 100 parts by weight based on 100 parts by weight of the solid content of the pressure-sensitive adhesive solution D, and the whole liquid was added. Was uniformly stirred with a dissolver to obtain a mixed solution. The obtained mixed liquid was applied onto a siliconized polyethylene terephthalate film having a thickness of 35 μm so that the thickness of the adhesive layer after drying would be 80 μm,
It was dried in an oven at 60 ° C. for 30 minutes, and the above pressure-sensitive adhesive layer was laminated on the polyethylene terephthalate layer of the polyethylene terephthalate / ethylene-vinyl acetate copolymer laminated film to obtain a tape sample of the pressure-sensitive adhesive composition.

Example 7 In Example 1, monobutyl ester of methoxyethylene-maleic anhydride copolymer (GANTREZ ES) was used.
-425, I.I. S. (Manufactured by Company P) and isopropyl myristate as a plasticizer were added in an amount of 10 parts by weight and 30 parts by weight with respect to 70 parts by weight of the solid content of the adhesive solution A, respectively. A tape sample of the pressure-sensitive adhesive composition was obtained.

Example 8 In Example 1, monobutyl ester of methoxyethylene-maleic anhydride copolymer (GANTREZ ES
-425, I.I. S. (Manufactured by Company P) and diethyl sebacate as a plasticizer were added in an amount of 10 parts by weight and 20 parts by weight with respect to 70 parts by weight of the solid content of the adhesive solution A, respectively, in the same manner as in Example 1. A tape sample of the pressure-sensitive adhesive composition was obtained.

Example 9 In Example 4, monoethyl ester of methoxyethylene-maleic anhydride copolymer (GANTREZ ES) was used.
-225, I.S. S. P), polyethylene glycol as a plasticizer, and indomethacin as a drug were added to the adhesive solution B in an amount of 20 parts by weight, 20 parts by weight, and 0.5 parts by weight, respectively, with respect to 60 parts by weight of the solid content. A patch sample was obtained in the same manner as in Example 4.

Example 10 To the obtained pressure-sensitive adhesive solution A, a monoethyl ester of methoxyethylene-maleic anhydride copolymer (GANTREZ was added.
ES-225, I.S. S. (Manufactured by Company P) to 1 part by weight with respect to 100 parts by weight of the solid content of the adhesive solution A,
Further, ethyl acetate was added to adjust the solid content to 25% by weight, and the whole solution was uniformly stirred with a rotor mill. To this solution, trifunctional isocyanate (Coronate H
X, manufactured by Nippon Polyurethane Co., Ltd.) was added to the methoxyethylene-maleic anhydride copolymer monoethyl ester in an equivalent amount and stirred to obtain a mixed solution. The obtained mixed liquid was applied onto a siliconized polyethylene terephthalate film having a thickness of 35 μm so that the thickness of the adhesive layer after drying would be 80 μm, and the mixture was heated in an oven at 60 ° C. for 30 minutes.
After being dried for a minute, the pressure-sensitive adhesive layer was laminated on the polyethylene terephthalate layer of the polyethylene terephthalate / ethylene-vinyl acetate copolymer laminated film to obtain a tape sample of the pressure-sensitive adhesive composition.

Example 11 In Example 10, instead of the monoethyl ester of methoxyethylene-maleic anhydride copolymer, monobutyl ester of methoxyethylene-maleic anhydride copolymer (GANTREZ ES-425, IS) was used. Manufactured by P.)
A tape sample of the pressure-sensitive adhesive composition was obtained in the same manner as in Example 10 except that 1 part by weight was added to 100 parts by weight of the solid content of the pressure-sensitive adhesive solution A.

Example 12 The adhesive solution A thus obtained was mixed with a monoethyl ester of methoxyethylene-maleic anhydride copolymer (GANTREZ).
ES-225, I.S. S. (Manufactured by Company P) and isopropyl myristate to 30 parts by weight and 30 parts by weight of the solid content of the adhesive solution A at 70 parts by weight, respectively, and ethyl acetate is further added to obtain a solid content of 25% by weight. And the whole liquid was stirred by a rotor mill so as to be uniform. To this solution, trifunctional isocyanate (Coronate HX, manufactured by Nippon Polyurethane Industry Co., Ltd.) was added in an amount of 2 equivalents based on the monoethyl ester of methoxyethylene-maleic anhydride copolymer and stirred to obtain a mixed solution. It was The resulting mixed solution is siliconized to a thickness of 35μ.
m polyethylene terephthalate film so that the thickness of the adhesive layer after drying is 80 μm, and the temperature is 60 ° C.
Was dried in the oven for 30 minutes, and the pressure-sensitive adhesive layer was laminated on the polyethylene terephthalate layer of the polyethylene terephthalate / ethylene-vinyl acetate copolymer laminated film to obtain a tape sample of the pressure-sensitive adhesive composition.

Example 13 To the obtained pressure-sensitive adhesive solution A, a monobutyl ester of methoxyethylene-maleic anhydride copolymer (GANTREZ was added.
ES-425, I.S. S. (Manufactured by Company P) and diethyl sebacate are added so as to be 5 parts by weight and 20 parts by weight, respectively, with respect to 80 parts by weight of the solid content of the adhesive solution A, and ethyl acetate is further added so that the solid content is 25% by weight. And the whole liquid was stirred by a rotor mill so as to be uniform. To this solution, trifunctional isocyanate (Coronate HX, manufactured by Nippon Polyurethane Company) was added with methoxyethylene-
A mixed solution was obtained by adding 2 equivalents to the monobutyl ester of the maleic anhydride copolymer and stirring. The obtained mixed liquid was applied onto a siliconized polyethylene terephthalate film having a thickness of 35 μm so that the thickness of the adhesive layer after drying would be 80 μm, and dried in an oven at 60 ° C. for 30 minutes to obtain polyethylene terephthalate / ethylene- The pressure-sensitive adhesive layer was laminated on the polyethylene terephthalate layer of the vinyl acetate copolymer laminated film to obtain a tape sample of the pressure-sensitive adhesive composition.

Example 14 Into the obtained pressure-sensitive adhesive solution B, a monoethyl ester of methoxyethylene-maleic anhydride copolymer (GANTREZ was added.
ES-225, I.S. S. (Manufactured by Company P) and isopropyl myristate to the solid content of 80 parts by weight of the pressure-sensitive adhesive solution B at 10 parts by weight and 20 parts by weight, respectively, and ethyl acetate is further added to obtain a solid content of 25 parts by weight. %, And the whole liquid was stirred by a rotor mill so that it became uniform. To this solution, trifunctional isocyanate (Coronate HX, manufactured by Nippon Polyurethane Industry Co., Ltd.) was added in an amount of 2 equivalents based on the monoethyl ester of methoxyethylene-maleic anhydride copolymer and stirred to obtain a mixed solution. It was The resulting mixed solution is siliconized to a thickness of 35μ.
m polyethylene terephthalate film so that the thickness of the adhesive layer after drying is 80 μm, and the temperature is 60 ° C.
Was dried in the oven for 30 minutes, and the pressure-sensitive adhesive layer was laminated on the polyethylene terephthalate layer of the polyethylene terephthalate / ethylene-vinyl acetate copolymer laminated film to obtain a tape sample of the pressure-sensitive adhesive composition.

Example 15 In Example 12, the monoethyl ester of methoxyethylene-maleic anhydride copolymer (GANTREZ E) was used.
S-225, I.S. S. P) and isopropyl myristate to 30 parts by weight and 30 parts by weight, respectively, with respect to 70 parts by weight of the solid content of the adhesive solution A,
The whole liquid was stirred by a rotor mill so as to be uniform.
Example 12 was repeated except that aluminum tris (acetylacetonate) was added to this solution instead of the trifunctional isocyanate in an amount equivalent to the monoethyl ester of the methoxyethylene-maleic anhydride copolymer.
A tape sample of the pressure-sensitive adhesive composition was obtained in the same manner as in.

Example 16 To the obtained pressure-sensitive adhesive solution A, monobutyl ester of methoxyethylene-maleic anhydride copolymer (GANTREZ was added.
ES-425, I.S. S. (Manufactured by Company P), isopropyl myristate, and indomethacin to 70 parts by weight of the solid content of the adhesive solution A at 2 parts by weight, 30 parts by weight, and 0.5 parts by weight, respectively, and acetic acid. Ethyl was added to adjust the solid content to be 25% by weight, and the whole liquid was stirred with a rotor mill so as to be uniform. To this solution, trifunctional isocyanate (Coronate HX, manufactured by Nippon Polyurethane Company) was added in an amount of 2 equivalents relative to the monobutyl ester of the methoxyethylene-maleic anhydride copolymer and stirred to obtain a mixed solution. It was The thickness of the adhesive layer after drying was 80 on a polyethylene terephthalate film having a thickness of 35 μm obtained by siliconizing the obtained mixed liquid.
It was applied so as to have a thickness of μm, dried in an oven at 60 ° C. for 30 minutes, and the adhesive layer was laminated on the polyethylene terephthalate layer of the polyethylene terephthalate / ethylene-vinyl acetate copolymer laminated film to obtain a patch sample. .

Comparative Example 1 Without adding anything to the obtained pressure-sensitive adhesive solution A, it was applied on a siliconized polyethylene terephthalate film having a thickness of 35 μm so that the thickness of the pressure-sensitive adhesive layer after drying would be 80 μm. It was dried in an oven at 60 ° C. for 30 minutes, and the above pressure-sensitive adhesive layer was laminated on the polyethylene terephthalate layer of the polyethylene terephthalate / ethylene-vinyl acetate copolymer laminated film to obtain a preparation sample.

Comparative Example 2 Without adding anything to the obtained pressure-sensitive adhesive solution B, the pressure-sensitive adhesive layer after drying was coated on a siliconized polyethylene terephthalate film having a thickness of 35 μm to a thickness of 80 μm, It was dried in an oven at 60 ° C. for 30 minutes, and the above pressure-sensitive adhesive layer was laminated on the polyethylene terephthalate layer of the polyethylene terephthalate / ethylene-vinyl acetate copolymer laminated film to obtain a preparation sample.

Comparative Example 3 In Example 7, instead of isopropyl myristate and the monobutyl ester of a methoxyethylene-maleic anhydride copolymer, a methoxyethylene-maleic anhydride copolymer (GANTREZ S-95, I.S. (Manufactured by P. Co., Ltd.) was added in the same manner as in Example 7 except that 30 parts by weight and 10 parts by weight were added to 70 parts by weight of the solid content of the adhesive solution A, respectively. Got

Comparative Example 4 In Example 7, isopropyl myristate alone was added to 70 parts by weight of the solid content of the adhesive solution A without adding the monobutyl ester of the methoxyethylene-maleic anhydride copolymer. Example 7 except that 30 parts by weight was added
A tape sample of the pressure-sensitive adhesive composition was obtained in the same manner as in.

Comparative Example 5 In Example 8, diethyl sebacate alone was added to 70 parts by weight of the solid content of the adhesive solution A without adding the monobutyl ester of the methoxyethylene-maleic anhydride copolymer. A tape sample of the pressure-sensitive adhesive composition was obtained in the same manner as in Example 8 except that 20 parts by weight was added.

Comparative Example 6 In Example 9, only polyethylene glycol and indomethacin were added to 60 parts by weight of the solid content of the adhesive solution B without adding the monoethyl ester of methoxyethylene-maleic anhydride copolymer. A tape sample of the pressure-sensitive adhesive composition was obtained in the same manner as in Example 9 except that 20 parts by weight and 0.5 parts by weight, respectively, were added.

Comparative Example 7 In Example 7, instead of isopropyl myristate and the monobutyl ester of methoxyethylene-maleic anhydride copolymer, methoxyethylene-maleic anhydride copolymer (GANTREZ AN-119, I.S. .P
Manufactured by the company) to 70 parts by weight of the solid content of the adhesive solution A,
Tape samples of the pressure-sensitive adhesive composition were obtained in the same manner as in Example 7, except that 30 parts by weight and 1 part by weight, respectively, were added.

Evaluation 1 Regarding the tape samples and the formulation samples of the pressure-sensitive adhesive compositions obtained in Examples 1 to 16 and Comparative Examples 1 to 7, JIS
The holding power was measured according to Z 0237-1980. The results are shown in Table 1.

[0096]

[Table 1]

By using the specific copolymer in combination with the polymer having a monoalkyl ester of maleic anhydride as a constituent, the cohesive force was remarkably improved as compared with the case where it was not used in combination. Also, the addition of a plasticizer reduces the cohesive force, but the addition of a polymer having a maleic anhydride monoalkyl ester as a constituent component improves the cohesive force, and the addition of a crosslinking agent further improves the cohesive force. I found out that

Evaluation 2 Regarding the tape samples, patch samples and formulation samples of the pressure-sensitive adhesive compositions obtained in Examples 1, 7, 9, 10, 16 and Comparative Examples 4, 6 and 7, the upper arms of five adult males were used. The adhesive strength was evaluated by the following 3 grades based on the degree of adhesive residue on the skin due to insufficient cohesive strength when peeled after 0.5 hour and 24 hours. ○: No adhesive residue on all people △: Adhesive residue on 1 to 4 people ×: Adhesive residue on all people

Further, the irritative property was peeled off after 24 hours and 30
The state of the skin after the observation was visually observed and evaluated according to the following evaluation criteria, and the average value of the scores of 5 persons was used as an index. 0: No erythema 1: Very slight erythema barely discernible 2: Clear erythema 3: Moderate erythema 4: Strong deep red erythema The results are shown in Table 2.

[0100]

[Table 2]

Furthermore, when the patches of Examples 9 and 16 were applied to the lumbar region of five adult males having lower back pain, the symptoms were improved after 2 to 4 hours.

In order to show the water resistance and humidity resistance of the polymer having a monoalkyl ester of maleic anhydride as a constituent, the samples of Example 7 and Comparative Example 7 were used, and the samples were treated at 40 ° C. and 75%.
Humidification was performed for 1 week under the condition of RH. The holding power of this sample at the initial stage and after humidification was measured to evaluate water resistance and moisture resistance. The results are shown in Table 3.

[0103]

[Table 3]

[0104]

EFFECTS OF THE INVENTION Since the pressure-sensitive adhesive composition of the present invention and the patch using the same have the above-mentioned constitution, a specific copolymer containing a specific monoalkyl ester of maleic anhydride as a constituent component is used. By using in combination, and further by adding a crosslinking agent as necessary, crosslinking can be performed without causing stickiness of the adhesive or adhesive residue on the skin during peeling.

Further, by using a polymer having a monoalkyl ester of maleic anhydride as a constituent component, which has an excellent water resistance and an effect of imparting an excellent cohesive force, the cohesive force is effectively increased. As a result, it has good adhesive strength, low skin irritation, and well-balanced adhesiveness. The pressure-sensitive adhesive composition of the present invention and the patch using the same can be used not only to enhance cohesive force, but also to adjust pressure-sensitive adhesive force such as making too strong pressure-sensitive adhesive force appropriate. it can.

Further, since the pressure-sensitive adhesive composition of the present invention and the patch using the same can stably enhance the cohesive force, a large amount of a drug absorption promoter is added or the pressure-sensitive adhesive layer is plasticized to make the drug adhesive. It is possible to add a large amount of a plasticizer for enhancing the diffusion of the additives in the pressure-sensitive adhesive layer, and as a result, it is possible to provide a patch having excellent drug release properties. Addition of a cross-linking agent to the pressure-sensitive adhesive composition of the present invention and a patch using the same, particularly, a polymer having a monoalkyl ester of maleic anhydride as a constituent component causes a decrease in cohesive force due to addition of a large amount of a plasticizer or the like. It is extremely useful when sufficient cohesive force cannot be obtained only by the effect of imparting cohesive force.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification number Internal reference number FI Technical display location C09J 135/02 JDE C09J 135/02 JDE // A61K 9/70 333 A61K 9/70 333 334 334 A61L 15/58 A61L 15/06

Claims (4)

[Claims] 1. A pressure-sensitive adhesive composition comprising a water-insoluble copolymer containing N-vinyl-2-pyrrolidone as a constituent and a polymer containing a monoalkyl ester of maleic anhydride as a constituent. 2. A pressure-sensitive adhesive composition comprising the pressure-sensitive adhesive composition according to claim 1 containing a crosslinking agent. 3. A pressure-sensitive adhesive composition comprising the pressure-sensitive adhesive composition according to claim 1 or 2 containing a plasticizer. 4. An adhesive patch, comprising a support and a pressure-sensitive adhesive layer comprising the pressure-sensitive adhesive composition according to claim 1 and a drug laminated on one surface of the support.