JP5036035B2 - Keratin peeling adhesive composition and keratin peeling adhesive sheet - Google Patents

Description

  The present invention relates to an exfoliating pressure-sensitive adhesive sheet that can exfoliate the stratum corneum by sticking / peeling to the skin, and a horny exfoliating pressure-sensitive adhesive composition that can be used for the adhesive layer of the exfoliating pressure-sensitive adhesive sheet. is there.

  In recent years, attention to chemical peeling has increased greatly due to its immediate effect and effectiveness. Chemical peeling means that the skin external preparation (α-hydroquinone, glycolic acid, lactic acid, phenol, etc.) containing an organic acid having a specific structure is applied to the stratum corneum on the skin surface, thereby causing keratin due to chemical corrosion. A type of cosmetic method that exfoliates layers and enhances skin metabolism. By using this chemical peeling, improvement of symptoms such as skin spots, dark spots, dullness, acne, acne scars and fine lines can be expected.

  Therefore, an external preparation for skin containing an organic acid and a nonionic water-soluble polymer and having a pH of 2.0 or less has been proposed (Patent Document 1).

In addition, a cosmetic tape having an adhesive layer containing a chemical peeling agent has been proposed (Patent Document 2).
Table 2004/004675 Japanese Patent No. 3515303

  However, the skin external preparation containing an organic acid as disclosed in Patent Document 1 has a depth at which the liquid skin external preparation corrodes the skin after being applied to the skin and acting until it is washed away. It is extremely difficult to control and may cause skin damage such as burns. There is also a problem that the drug spreads not only to the treatment site but also to the surrounding healthy part.

  Further, in the case of the cosmetic tape disclosed in Patent Document 2, it takes a long time for the action compared to the liquid medicine, and there is a risk that skin damage may occur along with it, and if it is not washed away completely after use. Therefore, it is not easy and safe.

  The present invention has been made in view of such a situation, and an object thereof is to provide an adhesive sheet for exfoliation that can be used safely and easily, and an adhesive composition for exfoliation used for the exfoliation. To do.

In order to achieve the above object, first, the present invention includes a (meth) acrylic polymer (a) containing at least a (meth) acrylic polymer (a1) having a carboxyl group as a crosslinkable functional group , and a number average (Meth) acrylic oligomer (b) having a lactam ring having a molecular weight (Mn) of 4,000 to 10,000, a crosslinking agent (c), and a liquid component (d) having a number average molecular weight (Mn) of less than 4,000 And the (meth) acrylic polymer (a) does not have a crosslinkable functional group having a number average molecular weight (Mn) of 300,000 to 1,500,000 (a2) further comprises, the crosslinking agent provides a desquamating pressure-sensitive adhesive composition characterized Rukoto der isocyanate crosslinking agent (invention 1).

In the adhesive composition for exfoliating stratum corneum according to the invention ( invention 1), a suitable stratum corneum peeling force is obtained by using the (meth) acrylic oligomer (b) having a lactam ring and the liquid component (d). It becomes possible. Therefore, the pressure-sensitive adhesive layer formed using the above-mentioned pressure-sensitive adhesive composition for exfoliating has an adhesive force excellent for exfoliating the stratum corneum from the skin, and can exfoliate the stratum corneum uniformly. .

Further, in the pressure-sensitive adhesive composition for exfoliation according to the invention ( Invention 1), the liquid component (d) having a number average molecular weight (Mn) of less than 4,000 is used, but the liquid component penetrates into the stratum corneum. In order to swell and soften the stratum corneum, pain when peeling the stratum corneum from the skin can be reduced.

In the said invention ( invention 1), it is preferable that the said liquid component (d) has as a main component the component whose vapor pressure in 20 degreeC is less than 10 Pa ( invention 2).

Moreover, in the said invention ( invention 1), it is preferable that the said liquid component (d) is a polyhydric alcohol ( invention 3).

In the above inventions ( Inventions 1 to 3), the (meth) acrylic oligomer (b) having a lactam ring is preferably a copolymer of a vinyl monomer having a lactam ring and an alkyl (meth) acrylate. ( Invention 4).

In the above invention ( Invention 4), the vinyl monomer having a lactam ring is preferably N-vinyl-2-pyrrolidone ( Invention 5).

In the said invention ( invention 4 and 5), it is preferable that the compounding quantity of the vinyl monomer which has the said lactam ring in the (meth) acrylic-type oligomer (b) which has the said lactam ring is 5-45 mol% ( invention 6). ).

In the above inventions ( Inventions 1 to 6 ), the number average molecular weight (Mn) of the (meth) acrylic polymer (a1) having a crosslinkable functional group is preferably 300,000 to 1,500,000. ( Invention 7 ).
In the said invention ( invention 1-7 ), the compounding quantity of the (meth) acrylic-type oligomer (b) which has the said lactam ring is 50-700 mass with respect to 100 mass parts of said (meth) acrylic-type polymers (a). Part ( Invention 8 ).
In the said invention ( invention 1-8 ), the addition amount of the said crosslinking agent (c) is 0.01-15 mass with respect to 100 mass parts of (meth) acrylic-type polymers (a1) which have the said crosslinkable functional group. Part ( Invention 9 ).
In the said invention ( invention 1-9 ), it is preferable that the compounding quantity of the said liquid component (d) is 2.5-40 mass% in the adhesive composition for keratin peeling ( invention 10 ).

2ndly, this invention provided the support body and the adhesive layer formed using the said adhesive composition for exfoliation ( Invention 1-10 ) laminated | stacked on the said support body. Provided is a pressure-sensitive adhesive sheet for exfoliating keratin ( Invention 11 ). In the present specification, the “sheet” includes a tape-like one.

According to the pressure-sensitive adhesive sheet for exfoliating according to the above invention ( Invention 11 ), the stratum corneum can be easily peeled off by repeating the pasting and peeling for a short time about 1 to 3 times, and the adhered stratum corneum. The layers can be peeled uniformly. Moreover, the pain at the time of peeling can be reduced, and also the safety to the skin is high.

  The pressure-sensitive adhesive layer formed using the pressure-sensitive adhesive composition for exfoliation of the present invention has an excellent adhesive force for exfoliating the stratum corneum from the skin, and can exfoliate the stratum corneum uniformly. . Moreover, the pain at the time of peeling off the stratum corneum from the skin can be reduced, and the safety to the skin is also high.

  In addition, according to the pressure-sensitive adhesive sheet for exfoliation of the present invention, the stratum corneum can be easily removed by repeating the pasting and peeling for a short time about 1 to 3 times, and the applied stratum corneum is uniform. Can be peeled off. Moreover, the pain at the time of peeling off the stratum corneum from the skin can be reduced, and the safety to the skin is also high.

Hereinafter, embodiments of the present invention will be described.
[Adhesive composition for exfoliation]
The pressure-sensitive adhesive composition for exfoliation according to this embodiment includes a (meth) acrylic polymer (a), a (meth) acrylic oligomer (b) having a lactam ring, a crosslinking agent (c), a liquid component ( d).

(A) (Meth) acrylic polymer (Meth) acrylic polymer (a) includes at least a crosslinkable functional group (meth) acrylic polymer (a1) and has a crosslinkable functional group (meth) Both the acrylic polymer (a1) and the (meth) acrylic polymer (a2) having no crosslinkable functional group may be included.

  The (meth) acrylic polymer (a1) having a crosslinkable functional group is preferably a copolymer of a vinyl monomer having a crosslinkable functional group and a (meth) acrylic acid alkyl ester. The (meth) acrylic polymer (a2) having no crosslinkable functional group is a homopolymer of (meth) acrylic acid alkyl ester or a copolymer of a vinyl monomer and (meth) acrylic acid alkyl ester. In particular, it is preferably a copolymer of a vinyl monomer and an alkyl (meth) acrylate, and the vinyl monomer preferably has a lactam ring.

  As the (meth) acrylic acid alkyl ester, those having 1 to 14 carbon atoms in the alkyl group are preferable. For example, methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, (meth) Isopropyl acrylate, 2-methoxyethyl (meth) acrylate, butyl (meth) acrylate, isobutyl (meth) acrylate, pentyl (meth) acrylate, hexyl (meth) acrylate, octyl (meth) acrylate, ( Examples include isooctyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, nonyl (meth) acrylate, isononyl (meth) acrylate, lauryl (meth) acrylate, and the like. Can be used in combination.

  Examples of the crosslinkable functional group of the vinyl monomer having a crosslinkable functional group include a carboxyl group and a hydroxyl group. Examples of the vinyl monomer having a crosslinkable functional group include (meth) acrylic acid having a carboxyl group, 2-hydroxyethyl (meth) acrylate having a hydroxyl group, 4-hydroxybutyl (meth) acrylate, and the like. 1 type can be used individually or in combination of 2 or more types.

  The blending amount of the vinyl monomer having a crosslinkable functional group in the (meth) acrylic polymer (a1) having a crosslinkable functional group is preferably 2 to 35 mol%. When the blending amount of the vinyl monomer having a crosslinkable functional group is less than 2 mol%, crosslinking is insufficient, and when it exceeds 35 mol%, a sufficient exfoliating effect may not be obtained.

  As the vinyl monomer having a lactam ring, N-vinyl-2-pyrrolidone, N-vinyl-2-piperidone, N-vinyl-ε-caprolactam and the like are preferable. Pyrrolidone is preferred.

  It is preferable that the compounding quantity of the vinyl monomer which has a lactam ring in the (meth) acrylic-type polymer (a2) which does not have a crosslinkable functional group shall be 1-40 mol%.

  Number average of (meth) acrylic polymer (a) (each of (meth) acrylic polymer (a1) having a crosslinkable functional group and (meth) acrylic polymer (a2) having no crosslinkable functional group) The molecular weight (Mn) is preferably 300,000 to 1,500,000, particularly preferably 350,000 to 1,200,000, and more preferably 400,000 to 1,000,000. Is preferred. In addition, the number average molecular weight (Mn) in this specification is measured by a gel permeation chromatography (GPC analysis) method, and is a value converted with standard polystyrene.

  When the number average molecular weight (Mn) of the (meth) acrylic polymer (a) is less than 300,000, the cohesive force of the resulting pressure-sensitive adhesive may be insufficient, and adhesive residue may be generated, and the (meth) acrylic polymer ( When the number average molecular weight (Mn) of a) exceeds 1,500,000, the viscosity becomes high, so that uniform mixing with other components becomes difficult, and there is a possibility that a stable pressure-sensitive adhesive cannot be obtained.

  The (meth) acrylic polymer (a) includes both a (meth) acrylic polymer (a1) having a crosslinkable functional group and a (meth) acrylic polymer (a2) having no crosslinkable functional group. In this case, the blending amount of the (meth) acrylic polymer (a2) having no crosslinkable functional group is 50 to 100 parts by mass of the (meth) acrylic polymer (a1) having a crosslinkable functional group. The amount is preferably 400 parts by mass, and particularly preferably 100 to 300 parts by mass.

(B) (Meth) acrylic oligomer having a lactam ring The (meth) acrylic oligomer (b) having a lactam ring is a copolymer of a vinyl monomer having a lactam ring and an alkyl (meth) acrylate. Is preferred.

  As the vinyl monomer having a lactam ring, N-vinyl-2-pyrrolidone, N-vinyl-2-piperidone, N-vinyl-ε-caprolactam and the like are preferable. Pyrrolidone is preferred.

  The blending amount of the vinyl monomer having a lactam ring in the (meth) acrylic oligomer (b) having a lactam ring is preferably 5 to 45 mol%, particularly preferably 10 to 40 mol%. When the blending amount of the vinyl monomer having a lactam ring is less than 5 mol%, the wettability to the skin is insufficient, and the skin adhesion and thus the stratum corneum peeling force may be lowered. On the other hand, when the compounding quantity of the vinyl monomer which has a lactam ring exceeds 45 mol%, the obtained adhesive will gelatinize and there exists a possibility that manufacture or handling of the adhesive sheet for exfoliation may become difficult.

  As the (meth) acrylic acid alkyl ester, those having 2 to 14 carbon atoms of the alkyl group are preferable. For example, ethyl (meth) acrylate, propyl (meth) acrylate, isopropyl (meth) acrylate, (meth) 2-methoxyethyl acrylate, butyl (meth) acrylate, isobutyl (meth) acrylate, pentyl (meth) acrylate, hexyl (meth) acrylate, octyl (meth) acrylate, isooctyl (meth) acrylate, ( Examples include 2-ethylhexyl (meth) acrylate, nonyl (meth) acrylate, isononyl (meth) acrylate, lauryl (meth) acrylate, and the like, and these can be used alone or in combination of two or more. .

  A preferable combination of a vinyl monomer having a lactam ring and an alkyl (meth) acrylate is a combination of N-vinyl-2-pyrrolidone and 2-ethylhexyl (meth) acrylate.

  The number average molecular weight (Mn) of the (meth) acrylic oligomer (b) having a lactam ring is preferably 4,000 to 10,000, and particularly preferably 5,000 to 9,000. When the number average molecular weight (Mn) is less than 4,000, the composition may be excessively plasticized and the exfoliation performance may be deteriorated. When the number average molecular weight (Mn) exceeds 10,000, the lactam The viscosity of the (meth) acrylic oligomer (b) having a ring is excessively increased, making it difficult to mix uniformly with the (meth) acrylic polymer (a), and the wettability to the skin is reduced. There is a case.

  In the horny exfoliation pressure-sensitive adhesive composition according to this embodiment, by using the (meth) acrylic oligomer (b) having the lactam ring, the wettability to the skin can be improved and the skin adhesion can be improved. This makes it possible to obtain a suitable stratum corneum peeling force. Further, the (meth) acrylic oligomer (b) having a lactam ring has high compatibility with the (meth) acrylic polymer (a), and even when an additive is added to the adhesive composition, Easy to disperse components.

  The blending amount of the (meth) acrylic oligomer (b) having a lactam ring is preferably 50 to 700 parts by mass, particularly 80 to 500 parts by mass with respect to 100 parts by mass of the (meth) acrylic polymer (a). Part. If the blending amount of the (meth) acrylic oligomer (b) having a lactam ring is less than 50 parts by mass, the wettability of the adhesive to the skin may be significantly reduced, and the necessary adhesive strength may not be obtained. When the blending amount of the (meth) acrylic oligomer (b) having a lactam ring exceeds 700 parts by mass, the cohesive strength of the pressure-sensitive adhesive is excessively reduced, and adhesive residue is generated on the skin, or the necessary pressure-sensitive adhesive strength is obtained. There is a risk of not being able to.

(C) Crosslinking agent As the crosslinking agent (c), a polyfunctional compound having reactivity with the crosslinkable functional group of the (meth) acrylic polymer (a1) having a crosslinkable functional group can be used. . Examples of the polyfunctional compound include an isocyanate compound, an epoxy compound, an aziridine compound, a metal chelate compound, and the like, among which an isocyanate compound is preferable.

  Examples of the isocyanate compound include aliphatic isocyanates such as hexamethylene diisocyanate, aromatic isocyanates such as tolylene diisocyanate, diphenylmethane diisocyanate and xylylene diisocyanate, alicyclic isocyanates such as isophorone diisocyanate and hydrogenated diphenylmethane diisocyanate, and the like. Adducts obtained by reacting an isocyanate compound with a polyol such as glycerol or trimethylolpropane can be used, and one kind can be used alone, or two or more kinds can be used in combination.

  It is preferable that the addition amount of a crosslinking agent (c) is 0.01-15 mass parts with respect to 100 mass parts of (meth) acrylic-type polymer (a1) which has a functional group which can be bridge | crosslinked, especially 0.1-0.1 mass parts. It is preferably 5 parts by mass. When the addition amount of the crosslinking agent (c) is less than 0.01 parts by mass, it cannot be sufficiently crosslinked, and when the addition amount of the crosslinking agent (c) exceeds 15 parts by mass, the crosslinking density of the pressure-sensitive adhesive is excessive. In some cases, the wettability of the adhesive to the skin may be significantly reduced.

(D) Liquid component The liquid component (d) penetrates into the keratin and swells and softens the keratin. This can reduce pain when the stratum corneum is peeled from the skin. In order to ensure the permeability to the keratin, the number average molecular weight (Mn) of the liquid component (d) needs to be less than 4,000, and preferably 90 to 3,000.

  The pH of the liquid component (d) is preferably 6-8. If the pH is out of this range, the skin may be corroded, for example, like an organic acid, and the safety to the skin is lowered.

  The liquid component (d) is preferably one that does not volatilize at room temperature and normal pressure, and therefore the vapor pressure at 20 ° C. is preferably less than 1000 Pa, particularly preferably less than 10 Pa. If the liquid component (d) is volatile, measures such as sealing the exfoliating pressure-sensitive adhesive sheet so that the liquid component (d) does not volatilize from the adhesive layer during storage of the exfoliating pressure-sensitive adhesive sheet, etc. Is required.

Examples of the liquid component (d) as described above include glycerin, diglycerin, triglycerin, tetraglycerin, ethylene glycol, 1,3-butylene glycol, 1,3-propanediol, 1,4-butylene glycol, and propylene. Polyhydric alcohols such as glycol, dipropylene glycol, polyethylene glycol, polypropylene glycol; fatty acids such as capric acid, lauric acid, myristic acid, pentadecylic acid, palmitic acid, stearic acid, linoleic acid, linolenic acid; olive oil, camellia oil, castor oil Fatty oils such as safflower oil, corn oil; methyl caprate, methyl caproate, methyl laurate, methyl myristate, methyl stearate, isopropyl palmitate, lauric acid, isopropyl, isooctyl palmitate , Fatty acid esters such as isooctyl stearate, diethyl sebacate, etc .; hydrocarbon oils such as liquid paraffin, squalene, squalane; liquid surfactants, etc., which may be used alone or in combination of two or more Can do. Among these, it is preferable to use polyhydric alcohols such as glycerin , polyethylene glycol, and polypropylene glycol, which are particularly excellent in moisture retention and safety.

  The blending amount of the liquid component (d) is preferably 2.5 to 40% by mass, and particularly preferably 5 to 30% by mass in the keratin peeling adhesive composition. When the blending amount of the liquid component (d) is less than 2.5% by mass, the effect of the liquid component (d) is low, and pain may occur when exfoliating the keratin, and the blending amount of the liquid component (d) If it exceeds 40% by mass, the cohesive force of the pressure-sensitive adhesive is lowered, and there is a possibility that adhesive residue may be generated.

(E) Third component The pressure-sensitive adhesive composition for exfoliation according to the present embodiment may contain a third component (e) other than the components (a) to (d). As such third component (e), various agents such as drugs, antioxidants, viscosity modifiers, ultraviolet absorbers, masking agents, plasticizers, waxes, colorants, inorganic fillers, organic fillers, extenders, coupling agents, etc. An additive etc. are mentioned, 1 type can be used individually or in combination of 2 or more types.

  The pressure-sensitive adhesive composition for exfoliation according to this embodiment containing the components described above can be produced by a conventional method, and each component may be appropriately mixed.

  The pressure-sensitive adhesive layer formed using the pressure-sensitive adhesive composition for exfoliating skin according to the present embodiment has sufficient adhesive strength to exfoliate the stratum corneum from the skin, and can uniformly exfoliate the stratum corneum. It is.

  In accordance with JIS Z0237 after 5 minutes, a pressure-sensitive adhesive sheet using the pressure-sensitive adhesive composition for exfoliating skin according to the present embodiment was formed by attaching a pressure-sensitive adhesive sheet formed on a polyethylene terephthalate film having a thickness of 40 μm to a bakelite. The adhesive strength (mode: 180 ° peeling, peeling speed: 300 mm / min, sticking time: 5 minutes) is preferably 2 to 20 N / 25 mm, particularly preferably 3 to 12 N / 25 mm. If the adhesive force is less than 2 N / 25 mm, the stratum corneum cannot be effectively peeled off. On the other hand, if the adhesive strength exceeds 20 N / 25 mm, pain may occur when peeling from the skin, and adhesive residue may occur on the skin.

  In the present invention, the pressure-sensitive adhesive sheet formed by forming a pressure-sensitive adhesive layer using a pressure-sensitive adhesive composition on a polyethylene terephthalate film having a thickness of 50 μm and a thickness of 40 μm was measured, and the measured value was used as a reference. Even if the thickness of the body / pressure-sensitive adhesive layer is a pressure-sensitive adhesive composition or pressure-sensitive adhesive sheet other than those described above, the evaluation can be performed based on the results measured by the above measurement method.

[Adhesive sheet for exfoliation]
The pressure-sensitive adhesive sheet for exfoliation according to this embodiment includes a support and a pressure-sensitive adhesive layer laminated on one side of the support. A separate release material may be laminated on the exposed surface of the pressure-sensitive adhesive layer.

  The pressure-sensitive adhesive layer is a layer formed by applying and forming the above-mentioned pressure-sensitive adhesive composition for exfoliation to a support. For example, a pressure-sensitive adhesive composition for exfoliation dissolved in an organic solvent such as toluene, ethyl acetate, methyl ethyl ketone, and acetone is applied to a support by a conventional method and then dried (a crosslinkable composition is crosslinked). Thus, a pressure-sensitive adhesive layer can be formed.

  As a method for applying the adhesive composition for exfoliating exfoliation, an existing coating apparatus can be used, and examples thereof include a gravure coater, a Mayer bar coater, a comma coater, a roll coater, a knife coater, a die coater, and a screen coater. However, it is not limited to these.

  The thickness of the pressure-sensitive adhesive layer is preferably 5 to 300 μm and particularly preferably 10 to 200 μm in order to effectively peel the stratum corneum.

  The material of the support may be appropriately selected in consideration of the ease of use of the exfoliating pressure-sensitive adhesive sheet. For example, a polyester film such as polyethylene terephthalate, polyethylene, polypropylene, ethylene / methacrylic acid copolymer, ethylene / Resin films such as polyolefin-based films such as methyl methacrylate, polyurethane-based films, polystyrene-based thermoplastic elastomer films; woven fabrics, knitted fabrics, nonwoven fabrics made of various synthetic fibers and / or natural fibers; fine paper, glassine paper, Paper such as coated paper; laminates thereof can be used.

  The surface on the pressure-sensitive adhesive layer side of the support may be subjected to surface treatment such as primer treatment, corona treatment, plasma treatment, etc. in order to enhance the adhesion to the pressure-sensitive adhesive layer, In the case of forming a wound body, the surface of the support may be stripped with a silicone release agent, a long-chain alkyl compound, or the like.

  The thickness of the support is usually 5 to 250 μm, preferably about 10 to 100 μm when the film is used as the support, and 10 to 1000 μm when the support is made of woven fabric, nonwoven fabric, paper, or the like, preferably Is about 20 to 500 μm.

  When laminating a release material on the adhesive layer, the release material can be fine paper, glassine paper, coated paper, polyethylene laminated paper, polypropylene laminated paper, etc .; polyester film such as polyethylene terephthalate, polyolefin such as polyethylene, polypropylene, etc. A material such as a synthetic resin film such as a base film can be used, and if necessary, one side or both sides of the material may be subjected to a peeling treatment.

  According to the exfoliated pressure-sensitive adhesive sheet according to the present embodiment, the stratum corneum can be easily peeled by repeating the application and peeling for a short time (for example, 3 to 5 minutes) to the skin about 1 to 3 times. In addition, the stratum corneum at the applied portion can be peeled uniformly. Moreover, there is almost no pain when peeling the stratum corneum from the skin, and the safety to the skin is also high.

  EXAMPLES Hereinafter, although an Example etc. demonstrate this invention further more concretely, the scope of the present invention is not limited to these Examples etc.

[Example 1]
Acrylic polymer having a crosslinkable functional group (carboxyl group) (2-ethylhexyl acrylate / acrylic acid copolymer: 82/18 mol%, number average molecular weight: about 850,000, solid content: 50 mass%) 28 .6 parts by mass and an acrylic polymer having no crosslinkable functional group (2-ethylhexyl acrylate / N-vinyl-2-pyrrolidone copolymer: 88/12 mol%, number average molecular weight: about 850,000, (Solid content: 45% by mass) 44.4 parts by mass and an acrylic oligomer having a lactam ring (2-ethylhexyl acrylate / N-vinyl-2-pyrrolidone copolymer: 80/20 mol%, number average molecular weight: about 6000, solid content: 98% by mass) 30.6 parts by mass and concentrated glycerin as a liquid component (manufactured by Kashima Chemical Co., Ltd., molecular weight 92.1, pH 7.4, steam To a mixture of less than pressure 0.1Pa (20 ℃)) 3.2 parts by weight of an isocyanate crosslinking agent (Nippon Polyurethane Industry Co., Coronate HL) was added and mixed 0.2 parts by weight.

The obtained pressure-sensitive adhesive composition solution was applied to a 50 μm thick polyethylene terephthalate film (Toray Industries, Lumirror T60) with an applicator so that the coating amount after drying was 50 g / m ² (thickness 40 μm). It was applied and dried at 100 ° C. for 3 minutes to form an adhesive layer, which was used as an adhesive sheet.

[Example 2]
A pressure-sensitive adhesive composition was prepared in the same manner as in Example 1 except that the amount of concentrated glycerin was changed to 10.6 parts by mass, and the pressure-sensitive adhesive sheet was prepared in the same manner as in Example 1 using the pressure-sensitive adhesive composition. Produced.

Example 3
A pressure-sensitive adhesive composition was prepared in the same manner as in Example 1 except that the blending amount of concentrated glycerin was changed to 25.8 parts by mass, and the pressure-sensitive adhesive sheet was prepared in the same manner as in Example 1 using the pressure-sensitive adhesive composition. Produced.

Example 4
As an acrylic oligomer having a lactam ring, an acrylic oligomer having a molar ratio of 2-ethylhexyl acrylate and N-vinyl-2-pyrrolidone copolymer of 88:12 (number average molecular weight: about 6000, solid content: 98 mass) %), And a pressure-sensitive adhesive composition was prepared in the same manner as in Example 3, and a pressure-sensitive adhesive sheet was prepared in the same manner as in Example 1 using the pressure-sensitive adhesive composition.

Example 5
The pressure-sensitive adhesive composition was changed in the same manner as in Example 1 except that the liquid component was changed to 6.7 parts by mass of polyethylene glycol (number average molecular weight 400, pH 7.1, vapor pressure less than 10 Pa (20 ° C.)) instead of concentrated glycerin. A pressure-sensitive adhesive sheet was prepared in the same manner as in Example 1 using the pressure-sensitive adhesive composition.

Example 6
The pressure-sensitive adhesive composition was the same as in Example 1 except that the liquid component was changed to 6.7 parts by mass of polypropylene glycol (number average molecular weight 2000, pH 7.2, vapor pressure less than 10 Pa (20 ° C.)) instead of concentrated glycerin. A pressure-sensitive adhesive sheet was prepared in the same manner as in Example 1 using the pressure-sensitive adhesive composition.

[Comparative Example 1]
As the pressure-sensitive adhesive sheet of Comparative Example 1, a cello tape manufactured by Nichiban Co., Ltd. was prepared. Note that the adhesive of the cello tape is mainly composed of natural rubber.

[Comparative Example 2]
A pressure-sensitive adhesive composition was prepared in the same manner as in Example 1 except that an acrylic polymer having no crosslinkable functional group, an acrylic oligomer having a lactam ring, and concentrated glycerin were not used. An adhesive sheet was prepared in the same manner as in Example 1.

[Comparative Example 3]
A pressure-sensitive adhesive composition was prepared in the same manner as in Example 1 except that an acrylic oligomer having a lactam ring and concentrated glycerin were not used, and the pressure-sensitive adhesive sheet was prepared in the same manner as in Example 1 using the pressure-sensitive adhesive composition. Was made.

  Here, the compounding ratio of each component in the pressure-sensitive adhesive compositions prepared in Examples 1 to 6 and Comparative Examples 2 to 3 is shown in Table 1.

[Test Example 1] (Measurement of remaining rate of corneum)
The pressure-sensitive adhesive sheets obtained in Examples and Comparative Examples were cut into a width of 25 mm and a length of 40 mm to obtain a sample.

  The inner side of the lower arm of the person being the measurement site was lightly wiped with a towel moistened with water and left for 20 minutes. And using the high sensitivity keratin film thickness and moisture meter (Asahi Biomed Co., Ltd., high sensitivity horny film thickness and moisture meter ASA-MX), the thickness of the corneal membrane at the measurement site when not treated was measured ( Average value of 5 measurements).

  The measurement site was lightly wiped with a towel wetted with water and left for 20 minutes. Next, after the sample was affixed to the measurement site for 5 minutes, the sample was peeled off at a speed of about 2000 mm / min by a human hand. Thereafter, the measurement site was lightly wiped with a towel wetted with water and left for 20 minutes. And using the said high sensitivity keratin film thickness and moisture meter, the thickness of the keratin membrane of the measurement site | part at the time of a 1st process was measured (average value of 5 times measurement). From the measurement results, the remaining rate (%) of the corneum was calculated based on the thickness of the corneum when not treated (100). The results are shown in Table 2.

[Test Example 2] (Sensory test during exfoliation)
The pressure-sensitive adhesive sheets obtained in Examples and Comparative Examples were cut into a width of 25 mm and a length of 40 mm to obtain a sample.

The inner side of the upper arm of the person being the measurement site was lightly wiped with a towel moistened with water and left for 20 minutes. Next, after the sample was affixed to the measurement site for 5 minutes, the sample was peeled off at a speed of about 2000 mm / min by a human hand. The pain at that time was sensory evaluated according to the following criteria. The results are shown in Table 2.
◎: No pain ○: Slightly felt △: Pain felt (can withstand)
×: I felt very painful

[Test Example 3] (Adhesive strength measurement)
For the pressure-sensitive adhesive sheets obtained in Examples and Comparative Examples (pressure-sensitive adhesive sheets in which a pressure-sensitive adhesive composition or an adhesive is formed at a thickness of 40 μm on a 50 μm-thick polyethylene terephthalate film), the adhesive strength (N / 25 mm) according to JIS Z0237 ) Was measured. In addition, a bakelite plate (manufactured by Yuko Trading Co., Ltd., Tycolite FL1063) was used as the adherend, and the pasting time was 5 minutes. The results are shown in Table 2.

  From Table 2, it can be seen that according to the pressure-sensitive adhesive sheet obtained in Examples, the stratum corneum can be effectively peeled off and there is no pain at the time of peeling.

  The exfoliating pressure-sensitive adhesive composition and exfoliating pressure-sensitive adhesive sheet of the present invention are useful when a drug is administered from the skin after peeling in addition to peeling.

Claims (11)

(Meth) acrylic polymer (a) including (meth) acrylic polymer (a1) having at least a carboxyl group as a crosslinkable functional group;
A (meth) acrylic oligomer (b) having a lactam ring having a number average molecular weight (Mn) of 4,000 to 10,000;
A crosslinking agent (c);
Containing a liquid component (d) having a number average molecular weight (Mn) of less than 4,000 ,
The (meth) acrylic polymer (a) further contains a (meth) acrylic polymer (a2) having no crosslinkable functional group having a number average molecular weight (Mn) of 300,000 to 1,500,000,
The crosslinking agent desquamating pressure-sensitive adhesive composition characterized Rukoto der isocyanate crosslinking agent.   The said liquid component (d) has as a main component the component whose vapor pressure in 20 degreeC is less than 10 Pa, The adhesive composition for keratin peeling of Claim 1 characterized by the above-mentioned.   The said liquid component (d) is a polyhydric alcohol, The horny exfoliation adhesive composition of Claim 1 characterized by the above-mentioned.   4. The (meth) acrylic oligomer (b) having a lactam ring is a copolymer of a vinyl monomer having a lactam ring and a (meth) acrylic acid alkyl ester. 2. A pressure-sensitive adhesive composition for exfoliation according to 1.   The pressure-sensitive adhesive composition for exfoliation according to claim 4, wherein the vinyl monomer having a lactam ring is N-vinyl-2-pyrrolidone.   The amount of the vinyl monomer having the lactam ring in the (meth) acrylic oligomer (b) having the lactam ring is 5 to 45 mol%, for exfoliation according to claim 4 or 5, Adhesive composition. Number average molecular weight of having a crosslinkable functional group (meth) acrylic polymer (a1) (Mn) is any one of the preceding claims, characterized in that it is 300,000～1,500,000 2. A pressure-sensitive adhesive composition for exfoliation according to 1. The amount of having a lactam ring (meth) acrylic oligomer (b), claims to the (meth) acrylic polymer (a) 100 parts by weight, characterized in that it is a 50 to 700 parts by weight The adhesive composition for exfoliation in any one of 1-7 . The addition amount of the crosslinking agent (c) include, claims, characterized in that said a 0.01 to 15 parts by weight with respect to having a crosslinkable functional group (meth) acrylic polymer (a1) 100 parts by weight The adhesive composition for exfoliation in any one of 1-8 . The compounding quantity of the said liquid component (d) is 2.5-40 mass% in an adhesive composition for keratin peeling, The adhesive for keratin peeling in any one of Claims 1-9 characterized by the above-mentioned. Composition. It was equipped with the support body and the adhesive layer formed using the adhesive composition for exfoliation in any one of Claims 1-10 laminated | stacked on the said support body. Adhesive sheet for exfoliation.