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WO2010125691A1 - Timbre adhésif - Google Patents

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Publication number
WO2010125691A1
WO2010125691A1 PCT/JP2009/058576 JP2009058576W WO2010125691A1 WO 2010125691 A1 WO2010125691 A1 WO 2010125691A1 JP 2009058576 W JP2009058576 W JP 2009058576W WO 2010125691 A1 WO2010125691 A1 WO 2010125691A1
Authority
WO
WIPO (PCT)
Prior art keywords
sensitive adhesive
meth
polyurethane resin
adhesive layer
pressure
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2009/058576
Other languages
English (en)
Japanese (ja)
Inventor
伸哉 田口
美由紀 丸山
賢治 松田
大輔 金島
肇 後藤
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Lion Corp
Original Assignee
Lion Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Lion Corp filed Critical Lion Corp
Priority to PCT/JP2009/058576 priority Critical patent/WO2010125691A1/fr
Priority to JP2011511249A priority patent/JP5348245B2/ja
Priority to KR1020117020148A priority patent/KR101581071B1/ko
Publication of WO2010125691A1 publication Critical patent/WO2010125691A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
    • A61K9/7023—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms
    • A61K9/703—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms characterised by shape or structure; Details concerning release liner or backing; Refillable patches; User-activated patches
    • A61K9/7038—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer
    • A61K9/7046—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds
    • A61K9/7053—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds obtained by reactions only involving carbon to carbon unsaturated bonds, e.g. polyvinyl, polyisobutylene, polystyrene
    • A61K9/7061—Polyacrylates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug

Definitions

  • the present invention relates to a patch comprising a support, a primer layer and an adhesive layer.
  • the polyurethane resin film has excellent stretchability and is suitable as a support for patches (see, for example, Patent Documents 1 to 3: JP-A-6-345638, JP-A-2005-89438, and JP-A-2005-21896).
  • a pressure-sensitive adhesive layer containing an acrylic (co) polymer is used for this, a cooling agent such as l-menthol, which is a component in the pressure-sensitive adhesive layer, or transdermal such as N-methyl-2-pyrrolidone
  • l-menthol which is a component in the pressure-sensitive adhesive layer
  • transdermal such as N-methyl-2-pyrrolidone
  • the absorption promoter migrated, and there were problems such as generation of wrinkles due to swelling of the film and weak anchoring property between the pressure-sensitive adhesive layer and the film. That is, it was difficult to achieve both the wrinkle prevention of the film support and the anchoring property.
  • JP-A-6-345638 JP 2005-89438 A Japanese Patent Application Laid-Open No. 2005-218496
  • the present invention has been made in view of the above circumstances, and an object of the present invention is to provide a patch that can prevent wrinkling of a support, which is a polyurethane resin film, and has good anchoring properties.
  • a pressure-sensitive adhesive layer includes a support that is an ester polyurethane resin film and a (co) polymer having (meth) acrylic acid alkyl ester as a structural unit.
  • a primer layer which is an ether-based polyurethane resin film, the wrinkle generation etc. of the film is improved, and it has been found that the anchoring property is good, and has led to the present invention. is there.
  • a primer layer and a pressure-sensitive adhesive layer containing a (co) polymer having a (meth) acrylic acid alkyl ester as a structural unit are sequentially laminated on one side of a support which is an ester polyurethane resin film, and the primer layer is an ether.
  • the patch according to [1], wherein the (co) polymer having the (meth) acrylic acid alkyl ester as a structural unit is a crosslinked (co) polymer, [3].
  • the refreshing agent is selected from 1-menthol, N-substituted-p-menthane-3-carboxamide, 3-substituted-p-menthane, 2- or 3-substituted-p-menthanediol and trialkyl substituted cyclohexanecarboxyamide
  • the adhesive patch according to [3] or [4], wherein the adhesive layer further contains a transdermal absorption enhancer, [6].
  • the patch according to [5], wherein the transdermal absorption enhancer is one or more selected from pyrrolidones, fatty acids, polybasic acids, and dihydric alcohols.
  • a pressure-sensitive adhesive layer containing a (co) polymer having a (meth) acrylic acid alkyl ester as a structural unit, which is capable of preventing wrinkles of a support made of a polyurethane film and having good anchoring properties.
  • a patch can be provided.
  • a pressure-sensitive adhesive layer containing a primer layer and a (co) polymer having a (meth) acrylic acid alkyl ester as a structural unit is sequentially laminated on one side of a support which is an ester-based polyurethane resin film.
  • the primer layer is an adhesive polyurethane resin film.
  • the support of the present invention is composed of an ester polyurethane resin film.
  • the ester-based polyurethane resin comprises a curing agent having an isocyanate group (polyisocyanate) and a polyester polyol having a hydroxyl group at the polymer terminal, and can be obtained by forming a urethane bond by a reaction between the hydroxyl group and the isocyanate group and curing it. it can.
  • An ester polyurethane resin can be used individually by 1 type or in combination of 2 or more types.
  • isocyanate examples include tolylene diisocyanate, diphenylmethane diisocyanate, hexamethylene diisocyanate, naphthalene diisocyanate, and the like, which can be used alone or in combination of two or more.
  • Polyester polyol is obtained by reacting a polybasic acid and a hydroxyl compound (glycol or polyhydric alcohol), and adipate-based polyols such as ethylene glycol adipate, diethylene adipate glycol, butylene glycol adipate, trimethylolpropane / diethylene glycol adipate, Polycaprolactone polyol (PCL) obtained by ring-opening polymerization of ⁇ -caprolactone, aromatic polyester polyol which is a polyester polyol containing terephthalic acid or isophthalic acid in dibasic acid, and linear polymer diol having hydroxyl groups at both ends Polycarbonate diol (PCD) etc. are mentioned, It can use individually by 1 type or in combination of 2 or more types.
  • PCD Polycarbonate diol
  • the ester-based polyurethane resin film of the present invention can be mixed with a resin other than the ester-based polyurethane as long as the effects of the present invention are not impaired, but the resin is preferably composed of an ester-based polyurethane resin.
  • an ultraviolet absorber, an anti-aging agent, a filler, a pigment, a colorant, a plasticizer, a flame retardant, an antistatic agent, a lubricant and the like are blended within a range not impairing the effects of the present invention. Can do.
  • the thickness of the support is preferably 5 to 40 ⁇ m, more preferably 10 to 30 ⁇ m. If the thickness is less than 5 ⁇ m, the film may not be firm and may be difficult to stick to the skin. If the thickness exceeds 40 ⁇ m, the resulting sheet will be hard, and the required flexibility such as poor texture and conformity to the skin will not be achieved. May be sufficient.
  • the 50% modulus of the support is not particularly limited, but is preferably 3.5 N / 25 mm or less, and more preferably 2.0 N / 25 mm or less. If it exceeds 3.5 N / 25 mm, there is a risk that it will not smoothly follow the expansion and contraction of the skin during application.
  • the 50% modulus is obtained by taking a 25 ⁇ 60 mm sample in both the vertical direction (flow direction during spreading) and the horizontal direction (perpendicular to the flow direction during spreading), and using a tensile testing machine, Measure the stress when stretched by 25 mm at a pulling speed of 200 mm / min.
  • the 50% elongation recovery rate of the support is not particularly limited, but is preferably 75% or more, and more preferably 85% or more in both the vertical and horizontal directions. If it is less than 75%, there is a possibility that the skin does not smoothly follow the expansion and contraction at the time of application.
  • the 50% elongation recovery rate in the present invention is obtained by taking a 10 ⁇ 150 mm sample in both directions (vertical direction of flow) and horizontal direction (perpendicular to the flow direction of spreading). Used, stretched by 50 mm at a gripping interval of 100 mm and a pulling speed of 200 mm / min, and returned until the stress becomes zero at the same speed.
  • the initial length A (100 mm) of the sample and the length B of the sample after the tensile test are read from the chart paper and calculated from the following formula.
  • 50% elongation recovery rate (%) ⁇ 100 ⁇ (BA) ⁇ ⁇ 100 / (A ⁇ 0.5) (In the above formula, A represents the initial length (100 mm) of the sample, and B represents the length (mm) of the sample after the tensile test.)
  • the moisture permeability of the support is preferably 600 to 2600 (g / m 2 ⁇ 24 hr), more preferably 800 to 1900 (g / m 2 ⁇ 24 hr). If the moisture permeability is less than 600 (g / m 2 ⁇ 24 hr), there is a risk of peeling during application, and if the moisture permeability exceeds 2600 (g / m 2 ⁇ 24 hr), the skin permeability of the drug may be reduced. .
  • the moisture permeability means a value measured according to condition B of JIS general test method “moisture-proof packaging material moisture permeability test method (cup method)” (JIS Z 0208-1976).
  • the primer layer of the present invention comprises an ether-based polyurethane resin film.
  • the ether-based polyurethane resin film comprises a curing agent having an isocyanate group (polyisocyanate) and a polyether polyol having a hydroxyl group at the polymer terminal, and is obtained by forming a urethane bond by the reaction between the hydroxyl group and the isocyanate group and curing it. be able to.
  • isocyanate examples include tolylene diisocyanate, diphenylmethane diisocyanate, hexamethylene diisocyanate, naphthalene diisocyanate, and the like, which can be used alone or in combination of two or more.
  • polyether polyol examples include polypropylene (ethylene) polyol (PPG), polytetramethylene ether glycol (PTMEG), and the like, which can be used singly or in appropriate combination of two or more.
  • PPG polypropylene (ethylene) polyol
  • PTMEG polytetramethylene ether glycol
  • the ether-based polyurethane resin film can be mixed with a resin other than the ether-based polyurethane as long as the effects of the present invention are not impaired, but the resin is preferably composed of an ether-based polyurethane resin.
  • an ultraviolet absorber, an anti-aging agent, a filler, a pigment, a colorant, a plasticizer, a flame retardant, an antistatic agent, a lubricant and the like are blended within a range not impairing the effects of the present invention. Can do.
  • the blending amount of the ether polyurethane resin is preferably 60 to 100% by mass, more preferably 80 to 100% by mass in the ether polyurethane resin film.
  • the compounding amount of the additive is more preferably 1 to 10% by mass in the ether polyurethane resin film.
  • ether-based polyurethane resin film used in the primer layer of the present invention examples include “Sapilia” (all resins are made of ether-based polyurethane resin, manufactured by Sakata Inx Corporation).
  • a primer layer which is an ether-based polyurethane resin film
  • an ether-based polyurethane resin is dissolved in an appropriate solvent to prepare a primer layer coating solution, and this is applied to the support surface.
  • the primer layer can be laminated by coating and drying.
  • the said additive can be suitably mix
  • the coating method is not particularly limited and is usually selected, for example, a forward rotation roll coater, a reverse roll coater, a gravure coater, a doctor knife coater, a blade coater, a rod coater, an air doctor coater, a curtain coater, a fountain.
  • a coater, kiss coater, dip coating, screen coating, spin coating, cast coating, spray coating, extrusion coating, vacuum coating, etc. can be used.
  • the thickness of the primer layer is preferably 1 to 20 ⁇ m, more preferably 3 to 10 ⁇ m. If the thickness of the primer layer is less than 1 ⁇ m, the anchoring force may be insufficient, and if it exceeds 20 ⁇ m, the primer layer may become hard and the flexibility required for the resulting sheet may be insufficient. .
  • the thickness of the support on which the primer layer is laminated is preferably 6 to 40 ⁇ m, more preferably 13 to 30 ⁇ m. If the thickness is less than 6 ⁇ m, the stiffness of the film becomes insufficient. If the thickness exceeds 40 ⁇ m, the obtained sheet is hard, the texture and the familiarity with the skin are deteriorated, and the required flexibility may be insufficient.
  • the 50% modulus of the support on which the primer layer is laminated is not particularly limited, but is preferably 3.5 N / 25 mm or less, and more preferably 2.0 N / 25 mm or less. If it exceeds 3.5 N / 25 mm, it may not follow the expansion and contraction of the skin smoothly at the time of application.
  • the 50% modulus is obtained by taking a 25 ⁇ 60 mm sample in both the vertical direction (flow direction during spreading) and the horizontal direction (perpendicular to the flow direction during spreading), and using a tensile testing machine, Measure the stress when stretched by 25 mm at a pulling speed of 300 mm / min.
  • the 50% elongation recovery rate of the support on which the primer layer is laminated is not particularly limited, but the 50% elongation recovery rate is preferably 75% or more, more preferably 85% or more in both the vertical and horizontal directions. If it is less than 75%, there is a possibility that the skin does not smoothly follow the expansion and contraction at the time of application.
  • the moisture permeability of the support on which the primer layer is laminated is preferably 500 to 2500 (g / m 2 ⁇ 24 hr), more preferably 700 to 1800 (g / m 2 ⁇ 24 hr). If the moisture permeability is less than 500 (g / m 2 ⁇ 24 hr), there is a risk of peeling during application, and if the moisture permeability exceeds 2500 (g / m 2 ⁇ 24 hr), the skin permeability of the drug may be reduced. .
  • the adhesive layer of this invention contains the (co) polymer which has a (meth) acrylic-acid alkylester as a structural unit.
  • pressure-sensitive adhesive composition plaster
  • the (meth) acrylic acid alkyl ester specifically, a linear alkyl group having 4 to 13 carbon atoms such as butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, etc.
  • branched alkyl groups such as 2-ethylhexyl, and the like can be used singly or in appropriate combination of two or more.
  • (meth) acrylic acid refers to acrylic acid and / or methacrylic acid.
  • the ratio of the (meth) acrylic acid alkyl ester monomer to the total amount of monomers constituting the (co) polymer is preferably 60 to 100% by mass, and more preferably 85 to 100% by mass.
  • a monomer copolymerizable with the above (meth) acrylic acid alkyl ester can be used.
  • Such monomers include hydroxyl-containing monomers such as (meth) acrylic acid, itaconic acid, maleic acid, maleic anhydride, vinyl alcohol, 2-hydroxy (meth) acrylate, hydroxypropyl (meth) acrylate, Sulfoxyl group-containing monomers such as styrene sulfonic acid, allyl sulfonic acid and sulfopropyl acrylate, amino group-containing monomers such as dimethylaminoethyl acrylate and vinyl pyrrolidone, (meth) acrylic acid hydroxyethyl ester, (meth) acrylic acid Hydroxyl group-containing monomers such as hydroxypropyl ester, (meth) acrylamide, dimethyl (meth) acrylamide, amide group-containing acrylic monomers such as N-butyl (meth) acrylamide, (
  • the copolymer of the present invention includes a (co) polymer having a (meth) acrylic acid alkyl ester as a structural unit, a (co) polymer having a (meth) acrylic acid alkyl ester and (meth) acrylic acid as a structural unit. Is particularly preferred.
  • Examples of the polymerization initiator used in the synthesis of the (co) polymer of the present invention include aqueous radical polymerization such as persulfates such as ammonium persulfate and sodium persulfate, lauroyl peroxide, hydrogen peroxide, and t-butyl hydroperoxide.
  • aqueous radical polymerization such as persulfates such as ammonium persulfate and sodium persulfate, lauroyl peroxide, hydrogen peroxide, and t-butyl hydroperoxide.
  • An initiator or a mixture thereof may be mentioned, and the amount used is usually from 0.1 to 5% by mass of the polymerization initiator, preferably 0.1 to 2% by mass, based on the total amount of monomers.
  • a redox system can be formed in combination with a reducing agent together with a polymerization initiator.
  • reducing agents examples include alkali metal salts and ammonium salts such as sulfites, bisulfites, pyrosulfites, and formaldehyde sulfonates, and carboxylic acids such as L-ascorbic acid and tartaric acid.
  • alkali metal salts and ammonium salts such as sulfites, bisulfites, pyrosulfites, and formaldehyde sulfonates
  • carboxylic acids such as L-ascorbic acid and tartaric acid.
  • the polymerization may be emulsion polymerization
  • the surfactant used in the emulsion polymerization may be an anionic, cationic, nonionic, amphoteric surfactant or a mixture thereof.
  • anionic surfactants include alkyl or alkyl allyl sulfates such as sodium lauryl sulfate and sodium dodecylbenzene sulfonate, alkyl or alkyl allyl sulfonates, dialkyl sulfosuccinates, polyoxyethylene (3) lauryl ether sulfates
  • alkali metal salts such as sodium and polyoxyethylene alkyl ether sulfates such as sodium polyoxyethylene (4) lauryl ether sulfate and ammonium salts.
  • Nonionic surfactants include polyoxyethylene lauryl ether, polyoxyethylene alkyl ethers such as polyoxyethylene oleyl ether, polyoxyethylene alkyl phenyl ethers such as polyoxyethylene nonyl phenyl ether, polyoxyethylene octyl phenyl ether, and monolaurin. And polyoxyethylene fatty acid esters such as polyethylene glycol acid and polyethylene glycol monooleate.
  • amphoteric surfactants include betaine and amino acid derivatives.
  • An example of a peptide surfactant is surfactin sodium.
  • the amount of the surfactant used is preferably 0.1 to 5 parts by mass, more preferably 0.3 to 3 parts by mass with respect to the total amount of monomers. If the amount used is less than 0.1 parts by mass, the reaction may become unstable, and if it exceeds 5 parts by mass, the drying property and water resistance may be deteriorated.
  • emulsion polymerization may be carried out with a chain transfer agent such as a chelating agent such as ethylenediaminetetraacetic acid sodium, a dispersant such as polycarboxylate, an inorganic salt such as phosphate or carbonate, a thiol compound, or a halogen compound. You may go in the presence.
  • a chain transfer agent such as a chelating agent such as ethylenediaminetetraacetic acid sodium, a dispersant such as polycarboxylate, an inorganic salt such as phosphate or carbonate, a thiol compound, or a halogen compound. You may go in the presence.
  • the (co) polymer of the present invention include, for example, acrylic acid / acrylic acid octyl ester copolymers and acrylics listed in the Pharmaceutical Additives Encyclopedia 2000 (edited by Japan Pharmaceutical Additives Association) as an adhesive.
  • a polymer resin emulsion, DURO-TAK acrylic pressure-sensitive adhesive series (National Starch and Chemical Co., Ltd.), Eudragit series (Higuchi Shokai) and the like can be suitably used.
  • the blending amount of the (co) polymer of the present invention is not particularly limited and can be appropriately selected.
  • the solid content relative to the total amount of the pressure-sensitive adhesive composition (composition constituting the pressure-sensitive adhesive layer). 40 to 95% by mass, preferably 50 to 90% by mass, and more preferably 55 to 85% by mass. Within this range, there is little peeling or turning when applied to the skin.
  • the (co) polymer of the present invention is further subjected to a crosslinking treatment by a crosslinking means, and the crosslinked (co) polymer having a (meth) acrylic acid alkyl ester as a structural unit is aggregated as an adhesive layer.
  • a crosslinking means prevents the components such as l-menthol and other refreshing agents and transdermal absorption accelerators such as N-methyl-2-pyrrolidone in the pressure-sensitive adhesive layer described below from moving to the film. It is preferable to suppress the generation of wrinkles due to swelling of the film and the decrease in anchoring property between the pressure-sensitive adhesive layer and the film.
  • Cross-linking treatment includes physical cross-linking by irradiation such as ultraviolet ray irradiation and electron beam irradiation, and chemical cross-linking treatment using cross-linking agents such as polyisocyanate compounds, organic peroxides, organometallic salts, metal alcoholates, and polyfunctional compounds. Etc. are used.
  • cross-linking agents such as polyisocyanate compounds, organic peroxides, organometallic salts, metal alcoholates, and polyfunctional compounds. Etc. are used.
  • cross-linking agents such as polyisocyanate compounds, organic peroxides, organometallic salts, metal alcoholates, and polyfunctional compounds. Etc. are used.
  • cross-linking agents such as polyisocyanate compounds, organic peroxides, organometallic salts, metal alcoholates, and polyfunctional compounds. Etc. are used.
  • cross-linking agents such as polyisocyanate compounds, organic peroxides, organometallic salts, metal alcoholates, and polyfunctional
  • a method of previously copolymerizing a polyfunctional monomer such as diacrylate with an acrylate ester polymer is also conceivable, but in this case, the solution viscosity may increase.
  • these crosslinking agents potassium aluminum sulfate, zinc sulfate and trifunctional isocyanate are preferable, and potassium aluminum sulfate and zinc sulfate are more preferable.
  • These cross-linking agents do not cause a thickening phenomenon of the solution until coating and drying, are extremely excellent in workability, and increase the anchoring property of the pressure-sensitive adhesive and the film by coating uniformly.
  • the crosslinking agent used for the crosslinking means can be used singly or in appropriate combination of two or more, and the blending amount is not particularly limited and can be appropriately selected, and the total amount of the pressure-sensitive adhesive composition On the other hand, it is usually preferably 0.1 to 5.0% by mass, more preferably 0.4 to 3.0% by mass.
  • the amount used is less than 0.1% by mass, components such as l-menthol and N-methyl-2-pyrrolidone tend to migrate to the film, and wrinkles due to film swelling may occur. If it exceeds 5.0% by mass, the adhesive strength of the adhesive may be reduced.
  • a cooling agent or a drug can be blended as necessary.
  • the kind of the refreshing agent is not limited as long as it is a substance that imparts a refreshing feeling.
  • Examples of such a refreshing agent include 1-menthol, N-substituted-p-menthane-3-carboxamide, 3- Examples thereof include substituted-p-menthane, 2- or 3-substituted-p-menthanediol, and trialkyl-substituted cyclohexanecarboxyamide, and these can be used alone or in combination of two or more.
  • l-menthol is particularly preferable because it gives a strong refreshing feeling, and it is desirable to use l-menthol alone or in combination with other cooling agents.
  • the blending amount is preferably 0.1 to 10.0% by mass, more preferably 0.5 to 7.0% by mass with respect to the total amount of the pressure-sensitive adhesive composition. If the amount used is less than 0.1% by mass, a refreshing feeling may not be imparted. If it exceeds 10.0% by mass, wrinkles due to swelling of the film and anchorage between the pressure-sensitive adhesive layer and the film may be reduced.
  • Drugs include warmth-imparting agents, non-steroidal anti-inflammatory agents, steroidal anti-inflammatory agents, antihistamines such as diphenhydramine, central nervous system drugs such as isoprenaline hydrochloride; hormonal agents such as estradiol and testosterone; aspirin, acetaminophen, Analgesics such as ibuprofen; antiarrhythmic agents such as disopyramide phosphate, coronary vasodilators such as tolazoline hydrochloride, local anesthetics such as lidocaine, muscle relaxants such as squismethonium chloride, antifungal agents such as clotrimazole, fluorouracil Antineoplastic agents such as tamsulosin hydrochloride, urination disorder improving agents such as diazepam, antiepileptic agents such as diazepam, antiparkinsonian agents such as bromocriptine mesylate; antihypertensive agents such as furosemide and
  • warming agent examples include capsaicin analogs such as capsicoside, capsaicin, capsaicinoid, divitrocapsaicin, capsanthin, capsicum extract, capsicum extract 20, capsicum-derived substances such as capsicum tincture and capsicum powder, benzyl nicotinate, ⁇ -nicotinic acid ⁇ - Examples include butoxyethyl, N-acyl vanillamide, nonyl acid vanillamide, vanillyl alcohol alkyl ether, and the like.
  • Non-steroidal anti-inflammatory agents include salicylic acid and its salts, salicylic acid derivatives such as aspirin, acetaminophen, aminopyrine, antipyrine, oxyphenbutazone, sulpyrine, ampenac sodium, indomethacin, diclofenac, diclofenac sodium, felbinac, ibuprofen , Sulindac, naproxen, ketoprofen, suprofen, etofenamate, salicylamide, triethanolamine salicylate, flufenamic acid and its salts and derivatives, meclofenamic acid and its salts and derivatives, colchicine, bufexamac, ibufenac, loxoprofen , Fenbufen, diflunisal, alclofenac, phenylbutazone, mefenamic acid and its salts and its derivatives, Profens, bendazac, piroxicam, flurbiprofen, z
  • steroidal anti-inflammatory agents include amsinoid, prednisolone valerate, prednisolone valerate, diflucortron valerate, betamethasone valerate, betamethasone acetate, dexamethasone acetate, dexamethasone hydrochloride, betamethasone dipropionate, dexamethasone, triamcinolone acetonide, rilcinonide.
  • Hydrocortisone hydrocortisone acetate
  • flumethasone pivalate fluocinonide, fluocinolone acetonide, fluotometholone, fludroxycortide, prednisolone, prednisolone acetate, clobetasol propionate, beclomethasone propionate, betamethasone, methylprednisolone acetate And hydrocortisone.
  • the drug can be used singly or in appropriate combination of two or more, and the blending amount thereof is not particularly limited and can be appropriately selected, and is 0.1% relative to the total amount of the pressure-sensitive adhesive composition. ⁇ 10.0 mass% is preferable, and 0.1 to 7.0 mass% is more preferable.
  • antioxidants can be used singly or in appropriate combination of two or more.
  • a transdermal absorption enhancer can be blended in the pressure-sensitive adhesive composition.
  • the percutaneous absorption enhancer may be any agent that improves the percutaneous absorbability of the active ingredient in the external preparation for skin.
  • examples of such a component include pyrrolidones, azone (1-dodecylazacycloheptane-2- ON), calcium thioglycolate, higher alcohols, enamines and derivatives thereof, fatty acids, dihydric alcohols, salicylic acids, polybasic acids, crotamiton, terpenes, benzyl alcohol, squalane and the like. In this case, these can be used alone or in combination of two or more.
  • pyrrolidones include 2-pyrrolidone, N-methyl-2-pyrrolidone, 5-methyl-2-pyrrolidone, 1,5-dimethyl-2-pyrrolidone, 1-ethyl-2-pyrrolidone, Examples include pyrrolidone such as 2-pyrrolidone-5-carboxylic acid and salts thereof, and derivatives and salts thereof.
  • Specific examples of higher alcohols include oleyl alcohol, lauryl alcohol, myristyl alcohol, and 2-octyldodecanol.
  • polybasic acids include, for example, diethyl adipate, adipine Polybasic acids having 2 or more carbon atoms, such as isopropyl acid and diisopropyl adipate, and their derivatives
  • fatty acids having transdermal absorption promoting action specifically fatty acids having 8 to 22 carbon atoms such as sodium caprate, linoleic acid, oleic acid, sodium lauryl sulfate, sodium cetyl sulfate, and salts thereof , Ethyl myristate, octyldodecyl myristate, isopropyl myristate, diisopropyl sebacate, diethyl sebacate, isopropyl palmitate, decyl
  • N-methyl-2-pyrrolidone, isopropyl myristate, diisopropyl adipate, decyl oleate, oleyl oleate, and dipropylene glycol are particularly preferred from the viewpoint of promoting percutaneous absorption of drugs.
  • the percutaneous absorption enhancer can be used singly or in appropriate combination of two or more, and the total blending amount thereof is not particularly limited and can be selected as appropriate, with respect to the total amount of the pressure-sensitive adhesive composition. 0.5 to 30.0% by mass is preferable, and 5.0 to 25.0% by mass is more preferable. If this blending amount is less than 0.5% by mass, the transdermal absorbability of the drug may be lowered, and if it exceeds 30.0% by mass, it tends to shift to a film, causing wrinkles due to swelling of the film and an adhesive. There is a possibility that the anchoring property between the layer and the film is lowered.
  • the blending amount of N-methyl-2-pyrrolidone is preferably 0.5 to 5.0% by mass.
  • the pressure-sensitive adhesive layer of the present invention is a non-aqueous pressure-sensitive adhesive formed by applying a coating liquid for a pressure-sensitive adhesive layer, which will be described later, on a primer layer or a liner, which will be described later, and drying from the viewpoint of adhesive strength and cohesive strength. It is preferable to use an agent layer.
  • the non-aqueous pressure-sensitive adhesive layer may contain moisture from the raw material, between manufacturing steps, or from the environment, but the smaller the moisture content, the better. Specifically, the water content is preferably 3.0% by mass or less, more preferably 1.0% by mass or less, and preferably no water in the non-aqueous pressure-sensitive adhesive layer.
  • the primer layer and the pressure-sensitive adhesive layer are sequentially laminated on one side of the support, and a patch including the support, the primer layer, and the pressure-sensitive adhesive layer is formed.
  • Lamination of the pressure-sensitive adhesive layer to the primer layer laminated on the support is performed, for example, by (i) preparing a coating solution for the pressure-sensitive adhesive layer, and (ii) applying this pressure-sensitive adhesive solution to the liner and drying it.
  • the adhesive layer is laminated on one side of the liner.
  • the pressure-sensitive adhesive layer provided on one side of the liner is laminated on the surface of the primer layer laminated on the support.
  • (I) Preparation of coating solution for pressure-sensitive adhesive layer After mixing (co) polymer having (meth) acrylic acid alkyl ester as a structural unit and other optional components, the solid content is 30 to 80% by mass, preferably The pressure-sensitive adhesive layer coating solution is obtained by adjusting with a solvent so as to be 40 to 60% by mass.
  • a solvent so as to be 40 to 60% by mass.
  • water, methanol, ethanol, acetone, ethyl acetate, toluene, and other organic solvents can be used, but water, ethanol, and ethyl acetate are preferable.
  • This pressure-sensitive adhesive solution is coated on a liner.
  • the solvent of the pressure-sensitive adhesive layer coating solution is water, for example, after dissolving the cross-linking agent and the chelating agent in water, preferably with sodium hydroxide, potassium hydroxide or ammonia water, the pH to the alkali side, The pH is preferably adjusted to 8 or more, more preferably to pH 9-12.
  • An acrylic (co) polymer and other optional components are mixed with this, and after sufficiently stirring until the whole becomes uniform, coating is performed.
  • the solvent is ethyl acetate
  • the above (co) polymer, preferably a cross-linking agent, and other components are mixed in ethyl acetate and stirred sufficiently until the whole becomes uniform, and then coating is performed. Do.
  • the liner examples include a vinyl chloride film, a polyethylene film, a polypropylene film, a polyester film, a medicinal rule polyethylene terephthalate separator, a release paper (release paper), and the like.
  • the coating method is not particularly limited, and a method conventionally selected on the surface of the primer layer laminated on the support, for example, a comma coater, a forward rotation roll coater, a reverse roll coater, a gravure coater, a doctor knife coater, a blade.
  • Coating is performed by a coater, rod coater, air doctor coater, curtain coater, fountain coater, kiss coater, dip coating, screen coating, spin coater, cast coating, spray coating, extrusion coating, vacuum coating and the like.
  • the coating amount of the adhesive composition preferably 1 ⁇ 500g / m 2, more preferably 5 ⁇ 250g / m 2, more preferably 10 ⁇ 200g / m 2.
  • the coating amount of the adhesive composition preferably 1 ⁇ 500g / m 2, more preferably 5 ⁇ 250g / m 2, more preferably 10 ⁇ 200g / m 2.
  • 0.03 to 1.7 g is preferable, and 0.07 to 1.4 g / m 2 is more preferable.
  • the drying process for distilling off the solvent is, for example, hot air high-speed air cap, hot air tunnel type, hot air air floating, air through, N 2 gas displacement drying system, infrared, microwave, (electromagnetic) induction heating, ultraviolet curing, lamp
  • a hot air high-speed air cap, a hot air tunnel type, and a hot air air floating are preferably used.
  • the drying conditions in the present invention may be at least the temperature at which the pressure-sensitive adhesive is crosslinked or the temperature at which the solvents are volatilized, but are usually 40 to 150 ° C., preferably 60 to 130 ° C., more preferably 70 to 120 ° C. When this temperature is too low, the volatilization of the solvent becomes insufficient, and when it exceeds 150 ° C., when a drug or plasticizer is blended, these may be affected.
  • a liner (polyester film (75 ⁇ m)) was applied to a liner (polyester film (75 ⁇ m)) with a comma coater so that the amount of plaster after drying was 1.0 g / 10 ⁇ 7 cm, and dried. Drying was performed in a 90 ° C. dryer for 15 minutes.
  • the primer layer was laminated
  • Example 12 A copolymer emulsion, a percutaneous absorption enhancer in which a drug was dissolved, and a crosslinking agent were mixed and sufficiently stirred until the whole became uniform to prepare an adhesive layer coating solution.
  • a liner (polyester film (75 ⁇ m)) was applied to a liner (polyester film (75 ⁇ m)) with a comma coater so that the amount of plaster after drying was 1.0 g / 10 ⁇ 7 cm, and dried. Drying was performed in a 90 ° C. dryer for 15 minutes.
  • the primer layer was laminated
  • the pressure-sensitive adhesive layer provided on one side of the liner was laminated on the surface of the primer layer laminated on the support, and cut into an appropriate size to obtain a patch of each example. In the table, the pressure-sensitive adhesive layer composition after drying is shown.
  • ⁇ Throwing property evaluation> The amount of plaster remaining on the skin relative to the total amount of paste (total amount of the adhesive composition) when the patch was applied to the skin (sex; male, age 20-40 years, 10 people) for 3 hours and peeled off The ratio (%) was obtained. This was used as an index of anchoring property between the support and the adhesive.

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Abstract

Cette invention concerne un timbre adhésif qui a un bon effet d'ancrage et évite la formation de plis sur un support comportant une pellicule de résine de polyuréthane. Ce timbre adhésif se caractérise en ce qu'une couche d'amorce et une couche adhésive qui contient un (co)polymère renfermant du (méth)acrylate sont agencées séquentiellement d'un côté du support comportant une pellicule de résine de polyuréthane à base d'ester. Le timbre adhésif se caractérise également en ce que la couche d'amorce comporte une pellicule de résine de polyuréthane à base d'éther.
PCT/JP2009/058576 2009-05-01 2009-05-01 Timbre adhésif Ceased WO2010125691A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
PCT/JP2009/058576 WO2010125691A1 (fr) 2009-05-01 2009-05-01 Timbre adhésif
JP2011511249A JP5348245B2 (ja) 2009-05-01 2009-05-01 貼付剤
KR1020117020148A KR101581071B1 (ko) 2009-05-01 2009-05-01 첩부제

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PCT/JP2009/058576 WO2010125691A1 (fr) 2009-05-01 2009-05-01 Timbre adhésif

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WO2010125691A1 true WO2010125691A1 (fr) 2010-11-04

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PCT/JP2009/058576 Ceased WO2010125691A1 (fr) 2009-05-01 2009-05-01 Timbre adhésif

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JP (1) JP5348245B2 (fr)
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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013095749A (ja) * 2011-11-01 2013-05-20 Toko Yakuhin Kogyo Kk 外用貼付剤
WO2014142177A1 (fr) 2013-03-14 2014-09-18 株式会社カネカ Procédé de production de polymère
WO2018051693A1 (fr) * 2016-09-15 2018-03-22 日東電工株式会社 Stratifié pour adhérence à un corps vivant
US10138309B2 (en) 2015-02-13 2018-11-27 Kaneka Corporation Method for producing particulate polymer

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JPH06345638A (ja) 1993-06-04 1994-12-20 Sekisui Chem Co Ltd 貼付剤
JP2005089438A (ja) 2003-09-19 2005-04-07 Kosumedei:Kk 皮膚用粘着剤組成物及び皮膚用粘着テープまたはシート
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JPH08119857A (ja) * 1994-10-24 1996-05-14 Bando Chem Ind Ltd 皮膚貼付薬シート及びその製造方法
JP2000327955A (ja) * 1999-05-14 2000-11-28 Nitto Denko Corp プライマー組成物及び当該プライマー組成物を用いた医療用粘着テープ若しくはシート
JP2003095929A (ja) * 2001-09-27 2003-04-03 Lion Corp 貼付剤
JP2003190205A (ja) * 2001-12-28 2003-07-08 Nitto Denko Corp 皮膚貼付用粘着シートおよびその製造方法
JP2003342541A (ja) * 2002-05-29 2003-12-03 Nitto Denko Corp 粘着シート
JP2004010662A (ja) * 2002-06-04 2004-01-15 Nitto Denko Corp 複合フィルムとその製造方法および粘着シート
JP2006104174A (ja) * 2004-10-08 2006-04-20 Lion Corp 貼付剤
JP2006182652A (ja) * 2004-12-24 2006-07-13 Bando Chem Ind Ltd 経皮吸収型製剤用基材シート及び経皮吸収型製剤
JP2008094794A (ja) * 2006-10-13 2008-04-24 Nippon Denshi Seiki Kk 貼付剤
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WO2009041121A1 (fr) * 2007-09-28 2009-04-02 Yugen Kaisha Kazki Reiko Matériau de timbre auxiliaire cosmétique et procédé de cosmétisation avec celui-ci

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013095749A (ja) * 2011-11-01 2013-05-20 Toko Yakuhin Kogyo Kk 外用貼付剤
WO2014142177A1 (fr) 2013-03-14 2014-09-18 株式会社カネカ Procédé de production de polymère
US9376547B2 (en) 2013-03-14 2016-06-28 Kaneka Corporation Polymer production method
US10138309B2 (en) 2015-02-13 2018-11-27 Kaneka Corporation Method for producing particulate polymer
WO2018051693A1 (fr) * 2016-09-15 2018-03-22 日東電工株式会社 Stratifié pour adhérence à un corps vivant

Also Published As

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KR101581071B1 (ko) 2015-12-30
JPWO2010125691A1 (ja) 2012-10-25
JP5348245B2 (ja) 2013-11-20
KR20120022711A (ko) 2012-03-12

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