WO2021192366A1 - Patch - Google Patents

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Publication number
WO2021192366A1
WO2021192366A1 PCT/JP2020/036894 JP2020036894W WO2021192366A1 WO 2021192366 A1 WO2021192366 A1 WO 2021192366A1 JP 2020036894 W JP2020036894 W JP 2020036894W WO 2021192366 A1 WO2021192366 A1 WO 2021192366A1
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WO
WIPO (PCT)
Prior art keywords
water
adhesive layer
mass
pressure
sensitive adhesive
Prior art date
Application number
PCT/JP2020/036894
Other languages
English (en)
Japanese (ja)
Inventor
篤 村田
眞 金箱
萩原　勲
Original Assignee
ニチバン株式会社
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 ニチバン株式会社 filed Critical ニチバン株式会社
Priority to TW110110946A priority Critical patent/TW202202147A/zh
Priority to CN202180015558.5A priority patent/CN115315262A/zh
Priority to PCT/JP2021/012730 priority patent/WO2021193874A1/fr
Priority to JP2022510699A priority patent/JPWO2021193874A1/ja
Priority to KR1020227035644A priority patent/KR20220158748A/ko
Publication of WO2021192366A1 publication Critical patent/WO2021192366A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/60—Salicylic acid; Derivatives thereof
    • 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
    • A61K47/02—Inorganic compounds
    • 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
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
    • 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
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
    • A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
    • 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
    • A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
    • 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
    • A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
    • A61K47/38—Cellulose; Derivatives thereof
    • 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 water-containing patch, and more specifically, the present invention has good adhesive strength in spite of the water-containing system, the stability of the glycol salicylate to be blended is good, and the cross-linking degree is appropriate. Regarding water-containing patches.
  • a patch using a water-containing adhesive base which is also generally referred to as a "pap agent” (referred to as a water-containing patch in the present specification) is a plaster layer (adhesive layer) containing an active ingredient such as a drug. It is a kind of adhesive provided on a support such as a non-woven fabric. Since the poultice uses an adhesive base containing water in the plaster layer, the adhesive strength is weak although the skin irritation is low, and in particular, the adhesive strength decreases with time as the water in the plaster layer volatilizes. The problem was that it was easy to peel off from the skin.
  • an emulsion (also called emulsion) base in which an acrylic acid alkyl ester copolymer known as one component constituting a non-aqueous (also referred to as hydrophobic or lipophilic) adhesive is dispersed is used.
  • a technique of blending a water-containing patch into a plaster layer (adhesive layer) is known.
  • Patent Document 1 contains 1% of a methyl acrylate / 2-ethylhexyl acrylate copolymer resin emulsion (trade name: Nicazole TS-620, Nippon Carbide Industries, Ltd.) in a poultice base (plaster).
  • a patch (comparative product) is disclosed.
  • Patent Document 2 provides a water-containing patch that can exhibit adhesive strength and re-adhesive strength during long-term application, suppress deterioration of hardening and suppleness due to water loss, and suppress breakage of the support during peeling.
  • the water-dispersible surfactant was added in an amount of 0.01% by mass or more and 10.0% by mass or less, and the methyl acrylate / 2-ethylhexyl acrylate copolymer was added to the entire composition for a water-containing external patch.
  • a water-containing external patch containing 5.0% by mass or more and 10% by mass or less is disclosed.
  • Patent Document 3 describes a partially neutralized polyacrylic acid and the neutralized product, with the object of providing a poultice having sufficient adhesive strength even when the water content of the poultice decreases over time.
  • Patent Document 4 includes poly (methyl acrylate / 2-ethylhexyl acrylate) and a surfactant such as polyethylene glycol fatty acid ester for the purpose of providing a poultice that can peel off the release liner with a smaller force.
  • Pap agents are disclosed.
  • Patent Document 5 discloses that a cold sheet was obtained using an adhesive composition containing 1.5% by weight of an acrylic resin emulsion (trade name: Nicazole TS-620) and 6.2% by weight of sodium polyacrylate. ing.
  • Japanese Unexamined Patent Publication No. 9-208462 Japanese Patent No. 5650684 Japanese Patent No. 5921779 International Publication No. 2016/10427 JP-A-2002-104957
  • an acrylic acid alkyl ester copolymer such as a methyl acrylate / 2-ethylhexyl acrylate copolymer is blended in the pressure-sensitive adhesive layer in order to enhance the adhesive durability of the water-containing patch.
  • glycol salicylate has a problem in its drug stability under an aqueous solvent, that is, the stability and adhesive strength of the drug in a water-containing patch containing glycol salicylate have not yet been sufficiently satisfied. ..
  • the present inventors have made a pressure-sensitive adhesive in order to achieve both stability of glycol salicylate in a water-containing patch, improvement of adhesiveness of a preparation, and appropriate degree of cross-linking.
  • the present invention has been completed by finding that the above problems can be solved by adjusting the pH of the (plaster), particularly by blending hydrochloric acid as an essential component for adjusting the pH.
  • the present invention is a water-containing patch comprising a support, a pressure-sensitive adhesive layer provided on the support, and a release liner stuck on the pressure-sensitive adhesive layer.
  • the pressure-sensitive adhesive layer contains the following components a) to h) as essential components.
  • the blending amount of glycerin in the pressure-sensitive adhesive layer is more than 15 times and 18 times or less on a mass basis with respect to the blending amount of glycol salicylate.
  • the water-containing patch having a pH value of 4.00 to 4.85 in the pressure-sensitive adhesive layer.
  • 2) When the total mass of the pressure-sensitive adhesive layer is 100% by mass a) Glycol salicylate is 0.1 to 30% by mass, b) 0.1 to 5% by mass of the (meth) acrylic acid alkyl ester copolymer, c) Polyacrylic acid partially neutralized product in an amount of 3.5 to 4.5% by mass, d) 2.0 to 30% by mass of a water-soluble polymer compound containing sodium carmellose, e) 30-70% by mass of a wetting agent containing glycerin, f) 0.01 to 6.0% by mass of cross-linking agent, g) Hydrochloric acid 0.1-1.5% by mass, h) Add 10 to 90% by mass of water, The water-containing patch, which is blended in the ratio of.
  • the water-containing patch having a compounding amount of 3.5% by mass or more and a compounding amount of sodium carmellose of 2.0% by mass or more.
  • the (meth) acrylic acid alkyl ester is a copolymer of a monomer mixture composed of monomer A and monomer B, and the monomer A has a glass transition temperature (Tg) when the monomer A is homopolymerized.
  • the water-containing patch which is a monomer that becomes a polymer of 270 K or more, and the monomer B is a monomer that becomes a polymer having a glass transition temperature (Tg) of 220 K or less when the monomer B is homopolymerized.
  • the water-containing patch having a degree of neutralization of 30% to 65% and a viscosity of a 0.2 mass% aqueous solution thereof of 450 to 650 mPa ⁇ s.
  • the water-containing patch having a viscosity of a 1% by mass aqueous solution thereof of 1,000 to 3,000 mPa ⁇ s and a transesterification degree of 0.60 to 0.95.
  • the water-containing patch, wherein the cross-linking agent is a poorly soluble aluminum compound.
  • the water-containing patch wherein the pressure-sensitive adhesive layer is formed from a pressure-sensitive adhesive layer-forming composition containing the components a) to h) and having a viscosity of 90 to 250 Pa ⁇ s.
  • the water-containing patch, wherein the pressure-sensitive adhesive layer further contains i) sodium edetate hydrate as a chelating agent.
  • glycol salicylate in a water-containing patch containing glycol salicylate in the pressure-sensitive adhesive layer, by blending hydrochloric acid in the pressure-sensitive adhesive layer, glycol salicylate, which is an active ingredient, is stable over time and the adhesive strength of the preparation is also increased. It is possible to provide a water-containing patch having a high degree of cross-linking and a good degree of cross-linking. Further, according to the present invention, a water-containing system capable of maintaining adhesive strength even after the water content in the adhesive layer volatilizes, having low skin irritation, low adhesiveness between plasters, and reapplyable to the skin. A patch can be provided.
  • the present inventors are inorganic acids in a water-containing patch, particularly a water-containing patch in which a non-water-based adhesive base is blended in a plaster layer (adhesive layer) of the water-containing patch.
  • a water-containing patch in which a non-water-based adhesive base is blended in a plaster layer (adhesive layer) of the water-containing patch.
  • hydrochloric acid By blending hydrochloric acid into the pressure-sensitive adhesive layer, the pH of the pressure-sensitive adhesive (plaster) is adjusted. Specifically, by tilting the pH value of the pressure-sensitive adhesive layer from the neutral side to the acidic side, the presence of water Drugs below:
  • the stability of glycol salicylate can be improved.
  • the formulation of hydrochloric acid can improve not only drug stability but also the degree of cross-linking and adhesive strength, which cannot be said to be sufficient with the use of other acids.
  • the configuration of the water-containing patch of the present invention will be described.
  • the water-containing patch of the present invention (hereinafter, also simply referred to as “sticker”) comprises a support, a pressure-sensitive adhesive layer provided on the support, and a release liner attached to the pressure-sensitive adhesive layer.
  • the shape of the patch, particularly the support, and the preparation portion composed of the pressure-sensitive adhesive layer provided on the support is not particularly limited, and is square (square, rectangle, etc.), quadrangle (trapezoid, rhombus, etc.), polygonal, or Various shapes can be selected according to the sticking location, such as a circular shape, an elliptical shape, a semi-circular shape, a triangular shape, a crescent shape, and a shape combining these.
  • the area of the patch (particularly the above-mentioned pharmaceutical portion) can be appropriately determined, and can be, for example, in the range of 2 to 300 cm 2 in consideration of the amount of the active ingredient to be blended in the pressure-sensitive adhesive layer.
  • the pressure-sensitive adhesive layer in the water-containing patch of the present invention contains a) glycol salicylate, b) (meth) alkyl acid alkyl ester copolymer, c) partially neutralized polyacrylic acid, and d) sodium carmellose. It contains a polymer, e) a wetting agent containing glycerin, f) a cross-linking agent, g) hydrochloric acid, and h) water as essential.
  • the water-containing patch of the present invention is generally a non-aqueous acrylic-based adhesive in addition to the hydrophilic acrylic pressure-sensitive adhesive described later, that is, c) a partially neutralized polyacrylic acid, with respect to the water-containing pressure-sensitive adhesive layer.
  • b) (meth) acrylic acid alkyl ester-based copolymer constituting the pressure-sensitive adhesive is also blended.
  • Adhesives generally used for the pressure-sensitive adhesive layer (plaster layer) of water-containing patches include polyacrylic acid, partially neutralized polyacrylic acid, sodium polyacrylate, and N-vinylacetamide / sodium acrylate copolymer. Hydrophilic acrylic pressure-sensitive adhesives such as resins are widely used.
  • the non-water-based pressure-sensitive adhesive to be blended in the water-containing pressure-sensitive adhesive layer of the water-containing patch includes acrylic and methacrylic adhesives.
  • An emulsion-type pressure-sensitive adhesive is preferably blended.
  • the "(meth) acrylic acid alkyl ester-based copolymer” is intended to contain both an acrylic acid and a methacrylic acid alkyl ester, and the "acrylic adhesive” is also an acrylic adhesive. It is intended to contain both agents and methacrylic adhesives.
  • glycol salicylate also referred to as ethylene glycol salicylate
  • non-steroidal anti-inflammatory agents such as fervinac, flurbiprofen, diclofenac, sodium diclofenac, methyl salicylate, indomethacin, ketoprofen, ibuprofen, or esters thereof; diphenhydramine, chlorpheniramine, if necessary.
  • Anti-histamines such as; analgesics such as aspirin, acetaminophen, ibuprofen, sodium loxoprofen; local anesthetics such as lidocaine and diclofenac; muscle relaxants such as schisametonium chloride; antifungal agents such as clotrimazole; antihypertensive agents such as clonidine Vascular dilators such as nitroglycerin and isosorbide nitrate; vitamins such as vitamin A, vitamin E (tocopherol), tocopherol acetate, vitamin K, octothiacin, riboflavine butyrate, prostaglandins; scopolamine, fentanil, capsicum extract, nonyl acid Vanillylamide, capsaicin, dl-camfur and the like may be used in combination.
  • analgesics such as aspirin, acetaminophen, ibuprofen, sodium loxopro
  • the total blending amount of salicylate glycol and other active ingredients can be appropriately determined according to the type of other active ingredients, for example, a water-containing system. Based on the total mass of the pressure-sensitive adhesive layer of the patch, it can be 0.1% by mass or more and 30% by mass or less, or 0.5% by mass or more and 15% by mass or less.
  • the (meth) acrylic acid alkyl ester-based copolymer (non-aqueous adhesive base) constituting the non-aqueous acrylic pressure-sensitive adhesive has a (meth) alkyl ester having 2 to 2 carbon atoms as a component that exhibits adhesive strength. 9 and a monomer that becomes a polymer having a glass transition temperature (Tg) of ⁇ 55 ° C. (218K) or less when homopolymerized, and Tg of 8 to 165 ° C. (Tg) when homopolymerized as a component for improving cohesiveness.
  • Tg glass transition temperature
  • homopolymers obtained by polymerizing only monomers that exhibit adhesive strength are said to have high adhesive strength but weak mechanical strength, and generally, copolymerization with a monomer that improves cohesive strength improves mechanical strength.
  • the coalescence is used as an adhesive.
  • the monomer exhibiting the adhesive strength shown in Table 1 above in the present invention, as a monomer having a higher adhesive strength, acrylic acid having a Tg of 220 K or less when the monomer is homopolymerized (homopolymer). Butyl acrylate, 2-ethylhexyl acrylate, octyl acrylate, isononyl acrylate and the like are used.
  • 2-ethylhexyl acrylate which has been used as a pharmaceutical additive and has high adhesive strength (low Tg of homopolymer), can be preferably used.
  • the monomers that improve the cohesive force include the monomers listed in Table 1. Among them, in the present invention, the mechanical strength is high and the adhesiveness is not significantly reduced (Tg of the homopolymer). Is relatively low), and methyl acrylate is preferred.
  • the blending amount of the (meth) acrylic acid alkyl ester-based copolymer is the total mass of the pressure-sensitive adhesive layer of the water-containing patch.
  • it can be 0.1% by mass or more and 5% by mass or less, 0.5% by mass or more and 4.5% by mass or less, and 1.0% by mass or more and 4.5% by mass or less.
  • the pressure-sensitive adhesive layer of the water-containing patch of the present invention contains a partially neutralized polyacrylic acid as an acrylic-based hydrophilic pressure-sensitive adhesive. Further, if necessary, an acrylic hydrophilic pressure-sensitive adhesive other than the polyacrylic acid partially neutralized product may be blended in the pressure-sensitive adhesive layer.
  • examples of the above-mentioned acrylic hydrophilic pressure-sensitive adhesive include water-soluble (meth) acrylic polymers.
  • the water-soluble (meth) acrylic polymer is a polymer obtained by polymerizing a (meth) acryloyl group-containing monomer having a functional group (hydrophilic group) having water solubility, and is blended with water in the pressure-sensitive adhesive layer.
  • water-soluble (meth) acrylic polymer examples include the above-mentioned partially neutralized product of polyacrylic acid and homopolymers such as polyacrylic acid; and copolymers such as N-vinylacetamide / sodium acrylate copolymer resin.
  • the above-mentioned partially neutralized polyacrylic acid may be a completely neutralized polyacrylic acid, a partially neutralized polyacrylic acid, or a mixture thereof. That is, in the present specification, the "partially neutralized polyacrylic acid” is not only a neutralized product in which a part of the acid groups of polyacrylic acid is neutralized, but also all the acid groups of polyacrylic acid are neutralized. Includes both neutralized products.
  • the polyacrylic acid partially neutralized product means a polyacrylate salt, and for example, sodium salt, potassium salt, calcium salt, ammonium salt and the like can be used. For example, Biscomate NP-800 (manufactured by Showa Denko KK) can be mentioned.
  • the polyacrylic acid partially neutralized product used in the present invention is a partially neutralized product having a neutralization degree of 30% to 65%.
  • a polyacrylic acid partially neutralized product having a viscosity at 20 ° C. of 450 to 650 mPa ⁇ s.
  • the blending amount of the above polyacrylic acid partially neutralized product and the total blending amount of the polyacrylic acid partially neutralized product and the other acrylic hydrophilic pressure-sensitive adhesive when containing other acrylic hydrophilic pressure-sensitive adhesives are water-containing. Based on the total mass of the pressure-sensitive adhesive layer of the patch, for example, it can be 0.1% by mass or more and 10% by mass or less, and 1% by mass or more and 8% by mass or less. For example, the blending amount of the polyacrylic acid partially neutralized product can be 3.5% by mass or more and 4.5% by mass or less based on the total mass of the pressure-sensitive adhesive layer.
  • water-soluble polymer compound As the water-soluble polymer compound, carmellose sodium (sodium carboxymethyl cellulose) is essentially contained in the pressure-sensitive adhesive layer in the patch of the present invention. By using carmellose sodium, the shape-retaining property of the preparation can be further maintained, and the thixotropy property can be obtained to further reduce the pain at the time of peeling.
  • the sodium carmellose used in the present invention can have a viscosity of a 1% by mass aqueous solution thereof at 20 ° C. of 1,000 to 3,000 mPa ⁇ s. Further, the sodium carmellose preferably has a transesterification degree of 0.60 to 0.95.
  • the blending amount of the water-soluble polymer compound is usually 1.0% by mass or more and 30% by mass or less, 2.0% by mass or more and 30% by mass or less, based on the total mass of the pressure-sensitive adhesive layer of the water-containing patch. , 2.5% by mass or more and 20% by mass or less, or 3.0% by mass or more and 10% by mass or less. Further, for example, the blending amount of sodium carmellose can be 2.0% by mass or more and 3.5% by mass or less based on the total mass of the pressure-sensitive adhesive layer.
  • a wetting agent (also referred to as a moisturizer) is blended in the pressure-sensitive adhesive layer of the water-containing patch of the present invention in order to suppress evaporation of water over time.
  • glycerin is indispensably blended in the pressure-sensitive adhesive layer in the patch of the present invention.
  • a wetting agent other than glycerin may be blended, and examples thereof include D-sorbitol, ethylene glycol, propylene glycol, polyethylene glycol, polypropylene glycol, liquid paraffin, 1,3-propanediol, and 1,4-butanediol. , Multihydric alcohols such as martitol and xylitol. These can be used together with glycerin in an appropriate combination of one type or two or more types.
  • the blending amount of the wetting agent is usually, for example, 30% by mass or more and 70% by mass or less, 40% by mass or more and 60% by mass or less, 40% by mass or more and 50% by mass, based on the total mass of the pressure-sensitive adhesive layer of the water-containing patch. It can be in the range of% or less, or 45% by mass or more and 55% by mass or less.
  • the blending amount of glycerin in the pressure-sensitive adhesive layer is more than 15 times and 18 times or less on a mass basis with respect to the blending amount of a) glycol salicylate, for example, 15.5 times or more.
  • cross-linking agent blended in the pressure-sensitive adhesive layer of the water-containing patch of the present invention examples include polyvalent metal salts, and among them, polyvalent metal compounds containing aluminum.
  • hydroxides such as aluminum hydroxide and alumina magnesium hydroxide; aluminum chloride, aluminum sulfate, potassium aluminum sulfate, aluminum glycinate (dihydroxyaluminum aminoacetal), dihydroxyaluminum aminoacetate, synthetic aluminum silicate, dry hydroxide.
  • Positive salts of inorganic or organic acids such as aluminum gel, kaolin and aluminum stearate or basic salts thereof; re-salts such as aluminum myoban; aluminate such as sodium aluminate; inorganic aluminum complex salts and organic aluminum chelate compounds.
  • examples thereof include polyvalent metal compounds such as synthetic hydrotalcite, magnesium aluminate aluminate, and magnesium aluminate metasilicate, and these can be used alone or in combination of two or more.
  • dihydroxyaluminum aminoacetate which is a poorly soluble aluminum compound, synthetic aluminum silicate, and dry aluminum hydroxide gel.
  • the amount of the cross-linking agent to be blended may be appropriately selected in consideration of the degree of cross-linking that may contribute to the residue of the adhesive on the skin and the adhesiveness. Based on the total mass of the pressure-sensitive adhesive layer of the water-containing patch, for example, 0.01% by mass or more and 6.0% by mass or less, 0.01% by mass or more and 4.0% by mass or less, or 0.01% by mass or more. The range of 2.0% by mass or less can be mentioned.
  • Hydrochloric acid is blended in the pressure-sensitive adhesive layer of the water-containing patch of the present invention.
  • the blending amount of hydrochloric acid can be, for example, in the range of 0.1% by mass or more and 1.5% by mass or less based on the total mass of the pressure-sensitive adhesive layer of the water-containing patch. It should be noted that if only other acids such as the acids listed in ⁇ organic acids> described later and inorganic acids other than hydrochloric acid are blended without blending hydrochloric acid, both appropriate crosslinkability and good adhesive strength can be obtained. It gets harder.
  • the water-containing patch of the present invention contains water (moisture) in the pressure-sensitive adhesive layer.
  • the "water” contained in the pressure-sensitive adhesive layer includes not only water separately added as water when the pressure-sensitive adhesive layer is formed, but also water contained in the form of an emulsion or an aqueous solution.
  • the blending amount of water is not particularly limited, but based on the total mass of the pressure-sensitive adhesive layer of the water-containing patch, for example, 10% by mass or more and 90% by mass or less, 15% by mass or more and 70% by mass or less, 20% by mass or more and 50% by mass. It can be in the range of% or less. It should be noted that this water content is a value at the time of preparing the patch or before the patch is applied, and is not limited to the case where water volatilizes from the adhesive layer with the progress of the application.
  • a chelating agent may be added to the pressure-sensitive adhesive layer of the water-containing patch of the present invention in order to control the viscosity of the plaster during production.
  • the chelating agent include sodium edetate (ethylenediaminetetraacetic acid disodium salt).
  • the amount of the chelating agent is usually in the range of 0.01% by mass or more and 1% by mass or less, 0.1% by mass or more and 0.3% by mass or less, based on the total mass of the pressure-sensitive adhesive layer of the water-containing patch. Can be.
  • the pressure-sensitive adhesive layer of the water-containing patch of the present invention assists in dissolving the active ingredient such as a drug (that is, functions as a dissolution aid) and also plays a role of preventing the active ingredient from precipitating from the pressure-sensitive adhesive layer.
  • An organic solvent may be blended as a possible component.
  • organic solvent such as crotamitone; N-methyl-2-pyrrolidone; polyalkylene glycol such as macroglycol 400 (polyethylene glycol) and polybutylene glycol; polyvinyl alcohol; diethyl adipate, diisopropyl adipate, Fatty acid esters such as diethyl sebacate, diisopropyl sebacate, isopropyl myristate, isopropyl palmitate, oleyl oleate; polyoxyalkylene fatty acid esters, etc .; sorbitan esters; polyhydric alcohols such as 1,3-butanediol; dimethylformamide; Examples thereof include dimethyl sulfoxide. These can be used alone or in combination of two or more.
  • the blending amount can be, for example, 0.1% by mass or more and 20% by mass or less based on the total mass of the pressure-sensitive adhesive layer of the water-containing patch.
  • An organic acid may be blended in the pressure-sensitive adhesive layer of the water-containing patch of the present invention.
  • examples of the organic acids that can be blended include tartrate acid, citric acid, lactic acid, gluconic acid, glycolic acid, malic acid, fumaric acid, metasulfonic acid, maleic acid, acetic acid and the like, and these are used alone or in combination of two or more. Can be used in.
  • the blending amount thereof can be, for example, in the range of 0.1% by mass or more and 5% by mass or less based on the total mass of the pressure-sensitive adhesive layer of the water-containing patch.
  • the cross-linking property is insufficient, the problem that the adhesive is dissolved or sticky can be suppressed, and on the other hand, the cross-linking reaction proceeds too much and the plaster becomes hard and cannot be manufactured. Can be expected to be suppressed.
  • a surfactant can also be added to the pressure-sensitive adhesive layer of the water-containing patch of the present invention.
  • surfactants include polyoxy such as polyoxyethylene monolaurate, polyoxyethylene monostearate, polyoxyethylene monooleate, polyethylene glycol distearate, polyethylene glycol dilate, and polypropylene glycol dioleate.
  • Polyethylene fatty acid ester Polyethylene fatty acid ester; sorbitan monocaprylate, sorbitan monolaurate, sorbitan monomillistate, sorbitan monopalmitate, sorbitan monostearate, sorbitan distearate, sorbitan tristearate, sorbitan monoolate, sorbitan triolate, sorbitan monosesqui Solbitan fatty acid esters such as oleate and these ethylene oxide adducts; polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monopalmitate, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan tristearate, polyoxyethylene sorbitan.
  • Polyoxyethylene sorbitan fatty acid esters such as monoolate, polyoxyethylene sorbitan triolate, polyoxyethylene sorbitan triisostearate; polyoxyethylene dodecyl ether (polyoxyethylene lauryl ether), polyoxyalkylene lauryl ether, polyoxyethylene tri Decyl ether, polyoxyalkylene tridecyl ether, polyoxyethylene myristyl ether, polyoxyethylene cetyl ether, polyoxyethylene oleyl ether, polyoxyethylene stearyl ether, polyoxyethylene behenyl ether, polyoxyethylene-2-ethylhexyl ether, poly Polyoxyethylene alkyl ethers such as oxyethylene isodecyl ether; polyoxyethylene alkylphenols such as polyoxyethylene styrene phenyl ethers, polyoxyethylene nonylphenyl ethers, polyoxyethylene distyrene phenyl ethers, and polyoxyethylene tribenzylphenyl
  • glycerin fatty acid esters such as glycerin monostearate and glycerin monooleate
  • nonionic surfactants such as polyethylene glycol, polyoxyethylene hydrogenated castor oil, polyoxyethylene castor oil, and lecithin. These can be used alone or in combination of two or more. When these surfactants are used, the blending amount thereof is, for example, 0.001% by mass or more and 10% by mass or less, 0.01% by mass or more and 5% by mass, based on the total mass of the pressure-sensitive adhesive layer of the water-containing patch. It can be in the following range.
  • an antioxidant such as dibutylhydroxytoluene (BHT), calcium carbonate, magnesium carbonate, silicate, zinc oxide, titanium oxide, magnesium sulfate
  • BHT dibutylhydroxytoluene
  • inorganic powders such as calcium sulfate
  • ultraviolet absorbers such as benzoylmethane derivatives, colorants, fragrances, preservatives, etc.
  • Ingredients that can be generally blended in the agent layer can be blended. When these optional components are used, they are usually 0.01% by mass or more and 1% by mass or less based on the total mass of the pressure-sensitive adhesive layer of the water-containing patch, either individually or in combination of two or more. Can be used in the range.
  • Examples of the support used for the water-containing patch of the present invention include flexible supports such as films, non-woven fabrics, Japanese paper, cotton cloths, knitted cloths, woven cloths, and laminated composites of non-woven fabrics and films. These supports are preferably made of a flexible material that can adhere to the skin and can follow the movement of the skin, and a material that can suppress the occurrence of skin irritation after long-term application.
  • Examples of the material of these supports include polyethylene, polypropylene, polyethylene terephthalate, polybutylene terephthalate, polyethylene naphthalate, polystyrene, nylon, cotton, acetate rayon, rayon, rayon / polyethylene terephthalate composite, polyacrylonitrile, polyvinyl alcohol, and the like.
  • the support such as cloth by coloring the support such as cloth to a color tone such as skin color with a colorant, it is possible to reduce the difference from the skin color at the time of application. Further, in that the color tone of the skin under the application can be easily seen through, a form of a plastic film having excellent transparency can be adopted.
  • the thickness of the support is usually about 5 ⁇ m to 1 mm.
  • its thickness is preferably 50 ⁇ m to 1 mm, more preferably 100 to 800 ⁇ m, and further preferably 200 to 700 ⁇ m.
  • the support is a plastic film, its thickness is preferably 10 to 300 ⁇ m, more preferably 12 to 200 ⁇ m, and even more preferably 15 to 150 ⁇ m.
  • the thickness of the support is as thin as about 5 ⁇ m to 30 ⁇ m, if a peelable carrier film layer is provided on the surface opposite to the pressure-sensitive adhesive layer formed on the support, the handleability as a patch can be improved. It is preferable because it improves.
  • the thickness of the support is smaller than 5 ⁇ m, the strength and handleability of the patch will decrease, making it difficult to stick to the skin, tearing due to contact with other members, or contact with water for bathing, etc. Contact may cause it to peel off the skin in a short time.
  • the thickness of the support is too large (more than 1 mm), it becomes difficult for the patch to follow the movement of the skin, and it becomes easy to form a trigger for peeling off at the edge of the patch, so that the patch can be peeled off from the skin in a short time. There is a risk of peeling or an increase in discomfort during sticking.
  • one or both sides of the support may be sandblasted, corona-treated, or the like for the purpose of improving the anchoring property of the adhesive and the support. Further, in order to facilitate removal from the packaging material, unevenness may be provided on one side or both sides of the support by a method other than sandblasting.
  • the release liner (also referred to as release layer / release paper) used in the water-containing patch of the present invention is preferably made of a material that does not easily absorb or adsorb drugs or the like in the pressure-sensitive adhesive layer, and is commonly used in the technical field of patches. Can be used.
  • plastic films such as polyester (polyethylene terephthalate, polybutylene terephthalate, polyethylene naphthalate, etc.), polypropylene (non-stretched, stretched, etc.), polyethylene, polyurethane, polyvinyl chloride, polystyrene, etc .; high-quality paper, glassin paper, parchment paper, craft Paper such as paper and synthetic paper; peeling processed paper in which the plastic film, paper or synthetic paper, synthetic fiber and the like are coated with a release agent having peeling performance such as silicone resin and fluororesin; aluminum foil; various films and sheets are used. Examples thereof include colorless or colored sheets such as laminated laminated paper and laminated peeled paper obtained by coating the laminated paper with a release agent.
  • the release liner can also be provided with irregularities so that it can be easily taken out from the packaging material.
  • the thickness of these release liners is not particularly limited, but is usually in the range of 10 ⁇ m to 1 mm, for example, 20 ⁇ m to 500 ⁇ m, preferably 40 ⁇ m to 200 ⁇ m.
  • the peeling force when peeling the pressure-sensitive adhesive layer from the peeling liner is preferably a peeling force within a specific range. This is because if the peeling force of the adhesive layer from the release liner is too weak, the adhesive layer (that is, the adhesive) will be released from the release liner if the adhesive is caught in the packaging material when the adhesive in the packaging material is taken out. This is because there is a risk of slipping and peeling.
  • the peeling force of the pressure-sensitive adhesive layer (adhesive) from the release liner can be, for example, 0.01 N / 15 mm to 0.5 N / 15 mm, although it depends on the type of the peeling liner used.
  • the water-containing patch of the present invention can be produced by using a conventionally known method. For example, it can be manufactured through the following steps (i) or (ii).
  • the thickness of the pressure-sensitive adhesive layer is not particularly limited, but is usually 10 ⁇ m to 1000 ⁇ m, for example, about 20 ⁇ m to 800 ⁇ m.
  • the pressure-sensitive adhesive layer-forming composition includes various components contained in the above-mentioned pressure-sensitive adhesive layer: glycol salicylate (other active ingredients), (meth) acrylic acid alkyl ester-based copolymer, and polyacrylic acid partially neutralized product (polyacrylic acid partially neutralized product). Others, acrylic hydrophilic adhesive), water-soluble polymer compound containing carmellose sodium, wetting agent containing glycerin, cross-linking agent, hydrochloric acid, and water, and if desired, chelating agent, organic solvent, organic acid, A semi-solid composition that can contain a surfactant and even any other component.
  • the pressure-sensitive adhesive layer-forming composition has a viscosity of 90 to 250 Pa ⁇ s, 100 to 250 Pa ⁇ s, and more preferably 130 to 250 Pa ⁇ s at 20 ° C. to 30 ° C. from the viewpoint of operability during production. Is preferable. If the viscosity is less than 90 Pa ⁇ s, the plaster may strike through when a knitted fabric or a woven fabric is used as a support. If the viscosity exceeds 250 Pa ⁇ s, it becomes difficult to spread.
  • the pH value of the pressure-sensitive adhesive layer is preferably on the acidic side (less than 6.0), preferably 3.5 or more and less than 6.0, for example, 4.00 to 4.85. Can be 4.40 to 4.80, more preferably 4.50 to 4.80.
  • the pH value of the pressure-sensitive adhesive layer can be measured at a temperature of 20 to 25 ° C., for example, according to the pH measurement method of the Japanese Pharmacopoeia general test method.
  • the pH value of the solution obtained by diluting the pressure-sensitive adhesive (plaster) in water may be treated as the pH value of the pressure-sensitive adhesive layer (for example, International Publication No. 2016/10226).
  • the release liner is peeled off from the prepared adhesive, the adhesive is scraped off from the exposed adhesive layer using a spatula or the like, purified water is added to the collected adhesive, and for example, 20-fold dilution is performed.
  • the obtained solution is kept warm at room temperature (25.0 ⁇ 0.2 ° C.), a glass composite electrode of a calibrated pH meter is inserted into the solution, and the pH value is measured.
  • the pressure-sensitive adhesive layer (adhesive layer-forming composition) of the present invention is a pressure-sensitive adhesive layer after being immersed and allowed to stand for 24 hours with respect to the weight of the pressure-sensitive adhesive layer before being immersed and allowed to stand when it is immersed in purified water for 24 hours.
  • the degree of swelling of the pressure-sensitive adhesive layer calculated as a ratio of the weight of the pressure-sensitive adhesive layer is preferably less than 50.
  • the procedure for measuring and calculating the degree of swelling is as follows, for example: The water-containing patch and the support are cut to a predetermined size, and the weight of the water-containing patch is weighed with the liner peeled off. Measure each (initial water-containing patch (liner peeling) weight, initial support weight).
  • the weights after being immersed and allowed to stand for 24 hours are measured (weight of water-containing patch (liner peeling) after standing in purified water, support after standing in purified water).
  • Body weight the degree of swelling can be calculated according to the following formula.
  • Degree of swelling of the pressure-sensitive adhesive layer (weight of water-containing patch (liner peeling) after standing in purified water-weight of support after standing in purified water) / (weight of initial water-containing patch (liner peeling) -initial support weight)
  • Example 1 1.5 parts by mass of polyvinyl alcohol was dissolved in purified water (aqueous phase). Next, 1 part by mass of Macrogol 400 was added to 1.25 parts by mass of ethylene glycol salicylate and 1 part by mass of L-menthol and dissolved (oil phase). Further, 4 parts by mass of a partially neutralized polyacrylic acid (when an aqueous solution having a neutralization degree of 35% and a viscosity of 0.2% by mass has a viscosity of 547 mPa ⁇ s at 20 ° C.), sodium carmellose (ester). Substitution degree: 0.82, viscosity: 1% by mass The viscosity of the aqueous solution at 20 ° C.
  • Example 4 viscosity of the pressure-sensitive adhesive described later was carried out using the obtained pressure-sensitive adhesive layer forming composition.
  • the obtained pressure-sensitive adhesive layer-forming composition was spread on the silicone surface of a liner (one-sided silicone-treated PET (75 ⁇ m)) with a spreading machine, and a knit support (made of polyester) was laminated, and then 1 at 40 ° C. Aged for a week. After aging, it was punched into an arbitrary shape to obtain the formulation of Example 1.
  • Examples 2 to 9, Comparative Examples 1 to 9 The formulations of Examples 2 to 9 and Comparative Examples 1 to 9 were obtained in the same manner as in Example 1 except that the type and blending amount of each component were changed as described in Tables 2 and 3. .. When phosphoric acid and tartaric acid were blended, they were produced by adding them at the same timing as hydrochloric acid.
  • Test Example 1 pH measurement of adhesive layer
  • the pH of each product was measured at 25.0 ⁇ 0.2 ° C. according to the pH measurement method of the Japanese Pharmacopoeia general test method. The obtained results are shown in Tables 2 and 3.
  • Test Example 2 Evaluation of Stability of Glycol Salicylate (SG) The stability of glycol salicylate is evaluated immediately after the preparation of the preparation (initial stage) and after storage at 60 ° C. for 2 weeks (2W) for the glycol salicylate contained in the pressure-sensitive adhesive layer. The content was measured by high performance liquid chromatography (HPLC) method. Specifically, each preparation was cut into 40 mm ⁇ 40 mm (16 cm 2 ), the release liner was peeled off, and gauze (medical gauze, type I, 50 mm ⁇ 50 mm) was attached to the adhesive layer, and this was used as a test preparation. 27 mL of methanol was used as the extraction solvent, a test preparation was added thereto, and the extraction operation was performed by shaking.
  • HPLC high performance liquid chromatography
  • the extract was filtered through a membrane filter having a pore size of 0.45 ⁇ m to prepare a sample solution.
  • the sample solution was analyzed under the following HPLC conditions. Stability of glycol salicylate (residual% in adhesive layer) by comparing the relative amount of decomposition products from the sum of the peak area of glycol salicylate (retention time: about 11 minutes) and the area of other peaks. was evaluated. Further, from the initial value (residual% of glycol salicylate in the pressure-sensitive adhesive layer before storage), the amount of decrease in glycol salicylate after storage at 60 ° C. for 2 weeks (2 W) (relative to the initial value reduction amount (%)) was calculated. .. The obtained results are shown in Tables 2 and 3.
  • Test Example 4 Viscosity of Adhesive
  • the viscosity of the adhesive layer forming composition produced in the procedure of ⁇ Preparation of Adhesive> was measured with a handy rotational viscometer before liner coating (measurement temperature 20 ° C to 30 ° C.). °C). The obtained results are shown in Tables 2 and 3.
  • Test Example 5 Adhesive layer degree of cross-linking
  • the preparation and the support are cut into 12 x 100 mm, and the weight of the preparation is measured (initial preparation weight, initial support weight) with the liner peeled off, and purified water is added.
  • the mixture was allowed to stand in the glass bottle (room temperature) for 24 hours.
  • the preparation and the support are taken out from purified water and weighed (the weight of the preparation after standing in purified water, the weight of the support after standing in purified water), and the degree of swelling of the plaster (adhesive layer) is determined. Calculated from the following formula.
  • Degree of swelling of plaster (weight of product after standing in purified water-weight of support after standing in purified water) / (weight of initial product-weight of initial support) Based on the calculated swelling degree, the degree of cross-linking was evaluated according to the following evaluation criteria. The obtained results are shown in Tables 2 and 3.
  • the degree of cross-linking is preferably + or higher, and if it is ⁇ or-, the shape-retaining property of the plaster is insufficient, and a large amount of plaster may remain on the skin when peeled off after application.
  • Test Example 6 Manufacturability
  • the adhesive layer forming composition produced in the procedure of ⁇ Preparation of patch> is produced according to the following evaluation criteria regarding the difficulty of spreading the adhesive layer forming composition on the silicone surface of the liner with a spreading machine. Gender was evaluated. The obtained results are shown in Tables 2 and 3.
  • the prepared product (hydrous-containing patch) of the example contains a predetermined amount of hydrochloric acid to evaluate the stability of glycol salicylate, which is an active ingredient, with respect to the initial value after storage at 60 ° C. for 2 weeks.
  • the amount of decrease is less than 5%
  • the ball tack value is 15 or more
  • the swelling degree which is an index of the degree of cross-linking of the adhesive layer (plaster)
  • the stability of the active ingredient It became a water-containing patch with good adhesive strength and degree of cross-linking of the preparation.
  • the active ingredient in a water-containing patch containing glycol salicylate in the pressure-sensitive adhesive layer, by blending hydrochloric acid in the pressure-sensitive adhesive layer, the active ingredient can be blended even in a small amount. It was confirmed that the glycol salicylate, which is stable over time, has an appropriate degree of cross-linking and good adhesive strength, and can provide a water-containing patch having excellent manufacturability.

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Abstract

Le problème décrit par la présente invention est de fournir un patch contenant de l'eau dans lequel la stabilité du salicylate de glycol et la force adhésive ainsi que le degré de réticulation d'une préparation sont améliorés. La solution selon l'invention porte sur un patch contenant de l'eau qui comprend : un corps de support ; une couche adhésive disposée sur le corps de support ; et un film protecteur fixé sur la couche adhésive, la couche adhésive contenant a) du salicylate de glycol, b) un copolymère d'ester alkylique et d'acide (méth)acrylique, c) un produit partiellement neutralisé d'acide polyacrylique, d) un composé polymère hydrosoluble contenant de la carmellose sodique, e) un hydratant contenant de la glycérine, f) un agent de réticulation, g) un acide chlorhydrique et h) de l'eau, et la quantité de glycérine ajoutée dans la couche adhésive est de 15 fois à 18 fois (à l'exclusion de 15) supérieure, en masse, à la quantité ajoutée de salicylate de glycol.
PCT/JP2020/036894 2020-03-27 2020-09-29 Patch WO2021192366A1 (fr)

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PCT/JP2021/012730 WO2021193874A1 (fr) 2020-03-27 2021-03-25 Timbre transdermique
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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS61151131A (ja) * 1984-12-25 1986-07-09 Lion Corp 外用製剤
JP2007039451A (ja) * 2005-07-07 2007-02-15 Saitama Daiichi Seiyaku Kk 含水系粘着剤組成物及びそれを用いた貼付剤
WO2015025935A1 (fr) * 2013-08-23 2015-02-26 久光製薬株式会社 Cataplasme et son procédé de production
WO2016104226A1 (fr) * 2014-12-22 2016-06-30 久光製薬株式会社 Cataplasme

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS61151131A (ja) * 1984-12-25 1986-07-09 Lion Corp 外用製剤
JP2007039451A (ja) * 2005-07-07 2007-02-15 Saitama Daiichi Seiyaku Kk 含水系粘着剤組成物及びそれを用いた貼付剤
WO2015025935A1 (fr) * 2013-08-23 2015-02-26 久光製薬株式会社 Cataplasme et son procédé de production
WO2016104226A1 (fr) * 2014-12-22 2016-06-30 久光製薬株式会社 Cataplasme

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