JP4567320B2 - Antibacterial adhesive products - Google Patents
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Description
本発明は、粘着テープ、例えば粘着ラベル、粘着シート、絆創膏、手術用ドレープや医療器具の包装材などの医療用粘着製品に用いるに適した抗菌性粘着製品に関する。 The present invention relates to an antibacterial pressure-sensitive adhesive product suitable for use in a pressure-sensitive adhesive tape, for example, a pressure-sensitive adhesive label, a pressure-sensitive adhesive sheet, an adhesive bandage, a surgical drape or a packaging material for medical equipment.
粘着テープなどの粘着製品を皮膚に貼付した場合、貼付部位は密封され、蒸れも生じるため、非常に細菌感染を起こしやすい。 When an adhesive product such as an adhesive tape is affixed to the skin, the application site is sealed and stuffy also occurs, so that bacterial infection is very likely to occur.
また、ざ瘡（にきび）の治療用粘着製品に、殺菌剤としてヨウ素を配合することが知られている（特許文献１）。 In addition, it is known that iodine is blended as an antibacterial agent in an adhesive product for treating acne (Patent Document 1).
しかしながら、ヨウ素自身は常温においても揮発しやすく、持続性、安定性、臭いの点で問題がある。 However, iodine itself tends to volatilize at room temperature, and there are problems in terms of sustainability, stability, and odor.
一方、ヨウ素の包接化物であるヨウ素−シクロデキストリン包接化物が知られているが（特許文献２、３）、粘着製品に適用された例はなく、粘着剤中に配合した場合に、ヨウ素が本来有する抗菌作用を有効に発揮できるか不明であった。 On the other hand, an iodine-cyclodextrin inclusion product that is an inclusion product of iodine is known (Patent Documents 2 and 3), but there is no example applied to an adhesive product. It was unclear whether the antibacterial action inherently could be effectively exhibited.
本発明は、ヨウ素が本来有する抗菌作用を有効に発揮できる粘着製品を提供することを目的とする。 An object of this invention is to provide the adhesive product which can exhibit the antibacterial action which iodine originally has.
本発明は、以下の発明を包含する。
（１）粘着剤層中にヨウ素−シクロデキストリン包接化物を含有する粘着製品。
（２）粘着剤層が多価アルコールを含有する前記（１）に記載の粘着製品。
（３）多価アルコールがエチレングリコール又はプロピレングリコールである前記（２）に記載の粘着製品。
（４）粘着剤層中の粘着剤がアクリル系粘着剤である前記（１）〜（３）のいずれかに記載の粘着製品。
（５）医療用途に用いる前記（１）〜（４）のいずれかに記載の粘着製品。
The present invention includes the following inventions.
(1) An adhesive product containing an iodine-cyclodextrin inclusion product in the adhesive layer.
(2) The pressure-sensitive adhesive product according to (1), wherein the pressure-sensitive adhesive layer contains a polyhydric alcohol.
(3) The pressure-sensitive adhesive product according to (2), wherein the polyhydric alcohol is ethylene glycol or propylene glycol.
(4) The adhesive product according to any one of (1) to (3), wherein the adhesive in the adhesive layer is an acrylic adhesive.
(5) The pressure-sensitive adhesive product according to any one of (1) to (4), which is used for medical purposes.
本発明によれば、ヨウ素が本来有する抗菌作用を有効に発揮できる粘着製品を提供することができる。 ADVANTAGE OF THE INVENTION According to this invention, the adhesive product which can exhibit the antibacterial action which iodine originally has can be provided.
本発明に用いるヨウ素−シクロデキストリン包接化物としては、特に制限はなく、粉末状、顆粒状等いずれの形態でもよい。また、ヨウ素−シクロデキストリン包接化物中のヨウ素含量は、特に制限はないが、通常５〜３５質量％、好ましくは５〜３０質量％、更に好ましくは１９〜２５質量％である。 There is no restriction | limiting in particular as an iodine-cyclodextrin inclusion product used for this invention, Any forms, such as a powder form and a granular form, may be sufficient. Moreover, the iodine content in the iodine-cyclodextrin inclusion product is not particularly limited, but is usually 5 to 35% by mass, preferably 5 to 30% by mass, and more preferably 19 to 25% by mass.
ヨウ素−シクロデキストリン包接化物の調製に用いるヨウ素は、特に制限されるものではなく、市販品をそのまま使用してもよい。 The iodine used for preparing the iodine-cyclodextrin inclusion product is not particularly limited, and a commercially available product may be used as it is.
また、ヨウ素−シクロデキストリン包接化物の調製に用いるシクロデキストリンもまた、特に制限されるものではなく、市販品をそのまま使用しても、又はデンプンにBacillus macerans由来のアミラーゼを作用させることなどの公知の方法によって製造してもよい。なお、本明細書において、「シクロデキストリン」は、それぞれ６、７及び８個の環状α−（１→４）結合したＤ−グルコピラノース単位から構成されるα−、β−及びγ−シクロデキストリンを包含するのみならず、例えば、メチル体、プロピル体、モノアセチル体、トリアセチル体及びモノクロロトリアジニル体等の、シクロデキストリンの化学修飾体をも包含するものである。シクロデキストリンの市販品の具体例としては、CAVAMAX W6及びCAVAMAX W6 Pharma（いずれも、ワッカーケミカルズ・イーストアジア株式会社製）として市販されるα−シクロデキストリン；CAVAMAX W7及びCAVAMAX W7 PHARMA（いずれも、ワッカーケミカルズ・イーストアジア株式会社製）として市販されるβ−シクロデキストリン；CAVAMAX W8、CAVAMAX W8 Food及びCAVAMAX W8 Pharma（いずれも、ワッカーケミカルズ・イーストアジア株式会社製）として市販されるγ−シクロデキストリン；CAVASOL W7 M、CAVASOLW7 M Pharma及びCAVASOL W7 M TL（いずれも、ワッカーケミカルズ・イーストアジア株式会社製）として市販されるメチル−β−シクロデキストリン；CAVASOLW7 HP及びCAVASOL W7 HP Pharma（いずれも、ワッカーケミカルズ・イーストアジア株式会社製）として市販されるヒドロキシプロピル−β−シクロデキストリン；CAVASOL W7 A（いずれも、ワッカーケミカルズ・イーストアジア株式会社製）として市販されるモノアセチル−β−シクロデキストリン；CAVASOL W7 TA（いずれも、ワッカーケミカルズ・イーストアジア株式会社製）として市販されるトリアセチル−β−シクロデキストリン；ならびにCAVASOL W7 MCT（いずれも、ワッカーケミカルズ・イーストアジア株式会社製）として市販されるモノクロロトリアジニル−β−シクロデキストリンなどが挙げられる。これらのうち、安全性などを考慮すると、食品添加物として認可されるβ−シクロデキストリン及びγ−シクロデキストリンならびにこれらの化学修飾体が好ましく使用され、特にヨウ素−シクロデキストリン包接化物内へのヨウ素の包接量の調整が容易である点を考慮すると、β−シクロデキストリン及びこの化学修飾体がシクロデキストリンとして最も好ましく使用される。 In addition, the cyclodextrin used for the preparation of the inclusion product of iodine-cyclodextrin is not particularly limited, and a known product such as a commercially available product can be used as it is or an amylase derived from Bacillus macerans is allowed to act on starch. You may manufacture by the method of. In the present specification, “cyclodextrin” means α-, β-, and γ-cyclodextrin composed of 6, 7 and 8 cyclic α- (1 → 4) linked D-glucopyranose units, respectively. In addition, for example, cyclodextrin chemical modifications such as methyl, propyl, monoacetyl, triacetyl, and monochlorotriazinyl are also included. Specific examples of commercially available cyclodextrin products include α-cyclodextrin marketed as CAVAMAX W6 and CAVAMAX W6 Pharma (both manufactured by Wacker Chemicals East Asia Co., Ltd.); CAVAMAX W7 and CAVAMAX W7 PHARMA (both Wacker Β-cyclodextrin marketed as Chemicals East Asia Co.); γ-cyclodextrin marketed as CAVAMAX W8, CAVAMAX W8 Food and CAVAMAX W8 Pharma (all manufactured by Wacker Chemicals East Asia Co., Ltd.); CAVASOL Methyl-β-cyclodextrin marketed as W7 M, CAVASOLW7 M Pharma and CAVASOL W7 M TL (all manufactured by Wacker Chemicals East Asia Co., Ltd.); CAVASOLW7 HP and CAVASOL W7 HP Pharma (all manufactured by Wacker Chemicals East Hydroxyp commercially available as Asia) Lopyr-β-cyclodextrin; monoacetyl-β-cyclodextrin marketed as CAVASOL W7 A (both manufactured by Wacker Chemicals East Asia Co., Ltd.); CAVASOL W7 TA (all manufactured by Wacker Chemicals East Asia Co., Ltd.) And trichloro-β-cyclodextrin commercially available as CAVASOL W7 MCT (all manufactured by Wacker Chemicals East Asia Co., Ltd.) and monochlorotriazinyl-β-cyclodextrin. Of these, β-cyclodextrin and γ-cyclodextrin which are approved as food additives and chemical modifications thereof are preferably used in consideration of safety and the like, and iodine in the inclusion product of iodine-cyclodextrin is particularly preferable. In view of easy adjustment of the amount of inclusion, β-cyclodextrin and this chemical modification are most preferably used as cyclodextrin.
ヨウ素−シクロデキストリン包接化物の製法等は、例えば特開昭５１−８８６２５号公報、特開２００２−３７０９０２号公報に詳細に記載されている。 The production method of the iodine-cyclodextrin inclusion product is described in detail in, for example, JP-A Nos. 51-88625 and 2002-370902.
なお、ヨウ素−シクロデキストリン包接化物としては、例えば、β−シクロデキストリンとヨウ素との包接体（有効ヨウ素２０質量％含有品）の粉末が、「ＢＣＤＩ（２０％）」の製品名（販売元：純正化学株式会社、製造元：日宝化学株式会社）で市販されているので、これらの市販品を用いてもよい。 As an inclusion product of iodine-cyclodextrin, for example, a powder of inclusion body of β-cyclodextrin and iodine (containing 20% by mass of effective iodine) is a product name of “BCDI (20%)” (sales Original: Pure Chemical Co., Ltd., Manufacturer: Niho Chemical Co., Ltd.), these commercial products may be used.
ヨウ素−シクロデキストリン包接化物の配合量は、粘着剤（固形分）１００質量部に対して、通常１質量部以上２５質量部以下、好ましくは３質量部以上１５質量部以下である。 The compounding amount of the iodine-cyclodextrin inclusion product is usually 1 part by mass or more and 25 parts by mass or less, preferably 3 parts by mass or more and 15 parts by mass or less with respect to 100 parts by mass of the pressure-sensitive adhesive (solid content).
本発明において、粘着剤層の形成に用いる粘着剤としては、特に制限はなく、例えばアクリル系粘着剤、ゴム系粘着剤、シリコーン系粘着剤、ウレタン系粘着剤、好ましくはアクリル系粘着剤が挙げられる。 In the present invention, the pressure-sensitive adhesive used for forming the pressure-sensitive adhesive layer is not particularly limited, and examples thereof include acrylic pressure-sensitive adhesives, rubber-based pressure-sensitive adhesives, silicone-based pressure-sensitive adhesives, urethane-based pressure-sensitive adhesives, and preferably acrylic pressure-sensitive adhesives. It is done.
粘着剤としてアクリル系粘着剤を用いる場合、アクリル系重合体の原料単量体の主成分として用いられる（メタ）アクリル酸アルキルエステルとしては、特に制限はないが、通常、エステル基を構成するアルキル基が炭素数１〜１８のアルキル基である各種のアクリル酸アルキルエステル又はメタクリル酸アルキルエステルを使用でき、具体的にはアクリル酸メチル、アクリル酸エチル、アクリル酸プロピル、アクリル酸ｎ−ブチル、アクリル酸イソブチル、アクリル酸２−エチルヘキシル、アクリル酸イソオクチル、メタクリル酸メチル、メタクリル酸エチル、メタクリル酸プロピル、メタクリル酸ｎ−ブチル、メタクリル酸イソブチル、メタクリル酸２−エチルヘキシル、メタクリル酸イソオクチル等を挙げることができる。 When an acrylic pressure-sensitive adhesive is used as the pressure-sensitive adhesive, there is no particular limitation on the (meth) acrylic acid alkyl ester used as the main component of the raw material monomer of the acrylic polymer, but usually the alkyl constituting the ester group Various acrylic acid alkyl ester or methacrylic acid alkyl ester whose group is an alkyl group having 1 to 18 carbon atoms can be used. Specifically, methyl acrylate, ethyl acrylate, propyl acrylate, n-butyl acrylate, acrylic Examples include isobutyl acid, 2-ethylhexyl acrylate, isooctyl acrylate, methyl methacrylate, ethyl methacrylate, propyl methacrylate, n-butyl methacrylate, isobutyl methacrylate, 2-ethylhexyl methacrylate, and isooctyl methacrylate. .
また、アクリル系重合体を構成する単量体としては、前記（メタ）アクリル酸アルキルエステルを単独で又は２種以上組み合わせて用いてもよいし、更に共重合可能な他の単量体を併用してもよい。共重合可能な他の単量体としては、酢酸ビニル、スチレン、アクリロニトリル、アクリルアミド、ジメチルアクリルアミド、アクリル酸、メタクリル酸、アクリル酸２−ヒドロキシエチル、メタクリル酸グリシジル、アクリル酸４−ヒドロキシブチル、Ｎ−ビニルピロリドン等のアクリル系粘着剤の改質用単量体として知られる各種の単量体をいずれも使用可能である。 Moreover, as a monomer which comprises an acryl-type polymer, you may use the said (meth) acrylic-acid alkylester individually or in combination of 2 or more types, and also uses the other monomer which can be copolymerized further together. May be. Examples of other copolymerizable monomers include vinyl acetate, styrene, acrylonitrile, acrylamide, dimethylacrylamide, acrylic acid, methacrylic acid, 2-hydroxyethyl acrylate, glycidyl methacrylate, 4-hydroxybutyl acrylate, N- Any of various monomers known as monomers for modifying acrylic adhesives such as vinylpyrrolidone can be used.
これらの単量体の重合は、溶液重合、エマルジヨン重合、塊状重合等の通常の重合方法によって行われる。重合の反応温度は、通常５０〜８５℃、好ましくは６０〜８０℃である。 Polymerization of these monomers is performed by a usual polymerization method such as solution polymerization, emulsion polymerization, bulk polymerization and the like. The reaction temperature of the polymerization is usually 50 to 85 ° C, preferably 60 to 80 ° C.
溶液重合を行う場合には、アセトン、ベンゼン、トルエン、酢酸エチル、ヘキサン、ヘプタン、メタノール、エタノール、イソプロパノール等の溶媒中で、固形分濃度通常０．５〜６０質量％、好ましくは５〜５０質量％で、アゾビスイソブチロニトリル、ベンゾイルペルオキシド等の重合開始剤を用いて行われる。 In the case of performing solution polymerization, in a solvent such as acetone, benzene, toluene, ethyl acetate, hexane, heptane, methanol, ethanol, isopropanol or the like, the solid content concentration is usually 0.5 to 60% by mass, preferably 5 to 50% by mass. % Using a polymerization initiator such as azobisisobutyronitrile, benzoyl peroxide.
重合開始剤の配合量（固形分）は、アクリル系重合体（固形分）１００質量部に対して、通常０．０５〜１質量部である。 The compounding quantity (solid content) of a polymerization initiator is 0.05-1 mass part normally with respect to 100 mass parts of acrylic polymers (solid content).
前記アクリル系粘着剤には、ヘキサメチレンジイソシアナート、トルイジンジイソシアナート等のイソシアナート化合物；１，３−ビス（Ｎ，Ｎ−ジグリシジルアミノメチル）トルエン、Ｎ，Ｎ，Ｎ´，Ｎ´−テトラグリシジル−４，４´−ジアミノジフェニルメタン等のエポキシ化合物；トリスエチルアセトアセテートアルミニウム、エチルアセトアセテートアルミニウムジイソプロピレート等の金属キレート化合物；Ｎ，Ｎ´−トルエン−２，４−ビス（１−アジリジンカルボキシアミド）トリエチレンメラミン、ヘキサメチレンジエチレン尿素等のイミン化合物などの架橋剤（硬化剤）を添加することもできる。 Examples of the acrylic pressure-sensitive adhesive include isocyanate compounds such as hexamethylene diisocyanate and toluidine diisocyanate; 1,3-bis (N, N-diglycidylaminomethyl) toluene, N, N, N ′, N ′ -Epoxy compounds such as tetraglycidyl-4,4'-diaminodiphenylmethane; metal chelate compounds such as trisethylacetoacetate aluminum and ethylacetoacetate aluminum diisopropylate; N, N'-toluene-2,4-bis (1- Cross-linking agents (curing agents) such as imine compounds such as (aziridinecarboxamide) triethylenemelamine and hexamethylenediethyleneurea can also be added.
架橋剤の配合量（固形分）は、アクリル系重合体（固形分）１００質量部に対して、通常０．０５〜５質量部、好ましくは０．１〜３質量部である。 The compounding amount (solid content) of the crosslinking agent is usually 0.05 to 5 parts by mass, preferably 0.1 to 3 parts by mass with respect to 100 parts by mass of the acrylic polymer (solid content).
本発明の粘着製品においては、粘着剤層に多価アルコールを配合することにより、ヨウ素−シクロデキストリン包接化物が粘着剤中に均一に含まれることにより平滑な粘着剤面が得られ、ヨウ素含有率の高い粘着製品を得ることができる。前記多価アルコールとしては、例えばエチレングリコール、プロピレングリコール、ブチレングリコール、グリセリン、好ましくはエチレングリコール又はプロピレングリコールが挙げられる。 In the pressure-sensitive adhesive product of the present invention, by blending polyhydric alcohol in the pressure-sensitive adhesive layer, a smooth pressure-sensitive adhesive surface is obtained when the iodine-cyclodextrin inclusion product is uniformly contained in the pressure-sensitive adhesive, and contains iodine. An adhesive product with a high rate can be obtained. Examples of the polyhydric alcohol include ethylene glycol, propylene glycol, butylene glycol, glycerin, preferably ethylene glycol or propylene glycol.
多価アルコールの配合量は、ヨウ素−シクロデキストリン包接化物１００質量部に対して、好ましくは１００〜１０００質量部、更に好ましくは２００〜６００質量部である。 The blending amount of the polyhydric alcohol is preferably 100 to 1000 parts by mass, more preferably 200 to 600 parts by mass with respect to 100 parts by mass of the iodine-cyclodextrin inclusion product.
粘着剤層には、前記粘着剤のほか、必要に応じて、ロジン系樹脂（水素化ロジンエステルなど）、テルペン系樹脂、芳香族炭化水素樹脂、脂肪族炭化水素樹脂、石油樹脂、エステルガム、油脂性フェノール樹脂等の粘着付与剤、ミリスチン酸イソプロピル、オレイン酸オレイル、プロセスオイル、ポリイソブチレン、ポリブテン、流動パラフィン、スクワレン、シリコーン油、オリーブ油、大豆油、ナタネ油、ヤシ油、牛脂等の軟化剤；カオリン、タルク、ベントナイト、酸化チタン、酸化亜鉛、炭酸カルシウム、リン酸カルシウム、炭酸水素カルシウム、硫酸アルミニウム、無水ケイ酸、シリカ、メタケイ酸アルミニウム、アルミナ等の充填剤；ＢＨＴ、ＢＨＡ、グアヤコールエステル、ノルジヒドログアヤレチック酸等の酸化防止剤を含有させてもよい。 In the adhesive layer, in addition to the above-mentioned adhesive, rosin resin (hydrogenated rosin ester, etc.), terpene resin, aromatic hydrocarbon resin, aliphatic hydrocarbon resin, petroleum resin, ester gum, Tackifiers such as oily phenol resins, softeners such as isopropyl myristate, oleyl oleate, process oil, polyisobutylene, polybutene, liquid paraffin, squalene, silicone oil, olive oil, soybean oil, rapeseed oil, coconut oil, beef tallow Fillers such as kaolin, talc, bentonite, titanium oxide, zinc oxide, calcium carbonate, calcium phosphate, calcium hydrogen carbonate, aluminum sulfate, anhydrous silicic acid, silica, aluminum metasilicate, alumina, etc .; BHT, BHA, guaiacol ester, nordihydro Contains antioxidants such as guaiaretic acid It may be.
本発明の粘着製品は、粘着テープ、粘着ラベル、粘着シート、絆創膏、手術用ドレープや医療器具の包装材などの医療用粘着製品等を含むものであり、支持体又は剥離シート上に前記の粘着剤組成物を塗布し、粘着剤層を形成することにより得ることができる。 The pressure-sensitive adhesive product of the present invention includes a pressure-sensitive adhesive tape, a pressure-sensitive adhesive label, a pressure-sensitive adhesive sheet, an adhesive bandage, a surgical drape, a medical pressure-sensitive adhesive product such as a packaging material for medical equipment, and the like. It can be obtained by applying an adhesive composition to form an adhesive layer.
本発明の粘着製品における粘着剤層の塗布量は、通常５〜２００ｇ／ｍ２、好ましくは１０〜１００ｇ／ｍ２である。 The application amount of the pressure-sensitive adhesive layer in the pressure-sensitive adhesive product of the present invention is usually 5 to 200 g / m 2 , preferably 10 to 100 g / m 2 .
本発明の粘着製品の粘着剤層は支持体上に設けられる場合が多い。当該支持体としては、特に制限はなく、例えば、ポリエステル（例えば、ポリエチレンテレフタレート）、ポリエチレン、ポリプロピレン、ポリ塩化ビニル、ポリカーボネート、エチレン・酢酸ビニル共重合体、ポリウレタン、ポリスチレン、ポリイミド等の樹脂フィルムや、紙、合成紙、布、金属箔などが挙げられる。 The pressure-sensitive adhesive layer of the pressure-sensitive adhesive product of the present invention is often provided on a support. The support is not particularly limited. For example, polyester (for example, polyethylene terephthalate), polyethylene, polypropylene, polyvinyl chloride, polycarbonate, ethylene / vinyl acetate copolymer, polyurethane, polystyrene, polyimide, or other resin films, Examples include paper, synthetic paper, cloth, and metal foil.
このような支持体の厚さは、通常５〜１０００μｍ、好ましくは２０〜５００μｍである。 The thickness of such a support is usually 5 to 1000 μm, preferably 20 to 500 μm.
また、粘着製品の支持体を設けた反対側の面には、粘着剤層を保護するため剥離シートを積層してもよい。剥離シートとしては、特に限定されず、例えば、ポリエチレン、ポリエステル等のフィルムに剥離剤としてシリコーン樹脂を塗布したものが挙げられる。 Moreover, you may laminate | stack a peeling sheet in order to protect an adhesive layer in the surface on the opposite side which provided the support body of the adhesive product. It does not specifically limit as a peeling sheet, For example, what apply | coated the silicone resin as a peeling agent to films, such as polyethylene and polyester, is mentioned.
更に、本発明の粘着製品は、前述の支持体を用いない形であってもよい。この場合、粘着製品は、粘着剤層の両面が剥離シートで保護された形状で使用される。また、剥離シートを用いずに、一方の面に粘着剤層を有し、他方の面が当該粘着剤層の粘着剤に対し剥離性を有する支持体からなら粘着製品として巻体として使用してもよい。 Furthermore, the pressure-sensitive adhesive product of the present invention may be in a form that does not use the above-mentioned support. In this case, the pressure-sensitive adhesive product is used in a shape in which both surfaces of the pressure-sensitive adhesive layer are protected by the release sheet. Also, without using a release sheet, if it has a pressure-sensitive adhesive layer on one side and the other side is a support that has peelability to the pressure-sensitive adhesive of the pressure-sensitive adhesive layer, it can be used as a roll as a pressure-sensitive adhesive product. Also good.
本発明の粘着製品の製造に際しては、前述の粘着剤の配合物を混合撹拌した後、ナイフコーター、ロールナイフコーター、リバースロールコーター、グラビアコーター、ダイコーター等の公知の塗工装置により、前述の支持体又は剥離シート上に所望の厚さに塗工する。該配合物が溶液、懸濁液等である場合は、乾燥により溶媒等の揮発分を除去し、粘着剤層を形成する。次いで、露出した粘着剤層側に剥離シート又は支持体を積層して本発明の粘着製品が製造される。 In the production of the pressure-sensitive adhesive product of the present invention, after mixing and stirring the above-mentioned pressure-sensitive adhesive composition, the above-described pressure-sensitive adhesive coating apparatus such as a knife coater, a roll knife coater, a reverse roll coater, a gravure coater, and a die coater is used. Apply to desired thickness on support or release sheet. When the blend is a solution, suspension or the like, volatile components such as a solvent are removed by drying to form an adhesive layer. Next, a release sheet or a support is laminated on the exposed pressure-sensitive adhesive layer side to produce the pressure-sensitive adhesive product of the present invention.
本発明の粘着製品は、例えば創傷被覆材、穿刺部固定部材、絆創膏等の粘着テープや、手術用ドレープ、また医療用具に貼付する粘着ラベルとして好適に用いられる。 The pressure-sensitive adhesive product of the present invention is suitably used as a pressure-sensitive adhesive label that is attached to a pressure-sensitive adhesive tape such as a wound dressing, a puncture fixing member, or a bandage, a surgical drape, or a medical device.
以下、実施例及び比較例により本発明を更に具体的に説明するが、これらは本発明の範囲を何ら制限するものではない。 EXAMPLES Hereinafter, although an Example and a comparative example demonstrate this invention further more concretely, these do not restrict | limit the scope of the present invention at all.
（実施例１）
アクリル酸ｎ−ブチル６５質量部、アクリル酸２−エチルヘキシル３２質量部、アクリル酸３質量部及び酢酸エチル５０質量部の混合溶液に重合開始剤としてアゾビスイソブチロニトリル０．２５質量部を加え、更に酢酸エチル５０．２５質量部を加えながら、不活性ガス雰囲気中で６５℃にて１２時間重合を行い、アクリル系粘着剤溶液を調製した。（固形分濃度５０％）
Example 1
Add 0.25 parts by mass of azobisisobutyronitrile as a polymerization initiator to a mixed solution of 65 parts by mass of n-butyl acrylate, 32 parts by mass of 2-ethylhexyl acrylate, 3 parts by mass of acrylic acid and 50 parts by mass of ethyl acetate. Furthermore, while adding 50.25 parts by mass of ethyl acetate, polymerization was carried out at 65 ° C. for 12 hours in an inert gas atmosphere to prepare an acrylic pressure-sensitive adhesive solution. (Solid content concentration 50%)
ヨウ素−シクロデキストリン包接化物（β−シクロデキストリンとヨウ素との包接体（有効ヨウ素２０質量％含有品）の粉末；製品名「ＢＣＤＩ（２０％）」；販売元：純正化学株式会社、製造元：日宝化学株式会社）１００質量部に対し、プロピレングリコール４００質量部を加え、予め完全に溶解させておいた。 Iodine-cyclodextrin inclusion product (inclusion body of β-cyclodextrin and iodine (containing 20% by mass of effective iodine); product name “BCDI (20%)”; distributor: Junsei Co., Ltd., manufacturer : Nichiho Chemical Co., Ltd.) To 100 parts by mass, 400 parts by mass of propylene glycol was added and completely dissolved in advance.
また、水素化ロジンエステル（荒川化学工業社製、超淡色ロジンエステルＫＥ−３１１）１００質量部に対し、酢酸エチル１００質量部を加え、これも完全に溶解させておいた。 Further, 100 parts by mass of ethyl acetate was added to 100 parts by mass of hydrogenated rosin ester (Arakawa Chemical Industries, Ltd., super pale rosin ester KE-311), and this was also completely dissolved.
前記の得られたアクリル系粘着剤１００質量部（固形分）に対し、前記のヨウ素−シクロデキストリン包接化物のプロピレングリコール溶液３７．０４質量部、前記の水素化ロジンエステルの酢酸エチル溶液２２．２質量部及びヘキサメチレンジエチレン尿素（有機多価イミン化合物系架橋剤）０．４質量部（固形分）を加えた後、混合撹拌してアクリル系粘着剤塗工液を調製した。 With respect to 100 parts by mass (solid content) of the obtained acrylic pressure-sensitive adhesive, 37.04 parts by mass of the propylene glycol solution of the inclusion product of iodine-cyclodextrin, and the ethyl acetate solution of the hydrogenated rosin ester 22. 2 parts by mass and 0.4 parts by mass (solid content) of hexamethylene diethylene urea (organic polyvalent imine compound-based crosslinking agent) were added, followed by mixing and stirring to prepare an acrylic pressure-sensitive adhesive coating solution.
前記アクリル系粘着剤塗工液を剥離シート（リンテック（株）製、商品名ＳＰ−ＫＰ８５Ｇシロ）に乾燥後の塗布量が４０ｇ／ｍ２となるように塗布し、１００℃で２分間乾燥し、ポリウレタンフィルム（厚さ３０μｍ）と貼り合わせ、粘着剤をポリウレタン側に転写することにより本発明の粘着テープ（粘着剤中のヨウ素含有率０．９３質量％）を得た。 The acrylic pressure-sensitive adhesive coating solution was applied to a release sheet (trade name SP-KP85G white, manufactured by Lintec Corporation) so that the coating amount after drying was 40 g / m 2 and dried at 100 ° C. for 2 minutes. The pressure-sensitive adhesive tape of the present invention (iodine content of 0.93 mass%) was obtained by bonding to a polyurethane film (thickness 30 μm) and transferring the pressure-sensitive adhesive to the polyurethane side.
（実施例２）
実施例１と同様にして得られたアクリル系粘着剤１００質量部（固形分）に対し、実施例１と同様のヨウ素−シクロデキストリン包接化物のプロピレングリコール溶液５９．８２質量部、実施例１と同様の水素化ロジンエステルの酢酸エチル溶液２２．２質量部及びヘキサメチレンジエチレン尿素（有機多価イミン化合物系架橋剤）０．４質量部（固形分）を加えた後、混合撹拌してアクリル系粘着剤塗工液を調製した。
(Example 2)
59.82 parts by mass of a propylene glycol solution of an iodine-cyclodextrin inclusion product as in Example 1 with respect to 100 parts by mass (solid content) of the acrylic pressure-sensitive adhesive obtained in the same manner as in Example 1, Example 1 After adding 22.2 parts by mass of an ethyl acetate solution of a hydrogenated rosin ester and 0.4 parts by mass (solid content) of hexamethylenediethylene urea (organic polyvalent imine compound-based crosslinking agent), the mixture was stirred and mixed with acrylic. A system adhesive coating solution was prepared.
前記アクリル系粘着剤塗工液を剥離シート（リンテック（株）製、商品名ＳＰ−ＫＰ８５Ｇシロ）に乾燥後の塗布量が４０ｇ／ｍ２となるように塗布し、１００℃で２分間乾燥し、ポリウレタンフィルム（厚さ３０μｍ）と貼り合わせ、粘着剤をポリウレタン側に転写することにより本発明の粘着テープ（粘着剤中のヨウ素含有率１．３１質量％）を得た。 The acrylic pressure-sensitive adhesive coating solution was applied to a release sheet (trade name SP-KP85G white, manufactured by Lintec Corporation) so that the coating amount after drying was 40 g / m 2 and dried at 100 ° C. for 2 minutes. The pressure-sensitive adhesive tape of the present invention (the iodine content in the pressure-sensitive adhesive was 1.31% by mass) was obtained by bonding to a polyurethane film (thickness 30 μm) and transferring the pressure-sensitive adhesive to the polyurethane side.
（実施例３）
ヨウ素−シクロデキストリン包接化物を溶解する溶媒をエチレングリコールとした以外は実施例１と同様の方法によって粘着テープを得た。
(Example 3)
An adhesive tape was obtained in the same manner as in Example 1 except that ethylene glycol was used as the solvent for dissolving the iodine-cyclodextrin inclusion product.
（実施例４）
ヨウ素−シクロデキストリン包接化物を溶解する溶媒をプロピレングリコールに代えて酢酸エチルとした以外は実施例１と同様の方法によって粘着テープを得た。
Example 4
An adhesive tape was obtained in the same manner as in Example 1 except that ethyl acetate was used instead of propylene glycol as the solvent for dissolving the iodine-cyclodextrin inclusion product.
（比較例１）
ヨウ素−シクロデキストリン包接化物を配合しない以外は実施例１と同様の方法によって粘着テープを得た。
実施例及び比較例の粘着テープについて、下記の方法に従って、黄色ブドウ球菌及び大腸菌に対する抗菌試験を行った。
(Comparative Example 1)
An adhesive tape was obtained in the same manner as in Example 1 except that no iodine-cyclodextrin inclusion product was added.
About the adhesive tape of an Example and a comparative example, the antibacterial test with respect to Staphylococcus aureus and Escherichia coli was done according to the following method.
（試験方法）
（１）試験菌
大腸菌（E. coli（ＡＴＣＣ８７３９））及び黄色ブドウ球薗（S. aureus（ＡＴＣＣ６５３８））（いずれも凍結乾燥状態）を購入して使用した。
(Test method)
(1) Test bacteria E. coli (ATCC8739) and S. aureus (ATCC6538) (both lyophilized) were purchased and used.
（２）試験菌液の調製
・予備培養
菌液を白金耳を用いて５ｍＬのNutrient broth（ＣＭ１）；ニュートリエントブイヨン（ＯＸＯＩＤ社製）中に菌を移植し、３２℃で約１８時間静置予備培養した。
・本培養
予備培養液２ｍＬを予備培養と同じニュートリエントブイヨン（１００ｍＬ）に入れ、２．５時間振盪培養した。
(2) Preparation and preliminary culture of test bacterial solution Using a platinum loop, the bacterial solution is transplanted into 5 mL of Nutrient broth (CM1); Nutrient broth (manufactured by OXOID) and allowed to stand at 32 ° C for about 18 hours. Pre-cultured.
-Main culture 2 mL of the preculture was placed in the same nutrient broth (100 mL) as the preculture, and cultured with shaking for 2.5 hours.
（３）抗菌試験
粘着テープの剥離シートを剥がし、粘着面を上にして固定した。
粘着面に予め用意しておいた前記の菌液（０．１ｍＬ）を滴下し、剥離シートを被せた後、シャーレ中で３２℃×２４時間培養した。培養中の菌液の乾燥を防止するため、シャーレ内に容器を用意し、粘着テープはその中に固定し、シャーレには水をはった。
(3) Antibacterial test The release sheet of the adhesive tape was peeled off and fixed with the adhesive side facing up.
The bacterial solution (0.1 mL) prepared in advance on the adhesive surface was dropped and covered with a release sheet, and then cultured in a petri dish at 32 ° C. for 24 hours. In order to prevent drying of the bacterial solution during the culture, a container was prepared in the petri dish, the adhesive tape was fixed therein, and the petri dish was watered.
菌数の確認は、粘着テープ及び剥離シートを１０ｍＬの０．２％−Ｔｗｅｅｎ８０生理食塩水（１０ｍＬ）中にて十分に洗い流したものを、系列希釈した液をTryptone soya agar（ＣＭ１３１）：トリプトンソーヤ寒天培地（ＯＸＯＩＤ社製）上に滴下し、コンラージ棒で塗り広げ、コロニー数をカウントした。
結果を表１に示す。
The number of bacteria was confirmed by thoroughly washing the adhesive tape and release sheet in 10 mL of 0.2% -Tween 80 physiological saline (10 mL), and using a serially diluted solution of Tryptone soya agar (CM131): Tryptone The solution was dropped on a soya agar medium (manufactured by OXOID), spread with a large stick, and the number of colonies was counted.
The results are shown in Table 1.
ヨウ素−シクロデキストリン包接化物を配合しない比較例１の粘着テープにおいては細菌のコロニーが観察されたが、ヨウ素−シクロデキストリン包接化物を配合した実施例１〜４の粘着テープでは細菌のコロニーは観察されなかった。 Bacterial colonies were observed in the adhesive tape of Comparative Example 1 in which no iodine-cyclodextrin inclusion product was blended, but in the adhesive tapes of Examples 1-4 in which iodine-cyclodextrin inclusion product was blended, the bacterial colonies were Not observed.
Claims (7)
前記アクリル系粘着剤が、少なくとも（メタ）アクリル酸アルキルエステル及びアクリル酸を含む原料単量体を重合したアクリル系重合体を、架橋剤で架橋してなるアクリル系粘着剤であり、
前記架橋剤が、有機多価イミン化合物系架橋剤であることを特徴とする粘着製品。 An adhesive product containing an iodine-cyclodextrin inclusion product, a polyhydric alcohol and an acrylic adhesive in the adhesive layer,
The acrylic adhesive, at least (meth) acrylic polymer obtained by polymerizing raw material monomers containing the acrylic acid alkyl ester and acrylic acid, Ri acrylic adhesive der obtained by crosslinking with a crosslinking agent,
The pressure-sensitive adhesive product , wherein the cross-linking agent is an organic polyvalent imine compound-based cross-linking agent .
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| CN113122166B (en) * | 2021-04-19 | 2023-10-20 | 黑龙江大学 | Composite antibacterial pressure-sensitive adhesive composition and preparation method thereof |
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