JP6761437B2 - 殺菌作用を備えた表面を有する合成高分子膜、合成高分子膜を有するプラスチック製品、合成高分子膜の表面を用いた殺菌方法、光硬化性樹脂組成物、および合成高分子膜の製造方法 - Google Patents
殺菌作用を備えた表面を有する合成高分子膜、合成高分子膜を有するプラスチック製品、合成高分子膜の表面を用いた殺菌方法、光硬化性樹脂組成物、および合成高分子膜の製造方法 Download PDFInfo
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- JP6761437B2 JP6761437B2 JP2018048186A JP2018048186A JP6761437B2 JP 6761437 B2 JP6761437 B2 JP 6761437B2 JP 2018048186 A JP2018048186 A JP 2018048186A JP 2018048186 A JP2018048186 A JP 2018048186A JP 6761437 B2 JP6761437 B2 JP 6761437B2
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- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- 230000003746 surface roughness Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- JBQYATWDVHIOAR-UHFFFAOYSA-N tellanylidenegermanium Chemical compound [Te]=[Ge] JBQYATWDVHIOAR-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000032258 transport Effects 0.000 description 1
- YWYZEGXAUVWDED-UHFFFAOYSA-N triammonium citrate Chemical compound [NH4+].[NH4+].[NH4+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O YWYZEGXAUVWDED-UHFFFAOYSA-N 0.000 description 1
- WYXIGTJNYDDFFH-UHFFFAOYSA-Q triazanium;borate Chemical compound [NH4+].[NH4+].[NH4+].[O-]B([O-])[O-] WYXIGTJNYDDFFH-UHFFFAOYSA-Q 0.000 description 1
- 241000712461 unidentified influenza virus Species 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
-
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
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- C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
- C08K5/092—Polycarboxylic acids
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- B32B23/00—Layered products comprising a layer of cellulosic plastic substances, i.e. substances obtained by chemical modification of cellulose, e.g. cellulose ethers, cellulose esters, viscose
- B32B23/04—Layered products comprising a layer of cellulosic plastic substances, i.e. substances obtained by chemical modification of cellulose, e.g. cellulose ethers, cellulose esters, viscose comprising such cellulosic plastic substance as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B23/08—Layered products comprising a layer of cellulosic plastic substances, i.e. substances obtained by chemical modification of cellulose, e.g. cellulose ethers, cellulose esters, viscose comprising such cellulosic plastic substance as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
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- B32B3/30—Layered products comprising a layer with external or internal discontinuities or unevennesses, or a layer of non-planar form; Layered products having particular features of form characterised by a particular shape of the outline of the cross-section of a continuous layer; characterised by a layer with cavities or internal voids ; characterised by an apertured layer characterised by a layer formed with recesses or projections, e.g. hollows, grooves, protuberances, ribs
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- C08F265/06—Polymerisation of acrylate or methacrylate esters on to polymers thereof
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- C08K5/0058—Biocides
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K5/07—Aldehydes; Ketones
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3415—Five-membered rings
- C08K5/3417—Five-membered rings condensed with carbocyclic rings
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- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
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- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
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- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
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- B32B2307/70—Other properties
- B32B2307/714—Inert, i.e. inert to chemical degradation, corrosion
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- B32B2439/00—Containers; Receptacles
- B32B2439/70—Food packaging
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- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
- C08F220/285—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing a polyether chain in the alcohol moiety
- C08F220/286—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing a polyether chain in the alcohol moiety and containing polyethylene oxide in the alcohol moiety, e.g. methoxy polyethylene glycol (meth)acrylate
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- C08J2301/00—Characterised by the use of cellulose, modified cellulose or cellulose derivatives
- C08J2301/08—Cellulose derivatives
- C08J2301/10—Esters of organic acids
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- C08J2333/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
- C08J2333/04—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters
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Description
オンからなる群から選択される少なくとも1つを含む。
オンからなる群から選択される少なくとも1つを含む。
第1の凹部の中に、Dpが約50nmの第2の凹部が形成された。
42は、図6に示すように、支持ローラ46および48によって支持されている。支持ローラ46および48は、回転機構を有し、ベースフィルム42を搬送する。また、円筒状のモスアイ用型100は、ベースフィルム42の搬送速度に対応する回転速度で、図6に矢印で示す方向に回転される。
参考例1〜7、本発明の実施形態による実施例1〜12、および比較例1〜3の各試料フィルムを作製した。各試料フィルム(参考例1を除く。)は、ベースフィルムと、ベースフィルム上に形成された合成高分子膜とを有する。参考例1は、厚さが50μmのPETフィルム(東洋紡株式会社製の「A4300」)である。各試料フィルムの合成高分子膜を形成する紫外線硬化性樹脂に使用した原材料を表1に示す。
m2(波長が375nmの光を基準)とし、無溶剤で合成高分子膜を作製した。紫外線照
射には、Fusion UV Systems社製のUVランプ(製品名:LIGHT HANMAR6J6P3)を用いた。
。例えば、アルミニウム層18pの下に無機下地層を形成することによって、アルミニウム層18pの表面に無機下地層の表面形状を反映させることができる。さらに、無機下地層の表面をエッチャントに接触させることによって、無機下地層の表面の凹凸構造の深さ(高さ)を大きくしてもよい。あるいは、アルミニウム層18pの表面をエッチャントに接触させることによって、アルミニウム層18pの表面の凹凸構造の深さ(高さ)を大きくすることもできる。例えば、燐酸水溶液(10質量%、30℃)を用いて50分間以上エッチングを行う。これらの方法を併用してももちろんよい。このように、アルミニウム層18pの成膜条件以外の方法で、型100Cの表面の凹凸構造の形状を調整する場合、アルミニウム層18pの厚さは、上述した範囲よりも小さくてもよい。例えば、高純度アルミニウム層18pの厚さは、1μm以上2μm未満であってもよく、アルミニウム合金層18pの厚さは、1μm以上4μm未満であってもよい。アルミニウム層(高純度アルミニウム層またはアルミニウム合金層)18pの厚さが大きいと、結晶粒界18pbが深くなるので、転写性に劣る場合がある。アルミニウム層18pの下に無機下地層を形成すると、アルミニウム層18pの厚さを小さくすることができるので、優れた転写性が得られるという利点が得られ得る。
試料フィルム上に飛散した菌液(水)に対する殺菌性を評価した。菌液を付与した試料フィルムを室温・大気中に放置した際の殺菌性を評価した。ここでは、黄色ブドウ球菌に対する殺菌性を評価した。具体的な評価方法は以下の通りである。各試料フィルムについて、N=3で実験を行った。
(1)初期菌数が1E+06CFU/mLとなるように、黄色ブドウ球菌を含む菌液を1/500NB培地を用いて調製した。
(2)各試料フィルム(5cm角)の上に、上記菌液10μLを滴下した。
(3)室温(約25℃)、大気中に、15分間、放置した後、SCDLP培地を試料フィルムにかけ流し、菌を洗い出した(洗い出し液)。
(4)洗い出し液を適宜PBSで希釈を行い、標準寒天培地等で培養し、菌数をカウントした。
生菌率(%)=各試料フィルムの菌数(N=3の合計)/参考例1の試料フィルムの菌数(N=3の合計)×100
合成高分子膜のベースフィルムに対する密着性は、以下の様にして評価した。
・合成高分子膜上の水の広がり程度
脱イオン水を0.01mol/L−塩酸および0.011mol/L−水酸化ナトリウムにてpH=7.0±0.1に調整した。すなわち、このようにして、中性の水を用意した。
pHの測定は、以下の様にして行った。
電極:株式会社堀場製作所製、pH電極、型番:0040−10D(半導体センサ)
サンプリングシート:株式会社堀場製作所製、サンプリングシートB、型番:Y011A
接触角計(協和界面科学株式会社製、PCA−1)を用いて、各試料フィルムの合成高分子膜の表面に対する、水の静的接触角を測定した。各試料フィルムの合成高分子膜の表面に、水の液滴(およそ10μL )を滴下し、それぞれ、滴下後1秒後、10秒後および60秒後の静的接触角を測定した。θ/2法(θ/2=arctan(h/r)、θ:接触角、r:液滴の半径、h:液滴の高さ)で測定された、3箇所の接触角の平均値を求めた。ここで、1箇所目の測定点としては、各試料フィルムの中央部分を選択し、2箇所目及び3箇所目の測定点としては、1箇所目の測定点から20mm以上離れ、かつ、1箇所目の測定点に対して互いに点対称な位置にある2点を選択した。
各試料フィルムから水に抽出される酸をGC−MS(ガスクロマトグラフ質量分析計)を用いて以下のようにして同定した。
熱分解装置:FRONTIER LAB 社製 EGA/PY−3030D
条件: 400℃/30sec
GC−MS装置: Agilent Technologies 社製 7890A(GC) 5975C(MS)
カラム: FRONTIER LAB 製 UA5HT−30M−0.1F
条件:オーブン 40℃⇒320℃(20℃/min)
カラム流量 1mL/min
スプリット比 100:1
合成高分子膜の架橋構造における合成高分子膜の全体に対するエチレンオキサイド単位の含有率が35質量%以上70質量%未満であり、(メタ)アクリル酸2−(2−ビニロキシエトキシ)エチルモノマー単位の含有率が15質量%以上45質量%未満であれば、優れたPC密着性および殺菌性を有し得る。PCは、エンジニアリングプラスチックの中でも平均して高い物性を示す樹脂で、特に、耐衝撃性および耐熱性に優れるので、幅広く利用されている。
0:任意に溶解する
1:極めて溶けやすい 1mL未満
2:溶けやすい 1mL以上 10mL未満
3:やや溶けやすい 10mL以上 30mL未満
4:やや溶けにくい 30mL以上 100mL未満
5:溶けにくい 100mL以上 1000mL未満
6:極めて溶けにくい 1000mL以上 10000mL未満
7:ほとんど溶けない 10000mL以上
・直接添加物(Direct Additives):ヒト が摂取する食品に直接加えることができる添加物(21 CFR Part 172)。
・二次的直接添加物(Secondary Direct Additives):酵素製剤等、食品の加工を促進する等の目的で加えることができる添加物(21 CFR Part 173)。
・GRAS物質:一般的に安全と認められる物質(21 CFR Part 182)。
・GRAS直接添加物:食品医薬品局(FDA)によりGRASであることが確認された物質(21 CFR Part 184)。
・GRAS Notificationに掲載されている物質(FDA GRAS Notification)。
34Ap、34Bp 凸部
34Cd 凹部
42A、42B ベースフィルム
50A、50B、50C フィルム
100、100A、100B、100C 型
Claims (25)
- 複数の凸部または凹部を有する表面を備える合成高分子膜であって、
架橋構造を有し、
食品に添加することが食品衛生法で認められている、抗菌効果を有する抗菌性添加物を含み、
前記合成高分子膜の法線方向から見たとき、前記複数の凸部または凹部の2次元的な大きさは20nm超1μm以下の範囲内にあり、
前記架橋構造は、(メタ)アクリル酸2−(2−ビニロキシエトキシ)エチルモノマー単位を含む、合成高分子膜。 - 前記抗菌性添加物は、有機カルボン酸を含み、
前記合成高分子膜の前記表面に200μLの水を滴下後、5分後の水溶液のpHが5以下であり、前記水溶液の面積円相当径が20mm以上である、請求項1に記載の合成高分子膜。 - 複数の凸部または凹部を有する表面を備える合成高分子膜であって、
架橋構造を有し、
食品に添加することが食品衛生法で認められている、抗菌効果を有する抗菌性添加物を含み、
前記合成高分子膜の法線方向から見たとき、前記複数の凸部または凹部の2次元的な大きさは20nm超1μm以下の範囲内にあり、
前記抗菌性添加物は、有機カルボン酸を含み、
前記合成高分子膜の前記表面に200μLの水を滴下後、5分後の水溶液のpHが5以下であり、前記水溶液の面積円相当径が20mm以上である、合成高分子膜。 - 前記有機カルボン酸1gを溶解するために必要な水の量が1mL以上10000mL未満である、請求項2または3に記載の合成高分子膜。
- 前記有機カルボン酸は、コハク酸、アジピン酸、クエン酸、アルギン酸、またはフィチン酸である、請求項2から4のいずれかに記載の合成高分子膜。
- 食品に添加することが食品衛生法で認められている乳化剤をさらに含む、請求項2から5のいずれかに記載の合成高分子膜。
- 前記乳化剤のHLB値は、7以上14以下である、請求項6に記載の合成高分子膜。
- 前記合成高分子膜の法線方向から見たとき、前記複数の凸部または凹部の2次元的な大きさは500nm未満である、請求項1から7のいずれかに記載の合成高分子膜。
- 前記複数の凸部または凹部は、モスアイ構造を構成する複数の凸部である、請求項8に記載の合成高分子膜。
- 前記合成高分子膜の法線方向から見たとき、前記複数の凸部または凹部の2次元的な大きさは500nm以上である、請求項1から7のいずれかに記載の合成高分子膜。
- 前記複数の凸部または凹部は、アルミニウム層が有する複数の結晶粒の表面形状が反転された複数の凹部である、請求項10に記載の合成高分子膜。
- 光重合開始剤を含む光硬化性樹脂から形成されている、請求項1から11のいずれかに記載の合成高分子膜。
- 前記光硬化性樹脂の全体に対する、前記抗菌性添加物の含有率は0.1質量%以上10質量%以下である、請求項12に記載の合成高分子膜。
- 前記光重合開始剤は、光分解によって有機カルボン酸を実質的に生成しない、請求項12または13に記載の合成高分子膜。
- 前記光硬化性樹脂は、ラジカル重合性である、請求項12から14のいずれかに記載の合成高分子膜。
- 前記光重合開始剤は、エタノン,1-[9-エチル-6-(2-メチルベンゾイル)-9H-カルバゾール-3-イル]-,1-(O-アセチルオキシム)、2-ヒドロキシ-1-[4-[4-(2-ヒドロキシ-2-メチル-プロピオニル)-ベンジル]フェニル]-2-メチル-プロパン-1-オン、および1-[4-(2-ヒドロキシエトキシ)-フェニル]-2-ヒドロキシ-2-メチル-1-プロパン-1-オンからなる群から選択される少なくとも1つを含む、請求項12から15のいずれかに記載の合成高分子膜。
- 前記架橋構造は、ウレタン結合を構成する窒素元素およびフッ素元素を含まない、請求項1から16のいずれかに記載の合成高分子膜。
- 前記架橋構造は、エチレンオキサイド単位を含む、請求項1から17のいずれかに記載の合成高分子膜。
- 表面を有するプラスチック基材と、前記プラスチック基材の前記表面に形成された、請求項1から18のいずれかに記載の合成高分子膜とを有する、プラスチック製品。
- 前記プラスチック基材は、トリアセチルセルロースフィルム、ポリエチレンテレフタレートフィルム、およびポリカーボネートフィルムからなる群から選択される少なくとも1つのフィルムを含み、
前記少なくとも1つのフィルムと前記合成高分子膜とを含む、積層フィルムである、請求項19に記載のプラスチック製品。 - 前記プラスチック基材は、ポリカーボネートを含み、容器を形成している、請求項19に記載のプラスチック製品。
- 請求項1から18のいずれかに記載の合成高分子膜の前記表面に、水を含む液体を接触させることによって、前記液体を殺菌する方法。
- 請求項1から18のいずれかに記載の合成高分子膜の製造に用いられる光硬化性樹脂組成物であって、
光硬化性樹脂と、食品に添加することが食品衛生法で認められている、抗菌効果を有する抗菌性添加物と、光重合開始剤とを含む、光硬化性樹脂組成物。 - 前記光重合開始剤は、エタノン,1-[9-エチル-6-(2-メチルベンゾイル)-9H-カルバゾール-3-イル]-,1-(O-アセチルオキシム)、2-ヒドロキシ-1-[4-[4-(2-ヒドロキシ-2-メチル-プロピオニル)-ベンジル]フェニル]-2-メチル-プロパン-1-オン、および1-[4-(2-ヒドロキシエトキシ)-フェニル]-2-ヒドロキシ-2-メチル-1-プロパン-1-オンからなる群から選択される少なくとも1つを含む、請求項23に記載の光硬化性樹脂組成物。
- 請求項23または24に記載の光硬化性樹脂組成物に水を混合した後に、光照射を行う工程を含む、合成高分子膜の製造方法。
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