JP5633147B2 - 医療用抗菌性組成物および医療用具 - Google Patents
医療用抗菌性組成物および医療用具 Download PDFInfo
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- JP5633147B2 JP5633147B2 JP2009511284A JP2009511284A JP5633147B2 JP 5633147 B2 JP5633147 B2 JP 5633147B2 JP 2009511284 A JP2009511284 A JP 2009511284A JP 2009511284 A JP2009511284 A JP 2009511284A JP 5633147 B2 JP5633147 B2 JP 5633147B2
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- siloxanyl
- antibacterial composition
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- 239000012780 transparent material Substances 0.000 description 1
- LVLANIHJQRZTPY-UHFFFAOYSA-N vinyl carbamate Chemical group NC(=O)OC=C LVLANIHJQRZTPY-UHFFFAOYSA-N 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000011800 void material Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
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Description
〔1〕アンモニウム基を有する高分子化合物(A)が、シロキサニル構造含有ポリマー(B)中に分散されてなり、
医療用抗菌性組成物中の炭素原子に結合した水酸基数をOH、アンモニウム窒素の数をNで表すとき、N/OH比が0.001〜0.5であり、
医療用抗菌性組成物中のケイ素原子数のうちの30%以上が、極性シロキサニルモノマー由来のケイ素原子であり、
前記高分子化合物(A)の含有量は、0.01〜20重量%であり、
前記シロキサニル構造含有ポリマー(B)のうちの少なくとも1種類は、下記一般式(a)
M−L−Sx・・・(a)
[式中、Mはラジカル重合可能な重合性基を表し、Lは下記一般式(b)又は(c)
で示されるシロキサニルモノマーから得られる構造を有している、医療用抗菌性組成物(ただし、高分子化合物100重量部中のアンモニウム塩モノマー単位の含有量が0.01〜10重量部である眼用レンズ用モノマー組成物を除く。)
〔3〕前記シロキサニルモノマーのうち、少なくとも1種類が式(e)および(g)
からなる群から選ばれた極性シロキサニルモノマーであることを特徴とする前記〔1〕または〔2〕のいずれかに記載の医療用抗菌性組成物。
〔4〕前記アンモニウム基を有する高分子化合物(A)が、下記一般式(f)
(R1は炭素数1〜30の置換されていてもよいアルキル基を表す。R2〜R7は水素、炭素数1〜20の置換されていてもよいアルキル基、および炭素数6〜20の置換されていてもよいアリール基から選ばれた置換基を表す。R2とR3は環を形成していてもよい。X−は任意のアニオンを表す。)
〔5〕高分子化合物(A)と混合した状態で、シロキサニル構造含有ポリマー(B)を構成するモノマーおよび/またはマクロモノマーを重合させて得られることを特徴とする前記〔1〕〜〔4〕のいずれかに記載の医療用抗菌性組成物。
〔6〕前記〔1〕〜〔5〕のいずれかに記載の医療用抗菌性組成物を含有する医療用具。
〔7〕少なくとも一部が前記〔1〕〜〔5〕のいずれかに記載の医療用抗菌性組成物によって被覆されてなることを特徴とする医療用具。
〔8〕シリコーン樹脂を含有する成型体であることを特徴とする前記〔6〕または〔7〕に記載の医療用具。
〔9〕チューブ状、および細い棒状から選ばれた形状を有することを特徴とする前記〔6〕〜〔8〕のいずれかに記載の医療用具。
〔10〕内視鏡、カテーテル、輸液チューブ、気体輸送チューブ、ステント、シース、カフ、チューブコネクター、アクセスポート、排液バック、および血液回路から選ばれた1種であることを特徴とする前記〔9〕に記載の医療用具。
〔11〕胃婁チューブであることを特徴とする前記〔9〕に記載の医療用具。
M−L−Sx (a)
で表される、分子内に重合性基を一つ有する構造のシロキサニルモノマーである。
で表されるシロキサニルモノマーである。さらに、ポリビニルピロリドンなどの内部湿潤剤と混合しても透明なシロキサニル構造含有ポリマーが容易に得られることから、式(e)、式(g)で表されるような分子内に水酸基を有するシロキサニルモノマーが最も好ましい。
・カラム:TSKgel SUPER HM−H 2本直列
・移動相:N−メチルピロリドン(LiBr 10mM含有)
・カラム温度:40℃
・移動相流量:0.2mL/分
・測定時間:40分間
・サンプル濃度:0.4重量%(N−メチルピロリドン溶媒)
・注入量:10μL
・標準ポリスチレン換算
・検出:RI検出器
本発明の医療用抗菌性組成物に用いられる高分子化合物(A)は、架橋された高分子化合物ではなく、溶媒への溶解が可能なものである。
で表されるアンモニウム塩モノマーなどが挙げられる。それらのうち、医療用抗菌性組成物の透明性、および熱安定性と抗菌性の点で最も好ましいのは一般式(f)で表されるビニルイミダゾリウム塩である。
下記式(y1)
50mLナスフラスコにN−ビニルイミダゾール(4.71g、50mmol)、ヨウ化n−オクチル(12.01g、50mmol)、2,6−ジ−t−ブチル−4−メチルフェノール(BHT、0.1672g)を加え、65℃で14時間加熱した。反応後、シリカゲル90gを用い、クロロホルム/メタノール=50/1(360mL)、クロロホルム/メタノール=30/1(360mL)、クロロホルム/メタノール=20/1(360mL)、クロロホルム/メタノール=10/1(180mL)、およびクロロホルム/メタノール=5/1(180mL)をこの順に溶出液として用いてカラム精製した。薄層クロマトグラフィーで目的物のスポットが含まれるフラクションを集め、エバポレータで溶媒を留去して、下記式(x1)で表される黄色オイル状のアンモニウム塩モノマーを得た。
上記合成例1で得られた式(x1)で表されるモノマー(1g)、3,7−ジメチル−3−オクタノール(1g)、光開始剤イルガキュア1850(0.02g)を混合し、撹拌した。このモノマー混合物をアルゴン雰囲気下で脱気し、窒素雰囲気下のグローブボックス中で直径5cmのシャーレに流し込んだ。光照射(東芝FL6D蛍光灯、8.4キロルクス、15分間)を行った後、なるべく少量のメタノールに溶解し、500mLの酢酸エチル中に撹拌しながら滴下後、5℃で3時間静置した。ろ過して得られた固形分を少量の酢酸エチルで洗い、デシケータ中で減圧することにより溶媒を留去して、上記式(x1)で表されるモノマーのホモポリマーであるポリ(ビニルオクチルイミダゾリウムヨージド)を得た。
モノマー組成を、式(y1)で表されるシロキサニル化合物(22重量部)、下記式(y3)
ポリ(ビニルオクチルイミダゾリウムヨージド)の使用量を下の表1のように変える以外は実施例2の方法にしたがって、重合、後処理を行い、抗菌性評価用サンプルを得た。得られたフィルム状サンプルはいずれも透明で濁りが無く、外観品位に優れていた。また、該サンプルを指で触って確認したところ、いずれのフィルムも柔軟であり、しかも折り曲げても破れることが無く機械的特性に優れることが分かった。
モノマー混合液中に高分子化合物を加えない以外は実施例1と同様にしてフィルム状サンプルを得た。3cm角に切り出して抗菌性評価用サンプルとした。
比較例1で得られたフィルム状サンプルを50mLスクリュー管に入れ、1.7%PVP/ポリメチルビニルイミダゾリウムクロリド(95/5)水溶液に室温で16時間浸漬した。
実施例1〜4で得られたフィルム状サンプルを3枚用意し、JIS Z 2801:2000「抗菌加工製品−抗菌性試験方法・抗菌効果」5.2 プラスチック製品などの試験方法に基づき、コンタクトレンズ使用時にみられる代表的な細菌の一つである緑膿菌(Pseudomonas aeruginosa NBRC 13275)をフィルム状サンプルに接種し、接種した直後の菌数(初期菌数)および35℃、24時間後の菌数をカウントして抗菌評価を行った。その結果は表2および3の通りであり、高分子化合物を加えずに重合した比較例1で得られたフィルム状サンプルでは初期菌数と比較して増殖が見られたのに対し、実施例1で得られたフィルム状サンプルでは初期菌数と比較して1桁の減少が、また、実施例2〜4では5桁の減少が見られ、十分な抗菌性を示した。
実施例1および比較例2で得られたフィルム状サンプルを300mLの蒸留水に浸漬し、超音波で15分間洗浄した後、取り出して上記と同様の抗菌評価を行った。その結果は下表4の通りであり、抗菌性高分子水溶液に浸漬したのみの比較例2で得られたフィルム状サンプルでは抗菌性が失われて菌の増殖が見られたのに対して、実施例1で得られたフィルム状サンプルは超音波洗浄後も十分な抗菌性を有することが示された。
モノマー組成を、式(y1)で表されるシロキサニル化合物(w1重量部)、式(y3)で表されるシロキサニル化合物(w2重量部)、式(y2)で表される片末端がメタクリル化されたポリジメチルシロキサン(チッソ製、“サイラプレーン”FM−0711、重量平均分子量約1000、w3重量部)、メタクリロキシプロピルトリス(トリメチルシロキシ)シラン(w4重量部)、N,N−ジメチルアクリルアミド(V1重量部)、ポリビニルピロリドン(K−90、8重量部)、2−ヒドロキシエチルメタクリレート(V2重量部)、トリ(エチレングリコール)ジメタクリレート(1重量部)、両末端がメタクリル化されたポリジメチルシロキサン(信越化学工業製、X−22−164A、1重量部)、上記合成例2で得られたポリ(ビニルオクチルイミダゾリウムヨージド)(U重量部)、光開始剤イルガキュア1850(2重量部)、3,7−ジメチル−3−オクタノール(18重量部)の混合物に変えて実施例1と同様の重合、後処理を行い、抗菌性評価用サンプルを得た。得られたサンプルの抗菌性評価結果および目視による透明性評価結果を表5に示した。比較のために実施例2の結果も表5中に併記した。
ポリ(ビニルオクチルイミダゾリウムヨージド)の代わりに、同重量部のポリ(N−メタクリロキシエチル−N,N−ジメチル−N−ブチルアンモニウムヨージド)を使用した他は実施例2の方法にしたがって、重合、後処理を行い、抗菌性評価用サンプルを得た。得られたフィルム状サンプルは若干の濁りがあり透明性の点で実施例2で得られたサンプルよりも劣っていた。抗菌性評価結果は4桁の減少であった。
式(y1)で表されるシロキサニル化合物(23重量部)、式(y3)で表されるシロキサニル化合物(35重量部)、N,N−ジメチルアクリルアミド(28重量部)、ポリビニルピロリドン(K−90、8重量部)、2−ヒドロキシエチルメタクリレート(12重量部)、トリ(エチレングリコール)ジメタクリレート(1重量部)、両末端がメタクリル化されたポリジメチルシロキサン(信越化学X−22−164A、1重量部)、ポリ(ビニルオクチルイミダゾリウムヨージド)(3.7重量部)、光開始剤イルガキュア1850(2重量部)、および3,7−ジメチル−3−オクタノール(18重量部)からなるモノマー混合物をアルゴン雰囲気下で脱気した。
シリコーン樹脂製尿道カテーテルの代わりに、シリコーン樹脂製チューブ(外径15mm、内径12mm、長さ30cm)を用いる他は、実施例14と同様に行って医療用抗菌性組成物で被覆した輸液チューブを得た。
ポリ(ビニルオクチルイミダゾリウムヨージド)の代わりに、前記合成例3で得た式(x2)で表されるモノマーのホモポリマーを使用した以外は実施例2の方法にしたがって、重合、後処理を行い、フィルム状サンプルを得た。得られたフィルム状サンプルは透明で濁りが無く、外観品位に優れていた。また、該サンプルを指で触って確認したところ、いずれのフィルムも柔軟であり、しかも折り曲げても破れることが無く機械的特性に優れることが分かった。
式(y1)で表されるシロキサニル化合物(28.8重量部)、N,N−ジメチルアクリルアミド(35.5重量部)、式(y2)で表される片末端がメタクリル化されたポリジメチルシロキサン(チッソ製、“サイラプレーン”FM−0711、重量平均分子量約1000、26.8重量部)、2−ヒドロキシエチルメタクリレート(3.8重量部)、トリ(エチレングリコール)ジメタクリレート(3.0重量部)、式(x3)
Claims (11)
- アンモニウム基を有する高分子化合物(A)が、シロキサニル構造含有ポリマー(B)中に分散されてなり、
医療用抗菌性組成物中の炭素原子に結合した水酸基数をOH、アンモニウム窒素の数をNで表すとき、N/OH比が0.001〜0.5であり、
医療用抗菌性組成物中のケイ素原子数のうちの30%以上が、極性シロキサニルモノマー由来のケイ素原子であり、
前記高分子化合物(A)の含有量は、0.01〜20重量%であり、
前記シロキサニル構造含有ポリマー(B)のうちの少なくとも1種類は、下記一般式(a)
M−L−Sx・・・(a)
[式中、Mはラジカル重合可能な重合性基を表し、Lは下記一般式(b)又は(c)
で示されるシロキサニルモノマーから得られる構造を有している、医療用抗菌性組成物(ただし、高分子化合物100重量部中のアンモニウム塩モノマー単位の含有量が0.01〜10重量部である眼用レンズ用モノマー組成物を除く。) - 前記式(a)中のLが一般式(c)で表される基であることを特徴とする請求項1に記載の医療用抗菌性組成物。
- 高分子化合物(A)と混合した状態で、シロキサニル構造含有ポリマー(B)を構成するモノマーおよび/またはマクロモノマーを重合させて得られることを特徴とする請求項1〜4のいずれかに記載の医療用抗菌性組成物。
- 請求項1〜5のいずれかに記載の医療用抗菌性組成物を含有する医療用具。
- 少なくとも一部が請求項1〜5のいずれかに記載の医療用抗菌性組成物によって被覆されてなることを特徴とする医療用具。
- シリコーン樹脂を含有する成型体であることを特徴とする請求項6または7に記載の医療用具。
- チューブ状、および細い棒状から選ばれた形状を有することを特徴とする請求項6〜8のいずれかに記載の医療用具。
- 内視鏡、カテーテル、輸液チューブ、気体輸送チューブ、ステント、シース、カフ、チューブコネクター、アクセスポート、排液バック、および血液回路から選ばれた1種であることを特徴とする請求項9に記載の医療用具。
- 胃婁チューブであることを特徴とする請求項9に記載の医療用具。
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EP2325217A1 (en) * | 2009-11-19 | 2011-05-25 | AM Coatings B.V. | Microbial compounds and their use |
US20120015002A1 (en) * | 2010-05-25 | 2012-01-19 | 3M Innovative Properties Company | Antimicrobial coatings |
US9022967B2 (en) | 2010-10-08 | 2015-05-05 | Sinopsys Surgical, Inc. | Implant device, tool, and methods relating to treatment of paranasal sinuses |
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JP5452756B1 (ja) * | 2013-07-02 | 2014-03-26 | Hoya株式会社 | 親水性表面を有するシリコーン含有共重合体成形品を作製する方法及び親水性表面を有するシリコーンハイドロゲルコンタクトレンズ |
EP3179968B1 (en) * | 2014-07-24 | 2019-09-11 | Sinopsys Surgical, Inc. | Paranasal sinus access implant devices and related products and methods |
US10064273B2 (en) | 2015-10-20 | 2018-08-28 | MR Label Company | Antimicrobial copper sheet overlays and related methods for making and using |
JP7158143B2 (ja) * | 2017-04-13 | 2022-10-21 | 株式会社日本触媒 | 生体適合性医療用材料 |
CN111356422B (zh) | 2017-09-20 | 2022-08-09 | 西诺普西斯外科股份有限公司 | 鼻旁窦流体进入植入工具、组件、套件及方法 |
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US20140120146A1 (en) | 2014-05-01 |
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