JP2012532960A - 感圧接着剤の適用のための両親媒性シリコーンコポリマー - Google Patents
感圧接着剤の適用のための両親媒性シリコーンコポリマー Download PDFInfo
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Abstract
Description
シリコーン感圧接着剤は、経皮的な薬剤送達、創傷包帯剤、瘢痕包帯剤、および他の健康管理の適用において広く使用される。これらの接着剤は、一般に、シリケート樹脂とポリジメチルシロキサン(PDMS)流体との縮合産物、またはビニルおよび水素化物含有PDMSとヒドロシリル化反応によって硬化したシリケート樹脂との反応性ブレンドである(非特許文献1)。これらの接着剤は、生体適合性で皮膚にやさしく、そして環境が乾燥しているときに医療装置を身体にしっかりと接着させる。しかしながら、皮膚の発汗中のような湿潤条件下では、疎水性シリコーン接着剤は、皮膚に対するその粘着性を失い、そのことは、包帯剤が時期尚早に身体からはずれることをもたらし得る。
本発明は、ポリジメチルシロキサンの1つまたはそれより多くの両親媒性コポリマーを含む感圧接着剤に関し、ここで上記コポリマーは、ポリジメチルシロキサンマクロイニシエーターまたはポリメチル水素シロキサンマクロイニシエーターと、少なくとも1つの反応性の親水性または両親媒性のモノマー、オリゴマー、マクロマー、およびそれらの組み合わせを用いて調製される。上記反応性の親水性または両親媒性のモノマーは、N−ビニルカプロラクタム、ビニルエステル、ビニルエーテル、不飽和の酸または無水物およびそれらの塩、アクリレート、メタクリレート、アクリルアミド、メタクリルアミド、N−アルキルアクリルアミド、シアン酸エステル、ヒドロキシアルキルアクリルアミド、グリシジルエステル、グリシジルエーテル、アリルモノマー、およびそれらの組み合わせからなる群から選択される。
ターポリマーの合成は、Crivelloら(J.V.Crivello,D.A.Conlon,and J.L.Lee,J.Polym.Sci.Part A:Polym.Chem.,24,1197−1215(1986))によって記載される手順に従って、PDMSマクロイニシエーターを用いる、無水マレイン酸とビニルエチルエーテルとの共重合(PDMS/MA/VEE)に基づいた(スキーム1)。本発明の独特さは、親水性の基をシロキサンポリマーへと組み込むことを含み、このシロキサンポリマーは、驚くべきことに、望ましい引きはがし粘着力、水分管理、および生体適合性を有する感圧接着剤に適しているポリマー添加剤をもたらす。
参考文献:J.V.Crivello,D.A.Conlon,and J.L.Lee,J.Polym.Sci.Part A:Polym Chem.,1197−1215(1986)
PDMS−水素化物を、シクロヘキセンオキシド(ここで例として示す)、グリシジルメチルエーテルなどのようなオキシラン含有化合物と反応させて、両親媒性PDMSコポリマーを合成する。
PDMS/MA/VEEターポリマーの特徴づけ
溶解性調査を、重水素化メタノール、2−プロパノール、およびトルエンにおいて実施した。2−プロパノール、および重水素化メタノール中では、ターポリマーは部分的な溶解性を示したが、主に懸濁物として残留し、トルエン中では、ターポリマーは不溶性であった。しかし、トルエン/2−プロパノール(1:1の比)混合物中で、ターポリマーは完全に溶解し、ターポリマーにおける極性鎖セグメントおよび非極性鎖セグメントの両方の存在を示した。ターポリマーサンプルは、希釈したアルカリ溶液に浸されたときにいくらかの膨張を示した。
ポリ(メチル水素シロキサン)−コ−PDMS−g−ポリ(シクロヘキセンオキシド)(PMDS−g−CHO)およびポリ(メチル水素シロキサン)−コ−PDMS−g−ポリ(グリシジルメチルエーテル)(PMDS−g−CHO)の合成
ポリ(メチル水素シロキサン)上へのシクロヘキセンオキシドのグラフト重合
ポリ(メチルシロキサン)上へのシクロヘキセンオキシドまたはグリシジルメチルエーテルのグラフト重合をトルエン中で実施した。モノマーおよび溶媒の両方を、水素化カルシウムで乾燥させた。マグネチックスターラーおよび還流凝縮器を備えた乾燥した250mLのフラスコに、50mLの乾燥トルエン、12g(0.12mol)のシクロヘキセンオキシドまたはグリシジルメチルエーテル、および8.0gのメチルヒドロシロキサン−ジメチルシロキサンコポリマー(GelestからのHMS−064;分子量55000〜65000、Si−H:5mol%〜7mol%)を窒素雰囲気下で導入した。溶解後、0.627gのAshby触媒を添加した。反応物を25℃にて約12時間静置した。この時間の終わりに、グラフトコポリマーを、メタノールで沈殿させ、減圧下で室温にて乾燥させた。
図1および2は、ターポリマーについてのNMRスペクトルを示す。2つのターポリマーサンプルは、同様のシグナルを示した。4.89ppm、3.92ppm、および1.13ppmでの大きいシグナルは、2−プロパノール溶媒に起因する。7.08ppm、6.98ppm、および2.12ppmでのシグナルは、トルエン−d8溶媒に起因する。0.14ppmでの鋭いシグナルは、サンプル材料からのPDMSに起因する。無水マレイン酸およびビニルエチルエーテルの交互コポリマーのソフトウェア予測は、1.1ppm、1.6ppmでのシグナル、および3.3ppmと3.4ppmとの間の3つのシグナルを予測している。1.1ppmに存在するあらゆるシグナルは、より極めて大きな2−プロパノールのシグナルによって不明瞭である。1.6ppmで予測されたシグナルもまた観測されず、それが予測より高磁場へシフトしている場合は溶媒によって不明瞭であり得る。シグナルは3.62ppmおよび3.50ppmで観測され、MA/VEE単位に対応するようである。3番目のシグナル、およびことによると4番目のシグナルを表す3.2ppm周辺にブロードシグナルがある。図3は、2つのスペクトルを重ね合わせたもの(overlay)を示し、サンプルPDMSシグナル強度が等価であると判断される。この図において、3.62ppmと3.2ppmとの間のシグナルが、PDMS/MA/VEE(2/2/2)ターポリマーよりもPDMS/MA/VEE(2/1/1)ターポリマーにおいて高いことがはっきりと示され、このことは、決められたターポリマー比に基づく予想と一致する。これらのサンプルにおけるMA/VEEが、無水マレイン酸およびビニルエチルエーテルの交互コポリマーであると仮定する場合、3.62ppm、3.50ppm、および3.2ppmでの3つのシグナルは、コポリマー由来の5個のプロトンと一致し、MA/VEE対PDMSの比が計算され得る。これらの計算の結果を表2に示す。
ポリジメチルシロキサンは、シリカの形成に起因して、大気中で炭をもたらすことが知られている。ほとんどの炭化水素ベースの化合物は、大気中で完全に酸化し、一切の残留物を残さない。これを実証するために、無水マレイン酸/ビニルメチルエーテルの市販のコポリマーであるGantrezTM AN−169(ISP Corporation)を、同じ条件を使って分析した(図5を参照のこと)。予想されたように、このコポリマーは、一切の炭を示さなかった。コポリマーの分解プロフィールは、4つのはっきりとした領域を有するターポリマーのより低温の分解プロフィールと一致する。これは、ターポリマー系におけるビニルエーテルおよび無水マレイン酸のコモノマーの存在を示す。ターポリマー系の炭化水素部分の予想される炭化はないので、残留物の量は、ターポリマー中のPDMSの量に関連すると仮定される。ターポリマー中のPDMSの量を、ターポリマーとニートの前駆体との間の炭重量の比を得ることによって計算した。これらの計算に基づいてターポリマー中のPDMSの重量パーセントを計算すると、20%未満であった(表2)。これは、反応器への初期投入量およびNMR分析から基づいて予想されたものよりもずいぶん低い。これらの相違は、炭化水素コモノマーの存在下でのシロキサン鎖の変えられた炭化メカニズムに起因し得る。
図10は、PDMS前駆体(一番下の曲線)と重ね合わせたPDMS/MA/VEEターポリマーについてのFTIRスペクトルを示す。前駆体は、1258cm−1(Si−CH3)、1067cm−1および1013cm−1(Si−O−Si伸縮振動)、ならびに793cm−1(Si−C伸縮およびCH3横揺れ)でのPDMSについてのフィンガープリントバンドを示す。ターポリマーは、1856cm−1および1781cm−1でのはっきりとしたバンドを示し、これは無水物基によるものであり得る。図11に提供される無水マレイン酸/ビニルメチルエーテル(ISP corporationからのGantrezTMAN−169)の参照スペクトルは、図10におけるターポリマーサンプルに対して高い一致を示す。これは、コポリマーにおけるPDMS部分およびMA/VEE部分の存在を確かにする。
両親媒性シリコーンPSAの特性:粘着性および透湿度(MVTR)
20wt%の充填レベルでPDMS/MA/VEEターポリマーを従来のシリコーンゲル接着剤へと、ゲルを硬化する前にブレンドすることによって両親媒性シリコーン感圧接着剤を調製した。反応性ブレンドを、次に、Werner−Mathisコーターを用いてポリウレタンフィルム上にコーティングし、150℃で3分間硬化させた。コーティングの厚みは約10ミルであった。接着剤の透湿度(MVTR)を、直立カップ法(upright cup method)ASTM E96−00を用いて測定した。表3は、ニートのシリコーンゲル接着剤と比較した、粘着性および透湿度の変化(%)の概要を示す。両親媒性コポリマー添加剤を有する組成物は、触ると粘着性であるので、依然として感圧接着剤であり、そしてMVTRは、ニートのシリコーンゲルと比較して約800%の増加を示した。
Claims (5)
- ポリジメチルシロキサンの1つまたはそれより多くの両親媒性コポリマーを含む感圧接着剤であって、ここで該コポリマーは、ポリジメチルシロキサンマクロイニシエーターまたはポリメチル水素シロキサンマクロイニシエーターと、少なくとも1つの反応性の親水性または両親媒性のモノマー、オリゴマー、マクロマー、およびそれらの組み合わせを用いて調製される、感圧接着剤。
- 前記反応性の親水性または両親媒性のモノマーが、N−ビニルカプロラクタム、ビニルエステル、ビニルエーテル、不飽和の酸または無水物およびそれらの塩、アクリレート、メタクリレート、アクリルアミド、メタクリルアミド、N−アルキルアクリルアミド、シアン酸エステル、ヒドロキシアルキルアクリルアミド、グリシジルエステル、グリシジルエーテル、アリルモノマー、およびそれらの組み合わせからなる群から選択される、請求項1に記載の感圧接着剤。
- 前記反応性の親水性または両親媒性のオリゴマーおよびマクロマーが、ビニル、エポキシ、アリル、およびそれらの組み合わせから選択される反応性の基を有する、ポリアルキレンオキシド、ポリエーテル、ポリウレタン、ポリエステル、ポリアミド、多糖類、ポリペプチド、ポリアクリレート、ポリメタクリレート、ポリアクリルアミドからなる群から選択される、請求項1に記載の感圧接着剤。
- ポリ(ジメチルシロキサン)−ポリ(無水マレイン酸−ビニルエチルエーテル)(PDMS/MA/VEE)の1つまたはそれより多くの両親媒性コポリマーおよび一緒にブレンドされるシリコーンゲル接着剤を含む、請求項1に記載の感圧接着剤。
- ポリジメチルシロキサンの1つまたはそれより多くの両親媒性コポリマーを含む感圧接着剤を含む医療装置であって、ここで該コポリマーは、ポリジメチルシロキサンマクロイニシエーターまたはポリメチル水素シロキサンマクロイニシエーター、および少なくとも1つの反応性の親水性または両親媒性のモノマーまたはオリゴマーまたはマクロマーを用いて調製される、医療装置。
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AU2010270610B2 (en) | 2015-05-07 |
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US20120109036A1 (en) | 2012-05-03 |
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WO2011005839A1 (en) | 2011-01-13 |
EP2451883A1 (en) | 2012-05-16 |
EP2451883B1 (en) | 2019-04-17 |
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