JP2016006183A - 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
【解決手段】両親媒性コポリマーを含むシリコーン感圧接着剤組成物であって、両親媒性コポリマーは、ポリジメチル水素シロキサンまたはポリジメチルシロキサンベースのマクロイニシエーターに基づき、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、の組み合わせを用いて調製されるシリコーン感圧接着剤組成物。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)を含むシリコーン感圧接着剤組成物。
【選択図】なし
Description
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。
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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US11426485B2 (en) | 2022-08-30 |
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CA2766116C (en) | 2017-12-05 |
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US10294317B2 (en) | 2019-05-21 |
EP2451852A1 (en) | 2012-05-16 |
US20120108749A1 (en) | 2012-05-03 |
EP2451883A1 (en) | 2012-05-16 |
CA2766120A1 (en) | 2011-01-13 |
WO2011005846A1 (en) | 2011-01-13 |
JP2012532960A (ja) | 2012-12-20 |
US20180362690A1 (en) | 2018-12-20 |
JP6215874B2 (ja) | 2017-10-18 |
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