JP2006512427A - 迅速に硬化する組成物 - Google Patents

迅速に硬化する組成物 Download PDF

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JP2006512427A
JP2006512427A JP2004548470A JP2004548470A JP2006512427A JP 2006512427 A JP2006512427 A JP 2006512427A JP 2004548470 A JP2004548470 A JP 2004548470A JP 2004548470 A JP2004548470 A JP 2004548470A JP 2006512427 A JP2006512427 A JP 2006512427A
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polyol component
diisocyanate
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マーク ロビー，
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タイコ ヘルスケア グループ エルピー
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Abstract

迅速に硬化する外科手術用接着剤接着剤およびシーラントは、芳香族ジイソシアネートおよびポリオールから誘導されたＮＣＯ末端親水性ウレタンプレポリマーを含む。ＮＣＯ末端親水性ウレタンプレポリマーを調製するために用いられる実質的に全ての芳香族ジイソシアネートは、パラ形態である。必要に応じて、この芳香族ジイソシアネートは、少なくとも１つの電子吸引基（例えば、フッ素基）で置換されている。この芳香族ジイソシアネートは、ｐ−フェニレンジイソシアネート、２，４−トリレンジイソシアネート（ＴＤＩ）、ジフェニルメタン−２，４’−ジイソシアネート（ＭＤＩ）およびｐ イソシアナトフェニルスルホニルイソシアネートからなる群より選択され得る。

Description

（背景）
（１．技術分野）
本開示は、外科手術用接着剤およびシーラントに関する。より詳細には、本開示は、芳香族ジイソシアネートに基づく、迅速に硬化する生体適合性組成物に関する。
（２．関連技術の説明）
近年、縫合糸を接着剤ボンドで置換するかまたは強化することについての興味がますます高まっている。この興味が高まったことの理由としては、以下が挙げられる：（１）修復が達成され得る潜在的速度；（２）結合物質が完全な閉鎖をもたらし、それにより流体の浸出を防止する能力；および（３）組織の過度の変形を伴うことなく結合を形成する可能性。
しかし、この領域での研究は、外科手術用接着剤が外科医によって受け入れられるためには、これらは多数の特異性を保有しなければならないことを示した。第１に、これらは、生存組織に対する高い粘着性および迅速結合能を示さなければならない。第２に、結合の強さは、結合の破損の前に組織の破損を引き起こすに充分に高くなければならない。第３に、この接着剤は、架橋の形態、好ましくは透過性の可撓性架橋を形成するべきである。第４に、この接着剤の架橋および／またはその代謝産物は、局所での組織毒性効果も発癌効果も引き起こさないべきである。
多数の接着剤系（例えば、アルキルシアノアクリレート、ポリアクリレート、無水マレイン酸／メチルビニルエーテル、エポキシ系、ポリビニルアルコール、ホルムアルデヒドおよび／またはグルタルアルデヒド樹脂ならびにイソシアネート）は、可能な外科手術用接着剤として調査されている。いずれも、受け入れられていない。なぜなら、各々が、上記の規準のうちの１以上を満たさないからである。これらの系の主な批判は、これらが提起する毒性問題の可能性である。
イソシアネートに基づく接着剤／シーラント組成物は、例えば、米国特許第５，１７３，３０１号；同第４，９９４，５４２号；および同第４，７４０，５３４号に開示されており、これらの開示は、その全体が、本明細書中に参考として援用される。
米国特許第５，１７３，３０１号明細書 米国特許第４，９９４，５４２号明細書 米国特許第４，７４０，５３４号明細書
新規の代謝的に受け入れられ得る、生体吸収性の、ジイソシアネートに基づく接着剤、特に、代謝的に受け入れられ得る、外科手術用接着剤を提供することが所望される。生分解性であり、代謝的に受け入れられ得る外科手術用接着剤を提供することもまた所望される。それらの物理的特性の結果として、毒性が低く、新規の、代謝的に受け入れられ得る外科手術用接着剤の使用によって生存組織において創傷を閉じるための方法を提供することもまた所望される。
（要旨）
本発明の外科手術用接着剤およびシーラント組成物は、芳香族ジイソシアネートおよび親水性ポリエーテルポリオールから誘導されたＮＣＯ末端親水性ウレタンプレポリマーを含む。ＮＣＯ末端親水性ウレタンプレポリマーを調製するために用いられる実質的に全ての芳香族ジイソシアネートは、パラ形態である。必要に応じて、この芳香族ジイソシアネートは、少なくとも１つの電子吸引基で置換されている。
（好ましい実施形態の詳細な説明）
本発明の組成物において用いられるＮＣＯ末端親水性ウレタンプレポリマーは、（ａ）少なくとも１つの芳香族ジイソシアネートおよび（ｂ）少なくとも１つの親水性ポリエーテルポリオールから誘導される。
芳香族ポリイソシアネートの適切な例は、ＮＣＯ基中に炭素原子を含まず、６〜２０個の炭素原子を含むものである。用いられる実質的に全ての芳香族ジイソシアネートは、パラ配置にある。用語「実質的に全ての」によって、少なくとも８０モルパーセントのジイソシアネートがパラ形態にあることを意味する。好ましくは、用いられる芳香族ジイソシアネートの９５モルパーセントがパラ配置にある。適切な芳香族ジイソシアネートとしては、ｐ−フェニレンジイソシアネート（ここでは以後、ＰＤＩという）、２，４−トリレンジイソシアネート（ＴＤＩ）、ジフェニルメタン−２，４’−ジイソシアネート（ＭＤＩ）、ｐイソシアナトフェニルスルホニルイソシアネートなどが挙げられるがこれらに限定されない。
必要に応じて、この芳香族ジイソシアネートは、１以上の電子吸引基で置換される。適切な電子吸引基としては、ハロゲン（例えば、フッ素または塩素）、カルボニル、カルボキシル、ニトリル、ニトロｍ、ホスホネート基またはホスフェートエステル基が挙げられる。このジイソシアネートは、１〜４のうちのどれかの電子吸引基で置換され得る。フッ素は、特に有用な電子吸引基であり、特に、ジイソシアネートが完全に置換された場合（すなわち、４つのフッ素基を有する）に有用な電子吸引基である。Ｆ含有ポリイソシアネートは、Ｊ．Ｍａｃｒｏｍｏｌ．Ｓｃｉ．−Ｐｈｙｓ．，ＢＩ，８３１（１９６７）および特開昭５７−１０８０５５／１９８２号に記載の方法に従って生成され得る。これらの開示は、本明細書中に参考として援用される。
適切な親水性ポリエーテルポリオール（ｂ）の例示は、エチレンオキシドまたは他のアルキレンオキシドを有するエチレンオキシドの組み合わせと、少なくとも２つの活性水素原子を含む１以上の化合物（例えば、多価アルコール、多価フェノール、アミン、ポリカルボン酸、亜リン酸など）との反応生成物である。多価アルコールの適切な例としては、以下が挙げられる：
二価アルコール（例えば、エチレングリコール、プロピレングリコール、１，３−および１，４− ブタンジオール、１，６−ヘキサンジオール、メチレン（ｎｅｈｔｙｌｅｎｅ）オキシドペンチルグリコール、ジエチレングリコール（ｑｌｙｃｏｌ）、ビス（ヒドロキシメチル）シクロヘキサン、ビス（ヒドロキシエチル）ベンゼン、水素化ビスフェノールＡ、水素化ビスフェノールＦ、ポリエテトラメチレングリコール、ポリエステルジオールおよびシラノール末端ポリシロキサン）；三価アルコール（例えば、グリセロール、トリメチロールプロパン、トリメチロールエタン、１，２，３−ブタントリオール、１，２，６−ヘキサントリオールおよびポリエステルトリオール）；ならびに４〜８またはそれより多くのヒドロキシル基を有する多価アルコー（例えば、ペンタエリスリトール、ジグリセロール、α−メチルグルコシド、ソルビトール、キシリトール、マンニトール、グルコース、フルクトース、スクロースなど）。適切な多価フェノールの例示は、単環式フェノールおよび多環式フェノール（例えば、ヒドロキノン、カテコール、レゾルシン、ピロガロール、およびビスフェノール（ビスフェノールＡ、ビスフェノールＦ、ビスフェノールＳなど）、ならびにフェノール−ホルムアルデヒド縮合生成物）である。適切なアミンとしては、以下が挙げられる：アンモニア；アルカノールアミン（例えば、モノ−、ジ−およびトリ−エタノールアミン、イソプロパノールアミンなど）；脂肪族、芳香族、アラリファティック（ａｒａｌｉｐｈａｔｉｃ）および脂環式のモノアミン（例えば、Ｃ１〜Ｃ２０のアルキルアミン（メチル−、エチル−、イソプロピル−、ブチル−、オクチル−、およびラウリル−アミンなど）、アニリン、トルイジン、ナフチルアミン、ベンジルアミン、シクロヘキシルアミンなど、脂肪族、芳香族、脂環式およびアラリファティックのポリアミン（例えば、Ｃ２〜Ｃ６のアルキレンジアミン（例えば、エチレンジアミン）、ジエチレントリアミン、トリレンジアミン、フェニレンジアミン、キシリレンジアミン、メチレンジアニリン、ジフェニルエーテルジアミン、イソホロンジアミン、シクロヘキシレンジアミン、ジシクロヘキシルメタンジアミンなど；ならびに複素環式ポリアミン（例えば、ピペラジン、Ｎ−アミノエチル−ピペラジンおよび他の複素環式ポリアミン）。
ポリエーテルポリオールを生成するためにエチレンオキシド（ｅｈｔｙｌｅｎｅ ｏｘｉｄｅ）と組み合わせて用いられ得る適切なアルキレンオキシドとしては、例えば、プロピレンオキシド、１，２−、２，３−、１，３−、および１，４−ブチレンオキシド、スチレンオキシド、エピクロロヒドリンなど、ならびにこれらのうちの２以上の組み合わせが挙げられる。
エチレンオキシドまたはアルキレンオキシドとのそれらの組み合わせを、活性水素原子含有化合物に付加することは、触媒（例えば、アルカリ性触媒、アミン触媒または酸性触媒）を用いて、または触媒を用いずに、通常の圧力または上昇した圧力下で、単一工程または複数段階のプロセスにおいて、任意の従来の溶液で実施され得る。エチレンオキシドおよびアルキレンオキシドの付加は、ランダム付加、ブロック付加またはそれらの組み合わせ（例えば、ランダム付加、続いてブロック付加）によって実施され得る。ランダム付加が好ましい。
親水性ポリエーテルポリオールは、１００〜５，０００ダルトン、好ましくは２００〜３，０００ダルトンの当量（ヒドロキシル基あたりの分子量）、および少なくとも３０重量％、好ましくは、５０〜９０重量％のオキシエチレン含有量を有利に有し得る。５，０００よりも高い当量を有するポリエーテルポリオールは、比較的高い粘度を有する組成物をもたらし得る。このことは、全てではないがいくつかの外科手術用接着剤適用については有用であり得る。一方、１００未満の当量は、比較的低い可撓性を有する組成物をもたらす。このことは、全てではないがいくつかの外科手術用接着剤適用については有用であり得る。不十分な親水性の性質を有する、３０重量％未満のオキシエチレン含有量のポリエーテルポリオールは、体液との乏しい反応性を有し得、このことはおそらく、治癒速度の低下および水が豊富な組織との乏しい結合力をもたらし得る。ポリエーテルポリオールの主なヒドロキシル基の含有量は、有利には、少なくとも３０％、より好ましくは少なくとも５０％、最も好ましくは少なくとも７０％であり得る。
ＮＣＯ末端ウレタンプレポリマーを生成するために用いられるポリオール（ｂ）全体は、適切には少なくとも３０重量％、好ましくは５０〜９０重量％のオキシエチレン含有量、適切には１００〜５，０００ダルトン、好ましくは２００〜３，０００ダルトンの平均当量、および適切には２〜８個のヒドロキシル基（平均）、好ましくは２〜４個のヒドロキシル基を有する。
芳香族ポリイソシアネート（ａ）と少なくとも１つの親水性ポリエーテルポリオール（ｂ）とを反応させてＮＣＯ末端親水性ウレタンプレポリマーを形成する際には、ＮＣＯ／ＯＨの比は、一般に１．５〜５．０、好ましくは１．７〜３．０である。プレポリマーを形成する（ａ）と（ｂ）との反応は、任意の従来の様式で実施され得る。この反応は、触媒の存在下で実施され得る。
本発明のＮＣＯ末端親水性プレポリマーのＮＣＯ含有量は、適切には１〜１０重量％、好ましくは２〜８重量％である。
本発明の接着剤またはシーラント組成物は、所望の場合、以下を含み得る：生理学的に活性な物質（例えば、抗微生物剤、局所麻酔剤、抗ヒスタミン剤アミン、消炎鎮静剤（ａｎｔｉｐｈｌｏｇｏｓｉｓａｎａｌｇｅｓｔｉｃｓ）、抗生物質、収斂剤、ビタミン、抗真菌剤、末梢神経系麻酔剤、血管拡張剤、ホルモン、生薬精油、チンキ剤、生薬粉末、低血圧剤など）；フィラー（例えば、カーボンブラック、金属酸化物（例えば、赤色酸化鉄および 二酸化チタン）、ケイ酸塩（例えば、ケイ酸カルシウムおよびケイ酸ナトリウム）、アクリル樹脂粉末、種々のセラミック粉末など）；柔軟剤（例えば、ＤＢＰ（リン酸ジブチル）、ＤＯＰ（リン酸ジオクチル）、ＴＣＰ（トリクレシルホスフェート）、トリブトキシエチルホスフェートおよび種々の型の他のエステル）；および安定剤（例えば、トリメチルジヒドロキノン、フェニル−β−ナフチルアミン、ｐ−イソプロポキシジフェニルアミン、ジフェニル−ｐ−フェニレンジアミンなど）。これらの添加物は、組成物の重量に基づいて２０％まで、好ましくは、５％までの量で用いられ得る。
ＮＣＯ末端プレポリマーは、微量の水（例えば、空気中の水分）の存在下で迅速に重合して、強靭な膜の形成をもたらす。従って、これらの主な成分および任意の他の配合添加物として乾燥した物質を用いることが好ましく、そして接着剤の生成の間中、水分を排除することが好ましい。このようにして得られた接着剤は、気密管（例えば、アンプル）中で長期間保存され得る。
本開示の接着剤を外科手術において適用する際に、適切な適用方法としては、ブラシ、ピンセット、アプリケータ、特別に設計されたへらまたはシリンジなどを用いる方法；ならびに不活性ガス（例えば、窒素など）を用いて噴霧コーティングすることを包含する方法が挙げられる。組織の結合は、以下によって達成され得る：接着剤を組織に単純に適用する直接的コーティング技術；ポリエステル（例えば、Ｄａｃｒｏｎ）、酸化セルロース、コラーゲン、ポリウレタンなど、綿様材料、または組織フラグメント（例えば、静脈、筋肉化（ｍｕｓｃｕｌａｔｉｏｎ）または筋肉膜（ｍａｓｃｕｌａｒ ｍｅｍｂｒａｎｅ）など）から作製された薄いシートまたはメッシュを止血または吻合の補助として用いる、カバーコーティング技術（ここで、これらの材料は、罹患部分に適用され、続いて接着剤がコーティングされる）；または縫合部分についてのシーリング技術（ここで、縫合糸は、部分的に適用され、続いて接着剤が適用されて、残りの結合部分が封止される）。これらの接着剤は、組織接着のためだけでなく、カテーテルによる直接的コーティングまたは注射を介した、心臓血管手術におけるコーティング材料、塞栓材料またはシーリング材料としても用いられ得る。適用可能な組織としては、例えば、血管、心臓、肺、食道、胃、肝臓、膵臓、脾臓、皮膚などが挙げられる。
芳香族ジイソシアネートおよび親水性ポリエーテルポリオールから誘導されたＮＣＯ末端親水性ウレタンプレポリマーを含む、本開示による外科手術用接着剤は、充分に高い硬化速度を有し、そして触媒がなくとも、組織に対する充分な結合力を提供する。
さらに、本開示の接着剤は、何の有機溶媒も用いずに、外科手術用接着剤に必要とされる、充分な硬化速度、組織に対する結合力、および身体の動きを許容する可撓性を提供し得る。
従って、外科手術に対する本開示の接着剤の適用は、従来の手術においての通りに縫合する代わりに、接着方法を用いて手術を実施することを可能にする。従って、これらは、医療技術における顕著な改善（例えば、手術時間の短縮化、止血、内臓などからの酵素漏出の予防、、微小血管閉塞の予防および神経吻合、ならびに縫合前の予備固定、ならびに接着剤と縫合との組み合わせによって結合を確実にすること）を獲得し得る。さらに、本発明の組成物は、手術においてだけでなく、例えば、切開した創傷または切断した部分の大きな連結部の医療処置、歯の外科手術における接着剤処置、生理学的に活性な物質と組み合わせた薬物の制御放出による治癒手段などにおいても、高い信頼性および高い効率を提供し得る。
種々の改変が、本明細書中に開示された実施形態に対して行われ得ることが理解される。それゆえ、上記の説明は、限定として解釈されるべきでなく、好ましい実施形態の単なる例示と解釈されるべきである。当業者は、添付の特許請求の範囲の範囲および精神内の他の改変物を予期する。

Claims (27)

  1. 接着剤組成物であって、該組成物は、少なくとも１つのＮＣＯ末端親水性ウレタンプレポリマーを含み、該プレポリマーは、（ａ）実質的に全てがパラ配置にある、芳香族ジイソシアネートおよび（ｂ）ポリオール成分から誘導される、接着剤組成物。
  2. 前記芳香族ジイソシアネートが、少なくとも１つの電子吸引基で置換されている、請求項１に記載の接着剤。
  3. 前記芳香族ジイソシアネートが、ｐ−フェニレンジイソシアネート（ここでは以後、ＰＤＩという）、２，４−トリレンジイソシアネート（ＴＤＩ）、ジフェニルメタン−２，４’−ジイソシアネート（ＭＤＩ）およびｐ イソシアナトフェニルスルホニルイソシアネートからなる群より選択される、請求項１に記載の接着剤。
  4. 前記芳香族ジイソシアネートが、少なくとも２つの電子吸引基で置換されている、請求項１に記載の接着剤。
  5. 前記芳香族ジイソシアネートが、４つの電子吸引基で置換されている、請求項１に記載の接着剤。
  6. 前記電子吸引基が、ハロゲン基、カルボニル基、カルボキシル基、ニトリル基、ニトロ基、ホスホネート基、ホスフェートエステル基およびそれらの組み合わせからなる群より選択される、請求項１に記載の接着剤。
  7. 前記電子吸引基が、フッ素基である、請求項１に記載の接着剤。
  8. 前記芳香族ジイソシアネートが、４つのフッ素基で置換されている、請求項１に記載の接着剤。
  9. 前記ポリオール成分が、ポリエーテルポリオールからなる群より選択される、請求項１に記載の接着剤。
  10. 前記ポリオール成分が、１以上のアルキレンオキシドと、少なくとも２つの活性水素原子を含む１以上の化合物との反応生成物である、請求項１に記載の接着剤。
  11. 前記ポリオール成分が、エチレンオキシドと、少なくとも２つの活性水素原子を含む１以上の化合物との反応生成物である、請求項１に記載の接着剤。
  12. 前記ポリオール成分が、１以上のアルキレンオキシドと、多価アルコール、多価フェノール、アミン、ポリカルボン酸および亜リン酸からなる群より選択される１以上の化合物との反応生成物である、請求項１に記載の接着剤。
  13. 前記ポリオール成分が、エチレンオキシド、プロピレンオキシド、１，２−ブチレンオキシド、２，３−ブチレンオキシド、１，３−ブチレンオキシド、１，４−ブチレンオキシド、スチレンオキシドおよびエピクロロヒドリンからなる群より選択される１以上のアルキレンオキシドと、少なくとも２つの活性水素原子を含む１以上の化合物との反応生成物である、請求項１に記載の接着剤。
  14. 前記ポリオール成分が、１００〜５，０００ダルトンの当量を有するポリエーテルポリオールからなる群より選択される、請求項１に記載の接着剤。
  15. 前記ポリオール成分が、適切には少なくとも３０％のオキシエチレン含有量を有するポリエーテルポリオールからなる群より選択される、請求項１に記載の接着剤。
  16. 抗微生物剤、局所麻酔剤、抗ヒスタミン剤、消炎鎮静剤、抗生物質、収斂剤、ビタミン、抗真菌剤、末梢神経系麻酔剤、血管拡張剤、ホルモン、生薬精油、チンキ剤、生薬粉末および低血圧剤からなる群より選択される１以上の生理学的に活性な物質をさらに含む、請求項１に記載の接着剤。
  17. カーボンブラック、金属酸化物、ケイ酸塩、アクリル樹脂粉末およびセラミック粉末からなる群より選択される１以上のフィラーをさらに含む、請求項１に記載の接着剤。
  18. リン酸ジブチル、リン酸ジオクチル、リン酸トリクレシルおよびリン酸トリブトキシエチルからなる群より選択される１以上の柔軟剤をさらに含む、請求項１に記載の接着剤。
  19. トリメチルジヒドロキノン、フェニル−β−ナフチルアミン、ｐ−イソプロポキシジフェニルアミンおよびジフェニル−ｐ−フェニレンジアミンからなる群より選択される１以上の安定剤をさらに含む、請求項１に記載の接着剤。
  20. 接着剤組成物であって、該組成物は、少なくとも１つのＮＣＯ末端親水性ウレタンプレポリマーを含み、該プレポリマーは、（ａ）実質的に全てがパラ配置にあって、少なくとも１つのフッ素基で置換されている、芳香族ジイソシアネート、および（ｂ）エチレンオキシドを含むポリオール成分から誘導される、接着剤組成物。
  21. 方法であって、少なくとも１つのＮＣＯ末端親水性ウレタンプレポリマーを含む接着剤組成物を組織に適用する工程を包含し、該プレポリマーが、（ａ）実質的に全てがパラ配置にある芳香族ジイソシアネート、および（ｂ）ポリオール成分から誘導される、方法。
  22. 接着剤組成物を適用する工程が、組織欠損上に該接着剤組成物を適用する工程を包含する、請求項２１に記載の方法。
  23. 接着剤組成物を適用する工程が、該接着剤組成物を適用して解剖学的管における欠損を封止する工程を包含する、請求項２１に記載の方法。
  24. 接着剤組成物を適用する工程が、肺組織における欠損上に該接着剤組成物を適用する工程を包含する、請求項２１に記載の方法。
  25. 接着剤組成物を適用する工程が、２つの組織表面を近づける工程、および該近づけた組織表面と接触させて該接着剤組成物を適用する工程を包含する、請求項２１に記載の方法。
  26. 接着剤を調製する方法であって、（ａ）実質的に全てがパラ配置にある芳香族ジイソシアネートと、（ｂ）ポリオール成分とを反応させて、プレポリマーを形成させる工程を包含する、方法。
  27. 芳香族ジイソシアネートとポリオール成分とを反応させる工程が、少なくとも１つの電子吸引基で置換されたジイソシアネートと、エチレンオキシドを含むポリオール成分とを反応させる工程を包含する、請求項２６に記載の方法。
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