JP2009518129A - 生体吸収性外科用組成物 - Google Patents
生体吸収性外科用組成物 Download PDFInfo
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- JP2009518129A JP2009518129A JP2008544476A JP2008544476A JP2009518129A JP 2009518129 A JP2009518129 A JP 2009518129A JP 2008544476 A JP2008544476 A JP 2008544476A JP 2008544476 A JP2008544476 A JP 2008544476A JP 2009518129 A JP2009518129 A JP 2009518129A
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- Prior art keywords
- bioabsorbable
- diisocyanate
- macromer composition
- group
- functional
- Prior art date
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Abstract
Description
この出願は、2005年12月6日に出願された米国仮特許出願第60/742,708号(この全体の開示が本明細書に参考として援用される)の利益を主張する。
本開示は、マトリクスを形成し得る生体吸収性マクロマーおよび外科手術用接着剤またはシーラントとしてのこれらマクロマーの使用に関する。
近年、縫合を接着剤ボンドで代用または増強することに関心が高まっている。関心が高まった理由として(1)修復が成功し得る潜在的な速度;(2)完全閉鎖をもたらす結合物質の能力、つまり流体の漏出を防ぐ能力;および(3)組織が異常変形することなしに接合を形成する可能性が挙げられる。
本開示は、少なくともひとつの官能基を有するポリオールと任意に結合したジイソシアネート官能性生体吸収性ポリマーを含む、生体吸収性マクロマー組成物に関する。実施形態において、生体吸収性ポリマーは、生体吸収性基(bioabsorbable group)を包含するポリアルキレンオキシドである。
R2−[A]m−R3−[A]m−R2
のジイソシアネート官能性生体吸収性ポリマーを含み得り、式中、Aはラクチド、グリコリド、ε−カプロラクトン、トリメチレンカーボネート、p−ジオキサノン、無水物基、リン酸エステルおよびこれらの組み合わせなどの生体吸収性基であり、R3はポリエチレングリコールであり、R2はイソシアネート基であり、mは約1〜約6の数である。
R2−[A]v−R1−[A]v−R2
のジイソシアネート官能性生体吸収性ポリマーを含み得り、式中、R1は多糖およびポリオールなどのポリマーであり、Aは生体吸収性基であり、R2はイソシアネート基およびvは少なくともひとつの官能基を有するポリオールと結合した約1〜約20の数である。
本開示は、生体適合性であり、非免疫原生であり、生分解性である組織接着剤またはシーラントとして使用するためのマクロマー組成物に関する。生体吸収性マクロマー組成物は、組織端を接着、組織の空気/流体漏れを密閉、組織へ医療機器すなわちインプラントを接着および組織増殖のため、組織において密閉または隙間もしくは不備を埋めるため使用できる。生体吸収性マクロマー組成物は、生体組織および/またはヒトを含む動物の肉体に適用できる。
R1−(OH)n (I)
式中、R1は多糖およびポリオールから選ばれた基の員であり、nは約1〜約20の数である複数のヒドロキシ基を有するポリマーを形成するため、ポリマーをD−ソルビトール、D−マンニトール、トリス(ヒドロキシメチル)アミノメタン(また周知の2−アミノ−2−(ヒドロキシメチル)−1,3−プロパンジオール)、エンテロジオール、シクロデキストリン等などの多価アルコールと1次反応させることにより、ジイソシアネート官能性ポリマーに組み込まれ得る。好適な多糖は、限定されるものではないが、ソルビトール、マンニトール、スクロース、デキストラン、シクロデキストリン等を含む。好適なポリオールは、限定されるものではないが、ポリアルキレンオキシド、ポリビニルアルコール等を含む。
R2−[A]v−R1−[A]v−R2 (II)
であって、式中、R1は多糖またはポリオールであり、R2はジイソシアネート基を含むイソシアネート基であり、Aは生体吸収性基およびvは約1〜約20、実施形態において、約1〜約6の数である。一実施形態において、R1はポリエチレングリコールなどのポリアルキレンオキシドであり得、Aはラクチド、グリコリド、ε−カプロラクトン、炭酸トリメチレン、p−ジオキサノン、無水物、リン酸エステルまたはこれらの組み合わせであり得る。
R2−[A]m−R3−[A]m−R2 (III)
を有し、式中、AおよびR2は前記定義の通りであり、R3はPEGであり、mは約1〜約6の数である。
[R5−O]3−R4 (IV)
式中、R5はジイソシアネートであり、R4はポリカプロラクトンである。
R7−[(R8)n−R9]d (VII)
を有し、式中、R7はポリオールであり、R8は生体吸収性基であり、R9はジイソシアネート基を含むイソシアネート基であり、nは約1〜約10の数でありおよびdは約2〜約4の数である。
R10−R7−[(R8)n−R9]d (VIII)
を保有し、式中、R10はmPEGであり、R7、R8、R9、nおよびdは上記定義の通りである。
ヘキサメチレンジイソシアネート(HMDI)との濃縮によるメトキシ−PEGSの活性化。HMDIを、mPEGおよびクロロホルム中のトリエチルアミン(触媒)(J.T.Baker)の溶液に加えた。反応混合物(10%w/v)を、60〜65℃(沸点=61℃)で4〜6時間還流させながら加熱した。ポリマーmPEG−NCOを、1:1の割合で石油エーテル/ジエチルエーテル(PE/エーテル)中に沈殿させることによって分離した。PE/エーテルで洗浄し、再沈殿を2回繰り返した。最終生成物を真空乾燥した。収量:>90%。解析:核磁気共鳴法(NMR)、フーリエ変換赤外分光法(FTIR)、示差走査熱量測定法(DSC)。
mPEG−OCONH(CH2)6−NCOおよびD−ソルビトールの濃縮。D−ソルビトールをN,N−ジメチルホルムアミド(DMF)で溶解し(わずかに加熱しながら)、その後mPEG−OCONH(CH2)6NCO(分子量=2000または5000)およびクロロホルム中に溶解しているトリエチルアミンの溶液に、攪拌しながら室温で滴下にて加えた。反応温度を、室温から約60〜65℃に上昇させ、反応は6〜8時間続いた。沈殿物が発生したなら、さらなるDMFに物質を再融解するために加えた。反応混合物は、ROTAVAPOR(登録商標)ロータリーエバポレータ(BUCHI Labortechnik AG)で濃縮され、その後PE/エーテル中で沈殿した。最終生成物を窒素存在下で真空乾燥した。収量:>80%。解析:NMR、FTIR、DSC。
L−ラクチドの開環塊状重合(ROP)。メトキシ−PEG−OCN(CH2)6NH−CO−NH−D−ソルビトール−(OH)5、開始剤およびL−ラクチドをN2存在下で135〜140℃まで加熱した。Sn(Oct)2、触媒を、最小量のトルエンで溶解(約1mL)し、融成物へ加えた。反応温度は約135〜140℃で、反応を15時間続けた。反応混合物はクロロホルムで溶解し、その後石油エーテル/ジエチルエーテル(比率1:1)中で沈殿した。最終生成物を真空乾燥した。収量:>60%。解析:NMR、FTIR、DSC。
ヘキサメチレンジイソシアネート(HMDI)によるmPEG−OCONH(CH2)6NH−D−ソルビトール−(ポリラクチド−OH)5の濃縮。メトキシ−PEG−OCONH(CH2)6NH−D−ソルビトール−(ポリラクチド−OH)5およびトリエチルアミン(触媒)を室温にてクロロホルムで溶解した。この溶液を、室温にて攪拌されたクロロホルム中のHMDI溶液へ徐々に加えた。濃縮反応は、窒素存在下にて6時間還流温度で行った。ROTAVAPOR(登録商標)ロータリーエバポレータを使用して溶媒の減少後、続いて石油エーテル/ジエチルエーテル(比率1:1)中で沈殿した。最終生成物を窒素存在下で真空乾燥した。収量:>90%。解析:NMR、FTIR、DSC。
プロピレングリコールを使用するラクチドの開環重合
25.92グラムのラクチド(LA;Puracより)および2.3グラムのプロピレングリコール(PG;JT Bakerより)を、清潔で乾燥した250mlの丸底フラスコ中で混合した。少量のトルエンで溶解した0.021グラムのオクチル酸スズを加えた。反応混合物を、静的な窒素大気下で攪拌しながら15〜18時間、135〜140℃で加熱した。結果として生じた構造物(HO−(LA3)−PG−(LA3)−OH)を、NMRを使用して確認した。
HMDIを室温にて、実施例5(HO−(LA3)−PG−(LA3)−OH)の生成物およびテトラヒドロフラン(THF)中のトリエチルアミン(TEA)の溶液へ加えた。反応混合物を、還流するため4時間加熱(約65℃)し、その後室温にてひと晩放置した。結果として生じた物質を、THF中のPEG400溶液へ加えた。
官能性ポリオールは、以下のように調製された。HMDIを、ポリカプロラクトンジオール、ポリカプロラクトントリオールおよびTEA(200〜250ml)を含むTHF溶液へ加えた。反応混合物を4時間還流し、その後ひと晩攪拌しながら室温に冷却した。結果として生じた物質を、THF(200〜250ml)中のPEG200溶液へ加え、4時間還流した。結果として生じたポリオールを、PE/エーテル(比率1:1)中の沈殿によって分離した。収量は99%であった。解析はNMRであった。
25.5グラムのグリコリド(「G」)、25.0グラムのカプロラクトン(「CL」)および1.67グラムのプロピレングリコールを、清潔で乾燥した500mlの2口丸底フラスコへ加えた。物質を混合し、窒素泡沸でひと晩乾燥させた。乾燥後、物質を静的な窒素下に置き、引き続き混合しながら150℃に加熱した。物質が150℃に到達するとすぐに、0.04グラムのオクチル酸スズを加え、混合物を24時間反応させた。サンプルを得、NMRおよびIRで検査した。その後混合物をその後130℃に冷却した。
上述の実施例8で産生した82.50グラムの分離性ポリ(グリコリド−カプロラクトン)−PEO/PPO共重合体物質を85.5グラムのHMDIと混合した。その物質を120℃に加熱し、静的な窒素下で21時間、100RPMで混合した。その後、生成物を次のように石油エーテルで抽出した。約100グラムの生成物および約300mlの石油エーテルを冷却器を備えている1口フラスコに加えた。攪拌された混合物を還流温度に加熱し、30分間その温度で保った。その後、混合物を室温に冷却し、溶媒を別の容器へ静かに移した。この作業を、未反応のHMDIの抽出を確実にするためにもう2回繰り返した。抽出された物質、HMDI−官能性分離性ポリ(グリコリド−カプロラクトン)−PEO/PPO共重合体物質を、その後1トル以下の圧力で、少なくとも24時間真空乾燥した。
Claims (22)
- 一般式:
R2−[A]m−R3−[A]m−R2 (III)
であって、式中、Aはラクチド、グリコリド、ε−カプロラクトン、炭酸トリメチレン、p−ジオキサノン、無水物、リン酸エステルおよびこれらの組み合わせからなる群より選択される生体吸収性基であり、R3はポリエチレングリコール、R2はイソシアネート基およびmは約1〜約6の数である、ジイソシアネート官能性生体吸収性ポリマーを含む生体吸収性マクロマー組成物。 - 一般式:
R2−[A]v−R1−[A]v−R2 (II)
であって、式中、R1は多糖およびポリオールからなる群より選択されるポリマーであり、Aは生体吸収性基であり、R2はイソシアネート基でありおよびvは約1〜約20の数であるジイソシアネート官能性生体吸収性ポリマー;および少なくとも1つの官能性ポリオール;を含む生体吸収性マクロマー組成物。 - 前記ジイソシアネート官能性生体吸収性ポリマーのポリオールが、ポリエチレンオキシド、ポリエチレングリコール、ポリプロピレングリコール、ポリエチレンオキシド−ポリプロピレンオキシド共重合体、ポリエチレングリコール−アジピン酸塩、ポリエチレングリコール−ポリプロピレングリコール共重合体およびこれらの組み合わせからなる群より選択される、請求項2に記載の生体吸収性マクロマー組成物。
- 前記ジイソシアネート官能性生体吸収性ポリマーのポリオールが、ポリエチレングリコールを含む、請求項2に記載の生体吸収性マクロマー組成物。
- 前記ジイソシアネート官能性生体吸収性ポリマーの多糖が、ソルビトール、マンニトール、スクロース、デキストランおよびシクロデキストリンからなる群より選択される、請求項2に記載の生体吸収性マクロマー組成物。
- 前記ジイソシアネート官能性生体吸収性ポリマーの生体吸収性基が、乳酸、グリコール酸、グリコリド、ラクチド、ε−カプロラクトン、炭酸トリメチレン、1,4−ジオキサン−2−オン、1,3−ジオキサン−2−オン、コハク酸(succinnic acid)、アジピン酸、セバシン酸、マロン酸、グルタル酸、アゼライン酸、ジクロロリン酸エチル、セバシン酸無水物、アゼライン酸無水物およびこれらの組み合わせからなる群より選択される、請求項2に記載の生体吸収性マクロマー組成物。
- 前記ジイソシアネート官能性生体吸収性ポリマーの生体吸収性基が、ラクチド、グリコリド、ε−カプロラクトン、p−ジオキサノン、炭酸トリメチレンおよびこれらの組み合わせからなる群より選択される、請求項2に記載の生体吸収性マクロマー組成物。
- vが、約1〜約6の数である、請求項2に記載の生体吸収性マクロマー組成物。
- 前記官能性ポリオールが、ポリエーテルをベースとしたポリオール、ポリカプロラクトンをベースとしたポリオールおよび多価アルコールからなる群より選択される、請求項2に記載の生体吸収性マクロマー組成物。
- 前記官能性ポリオールが、ポリカプロラクトントリオール、トリメチロールプロパンおよびグリセリンからなる群より選択される、請求項9に記載の生体吸収性マクロマー組成物。
- 前記官能性ポリオールが、ジイソシアネート官能基を保有する、請求項2に記載の生体吸収性マクロマー組成物。
- 前記官能性ポリオールが、トルエンジイソシアネート、4,4’−ジフェニルメタンジイソシアネート、4,4’−オキシビス(フェニルイソシアネート)、2,4,6−トリメチル−1−、3−フェニレンジイソシアネート、トリメチルヘキサンジイソシアネート、1,6−ヘキサメチレンジイソシアネートおよびイソホロンジイソシアネートからなる群より選択される、ジイソシアネート官能基を保有する、請求項12に記載の生体吸収性マクロマー組成物。
- 前記官能性ポリオールが、メトキシポリエチレングリコールで官能化したソルビトールを含む、請求項9に記載の生体吸収性マクロマー組成物。
- 前記官能性ポリオールが、乳酸、グリコール酸、グリコリド、ラクチド、ε−カプロラクトン、炭酸トリメチレン、1,4−ジオキサン−2−オン、1,3−ジオキサン−2−オン、コハク酸(succinnic acid)、アジピン酸、セバシン酸、マロン酸、グルタル酸、アゼライン酸、ジクロロリン酸エチル、セバシン酸無水物、アゼライン酸無水物およびこれらの組み合わせからなる群より選択される、生体吸収性基を保有する、請求項9に記載の生体吸収性マクロマー組成物。
- 前記官能性ポリオールが、式
R7−[(R8)n−R9]d (VII)
であって、式中、R7はポリオールであり、R8は生体吸収性基であり、R9はイソシアネート基であり、nは約1〜約10の数でありおよびdは約2〜約4の数である、請求項9に記載の生体吸収性マクロマー組成物。 - 前記ポリオールがソルビトールを含み、前記生体吸収性基がラクチドを含み、そして前記生体吸収性マクロマー組成物が、生物学的に活性な因子、薬剤および酵素からなる群より選択される成分をさらに含む、請求項16に記載の生体吸収性マクロマー組成物。
- 創傷を閉鎖するための方法であって、該方法は、
請求項2に記載の生体吸収性マクロマー組成物を該創傷に適用する工程;および
該生体吸収性マクロマー組成物を硬化させ、それによって該創傷を閉鎖する工程を含む、方法。 - 前記創傷が、外科的切開である、請求項18に記載の方法。
- 動物組織の空隙を充填するための方法であって、該方法は、
請求項2に記載の生体吸収性マクロマー組成物を該空隙に適用する工程;および
該生体吸収性マクロマー組成物を硬化させ、それによって該空隙を充填する工程を含む、方法。 - 動物組織の表面へ医療機器を接着するための方法であって、該方法は、
請求項2に記載の生体吸収性マクロマー組成物を該機器、該表面またはそれらの両方に適用する工程;
該機器、生体吸収性マクロマー組成物および表面を互いに接触させる工程;ならびに
該生体吸収性マクロマー組成物を硬化させ、それによって該機器と表面とを互いに接着する工程を含む、方法。 - 前記医療機器が、インプラントである、請求項21に記載の方法。
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JP2010525152A (ja) * | 2007-04-24 | 2010-07-22 | タイコ ヘルスケア グループ リミテッド パートナーシップ | 生分解性マクロマー |
US9382386B2 (en) | 2012-12-06 | 2016-07-05 | Lg Chem, Ltd | Lactide copolymer, method for preparing same, and resin composition comprising same |
US9382385B2 (en) | 2012-12-06 | 2016-07-05 | Lg Chem, Ltd. | Lactide copolymer, and resin composition and film comprising same |
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---|---|---|---|---|
US7700819B2 (en) | 2001-02-16 | 2010-04-20 | Kci Licensing, Inc. | Biocompatible wound dressing |
US7763769B2 (en) | 2001-02-16 | 2010-07-27 | Kci Licensing, Inc. | Biocompatible wound dressing |
GB0116341D0 (en) * | 2001-07-04 | 2001-08-29 | Smith & Nephew | Biodegradable polymer systems |
GB0202233D0 (en) * | 2002-01-31 | 2002-03-20 | Smith & Nephew | Bioresorbable polymers |
GB0222522D0 (en) * | 2002-09-27 | 2002-11-06 | Controlled Therapeutics Sct | Water-swellable polymers |
EP1596765A2 (en) * | 2003-02-10 | 2005-11-23 | Smith & Nephew, Inc. | Resorbable devices |
US7141354B2 (en) * | 2003-09-30 | 2006-11-28 | Dai Nippon Printing Co., Ltd. | Photo radical generator, photo sensitive resin composition and article |
GB0329654D0 (en) | 2003-12-23 | 2004-01-28 | Smith & Nephew | Tunable segmented polyacetal |
GB0417401D0 (en) | 2004-08-05 | 2004-09-08 | Controlled Therapeutics Sct | Stabilised prostaglandin composition |
US20100100124A1 (en) * | 2005-05-05 | 2010-04-22 | Tyco Healthcare Group Lp | Bioabsorbable surgical composition |
US20090177226A1 (en) * | 2005-05-05 | 2009-07-09 | Jon Reinprecht | Bioabsorbable Surgical Compositions |
US8044234B2 (en) * | 2005-05-05 | 2011-10-25 | Tyco Healthcare Group Lp | Bioabsorbable surgical composition |
EP1922091A2 (en) * | 2005-08-18 | 2008-05-21 | Smith & Nephew, PLC | High strength devices and composites |
CA2628598C (en) * | 2005-12-06 | 2015-02-24 | Tyco Healthcare Group Lp | Bioabsorbable surgical composition |
WO2007103276A2 (en) | 2006-03-03 | 2007-09-13 | Smith & Nephew, Inc. | Systems and methods for delivering a medicament |
GB0613333D0 (en) | 2006-07-05 | 2006-08-16 | Controlled Therapeutics Sct | Hydrophilic polyurethane compositions |
GB0613638D0 (en) * | 2006-07-08 | 2006-08-16 | Controlled Therapeutics Sct | Polyurethane elastomers |
EP2037938A2 (en) * | 2006-07-12 | 2009-03-25 | Controlled Therapeutics (Scotland) Ltd. | Drug delivery polymer with hydrochloride salt of clindamycin |
GB0620685D0 (en) * | 2006-10-18 | 2006-11-29 | Controlled Therapeutics Sct | Bioresorbable polymers |
US8722783B2 (en) | 2006-11-30 | 2014-05-13 | Smith & Nephew, Inc. | Fiber reinforced composite material |
WO2008129245A1 (en) | 2007-04-18 | 2008-10-30 | Smith & Nephew Plc | Expansion moulding of shape memory polymers |
JP5520814B2 (ja) | 2007-04-19 | 2014-06-11 | スミス アンド ネフュー インコーポレーテッド | マルチモーダル形状記憶ポリマー |
ATE505220T1 (de) | 2007-04-19 | 2011-04-15 | Smith & Nephew Inc | Graft-fixierung |
US8952075B2 (en) * | 2008-05-22 | 2015-02-10 | Poly-Med, Inc. | Bioactive polymeric liquid formulations of absorbable, segmented aliphatic polyurethane compositions |
US20090265016A1 (en) * | 2008-04-21 | 2009-10-22 | Lasse Daniel Efskind | Material for surgical use in traumatology |
US20100092533A1 (en) * | 2008-10-15 | 2010-04-15 | Joshua Stopek | Bioabsorbable Surgical Composition |
JP2012529497A (ja) * | 2009-06-09 | 2012-11-22 | シーマス リミテッド | ハロゲン化脂肪族カルボン酸、そのオリゴマーおよび/またはポリマー、ならびに、表面的および内部の新生物を失活化することにおけるそれらの使用 |
CA2817192C (en) * | 2010-11-08 | 2018-05-01 | Sk Chemicals Co., Ltd. | Polylactic acid resin, preparation method thereof, and packaging film comprising the same |
WO2012066000A1 (en) * | 2010-11-15 | 2012-05-24 | Dsm Ip Assets B.V. | Intravaginal drug delivery device comprising a polyurethane copolymer |
US10016454B2 (en) | 2012-12-04 | 2018-07-10 | Cohera Medical, Inc. | Silane-containing moisture-curable tissue sealant |
US10472450B2 (en) * | 2016-03-09 | 2019-11-12 | The Government Of The United States Of America, As Represented By The Secretary Of The Navy | Acute care cover for severe injuries |
WO2019123389A1 (en) | 2017-12-20 | 2019-06-27 | Stryker European Holdings I, Llc | Biomedical foam |
JP2022124449A (ja) * | 2021-10-08 | 2022-08-25 | 健次朗 酒井 | 死後処置用品 |
CN115970043B (zh) * | 2022-09-09 | 2024-08-23 | 吉林大学 | 一种用于修复组织的黏合剂及其制备方法和应用 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS63278924A (ja) * | 1987-05-09 | 1988-11-16 | Bio Material Yunibaasu:Kk | 生体内分解吸収性ウレタンプレポリマ− |
JP2000514457A (ja) * | 1996-07-11 | 2000-10-31 | ライフ・メディカル・サイエンシーズ,インコーポレイテッド | 術後の癒着形成を減少または排除するための方法および組成物 |
WO2005100429A1 (en) * | 2004-04-15 | 2005-10-27 | The University Of Utah Research Foundation | Bioresponsive polymer system for delivery of microbicides |
JP2006519633A (ja) * | 2003-01-09 | 2006-08-31 | ポリガニックス ビー. ブイ. | 生体医用フォーム |
Family Cites Families (134)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2004A (en) * | 1841-03-12 | Improvement in the manner of constructing and propelling steam-vessels | ||
GB985144A (en) | 1962-03-27 | 1965-03-03 | Ici Ltd | Process for purification of isocyanate group-containing compounds |
DE1282962B (de) | 1966-04-28 | 1968-11-14 | Bayer Ag | Verfahren zur Herstellung waessriger sedimentierender redispergierbaren Dispersionen vernetzter, Harnstoffgruppe aufweisender Polyadditionsprodukte |
DE1720617A1 (de) | 1967-02-10 | 1971-07-01 | Bayer Ag | Verfahren zur Herstellung von Polyurethanpolyharnstoffen |
NL155858B (nl) | 1967-02-17 | 1978-02-15 | Ameliotex Inc | Werkwijze voor de bereiding van lineaire gesegmenteerde polyurethanen, alsmede gevormde voortbrengselen die uit aldus bereide polyurethanen zijn vervaardigd. |
DE2032297A1 (de) * | 1970-06-23 | 1971-12-30 | Schering Ag | Verfahren zum Verkleben von weichgemachten, chlorhaltigen Polymerisaten |
US3879493A (en) * | 1972-02-14 | 1975-04-22 | Cpc International Inc | Vapor permeable compositions |
US3903232A (en) * | 1973-10-09 | 1975-09-02 | Grace W R & Co | Dental and biomedical foams and method |
US3975550A (en) * | 1974-08-07 | 1976-08-17 | General Foods Corporation | Plastically deformable ready-to-use batter |
US4061662A (en) | 1975-08-28 | 1977-12-06 | W. R. Grace & Co. | Removal of unreacted tolylene diisocyanate from urethane prepolymers |
US4057535A (en) * | 1976-04-14 | 1977-11-08 | Tatyana Esperovna Lipatova | Adhesive for gluing together soft body tissues |
US4169175A (en) * | 1976-06-14 | 1979-09-25 | W. R. Grace & Co. | Removal of unreacted tolylene diisocyanate from urethane prepolymers |
US4132839A (en) * | 1976-10-12 | 1979-01-02 | W. R. Grace & Co. | Biodegradable hydrophilic foams and method |
SE417975B (sv) * | 1977-09-20 | 1981-04-27 | Gambro Dialysatoren | Forfarande for katalytisk utherdning av polyuretanformmassor i vilket man sasom fysiologiskt fordragbar herdningskatalysator anvender sorbinsyra eller kanelsyra |
AT366916B (de) | 1980-04-02 | 1982-05-25 | Immuno Ag | Vorrichtung zur applikation eines gewebeklebstoffes auf basis von menschlichen oder tierischenproteinen |
US4323491A (en) * | 1980-04-24 | 1982-04-06 | Veselovsky Roman A | Polyurethane adhesive composition |
US4361055A (en) | 1980-05-19 | 1982-11-30 | Juris Murnieks | Torque converter |
AU558611B2 (en) * | 1981-02-03 | 1987-02-05 | Bayer Aktiengesellschaft | Polyurethane gel |
US4425472A (en) * | 1981-06-22 | 1984-01-10 | Lord Corporation | Radiation-curable compositions |
US4419476A (en) | 1981-10-09 | 1983-12-06 | E. I. Du Pont De Nemours & Co. | Ternary adhesive systems |
US4451627A (en) * | 1982-09-07 | 1984-05-29 | The Dow Chemical Company | Addition polymerizable urethane-based anaerobic adhesives made from tin (II) organoesters |
US4511626A (en) * | 1982-09-09 | 1985-04-16 | Minnesota Mining And Manufacturing Company | One-part moisture-curable polyurethane adhesive, coating, and sealant compositions |
US4477604A (en) * | 1982-09-20 | 1984-10-16 | Oechsle Iii Sixtus J | Polyurethane compositions and their use as luting agents |
DE3329392A1 (de) * | 1983-08-13 | 1985-02-28 | Bayer Ag, 5090 Leverkusen | Thermisch verformbares konstruktionsmaterial, verfahren zu dessen herstellung und dessen verwendung |
US4725653A (en) * | 1983-10-27 | 1988-02-16 | Union Carbide Corporation | Low viscosity adducts of a polycaprolactone polyol and a polyepoxide |
JPS60152535A (ja) * | 1984-01-20 | 1985-08-10 | Ichiro Shibauchi | 架橋剤及びその製造方法 |
JPS6147775A (ja) * | 1984-08-14 | 1986-03-08 | Dainippon Ink & Chem Inc | 複合ラミネ−トフイルム用接着剤組成物 |
JPS61152765A (ja) * | 1984-12-27 | 1986-07-11 | Nippon Ekishiyou Kk | シクロデキストリン類で包接された化合物を含有した合成樹脂製品及びその製造方法 |
US4740534A (en) * | 1985-08-30 | 1988-04-26 | Sanyo Chemical Industries, Ltd. | Surgical adhesive |
EP0245858B1 (en) * | 1986-05-14 | 1992-07-29 | Takiron Co. Ltd. | Adhesive for percutaneous administration |
JPH0739457B2 (ja) * | 1986-05-14 | 1995-05-01 | タキロン株式会社 | 両親媒性セグメントポリウレタン |
DE3775208D1 (de) * | 1986-08-20 | 1992-01-23 | Teikoku Seiyaku Kk | Steroidenheilmittelzubereitung zur aeusserlichen verwendung. |
US5169720A (en) | 1986-11-18 | 1992-12-08 | W. R. Grace & Co.-Conn. | Protein non-adsorptive polyurea-urethane polymer coated devices |
US4743632A (en) * | 1987-02-25 | 1988-05-10 | Pfizer Hospital Products Group, Inc. | Polyetherurethane urea polymers as space filling tissue adhesives |
US4829099A (en) | 1987-07-17 | 1989-05-09 | Bioresearch, Inc. | Metabolically acceptable polyisocyanate adhesives |
AU608857B2 (en) | 1987-07-31 | 1991-04-18 | Mitsubishi Rayon Company Limited | Dental adhesive composition |
US4804691A (en) * | 1987-08-28 | 1989-02-14 | Richards Medical Company | Method for making a biodegradable adhesive for soft living tissue |
US4978336A (en) | 1987-09-29 | 1990-12-18 | Hemaedics, Inc. | Biological syringe system |
JP2691722B2 (ja) * | 1988-03-07 | 1997-12-17 | 旭硝子株式会社 | 外科用接着剤 |
US5065752A (en) * | 1988-03-29 | 1991-11-19 | Ferris Mfg. Co. | Hydrophilic foam compositions |
US4883837A (en) * | 1988-06-24 | 1989-11-28 | The Dow Chemical Company | Compatible blends of polyolefins with thermoplastic polyurethanes |
US4874368A (en) | 1988-07-25 | 1989-10-17 | Micromedics, Inc. | Fibrin glue delivery system |
US5843156A (en) * | 1988-08-24 | 1998-12-01 | Endoluminal Therapeutics, Inc. | Local polymeric gel cellular therapy |
EP0390481B1 (en) * | 1989-03-23 | 1996-02-28 | Sanyo Chemical Industries Ltd. | Surgical adhesive sheet |
US4994208A (en) * | 1989-04-18 | 1991-02-19 | Ppg Industries, Inc. | Photochromic polymeric article |
US5487897A (en) * | 1989-07-24 | 1996-01-30 | Atrix Laboratories, Inc. | Biodegradable implant precursor |
US4979942A (en) | 1989-10-16 | 1990-12-25 | Johnson & Johnson Medical, Inc. | Two component syringe delivery system |
US5574104A (en) * | 1990-01-05 | 1996-11-12 | The B. F. Goodrich Company | Chain extended low molecular weight polyoxiranes and electrostatic dissipating blend compositions based thereon |
US5204110A (en) * | 1990-05-02 | 1993-04-20 | Ndm Acquisition Corp. | High absorbency hydrogel wound dressing |
US5166300A (en) * | 1990-07-20 | 1992-11-24 | Lord Corporation | Non-yellowing polyurethane adhesives |
US5389718A (en) * | 1990-07-30 | 1995-02-14 | Miles Inc. | Two-component aqueous polyurethane dispersions |
JPH04150866A (ja) | 1990-10-15 | 1992-05-25 | Nisshinbo Ind Inc | 外科用接着剤 |
JP2928892B2 (ja) | 1990-11-27 | 1999-08-03 | 三洋化成工業株式会社 | 外科用接着剤 |
US5175228A (en) | 1991-12-09 | 1992-12-29 | Gencorp Inc. | Two-component primerless urethane-isocyanurate adhesive compositions having high temperature resistance |
US5368563A (en) | 1991-12-18 | 1994-11-29 | Micromedics, Inc. | Sprayer assembly for physiologic glue |
CA2083741A1 (en) * | 1992-01-24 | 1993-07-25 | James Anthony Braatz | Protein nonadsorptive membranes for wound dressings |
US5573934A (en) * | 1992-04-20 | 1996-11-12 | Board Of Regents, The University Of Texas System | Gels for encapsulation of biological materials |
JPH09506641A (ja) * | 1992-06-26 | 1997-06-30 | ミネソタ マイニング アンド マニュファクチャリング カンパニー | ポリウレタン/ポリ尿素エラストマー |
DE4315173A1 (de) | 1992-12-23 | 1994-06-30 | Bayer Ag | Reine, insbesondere katalysatorfreie Polyurethane |
US5346981A (en) * | 1993-01-13 | 1994-09-13 | Miles Inc. | Radiopaque polyurethanes |
GB9306887D0 (en) * | 1993-04-01 | 1993-05-26 | Graham Neil B | Random block copolymers |
US5703158A (en) | 1993-09-24 | 1997-12-30 | H.B. Fuller Licensing & Financing, Inc. | Aqueous anionic poly (urethane/urea) dispersions |
DE4407490A1 (de) * | 1994-03-07 | 1995-09-14 | Bayer Ag | Verfahren zur Herstellung heißhärtender Einkomponenten-Polyurethan-Reaktivmassen |
EP0754064B1 (en) * | 1994-04-08 | 2003-05-28 | Atrix Laboratories, Inc. | An adjunctive polymer system for use with medical device |
US6339130B1 (en) * | 1994-07-22 | 2002-01-15 | United States Surgical Corporation | Bioabsorbable branched polymers containing units derived from dioxanone and medical/surgical devices manufactured therefrom |
US5578662A (en) * | 1994-07-22 | 1996-11-26 | United States Surgical Corporation | Bioabsorbable branched polymers containing units derived from dioxanone and medical/surgical devices manufactured therefrom |
US5795633A (en) * | 1994-08-22 | 1998-08-18 | Nippon Zeon Co., Ltd. | Material composition and shaped article |
CN1070875C (zh) * | 1995-01-13 | 2001-09-12 | 爱赛克斯特种产品公司 | 可用湿气固化的两组分聚氨酯粘合剂 |
US5618850A (en) * | 1995-03-09 | 1997-04-08 | Focal, Inc. | Hydroxy-acid cosmetics |
US5900245A (en) * | 1996-03-22 | 1999-05-04 | Focal, Inc. | Compliant tissue sealants |
US5780573A (en) * | 1995-06-13 | 1998-07-14 | Kuraray Co., Ltd. | Thermoplastic polyurethanes and molded articles comprising them |
US5702717A (en) | 1995-10-25 | 1997-12-30 | Macromed, Inc. | Thermosensitive biodegradable polymers based on poly(ether-ester)block copolymers |
US6103850A (en) * | 1995-12-29 | 2000-08-15 | Basf Corporation | Sealants made using low unsaturation polyoxyalkylene polyether polyols |
US5922809A (en) * | 1996-01-11 | 1999-07-13 | The Dow Chemical Company | One-part moisture curable polyurethane adhesive |
US5948427A (en) * | 1996-04-25 | 1999-09-07 | Point Medical Corporation | Microparticulate surgical adhesive |
US5791352A (en) * | 1996-06-19 | 1998-08-11 | Fusion Medical Technologies, Inc. | Methods and compositions for inhibiting tissue adhesion |
DE19624641A1 (de) * | 1996-06-20 | 1998-01-08 | Biotec Biolog Naturverpack | Biologisch abbaubarer Werkstoff, bestehend im wesentlichen aus oder auf Basis thermoplastischer Stärke |
US5990237A (en) | 1997-05-21 | 1999-11-23 | Shearwater Polymers, Inc. | Poly(ethylene glycol) aldehyde hydrates and related polymers and applications in modifying amines |
US5900473A (en) * | 1997-06-16 | 1999-05-04 | H.B. Fuller Licensing & Financing, Inc. | Radiation curable pressure sensitive adhesives |
US6211249B1 (en) * | 1997-07-11 | 2001-04-03 | Life Medical Sciences, Inc. | Polyester polyether block copolymers |
US6162241A (en) | 1997-08-06 | 2000-12-19 | Focal, Inc. | Hemostatic tissue sealants |
US6043313A (en) * | 1997-09-04 | 2000-03-28 | Eastman Chemical Company | Thermoplastic polyurethane additives for improved polymer matrix composites and methods of making and using therefor |
US5869566A (en) * | 1997-09-24 | 1999-02-09 | Ppg Industries, Inc. | Rapid drying, isocyanate cured coating composition with improved adhesion |
US6154089A (en) | 1997-12-05 | 2000-11-28 | Texas Instruments Incorporated | Fast bus driver with reduced standby power consumption |
DE69841729D1 (de) | 1997-12-19 | 2010-07-29 | United States Surgical Corp | Aus zwei Elementen bestehende Abgabevorrichtung |
WO1999051656A1 (en) * | 1998-03-31 | 1999-10-14 | Sekisui Chemical Co., Ltd. | Polyesterurethane elastomers and process for their production |
JP4132244B2 (ja) * | 1998-07-06 | 2008-08-13 | 株式会社クラレ | 熱可塑性ポリウレタンからなるポリウレタン弾性繊維およびその製造方法 |
US6297349B1 (en) * | 1998-08-25 | 2001-10-02 | Union Carbide Chemicals & Plastics Technology Corporation | Condensation copolymers having supressed crystallinity |
AU2707500A (en) * | 1998-12-04 | 2000-06-26 | Incept Llc | Biocompatible crosslinked polymers |
EP1146917A1 (en) | 1999-01-22 | 2001-10-24 | St. Jude Medical, Inc. | Medical adhesives |
CA2360627C (en) * | 1999-02-05 | 2009-06-09 | Ziyan Wu | Polyurethane sealant compositions |
US6312725B1 (en) | 1999-04-16 | 2001-11-06 | Cohesion Technologies, Inc. | Rapid gelling biocompatible polymer composition |
DE19924092A1 (de) * | 1999-05-26 | 2000-11-30 | Bayer Ag | Adhäsionsstabiles Verbundmaterial aus Polyurethan und einem weiteren thermoplastischen Material, ein Verfahren zu dessen Herstellung sowie dessen Verwendung in Kraftfahrzeugen |
US6465004B1 (en) * | 1999-06-05 | 2002-10-15 | Noven Pharmaceuticals, Inc. | Solubility enhancement of drugs in transdermal drug delivery systems and methods of use |
DK1218437T3 (da) | 1999-08-27 | 2009-10-19 | Angiodevice Internat Gmbh | Præparater, som danner interpenetrerende polymernetværk, til anvendelse som medicinske tætningsmidler med höj styrke |
WO2001019887A1 (fr) * | 1999-09-10 | 2001-03-22 | Mitsui Chemicals, Inc. | Resine de polyuretane biodegradable |
US6565969B1 (en) * | 1999-10-21 | 2003-05-20 | 3M Innovative Properties Company | Adhesive article |
US20030035786A1 (en) * | 1999-11-04 | 2003-02-20 | Medtronic, Inc. | Biological tissue adhesives, articles, and methods |
US6461631B1 (en) * | 1999-11-16 | 2002-10-08 | Atrix Laboratories, Inc. | Biodegradable polymer composition |
US6395112B1 (en) * | 2000-02-04 | 2002-05-28 | The United States Of America As Represented By The Secretary Of The Navy | Hydrolyzable polymers for explosive and propellant binders |
US6582713B2 (en) * | 2000-04-06 | 2003-06-24 | Univ. Of Colorado - Colorado Springs | Compositions and methods for promoting wound healing |
US6576702B2 (en) * | 2000-07-20 | 2003-06-10 | Noveon Ip Holdings Corp. | Plasticized waterborne polyurethane dispersions and manufacturing process |
US6605666B1 (en) * | 2000-07-27 | 2003-08-12 | 3M Innovative Properties Company | Polyurethane film-forming dispersions in alcohol-water system |
JP2002060341A (ja) | 2000-08-21 | 2002-02-26 | Terumo Corp | 止血剤 |
GB0100760D0 (en) * | 2001-01-11 | 2001-02-21 | Biocompatibles Ltd | Drug delivery from stents |
US20030044380A1 (en) * | 2001-07-19 | 2003-03-06 | Zhu Yong Hua | Adhesive including medicament |
AU2002316314B8 (en) | 2001-07-31 | 2008-04-03 | Covidien Lp | Bioabsorbable adhesive compounds and compositions |
US20040068078A1 (en) * | 2001-12-12 | 2004-04-08 | Milbocker Michael T. | In situ polymerizing medical compositions |
US20050131192A1 (en) * | 2001-12-18 | 2005-06-16 | Takehisa Matsuda | Polymer and process for producing polymer |
DE10163857A1 (de) | 2001-12-22 | 2003-07-10 | Henkel Kgaa | Reaktive Polyurethane mit einem geringen Gehalt an monomeren Diisocyanaten |
US6824703B2 (en) * | 2002-03-08 | 2004-11-30 | Bayer Materialscience Llc | Polyurethane elastomers having improved physical properties and a process for the production thereof |
US6897281B2 (en) * | 2002-04-05 | 2005-05-24 | Noveon Ip Holdings Corp. | Breathable polyurethanes, blends, and articles |
US6972315B2 (en) * | 2002-07-19 | 2005-12-06 | Gross Richard A | Enzyme-catalyzed polycondensations |
DE10309368A1 (de) | 2002-08-06 | 2004-02-26 | Aventis Behring Gmbh Intellectual Property/Legal | Pharmazeutische Zubereitung mit RNA als Cofaktor der Hämostase |
CN1166715C (zh) * | 2002-08-23 | 2004-09-15 | 清华大学 | 一种可生物降解聚氨酯弹性体的合成 |
CA2499447C (en) | 2002-10-28 | 2011-03-29 | Tyco Healthcare Group Lp | Fast curing compositions |
US20060111537A1 (en) | 2002-10-28 | 2006-05-25 | Tyco Healthcare Group Lp | Bioabsorbable adhesive compounds |
US7232859B2 (en) | 2002-10-31 | 2007-06-19 | Dow Global Technologies Inc. | Polyurethane dispersion and articles prepared therefrom |
US20040198944A1 (en) * | 2003-03-04 | 2004-10-07 | Meltzer Donald A. | Thermoplastic polyurethanes |
IL155866A0 (en) * | 2003-05-12 | 2003-12-23 | Yissum Res Dev Co | Responsive polymeric system |
US20040242831A1 (en) | 2003-05-30 | 2004-12-02 | Dong Tian | Enzyme catalyzed polyesters and polyol polymers |
WO2005034781A1 (en) * | 2003-09-29 | 2005-04-21 | Promethean Surgical Devices Llc | Devices and methods for spine repair |
US7514503B2 (en) * | 2003-10-08 | 2009-04-07 | Asahi Kasei Chemicals Corporation | Molded article produced from aliphatic polyester resin composition |
CA2536192A1 (en) | 2003-11-20 | 2005-06-09 | Angiotech International Ag | Soft tissue implants and anti-scarring agents |
US20050129733A1 (en) * | 2003-12-09 | 2005-06-16 | Milbocker Michael T. | Surgical adhesive and uses therefore |
US8309112B2 (en) * | 2003-12-24 | 2012-11-13 | Advanced Cardiovascular Systems, Inc. | Coatings for implantable medical devices comprising hydrophilic substances and methods for fabricating the same |
US20050266086A1 (en) | 2004-06-01 | 2005-12-01 | Sawhney Amarpreet S | Intrauterine applications of materials formed in situ |
US8460378B2 (en) * | 2004-07-26 | 2013-06-11 | DePuy Sythes Products, LLC | Biocompatible, biodegradable polyurethane materials with controlled hydrophobic to hydrophilic ratio |
US8044234B2 (en) | 2005-05-05 | 2011-10-25 | Tyco Healthcare Group Lp | Bioabsorbable surgical composition |
EP1968617A4 (en) * | 2005-12-06 | 2012-05-02 | Tyco Healthcare | BIOCOMPATIBLE TISSUE SEALING ADHESIVES AND AGENTS |
CA2628598C (en) * | 2005-12-06 | 2015-02-24 | Tyco Healthcare Group Lp | Bioabsorbable surgical composition |
AU2006321721B2 (en) * | 2005-12-08 | 2012-07-05 | Covidien Lp | Biocompatible surgical compositons |
US20070135606A1 (en) * | 2005-12-08 | 2007-06-14 | Tyco Healthcare Group Lp | Biocompatible surgical compositions |
GB0620685D0 (en) * | 2006-10-18 | 2006-11-29 | Controlled Therapeutics Sct | Bioresorbable polymers |
-
2006
- 2006-12-06 CA CA2628598A patent/CA2628598C/en not_active Expired - Fee Related
- 2006-12-06 EP EP06844894A patent/EP1968483A4/en not_active Withdrawn
- 2006-12-06 US US11/635,365 patent/US7858078B2/en not_active Expired - Fee Related
- 2006-12-06 EP EP13170126.0A patent/EP2633834A1/en not_active Withdrawn
- 2006-12-06 WO PCT/US2006/046558 patent/WO2007067625A2/en active Application Filing
- 2006-12-06 AU AU2006321915A patent/AU2006321915B2/en not_active Ceased
- 2006-12-06 JP JP2008544476A patent/JP2009518129A/ja active Pending
-
2010
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Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS63278924A (ja) * | 1987-05-09 | 1988-11-16 | Bio Material Yunibaasu:Kk | 生体内分解吸収性ウレタンプレポリマ− |
JP2000514457A (ja) * | 1996-07-11 | 2000-10-31 | ライフ・メディカル・サイエンシーズ,インコーポレイテッド | 術後の癒着形成を減少または排除するための方法および組成物 |
JP2006519633A (ja) * | 2003-01-09 | 2006-08-31 | ポリガニックス ビー. ブイ. | 生体医用フォーム |
WO2005100429A1 (en) * | 2004-04-15 | 2005-10-27 | The University Of Utah Research Foundation | Bioresponsive polymer system for delivery of microbicides |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2009518127A (ja) * | 2005-12-06 | 2009-05-07 | タイコ ヘルスケア グループ リミテッド パートナーシップ | 生体適合性外科用組成物 |
JP2010525152A (ja) * | 2007-04-24 | 2010-07-22 | タイコ ヘルスケア グループ リミテッド パートナーシップ | 生分解性マクロマー |
US9382386B2 (en) | 2012-12-06 | 2016-07-05 | Lg Chem, Ltd | Lactide copolymer, method for preparing same, and resin composition comprising same |
US9382385B2 (en) | 2012-12-06 | 2016-07-05 | Lg Chem, Ltd. | Lactide copolymer, and resin composition and film comprising same |
Also Published As
Publication number | Publication date |
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US8357361B2 (en) | 2013-01-22 |
US20110059061A1 (en) | 2011-03-10 |
US7858078B2 (en) | 2010-12-28 |
EP2633834A1 (en) | 2013-09-04 |
AU2006321915B2 (en) | 2012-04-26 |
US20070128154A1 (en) | 2007-06-07 |
WO2007067625A2 (en) | 2007-06-14 |
CA2628598A1 (en) | 2007-06-14 |
EP1968483A4 (en) | 2010-07-21 |
JP2013056242A (ja) | 2013-03-28 |
AU2006321915A1 (en) | 2007-06-14 |
WO2007067625A3 (en) | 2008-01-10 |
EP1968483A2 (en) | 2008-09-17 |
CA2628598C (en) | 2015-02-24 |
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