JP4530990B2 - 形状記憶特性を有するアモルファス及び半結晶質ポリマーのブレンド - Google Patents
形状記憶特性を有するアモルファス及び半結晶質ポリマーのブレンド Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3893—Low-molecular-weight compounds having heteroatoms other than oxygen containing silicon
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
- C08G61/04—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms
- C08G61/06—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds
- C08G61/08—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds of carbocyclic compounds containing one or more carbon-to-carbon double bonds in the ring
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/005—Processes for mixing polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L27/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers
- C08L27/02—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L27/12—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
- C08L27/16—Homopolymers or copolymers or vinylidene fluoride
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L31/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid; Compositions of derivatives of such polymers
- C08L31/02—Homopolymers or copolymers of esters of monocarboxylic acids
- C08L31/04—Homopolymers or copolymers of vinyl acetate
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/04—Polyesters derived from hydroxycarboxylic acids, e.g. lactones
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2230/00—Compositions for preparing biodegradable polymers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
- C08L33/10—Homopolymers or copolymers of methacrylic acid esters
- C08L33/12—Homopolymers or copolymers of methyl methacrylate
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Materials For Medical Uses (AREA)
- Dental Preparations (AREA)
- Processing And Handling Of Plastics And Other Materials For Molding In General (AREA)
- Investigating Or Analysing Biological Materials (AREA)
Description
a)医療(ヒューマンヘルスケア)用ステント、パッチ及びその他のインプラント
b)調節可能な形状と高剛性(硬直性)を要求される外科用ツール
c)パーソナルケア用品(食器類、ブラシなど)及びハードウェアツールハンドルなど、自由に形状を調節できる構造的道具
d)自己回復プラスチック
e)医療機器
f)成形、複製、ラピッドプロトタイピング(光造形、高速造形技術)、歯科及びフィギュア印刷用の印象材
g)玩具
h)情報蓄積用可逆的エンボス加工
i)温度センサ
j)安全バルブ
k)熱収縮テープ又はシール
l)熱制御継手及びファスナー
m)ラージストレイン、ラージフォースアクチュエータ
Mw=500,000g/molのポリ(酢酸ビニル)はアルドリッチ(Aldrich)社から購入し、室温で2日間真空処理して水分を含む揮発性物質を除去した。Mw=130,000g/molのポリ(ラクチド)はコネチカット大学のS.Huang教授に提供してもらい、使用前にT=60℃で一晩乾燥させた。該材料は92%のL−異性体と8%のD−異性体を含むことがわかった。Mw=180,000g/molのポリ(フッ化ビニリデン)もアルドリッチ社から購入し、室温で2日間真空処理して水分を含む揮発性物質を除去した。
様々なブレンド比を使用してPLA/PVAc及びPVDF/PVAcの溶融ブレンディングを30mlのブラベンダ(Brabender)社の二軸スクリューミキサ中で実施した。該ミキサをT=180℃で5分間平衡化した後、ミキサの羽根の回転を25RPMに調整し、予備混合したポリマーペレットをチェンバに1分間かけて加えた。該ポリマーを10分間混合し、良好な分散を確保した。チェンバに窒素をパージして、混合時の酸化分解の可能性を軽減した。混合後、ブレンドをチェンバから取り出し、室温に冷却してから180℃のカルバ(Carver)プレスの熱盤間で8メートルトンの荷重下で5分間プレスした。スペーサを用いてフィルム厚を調節し、室温への急速冷却を行った。このようにして形成されたフィルムを用いて熱的及び機械的特性分析を実施した。
示差走査熱量測定法(DSC)による測定及び溶融ブレンディングの前にポリマーの熱的性質(熱重量分析(TGA))を測定し、ポリマー中に溶媒蒸気が存在しないことを確かめた。この目的のためにTAインスツルメンツ社(TA 2950)のTGAを用い、ポリマーのサンプルを窒素雰囲気下20℃/分の加熱速度で25℃から600℃に加熱した。DSC分析にはパーキン−エルマー(Perkin-Elmer)社のDSC−7を使用した。ペレット及び熱圧フィルムから調製した10gのサンプルをまず加熱速度10℃/分で20℃から200℃に加熱し(第一の加熱)、次いで同じ速度で20℃に冷却し、最後に該サンプルを加熱速度10℃/分で200℃に再加熱した(第二の加熱)。各ブレンドのTgを、第二の加熱時に観察される熱容量変化の中点から決定した。
TGAの結果から、PLAもPVAcもT<300℃で安定なことが示された。この温度を超えると、PLAは完全に分解するが(チャー収率なし)、PVAcは375<T<425℃では25wt%の中間チャー収率が得られるような分解をし、450℃を超えると完全分解する。ブレンドの加工と熱及び動的機械分析(DSC及びDMA)は分解を完全に回避するために250℃未満で実施した。
Claims (14)
- ポリ(フッ化ビニリデン)、ポリグリコリド類、ポリラクチド及びそのコポリマー類、ポリ(ヒドロキシブチレート)、ポリ(エチレングリコール)、ポリエチレン、ポリエチレン−コ−酢酸ビニル、ポリ(塩化ビニル)、ポリ(塩化ビニリデン)及びポリ塩化ビニリデンとポリ塩化ビニルのコポリマー類からなる群から選ばれる結晶質ポリマーと、
ポリ(酢酸ビニル)、ポリメチルアクリレート、ポリエチルアクリレート、アタクチックポリメチルメタクリレート、アイソタクチックポリメチルメタクリレート及びシンジオタクチックポリメチルメタクリレートからなる群から選ばれるアモルファスポリマーと、のブレンドを含み、
室温を超える融解温度Tmと、室温を超えるガラス転移温度Tgと、を有し、
前記ブレンドを、Tgよりも高くTmよりも低い温度でアニールすることにより形成される物理的架橋に由来するゴム弾性率及び弾性を有することを特徴とする形状記憶ポリマー材料。 - 前記ブレンドが、アモルファスポリ(酢酸ビニル)と半結晶質ポリラクチドのものであることを特徴とする請求項1に記載の形状記憶ポリマー材料。
- 前記ブレンドが、アモルファスポリ酢酸ビニルと結晶質ポリ(フッ化ビニリデン)のものであることを特徴とする請求項1に記載の形状記憶ポリマー材料。
- 前記ブレンドが、結晶質ポリ(フッ化ビニリデン)とアモルファスポリメチルメタクリレートのものであることを特徴とする請求項1に記載の形状記憶ポリマー材料。
- 前記ブレンドが、結晶質ポリ(塩化ビニリデン)とアモルファスポリ酢酸ビニルのものであることを特徴とする請求項1に記載の形状記憶ポリマー材料。
- ポリ(フッ化ビニリデン)、ポリラクチド、ポリ(ヒドロキシブチレート)、ポリ(エチレングリコール)、ポリエチレン、ポリエチレン−コ−酢酸ビニル、ポリ(塩化ビニル)、ポリ(塩化ビニリデン)及びポリ塩化ビニリデンとポリ塩化ビニルのコポリマー類からなる群から選ばれる結晶質ポリマーと、
ポリ(酢酸ビニル)、ポリメチルアクリレート、ポリエチルアクリレート、アタクチックポリメチルメタクリレート、アイソタクチックポリメチルメタクリレート及びシンジオタクチックポリメチルメタクリレートからなる群から選ばれるアモルファスポリマーと、
を前記結晶質ポリマーの融点より10〜20℃高い温度で、良好な混合を確保するに足る時間で溶融ブレンディングし、得られたブレンドを室温に冷却し、前記ブレンドを180℃に維持されたプレスに導入し、前記ブレンドに圧力を印加し、次にそれによって形成されたフィルムをアニール温度Tg<Ta<Tmに急速に冷却し、結晶化が完了するまでその温度に保持し、その後前記フィルムを室温に冷却することを含む、室温を超えるTgと、ゴム弾性率及び弾性が物理的架橋に由来することを特徴とする形状記憶ポリマー材料の製造法。 - 前記溶融ブレンディングが、5〜10分間実施されることを特徴とする請求項6に記載の方法。
- 前記ブレンドが、アモルファスポリ(酢酸ビニル)と結晶質ポリラクチドの溶融ブレンディングによって形成されることを特徴とする請求項6に記載の方法。
- 前記ブレンドが、アモルファスポリ(酢酸ビニル)と半結晶質ポリ(フッ化ビニリデン)の溶融ブレンディングによって形成されることを特徴とする請求項6に記載の方法。
- 請求項1に記載の形状記憶ポリマーから製造される、調節可能な形状でありながら高剛性も要求される外科用ツール。
- 請求項1に記載の形状記憶ポリマーから製造される印象材であって、成形用、複製用、ラピッドプロトタイピング用又は歯科用の印象材。
- 請求項1に記載の形状記憶ポリマーから製造される温度センサ。
- 請求項1に記載の形状記憶ポリマーから製造される感熱シール。
- 請求項1に記載の形状記憶ポリマーから製造されるアクチュエータ。
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Application Number | Priority Date | Filing Date | Title |
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US41802302P | 2002-10-11 | 2002-10-11 | |
US46640103P | 2003-04-29 | 2003-04-29 | |
US48832303P | 2003-07-18 | 2003-07-18 | |
PCT/US2003/032329 WO2004033539A1 (en) | 2002-10-11 | 2003-10-10 | Blends of amorphous and semicrystalline polymers having shape memory properties |
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Families Citing this family (82)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8088060B2 (en) | 2000-03-15 | 2012-01-03 | Orbusneich Medical, Inc. | Progenitor endothelial cell capturing with a drug eluting implantable medical device |
US9522217B2 (en) | 2000-03-15 | 2016-12-20 | Orbusneich Medical, Inc. | Medical device with coating for capturing genetically-altered cells and methods for using same |
US20040030062A1 (en) * | 2002-05-02 | 2004-02-12 | Mather Patrick T. | Castable shape memory polymers |
US7794494B2 (en) * | 2002-10-11 | 2010-09-14 | Boston Scientific Scimed, Inc. | Implantable medical devices |
US20050010275A1 (en) | 2002-10-11 | 2005-01-13 | Sahatjian Ronald A. | Implantable medical devices |
ES2373650T3 (es) * | 2002-10-11 | 2012-02-07 | University Of Connecticut | Policicloocteno reticulado. |
US7976936B2 (en) | 2002-10-11 | 2011-07-12 | University Of Connecticut | Endoprostheses |
US7524914B2 (en) * | 2002-10-11 | 2009-04-28 | The University Of Connecticut | Shape memory polymers based on semicrystalline thermoplastic polyurethanes bearing nanostructured hard segments |
DE60336074D1 (de) * | 2002-10-11 | 2011-03-31 | Univ Connecticut | Mischungen von amorphen und semikristallinen polymeren mit formgedächtniseigenscchaften |
JP4805148B2 (ja) | 2003-07-18 | 2011-11-02 | ボストン サイエンティフィック リミテッド | 医療器具 |
GB0329654D0 (en) * | 2003-12-23 | 2004-01-28 | Smith & Nephew | Tunable segmented polyacetal |
GB0401202D0 (en) | 2004-01-20 | 2004-02-25 | Ucl Biomedica Plc | Polymer for use in conduits and medical devices |
US7601274B2 (en) * | 2004-03-31 | 2009-10-13 | The University Of Connecticut | Shape memory main-chain smectic-C elastomers |
US8808479B2 (en) * | 2004-06-04 | 2014-08-19 | Cornerstone Research Group, Inc. | Method of making and using shape memory polymer composite patches |
US8043361B2 (en) | 2004-12-10 | 2011-10-25 | Boston Scientific Scimed, Inc. | Implantable medical devices, and methods of delivering the same |
WO2006071520A2 (en) * | 2004-12-10 | 2006-07-06 | University Of Connecticut | Shape memory polymer orthodontic appliances, and methods of making and using the same |
CA2603652A1 (en) | 2005-04-01 | 2006-10-12 | The Regents Of The University Of Colorado | A graft fixation device and method |
DE602006009542D1 (de) * | 2005-11-30 | 2009-11-12 | Toray Industries | Mehrlagiges flächengebilde aus polymilchsäureharz und daraus hergestellter formkörper |
US20090248141A1 (en) * | 2006-03-30 | 2009-10-01 | The Regents Of The University Of Colorado | Shape Memory Polymer Medical Devices |
DE102006017759A1 (de) | 2006-04-12 | 2007-10-18 | Gkss-Forschungszentrum Geesthacht Gmbh | Formgedächtnispolymer mit Polyester- und Polyacrylsegmenten und Verfahren zu seiner Herstellung und Programmierung |
US20090131557A1 (en) * | 2006-05-02 | 2009-05-21 | Hiroshi Uyama | Shape memory resin |
EP2044140B1 (en) | 2006-07-20 | 2017-05-17 | OrbusNeich Medical, Inc. | Bioabsorbable polymeric composition for a medical device |
US8460362B2 (en) * | 2006-07-20 | 2013-06-11 | Orbusneich Medical, Inc. | Bioabsorbable polymeric medical device |
US20080085946A1 (en) * | 2006-08-14 | 2008-04-10 | Mather Patrick T | Photo-tailored shape memory article, method, and composition |
US7959942B2 (en) * | 2006-10-20 | 2011-06-14 | Orbusneich Medical, Inc. | Bioabsorbable medical device with coating |
US8691321B2 (en) * | 2006-10-20 | 2014-04-08 | Orbusneich Medical, Inc. | Bioabsorbable polymeric composition and medical device background |
DE602007011671D1 (de) * | 2006-11-30 | 2011-02-10 | Smith & Nephew Inc | Faserverstärktes verbundmaterial |
US20080132988A1 (en) * | 2006-12-01 | 2008-06-05 | Scimed Life Systems, Inc. | Balloon geometry for delivery and deployment of shape memory polymer stent with flares |
WO2008077123A1 (en) * | 2006-12-19 | 2008-06-26 | The Regents Of The University Of Colorado | Shape memory polymer-based transcervical device for permanent or temporary sterilization |
CN100463795C (zh) * | 2007-01-22 | 2009-02-25 | 哈尔滨工业大学 | 聚乳酸系聚合物获得冷变形成型形状记忆效应的处理方法 |
DE102007010564A1 (de) | 2007-02-22 | 2008-08-28 | Gkss-Forschungszentrum Geesthacht Gmbh | Verfahren zur Einschritt-Programmierung von Dreiformenkunststoffen |
JP5416090B2 (ja) * | 2007-04-18 | 2014-02-12 | スミス アンド ネフュー ピーエルシー | 形状記憶ポリマーの膨張成形 |
AU2008242737B2 (en) | 2007-04-19 | 2013-09-26 | Smith & Nephew, Inc. | Multi-modal shape memory polymers |
ATE505220T1 (de) | 2007-04-19 | 2011-04-15 | Smith & Nephew Inc | Graft-fixierung |
US20110130822A1 (en) * | 2007-07-20 | 2011-06-02 | Orbusneich Medical, Inc. | Bioabsorbable Polymeric Compositions and Medical Devices |
US20100093946A1 (en) * | 2008-10-11 | 2010-04-15 | Orbusneich Medical, Inc. | Bioabsorbable Polymeric Compositions and Medical Devices |
JP4801027B2 (ja) * | 2007-09-12 | 2011-10-26 | メイラ株式会社 | 形状記憶性樹脂製雄型締結体およびその製造方法 |
KR101023446B1 (ko) * | 2007-09-21 | 2011-03-25 | 주식회사 바이오에이비씨랩 | 연신에 의해 전기적 신호를 발생시키는 물질을 포함하는 센서 |
WO2009132070A2 (en) * | 2008-04-22 | 2009-10-29 | The Regents Of The University Of Colorado, A Body Corporate | Thiol-vinyl and thiol-yne systems for shape memory polymers |
TW201002781A (en) * | 2008-07-08 | 2010-01-16 | Ind Tech Res Inst | Materials having shape memory properties and method for fabricating the same |
CN101643573B (zh) * | 2008-08-07 | 2011-12-07 | 财团法人工业技术研究院 | 具有形状记忆特性材料及其制备方法 |
US20110178247A1 (en) * | 2008-09-17 | 2011-07-21 | Cornerstone Research Group, Inc | Extrudable shape memory polymer |
US8136536B2 (en) | 2008-09-24 | 2012-03-20 | Elc Management Llc | Shape memory polymer mascara brush |
WO2010042854A1 (en) * | 2008-10-10 | 2010-04-15 | Orbusneich Medical, Inc. | Bioabsorbable polymeric medical device |
WO2010048052A1 (en) | 2008-10-22 | 2010-04-29 | Boston Scientific Scimed, Inc. | Shape memory tubular stent with grooves |
US9119714B2 (en) * | 2008-10-29 | 2015-09-01 | The Regents Of The University Of Colorado, A Body Corporate | Shape memory polymer prosthetic medical device |
US9533469B2 (en) | 2008-12-23 | 2017-01-03 | Syracuse University | Self-healing product |
EP2413840B1 (en) | 2009-04-02 | 2016-08-17 | Endoshape, Inc. | Vascular occlusion devices |
WO2010132899A1 (en) * | 2009-05-15 | 2010-11-18 | Orbusneich Medical, Inc. | Bioabsorbable polymeric compositions and medical devices |
CA2770885A1 (en) * | 2009-08-27 | 2011-03-17 | Metabolix, Inc. | Toughened polyhydroxyalkanoate compositions |
US8683798B2 (en) * | 2010-01-15 | 2014-04-01 | Syracuse University | Stimuli-responsive product |
US8486502B2 (en) * | 2010-05-12 | 2013-07-16 | Nexans | PVDF/PVC alloys for plenum cable applications |
US8550979B2 (en) | 2010-06-15 | 2013-10-08 | Coloplast A/S | Method of treating incontinence |
EP2600902A4 (en) | 2010-08-06 | 2015-01-07 | Endoshape Inc | X-RAY DENSITY RESIN POLYMERS FOR MEDICAL DEVICES |
US9427493B2 (en) | 2011-03-07 | 2016-08-30 | The Regents Of The University Of Colorado | Shape memory polymer intraocular lenses |
WO2014160320A2 (en) | 2013-03-13 | 2014-10-02 | Endoshape Inc. | Continuous embolic coil and methods and devices for delivery of the same |
AU2013209672B2 (en) | 2012-01-17 | 2015-11-19 | Endoshape, Inc. | Occlusion device for a vascular or biological lumen |
CN109054254B (zh) | 2012-08-17 | 2021-02-02 | Cj第一制糖株式会社 | 用于聚合物共混物的生物基橡胶改性剂 |
US8815054B2 (en) | 2012-10-05 | 2014-08-26 | The Procter & Gamble Company | Methods for making fibrous paper structures utilizing waterborne shape memory polymers |
US9527947B2 (en) | 2012-10-11 | 2016-12-27 | The Hong Kong Polytechnic University | Semi-crystalline shape memory polymer and production method thereof |
CN108853610A (zh) | 2013-02-08 | 2018-11-23 | 恩多沙普公司 | 用于医疗装置的不透射线的聚合物 |
JP6543831B2 (ja) | 2013-03-15 | 2019-07-17 | エンドゥーシェイプ インコーポレイテッド | 高められた放射線不透過性を有するポリマー組成物 |
CN105531308B (zh) | 2013-05-30 | 2021-08-10 | Cj 第一制糖株式会社 | 回收物共混物 |
EP2927210B1 (en) | 2014-02-07 | 2020-09-23 | LG Chem, Ltd. | Plasticizers, resin composition, and method for manufacturing plasticizers and resin composition |
US20170198104A1 (en) * | 2014-03-12 | 2017-07-13 | Arevo, Inc. | Compositions for use in fused filament 3d fabrication and method for manufacturing same |
EP3122817B1 (en) | 2014-03-27 | 2020-07-29 | CJ CheilJedang Corporation | Highly filled polymer systems |
WO2016105998A1 (en) | 2014-12-22 | 2016-06-30 | 3M Innovative Properties Company | Compositions and films comprising polylactic acid polymer, polyvinyl acetate polymer and plasticizer |
US9908978B2 (en) | 2015-04-08 | 2018-03-06 | Arevo Inc. | Method to manufacture polymer composite materials with nano-fillers for use in additive manufacturing to improve material properties |
JP6665442B2 (ja) * | 2015-08-17 | 2020-03-13 | 日立化成株式会社 | 接合部材形成用組成物、接合部材、接合体、及び接合部材を製造する方法 |
US11117311B2 (en) * | 2015-10-05 | 2021-09-14 | Arevo, Inc. | Amorphous polyaryletherketone and blends thereof for use in additive manufacturing |
CN108699272B (zh) * | 2016-02-15 | 2021-10-26 | 3M创新有限公司 | 包括结构化表面的聚乳酸聚合物基膜和制品 |
WO2017200756A1 (en) * | 2016-05-20 | 2017-11-23 | 3M Innovative Properties Company | Oriented polylactic acid polymer based film |
JP7170544B2 (ja) * | 2016-06-21 | 2022-11-14 | スリーエム イノベイティブ プロパティズ カンパニー | 半結晶性ポリ乳酸系フィルムを含むグラフィック物品 |
WO2018080465A1 (en) * | 2016-10-26 | 2018-05-03 | Massachusetts Institute Of Technology | Multidirectional artificial muscles from nylon |
US10623846B2 (en) * | 2016-12-06 | 2020-04-14 | Bose Corporation | Earpieces employing viscoelastic materials |
US11643550B2 (en) | 2018-04-05 | 2023-05-09 | Adolphe Merkle Institute, University Of Fribourg | Shape memory polymers |
US20200232857A1 (en) * | 2019-01-21 | 2020-07-23 | Technische Universiteit Eindhoven | Optical sensor based on shape memory between scattering and transparent modes |
CN111529755A (zh) * | 2020-05-21 | 2020-08-14 | 上海交通大学医学院附属第九人民医院 | 一种poss增强水凝胶及其制备方法和用途 |
JP7400125B6 (ja) | 2020-06-26 | 2024-01-19 | ジャビル インク | ポリエステル/ポリ(メチルメタクリレート)物品およびその製造方法 |
WO2022260613A1 (en) * | 2021-06-10 | 2022-12-15 | İzmi̇r Eği̇ti̇m Sağlik Sanayi̇ Yatirim A.Ş. | Production method of polylactite with efficient processability |
CN113402866B (zh) * | 2021-07-08 | 2022-09-27 | 长春工业大学 | 一种基于形状记忆调控药物释放的聚合物 |
CN114085477B (zh) * | 2021-10-29 | 2022-12-09 | 航天材料及工艺研究所 | 一种耐油导电氟橡胶、制备方法及应用 |
Family Cites Families (127)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1035282A (en) * | 1964-01-17 | 1966-07-06 | Montedison Spa | High molecular weight unsaturated hydrocarbon homopolymers |
US3563973A (en) * | 1965-03-04 | 1971-02-16 | Radiation Applic Inc | Articles with polymeric memory and method of constructing same |
US3383336A (en) * | 1966-06-27 | 1968-05-14 | Kuyama Hiroshi | Resinous insoluble reaction products |
NL162664B (nl) * | 1969-06-20 | 1980-01-15 | Montedison Spa | Werkwijze om een katalysator te bereiden voor de poly- merisatie van alkenen-1. |
USRE31883E (en) * | 1969-12-16 | 1985-05-14 | General Electric Company | Resinoid grinding wheels containing nickel-coated cubic boron nitride particles |
US4080357A (en) * | 1976-06-07 | 1978-03-21 | Shell Oil Company | Multicomponent halogenated thermoplastic-block copolymer-polymer blends |
US4337349A (en) * | 1980-06-02 | 1982-06-29 | Scientific Pharmaceuticals, Inc. | Dimethacrylate adducts of glycidyl methacrylate with diesters of bis (hydroxymethyl) tricyclo[5.2.1.02,6] decane and dicarboxylic acids |
DE3224691A1 (de) * | 1982-07-02 | 1984-01-05 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur herstellung von hochmolekularen polyphenylenoxiden |
US4579904A (en) * | 1982-09-24 | 1986-04-01 | Blendax Werke R. Schneider Gmbh & Co. | Diacrylic and dimethacrylic esters and their use |
ATE124072T1 (de) | 1985-01-04 | 1995-07-15 | Thoratec Lab Corp | Verfahren zur herstellung eines formteils mit formgedächtniseigenschaften sowie einige dieser erhaltenen formteile. |
US5506300A (en) * | 1985-01-04 | 1996-04-09 | Thoratec Laboratories Corporation | Compositions that soften at predetermined temperatures and the method of making same |
JPS61231051A (ja) * | 1985-04-06 | 1986-10-15 | Sumitomo Electric Ind Ltd | 形状記憶物品 |
US4612241A (en) * | 1985-06-12 | 1986-09-16 | E. I. Du Pont De Nemours And Company | Impact resistant composites with elastomeric fibers |
JPH0745555B2 (ja) * | 1986-03-28 | 1995-05-17 | 三菱油化株式会社 | 光学材料用樹脂およびその製造法 |
US4794096A (en) * | 1987-04-03 | 1988-12-27 | Fina Technology, Inc. | Hafnium metallocene catalyst for the polymerization of olefins |
US4794192A (en) * | 1987-07-06 | 1988-12-27 | General Electric Company | Cyclic aminoalkylsilanes and their use as adhesion promoters in room temperature vulcanizable polydiorganosiloxane compositions |
US4975403A (en) * | 1987-09-11 | 1990-12-04 | Fina Technology, Inc. | Catalyst systems for producing polyolefins having a broad molecular weight distribution |
US5021523A (en) * | 1987-11-05 | 1991-06-04 | Kureha Kagaku Kogyo Kabushiki Kaisha | Polymer alloy of polyarylene thioether and a process for producing the same |
DE3817624A1 (de) * | 1988-05-25 | 1989-11-30 | Bayer Ag | Mischungen, hergestellt aus metastabil amorphen, teilkirstallinen thermoplasten |
US5243002A (en) * | 1988-07-15 | 1993-09-07 | Fina Technology, Inc. | Process and catalyst for producing syndiotactic polymers |
JP2502132B2 (ja) * | 1988-09-30 | 1996-05-29 | 三菱重工業株式会社 | 形状記憶ポリウレタンエラストマ―成形体 |
CA2002408A1 (en) | 1988-11-11 | 1990-05-11 | Shoji Suzuki | Structural material and its application |
US5189110A (en) * | 1988-12-23 | 1993-02-23 | Asahi Kasei Kogyo Kabushiki Kaisha | Shape memory polymer resin, composition and the shape memorizing molded product thereof |
US5037689A (en) * | 1989-02-17 | 1991-08-06 | Basf Aktiengesellschaft | Toughened thermosetting structural materials |
KR930001716B1 (ko) * | 1989-02-28 | 1993-03-12 | 다이낀 고오교오 가부시끼가이샤 | 형상 기억성 고분자재료 |
JP2656343B2 (ja) * | 1989-03-30 | 1997-09-24 | 株式会社クラレ | トランスポリイソプレン樹脂組成物 |
US5282854A (en) * | 1989-10-11 | 1994-02-01 | Daikin Industries Ltd. | Fluorine-containing block copolymer and artificial lens comprising the same |
US5147385A (en) * | 1989-11-01 | 1992-09-15 | Schneider (Europe) A.G. | Stent and catheter for the introduction of the stent |
JPH0649788B2 (ja) * | 1990-01-23 | 1994-06-29 | 工業技術院長 | 熱可塑性樹脂成形体の表面活性化方法 |
JPH0649789B2 (ja) * | 1990-01-23 | 1994-06-29 | 工業技術院長 | 熱可塑性樹脂成形体の表面活性化方法 |
JPH03235067A (ja) | 1990-02-13 | 1991-10-21 | Tosoh Corp | 電磁式導電率計及び導電率測定方法 |
US5120800A (en) * | 1990-04-10 | 1992-06-09 | Mitsubishi Petrochemical Co., Ltd. | Process for preparing modified-polyphenylene ether |
US5053496A (en) * | 1990-04-27 | 1991-10-01 | The Bf Goodrich Company | Low viscosity statistical monofunctional carboxylic-terminated, amine-terminated, or epoxy-terminated reactive liquid rubber polymers, and a process for preparation thereof |
US5198510A (en) * | 1990-04-27 | 1993-03-30 | The B. F. Goodrich Company | Modification of vinyl ester resins with reactive liquid polymers |
US5086204A (en) * | 1990-05-31 | 1992-02-04 | The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration | Method of producing a plug-type heat flux gauge |
JPH0798906B2 (ja) * | 1990-06-01 | 1995-10-25 | 三井東圧化学株式会社 | 樹脂組成物 |
JP2906614B2 (ja) * | 1990-08-29 | 1999-06-21 | 株式会社浜松プラテック | 感温透明―不透明変換組成物及び感温透明―不透明変換組成物を用いた温度センサ |
US5258020A (en) * | 1990-09-14 | 1993-11-02 | Michael Froix | Method of using expandable polymeric stent with memory |
US5163952A (en) * | 1990-09-14 | 1992-11-17 | Michael Froix | Expandable polymeric stent with memory and delivery apparatus and method |
US6248129B1 (en) * | 1990-09-14 | 2001-06-19 | Quanam Medical Corporation | Expandable polymeric stent with memory and delivery apparatus and method |
GB9020462D0 (en) * | 1990-09-19 | 1990-10-31 | Filters For Industry Ltd | Abrasive segments |
US5665822A (en) * | 1991-10-07 | 1997-09-09 | Landec Corporation | Thermoplastic Elastomers |
TW218884B (ja) * | 1991-05-01 | 1994-01-11 | Mitsubishi Kakoki Kk | |
WO1992020330A1 (en) * | 1991-05-17 | 1992-11-26 | Fuisz Technologies Ltd. | New thermoplastic polymeric material and process for making same |
DE69222700T2 (de) * | 1991-07-11 | 1998-03-26 | Idemitsu Kosan Co | Verfahren zur Herstellung von Polymeren auf Olefinbasis und Olefin-Polymerisationskatalysatoren |
HUT62831A (en) * | 1991-09-12 | 1993-06-28 | Gen Electric | Method for producing covered cubed leather-nitride abrasive grain, abrasive grain and grinding tool by using the same |
US5500013A (en) * | 1991-10-04 | 1996-03-19 | Scimed Life Systems, Inc. | Biodegradable drug delivery vascular stent |
US5334444A (en) | 1991-12-24 | 1994-08-02 | Alliedsignal Inc. | Compatibilized polyphenylene ether/polyamide monofilament and felt made thereform |
DE4231995A1 (de) * | 1992-09-24 | 1994-03-31 | Roehm Gmbh | Lichtstreuende Polystyrolformmasse und daraus hergestellte Formkörper |
JP3324166B2 (ja) * | 1992-12-10 | 2002-09-17 | 信越化学工業株式会社 | 接着性シリコーンゴム組成物 |
JPH08504874A (ja) * | 1992-12-21 | 1996-05-28 | レイケム・コーポレイション | ポリマーブレンド |
US5964744A (en) * | 1993-01-04 | 1999-10-12 | Menlo Care, Inc. | Polymeric medical device systems having shape memory |
IT1269291B (it) * | 1994-03-04 | 1997-03-26 | Ausimont Spa | Miscele di poli (vinilidene fluoruro) e loro impiego per la formulazione di vernici ad elevata brillantezza |
NL9400519A (nl) | 1994-03-31 | 1995-11-01 | Rijksuniversiteit | Intravasculaire polymere stent. |
JPH07292040A (ja) * | 1994-04-28 | 1995-11-07 | Yoshihito Osada | 感熱性形状記憶ゲル |
BE1008917A3 (fr) * | 1994-11-16 | 1996-10-01 | Diamant Boart Sa | Outil abrasif, de coupe ou analogue et procede de fabrication de cet outil. |
US5674242A (en) * | 1995-06-06 | 1997-10-07 | Quanam Medical Corporation | Endoprosthetic device with therapeutic compound |
US5954744A (en) * | 1995-06-06 | 1999-09-21 | Quanam Medical Corporation | Intravascular stent |
US5851382A (en) * | 1995-12-18 | 1998-12-22 | Texaco Inc. | Selective hydrodesulfurization of cracked naphtha using hydrotalcite-supported catalysts |
DE69731444T2 (de) * | 1996-04-03 | 2005-10-13 | Arakawa Chemical Industries, Ltd. | Alkyliertes poröses harz, verfahren zu seiner herstellung und seine verwendung |
JPH101545A (ja) * | 1996-04-19 | 1998-01-06 | Pilot Ink Co Ltd | 熱可塑性樹脂組成物及びそれを用いた温度依存性変形−賦形性成形体 |
US5895718A (en) * | 1996-04-19 | 1999-04-20 | The Pilot Ink Co., Ltd. | Thermoplastic resin compositions and temperature-dependent shape-transformable/fixable products making use of the same |
US5889118A (en) * | 1996-06-03 | 1999-03-30 | Minnesota Mining And Manufacturing Company | Thermomorphic "smart" pressure sensitive adhesives |
US5910357A (en) * | 1996-07-12 | 1999-06-08 | Nitto Denko Corporation | Separation membrane and method of producing the same, and shape memory polymer composition |
US5756651A (en) * | 1996-07-17 | 1998-05-26 | Chronopol, Inc. | Impact modified polylactide |
US5955559A (en) * | 1996-09-17 | 1999-09-21 | Shell Oil Company | Cast polyurethane elastomers containing low polarity amine curing agents |
IL129342A (en) * | 1996-10-08 | 2004-12-15 | Alan Zamore | Irradiation conversion of thermoplastic to thermoset polymers |
JP4608032B2 (ja) * | 1997-06-18 | 2011-01-05 | 株式会社ブリヂストン | タイヤ用の加硫ゴム成形体 |
US6183248B1 (en) * | 1998-11-30 | 2001-02-06 | Muhammad Chishti | System and method for releasing tooth positioning appliances |
US6024764A (en) * | 1997-08-19 | 2000-02-15 | Intermedics, Inc. | Apparatus for imparting physician-determined shapes to implantable tubular devices |
US5922815A (en) * | 1997-12-15 | 1999-07-13 | General Electric Company | Process for producing blends of tackifying resins with low molecular weight polyphenylene ethers |
US6428572B2 (en) * | 1998-01-12 | 2002-08-06 | Menicon Co., Ltd. | Intraocular ring |
ES2265186T3 (es) | 1998-02-23 | 2007-02-01 | Mnemoscience Gmbh | Polimeros con memoria de forma. |
EP1056487B1 (en) | 1998-02-23 | 2004-05-12 | Massachusetts Institute Of Technology | Biodegradable shape memory polymers |
WO1999046327A1 (en) * | 1998-03-11 | 1999-09-16 | The Dow Chemical Company | STRUCTURES AND FABRICATED ARTICLES HAVING SHAPE MEMORY MADE FROM α-OLEFIN/VINYL OR VINYLIDENE AROMATIC AND/OR HINDERED ALIPHATIC VINYL OR VINYLIDENE INTERPOLYMERS |
US6217609B1 (en) * | 1998-06-30 | 2001-04-17 | Schneider (Usa) Inc | Implantable endoprosthesis with patterned terminated ends and methods for making same |
US6312461B1 (en) | 1998-08-21 | 2001-11-06 | John D. Unsworth | Shape memory tubular stent |
US6090872A (en) * | 1998-10-05 | 2000-07-18 | Fina Technology, Inc. | Polymerization process |
EP1000958B1 (en) * | 1998-11-12 | 2004-03-17 | Takiron Co. Ltd. | Shape-memory, biodegradable and absorbable material |
US20020015519A1 (en) * | 1998-12-11 | 2002-02-07 | Lord Corporation | Fiber substrate adhesion and coatings by contact metathesis polymerization |
US6530950B1 (en) * | 1999-01-12 | 2003-03-11 | Quanam Medical Corporation | Intraluminal stent having coaxial polymer member |
SE9900378D0 (sv) * | 1999-02-05 | 1999-02-05 | Forskarpatent I Syd Ab | Gels with shape memory |
US6365069B2 (en) * | 1999-03-19 | 2002-04-02 | Quantum Composites Inc. | Process of injection molding highly conductive molding compounds and an apparatus for this process |
US6436315B2 (en) * | 1999-03-19 | 2002-08-20 | Quantum Composites Inc. | Highly conductive molding compounds for use as fuel cell plates and the resulting products |
MXPA01012033A (es) | 1999-05-24 | 2002-11-04 | California Inst Of Techn | Catalizador de metatesis de metal-carbeno basado en inidazolidina. |
US6368346B1 (en) * | 1999-06-03 | 2002-04-09 | American Medical Systems, Inc. | Bioresorbable stent |
AUPQ170799A0 (en) * | 1999-07-20 | 1999-08-12 | Cardiac Crc Nominees Pty Limited | Shape memory polyurethane or polyurethane-urea polymers |
US6086204A (en) * | 1999-09-20 | 2000-07-11 | Magnante; Peter C. | Methods and devices to design and fabricate surfaces on contact lenses and on corneal tissue that correct the eye's optical aberrations |
US6627704B2 (en) * | 1999-12-01 | 2003-09-30 | General Electric Company | Poly(arylene ether)-containing thermoset composition, method for the preparation thereof, and articles derived therefrom |
US6905637B2 (en) * | 2001-01-18 | 2005-06-14 | General Electric Company | Electrically conductive thermoset composition, method for the preparation thereof, and articles derived therefrom |
US6352782B2 (en) * | 1999-12-01 | 2002-03-05 | General Electric Company | Poly(phenylene ether)-polyvinyl thermosetting resin |
US6432527B1 (en) * | 1999-12-14 | 2002-08-13 | 3M Innovative Properties Company | Embossed film having controlled tear |
US6521703B2 (en) * | 2000-01-18 | 2003-02-18 | General Electric Company | Curable resin composition, method for the preparation thereof, and articles derived thereform |
JP2001279524A (ja) * | 2000-03-30 | 2001-10-10 | Toyo Chem Co Ltd | 塩化ビニル系樹脂繊維 |
US20020007222A1 (en) * | 2000-04-11 | 2002-01-17 | Ashvin Desai | Method and apparatus for supporting a body organ |
US6679605B2 (en) * | 2000-05-22 | 2004-01-20 | Medennium, Inc. | Crystalline polymeric compositions for ophthalmic devices |
ATE275986T1 (de) | 2000-05-31 | 2004-10-15 | Mnemoscience Gmbh | Memory-thermoplaste und polymernetzwerke zum gewebeaufbau |
US6384176B1 (en) * | 2000-07-10 | 2002-05-07 | General Electric Co. | Composition and process for the manufacture of functionalized polyphenylene ether resins |
US6827325B2 (en) * | 2000-08-28 | 2004-12-07 | Johnson & Johnson Vision Care, Inc. | Shape memory polymer or alloy ophthalmic lens mold and methods of forming ophthalmic products |
US6607553B1 (en) | 2000-11-17 | 2003-08-19 | B. Braun Medical, Inc. | Method for deploying a thermo-mechanically expandable stent |
JP4613357B2 (ja) * | 2000-11-22 | 2011-01-19 | 株式会社ニコン | 光学的位置ずれ測定装置の調整装置および方法 |
EP1373339B1 (en) | 2001-01-24 | 2006-01-18 | Johnson & Johnson Vision Care, Inc. | Shape memory styrene copolymer |
US6593391B2 (en) * | 2001-03-27 | 2003-07-15 | General Electric Company | Abrasive-filled thermoset composition and its preparation, and abrasive-filled articles and their preparation |
US6878781B2 (en) * | 2001-03-27 | 2005-04-12 | General Electric | Poly(arylene ether)-containing thermoset composition in powder form, method for the preparation thereof, and articles derived therefrom |
WO2002083786A1 (en) | 2001-04-11 | 2002-10-24 | Cheong Seok Hong | Shape memory rubber composition |
US6794481B2 (en) * | 2001-06-28 | 2004-09-21 | Mitsubishi Gas Chemical Company, Inc. | Bifunctional phenylene ether oligomer, its derivatives, its use and process for the production thereof |
US6627673B2 (en) * | 2001-07-24 | 2003-09-30 | Kimberly-Clark Worldwide, Inc. | Methods of making humidity activated materials having shape-memory |
US6664436B2 (en) | 2001-07-24 | 2003-12-16 | Kimberly-Clark Worldwide, Inc. | Disposable products having humidity activated materials with shape-memory |
DE10152146A1 (de) * | 2001-10-25 | 2003-05-22 | Ticona Gmbh | Verfahren zur Reduzierung der Zähigkeit mechanisch zu bearbeitender Formteile aus Kunststoff sowie deren Verwendung |
US6860601B2 (en) * | 2002-02-06 | 2005-03-01 | John H. Shadduck | Adaptive optic lens system and method of use |
DE10208211A1 (de) * | 2002-02-26 | 2003-09-11 | Mnemoscience Gmbh | Polymere Netzwerke |
DE10215858A1 (de) | 2002-04-10 | 2004-03-18 | Mnemoscience Gmbh | Verfahren zur Haarbehandlung mit Formgedächtnispolymeren |
JP2005529095A (ja) | 2002-04-10 | 2005-09-29 | ネモサイエンス、ゲーエムベーハー | 毛髪において形状記憶効果を達成する方法 |
DE10217350C1 (de) * | 2002-04-18 | 2003-12-18 | Mnemoscience Gmbh | Polyesterurethane |
EP3311759B1 (en) | 2002-04-18 | 2020-12-09 | Helmholtz-Zentrum Geesthacht Zentrum für Material- und Küstenforschung GmbH | Shape memory polymeric sutures |
DE10217351B3 (de) * | 2002-04-18 | 2004-02-12 | Mnemoscience Gmbh | Interpenetrierende Netzwerke |
US20040030062A1 (en) | 2002-05-02 | 2004-02-12 | Mather Patrick T. | Castable shape memory polymers |
EP1519713B1 (de) | 2002-07-10 | 2010-09-15 | GKSS-Forschungszentrum Geesthacht GmbH | Wirkstofffreisetzungssysteme auf basis von bioabbaubaren oder biokompatiblen polymeren mit formgedaechtniseffekt |
WO2004011525A1 (en) | 2002-07-30 | 2004-02-05 | University Of Connecticut | Nonionic telechelic polymers incorporating polyhedral oligosilsesquioxane (poss) and uses thereof |
ES2373650T3 (es) * | 2002-10-11 | 2012-02-07 | University Of Connecticut | Policicloocteno reticulado. |
US7794494B2 (en) * | 2002-10-11 | 2010-09-14 | Boston Scientific Scimed, Inc. | Implantable medical devices |
US20050010275A1 (en) * | 2002-10-11 | 2005-01-13 | Sahatjian Ronald A. | Implantable medical devices |
US7524914B2 (en) * | 2002-10-11 | 2009-04-28 | The University Of Connecticut | Shape memory polymers based on semicrystalline thermoplastic polyurethanes bearing nanostructured hard segments |
DE60336074D1 (de) * | 2002-10-11 | 2011-03-31 | Univ Connecticut | Mischungen von amorphen und semikristallinen polymeren mit formgedächtniseigenscchaften |
US7413791B2 (en) | 2003-01-28 | 2008-08-19 | Matsushita Electric Works, Ltd. | Poly (phenylene ether) resin composition, prepreg, and laminated sheet |
JP4805148B2 (ja) | 2003-07-18 | 2011-11-02 | ボストン サイエンティフィック リミテッド | 医療器具 |
WO2006071520A2 (en) * | 2004-12-10 | 2006-07-06 | University Of Connecticut | Shape memory polymer orthodontic appliances, and methods of making and using the same |
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- 2003-10-10 AT AT03808216T patent/ATE498648T1/de not_active IP Right Cessation
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US20040122174A1 (en) | 2004-06-24 |
CA2501549C (en) | 2011-08-30 |
US7208550B2 (en) | 2007-04-24 |
JP2006503172A (ja) | 2006-01-26 |
US7371799B2 (en) | 2008-05-13 |
EP1558671A1 (en) | 2005-08-03 |
EP1558671B1 (en) | 2011-02-16 |
US20080249245A1 (en) | 2008-10-09 |
US20070135578A1 (en) | 2007-06-14 |
US7795350B2 (en) | 2010-09-14 |
AU2003300377B2 (en) | 2009-04-02 |
CA2501549A1 (en) | 2004-04-22 |
AU2003300377A1 (en) | 2004-05-04 |
DE60336074D1 (de) | 2011-03-31 |
WO2004033539A1 (en) | 2004-04-22 |
ATE498648T1 (de) | 2011-03-15 |
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