JPH10513378A - ヒアルロン酸、その誘導体、および半合成ポリマーで物体を被覆する方法 - Google Patents
ヒアルロン酸、その誘導体、および半合成ポリマーで物体を被覆する方法Info
- Publication number
- JPH10513378A JPH10513378A JP8523988A JP52398896A JPH10513378A JP H10513378 A JPH10513378 A JP H10513378A JP 8523988 A JP8523988 A JP 8523988A JP 52398896 A JP52398896 A JP 52398896A JP H10513378 A JPH10513378 A JP H10513378A
- Authority
- JP
- Japan
- Prior art keywords
- hyaluronic acid
- plasma
- semi
- coupling agent
- ester
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims abstract description 125
- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 title claims abstract description 100
- 229920002674 hyaluronan Polymers 0.000 title claims abstract description 100
- 229960003160 hyaluronic acid Drugs 0.000 title claims abstract description 99
- 238000000576 coating method Methods 0.000 title claims abstract description 26
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- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 claims description 17
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- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 10
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- LCLHHZYHLXDRQG-ZNKJPWOQSA-N pectic acid Chemical class O[C@@H]1[C@@H](O)[C@@H](O)O[C@H](C(O)=O)[C@@H]1OC1[C@H](O)[C@@H](O)[C@@H](OC2[C@@H]([C@@H](O)[C@@H](O)[C@H](O2)C(O)=O)O)[C@@H](C(O)=O)O1 LCLHHZYHLXDRQG-ZNKJPWOQSA-N 0.000 claims description 2
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- 210000002381 plasma Anatomy 0.000 claims 16
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
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- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical group CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 claims 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 1
- ISCMYZGMRHODRP-UHFFFAOYSA-N 3-(iminomethylideneamino)-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCN=C=N ISCMYZGMRHODRP-UHFFFAOYSA-N 0.000 claims 1
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- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 33
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
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- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 13
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- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
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- 238000009776 industrial production Methods 0.000 description 1
- 230000008611 intercellular interaction Effects 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- ARYZCSRUUPFYMY-UHFFFAOYSA-N methoxysilane Chemical compound CO[SiH3] ARYZCSRUUPFYMY-UHFFFAOYSA-N 0.000 description 1
- 238000001000 micrograph Methods 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
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- 238000006213 oxygenation reaction Methods 0.000 description 1
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- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
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- 239000010318 polygalacturonic acid Substances 0.000 description 1
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- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229940010747 sodium hyaluronate Drugs 0.000 description 1
- YWIVKILSMZOHHF-QJZPQSOGSA-N sodium;(2s,3s,4s,5r,6r)-6-[(2s,3r,4r,5s,6r)-3-acetamido-2-[(2s,3s,4r,5r,6r)-6-[(2r,3r,4r,5s,6r)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2- Chemical compound [Na+].CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 YWIVKILSMZOHHF-QJZPQSOGSA-N 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
- A61L31/08—Materials for coatings
- A61L31/10—Macromolecular materials
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/28—Materials for coating prostheses
- A61L27/34—Macromolecular materials
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
- A61L29/08—Materials for coatings
- A61L29/085—Macromolecular materials
Landscapes
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Vascular Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Surgery (AREA)
- Dermatology (AREA)
- Medicinal Chemistry (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Transplantation (AREA)
- Chemical & Material Sciences (AREA)
- Materials For Medical Uses (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Paints Or Removers (AREA)
- Media Introduction/Drainage Providing Device (AREA)
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.物体の表面を、ヒアルロン酸またはその誘導体で被覆する方法であって 、下記の工程: ヒアルロン酸またはその誘導体を、水溶液または有機溶媒中で、縮合剤または 二官能剤の存在下に、アルコキシシランカップリング剤と反応させて、ヒアルロ ン酸またはその誘導体とアルコキシシランカップリング剤との反応生成物を含有 する溶液を得る; 物体の表面をプラズマで処理する; 前記物体の処理表面を、ヒアルロン酸またはその誘導体とアルコキシシランカ ップリング剤との反応生成物を含有する溶液で被覆する; ヒアルロン酸またはその誘導体とアルコキシシランカップリング剤との前記反 応生成物を前記物体表面と反応させつつ、前記物体表面から溶液を除去する; を含んで成る方法。 2.アルコキシシランカップリング剤が、スルフヒドリル基またはアミノ基 を含有する請求項1に記載の方法。 3.アルコキシシランカップリング剤が、γ−アミノプロピルトリエトキシ シランまたはN−β−(アミノ−エチル)−γ−アミノプロピルトリメトキシシ ランである請求項1に記載の方法。 4.アルコキシシランカップリング剤とヒアルロン酸またはその誘導体との 反応が、 (i)前記縮合剤としての1−エチル−3−(3−ジメチルアミノプロピル) カルボジイミドの存在下水溶液中で;または (ii)前記縮合剤としてのジシクロヘキシルカルボジイミドの存在下有機溶媒 中で; 起こる請求項1に記載の方法。 5.アルコキシシランカップリング剤とヒアルロン酸またはその誘導体との 反応がさらに、N−ヒドロキシスクシンイミド、ヒドロキシスルホスクシンイミ ド、ヒドロキシベンゾトリアゾロ水和物、または同様の作用を持つそれらに類似 する化合物の存在下において起こる請求項1に記載の方法。 6.物体の表面を、半合成ポリマーで被覆する方法であって、下記工程: 半合成ポリマーを、水溶液または有機溶媒中で、縮合剤または二官能剤の存在 下に、アルコキシシランカップリング剤と反応させて、半合成ポリマーとアルコ キシシランカップリング剤との反応生成物を含有する溶液を得る; 物体の表面をプラズマで処理する; 前記物体の処理表面を、半合成ポリマーとアルコキシシランカップリング剤と の反応生成物を含有する溶液で被覆する; 半合成ポリマーとアルコキシシランカップリング剤との前記反応生成物を前記 物体表面と反応させつつ、前記物体表面から溶液を除去する; を含んで成る方法。 7.前記プラズマが、酸素プラズマ、空気プラズマ、水プラズマ、アルコー ルプラズマ、アセトンプラズマ、酸素添加化合物プラズマ、窒素プラズマ、アル ゴンプラズマ、または前記プラズマの2種またはそれ以上の混合プラズマである 請求項1または6に記載の方法。 8.半合成ポリマーとアルコキシシランカップリング剤との反応が、 (i)前記縮合剤としての1−エチル−3−(3−ジメチルアミノプロピル) カルボジイミドの存在下水溶液中で;または (ii)前記縮合剤としてのジシクロヘキシルカルボジイミドの存在下有機溶媒 中で; 起こる請求項6に記載の方法。 9.半合成ポリマーとアルコキシシランカップリング剤との反応が、N−ヒ ドロキシスクシンイミド、ヒドロキシスルホスクシンイミド、ヒドロキシベンゾ トリアゾロ水和物、または同様の作用を持つそれらに類似する化合物の存在下に おいて起こる請求項6に記載の方法。 10.物体の表面を、ヒアルロン酸またはその誘導体で被覆する方法であっ て、下記工程: 物体の表面をプラズマで処理する; 物体の処理表面を、ポリエチレンイミンを含有する溶液に浸漬する; カルボジイミド、ならびにN−ヒドロキシスクシンイミド、ヒドロキシスルホ スクシンイミド、ヒドロキシベンゾトリアゾロ水和物などから成る群から選択さ れる物質の存在下に、浸漬された物体の処理表面を、ヒアルロン酸またはその誘 導体と反応させる; を含んで成る方法。 11.ヒアルロン酸誘導体が、 (i)ヒアルロン酸の全または部分ベンジルエステル;または (ii)ヒアルロン酸の全または部分エチルエステル; である請求項1または10に記載の方法。 12.処理表面とヒアルロン酸またはその誘導体との反応が、 (i)1−エチル−3−(3−ジメチルアミノプロピルカルボジイミド)の存 在下の水溶液中で;または (ii)ヒドロキシスクシンイミドおよびジシクロヘキシルカルボジイミドの存 在下の有機溶媒中; 行われる請求項10に記載の方法。 13.物体の表面を、半合成ポリマーで被覆する方法であって、下記工程: 物体の表面をプラズマで処理する; 物体の処理表面を、ポリエチレンイミンを含有する溶液に浸漬する; カルボジイミド、ならびにN−ヒドロキシスクシンイミド、ヒドロキシスルホ スクシンイミド、ヒドロキシベンゾトリアゾロ水和物などから成る群から選択さ れる物質の存在下に、浸漬された物体の処理表面を、半合成ポリマーと反応させ る; を含んで成る方法。 14.半合成ポリマーが、ヒアルロン酸の多価アルコールのエステル、酸性 多糖の分子内エステル、カルボキシメチルセルロースのエステル、カルボキシメ チルキチンのエステル、カルボキシメチルアミドのエステル、カルボキシル多糖 の活性エステル、ヒアルロン酸の硫酸化エステル、アルギン酸のエステル、キチ ンのエステル、キトサンのエステル、ペクチン酸のエステル、およびペクチニン 酸のエステルから成る群から選択される請求項6または13に記載の方法。 15.処理表面と半合成ポリマーとの反応が、 (i)ヒドロキシスクシンイミドおよび1−エチル−3−(3−ジメチルアミ ノプロピルカルボジイミド)の存在下水溶液中で;または (ii)ヒドロキシスクシンイミドおよびジシクロヘキシルカルボジイミドの存 在下水溶液中で; 行われる請求項13に記載の方法。 16.被覆される物体が、生体液と適合性の物質から成る請求項1、6、1 0または13に記載の方法。 17.被覆される物体が、ポリマー物質、セラミック物質または金属性物質 から成る請求項10または13に記載の方法。 18.被覆される物体が、チタン、チタン合金、スチール、およびクロム− コバルト合金から成る群から選択される金属性物質から成る請求項10または1 3に記載の方法。 19.被覆される物体が、カテーテル、血液バッグ、ガイドチャネル、探針 、注射器、外科器具、容器、濾過システム、人工の腱、関節、ピン、心臓弁、骨 、心臓血管代替物、移植組織、静脈カテーテル、眼内レンズ、コンタクトレンズ 、軟組織代替物、人工腎臓、血液酸素供給器、人工の心臓、膵臓および肝臓から 成る群から選択される請求項1、6、10または13に記載の方法。 20.被覆される物体が、実験器具の部品、細胞および組織培養用の皿、細 胞およ組織再生用の皿、ならびにペプチド、タンパク質および抗体のような活性 成分の支持物から成る群から選択される請求項1、6、10または13に記載の 方法。
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
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IT95PD000030A IT1282187B1 (it) | 1995-02-07 | 1995-02-07 | Processo di rivestimento di oggetti con acido ialuronico e derivati |
IT95A000030 | 1995-08-01 | ||
IT95A000243 | 1995-12-20 | ||
ITPD950243 IT1282218B1 (it) | 1995-12-20 | 1995-12-20 | Processo di rivestimento di oggetti con acido ialuronico o suoi derivati. |
PCT/EP1996/000509 WO1996024392A1 (en) | 1995-02-07 | 1996-02-07 | Process for the coating of objects with hyaluronic acid, derivatives thereof, and semisynthetic polymers |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2007313385A Division JP2008080153A (ja) | 1995-02-07 | 2007-12-04 | ヒアルロン酸、その誘導体、および半合成ポリマーで物体を被覆する方法 |
Publications (1)
Publication Number | Publication Date |
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JPH10513378A true JPH10513378A (ja) | 1998-12-22 |
Family
ID=26331822
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
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JP8523988A Withdrawn JPH10513378A (ja) | 1995-02-07 | 1996-02-07 | ヒアルロン酸、その誘導体、および半合成ポリマーで物体を被覆する方法 |
JP2007313385A Withdrawn JP2008080153A (ja) | 1995-02-07 | 2007-12-04 | ヒアルロン酸、その誘導体、および半合成ポリマーで物体を被覆する方法 |
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JP2007313385A Withdrawn JP2008080153A (ja) | 1995-02-07 | 2007-12-04 | ヒアルロン酸、その誘導体、および半合成ポリマーで物体を被覆する方法 |
Country Status (18)
Country | Link |
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US (1) | US6129956A (ja) |
EP (1) | EP0808181B1 (ja) |
JP (2) | JPH10513378A (ja) |
CN (1) | CN1141149C (ja) |
AT (1) | ATE219381T1 (ja) |
AU (1) | AU704047B2 (ja) |
BR (1) | BR9607516A (ja) |
CA (1) | CA2212519C (ja) |
CZ (1) | CZ293637B6 (ja) |
DE (1) | DE69621911T2 (ja) |
ES (1) | ES2179930T3 (ja) |
HU (1) | HU219815B (ja) |
MX (1) | MX9706054A (ja) |
NO (1) | NO313687B1 (ja) |
NZ (1) | NZ302264A (ja) |
PL (1) | PL182804B1 (ja) |
TR (1) | TR199700760T1 (ja) |
WO (1) | WO1996024392A1 (ja) |
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JP2001129074A (ja) * | 1999-11-08 | 2001-05-15 | Asahi Intecc Co Ltd | 潤滑性ガイディングカテーテルおよびスプリングガイドワイヤ |
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JP2007046056A (ja) * | 2005-08-05 | 2007-02-22 | Becton Dickinson & Co | 非特異的タンパク質結合および細胞付着に対する抵抗性がある表面を生成する方法 |
JP2009143825A (ja) * | 2007-12-12 | 2009-07-02 | Shiseido Co Ltd | 表面処理粉体及びそれを配合した化粧料 |
JP2020520262A (ja) * | 2017-05-12 | 2020-07-09 | マイクロベンション インコーポレイテッドMicrovention, Inc. | 医療機器 |
Also Published As
Publication number | Publication date |
---|---|
DE69621911T2 (de) | 2003-01-30 |
PL321781A1 (en) | 1997-12-22 |
CZ250997A3 (cs) | 1998-01-14 |
ATE219381T1 (de) | 2002-07-15 |
NO973648L (no) | 1997-10-03 |
AU4788496A (en) | 1996-08-27 |
HUP9702114A3 (en) | 1998-06-29 |
US6129956A (en) | 2000-10-10 |
HU219815B (hu) | 2001-08-28 |
HUP9702114A2 (hu) | 1998-04-28 |
CN1173824A (zh) | 1998-02-18 |
CA2212519C (en) | 2005-08-23 |
PL182804B1 (pl) | 2002-03-29 |
TR199700760T1 (xx) | 1998-02-21 |
NZ302264A (en) | 1998-02-26 |
EP0808181B1 (en) | 2002-06-19 |
NO973648D0 (no) | 1997-08-07 |
EP0808181A1 (en) | 1997-11-26 |
NO313687B1 (no) | 2002-11-18 |
ES2179930T3 (es) | 2003-02-01 |
AU704047B2 (en) | 1999-04-15 |
WO1996024392A1 (en) | 1996-08-15 |
DE69621911D1 (de) | 2002-07-25 |
CN1141149C (zh) | 2004-03-10 |
CZ293637B6 (cs) | 2004-06-16 |
MX9706054A (es) | 1998-07-31 |
BR9607516A (pt) | 1997-12-30 |
JP2008080153A (ja) | 2008-04-10 |
CA2212519A1 (en) | 1996-08-15 |
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