JP2010132868A - アリールアジド基を有する高分子重合開始剤およびこれを利用した環式オレフィン共重合体表面改質方法。 - Google Patents
アリールアジド基を有する高分子重合開始剤およびこれを利用した環式オレフィン共重合体表面改質方法。 Download PDFInfo
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- JP2010132868A JP2010132868A JP2009215743A JP2009215743A JP2010132868A JP 2010132868 A JP2010132868 A JP 2010132868A JP 2009215743 A JP2009215743 A JP 2009215743A JP 2009215743 A JP2009215743 A JP 2009215743A JP 2010132868 A JP2010132868 A JP 2010132868A
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- 229920000089 Cyclic olefin copolymer Polymers 0.000 title claims abstract description 118
- 239000004713 Cyclic olefin copolymer Substances 0.000 title claims abstract description 112
- 238000000034 method Methods 0.000 title claims abstract description 38
- 239000003505 polymerization initiator Substances 0.000 title abstract description 61
- 125000003118 aryl group Chemical group 0.000 title abstract description 17
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 title abstract description 17
- 229920000642 polymer Polymers 0.000 claims abstract description 99
- 239000000758 substrate Substances 0.000 claims abstract description 57
- 150000001875 compounds Chemical class 0.000 claims abstract description 21
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 43
- 239000010409 thin film Substances 0.000 claims description 39
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 15
- DQHTXJNVTIBYSA-UHFFFAOYSA-N dimethyl-[3-(2-methylprop-2-enoylamino)propyl]-(3-sulfopropyl)azanium;hydroxide Chemical compound [OH-].CC(=C)C(=O)NCCC[N+](C)(C)CCCS(O)(=O)=O DQHTXJNVTIBYSA-UHFFFAOYSA-N 0.000 claims description 15
- 239000001301 oxygen Substances 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 14
- 238000009832 plasma treatment Methods 0.000 claims description 13
- 239000000178 monomer Substances 0.000 claims description 12
- 229920001577 copolymer Polymers 0.000 claims description 10
- -1 cyclic olefin Chemical class 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 8
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 7
- 229910052723 transition metal Inorganic materials 0.000 claims description 7
- 150000003624 transition metals Chemical class 0.000 claims description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 6
- 238000012546 transfer Methods 0.000 claims description 6
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 5
- 238000004140 cleaning Methods 0.000 claims description 5
- 230000000379 polymerizing effect Effects 0.000 claims description 5
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 4
- 238000004528 spin coating Methods 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
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- 238000012986 modification Methods 0.000 claims description 3
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- 239000012327 Ruthenium complex Substances 0.000 claims description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 2
- 238000002715 modification method Methods 0.000 claims 5
- 238000005406 washing Methods 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 1
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 14
- 229940093476 ethylene glycol Drugs 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000012844 infrared spectroscopy analysis Methods 0.000 description 8
- 238000004833 X-ray photoelectron spectroscopy Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
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- 238000001179 sorption measurement Methods 0.000 description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 230000008859 change Effects 0.000 description 6
- 125000000524 functional group Chemical group 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- 238000004566 IR spectroscopy Methods 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
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- 238000000576 coating method Methods 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 238000010560 atom transfer radical polymerization reaction Methods 0.000 description 4
- ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
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- 239000012459 cleaning agent Substances 0.000 description 3
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- 239000003999 initiator Substances 0.000 description 3
- 239000002798 polar solvent Substances 0.000 description 3
- 239000013076 target substance Substances 0.000 description 3
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 238000000089 atomic force micrograph Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 238000007646 gravure printing Methods 0.000 description 2
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- 229910052742 iron Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 2
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- 0 *Cc(cc1)ccc1C(N)=O Chemical compound *Cc(cc1)ccc1C(N)=O 0.000 description 1
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
- 229910021590 Copper(II) bromide Inorganic materials 0.000 description 1
- 238000000018 DNA microarray Methods 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000012620 biological material Substances 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
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- 238000006392 deoxygenation reaction Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002433 hydrophilic molecules Chemical class 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229940127554 medical product Drugs 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 238000009828 non-uniform distribution Methods 0.000 description 1
- 101150111393 oli gene Proteins 0.000 description 1
- 238000007557 optical granulometry Methods 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—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 a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31855—Of addition polymer from unsaturated monomers
- Y10T428/31909—Next to second addition polymer from unsaturated monomers
- Y10T428/31913—Monoolefin polymer
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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)
- Treatments Of Macromolecular Shaped Articles (AREA)
- Polymerisation Methods In General (AREA)
Abstract
Description
環式オレフィン共重合体基板の表面の状態による水に対する接触角を撮影した。図1は、環式オレフィン共重合体基板に何の処理もしない状態で基板表面と水との間の接触状態を撮影した写真であり、図2は、環式オレフィン共重合体基板の表面を酸素プラズマ処理した後に基板表面と水との間の接触状態を撮影した写真である。図3は、高分子重合開始剤を前記プラズマ処理した環式オレフィン共重合体基板に固定した後に基板表面と水との間の接触状態を撮影した写真である。二つの物質間の接触角は、基板の表面と水との間の接触状態を観察することによって測定することができる。前記接触角θの測定は、基板の表面に水滴を落とした後に基板の界面と水滴が形成する角度を測定して、表面の親水性および疎水性の程度を確認する方法に測定手続きが簡単で、容易に表面改質程度を分かることができて表面研究に広範囲に利用されている方法である。
環式オレフィン共重合体基板表面に高分子重合開始剤が導入されたのかの可否は、エックス線光電子分光分析(X−ray photoelectron spectroscopy)を通じても確認することができた。
環式オレフィン共重合体表面にポリ(オリゴ(エチレングリコール)メチルメタクリルレート(poly(oligo(ethylene glycol) methacrylate))薄膜を形成した。
本実験形態3では、実施形態1の環式オレフィン共重合体表面にポリ(オリゴ(エチレングリコール)メチルメタクリルレート薄膜が形成されたのかの可否を赤外線分光分析を利用して確認した。
環式オレフィン共重合体表面にポリ((3−(メタクリロイルアミノ)プロピル)−ジメチル(3−スルホプロピル)アンモニウムヒドロキシド)薄膜を形成した。
本実験形態4では、実施形態2の環式オレフィン共重合体表面にポリ((3−(メタクリロイルアミノ)プロピル)−ジメチル(3−スルホプロピル)アンモニウムヒドロキシド薄膜が形成の可否を赤外線分光分析および原子間力顕微鏡(Atomic Force Microscope)写真を通じて確認した。
環式オレフィン共重合体表面に形成されたポリ((3−(メタクリロイルアミノ)プロピル)−ジメチル(3−スルホプロピル)アンモニウムヒドロキシド高分子薄膜は、赤外線分光分析を通じて確認した。分析の結果、ポリ((3−(メタクリロイルアミノ)プロピル)−ジメチル(3−スルホプロピル)アンモニウムヒドロキシド薄膜が特徴的に有する元素間の結合振動エネルギであるC=Oストレッチング、N−Hベンディング、S=Oの対称形ストレッチングピークが各々1623cm-1、1570cm-1、1220cm-1で確認された。
環式オレフィン共重合体表面に形成されたポリ((3−(メタクリロイルアミノ)プロピル)−ジメチル(3−スルホプロピル)アンモニウムヒドロキシド高分子薄膜は、原子間力顕微鏡写真分析を通じて間接的に確認した。
Claims (13)
- 前記化学式1の化合物を前記環式オレフィン共重合体基板に塗布する前に前記環式オレフィン共重合体基板を酸素プラズマ処理する段階をさらに含むことを特徴とする請求項2に記載の環式オレフィン共重合体表面改質方法。
- 前記酸素プラズマ処理段階の直前に前記環式オレフィン共重合体基板を洗浄する段階をさらに含むことを特徴とする請求項3に記載の環式オレフィン共重合体表面改質方法。
- 前記洗浄段階は、超音波を加えて洗浄する段階であることを特徴とする請求項4に記載の環式オレフィン共重合体表面改質方法。
- 前記紫外線は、200nmから300nmの波長に、5〜60分間照射されることを特徴とする請求項2に記載の環式オレフィン共重合体表面改質方法。
- 前記塗布する段階は、スピンコーティングする段階であることを特徴とする請求項2に記載の環式オレフィン共重合体表面改質方法。
- 前記高分子を重合させる段階は、高分子の単量体を遷移金属触媒を利用して、原子移動ラジカル高分子重合反応を進行させる段階であることを特徴とする請求項2に記載の環式オレフィン共重合体表面改質方法。
- 前記遷移金属触媒は、銅錯化合物、パラジウム錯化合物、ニッケル錯化合物、鉄錯化合物、またはルテニウム錯化合物であることを特徴とする請求項8に記載の環式オレフィン共重合体表面改質方法。
- 前記高分子の単量体は、アクリル系単量体、メタアクリル系単量体、またはアクリルアミド系単量体であることを特徴とする請求項8に記載の環式オレフィン共重合体表面改質方法。
- 前記アクリル系単量体は、オリゴ(エチレングリコール)メタクリルレートまたは(3−(メタクリロイルアミノ)プロピル)−ジメチル(3−スルホプロピル)アンモニウムヒドロキシドであることを特徴とする請求項10に記載の環式オレフィン共重合体表面改質方法。
- ポリ(オリゴ(エチレングリコール)メチルメタクリルレート)薄膜が形成された環式オレフィン共重合体。
- ポリ((3−(メタクリロイルアミノ)プロピル)−ジメチル(3−スルホプロピル)アンモニウムヒドロキシド)薄膜が形成された環式オレフィン共重合体。
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KR20080123239 | 2008-12-05 | ||
KR1020090035119A KR20100065042A (ko) | 2008-12-05 | 2009-04-22 | 아릴 아자이드기를 갖는 고분자 중합 개시제 및 이를 이용한 고리형 올레핀 공중합체 표면 개질 방법 |
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Country Status (3)
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US (1) | US8541621B2 (ja) |
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JP2019534078A (ja) * | 2016-06-24 | 2019-11-28 | サントル・ナシオナル・ドゥ・ラ・ルシェルシュ・シアンティフィクCentre National De Larecherche Scientifique | クリップケミストリーを用いた特性付与化合物でグラフト化した表面修飾ポリマー基質 |
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US20110186165A1 (en) * | 2009-10-05 | 2011-08-04 | Borenstein Jeffrey T | Three-dimensional microfluidic platforms and methods of use and manufacture thereof |
CN110114146B (zh) * | 2016-12-20 | 2021-11-19 | 生物辐射实验室股份有限公司 | 微流体装置上的uv接枝 |
US11491179B2 (en) | 2017-04-12 | 2022-11-08 | Urigen Pharmaceuticals, Inc. | Article of manufacture comprising local anesthetic, buffer, and glycosaminoglycan in syringe with improved stability |
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AU2001296551A1 (en) | 2000-10-05 | 2002-04-15 | E.I. Du Pont De Nemours And Company | Polymeric microfabricated fluidic device suitable for ultraviolet detection |
DE60125409T2 (de) | 2000-10-06 | 2007-09-27 | Carnegie Mellon University | Polymerisationsverfahren für ionische monomere |
KR100733923B1 (ko) | 2004-07-07 | 2007-07-02 | 주식회사 엘지화학 | 극성 작용기를 갖는 고리형 올레핀 중합체 제조용 촉매시스템, 이를 이용한 중합체 제조방법과 이 방법에 의해제조된 올레핀 중합체 및 상기 중합체를 포함하는 광학이방성 필름 |
EP1731965B1 (en) | 2005-06-10 | 2012-08-08 | Obducat AB | Imprint stamp comprising cyclic olefin copolymer |
KR100842440B1 (ko) | 2006-10-20 | 2008-07-01 | 손상호 | 칼라필터 기능을 갖는 고분자 기판과 그 제조방법 |
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2009
- 2009-09-09 US US12/556,546 patent/US8541621B2/en not_active Expired - Fee Related
- 2009-09-16 DE DE200910029488 patent/DE102009029488A1/de not_active Withdrawn
- 2009-09-17 JP JP2009215743A patent/JP2010132868A/ja active Pending
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JP2019534078A (ja) * | 2016-06-24 | 2019-11-28 | サントル・ナシオナル・ドゥ・ラ・ルシェルシュ・シアンティフィクCentre National De Larecherche Scientifique | クリップケミストリーを用いた特性付与化合物でグラフト化した表面修飾ポリマー基質 |
JP7016355B2 (ja) | 2016-06-24 | 2022-02-21 | サントル・ナシオナル・ドゥ・ラ・ルシェルシュ・シアンティフィク | クリップケミストリーを用いた特性付与化合物でグラフト化した表面修飾ポリマー基質 |
Also Published As
Publication number | Publication date |
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US8541621B2 (en) | 2013-09-24 |
DE102009029488A1 (de) | 2010-06-17 |
US20100143735A1 (en) | 2010-06-10 |
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