JP2013514841A - コーティング剤およびコーティングされた物品 - Google Patents
コーティング剤およびコーティングされた物品 Download PDFInfo
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- JP2013514841A JP2013514841A JP2012544957A JP2012544957A JP2013514841A JP 2013514841 A JP2013514841 A JP 2013514841A JP 2012544957 A JP2012544957 A JP 2012544957A JP 2012544957 A JP2012544957 A JP 2012544957A JP 2013514841 A JP2013514841 A JP 2013514841A
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- polymer
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- coating agent
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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
- C08F8/00—Chemical modification by after-treatment
- C08F8/42—Introducing metal atoms or metal-containing groups
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- 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
- A61L29/04—Macromolecular materials
- A61L29/06—Macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
- A61L29/08—Materials for coatings
- A61L29/085—Macromolecular materials
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
- A61L29/14—Materials characterised by their function or physical properties, e.g. lubricating compositions
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- A—HUMAN NECESSITIES
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- A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
- A61L29/14—Materials characterised by their function or physical properties, e.g. lubricating compositions
- A61L29/16—Biologically active materials, e.g. therapeutic substances
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- A—HUMAN NECESSITIES
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- 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
- A61L31/02—Inorganic materials
- A61L31/022—Metals or alloys
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- A—HUMAN NECESSITIES
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- 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
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- A—HUMAN NECESSITIES
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- 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
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- 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
- A61L31/14—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- 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
- A61L31/14—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
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- A61L33/00—Antithrombogenic treatment of surgical articles, e.g. sutures, catheters, prostheses, or of articles for the manipulation or conditioning of blood; Materials for such treatment
- A61L33/0005—Use of materials characterised by their function or physical properties
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
- B05D3/06—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by exposure to radiation
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- C08F267/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated polycarboxylic acids or derivatives thereof as defined in group C08F22/00
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D131/00—Coating compositions based on 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; Coating compositions based on derivatives of such polymers
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D135/00—Coating compositions based on 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 carboxyl radical, and containing at least another carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Coating compositions based on derivatives of such polymers
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- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Surgery (AREA)
- Engineering & Computer Science (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Molecular Biology (AREA)
- Biomedical Technology (AREA)
- Physics & Mathematics (AREA)
- Plasma & Fusion (AREA)
- Hematology (AREA)
- Inorganic Chemistry (AREA)
- Materials For Medical Uses (AREA)
- Paints Or Removers (AREA)
- Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
- Laminated Bodies (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
本出願は、2009年12月21日に出願された米国仮特許出願第61/288,803号(発明の名称「SURFACE PRIMERS」、代理人管理番号16420.0001USP1)に対して、米国特許法§119(e)の下、利益を主張する。この出願の内容はすべての目的のためにその全体が本明細書において参照として援用される。
シリコーン、ステンレス鋼、およびポリエチレンなどの材料で製作された基材に塗布するのに有用なコーティング剤が記述される。いくつかの態様では、コーティング剤は、表面プライマー剤として有用であり、追加のコーティング層を塗布することができるベースコーティングを提供することができる。その他の態様では、コーティング剤は、それ自体が所望の特徴を基材表面に提供することができる。表面にコーティング剤を含む物品についても記述される。
医療用物品は、いくつかの材料から製作することができる。例えば、医療用物品を製作するのに利用されるいくつかの一般的な材料には、金属および合金、セラミック、ガラス、ガラス−セラミック、ポリマー材料、複合体、セメント、不織布および織布が含まれる。人体の環境は驚くほど過酷で攻撃的であり、したがって、人体で使用される材料の選択では、材料の性質、医療用物品の用途、および体内に滞留する持続時間などの要因が考慮される。人体に使用される一般的なポリマー材料には、シリコーンおよびその他のプラスチックが含まれ、一方、金属には、ステンレス鋼、コバルト−クロム合金、チタンおよびチタン合金、形状記憶合金、およびタンタルが含まれる。
第1の一般的な態様では、材料表面上にプライミングまたはベースコーティング層を提供するためのコーティング剤について記述する。そのようなコーティング剤を調製する方法と、移植可能な医療用物品の表面などの表面をコーティングするのにそのようなコーティング剤を使用する方法とについても記述する。別の態様では、この開示は、そのようなコーティング剤でコーティングされた材料表面、ならびにそのような材料表面を作製し使用する方法と、得られる物品について記述する。そのような「プライマー」組成物は、組成が同じおよび/または異なるいずれかの追加のコーティング「層」の使用を容易にすることができる。
本明細書に記述される本発明の実施形態は、余すところのないものではなく、または開示された厳密な形に本発明を限定するものではない。むしろ実施形態は、当業者が本発明の原理および実施を認めることができ理解することができるように選択され記述される。本出願は、本発明の対象の適応例または変形例を包含するものである。
により表されるペンダントアミドシロキサン基を形成するための、3−アミノプロピルメチルビス(トリメチルシロキシ)シランと、ポリ(無水マレイン酸−alt−1−オクタデゼン)の無水基との反応生成物とすることができる。
X1−Y−X2 (III)
式中、Yは、少なくとも1個の酸性基、塩基性基、またはこれらの塩を含有するラジカルであり、X1およびX2はそれぞれ独立して、潜在的光反応性基を含有するラジカルである。
Lubricent(商標):イソプロピルアルコールに溶解した光反応性化合物と組み合わせたヒドロゲル形成ポリマーのブレンドからなる親水性コーティングであって、Harland Medical、Eden Prairie、MNからLubricent(商標)460という製品名で市販されているもの。
フォト−ポリ(オクタデセン−alt−無水マレイン酸)シラン−(フォト−POMAS)の合成。
フォト−POMASによるシリコーンチューブのコーティング。
潤滑性コーティング。
コンゴレッド染色。
摩擦試験。
超疎水性コーティング。
細胞毒性。
光パターニング
基材上へのコーティング剤の選択的な塗布は、フォト−POMASコーティングを塗布させ、その後このコーティングを、下記の通りマスクと併せて活性化エネルギーに曝露することによって実証された。この実施例での基材は、シリコーンディスクを含んでいた(1.2cm、実施例16に記述されるように調製された。)。コーティングの塗布前に、シリコーンディスクをイソプロピルアルコール(IPA)に浸漬し、その後、15分間超音波処理することによって、清浄化した。次いでディスクを、ロッカー上に5分間配置した。
フォト−POMASによるステンレス鋼のコーティング。
ポリ(1−オクタデセン−alt−無水マレイン酸)ベンゾフェノン(POMA−BP)の合成。
POMA−BPによるシリコーンのコーティング。
比較例。ポリ(無水マレイン酸−alt−1−オクタデセン)シラン(POMA−S)の合成。
比較例。POMA−Sによるシリコーンのコーティング。
比較例。ポリ(メチルビニルエーテル−alt−無水マレイン酸)(PMVEMA−BP)の合成。
比較例。PMVEMA−BPによるシリコーンのコーティング。
ポリ両性イオンブラシコーティングに基づいたコーティングの不活性化。
パーフルオロフェニルアジド−ポリ(オクタデセン−alt−無水マレイン酸)シランの合成と、シリコーンチューブのコーティング(パーフルオロフェニルアジド−POMAS)。
パーフルオロフェニルアジド−POMASによるコーティング。
ポリマー組成物の一部としての、不活性化PEG基の組込み。
非共有結合基、パーフルオロフェニルアジド−POMAS、および開始剤(ATRP開始剤)を含むポリマー。
ポリ両性イオングラフト。
アセトニドで保護されたドーパミンの合成。
アセトニドで保護されたドーパミンの、6−マレイミド−ヘキサノイルクロリドへの添加。
Mal−Hex−ドーパミン−アセトニドと無水マレイン酸との共重合。
HDPEおよびシリコーンに対するドーパミン−官能基化無水マレイン酸コポリマーによるコーティング。
ベンゾフェノン官能基化マレイミドヘキサンアミドの合成。
潜在的反応性基を含有するモノマーと、結合基およびビニルピロリドンを含有するモノマーとの共重合。
ペンダントドーパミン、ペンダントベンゾフェノンVPコポリマーにおけるアセトニドの脱保護。
非共有結合基および潜在的反応性基を含有する無水マレイン酸コポリマーの合成。
Claims (39)
- ケイ素を含む基材と、前記基材の表面に配置されたコーティングとを含む物品であって、前記コーティングが:(a)ポリマーと、(b)前記ポリマーからペンダント状態にある1個または複数の潜在的反応性基と、(c)前記基材と相互に作用するように選択された1個または複数の非共有結合基とを含む物品。
- 前記基材がシリコーンを含む、請求項1に記載の物品。
- 前記非共有結合基がシロキサン基である、請求項1に記載の物品。
- 前記非共有結合基が、C4〜C20アルキル基、ポリアミド、フェノール樹脂、カテコール、ポリエチレングリコール、ポリアクリレート、ポリウレタン、ポリカーボネート、ポリエステル、ポリエチレン、ポリプロピレン、もしくはポリエーテル、またはこれらのいずれかの組合せから選択される、請求項1に記載の物品。
- 前記ポリマーが、ポリオレフィン、ビニルポリマー、ポリエステル、ポリブチレン、ポリエーテル、ポリアミド、ポリウレタン、ポリカーボネート、ポリスチレン、ポリ(メチル)メタクリレート、ポリアクリロニトリル、ポリ(酢酸ビニル)、ポリ(ビニルアルコール)、ポリ塩化(ビニル)などの塩素含有ポリマー、ポリオキシメチレン、ポリイミド、フェノール樹脂、アミノ−エポキシ樹脂、またはこれらのいずれかのコポリマーもしくは組合せから選択される、請求項1に記載の物品。
- 前記ポリマーが、ポリマレイン酸誘導体を含むポリマーである、請求項1に記載の物品。
- 前記非共有結合基が、ポリマー主鎖の一部である、請求項1に記載の物品。
- 前記ポリマーがアルキルを含む、請求項7に記載の物品。
- 前記非共有結合基が、前記ポリマー主鎖からペンダント状態にある、請求項1に記載の物品。
- 前記潜在的反応性基が光反応性基を含む、請求項1に記載の物品。
- 前記光反応性基が、アントラキノン、アリールアジド、アリールケトン、アリールケトン誘導体、またはこれらのいずれか1種もしくは複数の混合物から選択される、請求項10に記載の物品。
- 前記潜在的反応性基が熱反応性基を含む、請求項1に記載の物品。
- 前記潜在的反応性基がハロフェニルアジドである、請求項1に記載の物品。
- 活性剤をさらに含む、請求項1に記載の物品。
- 前記活性剤が開始剤基である、請求項14に記載の物品。
- 前記開始剤基が、有機ハロゲン化物またはベンゾフェノンを含む、請求項15に記載の物品。
- 前記活性剤が不活性化基である、請求項14に記載の物品。
- 前記不活性化基が、カルボキシレート、スルフェート、ヒドロキシ、アミン、メチル、ポリエチレングリコール、シロキシル、もしくはパーフルオロ基、またはこれらの任意の組合せから選択される、請求項17に記載の物品。
- オーバーコート層をさらに含む、請求項1に記載の物品。
- 前記オーバーコートが、ビニルピロリドン、ビニルアルキレン、ビニルアルコール、酢酸ビニル、ポリエチレングリコール、ポリエーテル、アクリルアミド、アルギネート、ヘパリン、ヒアルロン酸、ポリリジン、糖、キトサン、デキストラン、ゼラチン、コラーゲン、セルロース、ケラチン、ポリペプチド、ヌクレオチド、タンパク質、メチルメタクリレート、ヒドロキシエチルメタクリレート、ヒドロキシエチルアクリレート、メタクリル酸、アクリル酸、グリセロールアクリレート、グリセロールメタクリレート、メタクリルアミド、アルキレンオキシド、第4級アンモニウムエチレンイミン、もしくはこれらのコポリマーまたは組合せを含む、請求項19に記載の物品。
- (a)ポリマレイン酸誘導体を含むポリマーと、(b)1個または複数の潜在的反応性基と、(c)1個または複数の非共有結合基とを含むコーティング剤であって、前記非共有結合基が、前記コーティング剤が塗布される基材と相互に作用するように選択される、コーティング剤。
- 前記ポリマレイン酸誘導体が、誘導体化ポリ(アルケン−co−無水マレイン酸)である、請求項21に記載のコーティング剤。
- 前記非共有結合基が、前記ポリマーからペンダント状態にある、請求項21に記載のコーティング剤。
- 前記非共有結合基が、前記ポリマー主鎖の一部である、請求項21に記載のコーティング剤。
- 前記非共有結合基が、シロキサン、C4〜C20アルキル基、ポリアミド、フェノール樹脂、カテコール、1種または複数のポリエチレングリコール、アクリレート、ポリアクリレート、ポリウレタン、ポリカーボネート、ポリエステル、ポリエチレン、ポリプロピレン、もしくはポリエーテル、またはこれらの任意の組合せから選択される、請求項21に記載のコーティング剤。
- 前記潜在的反応性基が、前記ポリマーからペンダント状態にある、請求項21に記載のコーティング剤。
- 前記潜在的反応性基が光反応性基を含む、請求項21に記載のコーティング剤。
- 前記光反応性基が、アントラキノン、アリールアジド、アリールケトン、アリールケトン誘導体、またはこれらのいずれか1種もしくは複数の混合物から選択される、請求項27に記載のコーティング剤。
- 前記潜在的反応性基が熱反応性基を含む、請求項21に記載のコーティング剤。
- 前記潜在的反応性基がハロフェニルアジドである、請求項21に記載のコーティング剤。
- 活性剤をさらに含む、請求項21に記載のコーティング剤。
- 前記活性剤が開始剤基である、請求項31に記載のコーティング剤。
- 前記開始剤基が、有機ハロゲン化物またはベンゾフェノンを含む、請求項32に記載のコーティング剤。
- 前記活性剤が不活性化基である、請求項31に記載のコーティング剤。
- 前記不活性化基が、カルボキシレート、スルフェート、ヒドロキシ、アミン、メチル、ポリエチレングリコール、シロキシル、またはパーフルオロ基、またはこれらの任意の組合せから選択される、請求項34に記載のコーティング剤。
- 基材と、前記基材の表面に配置されたコーティングとを含む物品であって、前記コーティングが、請求項21に記載のコーティング剤を含む物品。
- 前記基材が、ケイ素、ポリオレフィン、ビニルポリマー、ポリスチレン、ポリアクリレート、ポリメタクリレート、ポリ(メチル)メタクリレート、ポリアクリロニトリル、ポリ(酢酸ビニル)、ポリ(ビニルアルコール)、塩素含有ポリマー、ポリオキシメチレン、ポリカーボネート、ポリアミド、ポリイミド、ポリウレタン、フェノール樹脂、アミノ−エポキシ樹脂、ポリエステル、セルロース系プラスチック、ゴム状プラスチック、またはこれらの任意の組合せから選択された材料から製作される、請求項36に記載の物品。
- 基材の表面を改質する方法であって:
(a)前記基材の表面と、請求項32に記載の前記コーティング剤とを接触させるステップ、
(b)前記コーティング試薬を処理して、前記コーティング試薬の潜在的反応性基を活性化することにより、コーティングされた表面を形成するステップ、
(c)前記表面と、両性イオンモノマーおよび触媒とを接触させるステップ、
(d)前記両性イオンモノマーを重合して、ブラシポリマーコーティングを形成するステップ
を含む方法。 - 前記両性イオンモノマーが、カルボキシベタイン、スルホベタイン、またはホスホベタインを含む、請求項38に記載の方法。
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US28880309P | 2009-12-21 | 2009-12-21 | |
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PCT/US2010/061602 WO2011084811A1 (en) | 2009-12-21 | 2010-12-21 | Coating agents and coated articles |
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AU (1) | AU2010339654B2 (ja) |
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Also Published As
Publication number | Publication date |
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MX2012007209A (es) | 2012-07-10 |
US10266620B2 (en) | 2019-04-23 |
CN102712825B (zh) | 2016-03-16 |
CA2781895A1 (en) | 2011-07-14 |
US9539371B2 (en) | 2017-01-10 |
EP2516567A4 (en) | 2013-12-11 |
US20150359944A1 (en) | 2015-12-17 |
AU2010339654A1 (en) | 2012-06-07 |
US20120258313A1 (en) | 2012-10-11 |
EP2516567B1 (en) | 2016-08-03 |
AU2010339654B2 (en) | 2014-07-17 |
US20170081435A1 (en) | 2017-03-23 |
EP2516567A1 (en) | 2012-10-31 |
CN102712825A (zh) | 2012-10-03 |
WO2011084811A1 (en) | 2011-07-14 |
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