JP6644215B2 - 多孔性粒子、多孔性粒子の製造方法およびブロックコポリマー - Google Patents
多孔性粒子、多孔性粒子の製造方法およびブロックコポリマー Download PDFInfo
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- JP6644215B2 JP6644215B2 JP2017534429A JP2017534429A JP6644215B2 JP 6644215 B2 JP6644215 B2 JP 6644215B2 JP 2017534429 A JP2017534429 A JP 2017534429A JP 2017534429 A JP2017534429 A JP 2017534429A JP 6644215 B2 JP6644215 B2 JP 6644215B2
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- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 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
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/28—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof by elimination of a liquid phase from a macromolecular composition or article, e.g. drying of coagulum
- C08J9/286—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof by elimination of a liquid phase from a macromolecular composition or article, e.g. drying of coagulum the liquid phase being a solvent for the monomers but not for the resulting macromolecular composition, i.e. macroporous or macroreticular polymers
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B33/00—Silicon; Compounds thereof
- C01B33/113—Silicon oxides; Hydrates thereof
- C01B33/12—Silica; Hydrates thereof, e.g. lepidoic silicic acid
- C01B33/14—Colloidal silica, e.g. dispersions, gels, sols
- C01B33/155—Preparation of hydroorganogels or organogels
-
- 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
- C08F22/00—Homopolymers and 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 one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
- C08F22/10—Esters
- C08F22/12—Esters of phenols or saturated alcohols
- C08F22/20—Esters containing oxygen in addition to the carboxy oxygen
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Description
本発明の多孔性粒子は、前述のとおり、略球形である。本発明の多孔性粒子は、例えば、長径(最も長い径)が、短径(最も短い径)に対し、例えば1.6倍以下、1.4倍以下、または1.2倍以下である。本発明の多孔性粒子は、理想的には、例えば、真球形で、長径と短径とが同じ長さである。
本発明の多孔性粒子の製造方法は、前述のとおり、モノマーおよびプレポリマーの少なくとも一方を含む多孔性粒子原料を、分散媒中に分散させて分散液を調製する分散液調製工程と、前記多孔性粒子原料を前記分散液中で重合させる重合工程と、を含み、前記重合工程において、スピノーダル分解により前記貫通孔を形成する。
本発明の製造方法では、まず、モノマーおよびプレポリマーの少なくとも一方を含む多孔性粒子原料を、分散媒中に分散させて分散液を調製する(分散液調製工程)。前記モノマーおよびプレポリマーは、特に限定されないが、例えば、前述の有機ポリマー、無機ポリマーおよび有機・無機ハイブリッドポリマーのそれぞれに対応したモノマーおよびプレポリマーが挙げられる。例えば、エポキシ樹脂の原料としては、例えば、前記各エポキシ樹脂に対応したエポキシモノマーおよびエポキシプレポリマーの少なくとも一方を用いることができる。前記エポキシモノマーおよびエポキシプレポリマーは、1種類のみ用いても2種類以上併用しても良い。前記エポキシモノマーおよびエポキシプレポリマーとしては、例えば、三菱ガス化学工業株式会社の商品名「テトラッド−C」、および日産化学株式会社の商品名「テピック」、三菱化学株式会社の商品名「エピコート828」等が挙げられる。シリカゲルの場合、原料モノマーとしては、例えば、TMOS(テトラメトキシシラン)、TEOS(テトラエトキシシラン)、MTMS(メトキシシラン)、SQ(シルセスキオキサン)等が挙げられる。また、有機・無機ハイブリッド系の原料モノマーとしては、例えば、メチルトリメトキシシラン、ビニルトリメトキシシラン、ジメチルジメトキシシラン、1,2−ビストリメトキシシリルエタン等のオルガノアルコキシシラン、および、シランカップリング剤の反応部を含む有機高分子化合物とシリカの組合せも挙げられ、これらは、例えば、ハイブリッドシリカの原料モノマーとして用いることができる。
X−(NY2)m (A)
以下において、前記ブロックコポリマー(分散剤)および前記分散剤製造工程について詳しく説明する。
(1)重金属化合物を使用しない;ATRP法やDT法のような重金属化合物を使用しない。
(2)精製が必須ではない;ATRP法やDT法は重金属、RAFT法やMADIX法は硫黄化合物の除去が必要である。
(3)特殊で高価な化合物を必要とせず、市場にある比較的安価な材料が使用でき、よって低コストである;他のリビングラジカル重合方法では特別な化合物が必要である。
(4)重合条件が温和で、従来のラジカル重合方法と同様の条件で重合を行うことができる;NMP法では高温が必要であり、ATRP法では酸素の除去が必要である。
(5)使用するモノマーや溶媒なども精製する必要がなく、様々なモノマーが使用でき、酸基、アミノ基などの様々な官能基を有するモノマーを使用することが可能で、ポリマーブロックに様々な官能基を導入することができる;特にATRP法では酸基がその触媒毒となり、酸基をそのまま使用することはできない。NMP法ではメタクリレートはうまく重合しない。
(6)分子量と構造が制御でき、所望の結合状態のブロックポリマーが容易に得られ、かつ重合率も非常によい。
[開始化合物1モル×モノマー分子量×モノマー対開始化合物モル比]
で算出することができる。
本発明の多孔性粒子の製造方法は、具体的には、例えば、以下のようにして行うことができる。なお、以下においては、主に、熱硬化性のモノマーおよびプレポリマーの少なくとも一方を含む前記多孔性粒子原料を用いた製造方法について説明する。また、前記熱硬化性のモノマーおよびプレポリマーの中でも、特に、エポキシモノマーおよびエポキシプレポリマーの少なくとも一方を含む前記多孔性粒子原料について説明する。ただし、前記多孔性粒子原料は、前述のとおり、特に限定されず任意である。
以下の合成例1〜2のようにして、疎水性ポリマーブロックAおよび親水性ポリマーブロックBから形成されたA−Bブロックコポリマー(分散剤)を製造(合成)した。これらのブロックコポリマーは、構成するモノマーがすべて(メタ)アクリレート系モノマーで、A鎖のポリマーブロックが、疎水性基を有する(メタ)アクリレートであり、B鎖のポリマーブロックが親水性基を有する(メタ)アクリレートを構成成分とする。また、GPCにおけるポリスチレン換算の数平均分子量が2,000〜100,000であり、そのPDIが1.6以下であり、疎水性基を有する(メタ)アクリレートからなるAのポリマーブロックの数平均分子量が80,000未満かつ全体の構成成分の20〜95質量%である。なお、以下において、各物質の部数は、特に断らない限り、質量部(重量部)である。
撹拌機、還流コンデンサー、温度計および窒素導入管を取り付けた反応容器に、トルエン5.23部、ラウリルメタクリレート(以下、LMAと略記)5部、ヨウ素0.0495部、重合開始剤として2,2’−アゾビス(4−メトキシ−2,4−ジメチルバレロニトリル)(以下、V−70と略記)0.909部、アゾビスジメチルイソバレロニトリル(以下、V−65と略記)0.0183部、およびテトラブチルアンモニウムヨージド(以下、BNIと略す)0.0726部を仕込んで、窒素を流しながら60℃で撹拌した。16時間重合して、ポリマーブロックAを得た。これをサンプリングして、固形分を測定し、不揮発分から換算した重合転化率は90%であった。この時のGPCの示差屈折計での数平均分子量(以下、RI−Mnと略記)は16,500であり、PDIは1.27であった。
撹拌機、還流コンデンサー、温度計および窒素導入管を取り付けた反応装置に、ジメチルジグリコール(以下、DMDGと略す)33.4部、LMA100部、ヨウ素1.5部、テトラブチルアンモニウムヨージド(以下、BNIと略す)0.7部、重合開始剤として2,2’−アゾビス(4−メトキシ−2,4−ジメチルバレロニトリル)(商品名:V−70、和光純薬社製)3.8部、2,2’−アゾビス(2,4−ジメチルバレロニトリル)(商品名:V−65、和光純薬社製)1.0部を添加した。そして、アルゴンガスを導入しながら撹拌し、マントルヒーターにて60℃に昇温した。反応系をそのまま60℃に保ち、3時間重合してポリマーブロックAを得た。重合の進行を、反応系中の1H−NMR測定により算出したところ、重合率は89%であった。また、THF溶媒によるゲルパーミエーションクロマトグラフィー(GPC)測定(検出器:示唆屈折率計)により分子量を算出し、数平均分子量(以下、Mnと略す)が5900、重量平均分子量(以下、Mwと略す)で8200であった。その分子量分布(以下、PDI値と略す)は1.40であった。
<エポキシモノマー組成物の調製>
エポキシモノマーとして、エポキシ当量が95〜110(平均102)である下記式(1)で表されるエポキシ化合物(商品名「テトラッド−C」、三菱ガス化学工業株式会社)2.00重量部、硬化剤として、アミン価が520〜550である下記式(2)で表されるビス(4−アミノシクロヘキシル)メタン(東京化成工業株式会社製)1.15重量部、ポロゲンとして、平均分子量が200である下記式(3)で表されるポリエチレングリコール200(和光純薬工業株式会社製)8重量部を用い、これらを、自転・公転ミキサーの「あわとり練太郎」(株式会社シンキーの商品名)で5分間混合することで、エポキシモノマー組成物を得た。
円筒状のガラス製サンプル瓶(内径19mm、高さ60mmの)に上記で得られたエポキシモノマー組成物11.15gを、分散媒としてドデカン10gに上記の前記ブロックコポリマー(分散剤)K−1を0.6g溶解したものの中に加え、分散液を調製した。
前記分散液を、撹拌翼で常温で毎分2000回転で30分間撹拌して乳化分散させた後、毎分回転数を、粒子が沈降および相互付着しない程度の回転数である50回転に下げて高温浴槽中温度140℃で60分間重合した。重合して得られたものをMEKに入れ十分撹拌した後遠心分離機を用いて粒子を分離した。このMEKによる洗浄工程を10回繰り返してポロゲンや残存モノマー等を十分に除去した後、減圧乾燥してエポキシ樹脂からなる球形の多孔性粒子を2.85g得た。前記多孔性粒子の平均粒径は、28μmであった。また、前記球形の多孔性粒子(球形微粒子)の外観と粒子表面および粒子内部のSEM写真を図1〜4に示した。図1は、実施例1で製造したエポキシ樹脂製多孔性粒子の外観写真(倍率250倍)である。図2は、実施例1で製造したエポキシ樹脂製多孔性粒子の外観写真(倍率1000倍)である。図3は、実施例1で製造したエポキシ樹脂製多孔性粒子の外観写真(倍率5000倍)である。図4は、実施例1で製造したエポキシ樹脂製多孔性粒子の断面の拡大写真(倍率10000倍)である。図1〜4に示すとおり、このエポキシ樹脂製多孔性粒子は、その内部に、多孔構造が連通している貫通孔を有していた。また、このエポキシ樹脂製多孔性粒子の表面にはスキン層が無く、前記貫通孔の端部が、前記多孔性粒子の外部に向かって開口していた。
前記重合工程における反応温度を150℃とする以外は実施例1と同様にしてエポキシ樹脂からなる球形の多孔性粒子を2.75g得た。前記多孔性粒子の平均粒径は、30μmであった。また、前記球形の多孔性粒子(球形微粒子)の外観と粒子表面および粒子内部のSEM写真は、図1〜4(実施例1)と同様の結果を示していた。すなわち、このエポキシ樹脂製多孔性粒子は、その内部に、多孔構造が連通している貫通孔を有していた。また、このエポキシ樹脂製多孔性粒子の表面にはスキン層が無く、前記貫通孔の端部が、前記多孔性粒子の外部に向かって開口していた。
分散剤として、ブロックコポリマーK−1に代えてブロックコポリマーK−2を用いる以外は実施例1と同様にしてエポキシ樹脂からなる球形の多孔性粒子を2.5g得た。前記多孔性粒子の平均粒径は、33μmであった。また、前記球形の多孔性粒子(球形微粒子)の外観と粒子表面および粒子内部のSEM写真は、図1〜4(実施例1)と同様の結果を示していた。すなわち、このエポキシ樹脂製多孔性粒子は、その内部に、多孔構造が連通している貫通孔を有していた。また、このエポキシ樹脂製多孔性粒子の表面にはスキン層が無く、前記貫通孔の端部が、前記多孔性粒子の外部に向かって開口していた。
<エポキシモノマー組成物の調製>
エポキシモノマーとして、エポキシ当量が99である下記式(4)で表されるエポキシ化合物「イソシアヌル酸トリグリシジル」(商品名「テピック−S」、日産化学工業株式会社)1.6重量部、硬化剤として、アミン価が520〜550である前記式(2)で表されるビス(4−アミノシクロヘキシル)メタン(東京化成工業株式会社製)0.37重量部、ポロゲンとして、平均分子量が200である前記式(3)で表されるポリエチレングリコール200(和光純薬工業株式会社製)7重量部を用い、「テピック−S」とPEG200を110℃に加熱溶融し、別途85℃で加熱溶融した硬化剤とを合わせてボルテックスミキサー3000rpmで数分間混合してエポキシモノマー組成物を得た。
円筒状のガラス製サンプル瓶(内径19mm、高さ60mmの)に上記で得られたエポキシモノマー組成物8.97gを、分散媒としてドデカン10gに上記の前記ブロックコポリマー(分散剤)K−1を0.6g溶解したものの中に加えボルテックスミキサーで外見上の乳化状態が安定するまで撹拌(6〜10分)して分散液を調製した。なお、分散媒は、分散液調製に先立ち、予め50℃以上に加温した。
前記分散液を、撹拌翼で毎分回転数を50回転として高温浴槽中温度90℃で180分間重合した。重合して得られたものをテトラヒドロフランに入れ十分撹拌した後遠心分離機を用いて粒子を分離した。このテトラヒドロフランによる洗浄工程を10回繰り返してポロゲンや残存モノマー等を十分に除去した後、減圧乾燥してエポキシ樹脂からなる球形の多孔性粒子を1.75g得た。前記多孔性粒子の平均粒径は、29μmであった。また、前記球形の多孔性粒子(球形微粒子)の外観と粒子表面および粒子内部のSEM写真は、図1〜4(実施例1)と同様の結果を示していた。すなわち、このエポキシ樹脂製多孔性粒子は、その内部に、多孔構造が連通している貫通孔を有していた。また、このエポキシ樹脂製多孔性粒子の表面にはスキン層が無く、前記貫通孔の端部が、前記多孔性粒子の外部に向かって開口していた。
重合温度を80℃とした以外は実施例4と同じ条件で多孔性粒子を製造し、球形の多孔性粒子を1.83g得た。前記多孔性粒子の平均粒径は、26μmであった。また、前記球形の多孔性粒子(球形微粒子)の外観と粒子表面および粒子内部のSEM写真は、図1〜4(実施例1)と同様の結果を示していた。すなわち、このエポキシ樹脂製多孔性粒子は、その内部に、多孔構造が連通している貫通孔を有していた。また、このエポキシ樹脂製多孔性粒子の表面にはスキン層が無く、前記貫通孔の端部が、前記多孔性粒子の外部に向かって開口していた。
PEG200を8.4部、分散剤を0.67部、分散媒を9部として重合した以外は実施例4と同じ条件で多孔性粒子を製造し、球形の多孔性粒子を1.85g得た。前記多孔性粒子の平均粒径は、38μmであった。また、前記球形の多孔性粒子(球形微粒子)の外観と粒子表面および粒子内部のSEM写真は、図1〜4(実施例1)と同様の結果を示していた。すなわち、このエポキシ樹脂製多孔性粒子は、その内部に、多孔構造が連通している貫通孔を有していた。また、このエポキシ樹脂製多孔性粒子の表面にはスキン層が無く、前記貫通孔の端部が、前記多孔性粒子の外部に向かって開口していた。
<アクリルモノマー組成物の調製>
相分離誘起成分として、ポリエチレンオキシド(アルドリッチ製、平均分子量10万)0.41gと、溶媒として、ジメチルホルムアミド(ナカライテスク(株)製)10gをスクリュー管瓶中で60℃において均一に溶解させ、溶液を得た。室温まで冷ました後、モノマーとして、グリセロールジメタクリレート(GDMA、共栄社化学製、GP−101P、分子量227)3.35gを溶液に添加して、攪拌により均一な溶液を調製した。さらに、開始剤および可逆移動触媒として、2,2'−アゾビス(2,4−ジメチルバレロニトリル)(和光純薬工業(株)製)0.04g、ヨウ素(東京化成工業(株)製)0.02g、N−ヨードこはく酸イミド(東京化成工業(株)製)0.002gを溶液に添加して、攪拌により均一な溶液を調製した。次に、この重合溶液を超音波装置により溶液内の泡を取り除いた後、窒素ガスによりバブリングで残存酸素を置換した。
円筒状のガラス製サンプル瓶(内径19mm、高さ60mmの)に上記で得られたアクリルモノマー組成物13.80gを、分散媒としてドデカン5gに上記の前記ブロックコポリマー(分散剤)K−1を0.30g溶解したものの中に加え、ボルテックスミキサー3000rpmで外見上の乳化状態が安定するまで撹拌(6〜10分)して分散液を調製した。
前記分散液を、撹拌翼で毎分回転数を50回転として高温浴槽中温度100℃で8時間重合反応を行った。その後、得られた高分子重合体を室温まで冷却して容器から取り出し、アセトンおよびメタノールで洗浄し、減圧乾燥してアクリル樹脂からなる球形の多孔性粒子を2.1g得た。前記多孔性粒子の平均粒径は、25μmであった。この多孔体を、走査型電子顕微鏡で外観および内部断面の構造の確認を行った結果、図5および6に示すような0.1μm程度の孔を有する共連続構造を形成していた。
<シリカモノマー組成物の調製>
50mlのビーカーにポロゲンとしてのポリエチレンオキサイド(略称;PEO、重量平均分子量1万)1.12gと0.01M酢酸10mLを入れてスターラーチップで溶解させた。溶解した後氷水で冷やして撹拌しながらテトラメトキシシラン(略称;TMOS)4.5mlを入れて透明な均一溶液になるまで撹拌し(15分程度)、透明になったことを確認した(加水分解完了)。
前記実施例1で使用したサンプル瓶と同じものに、分散媒としてドデカン15gに前記A−Bブロックコポリマー(分散剤)K−1を0.9g溶解したものの中に前記シリカ混合物を加え、分散液を調製した。
前記分散液を、撹拌翼で常温で毎分2000回転で10分間撹拌後、毎分回転数を50回転に下げて高温浴槽中温度40℃で90分間反応させることにより、重合を行った。これにより、微粒子状に分散状態となっているシリカ組成物が粒子の状態で固化した。この重合工程により得られたものをMEKに入れ十分撹拌した後、遠心分離機を用いて粒子を分離した。このMEKによる洗浄工程を10回繰り返してポロゲンや残存モノマー等を十分に除去した後、減圧乾燥してシリカゲルからなる球形の多孔性粒子を2.6g得た。前記多孔性粒子の平均粒径は、12μmであった。また、前記球形の多孔性粒子(球形微粒子)の外観と粒子表面のSEM写真を図7〜10に示した。図7〜10は、本実施例の粒子表面の写真をそれぞれ示す。また、各図は、それぞれ、倍率が100倍、1000倍、5000倍および10000倍の写真をである。図7〜10の各図に示すとおり、このシリカゲル製多孔性粒子は、その内部に、多孔構造が連通している貫通孔を有し、かつ、表面にスキン層が無く、前記貫通孔の端部が、前記多孔性粒子の外部に向かって開口していた。
分散剤として、ブロックコポリマーK−1に代えてブロックコポリマーK−2を用いる以外は実施例8と同様にしてシリカゲルからなる球形の多孔性粒子を2.6g得た。前記多孔性粒子の平均粒径は、11μmであった。また、前記球形の多孔性粒子(球形微粒子)の外観と粒子表面および粒子内部のSEM写真は、図1〜4(実施例1)と同様の結果を示していた。すなわち、このシリカゲル製多孔性粒子は、その内部に、多孔構造が連通している貫通孔を有していた。また、このシリカゲル製多孔性粒子の表面にはスキン層が無く、前記貫通孔の端部が、前記多孔性粒子の外部に向かって開口していた。
分散剤として、ブロックコポリマーK−1に代えてノニオン性界面活性剤「ユニルーブ10MS−250KB」(日油株式会社の商品名)を用いる以外は実施例8と同様にしてシリカゲルからなる球形の多孔性粒子を3.3g得た。前記多孔性粒子の平均粒径は、12μmであった。また、前記球形の多孔性粒子(球形微粒子)の外観と粒子表面および粒子内部のSEM写真は、図1〜4(実施例1)と同様の結果を示していた。すなわち、このシリカゲル製多孔性粒子は、その内部に、多孔構造が連通している貫通孔を有していた。また、このシリカゲル製多孔性粒子の表面にはスキン層が無く、前記貫通孔の端部が、前記多孔性粒子の外部に向かって開口していた。
Claims (6)
- 略球状の多孔性粒子であって、
前記多孔性粒子は、有機ポリマーおよびシリカゲルの少なくとも一方により形成され、その内部に、多孔構造が連通している共連続構造の貫通孔を有し、
前記貫通孔の端部が、前記多孔性粒子の外部に向かって開口していることを特徴とする多孔性粒子。 - 前記貫通孔が、スピノーダル分解により形成された貫通孔である請求項1記載の多孔性粒子。
- 長径が短径の1.6倍以下である請求項1または2記載の多孔性粒子。
- 平均粒径が0.5〜30,000μmの範囲である請求項1から3のいずれか一項に記載の多孔性粒子。
- モノマーおよびプレポリマーの少なくとも一方とポロゲンとを含む多孔性粒子原料を、分散媒中に分散させて分散液を調製する分散液調製工程と、
前記多孔性粒子原料を前記分散液中で重合させる重合工程と、を含み、
前記分散液調製工程において、前記多孔性粒子原料を、分散剤とともに分散媒中に分散させ、
前記分散剤が、疎水性ポリマーブロックおよび親水性ポリマーブロックを含んで形成されたブロックコポリマーであり、
前記重合工程において、スピノーダル分解により前記貫通孔を形成する請求項1から4のいずれか一項に記載の多孔性粒子の製造方法。 - さらに、前記分散剤を製造する分散剤製造工程を含み、
前記分散剤製造工程が、リビングラジカル重合により前記疎水性ポリマーブロックおよび親水性ポリマーブロックの一方を形成する第1のリビングラジカル重合工程と、
前記第1のリビングラジカル重合工程後に、リビングラジカル重合により前記疎水性ポリマーブロックおよび親水性ポリマーブロックの他方を形成する第2のリビングラジカル重合工程と、を含む
請求項5記載の製造方法。
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2016
- 2016-08-05 WO PCT/JP2016/073209 patent/WO2017026424A1/ja active Application Filing
- 2016-08-05 JP JP2017534429A patent/JP6644215B2/ja active Active
- 2016-08-05 US US15/751,718 patent/US20180223067A1/en not_active Abandoned
- 2016-08-05 EP EP16835121.1A patent/EP3327070A4/en not_active Withdrawn
- 2016-08-09 TW TW105125294A patent/TW201718666A/zh unknown
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Publication number | Publication date |
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EP3327070A4 (en) | 2019-06-26 |
EP3327070A1 (en) | 2018-05-30 |
JPWO2017026424A1 (ja) | 2018-06-14 |
WO2017026424A1 (ja) | 2017-02-16 |
US20180223067A1 (en) | 2018-08-09 |
TW201718666A (zh) | 2017-06-01 |
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