JP7299595B2 - 微粒子用の湿式コーティング剤 - Google Patents
微粒子用の湿式コーティング剤 Download PDFInfo
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- JP7299595B2 JP7299595B2 JP2021524857A JP2021524857A JP7299595B2 JP 7299595 B2 JP7299595 B2 JP 7299595B2 JP 2021524857 A JP2021524857 A JP 2021524857A JP 2021524857 A JP2021524857 A JP 2021524857A JP 7299595 B2 JP7299595 B2 JP 7299595B2
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- meth
- acrylate
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- 238000009826 distribution Methods 0.000 claims description 12
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- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical group COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 11
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- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
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- 229960001783 nicardipine Drugs 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
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- DPJRMOMPQZCRJU-UHFFFAOYSA-M thiamine hydrochloride Chemical compound Cl.[Cl-].CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N DPJRMOMPQZCRJU-UHFFFAOYSA-M 0.000 description 1
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 229940113165 trimethylolpropane Drugs 0.000 description 1
- XPFJYKARVSSRHE-UHFFFAOYSA-K trisodium;2-hydroxypropane-1,2,3-tricarboxylate;2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound [Na+].[Na+].[Na+].OC(=O)CC(O)(C(O)=O)CC(O)=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O XPFJYKARVSSRHE-UHFFFAOYSA-K 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
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- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
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Description
本願は、2019年6月7日に、日本に出願された特願2019-106702号に基づき優先権を主張し、その内容をここに援用する。
非特許文献1および非特許文献2は、高分子のナノ粒子水系分散剤でコーティングすることを開示している。ナノ粒子として、12:6:4 Poly(アクリル酸エチル(EA)/メタクリル酸メチル(MMA)/メタクリル酸2- ヒドロキシエチル(HEMA))からなるコアと、6:12:8 Poly(EA/MMA/HEMA)からなるシェルとを有するコアシェル型ナノ粒子を含むラテックスを開示している。
〔1〕 (メタ)アクリレート系共重合体からなり、且つ体積基準粒子径分布における50%径が10nm以上150nm以下である粒子を含むラテックスからなる、微粒子用の湿式コーティング剤。
〔2〕 (メタ)アクリレート系共重合体が、アクリル酸エチルに由来する単量体単位、メタクリル酸メチルに由来する単量体単位、およびメタクリル酸2-ヒドロキシエチルに由来する単量体単位を含有してなるものである、〔1〕に記載の微粒子用の湿式コーティング剤。
〔3〕 体積基準粒子径分布における50%径が10nm以上40nm未満である、〔1〕または〔2〕に記載の微粒子用の湿式コーティング剤。
〔4〕 微粒子が核粒子である、〔1〕~〔3〕のいずれか一項に記載の微粒子用の湿式コーティング剤。
ラテックスを製造するに際し、乳化重合反応の系内に、追加の単量体を更に添加してもよい。例えば、単量体の一部を一括して予め乳化重合系内に仕込み重合した後、残りの単量体を連続的又は間欠的に添加して重合する方法等が挙げられる。最初に仕込む単量体の組成と、追加で添加する単量体の組成を異なるものとすることによって、コアシェル構造の共重合体粒子を得ることもできる。また、単量体を最初から連続的又は間欠的に添加する方法であってもよい。単量体を添加する工程において、単量体の組成が連続的に変化するような、いわゆるパワーフィード法を用いることも可能である。
(メタ)アクリレート系共重合体の総質量に対する、アクリル酸エチルに由来する単量体単位の量は、好ましくは26~39質量%、より好ましくは30~35質量%であり、メタクリル酸メチルに由来する単量体単位の量は、好ましくは39~52質量%、より好ましくは43~48質量%であり、メタクリル酸2-ヒドロキシエチルに由来する単量体単位の量は、好ましくは9~35質量%、より好ましくは17~27質量%である。アクリル酸エチルに由来する単量体単位、メタクリル酸メチルに由来する単量体単位、およびメタクリル酸2-ヒドロキシエチルに由来する単量体単位の合計が、(メタ)アクリレート系共重合体の総質量に対して、99%質量%以上であることが好ましく、100質量%であることがより好ましい。
また、重合開始剤は、好ましくは、単量体と乳化剤を含む混合液に、攪拌下、1~5時間程度かけて添加することが好ましい。
また、重合反応終了後、透析等の精製処理を実施することができる。
キレート化剤としては、例えば、エチレンジアミン四酢酸ナトリウム等が挙げられる。
連載移動剤として、例えば、n-ブチルメルカプタン、tert-ブチルメルカプタン、tert-ドデシルメルカプタン、n-オクチルメルカプタン、n-ラウリルメルカプタン等のメルカプタン系化合物、α-メチルスチレンダイマー等の核置換α-メチルスチレンの二量体;テトラメチルチウラジウムジスルフィド、テトラエチルチウラジウムジスルフィド等のジスルフィド類;四塩化炭素、四臭化炭素等のハロゲン化誘導体;2-エチルヘキシルチオグリコレート等が挙げられる。これらの中でもメルカプタン類が好ましい。これらは1種単独で用いてもよいし、2種以上を併用してもよい。
該核粒子は、速放性製剤および放出持続型製剤(徐放性製剤)などの放出制御型製剤であってもよい。核粒子は、慣用の添加剤を含有していてもよい。該添加剤としては、例えば、賦形剤、崩壊剤、結合剤、滑沢剤、着色剤、pH調整剤、pH緩衝剤、界面活性剤、徐放化剤、安定化剤、酸味料、香料、流動化剤、清涼化剤、甘味料、旨み成分、甘味増強剤などが挙げられる。これら添加剤は、製剤分野において慣用の量が用いられる。
医薬や農薬の有効成分である上記化合物のうち、塩形成部位を有する化合物では、その生理的又は薬学的に許容可能な塩(特に、医薬的または農薬的に許容可能な塩など)なども含まれる。
滑沢剤としては、例えば、ステアリン酸マグネシウム、ステアリン酸カルシウム、タルク、蔗糖脂肪酸エステル、フマル酸ステアリルナトリウムなどが挙げられる。
pH調整剤としては、クエン酸塩、リン酸塩、炭酸塩、酒石酸塩、フマル酸塩、酢酸塩、アミノ酸塩などが挙げられる。
pH緩衝剤としては、クエン酸-クエン酸ナトリウム緩衝剤などが挙げられる。
界面活性剤として、ラウリル硫酸ナトリウム、ポリソルベート、ポリオキシエチレンポリオキシプロピレングリコールなどが挙げられる。
安定化剤としては、例えば、トコフェロール、エデト酸四ナトリウム、ニコチン酸アミド、シクロデキストリン類などが挙げられる。
香料としては、例えば、メントール、ハッカ油、レモン油、バニリンなどが挙げられる。
流動化剤としては、例えば、軽質無水ケイ酸、含水二酸化ケイ素などが挙げられる。
清涼化剤としては、カンフル及びボルネオールなどのテルペン系化合物(モノテルペンアルコールなど)などの他、この前記テルペン系化合物を含む精油、エッセンス又はパウダー;ペパーミント、スペアミント、クールミントなどの精油、エッセンス又は粉末(パウダー);前記の精油又はエッセンスを粉末状担体(例えば、デキストリンなど)に吸着させたもの、精油又はエッセンスを賦形材(アラビアガムなど)及び液体基剤(水、アルコールなど)と混合し、粉粒化したものなどが挙げられる。
旨み成分としては、アミノ酸系旨み成分(アミノ酸又はその塩、例えば、グルタミン酸、グルタミン酸ナトリウム、グルタミン酸カリウム、グルタミン酸塩酸塩、グアニル酸ナトリウム、イノシン酸、イノシン酸ナトリウム、アルギニン-グルタミン酸塩、アスパラギン酸、アスパラギン酸ナトリウム、グリシン、アラニンなど)、ペプチド系旨み成分(L-グルタミル-L-グルタミン酸、L-グルタミル-L-セリンなどのジペプチド;トリ-L-グルタミン酸、L-グルタミル-L-グリシル-L-セリンなどのトリペプチドなど)、カルボン酸系旨み成分(コハク酸ナトリウムなどのカルボン酸塩など)などが挙げられる。
さらに鹹味(塩味)を有する甘味増強剤(又は鹹味剤)を含有してもよい。このような甘味増強剤としては、塩化ナトリウム、塩化カリウム、リン酸塩(リン酸水素カリウム、リン酸水素ナトリウムなど)などが例示できる。甘味増強剤(又は鹹味剤)は中性塩、例えば、ナトリウムイオン及び/又は塩素イオン(塩化物イオン)として解離する塩である場合が多い。
蒸留水300gにドデシルスルホン酸ナトリウム1.38gを溶解させた。これにアクリル酸エチル27.3モル%、メタクリル酸メチル54.5モル%およびメタクリル酸2-ヒドロキシエチル18.2モル%からなる単量体34.6gを加え、ホモミキサー(4C,特殊機化工業(株))を使用して5分間攪拌して、乳化させた。これを500mL容量のガラス製四頸フラスコに移した。
窒素ガス流通下、80℃にて攪拌しながら、4w/v%の過硫酸アンモニウム0.5mLを上記フラスコに15分間おきに合計4mlを滴下して、最初の過硫酸アンモニウムの滴下から2時間重合反応をさせた。
得られたラテックスをセルロースチューブ(UC17/8,三光純薬(株))を用いて精製水中で透析した。半日毎に新鮮な精製水に入れ替えて,合計5日間の洗浄操作を行った。その後、ラテックスの粒子径分布を動的光散乱式粒子径分布測定装置(LB500,HORIBA)にて測定した。体積基準粒子径分布における50%径は28.6nm、共重合体のガラス転移温度Tgは61.8℃であった。なお、ガラス転移温度は、示差操作熱量計(DSC50,島津製作所)により測定した。測定条件は,サンプル皿:アルミニウムパン;試料仕込み量:5mg,昇温速度:20℃/minとした。TgはDSCサーモグラムにおけるガラス転移前の基線の直線部分と転移領域の変曲点の接線とを外挿して得られる交点の温度として定義した。
得られた80%コーティング粒子をふるい分けし、核粒子同士が結合し凝集した割合い(凝集率)を算出した。算出された凝集率は最大で0.62%であった。
ドデシルスルホン酸ナトリウムの量を0.02gに変えた以外は、実施例1と同じ方法で、ラテックスを得た。体積基準粒子径分布における50%径は221.1nm、共重合体のガラス転移温度Tgは63.2℃であった。
得られた80%コーティング粒子の凝集率を算出した。算出された凝集率は、最大で2.37%であった。
アクリル酸エチル27.3モル%、メタクリル酸メチル54.5モル%およびメタクリル酸2-ヒドロキシエチル18.2モル%からなる単量体を、アクリル酸エチル40.9モル%、メタクリル酸メチル40.9モル%およびメタクリル酸2-ヒドロキシエチル18.2モル%からなる単量体に変えた以外は、実施例1と同じ方法で、ラテックスを得た。体積基準粒子径分布における50%径は34.6nm、共重合体のガラス転移温度Tgは44.3℃であった。
結果、各コーティング粒子は徐放性に優れたものであることが確認された。
ドデシルスルホン酸ナトリウムの量を0.02gに変えた以外は、実施例2と同じ方法で、ラテックスを得た。体積基準粒子径分布における50%径は220.1nm、共重合体のガラス転移温度Tgは45.8℃であった。
結果、比較例2で調製された各コーティング粒子は、実施例2で調製された各コーティング粒子に比べて、徐放性に劣るものであることが確認された。
Claims (2)
- (メタ)アクリレート系共重合体からなり、且つ体積基準粒子径分布における50%径が10nm以上40nm未満である粒子を含むラテックスからなる、
微粒子用の湿式コーティング剤において、
(メタ)アクリレート系共重合体が、アクリル酸エチルに由来する単量体単位、メタクリル酸メチルに由来する単量体単位、およびメタクリル酸2-ヒドロキシエチルに由来する単量体単位からなるものである、微粒子用の湿式コーティング剤。 - 微粒子が核粒子である、請求項1に記載の微粒子用の湿式コーティング剤。
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