JP2018535829A - ダブルエマルジョンによってマイクロカプセルを作製するための方法 - Google Patents
ダブルエマルジョンによってマイクロカプセルを作製するための方法 Download PDFInfo
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- JP2018535829A JP2018535829A JP2018534010A JP2018534010A JP2018535829A JP 2018535829 A JP2018535829 A JP 2018535829A JP 2018534010 A JP2018534010 A JP 2018534010A JP 2018534010 A JP2018534010 A JP 2018534010A JP 2018535829 A JP2018535829 A JP 2018535829A
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- 239000004324 sodium propionate Substances 0.000 description 1
- 235000010334 sodium propionate Nutrition 0.000 description 1
- 229960003212 sodium propionate Drugs 0.000 description 1
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- 229960001471 sodium selenite Drugs 0.000 description 1
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- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 235000019794 sodium silicate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 229960002920 sorbitol Drugs 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229940032147 starch Drugs 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000011232 storage material Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
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- 239000000516 sunscreening agent Substances 0.000 description 1
- RJKCKKDSSSRYCB-UHFFFAOYSA-N tebutam Chemical compound CC(C)(C)C(=O)N(C(C)C)CC1=CC=CC=C1 RJKCKKDSSSRYCB-UHFFFAOYSA-N 0.000 description 1
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- RBTVSNLYYIMMKS-UHFFFAOYSA-N tert-butyl 3-aminoazetidine-1-carboxylate;hydrochloride Chemical compound Cl.CC(C)(C)OC(=O)N1CC(N)C1 RBTVSNLYYIMMKS-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- OPASCBHCTNRLRM-UHFFFAOYSA-N thiometon Chemical compound CCSCCSP(=S)(OC)OC OPASCBHCTNRLRM-UHFFFAOYSA-N 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 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
- 235000013337 tricalcium citrate Nutrition 0.000 description 1
- 229960003500 triclosan Drugs 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
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 229960004441 tyrosine Drugs 0.000 description 1
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- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
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- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 235000019156 vitamin B Nutrition 0.000 description 1
- 239000011720 vitamin B Substances 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 235000019166 vitamin D Nutrition 0.000 description 1
- 239000011710 vitamin D Substances 0.000 description 1
- 150000003710 vitamin D derivatives Chemical class 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
- 229940046008 vitamin d Drugs 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
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- 239000004246 zinc acetate Substances 0.000 description 1
- 235000013904 zinc acetate Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
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Abstract
Description
a)少なくとも1種類の活性物質を含む組成物C1を、架橋性液体組成物C2に撹拌下で添加して、組成物C2中に分散された組成物C1の液滴を含む第一のエマルジョンを得る工程であって、
前記活性物質は、潤滑剤、燃料、若しくはビチューメン産業に、又は掘削汚泥若しくは泥水に用いられる添加剤でも、又は石油探査/採油に用いられる添加剤でもなく、組成物C1及び組成物C2は互いに不混和性である、工程、
b)工程a)で得られた前記第一のエマルジョンを、液体組成物C3に撹拌下で添加して、組成物C3中に分散された液滴を含む第二のエマルジョンを得る工程であって、組成物C3及び組成物C2は互いに不混和性である、工程、
c)工程b)で得られた前記第二のエマルジョンを、1000s−1〜100000s−1の均一な制御されたせん断速度を前記第二のエマルジョンに適用するミキサーに充填して、組成物C3中に分散された液滴を含む第三のエマルジョンを得る工程、及び、
d)工程c)で得られた前記液滴を架橋して、組成物C3中に分散された固体マイクロカプセルを得る工程、
を含む、固体マイクロカプセルを製造するための方法である。
工程a)の過程では、組成物C1が、架橋性液体組成物C2に添加され、前記添加は、撹拌下で行われるが、このことは、組成物C1と組成物C2との混合物を乳化する目的で組成物C1が添加される間、前記組成物C2が典型的には機械的に撹拌されることを意味する。
−エラストマー配合物、ゴム配合物、塗料配合物、コーティング配合物、接着剤配合物、又はシーラント配合物の重合のための架橋剤、硬化剤、有機触媒、及び金属系触媒(例えば、白金、パラジウム、チタン、モリブデン、銅、又は亜鉛の有機複合体及び無機複合体);
−インク、パーソナルケア製品、エラストマー配合物、ゴム配合物、塗料配合物、コーティング配合物、接着剤配合物、シーラント配合物、又は紙配合物のための染料、着色剤、顔料;
−洗剤、家庭掃除用製品、パーソナルケア製品、テキスタイル(いわゆるスマートテキスタイル)、コーティング配合物のための香料。本発明にとって有用である香料は、国際香粧品香料協会(IFRA)によって公開され、更新されている標準のリストに属する化合物のいずれかである;
−飼料及び食品のための芳香剤、香味剤、ビタミン、アミノ酸、タンパク質、必須脂質、プロバイオティックス、抗酸化剤、保存剤;
−洗剤及びパーソナルケア製品のための布地用柔軟剤及びコンディショナー。
本発明にとって有用である化合物としては、限定されないが、米国特許第6335315号及び米国特許第5877145号の特許文献に列挙されている化合物が挙げられる;
−パーソナルケア製品、テキスタイル(いわゆるスマートテキスタイル)のための酵素、ビタミン、タンパク質、植物抽出物、保湿剤、消毒剤、殺菌剤、日焼け止め剤、薬物などの生物活性化合物。これらの化合物としては、限定されないが、ビタミンA、ビタミンB、ビタミンC、ビタミンD、ビタミンE、パラアミノ安息香酸、アルファヒドロキシ酸、カンファー、セラミド、エラグ酸、グリセリン、グリシン、グリコール酸、ヒアルロン酸、ヒドロキノン、イソプロピル、イソステアレート、パルミチン酸イソプロピル、オキシベンゾン、パンテノール、プロリン、レチノール、パルミチン酸レチニル、サリチル酸、ソルビン酸、ソルビトール、トリクロサン、チロシンが挙げられる;並びに
−農業用化学薬品のための肥料、除草剤、殺虫剤、駆除剤、殺真菌剤、忌避剤、及び消毒剤。
O,O−ジエチルO−2−イソプロピル−6−メチルピリミジン−4−イルホスホロチオエート、
O,O−ジエチルS−2−エチルチオエチルホスホロジチオエート、
S−クロロメチルO,O−ジエチルホスホロジチオエート、
O−エチルS,S−ジプロピルホスホロジチオエート、
O,O−ジエチルS−エチルチオメチルホスホロジチオエート、
S−tert‐ブチルチオメチルO,O−ジエチルホスホロジチオエート(S-tertiobutylthiomethyl O,O-diethyl phosphorodithioate)、
O,O−ジエチル−O−4−メチルスルフィニルフェニルホスホロチオエート、
O−(4−ブロモ−2−クロロフェニル)O−エチル−S−プロピルホスホロジチオエート、
S−1,2−ジ(エトキシカルボニル)エチルO,O−ジメチルホスホロジチオエート、
O,O,O’,O’−テトラエチル−S,S’−メチレンジ(ホスホロジチオエート)、
O−(4−ブロモ−2,5−ジクロロフェニル)O,O−ジエチルホスホロチオエート、
S−4−クロロフェニルチオメチルO,O−ジエチルホスホロジチオエート、
O−2,5−ジクロロ−4−(メチルチオ)フェニルO,O−ジエチルホスホロジチオエート、
O−4−シアノフェニルO,O−ジメチルホスホロチオエート、
O,O−ジメチルO−2−メチルチオエチルホスホロチオエート、
O,O−ジエチルO−2−エチルチオエチルホスホロチオエート、
O−2,4−ジクロロフェニルO,O−ジエチルホスホロチオエート、
O−2,4−ジクロロフェニルO−エチルフェニルホスホロチオエート、
1,3−ジ(メトキシカルボニル)−1−プロペン−2−イルジメチルホスフェート、
2−クロロ−1−(2,4−ジクロロフェニル)ビニルジエチルホスフェート、
O,O−ジメチル−O−4−ニトロ−m−トリルホスホロチオエート、
O,O−ジメチル−O−4−メチルチオ−m−トリルホスホロチオエート、
O−(5−クロロ−1−イソプロピル−1,2,4−トリアゾリル−3−イル)O,O−ジエチルホスホロチオエート、
S−2−イソプロピルチオエチルO,O−ジメチルホスホロジチオエート、
4−(メチルチオ)フェニルジプロピルホスフェート、
1,2−ジブロモ−2,2−ジクロロエチルジメチルホスフェート、
O,O−ジエチル−アルファ−シアノベンジリデンアミノ−オキシホスホロチオエート、
O,O−ジエチルO−4−ニトロフェニルホスホロチオエート、
O−2−ジエチルアミノ−6−メチルピリミジン−4−イルO,O−ジエチルホスホロチオエート、
O−2−ジエチルアミノ−6−メチルピリミジン−4−イルO,O−ジメチルホスホロチオエート、
O,O,O’,O’−テトラエチルジチオピロホスフェート、
O,O,O’,O’−テトラメチル−O,O’−チオジ−p−フェニレンジホスホロチオエート、
S,S’−(1,4−ジオキサン−2,3−ジイル)O,O,O’,O’−テトラエチルジ(ホスホロジチオエート)、
S−2−エチルチオエチル−O,O−ジメチルホスホロジチオエート、
3−フェノキシベンジル−(+−)−cis−transクリサンテメート、
ピレトリン−2−(2−ブトキシエトキシ)エチルチオシアネートイソボルニル−チオシアノアセテート、
二硫化炭素 2−(4−tert−ブチルフェノキシ)シクロヘキシルプロパ−2−イニルサルファイト(carbon disulfide 2-(4-tertio-butylphenoxy)cyclohexyl prop-2-ynyl sulphite)、
4−6−ジニトロ−6−オクチルフェニルクロトネート、
エチル4,4’−ジクロロベンジレート、
O,O−ジエチル−O−1−フェニル−1,2,4−トリアゾール−3−イルホスホロチオエート、
O−エチルO−2,4,5−トリクロロフェニルエチルホスホノチオエート、
(+−)−3−アリル−2−メチル−4−オキソシクロペンタ−2−エニル−(+)−cis,trans−クリサンテメート、及び
(+−)−3−アリル−2−メチル−4−オキソシクロペンタ−2−エニル−(+)−trans−クリサンテメート
が挙げられる。
銅ナフテネート、
5−エトキシ−3−トリクロロメチル−1,2,4−チアジアゾール、及び
O−エチルS,S−ジフェニルホスホロジチオエート
が挙げられる。
6‐ブトキシカルボニル−2,3−ジヒドロ−2,2−ジメチルピラン−4−オン、
N,N−ジエチル−m−トルアミド、
ジブチルフタレートジブチルスクシネート、
1,5a,6,9,9a,9b−ヘキサヒドロ−4a(4H)−ジベンゾフランカルボキシアルデヒド、及び
ジプロピルピリジン−2,5−ジカルボキシレート
が挙げられる。
2−(1,2−ジメチルプロピルアミノ)−4−エチル−アミノ−6−メチルチオ−1,3,5−トリアジン−2−エチル−5−メチル−5−(2−メチルベンジルオキシ)−1,3−ジオキサン、
S−エチル−N−シクロヘキシル−N−エチルチオカルバメート、
S−2,3−ジクロロアリルジ−イソプロピルチオカルバメート、
S−プロピルブチルエチルチオカルバキセート(S-propyl butylethylthiocarbaxate)、
S−2,3,3−トリクロロアリルジイソプロピルチオカルバメート、
S−エチルジプロピルチオカルバメート、
S−4−クロロベンジルジエチルチオカルバメート、
S−エチルジイソブチルチオカルバメート、
S−ベンジルジ−secブチルチオカルバメート、
S−プロピルジプロピルチオカルバメート、
S−エチルヘキサヒドロ−1H−アゼピン−1−カルボチオエート、
N,N−ジアリルクロロアセタミド、
N−ブトキシメチル−アルファ−クロロ−2’,6’−ジエチルアセトアニリド、
N−(2−メルカプトエチル)ベンゼンスルホンアラニド(N-(2-mercaptoethyl)benzenesulfonarnide)のS−(O,O−ジイソプロピルホスホロジチオエート)エステル、
アルファ−クロロ−6’−エチルN−(2−メトキシ−1−メチル]エチル)−アセタミド、
N−ベンジルN−イソプロピルトリメチルアセタミド、及び
2−クロロアリルジエチルジチオカルバメート
が挙げられる。
− 2−ヒドロキシ−2−メチル−1−フェニル−1−プロパノンなどのα−ヒドロキシケトン;
− 2−ベンジル−2−ジメチルアミノ−1−(4−モルホリノフェニル)−ブタノン−1などのα−アミノケトン;
− ベンジルジメチルケタールなどのα−ジカルボニル誘導体;
− ビス−アシルホスフィンオキシドなどのアシルホスフィンオキシド;
− ベンゾフェノンなどの芳香族ケトン;
− フェニルグリオキシル酸メチルエステルなどのフェニルグリオキシレート;
− [1−(4−フェニルスルファニルベンゾイル)へプチリデンアミノ]ベンゾエートなどのオキシムエステル;
− スルホニウム塩、
− ヨードニウム塩、及び
− オキシムスルホネート
から成る群より選択されてよい。
− フッ素化基などの疎水性基、例えば、トリフルオロエチルメタクリレート、トリフルオロエチルアクリレート、テトラフルオロプロピルメタクリレート、ペンタフルオロプロピルアクリレート、ヘキサフルオロブチルアクリレート、又はフルオロフェニルイソシアネート;
− 一級、二級、若しくは三級アミン、カルボン酸、ホスフェート、サルフェート、ナイトレート、又はカーボネートなどのpH感受性基;
− アゾベンゼン、スピロピラン、2−ジアゾ−1,2−ナフトキノン、o−ニトロベンジル、チオール、若しくは6‐ニトロ−ベラトロイロキシカルボニルなどのUV感受性又はUV開裂性基(フォトクロミック基とも称される)、例えば、ポリ(エチレンオキシド)−ブロック−ポリ(2−ニトロベンジルメタクリレート)、及び例えばLiu et al., Polymer Chemistry 2013, 4, 3431-3443に記載のような他のブロックコポリマー;
− o−ニトロベンジル若しくは2−ジアゾ−1,2−ナフトキノンなどのIR感受性又はIR開裂性基、例えば、Liu et al., Polymer Chemistry 2013, 4, 3431-3443に記載のポリマー;並びに
− ポリ(N−イソプロピルアクリルアミド)などの温度感受性基。
工程b)では、工程a)で得られた第一のエマルジョンが、液体組成物C3に添加され、添加は撹拌下で行われる。これは、組成物C1、組成物C2、及び組成物C3の混合物を乳化するために、第一のエマルジョンが添加される間、組成物C3が、典型的には機械的に撹拌されることを意味する。
工程c)では、連続相中に分散された多分散液滴から成る工程b)で得られた第二のエマルジョンが、1000s−1〜100000s−1を含む均一な制御されたせん断速度を適用するミキサー中でせん断処理される。
− 2つの同心回転シリンダー(クエット型ミキサー(Couette-geometry mixer)とも称される)、
− 2つの平行な回転ディスク、又は
− 2つの平行な振動プレート
によって形成されるセルを通る循環時に、均一な制御されたせん断を受け得る。
工程d)では、第三のエマルジョンの二重液滴が架橋されて、活性物質をカプセル化しているマイクロカプセルが得られる。
本発明の方法は、活性物質を含む組成物C1から成るコアを含み、コアは、重合された組成物C2の固体(重合又は架橋されている)シェルによってカプセル化されている、固体マイクロカプセルの作製を可能とするものである。
− 上記で定める通りの少なくとも1つの活性物質を含む組成物を含むコア、及び
− コアを取り囲む固体架橋シェル
を含み、マイクロカプセル径分布の標準偏差は、25%未満、又は1μm未満である。
以下の物質を、組成物C1として問題なく用いた:
− 89% CN981(Sartomer、Arkema)
− 10% ヘキサンジオールジアクリレート
− 1% Darocure 1173
実施例1で作製したマイクロカプセルのTEM画像に対して画像解析を行った(Image Jソフトウェア使用)。結果(マイクロカプセルの平均径及びシェル厚さの分布、及び標準偏差)を以下の表に示す。
この実施例では、Dow Corningから市販されている2成分キット「Sylgard 184シリコンエラストマー」を用いた。A及びBと称する2つの成分は、それぞれ、シロキサンモノマー組成物及びシロキサン架橋剤組成物である。A:B=10:1の重量比で一緒に混合されると、これら2つの成分は、室温では24時間以内に、90℃では2時間以内に、架橋された固体エラストマーを形成する。
− 89% CN981(Sartomer、Arkema)
− 10% ヘキサンジオールジアクリレート
− 1% Darocure 1173(光開始剤)
三枚羽根プロペラを備えたオーバーヘッドスターラー(Heidolph RZR 2021)を用いてエマルジョンを作製した。混合速度は、1000rpmに設定した。すべての工程は、室温で行った。
工程d)から得られたマイクロカプセル分散体の粘度を、レオメーターHAAKE Rheostress(商標)600を用い、60日間にわたって25℃で測定した。
60日後、固体マイクロカプセル分散体を、17200s−1のせん断速度に相当する680rpmの回転速度及び0.5mL/分の流速で、クエット型ミキサー中でせん断処理し、続いて90℃で2時間放置した。
固体マイクロカプセルを、以下の組成物C1、C2、及びC3を用いて作製した:
− 組成物C1:ExxonMobil PAO 40(25℃での粘度が892mPa・sであるポリアルファオレフィン)
− 組成物C2:
・ 89% CN981(Sartomer、Arkema)
・ 10% ヘキサンジオールジアクリレート
・ 1% Darocure 1173(光開始剤)
− 組成物C3:ExxonMobil PAO 100(25℃での粘度が2989mPa・sであるポリアルファオレフィン)
− 三枚羽根プロペラを備えたオーバーヘッドスターラー(Heidolph RZR 2021)、混合速度1000rpm、
− Ika T25 Ultra−Turraxミキサー、24000rpmで5分間、又は
− クエット型ミキサー、9373s−1のせん断速度に相当する450rpmの回転速度及び8mL/分の流速(均一な高せん断混合、本発明の方法の工程c)の条件に相当)
Claims (19)
- a)少なくとも1種類の活性物質を含む組成物C1を、架橋性液体組成物C2に混合下で添加して、組成物C2中に分散された組成物C1の液滴(1)を含む第一のエマルジョンを得る工程であって、
前記活性物質は、潤滑剤、燃料、若しくはビチューメン産業に、又は掘削汚泥若しくは泥水に用いられる添加剤でも、又は石油探査/採油に用いられる添加剤でもなく、組成物C1及び組成物C2は互いに不混和性である、工程、
b)工程a)で得られた前記第一のエマルジョンを、液体組成物C3に混合下で添加して、組成物C3中に分散された液滴(5)を含む第二のエマルジョンを得る工程であって、組成物C3及び組成物C2は互いに不混和性である、工程、
c)工程b)で得られた前記第二のエマルジョンを、1000s−1〜100000s−1の均一な制御されたせん断速度を前記第二のエマルジョンに適用するミキサーに充填して、組成物C3中に分散された液滴(10)を含む第三のエマルジョンを得る工程、及び、
d)工程c)で得られた前記液滴(10)を架橋して、組成物C3中に分散された固体マイクロカプセル(20)を得る工程、
を含む、固体マイクロカプセル(20)を作製するための方法。 - 前記活性物質が、組成物C1中に溶解されている、請求項1に記載の方法。
- 前記活性物質が、固体粒子の形態で組成物C1中に分散されている、請求項1に記載の方法。
- 組成物C2が、少なくとも1種類のモノマー又はポリマー、少なくとも1種類の架橋剤、及び少なくとも1種類の重合開始剤を含む、請求項1〜請求項3のいずれか一項に記載の方法。
- 組成物C2の25℃での粘度が、500mPa・s〜100000mPa・sである、請求項1〜請求項4のいずれか一項に記載の方法。
- 組成物C2の粘度が、組成物C1の粘度よりも高い、請求項1〜請求項5のいずれか一項に記載の方法。
- 工程a)において、組成物C1の体積の組成物C2の体積に対する比が、1:10〜10:1である、請求項1〜請求項6のいずれか一項に記載の方法。
- 組成物C3の25℃での粘度が、工程a)で得られる前記第一のエマルジョンの25℃での粘度よりも高い、請求項1〜請求項7のいずれか一項に記載の方法。
- 工程b)において、前記第一のエマルジョンの体積の組成物C3の体積に対する比が、1:10〜10:1である、請求項1〜請求項8のいずれか一項に記載の方法。
- 工程c)で用いられる前記ミキサーが、内半径Roの外側シリンダーと外半径Riの内側シリンダーとの2つの同心シリンダーとを備え、外側シリンダーは固定され、内側シリンダーは角速度ωで回転する、クエット型ミキサーである請求項1〜請求項9のいずれか一項に記載の方法。
- 前記回転する内側シリンダーの前記角速度ωが、30rad・s−1以上である、請求項10に記載の方法。
- 前記2つの同心シリンダー間の間隔d=Ro−Riが、50μm〜1000μmである、請求項10又は請求項11に記載の方法。
- 工程d)において、前記架橋が、工程c)で得られた二重液滴(10)への、組成物C2の前記架橋を開始することができる光源、好ましくはUV光源からの照射によって行われる、請求項1〜請求項12のいずれか一項に記載の方法。
- − 請求項1に記載の少なくとも1種類の活性物質を含有する組成物を含むコア、及び、
− 前記コアを取り囲む固体架橋シェル、
を各々のマイクロカプセル(20)が含み、径分布の標準偏差が25%未満又は1μm未満である、請求項1〜請求項13のいずれか一項に記載の方法によって得られる一連の固体マイクロカプセル(20)。 - 前記マイクロカプセル(20)の平均径が、10μm以下である、請求項14に記載の一連の固体マイクロカプセル(20)。
- 各マイクロカプセル(20)が、界面活性剤を含まない、請求項14又は請求項15に記載の一連の固体マイクロカプセル(20)。
- 各マイクロカプセル(20)が、水を含まない、請求項14〜請求項16のいずれか一項に記載の一連の固体マイクロカプセル(20)。
- 請求項14〜請求項17のいずれか一項に記載の一連の固体マイクロカプセル(20)を含む組成物。
- 請求項14〜請求項17のいずれか一項に記載の一連の固体マイクロカプセル(20)を含む組成物に、機械的せん断応力を適用する工程を含む、活性物質を放出するための方法。
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JP2020500707A (ja) * | 2016-12-01 | 2020-01-16 | カリシア | 光重合工程を含むサイズ制御されたマイクロカプセルの製造方法 |
JP2022509405A (ja) * | 2018-10-31 | 2022-01-20 | ソルベイ スペシャルティ ポリマーズ イタリー エス.ピー.エー. | 自己潤滑性コーティング組成物 |
JP2022509404A (ja) * | 2018-10-31 | 2022-01-20 | ソルベイ スペシャルティ ポリマーズ イタリー エス.ピー.エー. | エラストマーの硬化性組成物 |
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JP7470704B2 (ja) | 2018-10-31 | 2024-04-18 | ソルベイ スペシャルティ ポリマーズ イタリー エス.ピー.エー. | 自己潤滑性コーティング組成物 |
JP7470703B2 (ja) | 2018-10-31 | 2024-04-18 | ソルベイ スペシャルティ ポリマーズ イタリー エス.ピー.エー. | エラストマーの硬化性組成物 |
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CN108348886B (zh) | 2021-09-10 |
US20180185809A1 (en) | 2018-07-05 |
BR112018005107B1 (pt) | 2021-06-22 |
SA518391111B1 (ar) | 2021-11-25 |
EP3144058A1 (en) | 2017-03-22 |
KR20180057625A (ko) | 2018-05-30 |
MX2018003286A (es) | 2018-08-16 |
EP3349891B1 (en) | 2021-04-21 |
JP6888759B2 (ja) | 2021-06-16 |
EP3349891A1 (en) | 2018-07-25 |
WO2017046360A1 (en) | 2017-03-23 |
CA2998963A1 (en) | 2017-03-23 |
US10807060B2 (en) | 2020-10-20 |
CA2998963C (en) | 2023-08-29 |
KR102616379B1 (ko) | 2023-12-26 |
CN108348886A (zh) | 2018-07-31 |
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