JP2021516678A - 微粉化された1,4−ジ(ベンゾオキサゾール−2’−イル)ベンゼン - Google Patents
微粉化された1,4−ジ(ベンゾオキサゾール−2’−イル)ベンゼン Download PDFInfo
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- JP2021516678A JP2021516678A JP2020545167A JP2020545167A JP2021516678A JP 2021516678 A JP2021516678 A JP 2021516678A JP 2020545167 A JP2020545167 A JP 2020545167A JP 2020545167 A JP2020545167 A JP 2020545167A JP 2021516678 A JP2021516678 A JP 2021516678A
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- benzoxazole
- benzene
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Abstract
Description
(i)水性分散液の総重量を基準として20〜70重量%、好ましくは25〜60重量%の、本明細書に示すあらゆる好ましい事項及び定義を有する微粉化された1,4−ジ(ベンゾオキサゾール−2’−イル)ベンゼンと、
(ii)水性分散液の総重量を基準として2〜15重量%、好ましくは5〜10重量%の、上に示したあらゆる好ましい事項及び定義を有するC8〜16アルキルポリグルコシドと、
(iii)水性分散液の総重量を基準として0〜3重量%、好ましくは0.1〜2重量%の、少なくとも1種の添加剤と、
(iv)水性分散液の総重量を基準として25〜60重量%、好ましくは30〜45重量%の水と
から基本的になる。
[1.微粉化された1,4−ジ(ベンゾオキサゾール−2’−イル)ベンゼンの調製]
[1.1 一般的方法]
粒子径は、全てISO 13320:2009に概説されている方法に準拠し、Malvern Mastersizer 2000(レーザー回折)により、且つ/又はCoulter Delsa Nano S(動的レーザー散乱)により測定した。
ポリリン酸702g及びメタンスルホン酸4.28mlの混合物を90℃に加熱した。テレフタル酸65g及び2−アミノフェノール107gを加えた。混合物を180℃の不活性雰囲気中、8時間撹拌した後、氷水に移した。析出した生成物を濾過して水及び酢酸で洗浄した。析出物を水中に分散させ、pHを水酸化ナトリウムでpH8.0に調整し、濾過して水で洗浄した。粗生成物をトルエン及び1−ブタノールの3.3:1混合物中に懸濁させ、85℃で1時間撹拌し、濾過してジエチルエーテルで洗浄し、乾燥させた。得られた非晶質固体1,4−ジ(ベンゾオキサゾール−2’−イル)ベンゼンの粗大粒子は、粒子径Dn50が380nm(Malvern)であった。
(1.2)で概説したように得られたDBO−400が175g、水が324g及びGreen APG 0810が65gの懸濁液を調製した。次いで、この懸濁液をLabStar実験用粉砕機において、イットリウム安定化酸化ジルコニウム磨砕ビーズ(0.3mm、東ソーセラミックス(Tosoh Ceramic)、日本国)を使用して2時間粉砕し、粉砕室を冷却した(−12℃の飽和食塩水)。磨砕ビーズを除去した後、微粉化された1,4−ジ(ベンゾオキサゾール−2’−イル)ベンゼンの30%水性分散液を得た。
粒子径:
Malvern:Dn50 186nm(Dn10=126nm、Dn90=355nm)
Coulter:平均値(強度分布):171nm
E 1/1:839
DSC:開始温度:350℃;熱容量:132J/g
UVB:UVA比:0.49
X線:図1、線4
(1.2)に概説したように得られた粗大粒子をo−ジクロロベンゼンから再結晶させた後、乾燥させることにより、結晶性1,4−ジ(ベンゾオキサゾール−2’−イル)ベンゼンの粗大粒子73.0%を得、次いでこれを、(1.3)に概説したプロセスと同様に粉砕した。磨砕ビーズを除去した後、結晶性1,4−ジ(ベンゾオキサゾール−2’−イル)ベンゼンの30%水性分散液を得た。
粒子径:
Coulter:平均値(強度分布):193nm
E 1/1:719;
DSC:開始温度:352℃;熱容量:153J/g。
UVB:UVA比:0.35
X線:図1、線2
(1.2)で概説した通りに得られたDBO−400(A)が1.8g、水が3.51g及びGreen APG 0810が0.69gの懸濁液を調製した。次いで、この懸濁液を、周囲温度(22℃)で磁気的撹拌を用いて、均質な分散液が得られるまで撹拌した。マグネチックスターラーバーを取り出した後、平均粒子径Dn50が380nm(Malvern)である微粉化された1,4−ジ(ベンゾオキサゾール−2’−イル)ベンゼンの30%水性分散液を得た。
表1に概要を示す配合物(O/Wエマルジョン)を当該技術分野における標準的な方法に従って調製した。
活性物質の濃度を0.001%(w/v)として、1−メチル−2−ピロリジノン中に可溶化するか又は水中に分散するかのいずれかとし、それぞれの微粉化されたUV遮蔽剤のUVスペクトルを測定し、290〜320nm(UVB)の面積%を320〜400nm(UVA)の面積%で除すことによって比を算出することにより、UVB:UVA比を求めた。
表3に概要を示す配合物を当該技術分野における標準的な方法に従って調製した。その後、in vitro SPFを製造直後(t0)及び室温で1か月間保管した後(t1)に評価した。in vitro SPF試験をPMMAプレート(SchoenbergからのWW5、5cm×5cm、粗さ5mμ)上で実施し、各配合物32.5mg(即ち1.3mg/cm2)をPMMAプレート上に均一に塗布して15分間乾燥させた。
以下に概説するスポンジ試験を用いて物質の移行を測定した。
− スポンジクロス(Weita AGからのWeitawip Claire:セルロース/綿繊維混合物、200g/m2、厚さ5mm)を76mm×26mmの小片に裁断する
− スポンジ試料を風袋引きする
− 各試料(=化粧用組成物)400mgを適用し、76mm×26mmのスポンジ表面全体に均一に分布させる
− 適用した試料を含むスポンジを秤量する
− スライドガラス(ガラスプレート76mm×26mm×1mm)を風袋引きする
− スライドガラス(ガラスプレート)をスポンジ上面に載せ、天秤用の500gの錘(高さ:6.3cm、接触面の直径:3.7cm)を10秒間載せて、試料に一定の圧力を印加する
− スライドガラスを垂直方向に慎重に取り除く
− 取り除いたスライドガラスを秤量し、これに従ってガラスプレートに移行した試料の量を決定する
− 各組成物に関して試験を10回ずつ繰り返すことにより、各試料の平均値(中間値)を得る。
Claims (15)
- 前記平均粒子径は、50〜300nmの範囲、好ましくは120〜280nmの範囲、最も好ましくは150〜220nmの範囲において選択されることを特徴とする、請求項1に記載の微粉化された1,4−ジ(ベンゾオキサゾール−2’−イル)ベンゼン。
- 非晶質固体形態であることを特徴とする、請求項1又は2に記載の微粉化された1,4−ジ(ベンゾオキサゾール−2’−イル)ベンゼン。
- 請求項1〜3のいずれか一項に記載の微粉化された1,4−ジ(ベンゾオキサゾール−2’−イル)ベンゼンを含む水性分散液。
- 前記水性分散液中の前記微粉化された1,4−ジ(ベンゾオキサゾール−2’−イル)ベンゼンの量は、前記水性分散液の総重量を基準として25〜60重量%の範囲、好ましくは25〜55重量%の範囲において選択されることを特徴とする、請求項4に記載の水性分散液。
- 少なくとも1種の磨砕助剤及び/又は少なくとも1種の添加剤を更に含むことを特徴とする、請求項3又は4に記載の水性分散液。
- 前記少なくとも1種の磨砕助剤は、アルキルポリグルコシドであり、及び前記少なくとも1種の添加剤は、湿潤剤、増粘剤及び消泡剤並びにこれらの混合物からなる群から選択されることを特徴とする、請求項6に記載の水性分散液。
- 前記少なくとも1種の添加剤は、プロピレングリコール、キサンタンガム、ジェランガム及びシメチコン並びにこれらの混合物からなる群から選択されることを特徴とする、請求項6又は7に記載の水性分散液。
- 0.40〜0.55の範囲、好ましくは0.44〜0.54の範囲、最も好ましくは0.47〜0.51の範囲におけるUVB:UVA比によって特徴付けられることを特徴とする、請求項1〜8のいずれか一項に記載の微粉化された1,4−ジ(ベンゾオキサゾール−2’−イル)ベンゼン。
- ≧780の、320nmにおける比吸光度E 1/1によって特徴付けられることを特徴とする、請求項1〜9のいずれか一項に記載の微粉化された1,4−ジ(ベンゾオキサゾール−2’−イル)ベンゼン。
- 請求項1〜10のいずれか一項に記載の微粉化された1,4−ジ(ベンゾオキサゾール−2’−イル)ベンゼン又はその水性分散液を含む局所用組成物。
- 前記局所用組成物中の前記微粉化された1,4−ジ(ベンゾオキサゾール−2’−イル)ベンゼンの量は、前記局所用組成物の総重量を基準として0.1〜20重量%の範囲、好ましくは0.5〜15重量%の範囲、最も好ましくは1〜10重量%の範囲において選択されることを特徴とする、請求項10に記載の局所用組成物。
- 水中油型(O/W)エマルジョンの形態又は油中水型(W/O)エマルジョンの形態であることを特徴とする、請求項11又は12に記載の局所用組成物。
- 請求項1〜8のいずれか一項に記載の微粉化された1,4−ジ(ベンゾオキサゾール−2’−イル)ベンゼン又はその水性分散液を調製する方法であって、
(1)式(I)の前記1,4−ジ(ベンゾオキサゾール−2’−イル)ベンゼンの粗大粒子、水及び粉砕媒体並びに任意選択的に磨砕助剤及び/又は更なる添加剤の混合物を調製するステップと、
(2)前記混合物を、300nm未満の平均粒子径Dn50が得られるまで磨砕するステップと
を包含する方法。 - 局所用組成物中に含有される脂肪及び油の表面への移行を低減するための、請求項1〜10のいずれか一項に記載の微粉化された1,4−ジ(ベンゾオキサゾール−2’−イル)ベンゼン又はその水性分散液の使用。
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PCT/EP2019/056881 WO2019180042A1 (en) | 2018-03-20 | 2019-03-19 | Micronized 1,4-di(benzoxazol-2'-yl)benzene |
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JP2003192557A (ja) * | 2001-12-07 | 2003-07-09 | L'oreal Sa | 遮蔽剤の相乗混合物をベースにした抗日光化粧品用組成物及びその用途 |
JP2017101091A (ja) * | 2014-04-02 | 2017-06-08 | 御国色素株式会社 | 紫外線吸収剤分散体 |
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GB9403451D0 (en) | 1994-02-23 | 1994-04-13 | Ciba Geigy Ag | Sunscreen compositions |
GB9515048D0 (en) | 1995-07-22 | 1995-09-20 | Ciba Geigy Ag | Sunscreen compositions |
CA2315544A1 (en) * | 2000-08-08 | 2002-02-08 | Alan K. Olson | Fracturing method using aqueous or acid based fluids |
JP2011528022A (ja) * | 2008-07-16 | 2011-11-10 | ディーエスエム アイピー アセッツ ビー.ブイ. | 化粧品組成物 |
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- 2019-03-19 WO PCT/EP2019/056881 patent/WO2019180042A1/en unknown
- 2019-03-19 BR BR112020018962-6A patent/BR112020018962A2/pt unknown
- 2019-03-19 KR KR1020207029748A patent/KR20200135813A/ko not_active Application Discontinuation
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US6030607A (en) * | 1997-04-08 | 2000-02-29 | Biocycle Laboratories, Inc. | Water soluble sun tanning solution |
WO2002039972A1 (fr) * | 2000-11-17 | 2002-05-23 | L'oreal | Filtres uv organiques insolubles et leur utilisation en cosmetique |
JP2003192557A (ja) * | 2001-12-07 | 2003-07-09 | L'oreal Sa | 遮蔽剤の相乗混合物をベースにした抗日光化粧品用組成物及びその用途 |
JP2017101091A (ja) * | 2014-04-02 | 2017-06-08 | 御国色素株式会社 | 紫外線吸収剤分散体 |
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