JP5226787B2 - 染料担持粒子 - Google Patents
染料担持粒子 Download PDFInfo
- Publication number
- JP5226787B2 JP5226787B2 JP2010520666A JP2010520666A JP5226787B2 JP 5226787 B2 JP5226787 B2 JP 5226787B2 JP 2010520666 A JP2010520666 A JP 2010520666A JP 2010520666 A JP2010520666 A JP 2010520666A JP 5226787 B2 JP5226787 B2 JP 5226787B2
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- particles
- dye
- encapsulant
- silica
- dyes
- Prior art date
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Links
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- 239000008393 encapsulating agent Substances 0.000 claims description 36
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- 238000010438 heat treatment Methods 0.000 claims description 4
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- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
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Images
Classifications
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- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
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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
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
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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
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0001—Post-treatment of organic pigments or dyes
- C09B67/0004—Coated particulate pigments or dyes
- C09B67/0008—Coated particulate pigments or dyes with organic coatings
- C09B67/0013—Coated particulate pigments or dyes with organic coatings with polymeric coatings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0097—Dye preparations of special physical nature; Tablets, films, extrusion, microcapsules, sheets, pads, bags with dyes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/41—Particular ingredients further characterized by their size
- A61K2800/412—Microsized, i.e. having sizes between 0.1 and 100 microns
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/41—Particular ingredients further characterized by their size
- A61K2800/413—Nanosized, i.e. having sizes below 100 nm
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/42—Colour properties
- A61K2800/43—Pigments; Dyes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
- Y10T428/2984—Microcapsule with fluid core [includes liposome]
Description
(a)X線回折図形(x-ray diffractogram)において0.37〜0.42nmのd間隔に対応する2つのθ角の間に中心を置く広範なピークが存在し、2θ=5〜10°の半値全幅(FWHM)である;
(b)0.37〜0.42nmで分離している結晶面の間隔に対応するシャープな粉末X線回折のピークが存在しない;
(c)ミクロトームによって作製された試料のTEM画像によって測定したときに、メソ結晶秩序(それぞれの最高次ブラッグピークが2〜50nmの範囲にある−秩序化メソ構造材料の典型)がない;
(d)0.1〜50nmのd間隔に対応する2つのθ角の範囲に多数のシャープなピークが存在しない。
実施例1:タートラジン(食品、医薬品及び化粧品用黄色5号)担持シリカの調製
タートラジンナトリウム含有シリカを合成する第1工程として、染料(シグマ(Sigma)よりT0388−100G(CAS番号1934−21−0)として市販されている)を、イオン交換樹脂(米国ミシガン州のダウ・ケミカル社(Dow Chemical Comp.)より市販されているダウエクス(Dowex)50Wx8型)のカラムを用いてイオン交換した。これは、市販のタートラジンの使用が、テトラエチルオルトシリケート/エタノール/塩酸(TEOS/EtOH/HCl)封入剤混合物の凝集を誘発することから、必要であった。
カラムに、317gのダウエクス(Dowex)50Wx8を装填して、400mLのベッド体積を得た。
工程1−洗浄:残留するナトリウムカチオンを除去するため、カラムを2.5lの脱イオン水で、pH6にて5〜10分間溶出した。
工程2−再コンディショニング:結合したナトリウムカチオンを除去するため、カラムを、400mLの7%HClを4バッチ通して洗浄した。カラム上のHClの接触時間は45分であった。
工程3−洗浄:工程1と同じ。
工程4−チャージ:工程2と同じであるが、HClの代わりに7%の塩化アンモニウム(NH4Cl)を使用して実施した。
工程5−洗浄:工程1と同じで、その目的は過剰なアンモニウムカチオンを除去することである。
タートラジンナトリウムの10%染料溶液を、水及びエタノールの酸性溶液で調製し、カラムを通して溶出した。この溶液を、その後の手順でタートラジン含有シリカの製造に使用した。
2バッチの着色シリカを、各々10.4gのTEOS、pH1.25前後の5.4gのHCl及び12.0gのエタノールを使用して調製した。前記構成成分を一緒に混合し、該混合物を30分間攪拌放置した。理論的に、このような混合物は、エアゾール化後に3gのシリカを与えるはずである。加えるタートラジン溶液の量の計算は、この理論的なシリカの量に基づく。イオン交換したタートラジン溶液を、続いて、4gのエタノールと混合した。
粒子1gにつき水200mLの量で、以下のようにして粒子を脱イオン水で洗浄した:5gの粒子をプラスチックボトルに入れ、1000mLの水を加えた。前記混合物を、5分間攪拌放置し、その後3500rpmで10分間遠心分離した。その後、沈降物を上澄み液から分離した。
遠心分離した混合物から得た沈降物を、ビーカー内で1000mLの水と混合し、2日間放置して沈降させた。得られた上澄み液を、続いて、ロールポンプを用いて別のビーカーにポンプ輸送した。上澄みが他のビーカーにポンプ輸送された後、それを3500rpmで20分間遠心分離し、得られた沈降物を標準的な分離技術を用いて液体から分離した。得られた粒子を、続いて、オーブン内で50℃で乾燥した。
得られた粒子の粒径を、マルバーンマスターサイザー(Malvern Master Sizer)2000装置を使用して測定したが、これは光錯乱により粒径を測定する。粒径分布を図4aに示す。
d(0.1):0.308μm(粒子の10%が、所与の体積平均値よりも小さい粒径を有する)
d(0.5):0.539μm(粒子の50%が、所与の体積平均値よりも小さい粒径を有する)
d(0.9):0.953μm(粒子の90%が、所与の体積平均値よりも小さい粒径を有する)
この赤色染料は、水に可溶性であるが、エタノールに不溶性である。ただし、TEOS混合物とブレンドしたときに凝集しなかったため、水溶液のイオン交換(実施例1でタートラジンに実施したような)は不要であった。更に、前記染料はエタノールに不溶性であるが、エアゾール混合物中の水の割合を増大させることによって直接使用することがまだ可能であった。
2バッチの着色シリカを、10.4gのTEOS、5.4gのpH2のHCl及び12.0gのエタノールを使用して調製した。前記構成成分を一緒に混合し、該混合物を30分間攪拌放置した。理論的に、前記混合物は、エアゾール化後に3gのシリカを与えるであろう。それゆえ、加えるアマランス溶液(シグマ(Sigma)から入手したものはカタログ番号A1016−100G(CAS番号915−67−3)であった)の量の計算は、このシリカの量に基づいた。これは次の通りであった:0.3gのアマランス粉末プラス10.0gのHCl(pH2)。前記2つの混合物を一緒に混合し、10分間攪拌放置した。前記混合物に、続いて実施例1のように噴霧乾燥、加熱、洗浄、粒子分離及び粒径測定を実施した。粒径の結果を図4bに示す。
d(0.1):0.322μm
d(0.5):0.592μm
d(0.9):1.130μm
この青色染料は水及びエタノールに可溶性であり、溶液のイオン交換は不要であった。
2バッチの着色シリカを、各々10.4gのTEOS、5.4gのHCl(pH2)及び8.0gのエタノールを使用して調製した。前記構成成分を一緒に混合し、該混合物を30分間攪拌放置した。理論的に、前記混合物は、エアゾール化後に3gのシリカを与えるであろう。それゆえ、加えるエリオグラウシン溶液の量の計算は、このシリカの量に基づいた。これは次の通りであった:0.3gのエリオグラウシン粉末(シグマ/アルドリッチ(Sigma/Aldrich)より入手、カタログ番号861146−25G(CAS番号3844−45−9))プラス2.0gのHCl(pH2)、3gのエタノール中。前記2つの混合物を一緒に混合し、10分間攪拌放置した。前記混合物に、続いて実施例1のように噴霧乾燥、加熱、洗浄、粒子分離及び粒径測定を実施した。粒径の結果を図4cに示す。
d(0.1):0.327μm
d(0.5):0.59μm
d(0.9):1.130μm
実施例4A
実施例1、2及び3の各々の生成物について、染料担持粒子0.2gを遠心管に入れ、10mLの水/プロパノール(1:1)混合物を加えた。前記遠心管を、2分間振盪し遠心分離した。上澄み液を沈降物から分離し、瓶に回収した。この作業を5回繰り返した。全5回の抽出物からの上澄み液を混合し、UV分光計を用いて分析した。結果を下表(3)に示す。
異なる量の染料を担持したシリカからのタートラジンの漏れを、以下のように調査した。それぞれ1%、5%、10%、12%及び15%のタートラジンを担持した粒子1gを瓶に入れ、100gの水を加えた。前記混合物を3時間攪拌放置し、その後、注射器を用いて各ボトルから5mLの部分を抽出した。この部分を、メンブレンフィルタ(0.45μm)で濾過し、UV−VIS分光光度計で分析した。重量%単位での漏れを、各試料について、図5に示された検量線を参考にして計算した。図は水中のイオン交換されたタートラジンで423nmにおける検量線を示す。
Claims (12)
- 非晶質のケイ質封入剤によって封入された1種以上の染料が粒子全体に均質に分散された分布を有する非晶質粒子であって、
前記非晶質粒子が該粒子の3重量%〜20重量%の染料を含み、
前記非晶質粒子が0.001〜0.03cm 3 /gの比内部気孔体積を有し、
前記ケイ質封入剤がシリカまたはケイ酸塩であり、
前記非晶質粒子がシェルを含まない、非晶質粒子。 - 前記封入剤がシリカである、請求項1に記載の粒子。
- 前記ケイ質封入剤が、チタン、スズ、ジルコニウム及びアルミニウムのうち1種以上を含む、請求項1に記載の粒子。
- 前記1種以上の染料がカチオン性である、請求項1〜3のいずれか一項に記載の粒子。
- 前記染料又は各染料がキサンテン、トリアリールメタン、アントラセン、モノアゾ染料又はこれらの混合物である、請求項1〜4のいずれか一項に記載の粒子。
- 前記粒子の5重量%〜15重量%の染料を含む、請求項1〜5のいずれか一項に記載の粒子。
- 1種以上の種類の無機粒子状物質を追加的に含む、請求項1〜6のいずれか一項に記載の粒子。
- 0.5m2/g〜5m2/gの比表面積を有する、請求項1〜7のいずれか一項に記載の粒子。
- 球状である、請求項1〜8のいずれか一項に記載の粒子。
- 前記ケイ質封入剤の酸性前駆体溶液のエアゾール化、続いてエアゾール化された液滴の加熱によるケイ質封入剤の架橋によって作製される、請求項1〜9のいずれか一項に記載の粒子。
- 請求項1〜10のいずれか一項に記載の粒子を含み、0超〜10μmの平均粒径を有する、複数個の粒子。
- 請求項7に記載の粒子を含み、10nm〜1μm未満の平均粒径を有する、複数個の粒子。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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EP07114266.5 | 2007-08-13 | ||
EP07114266A EP2062946B1 (en) | 2007-08-13 | 2007-08-13 | Dye-loaded particles |
PCT/IB2008/053257 WO2009022307A2 (en) | 2007-08-13 | 2008-08-13 | Dye-loaded particles |
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JP2010535928A JP2010535928A (ja) | 2010-11-25 |
JP5226787B2 true JP5226787B2 (ja) | 2013-07-03 |
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JP2010520666A Expired - Fee Related JP5226787B2 (ja) | 2007-08-13 | 2008-08-13 | 染料担持粒子 |
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US (1) | US20090263658A1 (ja) |
EP (1) | EP2062946B1 (ja) |
JP (1) | JP5226787B2 (ja) |
KR (1) | KR101199805B1 (ja) |
CN (1) | CN101827896B (ja) |
AU (1) | AU2008288147A1 (ja) |
CA (1) | CA2694625C (ja) |
HK (1) | HK1132289A1 (ja) |
WO (1) | WO2009022307A2 (ja) |
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-
2007
- 2007-08-13 EP EP07114266A patent/EP2062946B1/en not_active Not-in-force
-
2008
- 2008-08-12 US US12/228,374 patent/US20090263658A1/en not_active Abandoned
- 2008-08-13 AU AU2008288147A patent/AU2008288147A1/en not_active Abandoned
- 2008-08-13 KR KR1020107003330A patent/KR101199805B1/ko not_active IP Right Cessation
- 2008-08-13 CA CA2694625A patent/CA2694625C/en not_active Expired - Fee Related
- 2008-08-13 JP JP2010520666A patent/JP5226787B2/ja not_active Expired - Fee Related
- 2008-08-13 CN CN200880103013.4A patent/CN101827896B/zh not_active Expired - Fee Related
- 2008-08-13 WO PCT/IB2008/053257 patent/WO2009022307A2/en active Application Filing
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2009
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Also Published As
Publication number | Publication date |
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WO2009022307A2 (en) | 2009-02-19 |
CA2694625A1 (en) | 2009-02-19 |
US20090263658A1 (en) | 2009-10-22 |
KR20100037143A (ko) | 2010-04-08 |
EP2062946B1 (en) | 2012-06-06 |
CN101827896B (zh) | 2014-05-07 |
CN101827896A (zh) | 2010-09-08 |
WO2009022307A3 (en) | 2009-12-17 |
KR101199805B1 (ko) | 2012-11-12 |
HK1132289A1 (en) | 2010-02-19 |
EP2062946A1 (en) | 2009-05-27 |
AU2008288147A1 (en) | 2009-02-19 |
CA2694625C (en) | 2014-03-25 |
JP2010535928A (ja) | 2010-11-25 |
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