JP2016128499A - ポリアクリレートマイクロカプセルの堆積が増大されたパーソナルクレンジング組成物 - Google Patents
ポリアクリレートマイクロカプセルの堆積が増大されたパーソナルクレンジング組成物 Download PDFInfo
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/10—Washing or bathing preparations
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/11—Encapsulated compositions
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
- A61K8/463—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfuric acid derivatives, e.g. sodium lauryl sulfate
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/73—Polysaccharides
- A61K8/737—Galactomannans, e.g. guar; Derivatives thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/8141—Compositions of homopolymers or 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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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- 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
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- 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
- A61K2800/59—Mixtures
- A61K2800/596—Mixtures of surface active compounds
Abstract
Description
本明細書で使用するとき、用語「パーソナルクレンジング組成物」は、特に指示がない限り、皮膚及び/又は毛髪を包含する体の角質表面に塗布することができる任意のパーソナルクレンジング組成物を含む。パーソナルクレンジング組成物は、例えば、固形石鹸、液体、エマルション、シャワーゲル、粉末、スティック、ペースト、マウスウォッシュ、フォームバス、プレシェーブ製品、及びシェービングに使用するデバイスであることができる。
消費者は、クレンジングプロセスの間、封入された有益剤をその毛髪及び/又は皮膚上に堆積及び保持するパーソナルクレンジング組成物を望む。従来より、マイクロカプセルの堆積を改善するために種々のアプローチがとられており、例として(1)マイクロカプセルに共有結合する特異なブロックコポリマーを使用する、及び(2)問題の基材に対するマイクロカプセルの親和性を増大するためにカチオン性水溶性ポリマーを用いてマイクロカプセルをコーティングすることが挙げられる。しかし、従来のアプローチよりも堆積が改善されることが望ましい。
アニオン性乳化剤の添加により、マイクロカプセルの外表面に特定のカチオン性堆積ポリマーを有する微細構造体が形成される。すなわち、アニオン性乳化剤はマイクロカプセルの外表面の少なくとも一部であるか、又はマイクロカプセルの外表面に物理的若しくは化学的に結合している。このような物理的結合としては、例えば、水素結合、イオン性相互作用、疎水性相互作用、及び電子移動相互作用が挙げられる。このような化学的結合としては、例えば、共有結合グラフト化及び架橋のような共有結合が挙げられる。
マイクロカプセル化の種々のプロセス、並びに代表的な方法及び材料は、米国特許第6,592,990号;米国特許第2,730,456号;米国特許第2,800,457号;米国特許第2,800,458号;及び米国特許第4,552,811号に記載されている。本明細書にわたって記載される各特許は、それぞれがマイクロカプセル化プロセス及び材料に関する手引きを提供する範囲で、参照により本明細書に組み込まれる。
アニオン性ポリアクリレートマイクロカプセルは、次のいずれかで形成できる:(1)既に形成されたマイクロカプセルをアニオン性乳化剤でコーティングする;又は(2)マイクロカプセル製造プロセスの間にアニオン性乳化剤をマイクロカプセルに添加する。いかなる既知のマイクロカプセル作製方法も本明細書で有用である。ポリアクリレートマイクロカプセルの製造方法の例は、米国特許出願公開第61/328949号;米国特許出願公開第61/328954号;米国特許出願公開第61/328962号;及び米国特許出願公開第61/328967号に開示されている。
本発明の1つの実施形態では、アニオン性乳化剤は既に形成されたポリアクリレートマイクロカプセルに添加される。アニオン性乳化剤は水素結合、ファンデルワールス力、イオン相互作用、疎水性相互作用、又は化学反応によりマイクロカプセルの表面に堆積する。1つの態様において、アニオン性乳化剤は、ポリアクリレートマイクロカプセルの外表面の少なくとも一部を取り囲むか又はポリアクリレートマイクロカプセルの外表面に物理的若しくは化学的に結合する。
別の実施形態では、アニオン性乳化剤は、マイクロカプセル製造プロセスにおいてマイクロカプセル表面に会合する。マイクロカプセルを製造する際は、アニオン性乳化剤を水相に可溶化し、水相は油の乳化の前に、任意にフリーラジカル反応開始剤を含有してもよい。続いて、過剰な水相を油相に添加して水中油型エマルションを形成する。続いてこのエマルションを、油相及び水相の一方又は両方に存在するフリーラジカルを分解するのに十分な時間及び温度で加熱する。マイクロカプセル壁材料は、それによって、水相と油相との界面で形成される。1つの実施形態では、乳化剤がアクリレート部分を含む場合、この乳化剤は界面壁材料に化学的に結合するようになる場合がある。
アニオン性ポリアクリレートマイクロカプセルをいずれかの形成工程によって形成した後、アニオン性ポリアクリレートマイクロカプセルを特定のカチオン性堆積ポリマーに添加してプレミックスを形成する。驚くべきことに、ポリアクリレートマイクロカプセル上のアニオン電荷は、プレミックス中のカチオン性堆積ポリマーと組み合わさったときにマイクロカプセルのシェル上に微細構造体の形成を引き起こすことが見出された。このプレミックスは、アニオン電荷及び特定のカチオン性堆積ポリマーのないマイクロカプセルよりも高い毛髪及び/又は皮膚に対する粘弾性を有するアニオン性ポリアクリレートマイクロカプセルを示し、したがって部位に利益を与える。
1つの実施形態では、アニオン性ポリアクリレートマイクロカプセルはスラリーに含有される。このスラリーを補助成分と組み合わせて、組成物、例えば、コンディショニング消費者製品を形成してもよい。
本発明のパーソナルクレンジング組成物は、アニオン性ポリアクリレートマイクロカプセルに添加されたときにプレミックスを形成するカチオン性堆積ポリマーを含む。いかなる既知の天然又は合成カチオン性堆積ポリマーもここで使用できる。例として、米国特許第6,649,155号;米国特許出願公開第12/103,902号;米国特許出願公開第2008/0206355号;及び米国特許出願公開第2006/0099167(A1)号に開示されているポリマーが挙げられる。
カチオン性堆積ポリマー及びアニオン性ポリアクリレートマイクロカプセルを、洗浄性界面活性剤とキャリアとを含むパーソナルクレンジング組成物に添加する前に混合し、プレミックスを形成する。
洗浄性組成物は、全て水相であっても、油相及び水相の両方を含んでもよい。1つの実施形態では、洗浄性組成物は油相及び水相の両方を有する。洗浄性組成物に添加された後、ポリアクリレートマイクロカプセルはこのような実施形態の水相に存在する。
A.洗浄性界面活性剤
本発明のパーソナルクレンジング組成物は、洗浄性界面活性剤を包含する。この洗浄性界面活性剤は、組成物にクリーニング性能を付与する。洗浄性界面活性剤は、アニオン性、非イオン性、カチオン性、双性イオン性、両性の界面活性剤、石鹸、又はこれらの組み合わせを含む。洗浄性界面活性剤の種々の例及び説明が、米国特許第6,649,155号;米国特許出願公開第12/103,902号;及び米国特許出願公開第2008/0206355号に記載されており、これらを参照のため本明細書に組み込む。
本発明の処方は、注入可能な液体(周囲条件下で)の形態であり得る。したがって、このような組成物は、典型的には水性キャリアを含み、これは約20%〜約95%、又は更には約60%〜約85%の濃度で存在する。水性キャリアは、水、又は水と有機溶媒との混和性混合物を含んでもよいが、1つの態様では、他の必須又は任意成分の微量成分として組成物中に付随的に組み込まれる場合を除き、最小限の有機溶媒を有するか、又は有意の濃度の有機溶媒を有さない水を含んでもよい。
本発明のパーソナルクレンジング組成物は、1)ポリアクリレートマイクロカプセルをアニオン性乳化剤でコーティングしてアニオン性ポリアクリレートマイクロカプセルを形成する工程と;2)このアニオン性ポリアクリレートマイクロカプセルをカチオン性堆積ポリマーと組み合わせてプレミックスを形成する工程と;3)このプレミックスを界面活性剤を含む洗浄性組成物及びキャリアに添加する工程と、を含むプロセスによって調製できる。
本発明のパーソナルクレンジング組成物は、リンスオフ製品又はリーブオン製品の形態であることができ、またクリーム、ゲル、エマルション、ムース及びスプレーを包含するがこれらに制限されない、多種多様な製品形態で配合することができる。
(1)試料をプレートに載せる。
(2)1度円錐とプレートとの間に1ミリメートルの隙間を設ける。
(3)流体上で0.01/秒〜10/秒の剪断掃引を実施する。
(4)流体上での剪断応力応答を記録する。
(5)各剪断速度における剪断応力の剪断速度に対する比を計算することによって流体のニート粘度を求める。
本出願の「試験方法」の項で開示される試験方法は、本出願人らの発明が本明細書に記載され及び特許請求されているように、本出願人らの発明のパラメータの各値を求めるために使用されるべきであると理解される。
「logPの計算値(calculated logP)」(ClogP)は、Hansch及びLeoのフラグメント手法により求められる(cf.A.Leo,Comprehensive Medicinal Chemistry,Vol.4,C.Hansch,P.G.Sammens,J.B.Taylor,and C.A.Ramsden,Eds.P.295,Pergamon Press,1990、参照により本明細書に組み込まれる)。ClogP値は、Daylight Chemical Information Systems Inc.(Irvine,California U.S.A.)から入手可能な「CLOGP」プログラムを用いることにより計算することができる。
沸点は、ASTM法D2887−04a「ガスクロマトグラフィーによる、石油留分の沸点範囲分布のための標準試験方法(Standard Test Method for Boiling Range Distribution of Petroleum Fractions by Gas Chromatography)」(ASTMインターナショナル)により測定される。
粒径は、Particle Sizing Systems(Santa Barbara CA)製のAccusizer 780Aを用いて測定する。装置は、Duke粒径標準を用いて0〜300μで較正される。粒径評価のための試料は、約1gのカプセルスラリーを約5gの脱イオン水中で希釈し、更に約1gのこの溶液を約25gの水中で希釈する工程によって調製される。
分析工程は以下を包含する:
a.)蒸留脱イオン(DI)水1Lの中に粒子1グラムを入れる。
b.)粒子をDI水の中に10分間にわたって留まらせておき、その後、60mL注射器フィルター、1.2ミクロンのニトロセルロースフィルター(Millipore、直径25mm)を使用して濾過により粒子を回収する。
c.)50個の個々の粒子の破裂力を決定する。粒子の破裂力を、Zhang,Z.;Sun,G;「Mechanical Properties of Melamine−Formaldehyde microcapsules,」J.Microencapsulation,vol 18,no.5,p.593〜602,2001に記載の手順を用いて決定する。次に、破裂力(ニュートン単位)を、対応する球状粒子(πr2、式中、rは、圧縮前の粒子の半径である)の断面積で除算することによって、各粒子の破壊強度を計算し、上記断面積は、実験装置及びZhang,Z.;Sun,G;「Mechanical Properties of Melamine−Formaldehyde microcapsules,」J.Microencapsulation,vol 18,no.5,p.593〜602,2001の方法を用いて、個々の各粒子の粒径を測定して決定する。
d.)上記c.)からの50個の独立した測定値を使用し、要求される範囲の破壊強度範囲内の破壊強度を有する粒子の百分率を計算する。
(1)機器仕様:Malvern Zeatasizer Nano Model ZEN3600試料セル、使い捨てキャピラリーセル(緑色のセル)。
(2)Duke標準を使用してPSDを測定し、それを使用してゼータ電位を測定して装置が正しく機能していることを確認する。
(3)DTS1060キャピラリーセルに1〜2mLのエタノール、続いてDI水を流してキャピラリーセルを準備する。
(4)試料調製:最初に、20mLのDI水を0.2ミクロンのフィルターで濾過して20mLバイアル瓶に入れる。このバイアル瓶に、1滴(50マイクロリットル)の30重量%固体微粒子懸濁液を添加し、微粒子懸濁液がバイアル瓶内に均質に分散するまで試料を静かに前後に反転する。次に、DTS1060の緑色の使い捨てゼータセルを1〜2mLのDI水ですすいだ後、注射器を用いて試料溶液をバイアル瓶からゼータセルに移し、セル内に気泡がないことを確認する。セルを上部まで満たした後、セルの出口及び入口にキャップをはめる(試料セル内に気泡がないことを再度確認する)。続いて、電極がシステム側を向くようにして、セルを試料チャンバに入れる。試料セルを装置に定置する。
(5)運転条件:
a.屈折率=1.35(この数値は懸濁液によって変わる場合がある。いずれの微粒子懸濁液の屈折率も屈折計を用いて測定できる。)
b.温度=摂氏25度
c.平衡時間=1分
d.ゼータ電位の計算に使用するスモルコフスキーモデル
(6)各試料をトリプリケートで測定する。装置からの結果は、外挿なしで、ミリボルト単位のゼータ電位として報告される。
75gの香油Scent A、75gのミリスチン酸イソプロピル、0.6gのDuPont Vazo−52、及び0.4gのDuPont Vazo−67からなる油剤を、1000rpmでの混合(4チップ、直径5.08cm(2”)、平らなミル刃)及び100cc/分での窒素ブランケット適用を行いながら、35℃に温度制御された鋼製ジャケット付反応器に加える。油剤を、45分間かけて75℃に加熱し、75℃で45分間維持し、75分間かけて60℃まで冷却する。
以下の例外を除き、実施例1と同一の材料、組成、及びプロセス条件でカプセルを製造する:油相の組成上の違いとして、1グラムのVazo−52、0.8グラムのVazo−67、0.3グラムの第三級ブチルアミノエチルメタクリレート、0.25グラムの2−カルボキシエチルアクリレート、及び12グラムのSartomer CN975;水相の組成上の違いとして、22グラムの25%活性Colloid 351、及び308グラムの水。その他の混合及びプロセス条件(process conditioner)は全て同じである。完成したマイクロカプセルは、10.7ミクロンの中央粒径、1.5の幅指数、及びマイナス60ミリボルトのゼータ電位、及び34.9重量%の総scent A濃度を有する。
以下の例外を除き、実施例1と同一の材料、組成、及びプロセス条件でカプセルを製造する:油相の組成上の違いとして、1グラムのVazo−52、0.8グラムのVazo−67、1.5グラムの第三級ブチルアミノエチルメタクリレート、1.2グラムの2−カルボキシエチルアクリレート、及び60グラムのSartomer CN975;水相の組成上の違いとして、68グラムの25%活性Colloid 351、及び282グラムの水。その他の混合及びプロセス条件(process conditioner)は全て同じである。完成したマイクロカプセルは、1.4ミクロンの中央粒径、1.2の幅指数、及びマイナス60ミリボルトのゼータ電位、及び20.7重量%の総scent A濃度を有する。
以下の例外を除き、実施例2と同一の材料、組成、及びプロセス条件でカプセルを製造する:油相の組成上の違いとして、1グラムの第三級ブチルアミノエチルメタクリレート、0.8グラムの2−カルボキシエチルアクリレート、及び40グラムのSartomer CN975;水相の組成上の違いとして、22グラムの25%活性Colloid 351、及び282グラムの水。その他の混合及びプロセス条件(process conditioners)は全て同じである。
実施例1、2、及び4のマイクロカプセルをボディクレンジング組成物に配合する。実施例2及び4のアニオン性マイクロカプセルを最初にタピオカデンプン(Akzo)の15重量%溶液と混合して粘弾性混合物を形成する:
・パフを流水下で5秒間飽和する。(35℃±15℃(95°F±5°F);約1.8L/min)
・前腕を流水下で5秒間、肘から手首まで濡らす。
・製品1mLを反対の手のひらに分与する。
・製品を、塗布した腕の上で5秒間摩擦する。手のひらを腕の縁に沿って摩擦し、過剰分を手のひらから取り除く。
・パフを再度濡らさないこと。前腕内側を、長い円を描くように10秒間軽く洗う。泡立つはずであり、すじ状になる場合には、圧力を弱める。
・15秒間の滞留時間放置する。
・前腕を流水で15秒間すすぐ。
・清浄な紙タオルを前腕にかぶせ、反対の手を内腕全体(肘から手首)に擦らずに動かすことによって、乾燥する。
・少なくとも30秒間は測定を実施せず、この間は腕を空気に晒しておく。
・異なる時間エージングした(及び周囲空気に晒した)腕について摩擦前及び摩擦後の腕の嗅覚性能を評価する。
Claims (15)
- パーソナルクレンジング組成物であって、
(a)0.001%〜10%の、アニオン性荷電ポリアクリレートマイクロカプセルと;
(b)0.01%〜2%のカチオン性堆積ポリマーと;
(c)2%〜50%の洗浄性界面活性剤と;
(d)キャリアと、を含む、パーソナルクレンジング組成物。 - 前記アニオン性荷電ポリアクリレートマイクロカプセルが、アニオン性乳化剤とポリアクリレートマイクロカプセルとを含む、請求項1に記載のパーソナルクレンジング組成物。
- 前記アニオン性乳化剤が、前記ポリアクリレートマイクロカプセルの外表面の少なくとも一部を取り囲むか、又は前記ポリアクリレートマイクロカプセルの外表面に物理的又は化学的に結合する、請求項2に記載のパーソナルクレンジング組成物。
- 前記アニオン性乳化剤及び前記ポリアクリレートマイクロカプセルは、前記アニオン性乳化剤の前記ポリアクリレートマイクロカプセルに対する重量比が1.0:40〜0.5:5になるように混合される、請求項2又は3に記載のパーソナルクレンジング組成物。
- 前記アニオン性荷電ポリアクリレートマイクロカプセル及び前記カチオン性堆積ポリマーは、前記アニオン性荷電ポリアクリレートマイクロカプセルの前記カチオン性堆積ポリマーに対する重量比が1.0:0.01〜1.0:10になるように混合される、請求項1〜4のいずれか一項に記載のパーソナルクレンジング組成物。
- 前記アニオン性乳化剤が、ポリ(メタ)アクリル酸;(メタ)アクリル酸とC1〜C22アルキルを有するその(メタ)アクリレートとのコポリマー;(メタ)アクリル酸と(メタ)アクリルアミドとのコポリマー;及びこれらの混合物からなる群から選択される、請求項1〜5のいずれか一項に記載のパーソナルクレンジング組成物。
- 前記アニオン性ポリアクリレートマイクロカプセルが、2ミクロン〜80ミクロンの粒径を有する、請求項1〜6のいずれか一項に記載のパーソナルクレンジング組成物。
- 前記ポリアクリレートマイクロカプセルが、コア及び前記コアを封入するシェルを有する、請求項1〜7のいずれか一項に記載のパーソナルクレンジング組成物。
- 前記コアが、6%〜99.9%の有益剤を含む、請求項1〜8のいずれか一項に記載のパーソナルクレンジング組成物。
- 前記カチオン性堆積ポリマーが、0.5ミリ当量/グラム〜12ミリ当量/グラムの電荷密度を有する水溶性ポリマーであり、前記カチオン性堆積ポリマーが100,000ダルトン〜5,000,000ダルトンの分子量を有する、請求項1〜9のいずれか一項に記載のパーソナルクレンジング組成物。
- 前記洗浄性界面活性剤が、アニオン性、非イオン性、カチオン性、双性イオン性、両性、石鹸、又はこれらの組み合わせである、請求項1〜10のいずれか一項に記載のパーソナルクレンジング組成物。
- 前記アニオン性荷電ポリアクリレートマイクロカプセルが、凝集体中に含有され、前記凝集体が、シリカ、クエン酸、炭酸ナトリウム、硫酸ナトリウム、塩化ナトリウム、及び結合剤、例えば、ケイ酸ナトリウム、変性セルロース、ポリエチレングリコール、ポリアクリレート、ポリアクリル酸、ゼオライト、及びそれらの混合物からなる群から選択される材料を含む、請求項1〜11のいずれか一項に記載のパーソナルクレンジング組成物。
- 前記パーソナルクレンジング組成物が、ゲルの形態であり、前記ゲルが45%未満の水を含む、請求項1〜12のいずれか一項に記載のパーソナルクレンジング組成物。
- 前記ゲルが1,000cps〜10,000cpsの未希釈粘度(neat viscosity)を有する、請求項13に記載のパーソナルクレンジング組成物。
- パーソナルクレンジング組成物の製造方法であって、
a)ポリアクリレートマイクロカプセルをアニオン性乳化剤でコーティングしてアニオン性ポリアクリレートマイクロカプセルを形成する工程と;
b)前記アニオン性ポリアクリレートマイクロカプセルをカチオン性堆積ポリマーと組み合わせて、プレミックスを形成する工程と;
c)前記プレミックスを、界面活性剤を含む洗浄性組成物及びキャリアに添加する工程と、を含む、方法。
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WO2012138710A2 (en) | 2012-10-11 |
EP2694017B1 (en) | 2019-05-22 |
JP6283607B2 (ja) | 2018-02-21 |
CN103458859A (zh) | 2013-12-18 |
WO2012138710A3 (en) | 2013-01-10 |
JP2014510142A (ja) | 2014-04-24 |
US20120276175A1 (en) | 2012-11-01 |
US9162085B2 (en) | 2015-10-20 |
EP2694017A2 (en) | 2014-02-12 |
MX2013010980A (es) | 2013-10-30 |
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