JP2004137199A - Powder coating agent, method for surface coating treatment, powder, and cosmetic containing the powder - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To obtain a powder coating agent capable of making a surface treatment of powder into powder with good stack feeling, moist feeling and water resistance. <P>SOLUTION: The powder coating agent consists of a 2-methacryloyloxyethyl phosphorylcholine copolymer represented by formula(1)( wherein, R<SP>1</SP>and R<SP>2</SP>are each H or methyl; (x) and (y) are proportions of constituent monomers in terms of total number of moles of the constituent monomers, respectively, and which meet the relationship: x/(x+y)=0.2-0.4 ) and having a weight-average molecular weight of 5,000-1,000,000. <P>COPYRIGHT: (C)2004,JPO

Description

【０００９】
（Ｒ^１及びＲ^２は、水素原子又はメチル基を示す。ｘ及びｙは構成単量体の合計モル数におけるそれぞれの構成単量体の割合を示し、ｘ／（ｘ＋ｙ）＝０．２〜０．４である。）
（２）前記（１）の粉体被覆剤により表面被覆処理された粉体。
（３）前記（１）の粉体被覆剤が、沸点が１２０℃以下のアルコール５〜６０重量％及び沸点が１２０℃以下の非極性有機溶剤４０〜９５重量％からなる混合溶媒に溶解した粉体被覆処理剤。
（４）前記（３）の粉体被覆処理剤に粉体を浸漬した後、溶媒を除去し乾燥することを特徴とする粉体の表面被覆処理法。
（５）前記（２）の粉体からなる調色粉体。
（６）前記（２）又は（５）の粉体を含有してなる化粧料。
（７）　前記（２）又は（５）の粉体を含有してなるメーキャップ化粧料。
【００１０】
【発明の実施の形態】
以下、本発明について詳しく述べる。
本発明の粉体被覆剤は、式（１）で示され、重量平均分子量が５，０００〜１，０００，０００である２−メタクリロイルオキシエチルホスホリルコリン共重合体からなる粉体被覆剤である。
【００１１】
ここで、式（１）中のＲ^１及びＲ^２は、水素原子又はメチル基を示す。また、Ｃ_１８Ｈ_３７基は、炭素数１８の飽和アルキル基を示し、例えば、ステアリル基、イソステアリル基が好ましく挙げられ、入手性等の理由から、ステアリル基が最も好ましく挙げられる。不飽和基を含む場合には、飽和アルキル基より安定性に劣るため、また、炭素数が１９以上のアルキル基の場合は、共重合体の製造を行う際、重合溶媒に対する溶解性が低下するため好ましくない。
【００１２】
また、本発明に用いられる２−メタクリロイルオキシエチルホスホリルコリン共重合体において、２−（メタ）アクリロイルオキシエチルホスホリルコリンに由来する構成単位（Ａ）とＣ_１８Ｈ_３７基を有する（メタ）アクリレートに由来する構成単位（Ｂ）の関係は、その合計モル数において、Ａの割合ｘとＢの割合ｙが、ｘ／（ｘ＋ｙ）が０．２〜０．４の関係になるよう選択される。尚、ｘ／（ｘ＋ｙ）が０．２未満の場合及び０．４を超える場合は、得られる粉体の耐水性及び保湿性が低くなるため好ましくない。更には、粉体の耐水性及び保湿性のバランスを保つためにｘ／（ｘ＋ｙ）は、０．２５〜０．３５であるのが好ましい。
【００１３】
本発明に用いる２−メタクリロイルオキシエチルホスホリルコリン共重合体は、２−（メタ）アクリロイルオキシエチルホスホリルコリンとステアリル（メタ）アクリレート又は／及びイソステアリル（メタ）アクリレートを混合して用い、これらを重合開始剤の存在下に、窒素、二酸化炭素、ヘリウム等で置換することにより不活性ガス雰囲気に保った反応器内でラジカル重合、例えば、塊状重合、懸濁重合、乳化重合、溶液重合等の公知の方法により共重合させることで調製することができる。前記ステアリル（メタ）アクリレートあるいはイソステアリル（メタ）アクリレートは単独で用いてもよいし、２種以上を混合して用いてもよい。
【００１４】
この際、使用できる重合開始剤としては、通常のラジカル重合開始剤であれば特に限定されず、例えば、過酸化ベンゾイル、過酸化ラウロイル、ジイソプロピルペルオキシジカーボネート、ｔ−ブチルペルオキシ−２−エチルヘキサノエート、ｔ−ブチルペルオキシピバレート、ｔ−ブチルペルオキシジイソブチレート、アゾビスイソブチロニトリル（ＡＩＢＮ）、アゾビスイソジメチルバレロニトリル、過硫酸塩及び過硫酸塩−亜硫酸水素塩系等を好ましく用いることができる。これらの重合開始剤の仕込量は、前記単量体組成物１００重量部に対して０．００１〜１０重量部が好ましく、更に０．０１〜５重量部が好ましい。
また、単量体組成物を共重合させるときの重合温度は−５０〜１５０℃、好ましくは２０〜１００℃であり、重合時間は０．５〜７２時間が好ましい。こうして得られる２−メタクリロイルオキシエチルホスホリルコリン共重合体の分子量は、重合温度、重合開始剤及び重合度調整剤等の使用量によっても異なるが、重量平均分子量で５，０００〜１，０００，０００、好ましくは、３０，０００〜１００，０００である。
【００１５】
本発明において２−メタクリロイルオキシエチルホスホリルコリン共重合体の重量平均分子量が、５，０００未満であると、粉体被膜剤が粉体表面から脱落し易くなるため好ましくない。また重合体の重量平均分子量が、１，０００，０００より大きいと溶媒への溶解性が極端に悪くなる。
【００１６】
本発明において、２−メタクリロイルオキシエチルホスホリルコリン共重合体からなる粉体被覆剤により粉体を表面被覆することで、目的の被覆粉体が提供される。前記粉体としては、大別して無機粉体と有機粉体を挙げることができる。前記無機粉体としては、任意の無機粉体を使用して良いが、例えば、ケイ酸、無水ケイ酸、ケイ酸マグネシウム、タルク、カオリン、雲母、セリサイト、ベントナイト、チタン被覆雲母、オキシ塩化ビスマス、酸化ジルコニウム、酸化マグネシウム、酸化亜鉛、酸化チタン、炭酸カルシウム、炭酸マグネシウム、酸化鉄、群青、紺青、酸化クロム、水酸化クロム、カラミン、ゼオライト等の無機粉体を、使用可能な無機粉体として好ましく挙げることができる。前記有機粉体としては、任意の有機粉体を使用して良いが、例えば、セルロース粉末、シルク粉末、ナイロン粉末、ポリエチレン粉末、ポリスチレン粉末、ポリプロピレン粉末等のほか、ポリアミド、ポリエステル、ポリエチレン、ポリプロピレン、ポリスチレン、ポリウレタン、ビニル樹脂、尿素樹脂、フェノール樹脂、フッ素樹脂、ケイ素樹脂、アクリル酸樹脂、メラミン樹脂、エポキシ樹脂、ポリカーボネート樹脂、ジビニルベンゼン―スチレン樹脂、セルロース樹脂等からなる有機粉体を好ましく挙げることができる。更に前記無機粉体及び有機粉体は、１種または２種以上を混合した粉体として使用することもできる。また、前記粉体の粒子径は１０ｎｍ〜１００μｍ程度が好ましい。
１０ｎｍ未満の粒径の粉体は、入手が困難であり、１００μｍより大きいの粒径の粉体は肌に対する感触が悪いため好ましくない。より好ましくは粒子径１００ｎｍ〜１０μｍのマイカ、セリサイト、ポリエチレン粉末、ポリプロピレン粉末の粉体を最も好ましく用いることができる。
【００１７】
本発明の粉体に対する粉体被覆剤の被覆量は、粉体の表面を充分に覆うことのできる量として設計されるが、好ましくは粉体１００重量部に対して０．０１重量部〜１０重量部、より好ましくは０．０１重量部〜１重量部の範囲である。
【００１８】
本発明の粉体被覆剤により表面被覆処理された粉体は、例えば、以下のように製造される。
沸点１２０℃以下のアルコールと沸点１２０℃以下の非極性有機溶剤との混合溶媒に、２−メタクリロイルオキシエチルホスホリルコリン共重合体を溶解し、得られた溶液に粉体を浸漬する。次に、該溶液から溶媒を除去し、粉体を乾燥する。より詳細には、本発明の粉体処理剤での表面被覆処理は、下記（Ａ）〜（Ｄ）の工程に分けることができる。
【００１９】
（Ａ）沸点１２０℃以下のアルコールと沸点１２０℃以下の非極性有機溶剤との混合溶媒に、本発明の粉体被覆剤である２−メタクリロイルオキシエチルホスホリルコリン共重合体を溶解し、粉体被膜処理剤を調整する。
（Ｂ）この粉体被覆処理剤に粉体を浸漬する。
（Ｃ）溶媒を除去する。
（Ｄ）粉体を乾燥させる。
【００２０】
前記（Ａ）の工程では、特定のアルコールと非極性有機溶剤との混合溶媒に、本発明の粉体被覆剤である２−メタクリロイルオキシエチルホスホリルコリン共重合体を溶解し、粉体被膜処理剤を調整する。
【００２１】
ここで、使用するアルコールは、沸点が１２０℃以下のアルコールである。具体的には、メタノール、エタノール、プロパノール、イソプロパノール、ペンチルアルコール、イソブチルアルコール、ｓ−ブチルアルコール、ｔ−ブチルアルコール及びこれらの混合物を挙げることができ、最も好ましくは、入手が容易であることからメタノール、エタノール、イソプロパノールが挙げられる。
【００２２】
また、使用する非極性有機溶剤は、沸点が１２０℃の非極性有機溶剤である。ここで、非極性有機溶剤とは、水酸基などの極性官能基を有しない溶剤の意味である。
非極性有機溶剤としては、炭化水素溶剤、エーテル溶剤、ケトン溶剤、エステル溶剤が挙げられる。具体的には、炭化水素溶剤としては、ｎ−ペンタン、イソペンタン、ｎ−ヘキサン、ｎ−ヘプタン、ｎ−オクタン、イソオクタン、ベンゼン、シクロヘキサン、メチルシクロヘキサン及びこれらの混合物を挙げることができる。またエーテル溶剤としては、エチルエーテル、イソプロピルエーテル、ジオキサン、テトラヒドロフラン、１，３−ジオキソラン、メチルｔ−ブチルエーテル及びこれらの混合物を挙げることができる。ケトン溶剤としては、アセトン、メチルエチルケトン、メチルイソブチルケトン及びこれらの混合物を挙げることができる。さらに、エステル溶剤としては、酢酸メチル、酢酸エチル、酢酸イソプロピル、酢酸イソブチル、酢酸プロピル及びこれらの混合物を挙げることができる。前記非極性有機溶剤において沸点が１２０℃より高い場合、本発明の粉体被覆剤で被覆した粉体を乾燥する際に時間がかかるため好ましくない。これらの非極性有機溶剤の中で、大量製造時の安全性や乾燥、脱臭性を考慮すると、ｎ−ヘキサン、アセトン、酢酸エチルがもっとも好ましく用いられる。
【００２３】
本発明において、粉体被膜処理剤の沸点が１２０℃以下のアルコール類と沸点が１２０℃以下の非極性有機溶剤との混合比は、２−メタクリロイルオキシエチルホスホリルコリン共重合体の溶解性及び被覆処理後の粉体の乾燥条件により適宜制御することが可能であるが、アルコールが５〜６０重量％、非極性有機溶剤４０重量％〜９５重量％であることが適している。アルコール濃度が５重量％未満、及び６０重量％より高い場合は、２−メタクリロイルオキシエチルホスホリルコリン共重合体の溶解性が低くなるので、好ましくない。
【００２４】
本発明において、粉体被膜処理剤中における２−メタクリロイルオキシエチルホスホリルコリン共重合体の濃度は、前記混合溶媒１００重量部に対して０．０１〜５重量部であることが望ましい。２−メタクリロイルオキシエチルホスホリルコリン共重合体の濃度が０．０１重量部未満では、粉体表面に均一に被覆することが難しいため好ましくない。また、２−メタクリロイルオキシエチルホスホリルコリン共重合体の濃度が５重量部より高い場合は、粉体の凝集が生じる理由から好ましくない。
混合溶媒に、２−メタクリロイルオキシエチルホスホリルコリン共重合体を好ましい濃度に溶解させる方法としては、例えば、混合溶媒に、２−メタクリロイルオキシエチルホスホリルコリン共重合体を添加し、攪拌、振とう、加熱、超音波照射などの通常の方法を用いることができるが、このようにして、２−メタクリロイルオキシエチルホスホリルコリン共重合体を混合溶媒に溶解させた粉体被覆処理剤を容易に製造することができる。
【００２５】
前記（Ｂ）の工程では、前記（Ａ）の工程で調製された粉体被膜処理剤中に、粉体を浸漬するが、この工程では、攪拌を行うのが望ましい。前記攪拌方法としては、一般に溶液を攪拌する装置であればいずれも使用可能であり、例えば攪拌羽根による攪拌機やディスパーザー、ホモミキサー等の分散機等を用いることができるが、好ましくは攪拌機を用いることができる。これを用いたときの好ましい撹拌条件としては、有機溶剤の蒸散の理由から加温条件下より室温下の条件で行うのが良い。
【００２６】
前記（Ｃ）の工程では、溶媒を除去するが、この工程における溶媒の除去方法としては、濾紙や濾布を用いた濾過による除去、遠心分離や粉体沈降後のデカンテーションによる除去、溶媒を揮発させる方法等を挙げることができ、好ましくは濾過による除去を用いることができる。これを用いたときの好ましい条件としては、溶媒の蒸散の理由から常圧または加圧の条件で行うのが良い。
【００２７】
前記（Ｄ）の工程では、粉体を乾燥させるが、この工程における粉体の乾燥方法としては、常圧や減圧下での乾燥、加熱による乾燥等を挙げることができる。乾燥方法としては、好ましくは減圧下での乾燥を用いることができる。これを用いたときの好ましい条件としては、短時間で溶媒を留去させるために、減圧下で加温した条件で行うのが良い。
【００２８】
以上のようにして、粉体を表面被覆処理できるが、得られた粉体は、通常知られる化粧料の中に、一般的に知られる方法により原料成分の一種として配合して用いることもできる。
例えば、本発明の表面被覆処理された粉体は、ファンデーション、頬紅、アイシャドウ、口紅、アイライナー、アイペンシル等のメーキャップ化粧料及びクリーム、乳液等のフェイシャル化粧料等に好ましく配合することができる。また、配合後の形態は、粉体状、ケーキ状、乳化状、オイル状、ゲル状等、いかなる形態であっても良く、どのような形態の化粧料であっても、幅広く配合することができる。
【００２９】
ここで、本発明の表面被覆処理された粉体の化粧料中への配合量は、粉体の全量中の０．００１〜１００重量％の範囲で適宜選択される。例えば、パウダー製品では１００重量％全てを、本発明の粉体被覆剤で被覆された粉体のみからなるように使用することもできる。また、本発明の粉体被覆剤で被覆された粉体を、乳化化粧料等に色付けする等の目的で使用する場合は０．００１重量％の添加で足りることがある。
【００３０】
本発明の表面被覆処理された粉体は、化粧料に通常用いられるシリコーン油、炭化水素油、エステル油等の中で良好な分散性を示す。特に主油剤がシリコーン油の場合に粉体の凝集が認められない。すなわち、シリコーン油を用いるような化粧料中に分散させる場合には相性がよいので、乳化化粧料の成分として有効である。分散媒として好ましいシリコーン油としては、ジメチルポリシロキサン、ジメチルシクロポリシロキサン、メチルフェニルポリシロキサン、メチルハイドロジェンポリシロキサン、ポリオキシアルキレン変性オルガノポリシロキサン、高級脂肪酸変性オルガノポリシロキサン、高級アルコール変性オルガノポリシロキサン、トリメチルシロキシシリケート等を挙げることができる。更には、前記シリコーン油の１種または２種以上の混合物に表面被覆処理された粉体を配合し、更にこれを用いて乳化化粧料とすることもできる。
【００３１】
本発明の表面被覆処理された粉体は、一般的に知られる方法により前記乳化化粧料に、原料成分の一種として配合して用いることができるが、その際、本発明の表面被覆処理された粉体を配合する乳化化粧料には、本発明の効果を損なわない範囲で、通常乳化化粧料に配合される他の成分を適宜配合しても良い。
【００３２】
例えば、乳化化粧料の水相成分として、プロピレングリコール、ジブロピレングリコール、１，３−ブチレングリコール、グリセリン、マルチトール、ソルビトール、ポリエチレングリコール、ヒアルロン酸ナトリウム、ピロリドンカルボン酸塩類等の保湿剤；油相成分として、ワセリン、ラノリン、セレシン、シリコーンワックス、マイクロクリスタリンワックス、カルナウバロウ、キャンデリラロウ、高級脂肪酸、高級アルコール等の固型・半固型油分、スクワラン、流動パラフィン、ポリブテン、ジメチルポリシロキサン、メチルフェニルポリシロキサン、エステル油、トリグリセライド等の流動油分；その他成分として、ビタミンＥ、ビタミンＥアセテート等の薬剤；収れん剤；酸化防止剤；防腐剤；香料；また、クエン酸、クエン酸ナトリウム、乳酸、乳酸ナトリウム、第２リン酸ナトリウム等のｐＨ調整剤；有機変性モンモリロナイト等の増粘剤；紫外線吸収剤；本発明の２−メタクリロイルオキシエチルホスホリルコリン共重合体からなる粉体被覆剤で被覆された粉体以外の無機及び有機粉体；本発明の製造方法以外の製造方法で製造した無機及び有機粉体；その他の粉体、無機及び有機顔料等を配合することができる。
【００３３】
【実施例】
以下実施例及び比較例により本発明を更に詳細に説明する。
合成例１　ＭＰＣ−ＳＭＡ共重合体（Ｐ−１）の合成
２−メタクリロイルオキシエチルホスホリルコリン（ＭＰＣと略す。）１３．５ｇとステアリルメタクリレート（ＳＭＡと略す。）３６．５ｇ、ラジカル重合開始剤としてアゾビスイソブチロニトリル（ＡＩＢＮと略す。）０．０１ｇとをブタノール４５０ｇに溶解し、重合用ガラス反応管に入れ窒素置換後、恒温槽にて５０℃で、７２時間重合させた。重合終了後、ブタノールを良溶媒として、ジエチルエーテルを貧溶媒として再沈殿精製を行い、加熱乾燥させて目的の共重合体を得た。分析結果を表１に示した。
【００３４】
合成例２　ＭＰＣ−ＩＭＡ共重合体（Ｐ−２）の合成
ＭＰＣを１３．５ｇとイソステアリルメタクリレート（ＩＭＡと略す。）３６．５ｇ、ラジカル重合開始剤としてＡＩＢＮ（０．０１ｇ）とをイソプロパノール（４５０ｇ）に溶解し、重合用ガラス反応管に入れ窒素置換後、恒温槽にて５０℃で、７２時間重合させた。重合終了後、イソプロパノールを良溶媒として、ジエチルエーテルを貧溶媒として再沈殿精製を行い、加熱乾燥させて目的の共重合体を得た。分析結果を表１に示した。
【００３５】
合成例３　ＭＰＣ−ＢＭＡ共重合体（Ｃ−１）の合成
ＭＰＣ（４５ｇ）、ｎ−ブチルメタクリレート（ＢＭＡと略す。）５ｇ、ラジカル重合開始剤としてＡＩＢＮ（０．０１ｇ）とをエタノール（４５０ｇ）に溶解し、重合用ガラス反応管に入れ窒素置換後、恒温槽にて５０℃で、７２時間重合させた。重合終了後、エタノールを良溶媒として、ジエチルエーテルを貧溶媒として再沈殿精製を行い、加熱乾燥させて目的の共重合体を得た。分析結果を表１に示した。
【００３６】
合成例４　ＭＰＣ単独重合体（Ｃ−２）の合成
ＭＰＣ（５０ｇ）、ラジカル重合開始剤としてＡＩＢＮ（０．０１ｇ）とをエタノール（４５０ｇ）に溶解し、重合用ガラス反応管に入れ窒素置換後、恒温槽にて５０℃で、７２時間重合させた。重合終了後、エタノールを良溶媒として、ジエチルエーテルを貧溶媒として再沈殿精製を行い、加熱乾燥させて目的の重合体を得た。分析結果を表１に示した。
【００３７】
合成例５　ＭＰＣ−ＳＭＡ共重合体（Ｃ−３）の合成
ＭＰＣ（４．５ｇ）とＳＭＡ（４５．５ｇ）、ラジカル重合開始剤としてＡＩＢＮ（０．０１ｇ）とをブタノール（４５０ｇ）に溶解し、重合用ガラス反応管に入れ窒素置換後、恒温槽にて５０℃で、７２時間重合させた。重合終了後、ブタノールを良溶媒として、ジエチルエーテルを貧溶媒として再沈殿精製を行い、加熱乾燥させて目的の重合体を得た。分析結果を表１に示した。
【００３８】
合成例６　ＭＰＣ−ＳＭＡ共重合体（Ｃ−４）の合成
ＭＰＣ（４４．５ｇ）とＳＭＡ（５．５ｇ）、ラジカル重合開始剤としてＡＩＢＮ（０．０１ｇ）とをブタノール（４５０ｇ）に溶解し、重合用ガラス反応管に入れ窒素置換後、恒温槽にて５０℃で、７２時間重合させた。重合終了後、ブタノールを良溶媒として、ジエチルエーテルを貧溶媒として再沈殿精製を行い、加熱乾燥させて目的の共重合体を得た。分析結果を表１に示した。
【００３９】
合成例７　ＭＰＣ−ＩＭＡ共重合体（Ｃ―５）の合成
ＭＰＣ（４．５ｇ）とＩＭＡ（４５．５ｇ）、ラジカル重合開始剤としてＡＩＢＮ（０．０１ｇ）とをイソプロパノール（４５０ｇ）に溶解し、重合用ガラス反応管に入れ窒素置換後、恒温槽にて５０℃で、７２時間重合させた。重合終了後、イソプロパノールを良溶媒として、ジエチルエーテルを貧溶媒として再沈殿精製を行い、加熱乾燥させて目的の共重合体を得た。分析結果を表１に示した。
【００４０】
合成例８　ＭＰＣ−ＩＭＡ共重合体（Ｃ−６）の合成
ＭＰＣ（２３．３ｇ）とＩＭＡ（２６．７ｇ）、ラジカル重合開始剤としてＡＩＢＮ（０．０１ｇ）とをイソプロパノール（４５０ｇ）に溶解し、重合用ガラス反応管に入れ窒素置換後、恒温槽にて５０℃で、７２時間重合させた。重合終了後、イソプロパノールを良溶媒として、ジエチルエーテルを貧溶媒として再沈殿精製を行い、加熱乾燥させて目的の共重合体を得た。分析結果を表１に示した。
【００４１】
【表１】

【００４２】
表１で用いた略号は次の通りである。
ＭＰＣ：２−メタクリロイルオキシエチルホスホリルコリン、
ＢＭＡ：ｎ−ブチルメタクリレート、
ＳＭＡ：ステアリルメタクリレート、
ＩＭＡ：イソステアリルメタクリレート、
ＡＩＢＮ：アゾビスイソブチロニトリル。
【００４３】
実施例１−１
イソプロパノール（５０重量％）／ｎ−ヘキサン（５０重量％）混合溶媒（２５０ｍＬ）中に、合成例１で合成したＰ−１（２．５ｇ）を加え、室温下に攪拌し溶解させた。次にマイカ（角八魚鱗箔（株）社製、マイカＲ−１０００）１００ｇをこれに加え、攪拌した後、吸引濾過し、粉体を取り出した。溶媒を８０℃のオーブン内で攪拌しながら留去し、表面被覆剤処理したマイカを得た。得られた表面被覆処理後のマイカについて以下のように粉体を評価した。
【００４４】
＜粉体の評価方法＞
粉体評価方法として、皮膚に対する感触を、スタック感（押し広げる時の感触）、シットリ感及び耐水性の３点で評価した（官能評価）。
（１）スタック感の評価基準
スタック感は、１名の専門官能試験者が全てのサンプルについて試験を行い、粉体５０ｍｇを左手の甲の上に乗せ、右手人差し指の腹で延ばした時の延び具合を、良い、ふつう、悪いの３段階に分類した。この時の評価は専門官能試験者の主観によって行い、「良い」を３点、「ふつう」を２点、「悪い」を１点としてスコアリングした。
（２）シットリ感の評価基準
シットリ感は、１名の専門官能試験者が全てのサンプルについて試験を行い、粉体５０ｍｇを左手の甲の上に乗せ、右手人差し指を用いて広げた際に感じる感覚を、良い、ふつう、悪いの３段階に分類した。この時の評価は専門官能試験者の主観によって行い、「良い」を３点、「ふつう」を２点、「悪い」を１点としてスコアリングした。
（３）耐水性の評価基準
耐水性は、１名の専門官能試験者が全てのサンプルについて試験を行い、粉体５０ｍｇを左手の甲の上に乗せ、右手人差し指を用いて広げた。次に粉体が広げられた皮膚表面に水道水（流量５０ｍＬ／分）を３分間接触させた。皮膚表面に残存する粉体量を目視により識別し、良い、ふつう、悪いの３段階に分類した。この時の評価は専門官能試験者の主観によって行い、「良い」を３点、「ふつう」を２点、「悪い」を１点としてスコアリングした。
その結果を表２に示した。尚、表２の総合評価については、「良い」を３点、「ふつう」を２点、「悪い」を１点としてスコアリングした。
【００４５】
実施例１−２
実施例１−１中のＰ−１の添加量２．５ｇを、０．２５ｇに代えた以外は、実施例１−１と同様に表面被覆処理し、粉体を評価した。結果を表２に示した。
【００４６】
実施例１−３
実施例１−１中のＰ−１の添加量２．５ｇを、０．０２５ｇに、また混合溶媒をメタノール（６０重量％）／ｎ−ヘキサン（４０重量％）に代えた以外は、実施例１−１と同様に表面被覆処理し、粉体を評価した。結果を表２に示した。
【００４７】
実施例１−４
実施例１−１中のＰ−１の添加量２．５ｇを、０．００２５ｇに、また有機混合溶媒をメタノール（６０重量％）／ｎ−ヘキサン（４０重量％）に代えた以外は、実施例１−１と同様に同様に表面被覆処理し、粉体を評価した。結果を表２に示した。
【００４８】
実施例１−５
エタノール（１０重量％）／ｎ−ヘキサン（６０重量％）／アセトン（３０重量％）混合溶媒（２５０ｍＬ）中に合成例２で合成したＰ−２（２．５ｇ）を加え、室温下に撹拌し溶解させた。次に、セリサイト（角八魚鱗箔（株）社製、エイトパール３００Ｓ）１００ｇを加えた。他は、実施例１−１と同様に表面被覆処理し、粉体を評価した。結果を表２に示した。
【００４９】
実施例１−６
実施例１−５中のＰ−２の添加量２．５ｇを、０．２５ｇに代えた以外は、実施例１−５と同様に表面被覆処理し、粉体を評価した。結果を表２に示した。
【００５０】
実施例１−７
合成例１−５中のＰ−２の添加量２．５ｇを０．０２５ｇに代え、混合溶媒をメタノール（５重量％）／酢酸エチル（９５重量％）とした以外は、実施例１−５と同様に表面被覆処理し、粉体を評価した。結果を表２に示した。
【００５１】
実施例１−８
合成例１−５中のＰ−２の添加量２．５ｇを０．００２５ｇに代え、混合溶媒をメタノール（５重量％）／酢酸エチル（９５重量％）とした以外は、実施例１−５と同様に表面被覆処理し、粉体を評価した。結果を表２に示した。
【００５２】
比較例１−１
被覆未処理のマイカ（角八魚鱗箔（株）社製、マイカＲ−１０００）１００ｇをそのまま用いて、粉体を評価をした。その結果を表３に示した。尚、表３の総合評価については、「良い」を３点、「ふつう」を２点、「悪い」を１点としてスコアリングした。
【００５３】
比較例１−２
エタノール（２５０ｍＬ）中に、合成例３で合成したＣ−１（２．５ｇ）を加え室温下に攪拌し溶解させた。次にマイカ（角八魚鱗箔（株）社製、マイカＲ−１０００）１００ｇをこれに加え、攪拌した後、吸引濾過し、粉体を取り出した。エタノールを８０℃のオーブン内で攪拌しながら留去し、表面被覆剤処理されたマイカを得た。得られた表面被覆剤処理後のマイカについて実施例１−１と同様にして粉体を評価した。結果を表３に示した。
【００５４】
比較例１−３
メタノール２５０ｍＬ中に、合成例４で合成したＣ−２（０．２５ｇ）を加え室温下に攪拌し溶解させた。次にマイカ（角八魚鱗箔（株）社製、マイカＲ−１０００）１００ｇをこれに加え、攪拌した後、吸引濾過し、粉体を取り出した。メタノールを８０℃のオーブン内で攪拌しながら留去し、表面被覆剤処理したマイカを得た。得られた表面被覆剤処理後のマイカについて実施例１−１と同様にして粉体を評価した。結果を表３に示した。
【００５５】
比較例１−４
合成例１で合成したＰ−１（２．５ｇ）の代わりに、合成例５で合成したＣ−３（０．２５ｇ）を用いた以外は、実施例１−１と同様に表面被覆処理し、粉体を評価した。結果を表３に示した。
【００５６】
比較例１−５
合成例１で合成したＰ−１（２．５ｇ）の代わりに、合成例６で合成したＣ−４（０．２５ｇ）を用いた以外は、実施例１−１と同様に表面被覆処理し、粉体を評価した。結果を表３に示した。
【００５７】
比較例１−６
被覆未処理のセリサイト（角八魚鱗箔（株）社製、エイトパール３００Ｓ）、１００ｇをそのまま用いて、実施例１−１と同様に、粉体を評価した。結果を表３に示した。
【００５８】
比較例１−７
マイカ（１００ｇ）の代わりに、セリサイト（角八魚鱗箔（株）社製、エイトパール３００Ｓ）１００ｇを用いた以外は、比較例１−２と同様に表面被覆処理し、粉体を評価した。結果を表３に示した。
【００５９】
比較例１−８
マイカ（１００ｇ）の代わりに、セリサイト（角八魚鱗箔（株）社製、エイトパール３００Ｓ）１００ｇを用いた以外は、比較例１−３と同様に表面被覆処理し、粉体を評価した。結果を表３に示した。
【００６０】
比較例１−９
マイカ（１００ｇ）の代わりに、セリサイト（角八魚鱗箔（株）社製、エイトパール３００Ｓ）１００ｇを用いた以外は、比較例１−４と同様に表面被覆処理し、粉体を評価した。結果を表３に示した。
【００６１】
比較例１−１０
マイカ（１００ｇ）の代わりに、セリサイト（角八魚鱗箔（株）社製、エイトパール３００Ｓ）１００ｇを用いた以外は、全て比較例１−５と同様に表面被覆処理し、粉体を評価した。結果を表３に示した。
【００６２】
【表２】

【００６３】
【表３】

以上、実施例１−１〜１−８、比較例１−１〜１−１０の結果より、本発明の表面被覆処理後の粉体は、スタック感が良く、シットリ感及び耐水性に優れていることがわかった。
【００６４】
実施例２−１
イソプロパノール（５０重量％）／ｎ−ヘキサン（５０重量％）混合溶媒（１Ｌ）中に合成例１で合成したＰ−１（３ｇ）を加え、室温下に攪拌して溶解させた。次にタルク（竹原化学工業株式会社製）９９７ｇを加えディスパーザーで分散した後、ニーダーに入れ、攪拌しながら減圧し、混合溶媒を除去して表面被覆処理したタルクを得た。得られた表面被覆処理後のタルクについて、皮膚に付着させて目視にて観察したところ、表面被覆処理後のタルクは、滑らかな伸びを持ち、密着性が良く、シットリとした使用感で、且つ、水に浮かべても沈降せず、撥水性に優れる性質を有していた。これにより、タルクを用いても、マイカやセリサイトと同様に、表面被覆処理できることが確認できた。
【００６５】
実施例２−２
メタノール（６０重量％）／ｎ−ヘキサン（４０重量％）混合溶媒（１Ｌ）中に合成例２で合成したＰ−２（５ｇ）を加え、室温下に攪拌して溶解させた。次に、微粒子酸化チタン（テイカ株式会社、ＭＴ５００）９９５ｇを加えディスパーザーで分散した後、ニーダーに入れ攪拌しながら減圧し、混合溶媒を除去して表面被覆処理した微粒子酸化チタンを得た。得られた表面被覆処理後の微粒子酸化チタンについて、皮膚に付着させて目視にて観察したところ、表面被覆処理後の微粒子酸化チタンは、滑らかな伸びを持ち、密着性が良く、シットリとした使用感で且つ、水に浮かべても沈降せず、撥水性に優れる性質を有していた。これにより、被覆微粒子酸化チタンを用いても、マイカやセリサイトと同様に、表面被覆処理できることが確認できた。
【００６６】
実施例３−１
表４に示す配合量にてＸ成分をへンシェルミキサーに秤り込み、高速で２分間混合し、調色粉体（１００ｇ）を得た。これを、あらかじめエタノール（１０重量％）／ｎ−ヘキサン（６０重量％）／アセトン（３０重量％）混合溶媒にＹ成分（合成例１で合成したＰ−１）を０．０１重量％の濃度になるように溶解させて調製した溶液（１００ｍＬ）中に浸漬し、攪拌した後、吸引ろ過し、粉体を取り出した。混合溶媒を８０℃のオーブン内で攪拌しながら留去し、１ｍｍヘリングボーン・スクリーン装着パルベライザーで粉砕したのち、混合し、表面被覆処理した調色粉体（１００ｇ）を調製した。
【００６７】
実施例３−２
表４に示す配合量にてＸ成分をへンシェルミキサーに秤り込み、高速で２分間混合し、調色粉体（１００ｇ）を得た。これを、あらかじめエタノール（１０重量％）／ｎ−ヘキサン（６０重量％）／アセトン（３０重量％）混合溶媒にＹ成分（合成例１で合成したＰ−１）を０．１重量％の濃度になるように溶解させて調製した溶液（１００ｍＬ）中に浸漬し、攪拌した後、吸引ろ過し、粉体を取り出した。混合溶媒を８０℃のオーブン内で攪拌しながら留去し、１ｍｍヘリングボーン・スクリーン装着パルベライザーで粉砕，混合し、表面被覆処理した調色粉体（１００ｇ）を調製した。
【００６８】
実施例３−３
表４に示す配合量にてＸ成分をへンシェルミキサーに秤り込み、高速で２分間混合し、調色粉体（１００ｇ）を得た。これを、あらかじめメタノール（５重量％）／酢酸エチル（９５重量％）混合溶媒にＹ成分（合成例１で合成したＰ−２）を０．１重量％の濃度になるように溶解させて調製した溶液（１００ｍＬ）中に浸漬し、攪拌した後、吸引ろ過し、粉体を取り出した。混合溶媒を８０℃のオーブン内で攪拌しながら留去し、１ｍｍヘリングボーン・スクリーン装着パルベライザーで粉砕したのち、混合し、表面被覆処理した調色粉体（１００ｇ）を調製した。
【００６９】
参考例１
表４に示す配合量にてＸ成分をへンシェルミキサーに秤り込み、高速で２分間混合した。その後、１ｍｍヘリングボーン・スクリーン装着パルベライザーで粉砕し、比較のための調色粉体（１００ｇ）を調製した。
【００７０】
【表４】

【００７１】
実施例４−１〜４−３
Ａ成分あるいはＣ成分を表５に示す配合量にて混合した。次に、それぞれを８０℃で加熱溶解した。Ａ成分にＢ成分（実施例３−１〜３−３で表面被覆処理した各種粉体）を加えミキサーで混合し、さらに、これにＣ成分を徐々に加えて乳化したのち、攪拌しながら冷却してファンデーション（１００ｇ）を得た。
【００７２】
比較例２
Ａ成分あるいはＣ成分を表５に示す配合量にて混合した。次に、それぞれを８０℃で加熱溶解した。Ａ成分にＢ成分（参考例１で調製した粉体）を加えミキサーで混合し、さらに、これにＣ成分を徐々に加えて乳化したのち、攪拌しながら冷却してファンデーション（１００ｇ）を得た。
【００７３】
実施例５
実施例４−１〜４−３及び比較例２で調製したファンデーションを用いて、専門パネラー１０名により使用特性を評価した。評価方法は右半顔に実施例４−１〜４−３のファンデーションを塗布し、左半顔に比較例２のファンデーションを塗布して、比較例２のファンデーションを基準にして、右半顔に塗布したファンデーションの「シットリ感」、「化粧映え」、「密着性」について官能評価し、更に化粧５時間後の評価として「化粧持ち」の合計４項目について官能評価を行った。使用感のそれぞれの項目について比較例２のファンデーションと比較して、「３点：比較例より良い」、「２点：比較例と同等」、「１点：比較例の方が良い」の３段階で、専門パネラー１０名の主観により官能評価し、各項目につき１０名の平均点数を算出して評価結果とした。この結果を表５の官能評価の欄に示した。
【００７４】
【表５】

【００７５】
以上の結果より、実施例４−１〜４−３の本発明のファンデーションは、表面被覆処理していない粉体を含むファンデーションに比較し、いずれも優れた化粧効果を有する。特に、シットリ感について見てみると、実施例４−１〜４−３ともに比較例２に比較して著しく改善されることにも注目すべきであり、これは本発明の粉体被覆剤である２−メタクリロイルオキシエチルホスホリルコリン共重合体が保湿性に優れるためであり、これによる表面被覆処理の効果が明らかである。
【００７６】
実施例６
メタノール（６０重量％）／ｎ−ヘキサン（４０重量％）混合溶媒（１Ｌ）に、合成例１で合成したＰ−１（　３ｇ）を加え、室温下に攪拌して溶解した。これに、タルク（小堺製薬（株）社製、タルク）２１．４重量部、セリサイト（角八魚鱗箔（株）社製、エイトパール３００Ｓ）４０重量部、マイカ（角八魚鱗箔（株）社製、マイカＲ−１０００）３０重量部、酸化チタン（チタン工業（株）社製、クロノス酸化チタンＫＡ−１０）６重量部、黄酸化鉄（チタン工業（株）社製、クロックス）２重量部、べンガラ（チタン工業（株）社製、マピコ合成酸化鉄Ｒ−５１６−Ｌ）０．５重量部、黒酸化鉄（チタン工業（株）社製、マピコ合成酸化鉄ＢＬ−１００）０．１重量部を混合して全量９９７ｇとした混合粉体を加えた。へンシェルミキサーにて均一混合しディスパーで分散した後、ニーダーに入れ攪拌しながら滅圧し、混合溶媒を除去して表面被覆処理後の混合粉体を得た。表面被覆処理した混合粉体は滑らかな伸びに拘わらず、密着性が良く、シットリとした使用感で且つ、水に浮かべても沈降せず、撥水性に優れる性質を有していた。
【００７７】
参考例２
タルク（小堺製薬（株）社製、タルク）２１．４重量部、セリサイト（角八魚鱗箔（株）社製、エイトパール３００Ｓ）４０重量部、マイカ（角八魚鱗箔（株）社製、マイカＲ−１０００）３０重量部、酸化チタン（チタン工業（株）社製、クロノス酸化チタンＫＡ−１０）６重量部、黄酸化鉄（チタン工業（株）社製、クロックス）２重量部、ベンガラ（チタン工業（株）社製、マピコ合成酸化鉄Ｒ−５１６−Ｌ）０．５重量部、黒酸化鉄（チタン工業（株）社製、マピコ合成酸化鉄ＢＬ−１００）０．１重量部を秤量し、全量５００ｇとした粉体をヘンシェルミキサーにて均一混合して混合粉体を得た。
【００７８】
参考例３
タルク（小堺製薬（株）社製、タルク）２１．４重量部、セリサイト（角八魚鱗箔（株）社製、エイトパール３００Ｓ）４０重量部、マイカ（角八魚鱗箔（株）社製、マイカＲ−１０００）３０重量部、酸化チタン（チタン工業（株）社製、クロノス酸化チタンＫＡ−１０）６重量部、黄酸化鉄（チタン工業（株）社製、クロックス）２重量部、べンガラ（チタン工業（株）社製、マピコ合成酸化鉄Ｒ−５１６−Ｌ）０．５重量部、黒酸化鉄（チタン工業（株）社製、マピコ合成酸化鉄ＢＬ−１００）０．１重量部を秤量し、全量４９０ｇとした粉体をへンシェルミキサーにて混合しながら、メチルハイドロジェンポリシロキサン１０ｇをゆっくり添加し、全体を均一にした。その後、混合物を２００℃の雰囲気で４時間放置し、更に冷却してシリコン焼付処理混合粉体を得た。
【００７９】
実施例７−１
表６に示す配合量で原料成分を配合し、ヘンシェルミキサーを用いて混合粉砕した後、プレス成型して固型状ファンデーションを得た。このファンデーションは水有りで使用しても、水なしで使用してもケーキング（表面が油光りしてスポンジ等にとれなくなること）せず、密着性と耐水性に優れ、化粧崩れしにくく、シットリとした感触が持続し、良好な使用感触を有していた。
【００８０】
比較例３−１
表６に示す配合量で原料成分を配合し、ヘンシェルミキサーを用いて混合粉砕した後、プレス成型して固型状ファンデーションを得た。このファンデーションは、水なしで使用するときは良好な使用性を示すが、水有りで使用すると経時でケーキが固くなり、ケーキングを起こした。また、耐水性を有しておらず、化粧の持続性に欠けていた。
【００８１】
比較例３−２
表６に示す配合量で原料成分を配合し、ヘンシェルミキサーを用いて混合粉砕した後、プレス成型して固型状ファンデーションを得た。このファンデーションは、水有りで使用しても、水なしで使用してもケーキングせず、耐水性も優れていたが、肌がかさつきやすく、保湿性に欠けていた。
【００８２】
【表６】

【００８３】
以上、実施例７−１及び比較例３−１、３−２の結果から、未処理粉体やシリコン焼付処理粉体に比較し、本発明の表面被覆処理した粉体を配合すると、密着性と耐水性に優れ且つシットリ感を有するファンデーションを提供できることがわかった。
【００８４】
実施例８−１
イソプロパノール（５０重量％）／ｎ−ヘキサン（５０重量％）混合溶媒（２５０ｍＬ）中に、合成例１で合成したＰ−１（０．２５ｇ）を加え、室温下に攪拌し溶解させた。次に、酸化チタン（チタン工業（株）社製、クロノス酸化チタンＫＡ−１０）１００ｇを加え、攪拌した後、吸引濾過し、粉体を取り出した。溶媒を８０℃のオーブン内で攪拌しながら留去し、表面被覆処理した酸化チタンを得た。
【００８５】
実施例８−２
酸化チタンを酸化鉄黄（チタン工業（株）社製、クロックス）１００ｇに代えた以外は、実施例８−１と同様に処理し、表面被覆処理した酸化鉄黄を得た。
実施例８−３：Ｐ−１被覆酸化鉄赤の調製
酸化チタンを酸化鉄赤（チタン工業（株）社製、マピコ合成酸化鉄Ｒ−５１６−Ｌ）１００ｇに変更した以外は、実施例８−１と同様に処理し、表面被覆処理した酸化鉄赤を得た。
【００８６】
実施例８−４
酸化チタンをセリサイト（角八魚鱗箔（株）社製、エイトパール３００Ｓ）１００ｇに代えた以外は、実施例８−１と同様に処理し、表面被覆処理したセリサイトを得た。
実施例８−５
酸化チタンを酸化鉄黒（チタン工業（株）社製、マピコ合成酸化鉄ＢＬ−１００）１００ｇに代えた以外は、実施例８−１と同様に処理し、表面被覆処理した酸化鉄黒を得た。
【００８７】
実施例８−６
酸化チタンを微粒子酸化チタン（テイカ（株）社製、微粒子チタンＭＴ１００Ｔ）１００ｇに代えた以外は、実施例８−１と同様に処理し、表面被覆処理した微粒子酸化チタンを得た。
実施例８−７
酸化チタンをカオリン（土屋カオリン工業（株）社製、カオリンＪＰ−１００）１００ｇに代えた以外は、実施例８−１と同様に処理し、表面被覆処理したカオリンを得た。
【００８８】
実施例８−８
酸化チタンを酸化亜鉛（堺化学工業（株）社製、ＺＩＮＣＡ−２０）１００ｇに代えた以外は、実施例８−１と同様に処理し、表面被覆処理した酸化亜鉛を得た。
実施例８−９
酸化チタンを粉末化したチタン酸コバルト（日興リカ（株）社製、ファインセラＧ−Ｎ−１）１００ｇに代えた以外は、実施例８−１と同様に処理し、表面被覆処理したチタン酸コバルトを得た。
【００８９】
参考例４−１
合成例１で合成したＰ−１の代わりに、合成例４で合成したＣ−２を用いた以外は、実施例８−１と同様に処理し、表面被覆処理した酸化チタンを得た。
参考例４−２
合成例１で合成したＰ−１の代わりに、合成例４で合成したＣ−２を用いた以外は、実施例８−４と同様に処理し、表面被覆処理したセリサイトを得た。
【００９０】
参考例４−３
合成例１で合成したＰ−１の代わりに、合成例４で合成したＣ−２を用いた以外は、実施例８−２と同様に処理し、表面被覆処理した酸化鉄黄を得た。
参考例４−４
合成例１で合成したＰ−１の代わりに、合成例４で合成したＣ−２を用いた以外は、実施例８−６と同様に処理し、表面被覆処理した微粒子酸化チタンを得た。
【００９１】
参考例４−５
合成例１で合成したＰ−１の代わりに、合成例４で合成したＣ−２を用いた以外は、実施例８−９と同様に処理し、表面被覆処理したチタン酸コバルトを得た。
【００９２】
実施例９
表７に示す原料成分を配合し、混合粉砕後プレス成型して固形状プラッシャーを得た。得られたプラッシャーは密着性と耐水性に優れ化粧崩れしにくく、シットリとした感触が持続し、良好な使用感触を有していた。
【００９３】
【表７】

【００９４】
実施例１０
表８に示す成分を配合し混合して、ファンデーションを得た。得られたファンデーションは密着性と耐水性に優れ、化粧崩れしにくく、シットリとした感触が持続し、良好な使用感触を有していた。
【００９５】
【表８】

【００９６】
実施例１１
表９に示した実施例１１の配合量にて、まず加熱溶解したＢ成分中にＣ成分を添加し、分散させた。次にあらかじめ加温したＡ成分中にこれを添加し乳化して化粧下地を得た。得られた化粧下地はファンデーションとの密着性が良く、化粧崩れしにくく、更に、シットリとした感触が持続し、良好な使用感触を有していた。
【００９７】
比較例４
表９に示した参考例５の配合量にて、まず加熱溶解したＢ成分中にＣ成分を添加し、分散させた。次にあらかじめ加温したＡ成分中にこれを添加し乳化して化粧下地を得た。得られた化粧下地は、シットリとした感触は有するが、化粧崩れを起こしやすかった。
【００９８】
【表９】

【００９９】
実施例１２
表１０に示す配合量でＡ成分をヘンシェルミキサーで均一混合して混合粉体を得た。次にイソプロパノール（５０重量％）／ｎ−ヘキサン（５０重量％）混合溶媒（２５０ｍＬ）中に、合成例１で合成したＰ−１（２．５ｇ）を加え室温下に攪拌し溶解させ、更に、先に調製した混合粉体を加え、攪拌した後、吸引濾過し、粉体を取り出した。溶媒を８０℃のオーブン内で攪拌しながら留去し表面被覆処理した混合粉体を得た。次に、表１０に示す配合量で、被覆処理した混合粉体と、これと別に均一混和したＣ成分をヘンシェルミキサーにて均一混合した。これを粉砕機にて粉砕し、メッシュを通して粒度を揃え、金皿に圧縮成型してアイシャドウを得た。
得られたアイシャドウは滑らかな伸びで密着性が良く、シットリとした使用感で、化粧持ちに優れていた。
【０１００】
【表１０】

【０１０１】
実施例１３
表１１に示す配合量でＡ成分をヘンシェルミキサーで均一混合して混合粉体を得た。次にイソプロパノール（５０重量％）／ｎ−ヘキサン（５０重量％）混合溶媒（２５０ｍＬ）中に、合成例１で合成したＰ−１（２．５ｇ）を加え室温下に攪拌し溶解させ、更に、先に調製した混合粉体を加え、攪拌した後、吸引濾過し、粉体を取り出した。溶媒を８０℃のオーブン内で攪拌しながら留去し表面被覆処理した混合粉体を得た。次に、表１１に示す配合量で、被覆処理した混合粉体にＣ成分を加えてヘンシェルミキサーにて均一混合し、Ｄ成分を順次加えて均一混合した。これを粉砕機にて粉砕し、メッシュを通して容器に入れ、フェイスパウダーを得た。
得られたフェイスパウダーは滑らかな伸びで、シットリとした使用感で、化粧崩れを起こしにくかった。
【０１０２】
【表１１】

【０１０３】
【発明の効果】
本発明の粉体被覆剤によれば、粉体をスタック感が良く、シットリ感及び耐水性に優れた粉体に表面処理することができる。
本発明の粉体被覆剤により処理された粉体は、スタック感が良く、シットリ感及び耐水性に優れている。したがって、耐水性でありながら優れた保湿性をも有する化粧用粉体を提供することができる。
本発明の粉体の表面被覆処理法によれば、温和で環境に優しい条件下で、粉体表面に均一に被覆するための方法を提供することができる。
本発明の表面被覆処理された粉体を含有してなる化粧料は、シットリ感、使用感、化粧映え、密着性に優れており、また化粧持ちに優れた化粧料である。[0001]
TECHNICAL FIELD OF THE INVENTION
The present invention relates to a powder coating. The present invention also relates to a powder surface coating method using the same. Furthermore, the present invention relates to a surface-coated powder and a cosmetic containing the powder.
[0002]
[Prior art]
In general, inorganic powders and organic powders have different surface states depending on their types, and exist in a wide range from hydrophilic and good in water dispersibility to lipophilic and good in oil dispersibility. When inorganic powders or organic powders are blended in cosmetics, especially makeup cosmetics, (1) it has a large specific gravity and lacks dispersion stability, and (2) the coating color changes over time due to sebum or sweat. And (3) lack of affinity with the skin.
[0003]
In order to solve these technical problems, for example, hydrophilic treatment by coating with inorganic phosphate, etc., lipophilic treatment by coating oil, hydrophobic treatment by baking organic silicone, etc. It is generally used as a processing method. However, the above-mentioned treatment method has a drawback that the surface modifier is likely to fall off and the expected effect is not obtained, the dosage form that can be blended is limited, and the desired physical properties cannot be obtained.
In addition, since powder easily absorbs lipids and moisture on the skin, applying a foundation or the like has a drawback that the skin becomes bulky, which has been a major problem in use. In particular, hydrophobized powders obtained by baking organic silicones, which are widely used in two-way foundations, are unlikely to cause makeup collapse, but tend to be powdery and tend to bulk up the skin. In order to solve these problems, an inorganic powder having water resistance and moisture retention has been required.
On the other hand, the organic powder has a drawback that the surface is hydrophobic, so that it has no moisturizing property and the skin becomes bulky in a dry season or the powder floats. In order to solve these problems, it has been proposed to coat with metal soap, water-soluble collagen, cellulose derivative and the like, but it was not sufficient.
[0004]
To solve the above problem, use of a cosmetic powder coated with a 2-methacryloyloxyethyl phosphorylcholine polymer has been disclosed (see Patent Document 1). However, the polymer disclosed in Patent Document 1 is a homopolymer of 2-methacryloyloxyethyl phosphorylcholine, a copolymer with (meth) acrylate having 1 to 10 carbon atoms, or a copolymer with styrene. Such a polymer containing 2-methacryloyloxyethyl phosphorylcholine did not have sufficient water resistance when coated with an inorganic powder. In the case of coating with an organic powder, the above problems could not be completely solved because of low adhesion to the powder.
Therefore, in the cosmetics containing the powder for cosmetics coated with the polymer containing 2-methacryloyloxyethyl phosphorylcholine described in Patent Document 1, there is a problem in makeup collapse, moisturizing the skin, and maintaining the performance for a long time. Was.
Further, Patent Document 1 discloses a method of coating a powder containing a polymer containing 2-methacryloyloxyethyl phosphorylcholine with mechanokamicel, and a method of spraying the powder. However, in the coating method using mechanochemical, the polymer to be coated is decomposed to reduce the molecular weight, and decomposition of the phosphorylcholine group occurs. For this reason, the powder described in Patent Document 1 has a problem that the polymer is easily peeled off, and it is difficult to obtain desired physical properties. Further, in the spraying method described in Patent Literature 1, it is difficult to uniformly coat the powder surface, so that there is a problem that the difference between lots is large and the quality is not stable. There has been a new demand for a treatment method capable of uniformly coating the surface of an inorganic powder with a 2-methacryloyloxyethyl phosphorylcholine-containing copolymer.
[0005]
[Patent Document 1]
JP-A-7-118123 (pages 1-4)
[0006]
[Problems to be solved by the invention]
An object of the present invention is to provide a powder coating agent that can be surface-treated into a powder having a good stack feeling, a good sit feeling, and excellent water resistance.
Another object of the present invention is to provide a powder surface coating method for uniformly coating the powder surface with a powder coating agent under mild and environmentally friendly conditions.
It is another object of the present invention to provide a cosmetic composition which is excellent in a feeling of fit, a feeling of use, a shine of cosmetics, and an adhesive property, and which is excellent in durability.
[0007]
[Means for Solving the Problems]
The present invention is described below.
(1) A powder coating comprising a 2-methacryloyloxyethyl phosphorylcholine copolymer represented by the following formula (1) and having a weight average molecular weight of 5,000 to 1,000,000.
[0008]
Embedded image

[0009]
(R ¹ And R ² Represents a hydrogen atom or a methyl group. x and y show the ratio of each constituent monomer in the total number of moles of the constituent monomer, and x / (x + y) = 0.2 to 0.4. )
(2) A powder surface-coated with the powder coating agent of (1).
(3) A powder obtained by dissolving the powder coating agent of the above (1) in a mixed solvent comprising 5 to 60% by weight of an alcohol having a boiling point of 120 ° C or lower and 40 to 95% by weight of a nonpolar organic solvent having a boiling point of 120 ° C or lower. Body coating treatment agent.
(4) A method of coating a surface of a powder, comprising immersing the powder in the powder coating treating agent of the above (3), removing the solvent, and drying.
(5) Toning powder comprising the powder of (2).
(6) A cosmetic comprising the powder of (2) or (5).
(7) A makeup cosmetic containing the powder of (2) or (5).
[0010]
BEST MODE FOR CARRYING OUT THE INVENTION
Hereinafter, the present invention will be described in detail.
The powder coating of the present invention is a powder coating composed of a 2-methacryloyloxyethyl phosphorylcholine copolymer represented by the formula (1) and having a weight average molecular weight of 5,000 to 1,000,000.
[0011]
Here, R in the equation (1) ¹ And R ² Represents a hydrogen atom or a methyl group. Also, C ₁₈ H ₃₇ The group represents a saturated alkyl group having 18 carbon atoms, for example, preferably a stearyl group and an isostearyl group, and most preferably a stearyl group from the viewpoint of availability and the like. When an unsaturated group is contained, the stability is lower than that of a saturated alkyl group. In the case of an alkyl group having 19 or more carbon atoms, the solubility in a polymerization solvent is reduced when a copolymer is produced. Therefore, it is not preferable.
[0012]
In the 2-methacryloyloxyethyl phosphorylcholine copolymer used in the present invention, the structural unit (A) derived from 2- (meth) acryloyloxyethyl phosphorylcholine and C ₁₈ H ₃₇ Regarding the relationship between the structural units (B) derived from the (meth) acrylate having a group, in the total mole number, the ratio x of A and the ratio y of B are such that x / (x + y) is 0.2 to 0.4. Selected to be in a relationship. When x / (x + y) is less than 0.2 or more than 0.4, the water resistance and moisture retention of the obtained powder are undesirably low. Further, x / (x + y) is preferably from 0.25 to 0.35 in order to maintain the balance between water resistance and moisture retention of the powder.
[0013]
The 2-methacryloyloxyethyl phosphorylcholine copolymer used in the present invention is a mixture of 2- (meth) acryloyloxyethyl phosphorylcholine and stearyl (meth) acrylate and / or isostearyl (meth) acrylate, and these are used as polymerization initiators. In the presence of nitrogen, carbon dioxide, radical polymerization in a reactor kept in an inert gas atmosphere by replacing with helium, etc., known methods such as bulk polymerization, suspension polymerization, emulsion polymerization, solution polymerization, etc. Can be prepared by copolymerizing The stearyl (meth) acrylate or isostearyl (meth) acrylate may be used alone or in combination of two or more.
[0014]
At this time, the polymerization initiator that can be used is not particularly limited as long as it is a normal radical polymerization initiator. For example, benzoyl peroxide, lauroyl peroxide, diisopropylperoxydicarbonate, t-butylperoxy-2-ethylhexano Ethate, t-butyl peroxypivalate, t-butyl peroxydiisobutyrate, azobisisobutyronitrile (AIBN), azobisisodimethylvaleronitrile, persulfate, and persulfate-bisulfite are preferably used. be able to. The amount of these polymerization initiators to be charged is preferably 0.001 to 10 parts by weight, more preferably 0.01 to 5 parts by weight, based on 100 parts by weight of the monomer composition.
Further, the polymerization temperature at the time of copolymerizing the monomer composition is −50 to 150 ° C., preferably 20 to 100 ° C., and the polymerization time is preferably 0.5 to 72 hours. The molecular weight of the 2-methacryloyloxyethyl phosphorylcholine copolymer thus obtained varies depending on the polymerization temperature, the amount of a polymerization initiator and the amount of a polymerization degree regulator used, but is 5,000 to 1,000,000 in weight average molecular weight. Preferably, it is 30,000 to 100,000.
[0015]
In the present invention, if the weight average molecular weight of the 2-methacryloyloxyethyl phosphorylcholine copolymer is less than 5,000, the powder coating agent tends to fall off the powder surface, which is not preferable. When the weight average molecular weight of the polymer is larger than 1,000,000, the solubility in a solvent becomes extremely poor.
[0016]
In the present invention, the target coated powder is provided by surface-coating the powder with a powder coating agent comprising a 2-methacryloyloxyethyl phosphorylcholine copolymer. As the powder, inorganic powder and organic powder can be roughly classified. As the inorganic powder, any inorganic powder may be used.For example, silicic acid, silicic anhydride, magnesium silicate, talc, kaolin, mica, sericite, bentonite, titanium-coated mica, bismuth oxychloride Inorganic powders such as zirconium oxide, magnesium oxide, zinc oxide, titanium oxide, calcium carbonate, magnesium carbonate, iron oxide, ultramarine, navy blue, chromium oxide, chromium hydroxide, calamine, zeolite, etc. can be used as inorganic powders. Preferred examples are given. As the organic powder, any organic powder may be used, for example, cellulose powder, silk powder, nylon powder, polyethylene powder, polystyrene powder, polypropylene powder, and the like, polyamide, polyester, polyethylene, polypropylene, Preferred examples include organic powders composed of polystyrene, polyurethane, vinyl resin, urea resin, phenol resin, fluorine resin, silicon resin, acrylic resin, melamine resin, epoxy resin, polycarbonate resin, divinylbenzene-styrene resin, cellulose resin, and the like. Can be. Further, the inorganic powder and the organic powder may be used as a powder of one kind or a mixture of two or more kinds. The particle diameter of the powder is preferably about 10 nm to 100 μm.
Powders having a particle size of less than 10 nm are difficult to obtain, and powders having a particle size of more than 100 μm are not preferred because they have a poor feel to the skin. More preferably, mica, sericite, polyethylene powder, or polypropylene powder having a particle diameter of 100 nm to 10 μm can be most preferably used.
[0017]
The coating amount of the powder coating agent on the powder of the present invention is designed as an amount capable of sufficiently covering the surface of the powder, and is preferably 0.01 to 10 parts by weight based on 100 parts by weight of the powder. Parts by weight, more preferably 0.01 to 1 part by weight.
[0018]
The powder surface-coated with the powder coating agent of the present invention is produced, for example, as follows.
A 2-methacryloyloxyethyl phosphorylcholine copolymer is dissolved in a mixed solvent of an alcohol having a boiling point of 120 ° C. or lower and a nonpolar organic solvent having a boiling point of 120 ° C. or lower, and the powder is immersed in the obtained solution. Next, the solvent is removed from the solution, and the powder is dried. More specifically, the surface coating treatment with the powder treating agent of the present invention can be divided into the following steps (A) to (D).
[0019]
(A) A 2-methacryloyloxyethyl phosphorylcholine copolymer, which is a powder coating agent of the present invention, is dissolved in a mixed solvent of an alcohol having a boiling point of 120 ° C or lower and a nonpolar organic solvent having a boiling point of 120 ° C or lower. Adjust treatment agent.
(B) A powder is immersed in the powder coating agent.
(C) The solvent is removed.
(D) Dry the powder.
[0020]
In the step (A), a powder coating agent of the present invention, 2-methacryloyloxyethyl phosphorylcholine copolymer, is dissolved in a mixed solvent of a specific alcohol and a non-polar organic solvent, and the powder coating agent is added. adjust.
[0021]
Here, the alcohol used is an alcohol having a boiling point of 120 ° C. or less. Specific examples include methanol, ethanol, propanol, isopropanol, pentyl alcohol, isobutyl alcohol, s-butyl alcohol, t-butyl alcohol and mixtures thereof.Most preferably, methanol is used because it is easily available. , Ethanol and isopropanol.
[0022]
The non-polar organic solvent used is a non-polar organic solvent having a boiling point of 120 ° C. Here, the non-polar organic solvent means a solvent having no polar functional group such as a hydroxyl group.
Non-polar organic solvents include hydrocarbon solvents, ether solvents, ketone solvents, and ester solvents. Specifically, examples of the hydrocarbon solvent include n-pentane, isopentane, n-hexane, n-heptane, n-octane, isooctane, benzene, cyclohexane, methylcyclohexane, and a mixture thereof. Examples of the ether solvent include ethyl ether, isopropyl ether, dioxane, tetrahydrofuran, 1,3-dioxolan, methyl t-butyl ether, and a mixture thereof. Ketone solvents include acetone, methyl ethyl ketone, methyl isobutyl ketone and mixtures thereof. Further, examples of the ester solvent include methyl acetate, ethyl acetate, isopropyl acetate, isobutyl acetate, propyl acetate, and a mixture thereof. It is not preferable that the non-polar organic solvent has a boiling point higher than 120 ° C. because it takes time to dry the powder coated with the powder coating agent of the present invention. Among these nonpolar organic solvents, n-hexane, acetone, and ethyl acetate are most preferably used in consideration of safety during mass production, drying, and deodorization.
[0023]
In the present invention, the mixing ratio between the alcohol having a boiling point of 120 ° C. or less and the non-polar organic solvent having a boiling point of 120 ° C. or less is determined by the solubility and coating treatment of the 2-methacryloyloxyethyl phosphorylcholine copolymer. Although it is possible to appropriately control the drying conditions of the subsequent powder, it is suitable that the alcohol is 5 to 60% by weight and the nonpolar organic solvent is 40 to 95% by weight. If the alcohol concentration is less than 5% by weight or higher than 60% by weight, the solubility of the 2-methacryloyloxyethyl phosphorylcholine copolymer becomes low, which is not preferable.
[0024]
In the present invention, the concentration of the 2-methacryloyloxyethyl phosphorylcholine copolymer in the powder coating agent is desirably 0.01 to 5 parts by weight based on 100 parts by weight of the mixed solvent. If the concentration of the 2-methacryloyloxyethyl phosphorylcholine copolymer is less than 0.01 part by weight, it is difficult to uniformly coat the powder surface, which is not preferable. On the other hand, when the concentration of the 2-methacryloyloxyethyl phosphorylcholine copolymer is higher than 5 parts by weight, it is not preferable because the powder aggregates.
As a method of dissolving the 2-methacryloyloxyethyl phosphorylcholine copolymer in the mixed solvent at a preferable concentration, for example, a 2-methacryloyloxyethyl phosphorylcholine copolymer is added to the mixed solvent, and the mixture is stirred, shaken, heated, and super-cooled. An ordinary method such as ultrasonic wave irradiation can be used. In this way, a powder coating treatment agent in which a 2-methacryloyloxyethyl phosphorylcholine copolymer is dissolved in a mixed solvent can be easily produced.
[0025]
In the step (B), the powder is immersed in the powder coating treatment agent prepared in the step (A). In this step, it is desirable to perform stirring. As the stirring method, any apparatus can be generally used as long as it stirs the solution, for example, a stirrer with a stirring blade or a disperser, a disperser such as a homomixer, or the like can be used, but preferably a stirrer is used. be able to. As a preferable stirring condition when this is used, it is preferable to perform the stirring at a room temperature lower than the heating condition for the reason of evaporation of the organic solvent.
[0026]
In the step (C), the solvent is removed. The method for removing the solvent in this step includes removal by filtration using filter paper or filter cloth, removal by centrifugation or decantation after powder sedimentation, and removal of the solvent. Examples of the method include a method of volatilization, and preferably removal by filtration can be used. As a preferable condition when this is used, it is preferable to carry out under normal pressure or pressurized condition for the reason of evaporation of the solvent.
[0027]
In the step (D), the powder is dried. Examples of the method for drying the powder in this step include drying under normal pressure or reduced pressure, and drying by heating. As a drying method, drying under reduced pressure can be preferably used. As a preferable condition when this is used, it is preferable to carry out the heating under reduced pressure in order to evaporate the solvent in a short time.
[0028]
As described above, the powder can be surface-coated, but the obtained powder can be used as a kind of raw material component in a generally known cosmetic by a generally known method. .
For example, the surface-coated powder of the present invention can be preferably blended with makeup cosmetics such as foundation, blusher, eyeshadow, lipstick, eyeliner, eye pencil, and facial cosmetics such as creams and emulsions. . In addition, the form after compounding may be any form such as powder, cake, emulsion, oil, gel, etc., and any form of cosmetics may be widely mixed. it can.
[0029]
Here, the blending amount of the surface-coated powder of the present invention in the cosmetic is appropriately selected in the range of 0.001 to 100% by weight based on the total amount of the powder. For example, in a powder product, 100% by weight can be used so that it consists only of the powder coated with the powder coating agent of the present invention. When the powder coated with the powder coating agent of the present invention is used for coloring an emulsified cosmetic or the like, addition of 0.001% by weight may be sufficient.
[0030]
The surface-coated powder of the present invention exhibits good dispersibility in silicone oils, hydrocarbon oils, ester oils and the like which are commonly used in cosmetics. In particular, when the main oil agent is silicone oil, no powder aggregation is observed. That is, when dispersed in a cosmetic such as a silicone oil, it has good compatibility and is effective as a component of an emulsified cosmetic. Preferred silicone oils as the dispersion medium include dimethylpolysiloxane, dimethylcyclopolysiloxane, methylphenylpolysiloxane, methylhydrogenpolysiloxane, polyoxyalkylene-modified organopolysiloxane, higher fatty acid-modified organopolysiloxane, and higher alcohol-modified organopolysiloxane. And trimethylsiloxysilicate. Furthermore, one or a mixture of two or more of the above-mentioned silicone oils may be mixed with a surface-coated powder, and further used as an emulsified cosmetic.
[0031]
The surface-coated powder of the present invention can be used by blending it as a kind of raw material component with the emulsified cosmetic by a generally known method. The emulsified cosmetic containing the powder may be appropriately mixed with other components usually contained in the emulsified cosmetic as long as the effects of the present invention are not impaired.
[0032]
For example, humectants such as propylene glycol, dipropylene glycol, 1,3-butylene glycol, glycerin, maltitol, sorbitol, polyethylene glycol, sodium hyaluronate, and pyrrolidone carboxylate; Ingredients include petrolatum, lanolin, ceresin, silicone wax, microcrystalline wax, carnauba wax, candelilla wax, solid and semi-solid oils such as higher fatty acids and higher alcohols, squalane, liquid paraffin, polybutene, dimethylpolysiloxane, methylphenyl Fluid oils such as polysiloxane, ester oil and triglyceride; other ingredients such as vitamin E and vitamin E acetate; astringents; antioxidants; preservatives; fragrances; PH adjusters such as sodium, lactic acid, sodium lactate and dibasic sodium phosphate; thickeners such as organically modified montmorillonite; UV absorbers; powder coatings comprising the 2-methacryloyloxyethyl phosphorylcholine copolymer of the present invention. Inorganic and organic powders other than the coated powder; inorganic and organic powders manufactured by a manufacturing method other than the manufacturing method of the present invention; other powders, inorganic and organic pigments, and the like can be blended.
[0033]
【Example】
Hereinafter, the present invention will be described in more detail with reference to Examples and Comparative Examples.
Synthesis Example 1 Synthesis of MPC-SMA copolymer (P-1)
13.5 g of 2-methacryloyloxyethyl phosphorylcholine (abbreviated as MPC), 36.5 g of stearyl methacrylate (abbreviated as SMA), and 0.01 g of azobisisobutyronitrile (abbreviated as AIBN) as a radical polymerization initiator. It was dissolved in 450 g of butanol, placed in a glass reaction tube for polymerization, replaced with nitrogen, and then polymerized in a thermostat at 50 ° C. for 72 hours. After completion of the polymerization, reprecipitation purification was performed using butanol as a good solvent and diethyl ether as a poor solvent, followed by drying by heating to obtain a target copolymer. The analysis results are shown in Table 1.
[0034]
Synthesis Example 2 Synthesis of MPC-IMA copolymer (P-2)
13.5 g of MPC, 36.5 g of isostearyl methacrylate (abbreviated as IMA), and AIBN (0.01 g) as a radical polymerization initiator were dissolved in isopropanol (450 g), put into a glass reaction tube for polymerization, and replaced with nitrogen. The polymerization was carried out in a thermostat at 50 ° C. for 72 hours. After completion of the polymerization, reprecipitation purification was performed using isopropanol as a good solvent and diethyl ether as a poor solvent, followed by heating and drying to obtain a target copolymer. The analysis results are shown in Table 1.
[0035]
Synthesis Example 3 Synthesis of MPC-BMA copolymer (C-1)
MPC (45 g), 5 g of n-butyl methacrylate (abbreviated as BMA), and AIBN (0.01 g) as a radical polymerization initiator were dissolved in ethanol (450 g), placed in a glass reaction tube for polymerization, and replaced with nitrogen. Polymerization was carried out in a bath at 50 ° C. for 72 hours. After completion of the polymerization, reprecipitation purification was performed using ethanol as a good solvent and diethyl ether as a poor solvent, followed by drying by heating to obtain a target copolymer. The analysis results are shown in Table 1.
[0036]
Synthesis Example 4 Synthesis of MPC homopolymer (C-2)
MPC (50 g) and AIBN (0.01 g) as a radical polymerization initiator were dissolved in ethanol (450 g), placed in a glass reaction tube for polymerization, replaced with nitrogen, and polymerized at 50 ° C. for 72 hours in a thermostat. . After completion of the polymerization, reprecipitation purification was performed using ethanol as a good solvent and diethyl ether as a poor solvent, followed by heating and drying to obtain a target polymer. The analysis results are shown in Table 1.
[0037]
Synthesis Example 5 Synthesis of MPC-SMA copolymer (C-3)
MPC (4.5 g), SMA (45.5 g), and AIBN (0.01 g) as a radical polymerization initiator were dissolved in butanol (450 g), placed in a glass reaction tube for polymerization, and purged with nitrogen. Polymerization was performed at 50 ° C. for 72 hours. After completion of the polymerization, reprecipitation purification was performed using butanol as a good solvent and diethyl ether as a poor solvent, followed by drying by heating to obtain a target polymer. The analysis results are shown in Table 1.
[0038]
Synthesis Example 6 Synthesis of MPC-SMA copolymer (C-4)
MPC (44.5 g), SMA (5.5 g), and AIBN (0.01 g) as a radical polymerization initiator were dissolved in butanol (450 g), placed in a glass reaction tube for polymerization, and replaced with nitrogen. Polymerization was performed at 50 ° C. for 72 hours. After completion of the polymerization, reprecipitation purification was performed using butanol as a good solvent and diethyl ether as a poor solvent, followed by drying by heating to obtain a target copolymer. The analysis results are shown in Table 1.
[0039]
Synthesis Example 7 Synthesis of MPC-IMA copolymer (C-5)
MPC (4.5 g), IMA (45.5 g), and AIBN (0.01 g) as a radical polymerization initiator were dissolved in isopropanol (450 g), placed in a glass reaction tube for polymerization, and replaced with nitrogen. Polymerization was performed at 50 ° C. for 72 hours. After completion of the polymerization, reprecipitation purification was performed using isopropanol as a good solvent and diethyl ether as a poor solvent, followed by heating and drying to obtain a target copolymer. The analysis results are shown in Table 1.
[0040]
Synthesis Example 8 Synthesis of MPC-IMA copolymer (C-6)
MPC (23.3 g), IMA (26.7 g), and AIBN (0.01 g) as a radical polymerization initiator were dissolved in isopropanol (450 g), placed in a glass reaction tube for polymerization, and replaced with nitrogen. Polymerization was performed at 50 ° C. for 72 hours. After completion of the polymerization, reprecipitation purification was performed using isopropanol as a good solvent and diethyl ether as a poor solvent, followed by heating and drying to obtain a target copolymer. The analysis results are shown in Table 1.
[0041]
[Table 1]

[0042]
The abbreviations used in Table 1 are as follows.
MPC: 2-methacryloyloxyethyl phosphorylcholine,
BMA: n-butyl methacrylate,
SMA: stearyl methacrylate,
IMA: isostearyl methacrylate,
AIBN: azobisisobutyronitrile.
[0043]
Example 1-1
P-1 (2.5 g) synthesized in Synthesis Example 1 was added to a mixed solvent (250 mL) of isopropanol (50% by weight) / n-hexane (50% by weight), and the mixture was stirred and dissolved at room temperature. Next, 100 g of mica (manufactured by Kakuhachi Fish Foil Co., Ltd., Mica R-1000) was added thereto, and the mixture was stirred, filtered by suction, and the powder was taken out. The solvent was distilled off while stirring in an oven at 80 ° C. to obtain mica treated with a surface coating agent. The obtained mica after the surface coating treatment was evaluated for powder as follows.
[0044]
<Evaluation method of powder>
As a powder evaluation method, the feel to the skin was evaluated by three points of a stack feeling (feel at the time of spreading), a sit-down feeling, and water resistance (sensory evaluation).
(1) Evaluation criteria for a feeling of stack
The feeling of stacking was evaluated by one expert sensory examiner on all samples, and the degree of elongation when 50 mg of powder was placed on the back of the left hand and extended with the belly of the forefinger of the right hand was good, normal, and bad. It was classified into three stages. The evaluation at this time was performed subjectively by a professional sensory tester, and scored as “good” as 3 points, “normal” as 2 points, and “bad” as 1 point.
(2) Criteria for evaluation
The feeling of sittness was evaluated by one expert sensory examiner on all samples, placing 50 mg of powder on the back of the left hand and spreading it with the index finger of the right hand. It was classified into three stages. The evaluation at this time was performed subjectively by a professional sensory tester, and scored as “good” as 3 points, “normal” as 2 points, and “bad” as 1 point.
(3) Water resistance evaluation criteria
Water resistance was tested on all samples by one expert sensory examiner, and 50 mg of the powder was placed on the back of the left hand and spread using the right index finger. Next, tap water (flow rate 50 mL / min) was brought into contact with the skin surface where the powder was spread for 3 minutes. The amount of powder remaining on the skin surface was visually identified and classified into good, normal, and bad. The evaluation at this time was performed subjectively by a professional sensory tester, and scored as “good” as 3 points, “normal” as 2 points, and “bad” as 1 point.
The results are shown in Table 2. In addition, about the comprehensive evaluation of Table 2, it scored by making "good" 3 points, "normal" 2 points, and "bad" 1 point.
[0045]
Example 1-2
A surface coating treatment was performed in the same manner as in Example 1-1, except that the addition amount of P-1 in Example 1-1 was changed from 2.5 g to 0.25 g, and the powder was evaluated. The results are shown in Table 2.
[0046]
Example 1-3
Example 1 was repeated except that 2.5 g of P-1 in Example 1-1 was changed to 0.025 g, and the mixed solvent was changed to methanol (60% by weight) / n-hexane (40% by weight). Surface coating treatment was performed in the same manner as in 1-1, and the powder was evaluated. The results are shown in Table 2.
[0047]
Example 1-4
Except that the addition amount of P-1 in Example 1-1 was changed to 2.5 g and 0.0025 g, and the organic mixed solvent was changed to methanol (60% by weight) / n-hexane (40% by weight). Surface coating was performed in the same manner as in Example 1-1, and the powder was evaluated. The results are shown in Table 2.
[0048]
Example 1-5
P-2 (2.5 g) synthesized in Synthesis Example 2 was added to a mixed solvent (250 mL) of ethanol (10% by weight) / n-hexane (60% by weight) / acetone (30% by weight) and stirred at room temperature. And dissolved. Next, 100 g of sericite (Eight Pearl 300S, manufactured by Kakuhachi Fish Foil Co., Ltd.) was added. Otherwise, the surface was coated in the same manner as in Example 1-1, and the powder was evaluated. The results are shown in Table 2.
[0049]
Example 1-6
A surface coating treatment was carried out in the same manner as in Example 1-5, except that the addition amount of P-2 in Example 1-5 was changed from 2.5 g to 0.25 g, and the powder was evaluated. The results are shown in Table 2.
[0050]
Example 1-7
Example 1-5 Except that 2.5 g of P-2 in Synthesis Example 1-5 was changed to 0.025 g and the mixed solvent was changed to methanol (5% by weight) / ethyl acetate (95% by weight). The surface coating treatment was performed in the same manner as described above, and the powder was evaluated. The results are shown in Table 2.
[0051]
Example 1-8
Example 1-5 Except that 2.5 g of P-2 in Synthesis Example 1-5 was replaced with 0.0025 g and the mixed solvent was methanol (5% by weight) / ethyl acetate (95% by weight). The surface coating treatment was performed in the same manner as described above, and the powder was evaluated. The results are shown in Table 2.
[0052]
Comparative Example 1-1
The powder was evaluated using 100 g of untreated mica (Mika R-1000, manufactured by Kakuhachi Fish Scale Co., Ltd.) as it was. Table 3 shows the results. In addition, about the comprehensive evaluation of Table 3, "good" was scored as 3 points, "normal" was 2 points, and "bad" was 1 point.
[0053]
Comparative Example 1-2
C-1 (2.5 g) synthesized in Synthesis Example 3 was added to ethanol (250 mL), and the mixture was stirred and dissolved at room temperature. Next, 100 g of mica (manufactured by Kakuhachi Fish Foil Co., Ltd., Mica R-1000) was added thereto, and the mixture was stirred, filtered by suction, and the powder was taken out. Ethanol was distilled off while stirring in an oven at 80 ° C. to obtain mica treated with a surface coating agent. With respect to the obtained mica after the surface coating treatment, the powder was evaluated in the same manner as in Example 1-1. The results are shown in Table 3.
[0054]
Comparative Example 1-3
C-2 (0.25 g) synthesized in Synthesis Example 4 was added to 250 mL of methanol and dissolved by stirring at room temperature. Next, 100 g of mica (manufactured by Kakuhachi Fish Foil Co., Ltd., Mica R-1000) was added thereto, and the mixture was stirred, filtered by suction, and the powder was taken out. Methanol was distilled off while stirring in an oven at 80 ° C. to obtain mica treated with a surface coating agent. With respect to the obtained mica after the surface coating treatment, the powder was evaluated in the same manner as in Example 1-1. The results are shown in Table 3.
[0055]
Comparative Example 1-4
A surface coating treatment was performed in the same manner as in Example 1-1 except that C-3 (0.25 g) synthesized in Synthesis Example 5 was used instead of P-1 (2.5 g) synthesized in Synthesis Example 1. , The powder was evaluated. The results are shown in Table 3.
[0056]
Comparative Example 1-5
A surface coating treatment was performed in the same manner as in Example 1-1 except that C-4 (0.25 g) synthesized in Synthesis Example 6 was used instead of P-1 (2.5 g) synthesized in Synthesis Example 1. , The powder was evaluated. The results are shown in Table 3.
[0057]
Comparative Example 1-6
The powder was evaluated in the same manner as in Example 1-1, using 100 g of untreated sericite (Eight Pearl 300S, manufactured by Kakuhachi Fish Scale Co., Ltd.) as it was. The results are shown in Table 3.
[0058]
Comparative Example 1-7
Instead of mica (100 g), a surface coating treatment was performed in the same manner as in Comparative Example 1-2 except that 100 g of sericite (Eight Pearl 300S, manufactured by Kakuhachi Fish Foil Co., Ltd.) was used, and the powder was evaluated. . The results are shown in Table 3.
[0059]
Comparative Example 1-8
Instead of mica (100 g), surface coating treatment was performed in the same manner as in Comparative Example 1-3 except that 100 g of sericite (Eight Pearl 300S, manufactured by Kakuhachi Fish Foil Co., Ltd.) was used, and the powder was evaluated. . The results are shown in Table 3.
[0060]
Comparative Example 1-9
Instead of mica (100 g), a surface coating treatment was performed in the same manner as in Comparative Example 1-4 except that 100 g of sericite (Eight Pearl 300S manufactured by Kakuhachi Fish Foil Co., Ltd.) was used, and the powder was evaluated. . The results are shown in Table 3.
[0061]
Comparative Example 1-10
Except for using 100 g of sericite (Eight Pearl 300S, manufactured by Kakuhachi Fish Foil Co., Ltd.) instead of mica (100 g), all were surface-coated in the same manner as in Comparative Example 1-5, and the powder was evaluated. did. The results are shown in Table 3.
[0062]
[Table 2]

[0063]
[Table 3]

As described above, from the results of Examples 1-1 to 1-8 and Comparative Examples 1-1 to 1-10, the powder after the surface coating treatment of the present invention has a good stack feeling, a good sit-down feeling and excellent water resistance. I knew it was there.
[0064]
Example 2-1
P-1 (3 g) synthesized in Synthesis Example 1 was added to a mixed solvent (1 L) of isopropanol (50% by weight) / n-hexane (50% by weight), and dissolved by stirring at room temperature. Next, 997 g of talc (manufactured by Takehara Chemical Industry Co., Ltd.) was added and dispersed by a disperser, and then placed in a kneader. The obtained talc after the surface coating treatment was adhered to the skin and visually observed.The talc after the surface coating treatment had a smooth elongation, had good adhesion, had a crisp use feeling, and It did not settle even when floated on water and had excellent water repellency. Thus, it was confirmed that the surface coating treatment can be performed using talc, similarly to mica and sericite.
[0065]
Example 2-2
P-2 (5 g) synthesized in Synthesis Example 2 was added to a mixed solvent (1 L) of methanol (60% by weight) / n-hexane (40% by weight), and dissolved by stirring at room temperature. Next, 995 g of fine particle titanium oxide (Taika Co., Ltd., MT500) was added and dispersed by a disperser, and then placed in a kneader, the pressure was reduced while stirring, and the mixed solvent was removed to obtain fine particle titanium oxide having a surface coating treatment. The obtained fine particle titanium oxide after the surface coating treatment was adhered to the skin and visually observed. The fine particle titanium oxide after the surface coating treatment had smooth elongation, good adhesion, and was used as a sit-down. It had a good feeling, did not settle even when floated on water, and had excellent water repellency. As a result, it was confirmed that the surface coating treatment can be performed similarly to mica and sericite even when the coated fine particle titanium oxide is used.
[0066]
Example 3-1
The X component was weighed into a Henschel mixer at the compounding amount shown in Table 4 and mixed at high speed for 2 minutes to obtain a toned powder (100 g). This was previously added to a mixed solvent of ethanol (10% by weight) / n-hexane (60% by weight) / acetone (30% by weight) at a concentration of 0.01% by weight of the Y component (P-1 synthesized in Synthesis Example 1). The solution was immersed in a solution (100 mL) prepared by dissolving so as to be stirred, stirred, filtered by suction, and the powder was taken out. The mixed solvent was distilled off with stirring in an oven at 80 ° C., pulverized with a 1 mm herringbone screen-equipped pulverizer, and then mixed to prepare a surface-coated toning powder (100 g).
[0067]
Example 3-2
The X component was weighed into a Henschel mixer at the compounding amount shown in Table 4 and mixed at high speed for 2 minutes to obtain a toned powder (100 g). This was previously added to a mixed solvent of ethanol (10% by weight) / n-hexane (60% by weight) / acetone (30% by weight) at a concentration of 0.1% by weight of the Y component (P-1 synthesized in Synthesis Example 1). The solution was immersed in a solution (100 mL) prepared by dissolving so as to be stirred, stirred, filtered by suction, and the powder was taken out. The mixed solvent was distilled off while stirring in an oven at 80 ° C., and the mixture was pulverized and mixed with a 1 mm herringbone screen-equipped pulverizer to prepare a surface-coated toned powder (100 g).
[0068]
Example 3-3
The X component was weighed into a Henschel mixer at the compounding amount shown in Table 4 and mixed at high speed for 2 minutes to obtain a toned powder (100 g). This is prepared by dissolving the Y component (P-2 synthesized in Synthesis Example 1) to a concentration of 0.1% by weight in a methanol (5% by weight) / ethyl acetate (95% by weight) mixed solvent in advance. After being immersed in the solution (100 mL) and stirred, the mixture was subjected to suction filtration to take out a powder. The mixed solvent was distilled off with stirring in an oven at 80 ° C., pulverized with a 1 mm herringbone screen-equipped pulverizer, and then mixed to prepare a surface-coated toning powder (100 g).
[0069]
Reference Example 1
The X component was weighed into a Henschel mixer at the blending amounts shown in Table 4 and mixed at high speed for 2 minutes. Thereafter, the mixture was pulverized with a 1 mm herringbone screen-equipped pulverizer to prepare a toned powder (100 g) for comparison.
[0070]
[Table 4]

[0071]
Examples 4-1 to 4-3
The component A or the component C was mixed at the compounding amount shown in Table 5. Next, each was heated and melted at 80 ° C. The B component (various powders subjected to the surface coating treatment in Examples 3-1 to 3-3) was added to the A component, mixed with a mixer, and the C component was gradually added thereto, followed by emulsification, followed by cooling with stirring. Thus, a foundation (100 g) was obtained.
[0072]
Comparative Example 2
The component A or the component C was mixed at the compounding amount shown in Table 5. Next, each was heated and melted at 80 ° C. The B component (the powder prepared in Reference Example 1) was added to the A component, and the mixture was mixed with a mixer. The C component was gradually added thereto, followed by emulsification, followed by cooling with stirring to obtain a foundation (100 g). .
[0073]
Example 5
Using the foundations prepared in Examples 4-1 to 4-3 and Comparative Example 2, the use characteristics were evaluated by ten professional panelists. The evaluation method was to apply the foundations of Examples 4-1 to 4-3 to the right half face, apply the foundation of Comparative Example 2 to the left half face, and apply the foundation of Comparative Example 2 to the right half face. The applied foundation was subjected to a sensory evaluation of “sit feeling”, “cosmetic appearance”, and “adhesion”, and further, as an evaluation after five hours of makeup, a sensory evaluation was performed for a total of four items of “make-up”. In comparison with the foundation of Comparative Example 2 for each item of the feeling of use, 3 points of “3 points: better than the comparative example”, “2 points: equivalent to the comparative example”, and “1 point: the comparative example is better” At the stage, the sensory evaluation was performed subjectively by 10 specialized panelists, and the average score of 10 persons for each item was calculated to be the evaluation result. The results are shown in the column of sensory evaluation in Table 5.
[0074]
[Table 5]

[0075]
From the above results, all of the foundations of the present invention of Examples 4-1 to 4-3 have an excellent cosmetic effect as compared with the foundation containing the powder not subjected to the surface coating treatment. In particular, when it comes to the feeling of sittling, it should also be noted that Examples 4-1 to 4-3 are remarkably improved as compared with Comparative Example 2, which is the powder coating agent of the present invention. This is because a certain 2-methacryloyloxyethyl phosphorylcholine copolymer is excellent in moisturizing properties, and the effect of the surface coating treatment by this is clear.
[0076]
Example 6
To a mixed solvent (1 L) of methanol (60% by weight) / n-hexane (40% by weight), P-1 (3 g) synthesized in Synthesis Example 1 was added and dissolved by stirring at room temperature. 21.4 parts by weight of talc (Talc, manufactured by Kosakai Pharmaceutical Co., Ltd.), 40 parts by weight of sericite (Eight Pearl 300S, manufactured by Kakuhachi Fish Foil Co., Ltd.), and mica (Kadohachi Fish Foil) ), 30 parts by weight of mica R-1000), 6 parts by weight of titanium oxide (manufactured by Titanium Industry Co., Ltd., chronos titanium oxide KA-10), and 2 parts of iron oxide yellow (manufactured by Titanium Industry Co., Crocs) 2 Parts by weight, 0.5 parts by weight of Bengala (manufactured by Titanium Industry Co., Ltd., mapico synthetic iron oxide R-516-L), black iron oxide (manufactured by Titanium Industry Co., Ltd., mapico synthetic iron oxide BL-100) A mixed powder having a total amount of 997 g by mixing 0.1 parts by weight was added. After uniformly mixing with a Henschel mixer and dispersing with a disper, the mixture was placed in a kneader and depressurized while stirring, and the mixed solvent was removed to obtain a mixed powder after surface coating treatment. The mixed powder subjected to the surface coating treatment had good adhesiveness, a smooth feeling of use, did not settle when floated on water, and had excellent water repellency, despite smooth elongation.
[0077]
Reference Example 2
21.4 parts by weight of talc (manufactured by Kosakai Pharmaceutical Co., Ltd., talc), 40 parts by weight of sericite (manufactured by Kakuhachi Fish Foil Co., Ltd., Eight Pearl 300S), mica (manufactured by Kakuhachi Fish Foil Co., Ltd.) , Mica R-1000) 30 parts by weight, titanium oxide (manufactured by Titanium Industry Co., Ltd., chronos titanium oxide KA-10) 6 parts by weight, yellow iron oxide (manufactured by Titanium Industry Co., Ltd., Crocs) 2 parts by weight, 0.5 parts by weight of bengara (manufactured by Titanium Industry Co., Ltd., mapico synthetic iron oxide R-516-L), 0.1 part by weight of black iron oxide (manufactured by Titanium Industry Co., Ltd., mapico synthetic iron oxide BL-100) The parts were weighed, and the powder having a total amount of 500 g was uniformly mixed with a Henschel mixer to obtain a mixed powder.
[0078]
Reference Example 3
21.4 parts by weight of talc (manufactured by Kosakai Pharmaceutical Co., Ltd., talc), 40 parts by weight of sericite (manufactured by Kakuhachi Fish Foil Co., Ltd., Eight Pearl 300S), mica (manufactured by Kakuhachi Fish Foil Co., Ltd.) , Mica R-1000) 30 parts by weight, titanium oxide (manufactured by Titanium Industry Co., Ltd., chronos titanium oxide KA-10) 6 parts by weight, yellow iron oxide (manufactured by Titanium Industry Co., Ltd., Crocs) 2 parts by weight, 0.5 parts by weight of Bengala (manufactured by Titanium Industry Co., Ltd., mapico synthetic iron oxide R-516-L), 0.1 of black iron oxide (manufactured by Titanium Industry Co., Ltd., mapico synthetic iron oxide BL-100) 10 parts of methyl hydrogen polysiloxane was slowly added while weighing parts by weight and mixing 490 g of powder with a Henschel mixer to make the whole uniform. Thereafter, the mixture was left in an atmosphere of 200 ° C. for 4 hours, and further cooled to obtain a silicon baking treated mixed powder.
[0079]
Example 7-1
The raw material components were mixed in the amounts shown in Table 6, mixed and pulverized using a Henschel mixer, and then press-molded to obtain a solid foundation. This foundation does not cake (whether the surface becomes oily and cannot be taken on a sponge, etc.) when used with or without water, has excellent adhesiveness and water resistance, is resistant to makeup collapse, , And had a good use feeling.
[0080]
Comparative Example 3-1
The raw material components were mixed in the amounts shown in Table 6, mixed and pulverized using a Henschel mixer, and then press-molded to obtain a solid foundation. This foundation shows good usability when used without water, but when used with water, the cake hardens over time and causes caking. In addition, it did not have water resistance, and lacked the durability of makeup.
[0081]
Comparative Example 3-2
The raw material components were mixed in the amounts shown in Table 6, mixed and pulverized using a Henschel mixer, and then press-molded to obtain a solid foundation. This foundation did not cake even when used with or without water, and had excellent water resistance, but the skin was easily bulked and lacked moisturizing properties.
[0082]
[Table 6]

[0083]
As described above, from the results of Example 7-1 and Comparative Examples 3-1 and 3-2, when the surface-coated powder of the present invention is blended with untreated powder or silicon-baked powder, It was found that a foundation having excellent water resistance and a feeling of tightness could be provided.
[0084]
Example 8-1
P-1 (0.25 g) synthesized in Synthesis Example 1 was added to a mixed solvent (250 mL) of isopropanol (50% by weight) / n-hexane (50% by weight), and the mixture was stirred and dissolved at room temperature. Next, 100 g of titanium oxide (Chronos Titanium Oxide KA-10, manufactured by Titanium Industry Co., Ltd.) was added, and the mixture was stirred, filtered by suction, and the powder was taken out. The solvent was distilled off while stirring in an oven at 80 ° C. to obtain titanium oxide having a surface coating treatment.
[0085]
Example 8-2
The same treatment as in Example 8-1 was carried out except that titanium oxide was replaced with 100 g of iron oxide yellow (manufactured by Titanium Industry Co., Ltd., Crocs) to obtain a surface-coated iron oxide yellow.
Example 8-3: Preparation of P-1 coated iron oxide red
Iron oxide red treated in the same manner as in Example 8-1, except that titanium oxide was changed to 100 g of iron oxide red (manufactured by Titanium Industry Co., Ltd., mapico synthetic iron oxide R-516-L). Got.
[0086]
Example 8-4
Except that titanium oxide was replaced with 100 g of sericite (Eight Pearl 300S, manufactured by Kakuhachi Fish Co., Ltd.), the same treatment as in Example 8-1 was performed to obtain surface-coated sericite.
Example 8-5
Except that titanium oxide was replaced with 100 g of iron oxide black (manufactured by Titanium Industry Co., Ltd., Mapico synthetic iron oxide BL-100), the same treatment as in Example 8-1 was performed to obtain a surface-coated iron oxide black. Was.
[0087]
Example 8-6
The same treatment as in Example 8-1 was carried out except that the titanium oxide was replaced with 100 g of fine particle titanium oxide (manufactured by Teika Co., Ltd., fine particle titanium MT100T) to obtain a fine particle titanium oxide having a surface coating treatment.
Example 8-7
The same treatment as in Example 8-1 was carried out except that the titanium oxide was replaced with 100 g of kaolin (Kaolin JP-100, manufactured by Tsuchiya Kaolin Industries, Ltd.) to obtain a kaolin with a surface coating treatment.
[0088]
Example 8-8
Except that titanium oxide was replaced with 100 g of zinc oxide (ZINCA-20, manufactured by Sakai Chemical Industry Co., Ltd.), the same treatment as in Example 8-1 was carried out to obtain surface-coated zinc oxide.
Example 8-9
Except that 100 g of cobalt titanate (Finecela G-N-1 manufactured by Nikko Rica Co., Ltd.) in which titanium oxide was powdered, the surface treatment was performed in the same manner as in Example 8-1, and titanic acid having a surface coating treatment was used. Cobalt was obtained.
[0089]
Reference Example 4-1
Except for using C-2 synthesized in Synthesis Example 4 in place of P-1 synthesized in Synthesis Example 1, the same treatment as in Example 8-1 was performed to obtain a surface-coated titanium oxide.
Reference Example 4-2
The same treatment as in Example 8-4 was carried out except that C-2 synthesized in Synthesis Example 4 was used instead of P-1 synthesized in Synthesis Example 1, to obtain surface-coated sericite.
[0090]
Reference Example 4-3
The procedure of Example 8-2 was repeated, except that C-2 synthesized in Synthesis Example 4 was used instead of P-1 synthesized in Synthesis Example 1, to obtain a surface-coated iron oxide yellow.
Reference Example 4-4
Except that C-2 synthesized in Synthesis Example 4 was used instead of P-1 synthesized in Synthesis Example 1, the same treatment as in Example 8-6 was performed to obtain a fine particle titanium oxide surface-treated.
[0091]
Reference Example 4-5
Except for using C-2 synthesized in Synthesis Example 4 in place of P-1 synthesized in Synthesis Example 1, the same treatment as in Example 8-9 was performed to obtain a surface-coated cobalt titanate.
[0092]
Example 9
The raw material components shown in Table 7 were blended, mixed and pulverized, and then press-molded to obtain a solid pressurer. The obtained pusher was excellent in adhesiveness and water resistance, hardly disintegrated in makeup, maintained a crisp feel, and had a good use feel.
[0093]
[Table 7]

[0094]
Example 10
The components shown in Table 8 were blended and mixed to obtain a foundation. The obtained foundation was excellent in adhesiveness and water resistance, hardly disintegrated in makeup, maintained a crisp feel, and had a good use feel.
[0095]
[Table 8]

[0096]
Example 11
At the compounding amount of Example 11 shown in Table 9, the component C was added to the component B which was dissolved by heating and dispersed. Next, this was added to the previously heated component A and emulsified to obtain a makeup base. The obtained makeup base material had good adhesion to the foundation, did not easily lose makeup, had a long lasting feel, and had a good use feeling.
[0097]
Comparative Example 4
At the compounding amount of Reference Example 5 shown in Table 9, the component C was first added to the component B which was dissolved by heating and dispersed. Next, this was added to the previously heated component A and emulsified to obtain a makeup base. Although the obtained makeup base had a touchy feel, it was easy to cause makeup collapse.
[0098]
[Table 9]

[0099]
Example 12
The component A was uniformly mixed with a Henschel mixer at the compounding amounts shown in Table 10 to obtain a mixed powder. Next, P-1 (2.5 g) synthesized in Synthesis Example 1 was added to a mixed solvent (250 mL) of isopropanol (50% by weight) / n-hexane (50% by weight) and stirred at room temperature to dissolve. Then, the mixed powder prepared above was added, and the mixture was stirred and filtered by suction to take out the powder. The solvent was distilled off while stirring in an oven at 80 ° C. to obtain a mixed powder whose surface was coated. Next, with the blending amount shown in Table 10, the coated powder mixture and the C component uniformly mixed separately were uniformly mixed with a Henschel mixer. This was pulverized with a pulverizer, the particle size was adjusted through a mesh, and compression molded on a metal plate to obtain an eye shadow.
The obtained eyeshadow had a smooth elongation and good adhesion, had a crisp use feeling, and was excellent in durability.
[0100]
[Table 10]

[0101]
Example 13
The component A was uniformly mixed with a Henschel mixer in the amounts shown in Table 11 to obtain a mixed powder. Next, P-1 (2.5 g) synthesized in Synthesis Example 1 was added to a mixed solvent (250 mL) of isopropanol (50% by weight) / n-hexane (50% by weight) and stirred at room temperature to dissolve. Then, the mixed powder prepared above was added, and the mixture was stirred and filtered by suction to take out the powder. The solvent was distilled off while stirring in an oven at 80 ° C. to obtain a mixed powder whose surface was coated. Next, the C component was added to the coated powder mixture at the compounding amount shown in Table 11, and the mixture was uniformly mixed with a Henschel mixer, and the D component was sequentially added and uniformly mixed. This was pulverized with a pulverizer and put into a container through a mesh to obtain a face powder.
The obtained face powder had smooth elongation, had a comfortable use feeling, and did not easily cause makeup collapse.
[0102]
[Table 11]

[0103]
【The invention's effect】
ADVANTAGE OF THE INVENTION According to the powder coating material of this invention, a powder can be surface-treated to a powder excellent in a feeling of stacking, and excellent in a feeling of situ and water resistance.
The powder treated with the powder coating agent of the present invention has a good stack feeling, a good sit feeling and excellent water resistance. Therefore, it is possible to provide a cosmetic powder having excellent moisture retention properties while being water resistant.
According to the powder surface coating method of the present invention, it is possible to provide a method for uniformly coating the powder surface under mild and environmentally friendly conditions.
The cosmetic containing the surface-coated powder of the present invention is excellent in situ feeling, feeling in use, cosmetic appearance and adhesion, and is also excellent in cosmetic durability.

Claims (7)

A powder coating comprising a 2-methacryloyloxyethyl phosphorylcholine copolymer represented by the following formula (1) and having a weight average molecular weight of 5,000 to 1,000,000.

(R ¹ and R ^{2 each} represent a hydrogen atom or a methyl group. X and y each represent the ratio of each constituent monomer to the total number of moles of the constituent monomers, and x / (x + y) = 0.2 to 0.4.) A powder that has been surface-coated with the powder coating agent according to claim 1. Powder coating, wherein the powder coating material according to claim 1 is dissolved in a mixed solvent comprising 5 to 60% by weight of an alcohol having a boiling point of 120 ° C or lower and 40 to 95% by weight of a nonpolar organic solvent having a boiling point of 120 ° C or lower. Processing agent. A method for coating a surface of a powder, comprising immersing the powder in the powder coating treating agent according to claim 3, removing a solvent, and drying the solvent. A toning powder comprising the powder of claim 2. A cosmetic comprising the powder according to claim 2. A makeup cosmetic comprising the powder according to claim 2.