JPH10310508A - Modified powder, and cosmetic containing the same - Google Patents
Modified powder, and cosmetic containing the sameInfo
- Publication number
- JPH10310508A JPH10310508A JP9136116A JP13611697A JPH10310508A JP H10310508 A JPH10310508 A JP H10310508A JP 9136116 A JP9136116 A JP 9136116A JP 13611697 A JP13611697 A JP 13611697A JP H10310508 A JPH10310508 A JP H10310508A
- Authority
- JP
- Japan
- Prior art keywords
- fluorine
- group
- substituted alkyl
- alkyl
- powder
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Abstract
Description
【発明の詳細な説明】DETAILED DESCRIPTION OF THE INVENTION
【０００１】[0001]
【発明の属する技術分野】本発明は、撥水性を有するフ
ッ素化合物含有基と親水性基を同時に有するフッ素アル
キル・（ポリ）グリセリン共変性シリコーン化合物にて
表面処理された改質粉体並びに、それを配合した、撥水
撥油性、耐久性に優れた化粧料に関するものである。The present invention relates to a modified powder surface-treated with a fluorine-alkyl / (poly) glycerin co-modified silicone compound having both a fluorine-containing group having water repellency and a hydrophilic group, and a modified powder thereof. And cosmetics having excellent water and oil repellency and durability.
【０００２】さらに詳しくは、フッ素アルキル・（ポ
リ）グリセリン共変性シリコーン被覆粉体が水を保持し
た時、撥水撥油性を失わずに、粉体自身が皮膚との密着
性を有するようになる現象を利用することで、耐皮脂
性、耐水性、耐久性に優れた化粧料に関するものであ
る。More specifically, when a fluorine-alkyl / (poly) glycerin-co-modified silicone-coated powder retains water, the powder itself has adhesiveness to the skin without losing water and oil repellency. The present invention relates to cosmetics having excellent sebum resistance, water resistance, and durability by utilizing the phenomenon.
【０００３】[0003]
【従来の技術】従来、特公昭６１−５５４８１号公報に
あるように、粉体を種々のフッ素化合物にて表面処理す
ることで、粉体表面にフルオロアルキル鎖を導入し、粉
体に撥水撥油性の性質を付加し、粉体が皮脂や汗に濡れ
ないことを利用して化粧持続性に優れた化粧料の開発が
行われていた。2. Description of the Related Art Conventionally, as described in JP-B-61-55481, a powder is subjected to a surface treatment with various fluorine compounds to introduce a fluoroalkyl chain into the powder surface and to impart water repellency to the powder. The development of cosmetics that have an oil-repellent property and have excellent makeup lasting properties has been carried out by utilizing the fact that powder does not get wet with sebum or sweat.
【０００４】[0004]
【発明が解決しようとする課題】ここで、粉体と皮膚と
の結合は、物理的な付着力が中心となる場合が多いが、
大量の汗、皮脂に対してはそれらの結合を維持できず、
結果的に経時で化粧膜が薄くなるという問題が発生し
た。Here, the bond between the powder and the skin is often centered on the physical adhesive force.
For a large amount of sweat and sebum, they cannot maintain their binding,
As a result, there has been a problem that the decorative film becomes thin with time.
【０００５】これに対して、特公平６−１０２６０７号
公報にあるように、フッ素処理粉体とフッ素系油剤を組
み合わせることも考えられるが、皮膚との結合力を飛躍
的にアップし、化粧持続性に優れた化粧料を開発するま
でには至らなかった。On the other hand, as disclosed in Japanese Patent Publication No. 6-102607, it is conceivable to combine a fluorinated powder with a fluorinated oil, but the binding force with the skin is dramatically increased, and the makeup lasting time is increased. It was not enough to develop cosmetics with excellent properties.
【０００６】[0006]
【課題を解決するための手段】上記実情に鑑み、鋭意研
究した結果、フッ素アルキル・（ポリ）グリセリン共変
性シリコーン化合物が水を保持した場合、増粘またはゲ
ル化する性質を有すること、一定量の水を保持した後
は、強い撥水撥油性を有することを見出し、この性質を
表面処理によって粉体に与えることで、耐皮脂性、耐水
性、耐久性に優れた化粧料が得られることを見出だし、
さらに水を使用しない化粧料の場合、フッ素アルキル・
（ポリ）グリセリン共変性シリコーン化合物は粉体表面
の油剤の一部として働き、塗布時の感触調製剤としての
役割をはたすが、一定時間、皮膚から水分を供給された
後では、増粘して皮膚との結合力を増すことで、化粧持
続性向上のための役割をはたすという知見を得た。DISCLOSURE OF THE INVENTION In view of the above circumstances, as a result of intensive studies, it has been found that a fluorine-alkyl / (poly) glycerin co-modified silicone compound has a property of thickening or gelling when water is retained. After retaining the water of the above, it was found that it has strong water and oil repellency, and by giving this property to the powder by surface treatment, a cosmetic with excellent sebum resistance, water resistance and durability can be obtained. And find
In the case of cosmetics that do not use water,
The (poly) glycerin co-modified silicone compound acts as a part of the oil agent on the powder surface and plays a role as a feel adjusting agent at the time of application. However, after a certain amount of moisture is supplied from the skin, the viscosity increases. It has been found that increasing the bonding strength with the skin plays a role in improving the persistence of makeup.
【０００７】また、フッ素アルキル・（ポリ）グリセリ
ン共変性シリコーン化合物はフッ素アルキル部分、（ポ
リ）グリセリン部分、シリコーン部分を有することか
ら、これらの構成成分と親和性のある表面処理、例えば
未処理粉体の表面水酸基を利用したり、フッ素化合物処
理、シリコーン処理、アミノ酸処理などと同時に行なっ
たり、それらの表面処理を事前に行なった後に、フッ素
アルキル・（ポリ）グリセリン共変性シリコーン化合物
を表面処理することによっても、感触面や持続性の面で
同様な特徴が得られることを見出だし、本発明を完成す
るに至った。Further, since the fluorine-alkyl / (poly) glycerin co-modified silicone compound has a fluorine-alkyl portion, a (poly) glycerin portion and a silicone portion, a surface treatment compatible with these components, for example, an untreated powder Utilizing surface hydroxyl groups of the body, simultaneous treatment with a fluorine compound, silicone treatment, amino acid treatment, etc., or after performing those surface treatments beforehand, surface treatment with a fluorine alkyl / (poly) glycerin co-modified silicone compound In this way, it was found that similar characteristics can be obtained in terms of feel and durability, and the present invention has been completed.
【０００８】すなわち、本発明は、下記一般式（１）で
示される、フッ素アルキル・（ポリ）グリセリン共変性
シリコーン化合物にて表面処理された改質粉体、及びそ
れを含有する化粧料である。[0008] That is, the present invention is a modified powder surface-treated with a fluorine-alkyl / (poly) glycerin co-modified silicone compound represented by the following general formula (1), and a cosmetic containing the same. .
【０００９】[0009]
【化５】 Embedded image
【００１０】［式中、Ｒ1〜Ｒ12は同一又は異なっても
良く、炭素数１〜１０のアルキル基、フェニル基を示
し、そのうち、少なくとも１つはフッ素置換アルキル基
であり、またさらに、少なくとも１つは下記式（Ａ）、
（Ｂ）又は（Ｃ）[Wherein, R 1 to R 12 may be the same or different and represent an alkyl group having 1 to 10 carbon atoms or a phenyl group, at least one of which is a fluorine-substituted alkyl group; At least one of the following formula (A):
(B) or (C)
【００１１】[0011]
【化６】 Embedded image
【００１２】[0012]
【化７】 Embedded image
【００１３】[0013]
【化８】 Embedded image
【００１４】（但し、Ｑは炭素数１〜１０の２価炭化水
素基、ｌは１〜２０、ｍは１〜２０の正の整数であ
る。）で示される基、ｐ、ｑ、ｒはそれぞれ０以上の整
数であるが、ｐ＝ｑ＝０、ｒ≠０のときＲ1〜Ｒ3、Ｒ8
〜Ｒ12の少なくとも１つはフッ素置換アルキル基、及び
上記式（Ａ）、（Ｂ）又は（Ｃ）で表わされる基を示
し、ｐ＝ｒ＝０、ｑ≠０のときＲ1〜Ｒ3、Ｒ6〜Ｒ7、Ｒ
10〜Ｒ12の少なくとも１つはフッ素置換アルキル基、及
び上記式（Ａ）、（Ｂ）又は（Ｃ）で表わされる基を示
し、ｐ≠０、ｑ＝ｒ＝０のときＲ1〜Ｒ5、Ｒ10〜Ｒ12の
少なくとも１つはフッ素置換アルキル基、及び上記式
（Ａ）、（Ｂ）又は（Ｃ）で表わされる基を示し、ｐ＝
０、ｑ＝ｒ≠０、のときＲ1〜Ｒ3、Ｒ6〜Ｒ15の少なく
とも１つはフッ素置換アルキル基、及び上記式（Ａ）、
（Ｂ）又は（Ｃ）で表わされる基を示し、ｐ＝ｒ≠０、
ｑ＝０のときＲ1〜Ｒ5、Ｒ8〜Ｒ12の少なくとも１つは
フッ素置換アルキル基、及び上記式（Ａ）、（Ｂ）又は
（Ｃ）で表わされる基を示し、ｐ＝ｑ≠０、ｒ＝０のと
きＲ1〜Ｒ7、Ｒ10〜Ｒ12の少なくとも１つはフッ素置換
アルキル基、及び上記式（Ａ）、（Ｂ）又は（Ｃ）で表
わされる基を示し、ｐ＝ｑ＝ｒ＝０のときＲ1〜Ｒ3、Ｒ
10〜Ｒ12の少なくとも１つはフッ素置換アルキル基、及
び上記式（Ａ）、（Ｂ）又は（Ｃ）で表わされる基を示
す。］ 以下、本発明について詳細に説明する。(Wherein Q is a divalent hydrocarbon group having 1 to 10 carbon atoms, l is a positive integer of 1 to 20 and m is a positive integer of 1 to 20), and p, q, and r are Each is an integer of 0 or more, but when p = q = 0 and r ≠ 0, R 1 to R 3 and R 8
At least one of R 1 to R 12 represents a fluorine-substituted alkyl group or a group represented by the above formula (A), (B) or (C), and when p = r = 0 and q ≠ 0, R 1 to R 3 , R 6 -R 7 , R
At least one of 10 to R 12 represents a fluorine-substituted alkyl group and a group represented by the above formula (A), (B) or (C), and when p ≠ 0 and q = r = 0, R 1 to R 12 5 , at least one of R 10 to R 12 represents a fluorine-substituted alkyl group and a group represented by the above formula (A), (B) or (C), and p =
0, when q = r ≠ 0, at least one of R 1 to R 3 and R 6 to R 15 is a fluorine-substituted alkyl group, and the above formula (A);
A group represented by (B) or (C), p = r ≠ 0,
When q = 0, at least one of R 1 to R 5 and R 8 to R 12 represents a fluorine-substituted alkyl group and a group represented by the above formula (A), (B) or (C), and p = q When ≠ 0 and r = 0, at least one of R 1 to R 7 and R 10 to R 12 represents a fluorine-substituted alkyl group and a group represented by the above formula (A), (B) or (C); When p = q = r = 0, R 1 to R 3 , R
At least one fluorine-substituted alkyl group having 10 to R 12, and the above formula (A), a group represented by (B) or (C). Hereinafter, the present invention will be described in detail.
【００１５】本発明で用いられるフッ素アルキル・（ポ
リ）グリセリン共変性シリコーン化合物は、上記一般式
（１）に示すごとく、モノグリセリン及びまたはポリグ
リセリンがスペーサーを介してシリコーン鎖に結合した
化合物である。上記一般式（１）で示される化合物にお
いて、Ｒ1〜Ｒ12は同一又は異なっても良く、炭素数１
〜１０のアルキル基、フェニル基を示し、例えば、メチ
ル基、エチル基、プロピル基、ブチル基、ペンチル基、
ヘキシル基、ヘプチル基、オクチル基、ノニル基、デケ
ル基、シクロペンチル基、シクロヘキシル基、フェニル
基、トリル基等が挙げられ、また、Ｒ1〜Ｒ12の少なく
とも１つはフッ素置換アルキル基であり、例えば、トリ
フルオロプロピル基、ノナフルオロヘキシル基、ヘプタ
デカフルオロデシル基等が挙げられ、またさらにＲ1〜
Ｒ12の少なくとも１つは上記式（Ａ）、（Ｂ）又は
（Ｃ）で示される基であるが、モノグリセリン、ジグリ
セリン、トリグリセリン、テトラグリセリン等が挙げら
れる。The fluorine-alkyl / (poly) glycerin co-modified silicone compound used in the present invention is a compound in which monoglycerin and / or polyglycerin are bonded to a silicone chain via a spacer as shown in the above general formula (1). . In the compound represented by the general formula (1), R 1 to R 12 may be the same or different, and have 1 carbon atom.
Represents an alkyl group or a phenyl group, for example, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group,
Hexyl group, heptyl group, octyl group, nonyl group, dekel group, cyclopentyl group, cyclohexyl group, phenyl group, tolyl group, and the like, and at least one of R 1 to R 12 is a fluorine-substituted alkyl group, For example, trifluoropropyl group, nonafluorohexyl group, heptadecafluorodecyl group and the like, or even R 1 ~
At least one of R 12 is a group represented by the above formula (A), (B) or (C), and examples thereof include monoglycerin, diglycerin, triglycerin, and tetraglycerin.
【００１６】この上記一般式（１）に示されるフッ素ア
ルキル・（ポリ）グリセリン共変性シリコーン化合物で
表面処理される粉体としては、従来化粧品に使用される
無機、または有機粉体を指し、レーキ色素、染料、ナイ
ロンパウダー、シルクパウダーなどの高分子、有色顔
料、白色顔料、体質顔料、パール顔料、金属塩、無機粉
体、金属石鹸、微粒子酸化亜鉛、微粒子酸化チタン、微
粒子酸化鉄、アルミナ処理微粒子酸化チタン、シリカ処
理微粒子酸化チタンなどが挙げられる。これらの粉体は
上記一般式（１）と同時に一般の表面処理しても良く、
また、一般の表面処理をした後で、上記一般式（１）で
さらに表面処理しても良い。The powder to be surface-treated with the fluorine-alkyl / (poly) glycerin co-modified silicone compound represented by the general formula (1) refers to an inorganic or organic powder conventionally used in cosmetics. Dyes, dyes, polymers such as nylon powder and silk powder, colored pigments, white pigments, extender pigments, pearl pigments, metal salts, inorganic powders, metal soaps, particulate zinc oxide, particulate titanium oxide, particulate iron oxide, alumina treated Fine particle titanium oxide, silica-treated fine particle titanium oxide, and the like. These powders may be subjected to a general surface treatment simultaneously with the general formula (1),
After performing the general surface treatment, the surface may be further subjected to the general formula (1).
【００１７】表面処理の種類としては、従来公知の表面
処理、例えばフッ素化合物処理、シリコーン処理、ペン
ダント処理、シランカップリング剤処理、チタンカップ
リング剤処理、油剤処理、Ｎ−アシル化リジン処理、ポ
リカルボン酸処理、金属石鹸処理、アミノ酸処理、無機
化合物処理、生体抽出成分処理、プラズマ処理、メカノ
ケミカル処理などが挙げられる。The types of surface treatment include conventionally known surface treatments such as fluorine compound treatment, silicone treatment, pendant treatment, silane coupling agent treatment, titanium coupling agent treatment, oil agent treatment, N-acylated lysine treatment, poly Examples include carboxylic acid treatment, metal soap treatment, amino acid treatment, inorganic compound treatment, biological extraction component treatment, plasma treatment, mechanochemical treatment, and the like.
【００１８】表面処理の方法としては、湿式法、乾式
法、メカノケミカル法等が挙げられる。Examples of the surface treatment method include a wet method, a dry method, a mechanochemical method and the like.
【００１９】表面処理におけるフッ素アルキル・（ポ
リ）グリセリン共変性シリコーン化合物と未処理粉体ま
たは処理粉体との混合割合は、粉体の吸油量や比表面積
によって異なるが、未処理粉体または処理粉体の重量に
対して０．１〜１００重量％（以下、単に「％」と記
す）が好ましく、更に好ましくは、１〜１５％である。
０．１％未満では処理が不充分なことがあり、１００％
を超えると、感触が悪くなる場合がある。The mixing ratio of the fluorine-alkyl / (poly) glycerin co-modified silicone compound and the untreated powder or treated powder in the surface treatment varies depending on the oil absorption and the specific surface area of the powder. It is preferably from 0.1 to 100% by weight (hereinafter simply referred to as "%"), more preferably from 1 to 15%, based on the weight of the powder.
If it is less than 0.1%, the treatment may be insufficient, and 100%
If it exceeds, the touch may be poor.
【００２０】本発明の改質粉体を化粧料に配合する場
合、化粧料の剤型により異なるが、化粧料に対して、改
質粉体を０．１〜９９％を配合するのが好ましい。When the modified powder of the present invention is blended in a cosmetic, the content of the modified powder is preferably 0.1 to 99% with respect to the cosmetic, depending on the form of the cosmetic. .
【００２１】本発明の化粧料としては、ファンデーショ
ン、白粉、プレストパウダー、チークカラー、下地、口
紅、アイシャドウ、アイライナー、ネイルカラー等のメ
ークアップ化粧料、クリーム、乳液、化粧水等の皮膚化
粧料、頭髪化粧料のみならず、パウダースプレーや外用
医薬品などの使用時に感触が問題とされる、皮膚に外用
されるすべての製品を包含する。The cosmetics of the present invention include make-up cosmetics such as foundation, white powder, pressed powder, teak color, base, lipstick, eyeshadow, eyeliner, nail color, and skin cosmetics such as creams, emulsions, and lotions. Not only cosmetics and hair cosmetics, but also all products used externally on the skin, which have a problem when using powder sprays or external medicines.
【００２２】本発明の化粧料では、上記の成分に加え、
本発明の効果を妨げない範囲で通常の化粧料に使用され
る固体、半固体、液状の油剤、水、水溶性高分子、多価
アルコール、溶剤、界面活性剤、粉体、樹脂、有機変性
粘土鉱物、高分子、紫外線吸収剤、保湿剤、防腐剤、殺
菌剤、香料、酸化防止剤、美肌用成分、生理活性成分な
どを配合することができる。In the cosmetic of the present invention, in addition to the above components,
Solid, semi-solid, liquid oils, water, water-soluble polymers, polyhydric alcohols, solvents, surfactants, powders, resins, organically modified solid cosmetics used in ordinary cosmetics as long as the effects of the present invention are not impaired. A clay mineral, a polymer, an ultraviolet absorber, a humectant, a preservative, a bactericide, a fragrance, an antioxidant, a beautiful skin component, a physiologically active component, and the like can be added.
【００２３】[0023]
【実施例】以下に本発明を実施例を挙げて説明するが、
本発明はこれらの実施例によって限定されるものではな
い。EXAMPLES The present invention will be described below with reference to examples.
The present invention is not limited by these examples.
【００２４】製造例１ 攪拌機、温度計及び還流冷却器を付したガラス製フラス
コに下記式のグリセリンモノアリルエーテル３８．４
ｇ、Production Example 1 Glycerin monoallyl ether 38.4 of the following formula was placed in a glass flask equipped with a stirrer, thermometer and reflux condenser.
g,
【００２５】[0025]
【化９】 Embedded image
【００２６】及び下記式で表わされるＳｉＨ基含有フッ
素アルキル変性シリコーン２００ｇ、And 200 g of a SiH group-containing fluorine-alkyl-modified silicone represented by the following formula:
【００２７】[0027]
【化１０】 Embedded image
【００２８】イソプロピルアルコール１００ｇ、酢酸カ
リウムの１０％エタノール溶液０．３ｇ及び塩化白金酸
のイソプロピルアルコール溶液（白金濃度２％）０．３
ｇを仕込み、加熱してイソプロピルアルコールの還流温
度で５時間反応を行なった。反応終了後、イソプロピル
アルコールを減圧留去し、下記式のフッ素アルキル・グ
リセリン共変性のシリコーン２１１．４ｇを得た。100 g of isopropyl alcohol, 0.3 g of a 10% ethanol solution of potassium acetate, and 0.3 g of an isopropyl alcohol solution of chloroplatinic acid (platinum concentration: 2%)
g was heated and reacted at the reflux temperature of isopropyl alcohol for 5 hours. After completion of the reaction, isopropyl alcohol was distilled off under reduced pressure to obtain 211.4 g of a fluoroalkyl / glycerin co-modified silicone represented by the following formula.
【００２９】[0029]
【化１１】 Embedded image
【００３０】製造例２ 製造例１のグリセリンモノアリルエーテルを下記式のト
リグリセリンモノアリルエーテル８１．４ｇProduction Example 2 81.4 g of triglycerin monoallyl ether of the following formula was prepared by converting the glycerin monoallyl ether of Production Example 1 to:
【００３１】[0031]
【化１２】 Embedded image
【００３２】に代えた以外は同様の操作を行い、下記式
のフッ素アルキル・ポリグリセリン共変性のシリコーン
２４６．６ｇを得た。The same procedure was repeated except that the above procedure was repeated to obtain 246.6 g of a fluorine-alkyl / polyglycerin co-modified silicone represented by the following formula.
【００３３】[0033]
【化１３】 Embedded image
【００３４】製造例３ 製造例１のグリセリンモノアリルエーテルを下記式のト
リグリセリンモノアリルエーテル８１．４ｇProduction Example 3 81.4 g of triglycerin monoallyl ether of the following formula was prepared by converting the glycerin monoallyl ether of Production Example 1 to:
【化１４】 Embedded image
【００３５】に代えた以外は同様の操作を行い、下記式
のフッ素アルキル・ポリグリセリン共変性のシリコーン
２４６．６ｇを得た。The same procedure was repeated except that the above procedure was repeated to obtain 246.6 g of a fluorine-alkyl / polyglycerin co-modified silicone represented by the following formula.
【００３６】[0036]
【化１５】 Embedded image
【００３７】製造例４ 製造例１のＳｉＨ基含有フッ素アルキル変性シリコーン
を下記式で表わされるＳｉＨ基含有フッ素アルキル変性
シリコーン１９６．３ｇProduction Example 4 196.3 g of the SiH group-containing fluoroalkyl-modified silicone represented by the following formula was prepared from the SiH group-containing fluoroalkyl-modified silicone of Production Example 1.
【００３８】[0038]
【化１６】 Embedded image
【００３９】に代えた以外は、製造例３と同様の操作を
行い、下記式のフッ素アルキル・ポリグリセリン共変性
のシリコーン２４３ｇを得た。The same operation as in Production Example 3 was carried out, except that 243 g of a fluorine-alkyl-polyglycerin co-modified silicone represented by the following formula was obtained.
【００４０】[0040]
【化１７】 Embedded image
【００４１】製造例５ 製造例１のＳｉＨ基含有フッ素アルキル変性シリコーン
を下記式で表わされるＳｉＨ基含有フッ素アルキル変性
シリコーン１４２．３ｇProduction Example 5 142.3 g of a SiH group-containing fluorine-alkyl-modified silicone represented by the following formula was prepared from the SiH group-containing fluorine-alkyl-modified silicone of Production Example 1.
【００４２】[0042]
【化１８】 Embedded image
【００４３】に代えた以外は、製造例３と同様の操作を
行い、下記式のフッ素アルキル・ポリグリセリン共変性
のシリコーン１９４．７ｇを得た。The same operation as in Production Example 3 was carried out, except that the substitution was made, to obtain 194.7 g of a fluorine-alkyl / polyglycerin co-modified silicone represented by the following formula.
【００４４】[0044]
【化１９】 Embedded image
【００４５】実施例１ セリサイト９５部をクロロホルム３００部に分散させた
後、製造例３で得られたフッ素アルキル・グリセリン変
性シリコーン化合物５部を加え攪拌する。クロロホルム
を減圧留去した後、粉砕して改質セリサイトを得た。同
様にして、５％フッ素アルキル・グリセリン共変性シリ
コーン化合物処理酸化チタン、タルク、黄酸化鉄、ベン
ガラ、黒酸化鉄を得た。Example 1 After 95 parts of sericite was dispersed in 300 parts of chloroform, 5 parts of the fluoroalkyl / glycerin-modified silicone compound obtained in Production Example 3 was added and stirred. After chloroform was distilled off under reduced pressure, the residue was pulverized to obtain modified sericite. Similarly, titanium oxide, talc, yellow iron oxide, red iron oxide, black iron oxide treated with a 5% fluorine alkyl / glycerin co-modified silicone compound were obtained.
【００４６】実施例２ ３％メチルハイドロジェンポリシロキサン処理セリサイ
ト９２部をクロロホルム３００部に分散させた後、製造
例２で得られたフッ素アルキル・ポリグリセリン共変性
シリコーン化合物８部を加え攪拌する。クロロホルムを
減圧留去した後、粉砕して改質セリサイトを得た。同様
にして、８％フッ素アルキル・ポリグリセリン共変性シ
リコーン化合物・シリコーン処理酸化チタン、タルク、
黄酸化鉄、ベンガラ、黒酸化鉄を得た。Example 2 92 parts of 3% methylhydrogenpolysiloxane-treated sericite was dispersed in 300 parts of chloroform, and 8 parts of the fluoroalkyl / polyglycerin co-modified silicone compound obtained in Production Example 2 was added and stirred. . After chloroform was distilled off under reduced pressure, the residue was pulverized to obtain modified sericite. Similarly, 8% fluorine alkyl / polyglycerin co-modified silicone compound / silicone-treated titanium oxide, talc,
Yellow iron oxide, red iron oxide and black iron oxide were obtained.
【００４７】実施例３ パーフルオロアルキルリン酸エステル塩５％処理セリサ
イト９６部をクロロホルム３００部に分散させた後、製
造例１で得られたフッ素アルキル・ポリグリセリン共変
性シリコーン化合物４部を加え攪拌する。クロロホルム
を減圧留去した後、粉砕して改質セリサイトを得た。同
様にして、４％フッ素アルキル・ポリグリセリン共変性
シリコーン化合物・パーフルオロアルキル処理酸化チタ
ン、タルク、黄酸化鉄、ベンガラ、黒酸化鉄を得た。Example 3 After 96 parts of sericite treated with 5% perfluoroalkyl phosphate salt was dispersed in 300 parts of chloroform, 4 parts of the fluoroalkyl / polyglycerin co-modified silicone compound obtained in Production Example 1 was added. Stir. After chloroform was distilled off under reduced pressure, the residue was pulverized to obtain modified sericite. Similarly, 4% fluorine alkyl / polyglycerin co-modified silicone compound / perfluoroalkyl treated titanium oxide, talc, yellow iron oxide, red iron oxide and black iron oxide were obtained.
【００４８】実施例４〜６及び比較例１ ファンデーシ
ョン 次の表１に示す各組成のファンデーションを製造し、そ
の使用性について評価した。Examples 4 to 6 and Comparative Example 1 Foundation Foundations having the respective compositions shown in the following Table 1 were produced and their usability was evaluated.
【００４９】[0049]
【表１】 [Table 1]
【００５０】（製造方法） Ａ：成分１〜２４をヘンシルミキサーにて混合する。 Ｂ：成分２５〜２９を混合してＡに加え、更に攪拌す
る。 Ｃ：Ｃをアトマイザーにて粉砕を行なった後、金型に打
型してファンデーションを得た。(Production method) A: Components 1 to 24 are mixed with a Hensyl mixer. B: Components 25 to 29 are mixed, added to A, and further stirred. C: C was pulverized by an atomizer, and then was pressed into a mold to obtain a foundation.
【００５１】（評価方法）女性５０名のパネルにより使
用テストを行ない、肌へののび、付着性の良さ、べたつ
きのなさ、仕上がりの美しさ、化粧持ちの良さについて
下記の基準で評価を行ない、その平均点で判定した。 ［評価基準］ ５点：非常に良好 ４点：良好 ３点：普通 ２点：やや不良 １点：不良 ［判定］ ◎：平均点４．５以上 ○：平均点３．５以上４．５未満 △：平均点２．５以上３．５未満 ×：平均点２．５未満 得られた結果を表２に示す。(Evaluation method) A use test was conducted by a panel of 50 women, and evaluation was made on the following criteria for spreadability, good adhesion, non-stickiness, beautiful finish, and good makeup lasting. The judgment was made based on the average score. [Evaluation criteria] 5 points: Very good 4 points: Good 3 points: Normal 2 points: Somewhat poor 1 point: Poor [Judgment] ：: Average score of 4.5 or more ○: Average score of 3.5 or more and less than 4.5 Δ: Average score of 2.5 or more and less than 3.5 ×: Average score of less than 2.5 The obtained results are shown in Table 2.
【００５２】[0052]
【表２】 [Table 2]
【００５３】表２の結果から明らかなように、本発明に
係わるフッ素アルキル・（ポリ）グリセリン共変性シリ
コーン化合物で処理した粉体を配合した実施例１〜３
は、未処理の粉体を配合した比較例１に比べて肌へのの
び、付着性に優れ、べたつきがなく、仕上がりの美しい
ファンデーションであり、また、化粧持ちも非常に良い
ものであることがわかった。As is apparent from the results in Table 2, Examples 1 to 3 in which powders treated with the fluorine-alkyl / (poly) glycerin co-modified silicone compound according to the present invention were blended.
Is a beautiful foundation with excellent spreadability and adhesion to the skin, non-stickiness, and a beautiful finish, as compared with Comparative Example 1 in which untreated powder is blended. all right.
【００５４】[0054]
【発明の効果】以上詳述したように、フッ素アルキル・
（ポリ）グリセリン共変性シリコーン化合物で表面処理
された改質粉体を配合した化粧料は、撥水撥油性、耐久
性に優れ、化粧持ちの非常に良いものである。As described in detail above, the fluorine alkyl
A cosmetic containing a modified powder surface-treated with a (poly) glycerin co-modified silicone compound is excellent in water and oil repellency and durability, and has a very long lasting makeup.
─────────────────────────────────────────────────────
────────────────────────────────────────────────── ───
【手続補正書】[Procedure amendment]
【提出日】平成９年１２月９日[Submission date] December 9, 1997
【手続補正１】[Procedure amendment 1]
【補正対象書類名】明細書[Document name to be amended] Statement
【補正対象項目名】００４９[Correction target item name] 0049
【補正方法】変更[Correction method] Change
【補正内容】[Correction contents]
【００４９】[0049]
【表１】 [Table 1]
【手続補正２】[Procedure amendment 2]
【補正対象書類名】明細書[Document name to be amended] Statement
【補正対象項目名】００５３[Correction target item name] 0053
【補正方法】変更[Correction method] Change
【補正内容】[Correction contents]
【００５３】表２の結果から明らかなように、本発明に
係わるフッ素アルキル・（ポリ）グリセリン共変性シリ
コーン化合物で処理した粉体を配合した実施例４〜６
は、未処理の粉体を配合した比較例１に比べて肌へのの
び、付着性に優れ、べたつきがなく、仕上がりの美しい
ファンデーションであり、また、化粧持ちも非常に良い
ものであることがわかった。As is clear from the results in Table 2, the present invention
Related fluorine alkyl / (poly) glycerin co-modified silicone
Example of compounding powder treated with corn compound4~6
Is more effective on skin than Comparative Example 1 in which untreated powder is blended.
And excellent adhesion, no stickiness, beautiful finish
It is a foundation and the makeup lasts very well
Turned out to be something.
Claims (2)
ルキル・（ポリ）グリセリン共変性シリコーン化合物に
て表面処理されたことを特徴とする改質粉体。 【化１】 ［式中、Ｒ1〜Ｒ12は同一又は異なっても良く、炭素数
１〜１０のアルキル基、フェニル基を示し、そのうち、
少なくとも１つはフッ素置換アルキル基であり、またさ
らに、少なくとも１つは下記式（Ａ）、（Ｂ）又は
（Ｃ） 【化２】 【化３】 【化４】 （但し、Ｑは炭素数１〜１０の２価炭化水素基、ｌは１
〜２０、ｍは１〜２０の正の整数である。）で示される
基、ｐ、ｑ、ｒはそれぞれ０以上の整数であるが、ｐ＝
ｑ＝０、ｒ≠０のときＲ1〜Ｒ3、Ｒ8〜Ｒ12の少なくと
も１つはフッ素置換アルキル基、及び上記式（Ａ）、
（Ｂ）又は（Ｃ）で表わされる基を示し、ｐ＝ｒ＝０、
ｑ≠０のときＲ1〜Ｒ3、Ｒ6〜Ｒ7、Ｒ10〜Ｒ12の少なく
とも１つはフッ素置換アルキル基、及び上記式（Ａ）、
（Ｂ）又は（Ｃ）で表わされる基を示し、ｐ≠０、ｑ＝
ｒ＝０のときＲ1〜Ｒ5、Ｒ10〜Ｒ12の少なくとも１つは
フッ素置換アルキル基、及び上記式（Ａ）、（Ｂ）又は
（Ｃ）で表わされる基を示し、ｐ＝０、ｑ＝ｒ≠０、の
ときＲ1〜Ｒ3、Ｒ6〜Ｒ15の少なくとも１つはフッ素置
換アルキル基、及び上記式（Ａ）、（Ｂ）又は（Ｃ）で
表わされる基を示し、ｐ＝ｒ≠０、ｑ＝０のときＲ1〜
Ｒ5、Ｒ8〜Ｒ12の少なくとも１つはフッ素置換アルキル
基、及び上記式（Ａ）、（Ｂ）又は（Ｃ）で表わされる
基を示し、ｐ＝ｑ≠０、ｒ＝０のときＲ1〜Ｒ7、Ｒ10〜
Ｒ12の少なくとも１つはフッ素置換アルキル基、及び上
記式（Ａ）、（Ｂ）又は（Ｃ）で表わされる基を示し、
ｐ＝ｑ＝ｒ＝０のときＲ1〜Ｒ3、Ｒ10〜Ｒ12の少なくと
も１つはフッ素置換アルキル基、及び上記式（Ａ）、
（Ｂ）又は（Ｃ）で表わされる基を示す。］1. A modified powder which is surface-treated with a fluorine-alkyl / (poly) glycerin co-modified silicone compound represented by the following general formula (1). Embedded image [Wherein, R 1 to R 12 may be the same or different and represent an alkyl group having 1 to 10 carbon atoms or a phenyl group;
At least one is a fluorine-substituted alkyl group, and further, at least one is of the following formula (A), (B) or (C): Embedded image Embedded image (However, Q is a divalent hydrocarbon group having 1 to 10 carbon atoms, l is 1
-20 and m are positive integers of 1-20. ), P, q, and r are each an integer of 0 or more.
When q = 0 and r ≠ 0, at least one of R 1 to R 3 and R 8 to R 12 is a fluorine-substituted alkyl group, and the above formula (A)
A group represented by (B) or (C), p = r = 0,
When q ≠ 0, at least one of R 1 to R 3 , R 6 to R 7 , and R 10 to R 12 is a fluorine-substituted alkyl group, and the above formula (A);
A group represented by (B) or (C), p ≠ 0, q =
When r = 0, at least one of R 1 to R 5 and R 10 to R 12 represents a fluorine-substituted alkyl group and a group represented by the above formula (A), (B) or (C), and p = 0 , Q = r ≠ 0, at least one of R 1 to R 3 and R 6 to R 15 represents a fluorine-substituted alkyl group and a group represented by the above formula (A), (B) or (C) , P = r ≠ 0, q 1 = 0
At least one of R 5 and R 8 to R 12 represents a fluorine-substituted alkyl group or a group represented by the above formula (A), (B) or (C), and when p = q ≠ 0 and r = 0 R 1 to R 7 , R 10 to
At least one of R 12 represents a fluorine-substituted alkyl group and a group represented by the above formula (A), (B) or (C);
When p = q = r = 0, at least one of R 1 to R 3 and R 10 to R 12 is a fluorine-substituted alkyl group, and the above formula (A)
It represents a group represented by (B) or (C). ]
を特徴とする化粧料。2. A cosmetic comprising the modified powder according to claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13611697A JP3496133B2 (en) | 1997-05-09 | 1997-05-09 | Modified powder and cosmetic containing it |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13611697A JP3496133B2 (en) | 1997-05-09 | 1997-05-09 | Modified powder and cosmetic containing it |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH10310508A true JPH10310508A (en) | 1998-11-24 |
| JP3496133B2 JP3496133B2 (en) | 2004-02-09 |
Family
ID=15167684
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13611697A Expired - Lifetime JP3496133B2 (en) | 1997-05-09 | 1997-05-09 | Modified powder and cosmetic containing it |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3496133B2 (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002008336A1 (en) * | 2000-07-21 | 2002-01-31 | Shin-Etsu Chemical Co., Ltd. | Powder composition, dispersion of the powder in oil, and cosmetic preparation containing these |
| US7771709B2 (en) | 2003-07-07 | 2010-08-10 | Shin-Etsu Chemical Co., Ltd. | Alternating copolymer of organopolysiloxane with grycerol derivative and a cosmetic comprising the same |
| WO2011049248A1 (en) | 2009-10-23 | 2011-04-28 | 東レ・ダウコーニング株式会社 | Novel co-modified organopolysiloxane |
| WO2014200111A1 (en) * | 2013-06-13 | 2014-12-18 | 東レ・ダウコーニング株式会社 | Silicone modified by long-chain hydrocarbon group-containing diglycerin derivative, and use thereof |
| US9133309B2 (en) | 2009-10-23 | 2015-09-15 | Dow Corning Toray Co., Ltd. | Organopolysiloxane copolymer |
| US9580600B2 (en) | 2009-10-23 | 2017-02-28 | Dow Conring Toray Co., Ltd. | Thickening or gelling agent for oily raw materials |
| US10406092B2 (en) | 2012-12-28 | 2019-09-10 | Dow Silicones Corporation | Method for producing transparent or semi-transparent liquid glycerin-derivative-modified silicone composition |
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Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002008336A1 (en) * | 2000-07-21 | 2002-01-31 | Shin-Etsu Chemical Co., Ltd. | Powder composition, dispersion of the powder in oil, and cosmetic preparation containing these |
| JP2002038013A (en) * | 2000-07-21 | 2002-02-06 | Shin Etsu Chem Co Ltd | Powder composition, its powder-in-oil dispersion and cosmetic containing the same |
| US7771709B2 (en) | 2003-07-07 | 2010-08-10 | Shin-Etsu Chemical Co., Ltd. | Alternating copolymer of organopolysiloxane with grycerol derivative and a cosmetic comprising the same |
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| US8784787B2 (en) | 2009-10-23 | 2014-07-22 | Dow Corning Toray Co., Ltd. | Co-modified organopolysiloxane |
| US9133309B2 (en) | 2009-10-23 | 2015-09-15 | Dow Corning Toray Co., Ltd. | Organopolysiloxane copolymer |
| US9580600B2 (en) | 2009-10-23 | 2017-02-28 | Dow Conring Toray Co., Ltd. | Thickening or gelling agent for oily raw materials |
| US10406092B2 (en) | 2012-12-28 | 2019-09-10 | Dow Silicones Corporation | Method for producing transparent or semi-transparent liquid glycerin-derivative-modified silicone composition |
| WO2014200111A1 (en) * | 2013-06-13 | 2014-12-18 | 東レ・ダウコーニング株式会社 | Silicone modified by long-chain hydrocarbon group-containing diglycerin derivative, and use thereof |
| CN105452342A (en) * | 2013-06-13 | 2016-03-30 | 道康宁东丽株式会社 | Silicone modified by long-chain hydrocarbon group-containing diglycerin derivative, and use thereof |
| US9783643B2 (en) | 2013-06-13 | 2017-10-10 | Dow Corning Toray Co., Ltd. | Silicone modified by long-chain hydrocarbon group-containing diglycerin derivative, and use thereof |
| CN105452342B (en) * | 2013-06-13 | 2018-10-12 | 道康宁东丽株式会社 | The derivative modified organosilicon of diglycerol containing long chain hydrocarbon groups and its application |
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