JPH06305933A - Oily solid cosmetic - Google Patents

Oily solid cosmetic

Info

Publication number
JPH06305933A
JPH06305933A JP9405093A JP9405093A JPH06305933A JP H06305933 A JPH06305933 A JP H06305933A JP 9405093 A JP9405093 A JP 9405093A JP 9405093 A JP9405093 A JP 9405093A JP H06305933 A JPH06305933 A JP H06305933A
Authority
JP
Japan
Prior art keywords
glyceryl ether
alkyl glyceryl
oily
formula
solid cosmetic
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
Application number
JP9405093A
Other languages
Japanese (ja)
Other versions
JP3477222B2 (en
Inventor
Kazuhiko Daijima
和彦 廼島
Momoko Shimizu
桃子 清水
Yuko Yago
祐子 矢後
Ryuji Hasegawa
隆二 長谷川
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Kao Corp
Original Assignee
Kao Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Kao Corp filed Critical Kao Corp
Priority to JP09405093A priority Critical patent/JP3477222B2/en
Publication of JPH06305933A publication Critical patent/JPH06305933A/en
Application granted granted Critical
Publication of JP3477222B2 publication Critical patent/JP3477222B2/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Abstract

PURPOSE:To provide an oily solid cosmetic containing a specific alkylglyceryl ether-modified silicone as an essential ingredient, excellent in cosmetic retainability, good in both touch and finish, and useful as a lip stick, a make-up cosmetic such as a foundation, etc. CONSTITUTION:An oily solid cosmetic containing one kind or more of alkyl glyceryl ether-modified silicones. The alkylglyceryl ether is especially preferably an alkylglyceryl ether-modified silicone of formula I [at least one of R<1>-R<12> is alkylglyceryl ether of formula II (Q is 3-20C divalent hydrocarbon; R<13>, R<14> are H, 1-32C hydrocarbon), and the others are H, 1-32C hydrocarbon, phenyl; p-r are such numbers that the content of the group of the formula II is 1-50wt.%]. The addition of a solid, semi-solid or liquid oily raw material (e.g. vegetable wax, lanolin wax, petrolatum) in addition of the silicone is preferable.

Description

【発明の詳細な説明】Detailed Description of the Invention

【0001】[0001]

【産業上の利用分野】本発明は、使用感、仕上り及び化
粧持ちのいずれにも優れた油性固型化粧料に関する。
BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an oily solid cosmetic composition which is excellent in feeling of use, finish and makeup retention.

【0002】[0002]

【従来の技術】従来から、口紅、アイシャドウ、アイラ
イナー及び油性ファンデーション等の油性メイクアップ
化粧料は、肌に塗布後、化粧持ちが悪く、衣服に付着し
たり、にじみが生じやすいという欠点を有していた。
2. Description of the Related Art Conventionally, oily makeup cosmetics such as lipsticks, eye shadows, eyeliners and oily foundations have the drawback that after applying to the skin, the makeup lasts poorly and is liable to adhere to clothes or bleed. Had.

【0003】この欠点を解消し、化粧持ちを良くするた
め、従来より種々の検討がなされてきた。その例とし
て、揮発性油剤を配合し、塗布後、該油剤が揮散し、塗
布面に色材及びワックスが残るようにし、化粧持ちを改
善しようとする試み;並びに揮発性油剤中にポリマー等
の皮膜形成剤を溶解せしめたものを配合し、これを、塗
布、乾燥することにより皮膚表面にポリマー皮膜を形成
させ、化粧持ちを改善せんとする試み等があった。
In order to eliminate this drawback and improve makeup retention, various studies have been made in the past. As an example, a volatile oil agent is blended, and after application, the oil agent is volatilized so that the coloring material and the wax remain on the coated surface, and an attempt to improve the durability of the makeup; and a polymer such as a polymer in the volatile oil agent. There has been an attempt to improve the durability of makeup by blending a film-forming agent dissolved therein and applying and drying it to form a polymer film on the skin surface.

【0004】しかしながら、このように揮発性油剤を用
いて化粧持ちを改善しようとした化粧料は、塗布後のつ
やが経時的に落ちるという欠点があり、特に口紅におい
ては問題となっていた。更に経日的に揮発性油剤が揮散
するため、口紅のやせが発生し、製品の経時安定性の面
でも問題があった。
However, the cosmetics which are intended to improve the makeup lasting by using the volatile oil agent have a drawback that the gloss after application is deteriorated with time, which is a problem especially in lipstick. Further, since the volatile oily agent volatilizes over time, thinning of the lipstick occurs and there is a problem in terms of stability of the product over time.

【0005】[0005]

【発明が解決しようとする課題】従って、本発明の目的
は、上記欠点がなく化粧持ちに優れ、更に使用感、仕上
りが良好な油性固型化粧料を提供することにある。
SUMMARY OF THE INVENTION Therefore, an object of the present invention is to provide an oily solid cosmetic composition which does not have the above-mentioned drawbacks, is excellent in makeup retention, and has a good feeling in use and a good finish.

【0006】[0006]

【課題を解決するための手段】本発明者は、上記実状に
鑑み鋭意研究を行った結果、アルキルグリセリルエーテ
ル変性シリコーンを配合した固型化粧料が化粧持ちに優
れ、且つ使用感、仕上り性共に良好であることを見出
し、本発明を完成した。
Means for Solving the Problems As a result of intensive studies in view of the above situation, the present inventor has found that a solid cosmetic containing an alkyl glyceryl ether-modified silicone is excellent in makeup lasting and has good feeling and finish. The inventors have found that it is good and completed the present invention.

【0007】すなわち、本発明はアルキルグリセリルエ
ーテル変性シリコーンの一種又は二種以上(以下、
(A)成分という)を含有する油性固型化粧料を提供す
るものである。
That is, the present invention is one or more of alkyl glyceryl ether modified silicones (hereinafter,
An oily solid cosmetic containing (A) component is provided.

【0008】本発明における(A)成分のアルキルグリ
セリルエーテル変性シリコーンは、油性成分として配合
されるものである。従って、アルキルグリセリルエーテ
ル変性シリコーン(A)は、油状物となるようなアルキ
ルグリセリルエーテル変性度を有するもの、すなわち、
アルキルグリセリルエーテル変性度の少ないものの方が
好ましい。
The (A) component alkyl glyceryl ether-modified silicone of the present invention is blended as an oil component. Therefore, the alkyl glyceryl ether-modified silicone (A) has a degree of alkyl glyceryl ether modification such that it becomes an oil, that is,
An alkylglyceryl ether having a low degree of modification is preferable.

【0009】かかる好ましいアルキルグリセリルエーテ
ル変性シリコーンを具体的に示すと、以下の一般式
(1)で表わされるものが挙げられる。
Specific examples of the preferred alkyl glyceryl ether-modified silicone include those represented by the following general formula (1).

【0010】[0010]

【化2】 [Chemical 2]

【0011】(式中、Qは炭素数3〜20の二価の炭化
水素基を示し、R13及びR14は同一又は異なって水素原
子又は炭素数1〜32の直鎖又は分岐鎖の炭化水素基を
示す)で表わされるアルキルグリセリルエーテル基を示
し、残りは、それぞれ水素原子、炭素数1〜32の直鎖
又は分岐鎖の炭化水素基又はフェニル基を示し、p、q
及びrは分子中における一般式(2)で表わされるアル
キルグリセリルエーテル基の含有量が1〜50重量%と
なる数を示す〕
(In the formula, Q represents a divalent hydrocarbon group having 3 to 20 carbon atoms, and R 13 and R 14 are the same or different and each is a hydrogen atom or a linear or branched carbon atom having 1 to 32 carbon atoms. An alkyl glyceryl ether group represented by the formula (1) represents a hydrogen group), the rest each represent a hydrogen atom, a linear or branched hydrocarbon group having 1 to 32 carbon atoms or a phenyl group, and p, q
And r represent the number such that the content of the alkyl glyceryl ether group represented by the general formula (2) in the molecule becomes 1 to 50% by weight.

【0012】更に好ましいものを具体的に示すと次の一
般式(3)〜(6)で表わされるものが挙げられる。
Specific examples of the more preferable ones include those represented by the following general formulas (3) to (6).

【0013】[0013]

【化3】 [Chemical 3]

【0014】〔式中、R1 〜R9 、Q、R13、R14、p
及びqは前記と同じ意味を示す。但し、同一分子内に存
する複数個のR13、R14はそれぞれ異なるものであって
もよい〕
[In the formula, R 1 to R 9 , Q, R 13 , R 14 and p
And q have the same meaning as described above. However, a plurality of R 13 and R 14 existing in the same molecule may be different from each other.]

【0015】前述の一般式(1)、(3)〜(6)にお
いて、Qで示される炭素数3〜20の二価炭化水素基と
しては、トリメチレン、テトラメチレン、ペンタメチレ
ン、ヘキサメチレン、ヘプタメチレン、オクタメチレ
ン、ノナメチレン、デカメチレン、ウンデカメチレン、
ドデカメチレン、テトラデカメチレン、ヘキサデカメチ
レン、オクタデカメチレン等の直鎖アルキレン基;プロ
ピレン、2−メチルトリメチレン、2−メチルテトラメ
チレン、2−メチルペンタメチレン、3−メチルペンタ
メチレン等の分岐鎖アルキレン基等が挙げられる。
In the above general formulas (1), (3) to (6), the divalent hydrocarbon group represented by Q and having 3 to 20 carbon atoms is trimethylene, tetramethylene, pentamethylene, hexamethylene or hepta. Methylene, octamethylene, nonamethylene, decamethylene, undecamethylene,
Linear alkylene groups such as dodecamethylene, tetradecamethylene, hexadecamethylene and octadecamethylene; branched chains such as propylene, 2-methyltrimethylene, 2-methyltetramethylene, 2-methylpentamethylene, 3-methylpentamethylene Examples thereof include alkylene groups.

【0016】また、R1 〜R14の定義中、炭素数1〜3
2の直鎖又は分岐鎖の炭化水素基としては、メチル、エ
チル、プロピル、ブチル、ペンチル、ヘキシル、オクチ
ル、デシル、ドデシル、テトラデシル、ヘキサデシル、
オクタデシル、エイコシル、ドエイコシル、テトラエイ
コシル、ヘキサエイコシル、オクタエイコシル、トリア
コンチル等の直鎖アルキル基;イソプロピル、sec−
ブチル、tert−ブチル、ネオペンチル、1−エチル
プロピル、1−ヘプチルデシル等の分岐鎖アルキル基な
どが挙げられる。本発明において、R1 〜R12は炭素数
1〜25の直鎖又は分岐鎖の炭化水素基(但し、一部が
水素原子であってもよい)が好ましく、特に炭素数1〜
22の直鎖又は分岐鎖の炭化水素基(但し、一部が水素
原子であってもよい)が好ましい。また、R13、R14
水素原子又は炭素数1〜5の炭化水素基が好ましく、特
に水素原子が好ましい。
In the definition of R 1 to R 14 , the number of carbon atoms is 1 to 3.
As the linear or branched hydrocarbon group of 2, methyl, ethyl, propyl, butyl, pentyl, hexyl, octyl, decyl, dodecyl, tetradecyl, hexadecyl,
Linear alkyl groups such as octadecyl, eicosyl, doeicosyl, tetraeicosyl, hexaeicosyl, octaeicosyl, triacontyl; isopropyl, sec-
Branched chain alkyl groups such as butyl, tert-butyl, neopentyl, 1-ethylpropyl, 1-heptyldecyl and the like can be mentioned. In the present invention, R 1 to R 12 are preferably linear or branched hydrocarbon groups having 1 to 25 carbon atoms (provided that a part of them may be hydrogen atoms), and particularly 1 to 1 carbon atoms.
22 straight or branched chain hydrocarbon groups (provided that some may be hydrogen atoms) are preferred. Further, R 13 and R 14 are preferably a hydrogen atom or a hydrocarbon group having 1 to 5 carbon atoms, and particularly preferably a hydrogen atom.

【0017】更に、p、q及びrはアルキルグリセリル
エーテル基(2)の含有量が1〜50重量%となる数で
あるが、原料となるオルガノポリシロキサンの入手のし
やすさ、製造時の操作性などの点から0〜2000の範
囲とするのが好ましい。また、一般式(3)〜(6)に
おいては、pは特に1〜500の範囲が好ましく、更に
は10〜30の範囲が好ましい。更に、一般式(3)〜
(6)においては、qは特に1〜50の範囲が好まし
く、更には1〜30の範囲が好ましい。
Further, p, q, and r are numbers such that the content of the alkyl glyceryl ether group (2) is 1 to 50% by weight, but the organopolysiloxane as a raw material is easily available, and is easily produced. From the viewpoint of operability and the like, the range of 0 to 2000 is preferable. Further, in the general formulas (3) to (6), p is particularly preferably in the range of 1 to 500, more preferably in the range of 10 to 30. Furthermore, general formula (3)-
In (6), q is particularly preferably in the range of 1 to 50, and more preferably in the range of 1 to 30.

【0018】本発明における(A)成分のアルキルグリ
セリルエーテル変性シリコーンは、良好な仕上り性と化
粧持ちを得るためには、分子中におけるアルキルグリセ
リルエーテル基(2)の含有量が1〜50重量%である
ことが必要であり、この範囲を逸脱すると、上記の効果
が得られなくなり、好ましくない。
The alkyl glyceryl ether-modified silicone as the component (A) in the present invention has a content of the alkyl glyceryl ether group (2) in the molecule of 1 to 50% by weight in order to obtain good finish and cosmetic durability. If it deviates from this range, the above effects cannot be obtained, which is not preferable.

【0019】かかる(A)成分のアルキルグリセリルエ
ーテル変性シリコーンは、特開平4−134013号公
報記載の方法に従って、少なくとも1個のケイ素−水素
結合を有するオルガノハイドロジェンポリシロキサン
に、対応するアルケニルグリセリルエーテルを反応させ
ることにより製造することができる。
The alkyl glyceryl ether-modified silicone as the component (A) is an alkenyl glyceryl ether corresponding to an organohydrogenpolysiloxane having at least one silicon-hydrogen bond according to the method described in JP-A-4-134013. Can be produced by reacting

【0020】本発明における(A)成分のアルキルグリ
セリルエーテル変性シリコーンは、一種又は二種以上を
用いることができ、その配合量は全組成物中に0.1〜
50重量%、特に1〜15重量%の範囲とするのが好ま
しい。配合量が0.1重量%未満であると化粧持ち等の
効果が充分でなく、50重量%を超えると感触が悪化
し、好ましくない。
The alkyl glyceryl ether-modified silicone as the component (A) in the present invention may be used alone or in combination of two or more, and the amount thereof is 0.1 to 10% based on the total composition.
It is preferably in the range of 50% by weight, particularly 1 to 15% by weight. If the blending amount is less than 0.1% by weight, the effect of holding makeup and the like are not sufficient, and if it exceeds 50% by weight, the feel is deteriorated, which is not preferable.

【0021】本発明の油性固型化粧料は、上記必須成分
であるアルキルグリセリルエーテル変性シリコーンを含
み、実質的に水を含まない、非水系化粧料であることが
好ましい。
The oily solid cosmetic composition of the present invention is preferably a non-aqueous cosmetic composition containing the above-mentioned essential component alkyl glyceryl ether-modified silicone and containing substantially no water.

【0022】また、本発明の油性固型化粧料には、上記
(A)成分以外の固体、半固体又は液体の油性原料の一
種又は二種以上(以下、(B)成分という)を配合する
ことができる。かかる油性原料(B)のうち、固体又は
半固体のものとしては、例えばモクロウ、硬化牛脂、カ
ルナウバワックス、キャンデリラワックス、ライスワッ
クス、ミツロウ、セレシンワックス、マイクロクリスタ
リンワックス、パラフィンワックス、ポリエチレンワッ
クス、硬化ホホバ油、ラノリン、ワセリン及びこれらの
混合物等が挙げられる。これらの配合量は、化粧料によ
り適宜決定すればよいが、通常全組成物中に1〜90重
量%、好ましくは5〜70重量%である。
Further, the oily solid cosmetic of the present invention contains one or more solid (semi-solid or liquid) oily raw materials other than the above-mentioned component (A) (hereinafter referred to as the component (B)). be able to. Among the oily raw materials (B), solid or semi-solid ones include, for example, mokuro, hardened beef tallow, carnauba wax, candelilla wax, rice wax, beeswax, ceresin wax, microcrystalline wax, paraffin wax, polyethylene wax, Hardened jojoba oil, lanolin, petrolatum and mixtures thereof and the like can be mentioned. The blending amount of these may be appropriately determined depending on the cosmetic, but is usually 1 to 90% by weight, preferably 5 to 70% by weight in the total composition.

【0023】また、液体の油性原料としては、例えば流
動パラフィン、流動イソパラフィン(流動ポリイソブチ
レン)、スクワラン等の炭化水素類;オリーブ油、ホホ
バ油等の天然動植物油;ジメチルポリシロキサン等のシ
リコーン油;イソプロピルミリステート等の合成エステ
ル油、及びこれらの混合物等が挙げられる。これら液体
の油性原料の配合量は、目的により適宜決定すればよい
が、全組成物中に通常1〜90重量%、好ましくは5〜
70重量%である。
Examples of the liquid oily raw material include hydrocarbons such as liquid paraffin, liquid isoparaffin (liquid polyisobutylene) and squalane; natural animal and vegetable oils such as olive oil and jojoba oil; silicone oil such as dimethylpolysiloxane; isopropyl. Examples thereof include synthetic ester oils such as myristate, and mixtures thereof. The blending amount of these liquid oily raw materials may be appropriately determined depending on the purpose, but is usually 1 to 90% by weight, preferably 5 to 10% by weight in the total composition.
It is 70% by weight.

【0024】更に、本発明の油性固型化粧料には化粧品
に通常用いられる公知の顔料を配合することができる。
具体的には、例えば、タルク、セリサイト、マイカ、カ
オリン、シリカ、ナイロンパウダー、ポリエチレンパウ
ダー及びセルロースパウダー等の体質顔料;カーボンブ
ラック、酸化チタン、酸化鉄、酸化亜鉛、群青、紺青、
酸化クロム、有機タール系色素及びレーキ等の着色剤;
並びに雲母タチン及び酸化鉄コーテッド雲母等の複合顔
料等を配合することができる。また、これらの化粧品顔
料をシリコーン、高級脂肪酸、高級アルコール、脂肪酸
エステル、金属石鹸、アミノ酸又はアルキルフォスフェ
ート等により表面処理したものも用いることができる。
これらの顔料は本発明の油性固型化粧料中に0〜95重
量%、好ましくは5〜70重量%の範囲で用いられる。
Further, the oily solid cosmetic of the present invention may be blended with known pigments usually used in cosmetics.
Specifically, for example, extender pigments such as talc, sericite, mica, kaolin, silica, nylon powder, polyethylene powder and cellulose powder; carbon black, titanium oxide, iron oxide, zinc oxide, ultramarine blue, navy blue,
Colorants such as chromium oxide, organic tar dyes and lakes;
In addition, composite pigments such as mica tatin and iron oxide coated mica can be blended. Further, those cosmetic pigments whose surface is treated with silicone, higher fatty acid, higher alcohol, fatty acid ester, metal soap, amino acid or alkyl phosphate can be used.
These pigments are used in the oily solid cosmetic of the present invention in an amount of 0 to 95% by weight, preferably 5 to 70% by weight.

【0025】本発明の油性固型化粧料には、上記成分の
他、目的に応じて、本発明の効果を損なわない限りにお
いて、上記以外の油性原料、界面活性剤、薬効成分、防
腐剤、抗酸化剤、保湿剤、紫外線吸収剤、香料等を配合
することができる。
In the oily solid cosmetic of the present invention, in addition to the above components, other oily raw materials, surfactants, medicinal components, preservatives, other than the above, depending on the purpose, as long as the effects of the present invention are not impaired, Antioxidants, moisturizers, UV absorbers, fragrances and the like can be added.

【0026】また、本発明の油性固型化粧料は、上記成
分を常法に従って、加熱、混合、攪拌等すれば製造する
ことができ、口紅、ファンデーション、アイシャドウ、
アイライナー等のメイクアップ化粧品とすることができ
る。
The oily solid cosmetic composition of the present invention can be produced by heating, mixing, stirring, etc. the above components according to a conventional method, such as lipstick, foundation, eye shadow,
It can be a makeup cosmetic product such as an eyeliner.

【0027】[0027]

【発明の効果】本発明の油性固型化粧料に配合されるア
ルキルグリセリルエーテル変性シリコーンは、水の無い
状態では液状であるが少量(1〜20重量%)の水が添
加されると粘度が上昇する。よって、本発明の油性固型
化粧料は、調製時では粘度の低い状態にあるため、化粧
料ののびが軽く、皮膚上に顔料を薄く均一に塗布するこ
とができ、仕上り、使用感に優れている。また、塗布後
においては皮膚又は、吐息等から塗布膜中に水分が供給
され、当該塗布膜中のアルキルグリセリルエーテル変性
シリコーンが高粘度化することにより、塗布膜の粘度が
高くなり、化粧落ちしにくくなる。更に水の存在下で
は、アルキルグリセリルエーテル変性シリコーンと皮膚
や唇との密着性も向上し、結果として化粧持ちが向上す
る。従って、本発明の油性固型化粧料は、使用感及び仕
上り性に優れると共に、化粧持ちの良好なものである。
The alkyl glyceryl ether-modified silicone compounded in the oily solid cosmetic composition of the present invention is liquid in the absence of water, but has a viscosity when a small amount (1 to 20% by weight) of water is added. To rise. Therefore, the oily solid cosmetic of the present invention has a low viscosity at the time of preparation, so that the spread of the cosmetic is light and the pigment can be applied thinly and evenly on the skin, resulting in excellent finish and usability. ing. In addition, after application, water is supplied into the coating film from the skin or breath, and the alkylglyceryl ether-modified silicone in the coating film becomes highly viscous, which increases the viscosity of the coating film and removes makeup. It gets harder. Further, in the presence of water, the adhesion between the alkyl glyceryl ether-modified silicone and the skin or the lips is improved, and as a result, the durability of makeup is improved. Therefore, the oily solid cosmetic composition of the present invention is excellent in the feeling of use and finish and has a long lasting makeup.

【0028】[0028]

【実施例】以下、実施例により本発明を更に詳細に説明
するが、本発明は、これらに限定されるものではない。
The present invention will be described in more detail with reference to the following examples, but the present invention is not limited thereto.

【0029】参考例1 冷却管及び磁気攪拌子を備えた100ml 2口フラスコ
に下記式
Reference Example 1 A 100 ml two-necked flask equipped with a cooling tube and a magnetic stirrer was charged with the following formula.

【0030】[0030]

【化4】 [Chemical 4]

【0031】で示されるオルガノハイドロジェンシロキ
サン15g(4.4mmol)、10−ウンデセニルグリセ
リルエーテル8.1g(33mmol)、酢酸カリウムの1
0%エタノール溶液0.65g(0.66mmol)及びイ
ソプロピルアルコール50gを仕込み、これに塩化白金
酸の2%イソプロピルアルコール溶液0.17g(6.
6×10-3mmol)を加え、加熱し昇温した。内容物の温
度を40℃に保ち2.5時間攪拌した。溶媒を留去し活
性炭処理を行ったのち、減圧蒸留により、未反応の10
−ウンデセニルグリセリルエーテルを留去し褐色高粘稠
物を得た。得られた生成物はIR及1H−NMRスペク
トルにより下記の式で示される化合物(1−a)である
ことが確認された。平均分子量5800(1H−NMR
より算出)、アルキルグリセリルエーテル基含有率17
重量%。
Organohydrogensiloxane represented by 15 g (4.4 mmol), 10-undecenyl glyceryl ether 8.1 g (33 mmol), 1 part of potassium acetate
0.65 g (0.66 mmol) of a 0% ethanol solution and 50 g of isopropyl alcohol were charged, and 0.17 g (6.
6 × 10 −3 mmol) was added and the temperature was raised by heating. The temperature of the contents was kept at 40 ° C. and stirred for 2.5 hours. After distilling off the solvent and treating with activated carbon, the unreacted 10
-Undecenyl glyceryl ether was distilled off to obtain a brown highly viscous material. The obtained product was confirmed to be compound (1-a) represented by the following formula by IR and 1 H-NMR spectrum. Average molecular weight 5800 ( 1 H-NMR
Calculated), the content of alkyl glyceryl ether group is 17
weight%.

【0032】[0032]

【化5】 [Chemical 5]

【0033】IR(液膜,cm-1) 3420(−OH) 2968, 2932, 2860(C−H) 1264(Si−CH3) 1096, 1026, 842(Si−O−Si)1 H−NMR〔δppm, CDCl3 中、CHCl3 基準(7.28pp
m)〕 0.00 (s,約390H) Si-CH 3 0.35-0.50 (m,8H) Si-CH 2 1.08-1.39 (br,64H) -CH 2- 1.39-1.62 (br,8H) CH 2-CH2-O 1.96-2.29 (br,4H) CH2-OH 2.43-2.68 (br,4H) CH-OH 3.38-3.50 (m,16H) CH 2-O 3.50-3.70 (m,8H) CH 2-OH 3.70-3.86 (m,4H) CH-OH
IR (liquid film, cm -1 ) 3420 (-OH) 2968, 2932, 2860 (C-H) 1264 (Si-CH 3 ) 1096, 1026, 842 (Si-O-Si) 1 H-NMR (Δppm, in CDCl 3 , CHCl 3 standard (7.28pp
m)] 0.00 (s, about 390H) Si-C H 3 0.35-0.50 (m, 8H) Si-C H 2 1.08-1.39 (br, 64H) -C H 2 - 1.39-1.62 (br, 8H) C H 2 -CH 2 -O 1.96-2.29 (br, 4H) CH 2 -O H 2.43-2.68 (br, 4H) CH-O H 3.38-3.50 (m, 16H) C H 2 -O 3.50-3.70 (m , 8H) C H 2 -OH 3.70-3.86 (m, 4H) C H -OH

【0034】参考例2 冷却管及び磁気攪拌子を備えた100ml 2口フラスコ
に下記式
Reference Example 2 A 100 ml two-necked flask equipped with a cooling tube and a magnetic stirrer was charged with the following formula.

【0035】[0035]

【化6】 [Chemical 6]

【0036】で示されるオルガノハイドロジェンシロキ
サン15g(4.4mmol)、アリルグリセリルエーテル
4.3g(33mmol)、酢酸カリウムの10%エタノー
ル溶液0.65g(0.66mmol)及びイソプロピルア
ルコール50gを仕込み、これに塩化白金酸の2%イソ
プロピルアルコール溶液0.17g(6.6×10-3mm
ol)を加え、加熱し昇温した。内容物の温度を40℃に
保ち、2.5時間攪拌した。溶媒を留去し、活性炭処理
を行った後、減圧蒸留により、未反応のアリルグリセリ
ルエーテルを減圧留去し、粘稠物を得た。得られた生成
物はIR及び1H−NMRスペクトルにより下式(1−
b)で示される化合物であることが確認された。平均分
子量4000(1H−NMRにより算出)、アルキルグ
リセリルエーテル含有率20重量%。
15 g (4.4 mmol) of an organohydrogensiloxane represented by, 4.3 g (33 mmol) of allyl glyceryl ether, 0.65 g (0.66 mmol) of a 10% potassium acetate solution in ethanol and 50 g of isopropyl alcohol were charged. 2% isopropyl alcohol solution of chloroplatinic acid 0.17g (6.6 × 10 -3 mm
ol) was added and heated to raise the temperature. The temperature of the contents was kept at 40 ° C, and the mixture was stirred for 2.5 hours. After distilling off the solvent and treating with activated carbon, the unreacted allyl glyceryl ether was distilled off under reduced pressure by distillation under reduced pressure to obtain a viscous material. The obtained product was analyzed by IR and 1 H-NMR spectrum to obtain the following formula (1-
It was confirmed to be the compound represented by b). Average molecular weight 4000 (calculated by 1 H-NMR), alkyl glyceryl ether content 20% by weight.

【0037】[0037]

【化7】 [Chemical 7]

【0038】IR(液膜,cm-1) 3400(−OH) 2965, 2925, 2860(C−H) 1262(Si−CH3) 1096, 1022, 844(Si−O−Si)1 H−NMR〔δppm, CDCl3 中、CHCl3 基準(7.28pp
m)〕 0.01 (s,約273H) Si-CH 3 0.38-0.58 (m,10H) Si-CH 2- 1.10-1.41 (br,8H) -CH 2- 1.44-1.86 (m,10H) CH 2-CH2-O 3.30-3.55 (m,20H) CH 2-O 3.55-3.77 (m,10H) CH 2-OH 3.77-3.90 (m,5H) CH-OH
IR (liquid film, cm -1 ) 3400 (-OH) 2965, 2925, 2860 (C-H) 1262 (Si-CH 3 ) 1096, 1022, 844 (Si-O-Si) 1 H-NMR (Δppm, in CDCl 3 , CHCl 3 standard (7.28pp
m)] 0.01 (s, about 273H) Si-C H 3 0.38-0.58 (m, 10H) Si-C H 2 - 1.10-1.41 (br, 8H) -C H 2 - 1.44-1.86 (m, 10H) C H 2 -CH 2 -O 3.30-3.55 (m, 20H) C H 2 -O 3.55-3.77 (m, 10H) C H 2 -OH 3.77-3.90 (m, 5H) C H -OH

【0039】実施例1 口紅 下記表1に示す各成分を80℃に加熱して均一に混合
し、成型用型に流し込み、冷却固化し、口紅を製造し
た。得られた口紅についてパネラー10名により、表1
の試験項目について、次の評価基準により官能評価を行
った。この結果を表1に示す。
Example 1 Lipstick Lipsticks were produced by heating the components shown in Table 1 below to 80 ° C. and mixing them uniformly, pouring them into a molding die and cooling and solidifying. About the obtained lipstick, Table 1 was prepared by 10 panelists.
Sensory evaluation was performed on the test items according to the following evaluation criteria. The results are shown in Table 1.

【0040】評価基準 ◎:10名中8名以上が良好と評価した。 ○:10名中6名以上が良好と評価した。 △:10名中4名以上が良好と評価した。 ×:10名中3名以下が良好と評価した。Evaluation Criteria ⊚: Eight or more out of 10 evaluated as good. ◯: 6 or more out of 10 evaluated as good. Δ: 4 or more out of 10 evaluated as good. X: 3 out of 10 evaluated as good.

【0041】[0041]

【表1】 [Table 1]

【0042】表1から明らかなように、本発明の口紅
は、仕上り、色移りと色落ちのしにくさ、更に、にじみ
にくさに優れたものであった。
As is clear from Table 1, the lipstick of the present invention was excellent in finish, color transfer and color fading resistance, and further bleeding resistance.

【0043】実施例2 実施例1の本発明品1のアルキルグリセリルエーテル変
性シリコーンの代わりに参考例2で得られたアルキルグ
リセリルエーテル変性シリコーンを用い、実施例1と同
様にして口紅を製造した。この本発明の口紅(本発明品
2)は、仕上り、色移りと色落ちのしにくさ、更に、に
じみにくさに優れたものであった。
Example 2 A lipstick was produced in the same manner as in Example 1, except that the alkyl glyceryl ether-modified silicone obtained in Reference Example 2 was used in place of the alkyl glyceryl ether-modified silicone of Inventive Product 1 of Example 1. The lipstick of the present invention (Product 2 of the present invention) was excellent in finish, color transfer and color fading resistance, and further bleeding resistance.

【0044】実施例3 油性ファンデーション 表2に示す成分中、ワックス及びオイル成分を90℃に
て溶解し、これに顔料部及び香料を加え混合、脱気し
た。これを金型に流し込み、冷却成型後、容器に充填
し、油性ファンデーションを得た。これらのファンデー
ションの化粧持ちについて、実施例1の評価基準に従い
評価した。結果を表2に示す。
Example 3 Oily foundation Of the components shown in Table 2, the wax and oil components were dissolved at 90 ° C., the pigment part and the fragrance were added thereto, and the mixture was degassed. This was poured into a mold, cooled and molded, and then filled in a container to obtain an oily foundation. The makeup retention of these foundations was evaluated according to the evaluation criteria of Example 1. The results are shown in Table 2.

【0045】[0045]

【表2】 [Table 2]

【0046】表2から明らかなように、本発明の油性フ
ァンデーションは、化粧持ち(化粧くずれ防止)におい
て、比較品よりも明らかに優れていた。
As is clear from Table 2, the oil-based foundation of the present invention was clearly superior to the comparative product in terms of makeup retention (prevention of makeup deterioration).

【0047】実施例4 固型パウダーアイシャドウ 表3に示す成分中、粉末部をブレンダーで攪拌混合し、
これに加熱溶解した油相部を吹きつけ、更に攪拌した。
その後、粉砕して成型機で圧縮成型し、固型パウダーア
イシャドウを得た。これらのパウダーアイシャドウの化
粧持ちについて実施例1の評価基準に従い評価した。結
果を表3に示す。
Example 4 Solid Powder Eye Shadow Among the components shown in Table 3, the powder part was stirred and mixed with a blender,
The oil phase part which was heated and dissolved was sprayed onto this and further stirred.
Then, it was crushed and compression molded with a molding machine to obtain a solid powder eye shadow. The makeup retention of these powder eye shadows was evaluated according to the evaluation criteria of Example 1. The results are shown in Table 3.

【0048】[0048]

【表3】 [Table 3]

─────────────────────────────────────────────────────
─────────────────────────────────────────────────── ───

【手続補正書】[Procedure amendment]

【提出日】平成5年5月14日[Submission date] May 14, 1993

【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】0024[Name of item to be corrected] 0024

【補正方法】変更[Correction method] Change

【補正内容】[Correction content]

【0024】更に、本発明の油性固型化粧料には化粧品
に通常用いられる公知の顔料を配合することができる。
具体的には、例えば、タルク、セリサイト、マイカ、カ
オリン、シリカ、ナイロンパウダー、ポリエチレンパウ
ダー及びセルロースパウダー等の体質顔料;カーボンブ
ラック、酸化チタン、酸化鉄、酸化亜鉛、群青、紺青、
酸化クロム、有機タール系色素及びレーキ等の着色剤;
並びに雲母チタン及び酸化鉄コーテッド雲母等の複合顔
料等を配合することができる。また、これらの化粧品顔
料をシリコーン、高級脂肪酸、高級アルコール、脂肪酸
エステル、金属石鹸、アミノ酸又はアルキルフォスフェ
ート等により表面処理したものも用いることができる。
これらの顔料は本発明の油性固型化粧料中に0〜95重
量%、好ましくは5〜70重量%の範囲で用いられる。
Further, the oily solid cosmetic of the present invention may be blended with known pigments usually used in cosmetics.
Specifically, for example, extender pigments such as talc, sericite, mica, kaolin, silica, nylon powder, polyethylene powder and cellulose powder; carbon black, titanium oxide, iron oxide, zinc oxide, ultramarine blue, navy blue,
Colorants such as chromium oxide, organic tar dyes and lakes;
In addition, composite pigments such as mica titanium and iron oxide coated mica may be blended. Further, those cosmetic pigments whose surface is treated with silicone, higher fatty acid, higher alcohol, fatty acid ester, metal soap, amino acid or alkyl phosphate can be used.
These pigments are used in the oily solid cosmetic of the present invention in an amount of 0 to 95% by weight, preferably 5 to 70% by weight.

Claims (3)

【特許請求の範囲】[Claims] 【請求項1】 アルキルグリセリルエーテル変性シリコ
ーンの一種又は二種以上を含有する油性固型化粧料。
1. An oily solid cosmetic containing one or more alkyl glyceryl ether-modified silicones.
【請求項2】 アルキルグリセリルエーテル変性シリコ
ーンが下記一般式(1)で表わされるものである請求項
1記載の油性固型化粧料。 【化1】 (式中、Qは炭素数3〜20の二価の炭化水素基を示
し、R13及びR14は同一又は異なって水素原子又は炭素
数1〜32の直鎖又は分岐鎖の炭化水素基を示す)で表
わされるアルキルグリセリルエーテル基を示し、残り
は、それぞれ水素原子、炭素数1〜32の直鎖又は分岐
鎖の炭化水素基又はフェニル基を示し、p、q及びrは
分子中における一般式(2)で表わされるアルキルグリ
セリルエーテル基の含有量が1〜50重量%となる数を
示す〕
2. The oily solid cosmetic composition according to claim 1, wherein the alkyl glyceryl ether-modified silicone is represented by the following general formula (1). [Chemical 1] (In the formula, Q represents a divalent hydrocarbon group having 3 to 20 carbon atoms, and R 13 and R 14 are the same or different and each represents a hydrogen atom or a linear or branched hydrocarbon group having 1 to 32 carbon atoms. Represents the alkyl glyceryl ether group, and the rest each represent a hydrogen atom, a linear or branched hydrocarbon group having 1 to 32 carbon atoms or a phenyl group, and p, q and r are general in the molecule. The content of the alkyl glyceryl ether group represented by the formula (2) is 1 to 50% by weight.]
【請求項3】 更に、アルキルグリセリルエーテル変性
シリコーン以外の固体、半固体又は液体の油性原料を含
有する請求項1又は2記載の油性固型化粧料。
3. The oily solid cosmetic composition according to claim 1, further comprising a solid, semi-solid or liquid oily raw material other than the alkyl glyceryl ether modified silicone.
JP09405093A 1993-04-21 1993-04-21 Oily solid cosmetics Expired - Lifetime JP3477222B2 (en)

Priority Applications (1)

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Application Number Priority Date Filing Date Title
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ID=14099733

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Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0971504A (en) * 1995-09-08 1997-03-18 Kose Corp Oily cosmetic
JPH11349430A (en) * 1998-06-09 1999-12-21 Kao Corp Oily solid cosmetic
JP2005194523A (en) * 2003-12-10 2005-07-21 Kao Corp Modified polysiloxane and cosmetic material using the same
EP1616557A2 (en) 2004-07-16 2006-01-18 L'oreal Cosmetic composition containing a selected silicone polymer and a film-forming agent
EP1621230A1 (en) 2004-07-16 2006-02-01 L'oreal Cosmetic composition comprising a defined polymeric silicone and a gelling agent
EP1623700A1 (en) 2004-07-16 2006-02-08 L'oreal Cosmetic composition showing an improved hold
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
WO2011049247A1 (en) 2009-10-23 2011-04-28 東レ・ダウコーニング株式会社 Thickening or gelling agent for oily raw materials
JP2011173818A (en) * 2010-02-24 2011-09-08 Kao Corp Oily cosmetic
EP2551291A1 (en) 2011-07-28 2013-01-30 Daicel Corporation Dihydroxypropylamide-modified polysiloxane compound
US8597619B2 (en) 2009-12-21 2013-12-03 Dow Corning Toray., Ltd. Thickener or gellant for oil materials, gel composition comprising same, and method of producing cosmetic material or topical agent
JP2014024760A (en) * 2012-07-24 2014-02-06 Kao Corp Oily cosmetic
JP2014088354A (en) * 2012-10-31 2014-05-15 Kao Corp Lip cosmetic
JP2015013816A (en) * 2013-07-03 2015-01-22 花王株式会社 Lip cosmetic
US9133309B2 (en) 2009-10-23 2015-09-15 Dow Corning Toray Co., Ltd. Organopolysiloxane copolymer
JP2017025030A (en) * 2015-07-23 2017-02-02 株式会社ダイセル Composition for makeup cosmetics
JP2017025031A (en) * 2015-07-23 2017-02-02 株式会社ダイセル Emulsion cosmetic composition
US10406092B2 (en) 2012-12-28 2019-09-10 Dow Silicones Corporation Method for producing transparent or semi-transparent liquid glycerin-derivative-modified silicone composition

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0971504A (en) * 1995-09-08 1997-03-18 Kose Corp Oily cosmetic
JPH11349430A (en) * 1998-06-09 1999-12-21 Kao Corp Oily solid cosmetic
JP4584697B2 (en) * 2003-12-10 2010-11-24 花王株式会社 Modified polysiloxane and cosmetics using the modified polysiloxane
JP2005194523A (en) * 2003-12-10 2005-07-21 Kao Corp Modified polysiloxane and cosmetic material using the same
EP1616557A2 (en) 2004-07-16 2006-01-18 L'oreal Cosmetic composition containing a selected silicone polymer and a film-forming agent
EP1623700A1 (en) 2004-07-16 2006-02-08 L'oreal Cosmetic composition showing an improved hold
EP1621230A1 (en) 2004-07-16 2006-02-01 L'oreal Cosmetic composition comprising a defined polymeric silicone and a gelling agent
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
WO2011049247A1 (en) 2009-10-23 2011-04-28 東レ・ダウコーニング株式会社 Thickening or gelling agent for oily raw materials
US8784787B2 (en) 2009-10-23 2014-07-22 Dow Corning Toray Co., Ltd. Co-modified organopolysiloxane
US9580600B2 (en) 2009-10-23 2017-02-28 Dow Conring Toray Co., Ltd. Thickening or gelling agent for oily raw materials
US9133309B2 (en) 2009-10-23 2015-09-15 Dow Corning Toray Co., Ltd. Organopolysiloxane copolymer
US8597619B2 (en) 2009-12-21 2013-12-03 Dow Corning Toray., Ltd. Thickener or gellant for oil materials, gel composition comprising same, and method of producing cosmetic material or topical agent
JP2011173818A (en) * 2010-02-24 2011-09-08 Kao Corp Oily cosmetic
EP2551291A1 (en) 2011-07-28 2013-01-30 Daicel Corporation Dihydroxypropylamide-modified polysiloxane compound
US9012672B2 (en) 2011-07-28 2015-04-21 Daicel Corporation Dihydroxypropylamide-modified polysiloxane compound
JP2014024760A (en) * 2012-07-24 2014-02-06 Kao Corp Oily cosmetic
JP2014088354A (en) * 2012-10-31 2014-05-15 Kao Corp Lip cosmetic
US10406092B2 (en) 2012-12-28 2019-09-10 Dow Silicones Corporation Method for producing transparent or semi-transparent liquid glycerin-derivative-modified silicone composition
JP2015013816A (en) * 2013-07-03 2015-01-22 花王株式会社 Lip cosmetic
JP2017025030A (en) * 2015-07-23 2017-02-02 株式会社ダイセル Composition for makeup cosmetics
JP2017025031A (en) * 2015-07-23 2017-02-02 株式会社ダイセル Emulsion cosmetic composition

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