JPH0468015B2 - - Google Patents

Info

Publication number
JPH0468015B2
JPH0468015B2 JP60051949A JP5194985A JPH0468015B2 JP H0468015 B2 JPH0468015 B2 JP H0468015B2 JP 60051949 A JP60051949 A JP 60051949A JP 5194985 A JP5194985 A JP 5194985A JP H0468015 B2 JPH0468015 B2 JP H0468015B2
Authority
JP
Japan
Prior art keywords
polyoxyalkylene
modified
emulsifier composition
silicone oil
clay mineral
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.)
Expired - Lifetime
Application number
JP60051949A
Other languages
Japanese (ja)
Other versions
JPS61212321A (en
Inventor
Masaaki Ishiwatari
Yutaka Okunuki
Tomyuki Nanba
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.)
Shiseido Co Ltd
Original Assignee
Shiseido Co Ltd
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 Shiseido Co Ltd filed Critical Shiseido Co Ltd
Priority to JP60051949A priority Critical patent/JPS61212321A/en
Publication of JPS61212321A publication Critical patent/JPS61212321A/en
Publication of JPH0468015B2 publication Critical patent/JPH0468015B2/ja
Granted legal-status Critical Current

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89Polysiloxanes
    • A61K8/891Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • A61K8/894Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone modified by a polyoxyalkylene group, e.g. cetyl dimethicone copolyol
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/02Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04Dispersions; Emulsions
    • A61K8/06Emulsions
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/02Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04Dispersions; Emulsions
    • A61K8/06Emulsions
    • A61K8/064Water-in-oil emulsions, e.g. Water-in-silicone emulsions
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/26Aluminium; Compounds thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin

Description

【発明の詳細な説明】[Detailed description of the invention]

[産業上の利用分野] 本発明は乳化剤組成物に関する。さらに詳しく
は、種々の油、とくにシリコン油を安定性、使用
性良好に油中水型(以下、W/Oという)に乳化
しうる乳化剤組成物に関する。 [従来の技術] 従来、W/O乳化系はさまざまな製品に使用さ
れている。とくに、シリコン油はなめらかな使用
性をもち揆水性に優れていることから化粧料分野
では重要な油である。とりわけ、シリコン油の中
でも揮散性シリコン油を使用すると当初のびがよ
くかつ塗布にともなつて揮散性シリコン油が揮散
してしまうので塗布後の化粧くずれが少ないこと
からメーキヤツプ化粧料には多用されている。そ
の他、のびのよい使用感を求められるフエーシヤ
ル化粧料、水はじきの性能を要求されるハンドク
リームや頭髪化粧料などにも好まれて利用されて
きた。また、シリコン油は皮膚安全性が高いとい
う、とくに化粧料原料として要求される条件も備
えている。 [発明が解決しようとする問題点] しかしながら、シリコン油は安定なW/O乳化
系を得るのが非常にむづかしいという欠点を有し
ており、強く要望されているにもかかわらず、こ
のものを多量に配合しかつ市販に耐え得る安定性
を有するW/O乳化物は得られていない。 これまで、安定性良好なシリコン油のW/O乳
化物を得るためにはシリコンオイルをワツクス類
とともに固化する方法や、シリカあるいは親油化
処理したシリカを併用するなどの方法がとられて
きた。しかしながら、ワツクス類とともに固化す
る方法はのびが重くべたつくといつた使用性上の
欠点や、流動性がないため応用できる範囲が限ら
れている。また、シリカを併用する方法は経時で
の安定性が悪く、使用前によく振ることが必須で
あり好ましくない。 [問題点を解決するための手段] 本発明者らは、こうした事情にかんがみ、シリ
コン油のW/O乳化法について鋭意研究を重ねた
結果、特定のシリコン化合物でもつて有機変性モ
ンモリロナイトを処理した乳化剤組成物が種々の
油、とくにシリコン油に対して良好な乳化性を有
することを見いだし、この知見に基づいて本発明
を完成するに至つた。 すなわち、本発明は、有機変性粘土鉱物を一般
式()、()または()で示されるポリオキ
シアルキレン変性オルガノポリシロキサンの一種
または二種以上で処理して得られる乳化剤組成物
である。 {一般式()、()、()中、Rはメチル基ま
たは一部がフエニル基、R′は水素または炭素数
1〜12のアルキル基、pは1〜5の数、qは2〜
3の数、x、m、nは平均数でポリオキシアルキ
レン変性オルガノポリシロキサンが分子中にポリ
オキシアルキレン基を20〜40重量%(20重量%含
まず)含有し且つ該ポリオキシアルキレン変性オ
ルガノポリシロキサンの粘度が25℃において5〜
3000センチストークスになるような数値を表す。} 以下、本発明の構成について詳述する。 本発明で用いられるポリオキシアルキレン変性
オルガノポリシロキサン(以下、ポリエーテル変
性シリコンと略記する)は前期一般式()、
()または()で表されるものであり、これ
らのうちの任意の一種又は二種以上が選ばれて用
いられる。 とくにシリコン油を安定性、使用性良好にW/
O乳化するためには、ポリエーテル変性シリコン
はポリオキシアルキレン基をその分子量に対して
20〜40重量%(20重量%含まず)の割合で含有し
且つ25℃においてそのもの自体の粘度が5〜3000
センチストークスの範囲に存するとよい。ポリエ
ーテル変性シリコンの粘度が5センチストークス
未満では乳化安定性が劣化する傾向にあり、3000
センチストークスを越えると使用感がべたつき好
ましくない。 本発明で用いられる有機変性粘土鉱物は粘土鉱
物の結晶層間に介在する水や交換性カチオンを有
機極性化合物や有機カチオンで置換したものであ
り、たとえば、ジオクタデシルジメチルアンモニ
ウム塩変性モンモリロナイト、オクタデシルジメ
チルベンジルアンモニウム塩変性モンモリロナイ
ト、ジヘキサデシルジメチルアンモニウム塩変性
モンモリロナイトなどが挙げられる。これらの中
から一種または二種以上が任意に選択される。 乳化剤組成物中のポリオキシアルキレン変性オ
ルガノポリシロキサンの有機変性粘土鉱物に対す
る含有量は有機変性粘土鉱物100gに対し5〜600
g、好ましくは10〜500gである。 本範囲の乳化剤組成物を得るには有機変性粘土
鉱物をポリオキシアルキレン変性オルガノポリシ
ロキサンで処理すればよい。 処理方法としては、たとえば、次の方法を例示
できる。すなわち、水、アセトン、低級アルコー
ル、揮発性イソパラフインあるいは揮発性シリコ
ン油などの溶剤中で有機変性粘土鉱物をポリオキ
シアルキレン変性オルガノポリシロキサンととも
に分散撹拌する。ついで、溶剤を除去することに
よつてポリオキシアルキレン変性オルガノポリシ
ロキサン層間に吸着され表面改善された有機変性
粘土鉱物が得られる。 本発明の乳化剤組成物を用いて油をW/O型に
乳化するには公知の乳化技術を用いればよい。す
なわち、一例を挙げれば、本発明の乳化剤組成物
をシリコン油中に分散してシリコン油を含む油性
ゲルを製造し、その中へ水を添加すればよい。 シリコン油としては従来用いられている周知の
もの全てが良好に乳化し得る。具体例を挙げれば
ジメチルポリシロキサン、メチルフエニルポリシ
ロキサン、オクタメチルシクロテトラシロキサ
ン、デカメチルシクロペンタシロキサンなどが例
示される。乳化量は任意であるが、通常、乳化物
全量中の20〜90重量%が好適である。 本発明の乳化剤組成物には上記の必須構成成分
に加えて、必要に応じて香料、防腐剤、酸化防止
剤、他の界面活性剤等を適宜配合し得る。 [発明の効果] 本発明の乳化剤組成物は油、とくにシリコン油
を良好にW/Oに乳化することが可能で、得られ
るW/O乳化物は経時安定性に優れ、かつ使用に
際してはのびがよくてべたつきがない良好な使用
感触を有し、耐水性や経時の持ちにも優れたW/
O乳化物になる。当然のことながら、該W/O乳
化物を前記の方法で製造する場合には、その過程
で得られる(水を添加する前段階の)シリコン油
ゲルも安定性良好なので、そのまま油性ゲルとし
て利用可能である。また粘度すなわち流動性も自
由にコントロールできるため、化粧料をはじめ、
医薬品の基剤や自動車ワツクス、家具ワツクスな
ど広い範囲にわたつて使用することができる。 [実施例] 次に実施例によつて本発明をさらに詳細に説明
する。本発明はこれにより限定されるものではな
い。配合量は重量%である。 なお、実施例および比較例の諸特性についての
試験法は次の通り行つたものである。 (1) 安定性 サンプル管に試料を取り各温度条件に放置
し、分離度で評価(1週間後判定)。 評価基準 ○:分離なし △:1/5程度分離 ×:2/3以上分離 (2) 粘度 ブルツクフイールド型粘度計にて測定(30
℃、1日後)。 (3) べたつきおよびのび 実使用試験による官能評価(パネル20名)。 評価基準 ○:べたつきなし、のびが軽い。 △:ややべたつく、のびが普通。 ×:べたつく、のびが重い。 実施例 1 ポリエーテル変性ジメチルポリシロキサン{一
般式()のタイプ、ポリオキシエチレン含有率
25%、粘度260CS/25℃}10gを溶解したエタノ
ール溶液50mlにジオクタデシルジメチルアンモニ
ウム塩変性モンモリロナイト10gを添加し、1時
間デイスパーにて撹拌する。ついで、エバポレー
ターでエタノールを除去した後、50℃で一昼夜乾
燥して目的の乳化剤組成物を得た。 得られた乳化剤組成物は油、とくにシリコン油
に対して優れた乳化性を示した。
[Industrial Field of Application] The present invention relates to an emulsifier composition. More specifically, the present invention relates to an emulsifier composition capable of emulsifying various oils, particularly silicone oil, into water-in-oil (hereinafter referred to as W/O) with good stability and usability. [Prior Art] Conventionally, W/O emulsification systems have been used in various products. In particular, silicone oil is an important oil in the cosmetics field because it is smooth to use and has excellent water repellent properties. In particular, among silicone oils, volatile silicone oils are often used in make-up cosmetics because they spread easily at the beginning and the volatile silicone oil evaporates as they are applied, resulting in less makeup smearing after application. There is. In addition, it has been used favorably in facial cosmetics that require a long-lasting feel, as well as hand creams and hair cosmetics that require water-repellent properties. In addition, silicone oil has a high level of skin safety, which is particularly required as a raw material for cosmetics. [Problems to be Solved by the Invention] However, silicone oil has the disadvantage that it is very difficult to obtain a stable W/O emulsion system, and despite strong demand, it is difficult to obtain a stable W/O emulsion system. A W/O emulsion that can be blended in a large amount and has enough stability to be commercially available has not been obtained. Up until now, methods have been used to obtain a W/O emulsion of silicone oil with good stability, such as solidifying silicone oil with waxes, or using silica or silica treated to make it lipophilic. . However, the method of solidifying with waxes has disadvantages in usability, such as being difficult to spread and is sticky, and has no fluidity, which limits its applicability. Further, the method of using silica in combination is not preferred because it has poor stability over time and requires shaking well before use. [Means for Solving the Problems] In view of these circumstances, the present inventors have conducted extensive research on the W/O emulsification method of silicone oil, and have developed an emulsifier in which organically modified montmorillonite is treated with a specific silicone compound. It was discovered that the composition has good emulsifying properties with respect to various oils, especially silicone oil, and based on this finding, the present invention was completed. That is, the present invention is an emulsifier composition obtained by treating an organically modified clay mineral with one or more polyoxyalkylene-modified organopolysiloxanes represented by the general formula (), (), or (). {In the general formulas (), (), (), R is a methyl group or partially a phenyl group, R' is hydrogen or an alkyl group having 1 to 12 carbon atoms, p is a number from 1 to 5, and q is a number from 2 to
The numbers 3, x, m, and n are average numbers, and the polyoxyalkylene-modified organopolysiloxane contains 20 to 40% by weight (excluding 20% by weight) of polyoxyalkylene groups in the molecule, and The viscosity of polysiloxane is 5~5 at 25℃
Represents a number that equals 3000 centistokes. } Hereinafter, the configuration of the present invention will be explained in detail. The polyoxyalkylene-modified organopolysiloxane (hereinafter abbreviated as polyether-modified silicone) used in the present invention has the general formula (),
It is represented by () or (), and one or more of these may be selected and used. In particular, silicone oil has good stability and usability.
In order to emulsify the polyether-modified silicone, polyoxyalkylene groups must be added to its molecular weight.
Contains 20 to 40% by weight (excluding 20% by weight) and has a viscosity of 5 to 3000 at 25°C
Preferably within the centistoke range. If the viscosity of polyether-modified silicone is less than 5 centistokes, emulsion stability tends to deteriorate;
If it exceeds centistokes, the feeling of use becomes sticky and undesirable. The organically modified clay mineral used in the present invention is a clay mineral in which the water and exchangeable cations present between the crystal layers are replaced with organic polar compounds or organic cations, such as dioctadecyldimethylammonium salt-modified montmorillonite, octadecyldimethylbenzyl Examples include ammonium salt-modified montmorillonite and dihexadecyldimethylammonium salt-modified montmorillonite. One or more types are arbitrarily selected from these. The content of polyoxyalkylene-modified organopolysiloxane in the emulsifier composition is 5 to 600% per 100g of organically modified clay mineral.
g, preferably 10 to 500 g. In order to obtain an emulsifier composition within this range, an organically modified clay mineral may be treated with a polyoxyalkylene modified organopolysiloxane. Examples of the processing method include the following method. That is, an organically modified clay mineral is dispersed and stirred together with a polyoxyalkylene modified organopolysiloxane in a solvent such as water, acetone, lower alcohol, volatile isoparaffin, or volatile silicone oil. Then, by removing the solvent, an organically modified clay mineral adsorbed between the polyoxyalkylene modified organopolysiloxane layers and whose surface has been improved is obtained. In order to emulsify oil into a W/O type using the emulsifier composition of the present invention, a known emulsification technique may be used. That is, to give one example, the emulsifier composition of the present invention may be dispersed in silicone oil to produce an oily gel containing silicone oil, and water may be added therein. All conventionally used and well-known silicone oils can emulsify well. Specific examples include dimethylpolysiloxane, methylphenylpolysiloxane, octamethylcyclotetrasiloxane, and decamethylcyclopentasiloxane. The amount of emulsification is arbitrary, but usually 20 to 90% by weight based on the total amount of emulsion is suitable. In addition to the above-mentioned essential components, the emulsifier composition of the present invention may contain fragrances, preservatives, antioxidants, other surfactants, etc., as necessary. [Effects of the Invention] The emulsifier composition of the present invention can emulsify oil, especially silicone oil, into W/O well, and the resulting W/O emulsion has excellent stability over time and is easy to spread when used. W/ has a good texture and no stickiness, and has excellent water resistance and durability over time.
It becomes an O emulsion. Naturally, when the W/O emulsion is produced by the above method, the silicone oil gel obtained in the process (before adding water) also has good stability, so it can be used as is as an oil gel. It is possible. In addition, the viscosity, or fluidity, can be controlled freely, so it can be used in cosmetics and other applications.
It can be used in a wide range of applications, including pharmaceutical bases, automobile waxes, and furniture waxes. [Example] Next, the present invention will be explained in more detail with reference to Examples. The present invention is not limited thereby. The blending amount is in weight%. The test methods for various properties of Examples and Comparative Examples were as follows. (1) Stability A sample is taken in a sample tube and left at each temperature condition, and evaluated by degree of separation (determined after 1 week). Evaluation criteria ○: No separation △: Approximately 1/5 separation ×: 2/3 or more separation (2) Viscosity Measured with a Bruckfield viscometer (30
°C, after 1 day). (3) Stickiness and spread Sensory evaluation based on actual use test (20 panelists). Evaluation criteria: ○: No stickiness, easy spreading. △: Slightly sticky, spreads normally. ×: Sticky, hard to spread. Example 1 Polyether-modified dimethylpolysiloxane {type of general formula (), polyoxyethylene content
Add 10 g of dioctadecyldimethylammonium salt-modified montmorillonite to 50 ml of an ethanol solution containing 10 g of 25%, viscosity 260 CS/25°C}, and stir with a disper for 1 hour. Then, after removing ethanol with an evaporator, the mixture was dried at 50° C. for a day and night to obtain the desired emulsifier composition. The obtained emulsifier composition showed excellent emulsifying properties against oil, especially silicone oil.

【表】 (製法) およびを用いて実施例1に準じて乳化剤組
成物を得る。得られた乳化剤組成物と〜をホ
モデイスパーにて撹拌し、W/O型日やけ用乳液
を得た。表中に示した特性から、実施例2、3お
よび4は経時安定性及び使用性に優れていること
が判る。
[Table] (Production method) An emulsifier composition was obtained according to Example 1 using and. The obtained emulsifier composition and ~ were stirred in a homodisper to obtain a W/O type sunscreen emulsion. From the properties shown in the table, it can be seen that Examples 2, 3 and 4 are excellent in stability over time and usability.

【表】【table】

【表】 (製法) 実施例2、3、4に準じてクリームを得た。 表中に示した特性から実施例5、6、7は経時
安定性および使用性に優れていることが判る。
[Table] (Manufacturing method) A cream was obtained according to Examples 2, 3, and 4. From the characteristics shown in the table, it can be seen that Examples 5, 6, and 7 are excellent in stability over time and usability.

【表】 (製法) 実施例2、3、4に準じて耐水性フアンデーシ
ヨンを得た。 表中に示した特性から実施例8は経時安定性お
よび使用性に優れていることが判る。 また、海浜における実使用テスト(パネル20
名)により耐水性フアンデーシヨンとして十分な
機能を有しており、化粧もちも良いことが確認さ
れた。
[Table] (Manufacturing method) Water-resistant foundations were obtained according to Examples 2, 3, and 4. From the characteristics shown in the table, it can be seen that Example 8 is excellent in stability over time and usability. In addition, actual use tests on the beach (Panel 20
It was confirmed that it has sufficient functionality as a water-resistant foundation and has good makeup retention.

【表】 (製法) 実施例2、3、4に準じて耐水性アイライナー
を得た。 表中に示した特性から実施例9は経時安定性お
よび使用性に優れていることが判る。 また、海浜における実使用テスト(パネル20
名)により耐水性アイライナーとして十分な機能
を有しており、化粧もちも良いことが確認され
た。
[Table] (Manufacturing method) Water-resistant eyeliners were obtained according to Examples 2, 3, and 4. From the characteristics shown in the table, it can be seen that Example 9 is excellent in stability over time and usability. In addition, actual use tests on the beach (Panel 20
It was confirmed that it has sufficient functionality as a water-resistant eyeliner and has good makeup retention.

【表】【table】

【表】 (製法) 実施例2、3、4に準じてつや出しクリームを
得た。 実施例10は化粧品だけでなく、家具のつや出し
クリームなどにも使用できることを実使用テスト
にて確認した。
[Table] (Production method) A glossy cream was obtained according to Examples 2, 3, and 4. It was confirmed through actual use tests that Example 10 can be used not only for cosmetics but also for furniture polishing creams.

Claims (1)

【特許請求の範囲】 1 有機変性粘土鉱物を一般式()、()また
は()で示されるポリオキシアルキレン変性オ
ルガノポリシロキサンの一種または二種以上で処
理して得られる乳化剤組成物。 2 ポリオキシアルキレン変性オルガノポリシロ
キサンの含有量が有機変性粘土鉱物100gに対し
て5〜600gである特許請求の範囲第1項記載の
乳化剤組成物。 {一般式()、()、()中、Rはメチル基ま
たは一部がフエニル基、R′は水素または炭素数
1〜12のアルキル基、pは1〜5の数、qは2〜
3の数、x、m、nは平均数でポリオキシアルキ
レン変性オルガノポリシロキサンが分子中にポリ
オキシアルキレン基を20〜40重量%(20重量%含
まず)含有し且つ該ポリオキシアルキレン変性オ
ルガノポリシロキサンの粘度が25℃において5〜
3000センチストークスになるような数値を表す。}
[Scope of Claims] 1. An emulsifier composition obtained by treating an organically modified clay mineral with one or more polyoxyalkylene-modified organopolysiloxanes represented by the general formula (), (), or (). 2. The emulsifier composition according to claim 1, wherein the content of polyoxyalkylene-modified organopolysiloxane is 5 to 600 g per 100 g of organically modified clay mineral. {In the general formulas (), (), (), R is a methyl group or partially a phenyl group, R' is hydrogen or an alkyl group having 1 to 12 carbon atoms, p is a number from 1 to 5, and q is a number from 2 to
The numbers 3, x, m, and n are average numbers, and the polyoxyalkylene-modified organopolysiloxane contains 20 to 40% by weight (excluding 20% by weight) of polyoxyalkylene groups in the molecule, and The viscosity of polysiloxane is 5~5 at 25℃
Represents a number that equals 3000 centistokes. }
JP60051949A 1985-03-15 1985-03-15 Emulsifying agent composition Granted JPS61212321A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP60051949A JPS61212321A (en) 1985-03-15 1985-03-15 Emulsifying agent composition

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP60051949A JPS61212321A (en) 1985-03-15 1985-03-15 Emulsifying agent composition

Publications (2)

Publication Number Publication Date
JPS61212321A JPS61212321A (en) 1986-09-20
JPH0468015B2 true JPH0468015B2 (en) 1992-10-30

Family

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Family Applications (1)

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Families Citing this family (16)

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Publication number Priority date Publication date Assignee Title
US5132047A (en) * 1988-02-09 1992-07-21 Shin-Etsu Chemical Co., Ltd. Organopolysiloxane emulsion composition
JP2544045B2 (en) * 1991-10-01 1996-10-16 信越化学工業株式会社 Water-in-oil type silicone emulsion composition
JP3895016B2 (en) * 1997-09-30 2007-03-22 富士ケミカル株式会社 Antibacterial paste
FR2776514B1 (en) * 1998-03-26 2001-03-09 Oreal W / O EMULSION, COMPOSITION COMPRISING SUCH AN EMULSION AND USE IN COSMETICS, PHARMACY OR HYGIENE
FR2776513B1 (en) * 1998-03-26 2001-04-20 Oreal W / O EMULSION, COMPOSITION COMPRISING SUCH AN EMULSION AND USE IN COSMETICS, PHARMACY OR HYGIENE
ES2371026T3 (en) * 2001-10-19 2011-12-26 Atritech, Inc. ADJUSTABLE OCLUSION DEVICE IN THE LEFT HEADPHONE OREJUELA.
GB0207850D0 (en) * 2002-04-04 2002-05-15 Unilever Plc Fabric treatment compositions
FR2854572B1 (en) * 2003-05-05 2006-08-11 Oreal COSMETIC COMPOSITION FOR THE CARE AND / OR MAKE-UP OF SKIN, LIPS AND PHANES
FR2854571B1 (en) * 2003-05-05 2006-08-11 Oreal TRANSLUCENT OR TRANSPARENT COSMETIC COMPOSITION
JP4566124B2 (en) * 2005-12-14 2010-10-20 株式会社資生堂 Water-in-oil emulsified cosmetic
KR20090037450A (en) 2006-08-09 2009-04-15 가부시키가이샤 시세이도 Sol composition containing organomodified clay mineral having flaky particle structure, oil-base gel compositions and w/o emulsion compositions containing the same
JP5492373B2 (en) * 2006-08-09 2014-05-14 株式会社 資生堂 Oily gel composition containing organically modified clay mineral having plate-like particle structure, and W / O type emulsified composition using the same
JP2010144157A (en) 2008-12-22 2010-07-01 Dow Corning Toray Co Ltd Emulsified product, method for producing the same, and cosmetic raw material comprising the emulsified product
JP5583906B2 (en) 2008-12-22 2014-09-03 東レ・ダウコーニング株式会社 Partially hydrocarbon group-blocked (poly) glycerol-modified polysiloxane, method for producing the same, and cosmetics containing the polysiloxane
JP5430142B2 (en) 2008-12-22 2014-02-26 東レ・ダウコーニング株式会社 Method for producing emulsion
KR20160077757A (en) 2014-12-24 2016-07-04 주식회사 엘지생활건강 Cosmetic composition which contains oil-dispersing

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5334854A (en) * 1976-09-14 1978-03-31 Toray Silicone Co Ltd Self-emulsifiable silicone composition
JPS5484883A (en) * 1977-11-22 1979-07-06 Peterson Puritan Inc Water in oil emulsion* its manufacture and liquid composition containing said emulsion

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5334854A (en) * 1976-09-14 1978-03-31 Toray Silicone Co Ltd Self-emulsifiable silicone composition
JPS5484883A (en) * 1977-11-22 1979-07-06 Peterson Puritan Inc Water in oil emulsion* its manufacture and liquid composition containing said emulsion

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