JP2004123727A5 - - Google Patents

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JP2004123727A5
JP2004123727A5 JP2003306796A JP2003306796A JP2004123727A5 JP 2004123727 A5 JP2004123727 A5 JP 2004123727A5 JP 2003306796 A JP2003306796 A JP 2003306796A JP 2003306796 A JP2003306796 A JP 2003306796A JP 2004123727 A5 JP2004123727 A5 JP 2004123727A5
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従来、水中油乳化剤形の皮膚外用剤は、さっぱり感等の優れた使用感を有しており、多用されてきており、メークアップ化粧料としても重用されてきた。しかしながら、肌からの水分の蒸散防止などのエモリエント機能に劣っており、スキンケア機能の面から見て物足りなさを感じるという問題点を有していた。これらの課題を解決するために、多価アルコール類、ヒアルロン酸ナトリウム等の保湿剤を添加するという策が施されたりしてきたが、前者は効果を上げるためには多量に添加しなくてはならず、また、後者は水溶液自体が非常なべたつき感を有するので、水中油乳化剤形の皮膚外用剤の良好な使用感を損なうことが多く、抜本的な解決策には至っていない。(例えば、特許文献1、特許文献2、特許文献3を参照)一方、後記一般式(I)〜一般式(IV)で表される化合物は、ポリマー或いはコポリマーの原料として知られているものである。しかしながら、これらの構成単位の構成比を変えて水溶性とし、水中油乳化剤形の皮膚外用剤に配合し、水中油乳化剤形の皮膚外用剤の良好な使用感触を維持しつつ、保湿機能を向上させるために使用することは全く知られていなかった。 BACKGROUND ART Conventionally, oil-in-water emulsified skin external preparations have an excellent feeling of use such as a refreshing feeling, have been frequently used, and have been used heavily as makeup cosmetics. However , it is inferior in emollient functions such as prevention of evaporation of moisture from the skin, and has a problem that it feels unsatisfactory in terms of skin care functions. In order to solve these problems, measures have been taken to add humectants such as polyhydric alcohols and sodium hyaluronate. In addition, since the aqueous solution itself has an extremely sticky feeling, the latter often impairs a good feeling of use of an external preparation for skin in the form of an oil-in-water emulsion, and has not yet reached a drastic solution. (See, for example, Patent Document 1, Patent Document 2, and Patent Document 3) On the other hand, compounds represented by the following general formulas (I) to (IV) are known as raw materials for polymers or copolymers. is there. However, by changing the constitutional ratio of these constituent units to make them water-soluble, and blending them into oil-in-water emulsified skin external preparations, and improving the moisturizing function while maintaining a good feeling of use of the oil-in-water emulsified skin external preparations It was not known at all to use.

Figure 2004123727
一般式(II)
(式(II)中、R3は水素原子又は炭素数1〜3のアルキル基を表し、R4は水酸基を有していてもよい炭素数2〜4のアルキレン基を表し、R5は水素原子、炭素数6〜20の芳香族基、炭素数1〜20の脂肪族炭化水素基、又は炭素数1〜20のアシル基を表す。nは4〜50の整数を表す。)
Figure 2004123727
General formula (II)
(In formula (II), R 3 represents an alkyl group having 1 to 3 hydrogen atoms or carbon atoms, R 4 represents an alkylene group having 2 to 4 carbon atoms which may have a hydroxyl group, R 5 is hydrogen Represents an atom, an aromatic group having 6 to 20 carbon atoms, an aliphatic hydrocarbon group having 1 to 20 carbon atoms, or an acyl group having 1 to 20 carbon atoms, and n represents an integer of 4 to 50.)

(2)前記一般式(II)で表されるモノマーから誘導される構成単位の含有量が全構成単位の2080重量%であることを特徴とする、(1)記載の水中油乳化剤形の皮膚外用剤。
(3)前記一般式(II)で表されるモノマーが、下記一般式(III)で表されるものであることを特徴とする、(1)又は(2)記載の水中油乳化剤形の皮膚外用剤。
(2) The oil-in-water emulsified dosage form according to (1), wherein the content of the structural unit derived from the monomer represented by the general formula (II) is 20 to 80% by weight of all the structural units. External preparation for skin.
(3) The oil-in-water emulsified skin according to (1) or (2), wherein the monomer represented by the general formula (II) is a monomer represented by the following general formula (III). External preparation.

Figure 2004123727
一般式(III)
(式(III)中、R6は水素原子又は炭素数1〜3のアルキル基を表し、R7は水素原子、炭素数6〜20の芳香族基、炭素数1〜20の脂肪族炭化水素基、又は炭素数1〜20のアシル基を表す。qは8〜40の整数を表す。)
Figure 2004123727
General formula (III)
(In the formula (III), R 6 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R 7 represents a hydrogen atom, an aromatic group having 6 to 20 carbon atoms, and an aliphatic hydrocarbon having 1 to 20 carbon atoms. Represents a group or an acyl group having 1 to 20 carbon atoms, and q represents an integer of 8 to 40.)

Figure 2004123727
一般式(II)
(式(II)中、R3は水素原子又は炭素数1〜3のアルキル基を表し、R4は水酸基を有していてもよい炭素数2〜4のアルキレン基を表し、R5は水素原子、炭素数6〜20の芳香族基、炭素数1〜20の脂肪族炭化水素基、又は炭素数1〜20のアシル基を表す。nは4〜50の整数を表す。)
Figure 2004123727
General formula (II)
(In formula (II), R 3 represents an alkyl group having 1 to 3 hydrogen atoms or carbon atoms, R 4 represents an alkylene group having 2 to 4 carbon atoms which may have a hydroxyl group, R 5 is hydrogen Represents an atom, an aromatic group having 6 to 20 carbon atoms, an aliphatic hydrocarbon group having 1 to 20 carbon atoms, or an acyl group having 1 to 20 carbon atoms, and n represents an integer of 4 to 50.)

Figure 2004123727
一般式(III)
(式(III)中、R6は水素原子又は炭素数1〜3のアルキル基を表し、R7は水素原子、炭素数6〜20の芳香族基、炭素数1〜20の脂肪族炭化水素基、又は炭素数1〜20のアシル基を表す。qは8〜40の整数を表す。)
Figure 2004123727
General formula (III)
(In the formula (III), R 6 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R 7 represents a hydrogen atom, an aromatic group having 6 to 20 carbon atoms, and an aliphatic hydrocarbon having 1 to 20 carbon atoms. Represents a group or an acyl group having 1 to 20 carbon atoms, and q represents an integer of 8 to 40.)

(6)前記コポリマーをエモリエント剤として含有することを特徴とする、(1)〜(5)何れか1項に記載の水中油乳化剤形の皮膚外用剤。
(7)エモリエント剤としての機能が、経皮的水分散逸抑制効果であることを特徴とする(6)に記載の水中油乳化剤形の皮膚外用剤。
(6) The skin external preparation in the form of an oil-in-water emulsion according to any one of (1) to (5), which comprises the copolymer as an emollient.
(7) The skin external preparation in the form of an oil-in-water emulsion according to (6), wherein the function as an emollient agent is a transdermal water dispersion loss suppressing effect.

式(II)中、R3は水素原子又は炭素数1〜3のアルキル基を表し、R4は水酸基を有していてもよい炭素数2〜4のアルキレン基を表し、R5は水素原子、炭素数6〜20の芳香族基、炭素数1〜20の脂肪族炭化水素基、又は炭素数1〜20のアシル基を表す。nは4〜50の整数を表す。 In the formula (II), R 3 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, R 4 represents an alkylene group having 2 to 4 carbon atoms which may have a hydroxyl group, and R 5 is a hydrogen atom Represents an aromatic group having 6 to 20 carbon atoms, an aliphatic hydrocarbon group having 1 to 20 carbon atoms, or an acyl group having 1 to 20 carbon atoms. n represents an integer of 4 to 50.

5の基のうち、炭素数6〜20の芳香族基としては、フェニル基、ベンジル基、メチルフェニル基、エチルフェニル基等が例示できる。炭素数1〜20の脂肪族炭化水素基としては、例えば、メチル基、エチル基、ブチル基、ターシャリーブチル基、ヘキシル基、シクロへキシル基、オクチル基、2−エチルへキシル基、ラウリル基、ミリスチル基、パルミチル基、ステアリル基、オレイル基などが好適に例示できる。炭素数1〜20のアシル基としては、アセチル基、ブテノイル基、カプリロイル基、カプリノイル基、ベンゾイル基、ラウロイル基、ミリストイル基、パルミトイル基、ステアロイル基、オレオイル基などが好適に例示できる。これらのうち、R5の基として特に好ましいものは、炭素数1〜12のアルキル基(脂肪族炭化水素基)である。nは4〜50の整数であり、好ましくは8〜40である。 Of the groups of R 5, examples of the aromatic group having 6 to 20 carbon atoms, a phenyl group, a benzyl group, methylphenyl group, ethylphenyl group and the like. Examples of the aliphatic hydrocarbon group having 1 to 20 carbon atoms include a methyl group, an ethyl group, a butyl group, a tert-butyl group, a hexyl group, a cyclohexyl group, an octyl group, a 2-ethylhexyl group, and a lauryl group. , Myristyl, palmityl, stearyl, oleyl and the like. Preferred examples of the acyl group having 1 to 20 carbon atoms include an acetyl group, a butenoyl group, a capryloyl group, a caprynoyl group, a benzoyl group, a lauroyl group, a myristoyl group, a palmitoyl group, a stearoyl group, and an oleoyl group. Among these, an alkyl group having 1 to 12 carbon atoms (aliphatic hydrocarbon group) is particularly preferred as the group represented by R 5 . n is an integer of 4 to 50, preferably 8 to 40.

Figure 2004123727
一般式(III)
(式(III)中、R6は水素原子又は炭素数1〜3のアルキル基を表し、R7は水素原子、炭素数6〜20の芳香族基、炭素数1〜20の脂肪族炭化水素基、又は炭素数1〜20のアシル基を表す。qは8〜40の整数を表す。)
Figure 2004123727
General formula (III)
(In the formula (III), R 6 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R 7 represents a hydrogen atom, an aromatic group having 6 to 20 carbon atoms, and an aliphatic hydrocarbon having 1 to 20 carbon atoms. Represents a group or an acyl group having 1 to 20 carbon atoms, and q represents an integer of 8 to 40.)

かくして得られた、コポリマーは、後記実施例に示すように、これを皮膚に投与することにより、皮膚上に形成したべたつきのない皮膜によって、経皮的水分散逸量を抑制し、以て皮膚に於ける保湿機能を高めるため、皮膚外用剤においてはエモリエント剤として機能する。この為、水中油乳化剤形の、「さっぱりとした使用感」を損なうことなく、保湿機能を発揮できる。 The copolymer thus obtained is applied to the skin to suppress the amount of transcutaneous water dispersion lost by the non- sticky film formed on the skin, as shown in the Examples below, and thus the copolymer is applied to the skin. It functions as an emollient in skin external preparations to enhance the moisturizing function in the skin. For this reason, the moisturizing function can be exhibited without impairing the “fresh feeling of use” of the oil-in-water emulsified form.

製造例7〜11
製造例6に準じて、原料を変えて一般式(II)に表されるモノマーを作成した
Production Examples 7 to 11
According to Production Example 6, the raw material was changed to prepare a monomer represented by the general formula (II) .

Claims (7)

一般式(I)で表されるモノマーから誘導される構成単位の一種以上と、一般式(II)で表されるモノマーから誘導される構成単位の一種以上とを含み、且つ前記一般式(I)で表されるモノマーから誘導される構成単位の含有量が全構成単位の5〜25重量%であることを特徴とするコポリマーを含有してなる水中油乳化剤形の皮膚外用剤。
Figure 2004123727
一般式(I)
(式(I)中、R1は水素原子又は炭素数1〜3のアルキル基を表し、R2は8〜21個の置換フッ素原子を有する炭素数5〜12のアルキル基を表す。)
Figure 2004123727
一般式(II)
(式(II)中、R3は水素原子又は炭素数1〜3のアルキル基を表し、R4は水酸基を有していてもよい炭素数2〜4のアルキレン基を表し、R5は水素原子、炭素数6〜20の芳香族基、炭素数1〜20の脂肪族炭化水素基、又は炭素数1〜20のアシル基を表す。nは4〜50の整数を表す。)
It contains at least one structural unit derived from the monomer represented by the general formula (I) and at least one structural unit derived from the monomer represented by the general formula (II), and further includes the above-mentioned general formula (I 3.) An external preparation for skin in the form of an oil-in-water emulsion, comprising a copolymer, wherein the content of the structural unit derived from the monomer represented by the formula (1) is from 5 to 25% by weight of the total structural unit.
Figure 2004123727
General formula (I)
(In the formula (I), R 1 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R 2 represents an alkyl group having 5 to 12 carbon atoms having 8 to 21 substituted fluorine atoms.)
Figure 2004123727
General formula (II)
(In formula (II), R 3 represents an alkyl group having 1 to 3 hydrogen atoms or carbon atoms, R 4 represents an alkylene group having 2 to 4 carbon atoms which may have a hydroxyl group, R 5 is hydrogen Represents an atom, an aromatic group having 6 to 20 carbon atoms, an aliphatic hydrocarbon group having 1 to 20 carbon atoms, or an acyl group having 1 to 20 carbon atoms, and n represents an integer of 4 to 50.)
前記一般式(II)で表されるモノマーから誘導される構成単位の含有量が全構成単位の2080重量%である事を特徴とする、請求項1記載の水中油乳化剤形の皮膚外用剤。 The oil-in-water emulsified dosage form according to claim 1, wherein the content of the structural unit derived from the monomer represented by the general formula (II) is 20 to 80% by weight of the total structural unit. Agent. 前記一般式(II)で表されるモノマーが、下記一般式(III)で表されるものであることを特徴とする、請求項1または2記載の水中油乳化剤形の皮膚外用剤。
Figure 2004123727
一般式(III)
(式(III)中、R6は水素原子又は炭素数1〜3のアルキル基を表し、R7は水素原子、炭素数6〜20の芳香族基、炭素数1〜20の脂肪族炭化水素基、又は炭素数1〜20のアシル基を表す。qは8〜40の整数を表す。)
The skin external preparation in the form of an oil-in-water emulsion according to claim 1 or 2, wherein the monomer represented by the general formula (II) is a monomer represented by the following general formula (III).
Figure 2004123727
General formula (III)
(In the formula (III), R 6 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R 7 represents a hydrogen atom, an aromatic group having 6 to 20 carbon atoms, and an aliphatic hydrocarbon having 1 to 20 carbon atoms. Represents a group or an acyl group having 1 to 20 carbon atoms, and q represents an integer of 8 to 40.)
1)一般式(I)で表されるモノマーから誘導される構成単位の一種以上を5〜9.8重量%、2)一般式(II)で表されるモノマーから誘導される構成単位の一種以上を30.2〜45重量%、及び3)一般式(IV)で表されるモノマーから誘導される構成単位の一種以上を50〜60重量%含有してなるコポリマーを含有する水中油乳化剤形の皮膚外用剤。
Figure 2004123727
一般式(I)
(式(I)中、R1は水素原子又は炭素数1〜3のアルキル基を表し、R2は8〜21個の置換フッ素原子を有する炭素数5〜12のアルキル基を表す。)
Figure 2004123727
一般式(II)
(式(II)中、R3は水素原子又は炭素数1〜3のアルキル基を表し、R4は水酸基有していてもよい炭素数2〜4のアルキレン基を表し、R5は水素原子、炭素数6〜20の芳香族基、炭素数1〜20の脂肪族炭化水素基、又は炭素数1〜20のアシル基を表す。nは4〜50の整数を表す。)
Figure 2004123727
一般式(IV)
(式(IV)中、R8は水素原子又は炭素数1〜3のアルキル基を表し、R9は炭素数1〜3のアルキル基を表す。)
1) 5 to 9.8% by weight of one or more structural units derived from the monomer represented by the general formula (I) 2) One type of structural unit derived from the monomer represented by the general formula (II) 30.2 to 45% by weight of the above, and 3) an oil-in-water emulsified form containing a copolymer containing 50 to 60% by weight of one or more structural units derived from a monomer represented by the general formula (IV). External preparation for skin.
Figure 2004123727
General formula (I)
(In the formula (I), R 1 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R 2 represents an alkyl group having 5 to 12 carbon atoms having 8 to 21 substituted fluorine atoms.)
Figure 2004123727
General formula (II)
(In the formula (II), R 3 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, R 4 represents an alkylene group having 2 to 4 carbon atoms which may have a hydroxyl group, and R 5 represents a hydrogen atom Represents an aromatic group having 6 to 20 carbon atoms, an aliphatic hydrocarbon group having 1 to 20 carbon atoms, or an acyl group having 1 to 20 carbon atoms, and n represents an integer of 4 to 50.)
Figure 2004123727
General formula (IV)
(In the formula (IV), R 8 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R 9 represents an alkyl group having 1 to 3 carbon atoms.)
前記一般式(II)に表されるモノマーが、下記一般式(III)で表されるものであることを特徴とする、請求項4に記載の水中油乳化剤形の皮膚外用剤。
Figure 2004123727
一般式(III)
(式(III)中、R6は水素原子又は炭素数1〜3のアルキル基を表し、R7は水素原子、炭素数6〜20の芳香族基、炭素数1〜20の脂肪族炭化水素基、又は炭素数1〜20のアシル基を表す。qは8〜40の整数を表す。)
The skin external preparation according to claim 4, wherein the monomer represented by the general formula (II) is a monomer represented by the following general formula (III).
Figure 2004123727
General formula (III)
(In the formula (III), R 6 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R 7 represents a hydrogen atom, an aromatic group having 6 to 20 carbon atoms, and an aliphatic hydrocarbon having 1 to 20 carbon atoms. Represents a group or an acyl group having 1 to 20 carbon atoms, and q represents an integer of 8 to 40.)
前記コポリマーをエモリエント剤として含有することを特徴とする、請求項1〜5何れか1項に記載の水中油乳化剤形の皮膚外用剤。 The skin external preparation in the form of an oil-in-water emulsion, according to any one of claims 1 to 5, wherein the copolymer is contained as an emollient. エモリエント剤としての機能が、経皮的水分散逸抑制効果であることを特徴とする請求項6に記載の水中油乳化剤形の皮膚外用剤。 The skin external preparation in the form of an oil-in-water emulsion according to claim 6, wherein the function as an emollient agent is a transdermal water dispersion loss suppressing effect.
JP2003306796A 2002-09-13 2003-08-29 Skin external preparation in oil-in-water emulsifier form Expired - Fee Related JP4150646B2 (en)

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JP5063946B2 (en) * 2006-07-14 2012-10-31 花王株式会社 Oil-in-water emulsion composition
JP5348877B2 (en) * 2007-12-10 2013-11-20 花王株式会社 Oil-in-water emulsified cosmetic
JP5348876B2 (en) * 2007-12-10 2013-11-20 花王株式会社 Oil-in-water emulsified cosmetic
JP6001385B2 (en) * 2012-08-31 2016-10-05 ポーラ化成工業株式会社 Multilayer cream

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