JP2008031118A - Cleansing agent composition for makeup cleansing - Google Patents

Cleansing agent composition for makeup cleansing Download PDF

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JP2008031118A
JP2008031118A JP2006208321A JP2006208321A JP2008031118A JP 2008031118 A JP2008031118 A JP 2008031118A JP 2006208321 A JP2006208321 A JP 2006208321A JP 2006208321 A JP2006208321 A JP 2006208321A JP 2008031118 A JP2008031118 A JP 2008031118A
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cleansing
makeup
integer
oil
nonionic surfactant
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Goro Hashimoto
橋本吾郎
Tokuo Nakane
中根徳雄
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Toho Chemical Industry Co Ltd
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Toho Chemical Industry Co Ltd
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Abstract

<P>PROBLEM TO BE SOLVED: To provide a cleansing agent composition for makeup cleansing having good preservation stability, excellent cleansing power for makeup stains and an excellent feeling of use. <P>SOLUTION: The cleansing agent composition for makeup cleansing comprises a nonionic surfactant represented by general formula (1): R<SP>1</SP>O-EO<SB>x</SB>-AO<SB>y</SB>-EO<SB>z</SB>-R<SP>2</SP>(wherein, R<SP>1</SP>is an 8-22C straight-chain or branched chain saturated or unsaturated fatty acid residue; R<SP>2</SP>is a 1-4C straight-chain or branched chain short chain alkyl group; EO is an ethylene oxide unit; AO is a ≥3C alkylene oxide unit; x is an integer of ≥1; y is an integer of 2-10; and z is an integer of ≥1). <P>COPYRIGHT: (C)2008,JPO&INPIT

Description

本発明は、保存安定性が良好で、メイク汚れに対する洗浄力に優れ、尚且つ使用感に優れたメイククレンジング用洗浄剤組成物に関する。 The present invention relates to a cleansing composition for makeup cleansing that has good storage stability, excellent cleaning power against makeup stains, and excellent usability.

メイククレンジング用洗浄剤は石鹸など水性洗浄料で落としにくいメイクアップ化粧品を効果的に除去する目的で使用され、油性汚れを溶解・分散し、ふき取りや洗い流しによって除去する効果をもつ。 Makeup cleansing detergents are used to effectively remove makeup cosmetics that are difficult to remove with soap and other aqueous detergents, and have the effect of dissolving and dispersing oily stains and removing them by wiping or washing away.

一般に溶剤型と呼ばれるメイククレンジング洗浄剤はクレンジングクリーム、クレンジングミルク、クレンジングローション、クレンジングジェル、クレンジングオイル等の形態があり、それぞれの使用性によって使い分けされている。 The makeup cleansing detergent generally called solvent type has forms such as cleansing cream, cleansing milk, cleansing lotion, cleansing gel, cleansing oil, and the like, and they are properly used depending on their respective usability.

最近は水や汗による化粧崩れを防ぐ製剤の開発が進められており、このような落ちにくい化粧を落とす為に、高い洗浄力を有するメイククレンジング用洗浄剤が求められている。 In recent years, preparations for preventing makeup collapse due to water and sweat have been developed, and in order to remove such difficult makeup, there is a need for a makeup cleansing detergent having a high detergency.

さらにこのような製剤は高温下(40℃以上)、低温下(0℃以下)いずれにおいても保管される場合がある為、分離・白濁など商品価値を損なう事が無い様、保存安定性が高い製剤も同時に求められている。 Furthermore, since such preparations may be stored at both high temperatures (above 40 ° C) and low temperatures (below 0 ° C), they have high storage stability so as not to impair commercial value such as separation and cloudiness. There is also a need for formulations.

一般的に油分を多量に含むクレンジング化粧料は落ちにくい化粧、汚れに対してクレンジング効果が高いが、洗い流し時にべた付き、ヌルつきが生じ、また洗いあがり後に油性感が残ってしまう。また、保存安定性が悪いという欠点がある。 In general, cleansing cosmetics containing a large amount of oil have a high cleansing effect against makeup and stains that are difficult to remove, but stickiness and nulliness are generated during washing, and an oily feeling remains after washing. In addition, there is a drawback that storage stability is poor.

油分を減らすことで油性感を低減させることはある程度できるが、油分を多量に含むクレンジング化粧料の特徴である落ちにくい化粧、汚れに対しての高いクレンジング効果を発揮できなくなる。その一方、アニオン活性剤を配合することで油性感を低減し、クレンジング効果は高められるが、皮膚安全性の点での問題が危惧される。 Although the oily feeling can be reduced to some extent by reducing the oil content, it is impossible to exhibit the high cleansing effect against makeup and stains that are difficult to remove, which is a characteristic of cleansing cosmetics containing a large amount of oil. On the other hand, by adding an anionic active agent, the oily feeling is reduced and the cleansing effect is enhanced, but there are concerns about problems in terms of skin safety.

また、これらのものは油性感の低減は改善されているものの十分とは言えず、保存安定性も十分でないことから温度によって霞みがかった外観になったり、沈殿が生じたりしてしまい、商品価値と使用性を損なってしまう問題があった。 In addition, although these oils have improved oily feeling, they cannot be said to be sufficient, and storage stability is not sufficient, resulting in a smoky appearance due to temperature or precipitation, resulting in commercial value. And there was a problem that would impair usability.

これらに対して特許文献1や特許文献2のように油性感の低減及び、保存安定性の向上に対して様々な試みが示されている。特許文献1にはHLBが5〜15の非イオン界面活性剤と液体油を必須成分とする非水クレンジング料が開示されているが、油性感の低減に関しては改善されているものの、保存安定性は十分ではない。特許文献2にはHLB7〜14の非イオン界面活性剤と水、常温で液体の油を配合するクレンジング化粧料が開示されているが、保存安定性がある程度改善されているものの、未だ十分とは言えない。 On the other hand, as in Patent Document 1 and Patent Document 2, various attempts have been made to reduce oiliness and improve storage stability. Patent Document 1 discloses a non-aqueous cleansing agent containing a nonionic surfactant having an HLB of 5 to 15 and a liquid oil as essential components. However, although the oily feeling is improved, the storage stability is improved. Is not enough. Patent Document 2 discloses a cleansing cosmetic comprising a nonionic surfactant of HLB7-14, water, and oil that is liquid at room temperature, but although the storage stability has been improved to some extent, it is still insufficient I can not say.

この中で油性汚れに対して高い洗浄力有し、低温安定性が良好で使用感に優れる洗浄剤組成物として特許文献3にはポリオキシアルキレンアルキルエーテルと界面活性剤を含有することを特徴とする毛髪又は皮膚用洗浄剤組成物が開示されており、メイクアップ汚れ等に高い洗浄力を有し、低温安定性が良好で使用感に優れるとしているが、感触面で改善はされているものの、寒冷地における保存安定性については改善の余地があった。 Among them, Patent Document 3 is characterized by containing a polyoxyalkylene alkyl ether and a surfactant as a detergent composition having high detergency against oily soil, good low-temperature stability and excellent usability. Hair or skin cleaning composition is disclosed, has a high detergency to makeup stains, etc., has good low-temperature stability and excellent usability, but is improved in feel There was room for improvement in storage stability in cold regions.

特開昭62−108806号公報JP-A 62-108806 特開平3−161428号公報Japanese Patent Laid-Open No. 3-161428 特開平11−148091号公報JP-A-11-148091

本発明は、メイク汚れに対する洗浄力に優れ、尚且つ使用感に優れたメイククレンジング用洗浄剤組成物であって、従来のものよりもより広い温度範囲で保存安定性に優れたメイククレンジング用洗浄剤組成物を提供することを課題とする。 The present invention is a cleansing composition for makeup cleansing that has an excellent detergency against makeup stains and is also excellent in usability, and is a cleanser for makeup cleansing that has excellent storage stability in a wider temperature range than conventional ones. It is an object to provide an agent composition.

かかる実情において、本発明者らは上記課題を解決する為に鋭意研究を重ねた結果、特定の非イオン界面活性剤を含むことを特徴とするメイククレンジング用洗浄剤組成物が、従来のよりも寒冷地における保存安定性が特に良好で、油性汚れ、皮脂汚れ等に対する洗浄力に優れ、尚且つ使用感に優れることを見出し、本発明を完成するに至った。 Under such circumstances, the present inventors have conducted extensive research to solve the above problems, and as a result, a makeup cleansing composition comprising a specific nonionic surfactant is more than conventional. The present inventors have found that the storage stability in a cold region is particularly good, that they are excellent in detergency against oily soil, sebum soil, and the like, and that they have excellent usability, and thus completed the present invention.

すなわち、本発明は下記一般式(1)で表される非イオン界面活性剤を含むことを特徴とするメイククレンジング用洗浄剤組成物である。
O-(EO)-(AO)-(EO)-R (1)
:炭素数8〜22の直鎖または分岐鎖状の飽和または不飽和脂肪酸残基
:炭素数1〜4の直鎖または分岐鎖状の短鎖アルキル基
EO:エチレンオキサイド単位
AO:炭素数3以上のアルキレンオキサイド単位
x:1以上の整数
y:2〜10の整数
z:1以上の整数
That is, the present invention is a makeup cleansing composition comprising a nonionic surfactant represented by the following general formula (1).
R 1 O- (EO) x - (AO) y - (EO) z -R 2 (1)
R 1 : linear or branched saturated or unsaturated fatty acid residue having 8 to 22 carbon atoms R 2 : linear or branched short chain alkyl group having 1 to 4 carbon atoms EO: ethylene oxide unit AO: Alkylene oxide unit having 3 or more carbon atoms x: integer of 1 or more y: integer of 2 to 10 z: integer of 1 or more

本発明の好ましい態様として、前記非イオン界面活性剤が常温で液状のものであることを特徴とするメイククレンジング用洗浄剤組成物がある。   As a preferred embodiment of the present invention, there is a makeup cleansing composition wherein the nonionic surfactant is liquid at room temperature.

また本発明の別の好ましい態様として、前記非イオン界面活性剤の脂肪酸残基がイソステアリン酸、オレイン酸由来のものであることを特徴とするメイククレンジング用洗浄剤組成物がある。 Another preferred embodiment of the present invention is a makeup cleansing composition wherein the fatty acid residue of the nonionic surfactant is derived from isostearic acid or oleic acid.

更に本発明の別の好ましい態様として、炭化水素油、エステル油、シリコン油、植物油から選ばれる1種以上の常温で液体の油を含むことを特徴とする前記メイククレンジング用洗浄剤組成物がある。 Furthermore, as another preferred embodiment of the present invention, there is provided the above-mentioned cleansing composition for makeup cleansing, comprising one or more liquid oils at normal temperature selected from hydrocarbon oils, ester oils, silicone oils and vegetable oils. .

本発明の特定の非イオン界面活性剤を含むことを特徴とするメイククレンジング用洗浄剤組成物は、従来のものよりもより広い温度範囲で保存安定性が良好で、油性汚れ、皮脂汚れ等に対する洗浄力に優れ、尚且つ使用感に優れる洗浄剤組成物を提供することができる。   The cleansing composition for makeup cleansing characterized by containing the specific nonionic surfactant of the present invention has good storage stability in a wider temperature range than conventional ones, and is suitable for oily dirt, sebum dirt, etc. A cleaning composition having excellent detergency and excellent usability can be provided.

本発明で用いられる特定の非イオン界面活性剤は、前記一般式(1)で表されるものであり、Rは炭素数8〜24の直鎖または分岐鎖状の飽和または不飽和脂肪酸残基である。例えば、直鎖状の飽和脂肪酸としてはオクタン酸、デセン酸、ラウリン酸、ミリスチン酸、パルミチン酸、ステアリン酸、ベヘニン酸等が挙げられ、直鎖状の不飽和脂肪酸としてはオレイン酸、リノール酸、リノレン酸等が挙げられる。分岐鎖状飽和脂肪酸としてはオクチル酸、3,5,5−トリメチルヘキサン酸イソヘプタン酸、イソミリスチン酸、イソパルミチン酸、イソステアリン酸、イソアラキン等が挙げられ、分岐状不飽和脂肪酸としては2,5−ジメチル−2−ヘプタデセン酸等が挙げられるが、これらの中で低温時の保存安定性とハンドリング性の点で特にイソステアリン酸、オレイン酸が好ましい。 The specific nonionic surfactant used in the present invention is represented by the general formula (1), and R 1 is a residue of a linear or branched saturated or unsaturated fatty acid having 8 to 24 carbon atoms. It is a group. For example, linear saturated fatty acids include octanoic acid, decenoic acid, lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, etc., and linear unsaturated fatty acids include oleic acid, linoleic acid, Examples include linolenic acid. Examples of branched saturated fatty acids include octylic acid, 3,5,5-trimethylhexanoic acid isoheptanoic acid, isomyristic acid, isopalmitic acid, isostearic acid, isoarachin, and the like. Examples thereof include dimethyl-2-heptadecenoic acid, and among these, isostearic acid and oleic acid are particularly preferable in terms of storage stability at low temperatures and handling properties.

また、一般式(1)においてRは炭素数1〜4の直鎖または分岐鎖状のアルキル基であり、使用時の感触の点で好ましくは炭素数1である。炭素数4を超えると洗い流し時にべた付き、ヌルつきが生じ、また洗いあがり後に油性感が残り感触が悪くなってしまう。 Further, in the general formula (1), R 2 is a linear or branched alkyl group having 1 to 4 carbon atoms, and preferably 1 carbon atom from the point of touch during use. If the number of carbon atoms exceeds 4, stickiness and nulliness will occur during washing, and an oily feeling will remain after washing, resulting in a poor feel.

さらに、一般式(1)においてEO付加モル数であるx及びzは1以上の整数で、好ましくはxは3〜9の整数で、zは1〜5の整数である。x及びzが0の場合、油分との相溶性、保存安定性に問題は無いが、油性感が残り感触が悪くなってしまう。PO付加モル数であるyは2〜10の整数であり、好ましくは4〜6の整数である。yが2未満の場合、油分との相溶性が悪くなり、また保存安定性に問題が出てしまう。yが10を越えると油との相溶性、保存安定性は良くなるが、油性感が残り感触が悪くなってしまう。 Furthermore, in General Formula (1), x and z which are EO addition mole numbers are an integer greater than or equal to 1, Preferably x is an integer of 3-9, z is an integer of 1-5. When x and z are 0, there is no problem in the compatibility with the oil and storage stability, but the oily feeling remains and the touch becomes poor. Y which is the PO addition mole number is an integer of 2 to 10, and preferably an integer of 4 to 6. When y is less than 2, the compatibility with the oil is deteriorated, and the storage stability is problematic. If y exceeds 10, the compatibility with oil and storage stability are improved, but the oily feeling remains and the feel becomes poor.

この非イオン界面活性剤は通常の方法のように、短鎖アルコールにアルカリ触媒下で順にエチレンオキサイド、プロピレンオキサイド、エチレンオキサイドをブロック付加し製造したポリオキシアルキレンアルキルエーテルに、脂肪酸を120〜230℃で酸又はアルカリ触媒の存在下で脱水反応をするなど、一般的な方法によって製造することが出来る。   This nonionic surfactant is a polyoxyalkylene alkyl ether produced by block addition of ethylene oxide, propylene oxide and ethylene oxide in the order of an alkali catalyst to a short-chain alcohol in the usual manner, and a fatty acid at 120 to 230 ° C. And can be produced by a general method such as dehydration reaction in the presence of an acid or alkali catalyst.

本発明のメイククレンジング用洗浄剤組成物に炭化水素油、エステル油、シリコン油、植物油から選ばれる1種以上の常温で液体の油を配合することにより、より優れたメイククレンジング効果が得られる。炭化水素油としては例えば流動パラフィン、スクワラン、ワセリン、マイクロクリスタリンワックス等が、エステル油としては例えば2−エチルヘキサン酸セチル、パルミチン酸イソプロピル、ミリスチン酸オクチルドデシル、ミリスチン酸イソプロピル、イソノナン酸イソデシル、トリ−2−エチルヘキサン酸グリセリル、テトラ−2−エチルヘキサン酸ペンタエリスリトール等が、シリコン油としてはジメチルポリシロキサン、ポリメチルシクロシロキサン、ポリエーテル変性メチルポリシロキサン、アミノ酸変性ジメチルポリシロキサン等が、植物油としてはオリーブ油、サフラワー油、ツバキ油等が挙げられるがこれらに限定されるものではない。 A more excellent makeup cleansing effect can be obtained by blending the cleansing composition for makeup cleansing of the present invention with one or more liquid oils at normal temperature selected from hydrocarbon oil, ester oil, silicone oil and vegetable oil. Examples of hydrocarbon oils include liquid paraffin, squalane, petrolatum, and microcrystalline wax.Examples of ester oils include cetyl 2-ethylhexanoate, isopropyl palmitate, octyldodecyl myristate, isopropyl myristate, isodecyl isononanoate, tri- Glyceryl 2-ethylhexanoate, pentaerythritol tetra-2-ethylhexanoate, etc. are silicon oils such as dimethylpolysiloxane, polymethylcyclosiloxane, polyether-modified methylpolysiloxane, amino acid-modified dimethylpolysiloxane, etc. Examples include olive oil, safflower oil, camellia oil and the like, but are not limited thereto.

また、本発明の効果を損なわない程度に、その用途の必要性に応じて他の成分を配合することができる。 Moreover, other components can be mix | blended according to the necessity of the use to such an extent that the effect of this invention is not impaired.

メイククレンジング用洗浄剤組成物の形状としてはクリーム状、ミルク状、ローション状、ジェル状、オイル状のいかような形態でも取ることができ、従来の製剤化技術において製造することができる。 The form of the cleansing composition for makeup cleansing can be any form such as cream, milk, lotion, gel or oil, and can be produced by conventional formulation techniques.

以下に本発明を実施例に基づいてさら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。特に指定のない限り、配合量は質量%で示す。   The present invention will be described below in more detail based on examples, but the present invention is not limited thereto. Unless otherwise specified, the amount is expressed in mass%.

(前記一般式(1)の非イオン界面活性剤の製造)
[実施例1]
(POE(5)POP(5)POE(3)メチルエーテルイソステアレートの製造)
5LオートクレーブにハイモールTM(東邦化学(株)製、ポリオキシエチレン(3)メチルエーテル)950gとKOH 7.8gを仕込み十分に窒素置換をした後、減圧下100〜110℃でアルコラート化を行った後、120〜130℃に昇温し密閉下でプロピレンオキサイド1683gを4時間かけて滴下し、圧変化が無くなるまで熟成した。続けて160〜170℃に昇温し、エチレンオキサイド1274gを2時間かけて滴下し圧変化が無くなるまで熟成した。60℃以下まで冷却した後、10%シュウ酸水溶液で触媒を中和した後、減圧脱水しPOE(5)POP(5)POP(3)メチルエーテルを得た。この内容物3500gとイソステアリン酸1430g、炭酸カリウム12gを5Lフラスコを仕込み十分に窒素置換をした後、200〜210℃まで昇温し、10時間熟成した。30℃に冷却後10%シュウ酸水溶液で触媒を中和した後、減圧脱水し、POE(5)POP(5)POE(3)メチルエーテルイソステアレートを得た。これを試料番号1とした。
(Production of nonionic surfactant of general formula (1))
[Example 1]
(Production of POE (5) POP (5) POE (3) methyl ether isostearate)
950 g of Hymor TM (manufactured by Toho Chemical Co., Ltd., polyoxyethylene (3) methyl ether) and 7.8 g of KOH were charged into a 5 L autoclave and sufficiently purged with nitrogen, and then alcoholated at 100 to 110 ° C. under reduced pressure. After that, the temperature was raised to 120 to 130 ° C., and 1683 g of propylene oxide was added dropwise over 4 hours in a sealed state, and aging was carried out until there was no pressure change. Subsequently, the temperature was raised to 160 to 170 ° C., and 1274 g of ethylene oxide was added dropwise over 2 hours, followed by aging until the pressure change disappeared. After cooling to 60 ° C. or lower, the catalyst was neutralized with a 10% oxalic acid aqueous solution and then dehydrated under reduced pressure to obtain POE (5) POP (5) POP (3) methyl ether. 3500 g of this content, 1430 g of isostearic acid, and 12 g of potassium carbonate were charged in a 5 L flask and sufficiently purged with nitrogen, then heated to 200-210 ° C. and aged for 10 hours. After cooling to 30 ° C., the catalyst was neutralized with a 10% oxalic acid aqueous solution and then dehydrated under reduced pressure to obtain POE (5) POP (5) POE (3) methyl ether isostearate. This was designated as sample number 1.

[実施例2]
(POE(5)POP(5)POE(3)メチルエーテルオレートの製造)
実施例1と同様にPOE(5)POP(5)POP(3)メチルエーテルを得た。この内容物3500gとオレイン酸1390g、炭酸カリウム12gを5Lフラスコを仕込み十分に窒素置換をした後、200〜210℃まで昇温し、10時間熟成した。30℃に冷却後10%シュウ酸水溶液で触媒を中和した後、減圧脱水し、POE(5)POP(5)POE(3)メチルエーテルオレートを得た。これを試料番号2とした。
[Example 2]
(Production of POE (5) POP (5) POE (3) methyl ether oleate)
POE (5) POP (5) POP (3) methyl ether was obtained in the same manner as in Example 1. After 3500 g of this content, 1390 g of oleic acid, and 12 g of potassium carbonate were charged into a 5 L flask and sufficiently purged with nitrogen, the temperature was raised to 200 to 210 ° C. and aged for 10 hours. After cooling to 30 ° C., the catalyst was neutralized with a 10% oxalic acid aqueous solution and then dehydrated under reduced pressure to obtain POE (5) POP (5) POE (3) methyl ether oleate. This was designated as sample number 2.

[実施例3]
(POE(9)POP(8)POE(3)メチルエーテルイソステアレートの製造)
5LオートクレーブにハイモールTM
700gとKOH8.7gを仕込み十分に窒素置換をした後、減圧下100〜110℃でアルコラート化を行った後、120〜130℃に昇温し密閉下でプロピレンオキサイド1984gを4時間かけて滴下し、圧変化が無くなるまで熟成した。続けて160〜170℃に昇温し、エチレンオキサイド1690gを2時間かけて滴下し圧変化が無くなるまで熟成した。60℃以下まで冷却した後、10%シュウ酸水溶液で触媒を中和した後、減圧脱水しPOE(9)POP(8)POP(3)メチルエーテルを得た。この内容物3500gとイソステアリン酸940g、炭酸カリウム11gを5Lフラスコを仕込み十分に窒素置換をした後、200〜210℃まで昇温し、10時間熟成した。30℃に冷却後10%シュウ酸水溶液で触媒を中和した後、減圧脱水し、POE(9)POP(8)POE(3)メチルエーテルイソステアレートを得た。これを試料番号3とした。
[Example 3]
(Production of POE (9) POP (8) POE (3) methyl ether isostearate)
High Mall TM in 5L autoclave
After 700 g and 8.7 g of KOH were charged and sufficiently purged with nitrogen, alcoholate was performed at 100 to 110 ° C. under reduced pressure, and then the temperature was raised to 120 to 130 ° C. and 1984 g of propylene oxide was added dropwise over 4 hours in a sealed state. Aged until pressure change disappeared. Subsequently, the temperature was raised to 160 to 170 ° C., and 1690 g of ethylene oxide was added dropwise over 2 hours, and the mixture was aged until there was no change in pressure. After cooling to 60 ° C. or lower, the catalyst was neutralized with a 10% oxalic acid aqueous solution and then dehydrated under reduced pressure to obtain POE (9) POP (8) POP (3) methyl ether. 3500 g of this content, 940 g of isostearic acid, and 11 g of potassium carbonate were charged in a 5 L flask and sufficiently purged with nitrogen, then heated to 200-210 ° C. and aged for 10 hours. After cooling to 30 ° C., the catalyst was neutralized with a 10% oxalic acid aqueous solution and then dehydrated under reduced pressure to obtain POE (9) POP (8) POE (3) methyl ether isostearate. This was designated as sample number 3.

[比較例1]
(POE(5)POP(5)POE(3)オクチルドデシルエーテルの製造)
実施例1と同様に、1Lオートクレーブにイソホール20(SASOL社製、オクチルドデシルアルコール)229gとKOH1.4gを仕込み十分に窒素置換をした後、減圧下100〜110℃で1時間アルコラート化を行った。160〜170℃に昇温し密閉下でエチレンオキサイド16gを2時間かけて滴下し、圧変化が無くなるまで熟成した。続けて120〜130℃に冷却し、プロピレンオキサイド213gを4時間かけて滴下し圧変化が無くなるまで熟成した。更に160〜170℃に昇温しエチレンオキサイド97gを1時間かけて滴下し圧変化が無くなるまで熟成した。60℃以下まで冷却した後、10%シュウ酸水溶液で触媒を中和した後、減圧脱水しPOE(5)POP(5)POP(3)オクチルドデシルエーテルを得た。これを比較品1とした。
[Comparative Example 1]
(Production of POE (5) POP (5) POE (3) octyldodecyl ether)
In the same manner as in Example 1, 229 g of isophor 20 (octyldodecyl alcohol, manufactured by SASOL Co., Ltd.) and 1.4 g of KOH were charged into a 1 L autoclave and sufficiently purged with nitrogen. . The temperature was raised to 160 to 170 ° C., and 16 g of ethylene oxide was added dropwise over 2 hours in a sealed state, and aging was performed until there was no pressure change. Subsequently, the mixture was cooled to 120 to 130 ° C., and 213 g of propylene oxide was added dropwise over 4 hours, and the mixture was aged until there was no change in pressure. The temperature was further raised to 160 to 170 ° C., and 97 g of ethylene oxide was added dropwise over 1 hour, and aging was carried out until the pressure change disappeared. After cooling to 60 ° C. or lower, the catalyst was neutralized with a 10% oxalic acid aqueous solution and then dehydrated under reduced pressure to obtain POE (5) POP (5) POP (3) octyldodecyl ether. This was designated as comparative product 1.

[比較例2]
(POE(8)オクチルドデシルエーテルの製造)
1Lオートクレーブにイソホール20(SASOL社製、オクチルドデシルアルコール)229gとKOH1.4gを仕込み十分に窒素置換をした後、減圧下100〜110℃で1時間アルコラート化を行った。160〜170℃に昇温し密閉下でエチレンオキサイド258gを4時間かけて滴下し、圧変化が無くなるまで熟成した。60℃以下まで冷却した後、10%シュウ酸水溶液で触媒を中和した後、減圧脱水しPOE(8)オクチルドデシルエーテルを得た。これを比較品2とした。
[Comparative Example 2]
(Production of POE (8) octyldodecyl ether)
Into a 1 L autoclave, 229 g of isophor 20 (manufactured by SASOL, octyldodecyl alcohol) and 1.4 g of KOH were charged and sufficiently purged with nitrogen, and then alcoholated at 100 to 110 ° C. for 1 hour under reduced pressure. The temperature was raised to 160 to 170 ° C., and 258 g of ethylene oxide was added dropwise over a period of 4 hours in a sealed state, and aging was performed until there was no pressure change. After cooling to 60 ° C. or lower, the catalyst was neutralized with a 10% oxalic acid aqueous solution and then dehydrated under reduced pressure to obtain POE (8) octyldodecyl ether. This was designated as comparative product 2.

[比較例3]
(POE(3)POP(2)POE(3)ラウリルエーテルの製造)
1Lオートクレーブにコノール1275
(新日本理化製、ラウリルアルコール)194gとKOH1.2gを仕込み十分に窒素置換をした後、減圧下100〜110℃で1時間アルコラート化を行った。160〜170℃に昇温し密閉下でエチレンオキサイド132gを2時間かけて滴下し、圧変化が無くなるまで熟成した。続けて120〜130℃に冷却し、プロピレンオキサイド116gを4時間かけて滴下し圧変化が無くなるまで熟成した。更に160〜170℃に昇温しエチレンオキサイド132gを2時間かけて滴下し圧変化が無くなるまで熟成した。60℃以下まで冷却した後、10%シュウ酸水溶液で触媒を中和した後、減圧脱水しPOE(3)POP(2)POE(3)ラウリルエーテルを得た。
[Comparative Example 3]
(Production of POE (3) POP (2) POE (3) lauryl ether)
Conol 1275 in a 1L autoclave
194 g (manufactured by Shin Nippon Rika, lauryl alcohol) and 1.2 g of KOH were charged and sufficiently purged with nitrogen, and then alcoholated at 100 to 110 ° C. under reduced pressure for 1 hour. The temperature was raised to 160 to 170 ° C., and 132 g of ethylene oxide was added dropwise over 2 hours in a sealed state, and aging was carried out until there was no pressure change. Subsequently, the mixture was cooled to 120 to 130 ° C., and 116 g of propylene oxide was added dropwise over 4 hours, and the mixture was aged until there was no change in pressure. The temperature was further raised to 160 to 170 ° C., and 132 g of ethylene oxide was added dropwise over 2 hours, and the mixture was aged until there was no change in pressure. After cooling to 60 ° C. or lower, the catalyst was neutralized with a 10% oxalic acid aqueous solution and then dehydrated under reduced pressure to obtain POE (3) POP (2) POE (3) lauryl ether.

[実施例4]
(洗浄剤組成物としての評価)
表1に示した組成の洗浄剤組成物を通常の方法により製造し、以下の項目について評価した。評価結果についても表1に併せて示した。
a)相溶性;
表1に示した洗浄剤組成物の外観を室温にて目視により以下の判定基準により評価した。この結果を表1に示した。
◎:透明で沈殿なし
○:透明で僅かに沈殿
×:白濁または分離・沈殿
b)安定性(保存安定性)
表1に示した洗浄剤組成物を−10℃及び50℃で2週間放置し、外観を目視により以下の判定基準により評価した。この結果を表1に示した。
◎:透明で沈殿なし
○:透明で僅かに沈殿
×:白濁または分離・沈殿
c)官能評価
表1に示した洗浄剤組成物を、女性パネル10名を対象とし使用感に関する官能評価を行った。「メイク汚れとのなじみ易さ」、「マッサージ感」、「洗浄後のすすぎ易さ」、「洗い上がりのサッパリ感」の評価項目について、「非常に良い:5点」、「良い:4点」、「普通:3点」、「悪い:2点」、「非常に悪い:1点」と評価し、平均点を算出し以下の判定基準により評価した。
◎:5〜4点
○:4〜3点
×:3点未満
[Example 4]
(Evaluation as a cleaning composition)
A cleaning composition having the composition shown in Table 1 was produced by an ordinary method, and the following items were evaluated. The evaluation results are also shown in Table 1.
a) compatibility;
The appearance of the cleaning composition shown in Table 1 was evaluated visually at room temperature according to the following criteria. The results are shown in Table 1.
◎: Transparent and no precipitation ○: Transparent and slight precipitation ×: White turbidity or separation / precipitation b) Stability (storage stability)
The cleaning composition shown in Table 1 was allowed to stand at −10 ° C. and 50 ° C. for 2 weeks, and the appearance was visually evaluated according to the following criteria. The results are shown in Table 1.
◎: Transparent and free of precipitation ○: Transparent and slightly precipitated ×: White turbidity or separation / precipitation c) Sensory evaluation The sensory evaluation of the cleaning composition shown in Table 1 was performed on 10 female panels for use feeling. . Regarding the evaluation items of “Ease of familiarity with makeup stains”, “Massage feeling”, “Ease of rinsing after washing”, and “Feeling fresh after washing”, “Very good: 5 points”, “Good: 4 points” ”,“ Ordinary: 3 points ”,“ bad: 2 points ”,“ very bad: 1 point ”, an average score was calculated and evaluated according to the following criteria.
◎: 5-4 points ○: 4-3 points ×: Less than 3 points

Figure 2008031118
Figure 2008031118

表1の結果から、本発明品の1〜3を配合した洗浄剤組成物は、保存安定性、とりわけ低温での安定性に優れており、その官能評価も良好であることが確認された。
From the results of Table 1, it was confirmed that the detergent composition containing 1-3 of the product of the present invention was excellent in storage stability, in particular, stability at low temperatures, and its sensory evaluation was also good.

Claims (4)

下記一般式(1)で表される非イオン界面活性剤を含むことを特徴とするメイククレンジング用洗浄剤組成物。
O-(EO)-(AO)-(EO)-R (1)
:炭素数8〜22の直鎖または分岐鎖状の飽和または不飽和脂肪酸残基
:炭素数1〜4の直鎖または分岐鎖状の短鎖アルキル基
EO:エチレンオキサイド単位
AO:炭素数3以上のアルキレンオキサイド単位
x:1以上の整数
y:2〜10の整数
z:1以上の整数
A cleansing composition for makeup cleansing, comprising a nonionic surfactant represented by the following general formula (1).
R 1 O- (EO) x - (AO) y - (EO) z -R 2 (1)
R 1 : linear or branched saturated or unsaturated fatty acid residue having 8 to 22 carbon atoms R 2 : linear or branched short chain alkyl group having 1 to 4 carbon atoms EO: ethylene oxide unit AO: Alkylene oxide unit having 3 or more carbon atoms x: integer of 1 or more y: integer of 2 to 10 z: integer of 1 or more
前記非イオン界面活性剤が常温で液状のものであることを特徴とする請求項1記載のメイククレンジング用洗浄剤組成物。 The cleaning composition for makeup cleansing according to claim 1, wherein the nonionic surfactant is liquid at room temperature. 前記非イオン界面活性剤の脂肪酸残基がイソステアリン酸、オレイン酸由来のものであることを特徴とする請求項1又は2記載のメイククレンジング用洗浄剤組成物。 The detergent composition for makeup cleansing according to claim 1 or 2, wherein the fatty acid residue of the nonionic surfactant is derived from isostearic acid or oleic acid. 更に炭化水素油、エステル油、シリコン油、植物油から選ばれる1種以上の常温で液体の油を含むことを特徴とする請求項1〜3のいずれか1項に記載のメイククレンジング用洗浄剤組成物。
The cleaning composition for makeup cleansing according to any one of claims 1 to 3, further comprising one or more kinds of liquid oil at normal temperature selected from hydrocarbon oil, ester oil, silicon oil, and vegetable oil. object.
JP2006208321A 2006-07-31 2006-07-31 Cleansing agent composition for makeup cleansing Pending JP2008031118A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20130131363A1 (en) * 2008-05-23 2013-05-23 Lion Corporation Surfactant Composition for Agricultural Chemicals

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JPH11116522A (en) * 1997-10-07 1999-04-27 Kao Corp New ether compound, antifoaming agent and low-frothing detergent composition
JPH11148091A (en) * 1997-11-14 1999-06-02 Kao Corp Detergent composition
JP2000096097A (en) * 1998-09-22 2000-04-04 Kao Corp Aqueous liquid cleanser
JP2001356307A (en) * 2000-06-14 2001-12-26 Menicon Co Ltd Liquid for contact lenses
JP2003221310A (en) * 2001-11-21 2003-08-05 Shiseido Co Ltd Skin cleanser
JP2004292381A (en) * 2003-03-27 2004-10-21 Shiseido Co Ltd Cleanser

Patent Citations (6)

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Publication number Priority date Publication date Assignee Title
JPH11116522A (en) * 1997-10-07 1999-04-27 Kao Corp New ether compound, antifoaming agent and low-frothing detergent composition
JPH11148091A (en) * 1997-11-14 1999-06-02 Kao Corp Detergent composition
JP2000096097A (en) * 1998-09-22 2000-04-04 Kao Corp Aqueous liquid cleanser
JP2001356307A (en) * 2000-06-14 2001-12-26 Menicon Co Ltd Liquid for contact lenses
JP2003221310A (en) * 2001-11-21 2003-08-05 Shiseido Co Ltd Skin cleanser
JP2004292381A (en) * 2003-03-27 2004-10-21 Shiseido Co Ltd Cleanser

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20130131363A1 (en) * 2008-05-23 2013-05-23 Lion Corporation Surfactant Composition for Agricultural Chemicals
US8969604B2 (en) * 2008-05-23 2015-03-03 Lion Corporation Surfactant composition for agricultural chemicals

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