JP3910094B2 - Topical skin preparation - Google Patents
Topical skin preparation Download PDFInfo
- Publication number
- JP3910094B2 JP3910094B2 JP2002103466A JP2002103466A JP3910094B2 JP 3910094 B2 JP3910094 B2 JP 3910094B2 JP 2002103466 A JP2002103466 A JP 2002103466A JP 2002103466 A JP2002103466 A JP 2002103466A JP 3910094 B2 JP3910094 B2 JP 3910094B2
- Authority
- JP
- Japan
- Prior art keywords
- skin
- external preparation
- group
- general formula
- 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.)
- Expired - Fee Related
Links
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- Cosmetics (AREA)
Description
【０００１】
【発明の属する技術分野】
本発明は、化粧料などに有用な皮膚外用剤に関する。
【０００２】
【従来の技術】
皮膚外用剤において、界面活性剤は可溶化、乳化或いは分散を目的として広く使用されている。中でも、非イオン界面活性剤、特に親水性の非イオン界面活性剤は、肌への刺激が少ないため、化粧水、乳液、クリームなどの化粧料に汎用されている。この様な親水性の非イオン界面活性剤としては、脂肪酸、高級アルコール、水素添加されていても良いひまし油或いは脂肪酸モノグリセライドにエチレンオキサイドを付加重合させた、ポリオキシエチレン基を有するものが最もポピュラーなものとして知られている。確かに、この様な非イオン界面活性剤は一般的には皮膚に対しては刺激が少なく、マイルドなものであるが、有効成分として、美白剤として知られるレゾルシノール誘導体などを含有する場合には、時として敏感肌などの人において、刺激を発現する場合があり、この様な散発する刺激発現への対応が求められている。
【０００３】
特に、レゾルシノール誘導体は美白作用を有するので、これを美白の目的で使用するシチュエーションとしては、日焼け後など、炎症が残っている状態が想定される。この意味でもレゾルシノール誘導体を含有した刺激性の少ない皮膚外用剤の開発が望まれている。
【０００４】
【発明が解決しようとする課題】
本発明は、この様な状況下為されたものであり、レゾルシノール誘導体を含有する皮膚外用剤において、刺激性の少ない皮膚外用剤を提供することを課題とする。
【０００５】
【課題を解決するための手段】
本発明者らは、美白剤を含有する皮膚外用剤において、刺激の少ない皮膚外用剤を求めて鋭意研究努力を重ねた結果、美白剤としてのレゾシノール誘導体と共に含有する非イオン界面活性剤として、特定の化合物を用いることにより、刺激を少なくできるという特性が発揮できることを見出し、発明を完成させるに至った。
即ち、本発明は、以下に示す技術に関するものである。
（１）レゾルシノール誘導体と下記一般式（Ｉ）で表される化合物より選択される１種又は２種以上の非イオン界面活性剤とを含有する皮膚外用剤。
【０００６】
【化３】
（式中、Ｒは炭素数１２〜２２のアルキル基又はアルケニル基を示し、ｎは０又は１を示し、ｑは１〜３の整数を示し、ｑ＝１のときＲ1は一般式（II）で表される基又は糖残基であり、ｑ＝２又は３のときＲ1は糖残基を示す。）
【０００８】
【化４】
（式中、Ｒ2は独立に水素原子又は炭素数１２〜２２の脂肪族アシル基を示し、ｍ、ｐはそれぞれ独立に０〜４０の整数を示し、且つ、ｍ＋ｐの値は少なくとも５であるものとする。）
（２）前記レゾルシノール誘導体は、４−ブチルレゾルシノール及び／又はそれらの生理的に許容される塩である（１）の皮膚外用剤。
（３）前記一般式（Ｉ）で表される化合物は、ポリグリセリンモノ脂肪酸エステル、ポリオキシブテンポリグリセリンアルキルエーテル及びショ糖脂肪酸エステルからなる群より選択される１種又は２種以上である（１）又は（２）の皮膚外用剤。
（４）ポリエチレンオキサイド骨格を有する非イオン界面活性剤を含有していないことを特徴とする（１）〜（３）の何れかの皮膚外用剤。
（５）化粧料であることを特徴とする（１）〜（４）の何れかの皮膚外用剤。
【００１０】
【発明の実施の形態】
以下、本発明について詳細に説明する。
【００１１】
＜１＞本発明の皮膚外用剤に用いられるレゾルシノール誘導体
本発明の皮膚外用剤は、レゾルシノール誘導体を必須成分として含有する。本発明の皮膚外用剤に用いられるレゾルシノール誘導体としては、例えば、４−メチルレゾルシノール、４−エチルレゾルシノール、４−プロピルレゾルシノール、４−（１−メチルエチル）レゾルシノール、４−ブチルレゾルシノール、４−（２−メチルプロピル）レゾルシノール、４−（１−メチルエチルレゾルシノール）、４−ターシャリーブチルレゾルシノールなどのアルキルレゾルシノール及び生理的に許容されるそれらの塩が好ましく例示できる。
【００１２】
これらの中で特に好ましいものは、４−ブチルレゾルシノール及び／又は生理的に許容されるその塩である。これは、４−ブチルレゾルシノール及び生理的に許容されるその塩がレゾルシノール誘導体の中でも優れた美白作用及び抗菌作用などの優れた生理活性を有するからである。
【００１３】
生理的に許容される塩としては、例えば、ナトリウム塩、カリウム塩等のアルカリ金属塩；カルシウム塩、マグネシウム塩等のアルカリ土類金属塩；アンモニウム塩；トリエチルアミン塩、トリエタノールアミン塩等の有機アミン塩；リジン塩、アルギニン塩等の塩基性アミノ酸塩；等が好ましく例示できる。これらは唯一種を含有することもできるし、二種以上を組み合わせて含有することもできる。
【００１４】
上記に例示したレゾルシノール誘導体は何れも既知物質であり、その製造方法は既に知られている。本発明に好適に用いられるアルキルレゾルシノールの製法は、例えば、特開平２−４９７１５号公報等に記載されているので、これらを参照することも可能である。
具体的にアルキルレゾルシノールは以下のように製造することができる。例えば、飽和のカルボン酸とレゾルシノールを塩化亜鉛の存在下で縮合させた後、該縮合物を亜鉛アマルガム／塩酸で還元する方法（Lille.J.Bitter, LA. Peiner. V, Tr. Nauch - Iasled. Inst.slantsev 1969,No 18, 127参照)、または、レゾルシノールと対応するアルキルアルコールとをアルミナ触媒を使用して２００〜４００℃の高温下で反応させる方法（英国特許第１，５８１，４２８号明細書参照）等によって容易に得ることができる。
【００１５】
上記に例示したレゾルシノール誘導体には市販されているものもあるので、市販品を利用することもできる。例えば、４−ブチルレゾルシノールとしては、「ルシノール」（株式会社クラレ製）が特に好ましい市販品として例示することができる。
これらのレゾルシノール誘導体の好ましい含有量は、皮膚外用剤全量に対して、総量で０．０１〜６重量％であり、更に好ましくは、０．０５〜４重量％である。レゾルシノール誘導体の含有量が少なすぎると効果を発揮しない場合があり、多すぎても効果が頭打ちになり、却って処方の自由度を阻害してしまう場合がある。
【００１６】
＜２＞本発明の皮膚外用剤に用いる上記一般式（Ｉ）で表される化合物
本発明の皮膚外用剤は、上記一般式（Ｉ）で表される化合物を非イオン界面活性剤として含有することを特徴とする。
上記一般式（Ｉ）中、Ｒは炭素数１２〜２２のアルキル基又はアルケニル基を示し、ｎは０又は１を示し、ｑは１〜３の整数を示し、ｑ＝１のときＲ1は一般式（II）で表される基又は糖残基であり、ｑ＝２又は３のときＲ1は糖残基を示す。炭素数１２〜２２のアルキル基又はアルケニル基としては、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、リノリル基等が好ましい。
上記一般式（II）中、Ｒ2は独立に水素原子又は炭素数１２〜２２の脂肪族アシル基を示し、ｍ、ｐはそれぞれ独立に、０〜４０の整数を表し、且つｍ＋ｐの値は少なくとも５である。ｍは好ましくは５〜２０の整数であり、ｐは５〜２０の整数である。
糖残基としては、ショ糖、マルトース等が挙げられる。
【００１７】
上記一般式（Ｉ）に表される化合物として具体的には、ポリグリセリン脂肪酸エステル、ポリオキシブテンポリグリセリンアルキルエーテル或いはショ糖脂肪酸エステル等が好ましく例示できる。
【００１８】
ポリグリセリン脂肪酸エステルのポリグリセリンの部分としては、グリセリンの５〜２０量体が好ましく例示でき、脂肪酸部分としては、ラウリン酸、ミリスチン酸、パルミチン酸、ステアリン酸、オレイン酸、リノール酸或いはベヘン酸等が好ましく例示できる。即ち、一般式（Ｉ）において、ｎ＝１であり、ｑ＝１であり、Ｒ1で示される基は、ｍ＝５〜２０、ｐ＝０の一般式（II）であり、Ｒで示されるアルキル基又はアルケニル基は、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、リノリル基等が好ましい。エステル化度は１分子あたり平均１〜３で、且つフリーの水酸基を少なくとも３個有する形態が好ましい。即ち、一般式（Ｉ）で示されるポリグリセリン脂肪酸エステルにおいて、Ｒ1は一般式（II）で示される基（式中、ｍ＝５〜２０、ｐ＝０のポリグリセリン部分）であり、ポリグリセリン部分のＲ2の１〜３個が炭素数１２〜２２の脂肪族アシル基を示し、少なくとも３個が水素である。
なお、Ｒ2の炭素数１２〜２２の脂肪族アシル基としては、ライロイル基、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、リノロイル基等が好ましい。
【００１９】
この様なポリグリセリン脂肪酸エステルの多くが市販されており、特に好ましいものとしては、デカグリセリンモノラウレート、デカグリセリンモノオレート、デカグリセリンモノステアレート等が市販品では好ましく例示できる。
【００２０】
ポリオキシブテンポリグリセリンアルキルエーテルとしては、オキシブチレン基の付加モル数（平均重合度）が平均で１０〜２０が好ましく、ポリグリセリンの平均付加モル数（平均重合度）が１０〜２０のものが好ましい。即ち、一般式（Ｉ）において、ｎ＝０であり、ｑ＝１であり、Ｒ1で示される基は、ｍ＝１０〜２０、ｐ＝１０〜２０の一般式（II）であり、Ｒで示されるアルキル基又はアルケニル基としては、ステアリル基、オレイル基が好ましい。
【００２１】
上記ポリオキシブテンポリグリセリンアルキルエーテルは、市販されているものもあり、それを利用することもできる。市販品で特に好ましいものは、ポリオキシブテン（１３）ポリグリセリル（１４）ステアリルエーテル（ハイグリオールＳ−２６；日本サーファクタント株式会社製）等が挙げられる。
【００２２】
ショ糖脂肪酸エステルとしては、ｎ＝１且つｑ＝１のショ糖モノ脂肪酸エステル、ｑ＝２のショ糖ジ脂肪酸エステル、ｑ＝３のショ糖トリ脂肪酸エステルが好ましく挙げられるが、中でもショ糖モノ脂肪酸エステルがより好ましく、脂肪酸部分としては、ラウリン酸、パルミチン酸、ステアリン酸、オレイン酸が好ましく例示できる。即ち、一般式（Ｉ）のＲ1で示される基は、糖残基としてのショ糖であり、Ｒで示されるアルキル基又はアルケニル基は、ラウリル基、ミリスチル基、パルミチル基、ステアリル基、オレイル基等が好ましい。
具体的に好ましいショ糖モノ脂肪酸エステルとしては、ショ糖モノラウレートが特に好ましい。
【００２３】
本発明の皮膚外用剤は、上記一般式（Ｉ）に表される化合物を、唯一種のみ含有させることもできるし、二種以上を組み合わせて含有させることもできる。これらの化合物の好ましい含有量は、総量で皮膚外用剤全量に対して、含有量０．０１〜５重量％であり、更に好ましくは０．０５〜３重量％である。少なすぎると、界面活性剤としての基本的機能である可溶化、乳化、分散作用を発現しない場合があり、多すぎると系を損なう場合がある。
【００２４】
＜３＞本発明の皮膚外用剤
本発明の皮膚外用剤は、上記レゾルシノール誘導体及び上記一般式（Ｉ）で表される化合物より選択される１種又は２種以上の非イオン界面活性剤を含有することを特徴とする。
本発明でいう、「皮膚外用剤」とは、皮膚に外用で投与する組成物の総称であり、化粧料、皮膚外用医薬組成物、皮膚外用消毒剤などが好ましく例示できる。これらの内、特に好ましいものは化粧料であり、中でも美白を目的とする化粧料が特に好ましい。これは、本発明の必須成分であるレゾルシノール誘導体の効果を遺憾なく発揮するためである。
【００２５】
本発明の皮膚外用剤は、レゾルシノール誘導体と一般式（Ｉ）に表される化合物との組み合わせによって、著しく刺激感が抑制されているため、今まで、刺激感のために美白化粧料を使用できなかった肌の弱い人、敏感肌の人も使用することができる。日焼け後の炎症の残る肌に、光によるメラニン産生を抑制する目的で投与することも、この特性より可能となる。また、レゾルシノール誘導体の多くは抗菌作用を有しているため、刺激を発現することがあるパラベン類などの防腐剤を皮膚外用剤に含有させなくとも、優れた対微生物特性を有する。この意味でも敏感肌の人に取って有用な皮膚外用剤であるといえる。
【００２６】
本発明の皮膚外用剤は、上記レゾルシノール誘導体及び上記一般式（Ｉ）で表される化合物以外に、通常、皮膚外用剤で使用される任意成分を含有することができる。この様な任意成分としては、例えば、ワセリン、マイクロクリスタリンワックス等のような炭化水素類；ホホバ油、セチルイソオクタネート等のエステル類；オリーブ油等のトリグリセライド類；オクタデシルアルコール、オレイルアルコール等の高級アルコール類；グリセリン、１，３−ブタンジオール、１，２−ペンタンジオール、イソプレングリコール、ジプロピレングリコール等の多価アルコール類；非イオン界面活性剤；アニオン界面活性剤；カチオン界面活性剤；両性界面活性剤；エタノール；カーボポール等の増粘剤；防腐剤；紫外線吸収剤；抗酸化剤類等が例示できる。
【００２７】
本発明の皮膚外用剤の特に好ましい形態は、ポリエチレンオキサイド骨格を有する非イオン界面活性剤、即ち、ポリエチレングリコールやポリオキシエチレンが付加した非界面活性剤を含有しない形態である。これは後記の実施例に示すように、これらの成分とレゾルシノール誘導体の組み合わせで、損傷肌などにおいて、刺激感が出やすくなるからである。
【００２８】
ポリエチレンオキサイド骨格を有する非イオン界面活性剤を含まず、上記一般式（Ｉ）で表される化合物を非イオン界面活性剤として含む本発明の皮膚外用剤は、上述のように優れた刺激発現抑制作用があるので、従来のように刺激発現抑制する目的で、美白剤としてプラセンターを用いたり、保湿剤としてコラーゲン類を用いるなどの哺乳類偶蹄目の動物を起源とする原料を用いずとも剤形化できる。
本発明の皮膚外用剤は、レゾルシノール誘導体と上記一般式（Ｉ）で表される化合物の必須成分と任意成分とを常法に従って処理することにより製造することができる。
【００２９】
【実施例】
以下、本発明を具体的に説明するが、本発明はかかる実施例にのみに限定されないことは言うまでもない。
【００３０】
＜実施例１＞
以下に示す処方に従って、本発明の皮膚外用剤である化粧水を作成した。即ち、処方成分を８０℃で加熱可溶化して、攪拌冷却して化粧料１を得た。
・水 ９０．３５重量部
・１，３−ブタンジオール ５重量部
・１，２−ペンタンジオール ０．５重量部
・デカグリセリンモノオレート １重量部
・リン酸水素ナトリウム ０．１５重量部
・４−ブチルレゾルシノールナトリウム塩 ３重量部
【００３１】
＜対照例１＞
実施例１の化粧料１のデカグリセリンモノオレートの代わりに水を用いて、実施例１と同様に化粧料２を作成した。
【００３２】
＜比較例１＞
実施例１の化粧料１のデカグリセリンモノオレートの代わりにポリオキシエチレン（５０）硬化ヒマシ油を用いて、実施例１と同様に化粧料３を作成した。
【００３３】
＜対照例２＞
実施例１の化粧料１の４−ブチルレゾルシノールナトリウム塩の代わりに水を用いて、実施例１と同様に化粧料４を作成した。
【００３４】
（化粧料の評価）
上記で得られた化粧料１〜４について、刺激感を評価した。敏感肌であると自認しているパネラー４０人に対して使用テストを行った。パネラーは偏りがないように１群１０名、４群に分け、化粧料１使用群、化粧料２使用群、化粧料３使用群、化粧料４使用群とした。各パネラーは被験サンプルを朝晩２回、２週連日塗布し、最終日の２４時間後に使用感を評価してもらった。このテスト期間中に、化粧料使用に際して少しでも刺激感を感じた場合には、直ちにテストを中止してもらい脱落例とした。使用感の評価は、非常によい（スコア５）、良い（スコア４）、やや良い（スコア３）、やや悪い（スコア２）、悪い（スコア１）の５段階の基準にあわせて行った。結果を出現例数として、表１に示す。これより、本発明の皮膚外用剤である化粧料は、刺激感抑制作用に優れることが判る。
【００３５】
【表１】
＜実施例２〜６＞
化粧料１の４−ブチルレゾルシノールナトリウム塩を表２に示す他のレゾルシノール誘導体に代えて、本発明の皮膚外用剤である化粧料５〜９を作成した。このものの刺激感の発現性を、美白剤に刺激感を感じやすいパネラーに対して評価した。評価基準は、化粧料１と比べて同程度又はそれ以上の刺激感の低さを○、化粧料１より、やや刺激感を感じやすい場合は△、化粧料１より明らかに刺激感を感じやすい場合には×とした。結果を表２に示す。これより、レゾルシノール誘導体の種類に係わらず、本発明の化粧料は優れた刺激感の抑制作用を示すことが判る。
【００３７】
【表２】
＜実施例７〜１０＞
化粧料１の非イオン界面活性剤として用いたデカグリセリンモノオレートを表３に示す化合物に代えて、本発明の皮膚外用剤である化粧料１０〜１３を作成し、実施例２〜６と同様に評価した。結果を表３に示す。これより、本発明の皮膚外用剤は、非イオン界面活性剤として一般式（Ｉ）で表される化合物を用いれば、好適であることが判る。
【００３９】
【表３】
＜実施例１１＞
以下に示す処方に従って、本発明の皮膚外用剤である化粧料を作成した。即ち、処方成分を８０℃で加熱可溶化して、攪拌冷却して化粧料１４を得た。このものは実施例１より更に刺激発現性が少なかった。
・水 ９０．３５重量部
・１，３−ブタンジオール ５重量部
・１，２−ペンタンジオール ０．５重量部
・デカグリセリンモノオレート ０．５重量部
・ショ糖モノラウレート ０．５重量部
・リン酸水素ナトリウム ０．１５重量部
・４−ブチルレゾルシノールナトリウム塩 ３重量部
【００４１】
【発明の効果】
本発明によれば、レゾルシノール誘導体を含有する皮膚外用剤において、刺激性の少ない皮膚外用剤を提供することができる。[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a skin external preparation useful for cosmetics and the like.
[0002]
[Prior art]
In external preparations for skin, surfactants are widely used for the purpose of solubilization, emulsification or dispersion. Among these, nonionic surfactants, particularly hydrophilic nonionic surfactants, are widely used in cosmetics such as skin lotions, emulsions, and creams because they are less irritating to the skin. As such hydrophilic nonionic surfactants, those having a polyoxyethylene group obtained by addition polymerization of ethylene oxide to fatty acid, higher alcohol, hydrogenated castor oil or fatty acid monoglyceride are most popular. Known as a thing. Certainly, such nonionic surfactants are generally mild and mild to the skin, but if they contain resorcinol derivatives known as whitening agents as active ingredients, In some cases, a person with sensitive skin may develop a stimulus, and a response to such sporadic stimulus is required.
[0003]
In particular, since the resorcinol derivative has a whitening effect, a situation in which inflammation remains, such as after sunburn, is assumed as a situation where this is used for the purpose of whitening. In this sense, it is desired to develop an external preparation for skin with less irritation containing a resorcinol derivative.
[0004]
[Problems to be solved by the invention]
The present invention has been made under such circumstances, and an object of the present invention is to provide a skin external preparation with less irritation in a skin external preparation containing a resorcinol derivative.
[0005]
[Means for Solving the Problems]
As a result of intensive research efforts for skin external preparations with less irritation in skin external preparations containing whitening agents, the present inventors have identified as a nonionic surfactant to be contained together with a resorcinol derivative as a whitening agent. It has been found that the use of this compound can exhibit the property of reducing irritation and has led to the completion of the invention.
That is, this invention relates to the technique shown below.
(1) A skin external preparation containing a resorcinol derivative and one or more nonionic surfactants selected from compounds represented by the following general formula (I).
[0006]
[Chemical 3]
(In the formula, R represents an alkyl group or alkenyl group having 12 to 22 carbon atoms, n represents 0 or 1, q represents an integer of 1 to 3, and when q = 1, R 1 represents the general formula (II And when q = 2 or 3, R 1 represents a sugar residue.)
[0008]
[Formula 4]
(In the formula, R 2 independently represents a hydrogen atom or an aliphatic acyl group having 12 to 22 carbon atoms, m and p each independently represents an integer of 0 to 40, and the value of m + p is at least 5. Suppose)
(2) The external preparation for skin according to (1), wherein the resorcinol derivative is 4-butylresorcinol and / or a physiologically acceptable salt thereof.
(3) The compound represented by the general formula (I) is one or more selected from the group consisting of polyglycerol mono fatty acid ester, polyoxybutene polyglycerol alkyl ether and sucrose fatty acid ester ( The external preparation for skin of 1) or (2).
(4) The external preparation for skin according to any one of (1) to (3), which does not contain a nonionic surfactant having a polyethylene oxide skeleton.
(5) The external preparation for skin according to any one of (1) to (4), which is a cosmetic.
[0010]
DETAILED DESCRIPTION OF THE INVENTION
Hereinafter, the present invention will be described in detail.
[0011]
<1> Resorcinol derivative used in skin external preparation of the present invention The skin external preparation of the present invention contains a resorcinol derivative as an essential component. Examples of the resorcinol derivative used in the external preparation for skin of the present invention include 4-methylresorcinol, 4-ethylresorcinol, 4-propylresorcinol, 4- (1-methylethyl) resorcinol, 4-butylresorcinol, 4- (2 Preferred examples include alkylresorcinols such as -methylpropyl) resorcinol, 4- (1-methylethylresorcinol), 4-tertiarybutylresorcinol and physiologically acceptable salts thereof.
[0012]
Particularly preferred among these are 4-butylresorcinol and / or physiologically acceptable salts thereof. This is because 4-butylresorcinol and physiologically acceptable salts thereof have excellent physiological activities such as excellent whitening action and antibacterial action among resorcinol derivatives.
[0013]
Examples of physiologically acceptable salts include alkali metal salts such as sodium salts and potassium salts; alkaline earth metal salts such as calcium salts and magnesium salts; ammonium salts; organic amines such as triethylamine salts and triethanolamine salts. Preferred examples include salts; basic amino acid salts such as lysine salts and arginine salts; These can contain only the seed | species, and can also contain it in combination of 2 or more type.
[0014]
All of the resorcinol derivatives exemplified above are known substances, and their production methods are already known. The method for producing alkylresorcinol suitably used in the present invention is described in, for example, Japanese Patent Application Laid-Open No. 2-49715, and the like can be referred to.
Specifically, alkylresorcinol can be produced as follows. For example, a method of condensing a saturated carboxylic acid and resorcinol in the presence of zinc chloride and then reducing the condensate with zinc amalgam / hydrochloric acid (Lille. J. Bitter, LA. Peiner. V, Tr. Nauch-Iasled Inst. Slantsev 1969, No 18, 127), or a method of reacting resorcinol with a corresponding alkyl alcohol at a high temperature of 200 to 400 ° C. using an alumina catalyst (British Patent No. 1,581,428) It can be easily obtained by referring to the description).
[0015]
Since some of the resorcinol derivatives exemplified above are commercially available, commercially available products can also be used. For example, as 4-butylresorcinol, “lucinol” (manufactured by Kuraray Co., Ltd.) can be exemplified as a particularly preferable commercial product.
The preferred content of these resorcinol derivatives is 0.01 to 6% by weight, more preferably 0.05 to 4% by weight, based on the total amount of the external preparation for skin. If the content of the resorcinol derivative is too small, the effect may not be exhibited. If the content is too large, the effect reaches a peak, and the degree of freedom of prescription may be hindered.
[0016]
<2> Compound represented by the above general formula (I) used in the skin external preparation of the present invention The skin external preparation of the present invention contains the compound represented by the above general formula (I) as a nonionic surfactant. It is characterized by that.
In the general formula (I), R represents an alkyl group or alkenyl group having 12 to 22 carbon atoms, n represents 0 or 1, q represents an integer of 1 to 3, and when q = 1, R 1 is The group or sugar residue represented by the general formula (II), and when q = 2 or 3, R 1 represents a sugar residue. As the alkyl group or alkenyl group having 12 to 22 carbon atoms, a lauryl group, a myristyl group, a palmityl group, a stearyl group, an oleyl group, a linoleyl group, and the like are preferable.
In the general formula (II), R 2 independently represents a hydrogen atom or an aliphatic acyl group having 12 to 22 carbon atoms, m and p each independently represents an integer of 0 to 40, and the value of m + p is Is at least 5. m is preferably an integer of 5 to 20, and p is an integer of 5 to 20.
Examples of the sugar residue include sucrose and maltose.
[0017]
Specific examples of the compound represented by the general formula (I) include polyglycerin fatty acid ester, polyoxybutene polyglycerin alkyl ether, and sucrose fatty acid ester.
[0018]
As the polyglycerin part of the polyglycerin fatty acid ester, glycerin 5-20 mer can be preferably exemplified, and as the fatty acid part, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, behenic acid, etc. Can be preferably exemplified. That is, in the general formula (I), n = 1, q = 1, and the group represented by R 1 is the general formula (II) in which m = 5 to 20 and p = 0, and represented by R The alkyl group or alkenyl group is preferably a lauryl group, a myristyl group, a palmityl group, a stearyl group, an oleyl group, a linoleyl group, or the like. The degree of esterification is preferably from 1 to 3 on average per molecule and having at least 3 free hydroxyl groups. That is, in the polyglycerol fatty acid ester represented by the general formula (I), R 1 is a group represented by the general formula (II) (wherein m = 5 to 20, p = 0 polyglycerin moiety) 1-3 of R < 2 > of a glycerol part shows a C12-C22 aliphatic acyl group, and at least 3 is hydrogen.
As the aliphatic acyl group having a carbon number of R 2 12 to 22, Rairoiru group, myristoyl group, palmitoyl group, stearoyl group, oleoyl group, a linoleoyl group are preferable.
[0019]
Many of such polyglycerol fatty acid esters are commercially available, and particularly preferable examples include decaglycerol monolaurate, decaglycerol monooleate, and decaglycerol monostearate.
[0020]
As polyoxybutene polyglycerin alkyl ether, the number of added moles of oxybutylene groups (average degree of polymerization) is preferably 10-20 on average, and the number of added moles of polyglycerin (average degree of polymerization) is 10-20. preferable. That is, in general formula (I), n = 0, q = 1, and the group represented by R 1 is general formula (II) where m = 10 to 20 and p = 10 to 20, and R The alkyl group or alkenyl group represented by is preferably a stearyl group or an oleyl group.
[0021]
Some of the polyoxybutene polyglycerin alkyl ethers are commercially available, and can be used. Particularly preferred commercially available products include polyoxybutene (13) polyglyceryl (14) stearyl ether (High Glyol S-26; manufactured by Nippon Surfactant Co., Ltd.).
[0022]
Preferred examples of the sucrose fatty acid ester include sucrose monofatty acid ester with n = 1 and q = 1, sucrose difatty acid ester with q = 2, and sucrose trifatty acid ester with q = 3. Fatty acid esters are more preferred, and preferred examples of the fatty acid moiety include lauric acid, palmitic acid, stearic acid, and oleic acid. That is, the group represented by R 1 in the general formula (I) is sucrose as a sugar residue, and the alkyl group or alkenyl group represented by R is a lauryl group, a myristyl group, a palmityl group, a stearyl group, an oleyl group. Groups and the like are preferred.
As a particularly preferred sucrose monofatty acid ester, sucrose monolaurate is particularly preferred.
[0023]
The skin external preparation of the present invention may contain only one kind of the compound represented by the above general formula (I), or may contain two or more kinds in combination. The total content of these compounds is 0.01 to 5% by weight, more preferably 0.05 to 3% by weight, based on the total amount of the external preparation for skin. If the amount is too small, the solubilizing, emulsifying, and dispersing actions that are basic functions as a surfactant may not be exhibited, and if the amount is too large, the system may be damaged.
[0024]
<3> External preparation for skin of the present invention The external preparation for skin of the present invention contains one or more nonionic surfactants selected from the resorcinol derivative and the compound represented by the general formula (I). It is characterized by doing.
The “skin external preparation” referred to in the present invention is a general term for compositions to be externally administered to the skin, and preferred examples include cosmetics, external skin pharmaceutical compositions, and external skin disinfectants. Of these, cosmetics are particularly preferred, and cosmetics intended for whitening are particularly preferred. This is because the effect of the resorcinol derivative, which is an essential component of the present invention, is fully exhibited.
[0025]
Since the external preparation for skin of the present invention is remarkably suppressed in irritation by the combination of the resorcinol derivative and the compound represented by the general formula (I), whitening cosmetics can be used for irritation until now. It can also be used by people who have weak skin or who have sensitive skin. This property makes it possible to administer to irritated skin after sunburn for the purpose of suppressing melanin production by light. In addition, since many resorcinol derivatives have an antibacterial action, they have excellent microbial properties even if a preservative such as parabens that may cause irritation is not included in the external preparation for skin. In this sense, it can be said that it is a skin external preparation useful for people with sensitive skin.
[0026]
The external preparation for skin of the present invention can contain optional components usually used in external preparations for skin other than the resorcinol derivative and the compound represented by the general formula (I). Examples of such optional components include hydrocarbons such as petroleum jelly and microcrystalline wax; esters such as jojoba oil and cetyl isooctanoate; triglycerides such as olive oil; higher alcohols such as octadecyl alcohol and oleyl alcohol Polyhydric alcohols such as glycerin, 1,3-butanediol, 1,2-pentanediol, isoprene glycol, dipropylene glycol; nonionic surfactant; anionic surfactant; cationic surfactant; amphoteric surfactant Agents; ethanol; thickeners such as carbopol; antiseptics; ultraviolet absorbers; antioxidants.
[0027]
A particularly preferred form of the external preparation for skin of the present invention is a form containing no nonionic surfactant having a polyethylene oxide skeleton, that is, a nonsurfactant added with polyethylene glycol or polyoxyethylene. This is because a combination of these components and a resorcinol derivative makes it easy to produce irritation in damaged skin and the like, as shown in the examples described later.
[0028]
The external preparation for skin of the present invention, which does not contain a nonionic surfactant having a polyethylene oxide skeleton and contains the compound represented by the above general formula (I) as a nonionic surfactant, has excellent suppression of irritation as described above. Because of its action, the dosage form can be used without the use of raw materials originating from mammals of the order of mammals, such as using placenta as a whitening agent or using collagens as a moisturizing agent for the purpose of suppressing stimulus expression as in the past. Can be
The external preparation for skin of the present invention can be produced by treating the resorcinol derivative and the essential and optional components of the compound represented by the general formula (I) according to a conventional method.
[0029]
【Example】
Hereinafter, the present invention will be specifically described, but it is needless to say that the present invention is not limited to such examples.
[0030]
<Example 1>
A skin lotion that is an external preparation for skin according to the present invention was prepared according to the formulation shown below. That is, the prescription ingredients were heat-solubilized at 80 ° C., stirred and cooled, and cosmetic 1 was obtained.
-90.35 parts by weight of water-5 parts by weight of 1,3-butanediol-0.5 parts by weight of 1,2-pentanediol-1 part by weight of decaglycerol monooleate-0.15 parts by weight of sodium hydrogen phosphate-4- Butyl resorcinol sodium salt 3 parts by weight [0031]
<Control Example 1>
A cosmetic 2 was prepared in the same manner as in Example 1 using water instead of decaglycerin monooleate in the cosmetic 1 of Example 1.
[0032]
<Comparative Example 1>
A cosmetic 3 was prepared in the same manner as in Example 1 except that polyoxyethylene (50) hydrogenated castor oil was used instead of the decaglycerin monooleate of the cosmetic 1 in Example 1.
[0033]
<Control Example 2>
A cosmetic 4 was prepared in the same manner as in Example 1 using water instead of the 4-butylresorcinol sodium salt of the cosmetic 1 in Example 1.
[0034]
(Evaluation of cosmetics)
About the cosmetics 1-4 obtained above, irritation | stimulation was evaluated. A use test was conducted on 40 panelists who recognized themselves as sensitive skin. The panelists were divided into 10 people per group and 4 groups so as not to be biased, and were classified into a cosmetic 1 usage group, a cosmetic 2 usage group, a cosmetic 3 usage group, and a cosmetic 4 usage group. Each panelist applied the test sample twice a day in the morning and 2 days a day for 2 weeks, and evaluated the feeling of use 24 hours after the final day. During this test period, when a slight sense of irritation was felt during the use of cosmetics, the test was immediately stopped and dropped out. The evaluation of the feeling of use was performed in accordance with five levels of criteria: very good (score 5), good (score 4), slightly good (score 3), slightly bad (score 2), and bad (score 1). The results are shown in Table 1 as the number of appearance examples. From this, it can be seen that the cosmetic which is the external preparation for skin of the present invention is excellent in the irritation suppression effect.
[0035]
[Table 1]
<Examples 2 to 6>
Cosmetics 5 to 9, which are skin external preparations of the present invention, were prepared by replacing 4-butylresorcinol sodium salt of cosmetic 1 with other resorcinol derivatives shown in Table 2. The expression of the irritation of this product was evaluated against a panelist who easily feels irritation to the whitening agent. Evaluation criteria are the same or more low irritation compared to cosmetic 1, ◯, if slightly more irritating than cosmetic 1, △, apparently more irritating than cosmetic 1 In the case, it was set as x. The results are shown in Table 2. From this, it can be seen that the cosmetic of the present invention exhibits an excellent irritation suppressing effect regardless of the type of resorcinol derivative.
[0037]
[Table 2]
<Examples 7 to 10>
Instead of the decaglycerin monooleate used as the nonionic surfactant of cosmetic 1 in place of the compounds shown in Table 3, cosmetics 10 to 13 which are external preparations for skin of the present invention were prepared, and the same as in Examples 2 to 6 Evaluated. The results are shown in Table 3. From this, it turns out that the skin external preparation of this invention is suitable if the compound represented by general formula (I) is used as a nonionic surfactant.
[0039]
[Table 3]
<Example 11>
According to the formulation shown below, a cosmetic which is an external preparation for skin of the present invention was prepared. That is, the prescription ingredients were heat-solubilized at 80 ° C., stirred and cooled to obtain a cosmetic 14. This product was less irritating than Example 1.
・ Water 90.35 parts ・ 1,3-butanediol 5 parts ・ 1,2-pentanediol 0.5 part ・ Decaglycerin monooleate 0.5 part ・ Sucrose monolaurate 0.5 part -Sodium hydrogen phosphate 0.15 parts by weight-4-Butyl resorcinol sodium salt 3 parts by weight [0041]
【The invention's effect】
ADVANTAGE OF THE INVENTION According to this invention, the skin external preparation with little irritation can be provided in the skin external preparation containing a resorcinol derivative.
Claims (4)
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| JP2002103466A JP3910094B2 (en) | 2002-04-05 | 2002-04-05 | Topical skin preparation |
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| US12090223B2 (en) | 2020-12-14 | 2024-09-17 | The Procter & Gamble Company | Method of manufacturing cosmetic compositions comprising sucrose esters and solvents |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2005179238A (en) * | 2003-12-18 | 2005-07-07 | Kuraray Co Ltd | Skin care preparation |
| JP2006124358A (en) * | 2004-11-01 | 2006-05-18 | Shiseido Co Ltd | 4-alkylresorcinol derivative and bleaching agent containing the same as active ingredient |
| JP2006124357A (en) * | 2004-11-01 | 2006-05-18 | Shiseido Co Ltd | 4-alkylresorcinol derivative and bleaching agent containing the same as active ingredient |
| JP5263940B2 (en) * | 2008-05-29 | 2013-08-14 | 株式会社 資生堂 | Topical skin preparation |
| JP2012513387A (en) * | 2008-12-23 | 2012-06-14 | ガルデルマ・ソシエテ・アノニム | Topical pharmaceutical composition comprising a water-sensitive active ingredient |
| JP5856761B2 (en) * | 2011-06-09 | 2016-02-10 | 昭和電工株式会社 | External preparation for skin and method for producing the same |
| JP6510177B2 (en) | 2014-04-01 | 2019-05-08 | ロレアル | Compositions in the form of nano or microemulsions |
| JP6328979B2 (en) * | 2014-04-04 | 2018-05-23 | ポーラ化成工業株式会社 | Topical skin preparation |
| JP6370590B2 (en) * | 2014-04-24 | 2018-08-08 | ポーラ化成工業株式会社 | Water-in-oil emulsion composition |
| JP6370589B2 (en) * | 2014-04-24 | 2018-08-08 | ポーラ化成工業株式会社 | Oil-in-water emulsion composition |
| JP6537788B2 (en) * | 2014-06-25 | 2019-07-03 | ロレアル | Composition in the form of a nanoemulsion or microemulsion or having a lamellar structure |
| JP6890962B2 (en) | 2016-12-09 | 2021-06-18 | ロレアル | Non-adhesive stable composition |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US12090223B2 (en) | 2020-12-14 | 2024-09-17 | The Procter & Gamble Company | Method of manufacturing cosmetic compositions comprising sucrose esters and solvents |
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