JP4671205B2 - Skin preparation - Google Patents

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JP4671205B2
JP4671205B2 JP30273799A JP30273799A JP4671205B2 JP 4671205 B2 JP4671205 B2 JP 4671205B2 JP 30273799 A JP30273799 A JP 30273799A JP 30273799 A JP30273799 A JP 30273799A JP 4671205 B2 JP4671205 B2 JP 4671205B2
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kojic acid
skin
formula
present
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JP2001122754A (en
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伸介 本多
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Sansho Pharmaceutical Co Ltd
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Sansho Pharmaceutical Co Ltd
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Description

【0001】
【発明の属する技術分野】
本発明は、皮膚外用剤に関するものであって、より詳しくは、コウジ酸および/またはその誘導体と、皮膚親和剤としてシアノアクリレート系化合物および/またはベンゾトリアゾール基含有シリコーン誘導体から選ばれる1種または2種以上を配合することによって、耐水性良好なSPF特性が保持され、同時にコウジ酸類の経皮吸収が促進されることを特徴とする皮膚外用剤に関する。
【0002】
【従来の技術及びその問題点】
コウジ酸およびその誘導体は、特開昭55−157509号公報に開示されているように紫外線吸収効果を有する物質として知られており、その他にも色白効果や消炎効果などの種々な特徴を有することが知られている。その有用性については、例えば、特公昭56−18569号公報、特公昭61−10447号公報、特公昭60−7961号公報、特公昭58−34446号公報、特公昭61−60801号公報、特公昭58−22151号公報、特公昭58−22152号公報、特公昭60−9722号公報、特公昭60−10005号公報、特公昭63−27322号公報、特公平6−13448号公報、特公平6−16685号公報、特開平1−132502号公報、特許2549148号公報、特許2712126号公報、特許2504805号公報、特公平5−30422号公報、特許2977865号公報、特開平10−17468号公報、特開平10−59847号公報および特開平10−212225号公報等に開示された発明によっても窺い知ることができる。
【0003】
この様に、コウジ酸およびその誘導体(以下、これらを総称して単に「コウジ酸類」と呼ぶことがある)は非常に有用な化合物であるが、この化合物は水溶性であるため、耐水性の低い製剤に配合した場合には、塗布後の付着性に限界がある。例えば、コウジ酸類のO/W製剤を塗布した後、塗布面が汗や水に濡れたりした場合には、コウジ酸が汗や水とともに流れ落ちてしまい、コウジ酸の皮膚への残存率が低下するため、コウジ酸の安定な機能性が発揮できないという問題があった。
【0004】
特に、コウジ酸は紫外線吸収剤として利用できることが知られているが、当該機能を期待してコウジ酸を有効成分とするサンスクリーン剤を調製した場合には、サンスクリーン剤の使用特性上、汗や水に濡れる機会が多いため、上述の問題からコウジ酸単独では安定なサンブロック効果が達成できず、さらに、同時に期待される美白効果等の種々の薬効も損なわれていた。
【0005】
また、近年、サンスクリーン剤には皮膚への負担軽減と使用感重視の観点から紫外線吸収剤を高配合しないサンスクリーン効果持続性の高い製剤が消費者から求められており、所望のSPF値が安定に保持できる、とりわけO/W製剤においてもコウジ酸類の機能特性が安定に発揮される製剤の開発は引き続いての課題であった。
【0006】
【発明が解決しようとする課題】
そこで、本発明の目的は、コウジ酸類と皮膚親和剤として、特定のシアノアクリレート系化合物または特定のベンゾトリアゾール基含有シリコーン誘導体から選ばれる1種または2種以上を配合することにより、従来のコウジ酸製剤の持つ上記の問題点を解決することにあり、特に、耐水性良好なSPF特性が保持され、同時にコウジ酸の薬効も安定に発揮される皮膚外用剤を提供することにある。
【0007】
【課題を解決するための手段】
本発明者は、この課題を解決すべく鋭意研究を進めた結果、意外にも、コウジ酸類と共に皮膚親和剤として、特定のシアノアクリレート系化合物または特定のベンゾトリアゾール基含有シリコーン誘導体から選ばれる1種または2種以上を配合することにより、増強的SPFかつ耐水性良好なSPF特性を有し、さらにはコウジ酸類の経皮吸収までも改善されることを見出し本発明を完成するに至った。
すなわち、本発明によれば、コウジ酸および/またはその誘導体と、皮膚親和剤として下記式(1)で表されるシアノアクリレート系化合物、または、下記式(2)と式(3)で表される化合物の結合体であるベンゾトリアゾール基含有シリコーン誘導体から選ばれる1種または2種以上を配合したことを特徴とする皮膚外用剤が提供される。
【化1】

Figure 0004671205
(式中、Rは直鎖または分鎖アルキル基を表す。)
【化2】
Figure 0004671205
(式中、Rは同一でも異なっていてもよく、C−C10のアルキル、フェニル、3,3,3−トリフルオロプロピルおよびトリメチルシリルオキシ基から選択され、数基準で基Rの少なくとも80%はメチル基であり、Bは同一でも異なっていてもよく、基Rおよび基Aから選択され、rは0から50までの整数であり、sは0から20までの整数であり、s=0であれば、2つの基Bのうち少なくとも1つは基Aを示し、Aは下記式(3)で表されるケイ素原子に直接結合する1価の基を表す。)
【化3】
Figure 0004671205
(式中、mは1から10までの整数であり、Xは水素またはC1−C4のアルキル基を表す。)
【0008】
【発明の実施の形態】
本発明において第1の成分として使用されるコウジ酸(5−オキシ−2−オキシメチル−γ−ピロン)としては、5−オキシ−2−オキシメチル−γ−ピロンの純品、コウジ酸生産能を有する公知の菌株を培養して得られるコウジ酸を主成分とする発酵液、該発酵液の濃縮液、および該発酵液からコウジ酸を抽出して結晶化したものなどが使用される。
【0009】
コウジ酸誘導体としては、本発明の目的から考えると、水溶性の誘導体との組み合わせにおいて特にメリットがあるが、脂溶性の誘導体に対しても効果が認められるため特に制約はなく、例えば、特公昭58−22151号公報、特公昭58−22152号公報、特公昭60−10005号公報、特公平1−45472号公報、特公平3−74229号公報、特許2933682号公報、特許2911204号公報、特許2919589号公報、特許2911208号公報および特開平5−78383号公報に開示されているコウジ酸のエステル化物、コウジ酸の2位の−CH2 OH基に糖類を結合させることによってコウジ酸分子を安定化させたコウジ酸誘導体およびコウジ酸配糖体など公知のものを単独または2種以上を組み合わせて用いることができる。
【0010】
本発明において、前記コウジ酸および/またはその誘導体は、化粧料、医薬部外品として許容し得るクリームや乳液などの外用の形態で患部に直接塗布するなどして使用される。この場合のコウジ酸および/またはその誘導体の配合量は、製剤全体に対して、0.001ないし10重量%、好ましくは0.1ないし5重量%の範囲で配合される。
【0011】
本発明において第2成分として使用されるシアノアクリレート系化合物としては、エチル−2−シアノ−3,3−ジフェニルアクリレート、2−エチルヘキシル−2−シアノ−3,3−ジフェニルアクリレート、オクチル−2−シアノ−3,3−ジフェニルアクリレートが挙げられ、特に、エチル−2−シアノ−3,3−ジフェニルアクリレート、2−エチルヘキシル−2−シアノ−3,3−ジフェニルアクリレートが好ましい。また、ベンゾトリアゾール基含有シリコーンとしては下記の化合物1から7が挙げられるが、特に、化合物1,3,4および6が好ましい。
【化合物1】
Figure 0004671205
【化合物2】
Figure 0004671205
【化合物3】
Figure 0004671205
【化合物4】
Figure 0004671205
【化合物5】
Figure 0004671205
【化合物6】
Figure 0004671205
【0012】
これら第2成分として配合されるシアノアクリレート系化合物およびベンゾトリアゾール基配合シリコーン誘導体の配合量は、その種類によって多少異なるが、通常、外用剤全体に対し0.001ないし10重量%、好ましくは0.1ないし5重量%である。
【0013】
以上の第1の成分ならびに第2の成分群を必須成分とする皮膚外用剤を、公知の製法によって調製すれば、耐水性良好なSPF特性を有し、さらにコウジ酸類の経皮吸収が改善された皮膚外用剤を提供することができる。
【0014】
また、本発明の製剤はO/W型エマルジョンおよびW/O型エマルジョンなどの乳化タイプに制限されるものではなく、成分の選択によって透明タイプの製剤にも同様に適用されるものである。それ以外にもO/W/O型やW/O/W型などの多層乳化型製剤やマイクロカプセル製剤化のための基礎技術として利用しても良い。
【0015】
本発明の外用剤の剤型は、外用施用上適するものであれば特に制限はなく、例えば、パップ剤、プラスター剤、ペースト剤、クリーム、軟膏、エアゾール剤、乳剤、ローション、乳液、エッセンス、パック、ゲル剤、パウダー、ファンデーション、サンケア、バスソルトなどの医薬品、医薬部外品ならびに化粧品として公知の形態で幅広く使用に供されるものである。
【0016】
さらに、本発明の外用剤を調製する場合、通常に用いられる種々の公知の有効成分、例えば、塩化カルプロニウム、セファランチン、ビタミンE、ビタミンEニコチネート、ニコチン酸、ニコチン酸アミド、ニコチン酸ベンジル、ショウキョウチンキ、トウガラシチンキ等の末梢血管拡張剤、カンフル、メントール、ハッカ油などの清涼剤、ヒノキチオール、塩化ベンザルコニウム、ウンデシレン酸などの抗菌剤、副腎皮質ホルモン、ε−アミノカプロン酸、塩化リゾチーム、グリチルリチン、アラントイン等の消炎剤、アスコルビン酸、アルブチンなどの色白剤、胎盤抽出物、甘草抽出物、紫根エキス、乳酸菌培養抽出物などの動物・植物・微生物由来の各種抽出物などを本発明の目的を損なわない範囲で、その時々の目的に応じて適宜添加して使用することができる。
【0017】
さらに、本発明の皮膚外用剤にはこれら公知の有効成分に加え、油脂類などの基剤成分のほか、必要に応じて公知の保湿剤、防腐剤、酸化防止剤、キレート剤、pH調整剤、香料、着色剤、紫外線吸収剤、散乱剤など種々の添加剤を本発明の目的を損なわない範囲で併用することができる。
【0018】
【実施例】
次に試験例および処方例を開示して本発明を説明するが、これらの開示は本発明の好適な態様を示すものであって、本発明を何ら限定するものではない。
【0019】
<試験例1>SPF測定試験・耐水性試験
日本化粧品工業連合会SPF測定法基準に従ってSPF測定を行った。
a)試験方法
18歳以上の健康な男性20名の背部50cm2 に、表1の試料▲1▼から▲3▼を各2mg/cm2 を塗布し、15分経過後、無塗布皮膚および試料▲1▼から▲3▼を塗布した皮膚0.5cm2 にキセノンアークソーラーシュミレーターを用い照射を行った。照射終了時から24時間後にMEDの判定を行い、各試料のMEDよりSPFを算出した。
SPF=試料塗布部のMED/試料無塗布部のMED
また、本発明製剤のウォータープルーフ効果を確認するため、上述の照射終了後、試料▲2▼および▲3▼について耐水性試験を行った。各試料を塗布し15分経過後、屋内プールで、20分間水中活動と20分の休憩とを繰り返し合計80分の水中活動を行った後、水分を自然乾燥させキセノンアークソーラーシュミレーターを用い照射を行い、同様にSPFを算出した。
【0020】
【表1】
Figure 0004671205
【0021】
【表2】
Figure 0004671205
【0022】
<試験結果>
表2に示したように、コウジ酸と皮膚親和剤とを併用することによりSPF効果が向上し、さらに本発明製剤は耐水性に優れることが確認された。
【0023】
<試験例2>経皮吸収性試験
a)試験方法
処方例2および処方例3のクリームを、ヘアレスマウス(第7週齢、オス)の背中の皮膚によりフランツ型セルを用いたin vitroの経皮吸収実験を行った。マウススキンを濾過し、レセプター液に到達したコウジ酸およびC18(総量)の経時的濃度変化をHPLCを用いて定量した結果処方例2について図1の結果を得た。
処方例3によるコウジ酸誘導体(2−エトキシメチル−5−ヒドロキシ−4H−ピラン−4−オン)の結果を図2に示した。
【0024】
<試験結果>
図1から図2に示したように、本発明の製剤は、明らかにコウジ酸類の経皮吸収が促進されており、コウジ酸と皮膚親和剤を併用した効果が確認できた。
【0025】
【処方例】
以下に本発明の皮膚外用剤の処方例を示す。処方例中、「適量」とは、全体で100重量%になる割合を意味する。
【0026】
Figure 0004671205
【0027】
Figure 0004671205
【0028】
Figure 0004671205
【0029】
Figure 0004671205
【0030】
Figure 0004671205
【0031】
Figure 0004671205
【0032】
Figure 0004671205
【0033】
Figure 0004671205
【0034】
Figure 0004671205
【0035】
Figure 0004671205
【0036】
上記の処方1ないし10は、いずれも表1、図1および図2に示したのと同様に、本発明の目的において満足する効果を有する製剤であることが確認された。
【0037】
【発明の効果】
本発明によれば、コウジ酸および/またはその誘導体に特定の紫外線吸収剤の1種または2種以上を配合することによって、コウジ酸類の着色を抑制し、乳化安定性を向上した使用感に優れた皮膚外用剤が提供できる。
【図面の簡単な説明】
【図1】処方例2のクリームと、該クリームから化合物1を除いたクリームを用いて行った経皮吸収性試験の結果を示すグラフである。
【図2】処方例3のクリームと、該クリームからコウジ酸誘導体である2−エトキシメチル−5−ヒドロキシ−4H−ピラン−4−オンを除いたクリームを用いて行った経皮吸収性試験の結果を示すグラフである。[0001]
BACKGROUND OF THE INVENTION
The present invention relates to an external preparation for skin, and more specifically, kojic acid and / or a derivative thereof, and one or two selected from a cyanoacrylate compound and / or a benzotriazole group-containing silicone derivative as a skin affinity agent. The present invention relates to an external preparation for skin characterized in that SPF characteristics with good water resistance are maintained and that percutaneous absorption of kojic acids is promoted by blending more than one species.
[0002]
[Prior art and its problems]
Kojic acid and its derivatives are known as substances having an ultraviolet absorption effect as disclosed in JP-A-55-157509, and have various other characteristics such as fairness effect and anti-inflammatory effect. It has been known. Regarding its usefulness, for example, Japanese Patent Publication No. 56-18869, Japanese Patent Publication No. 61-10447, Japanese Patent Publication No. 60-7961, Japanese Patent Publication No. 58-34446, Japanese Patent Publication No. 61-60801, Japanese Patent Publication No. Sho. 58-22151, JP-B 58-22152, JP-B 60-9722, JP-B 60-10005, JP-B 63-27322, JP-B 6-13448, JP-B 6-6 No. 16685, JP-A-1-132502, Japanese Patent No. 2549148, Japanese Patent No. 2712126, Japanese Patent No. 2504805, Japanese Patent Publication No. 5-30422, Japanese Patent No. 2977865, Japanese Patent Laid-Open No. 10-17468, Japanese Patent Also by the invention disclosed in Japanese Patent Application Laid-Open No. 10-59847 and Japanese Patent Application Laid-Open No. 10-212225. It is possible to know have.
[0003]
Thus, kojic acid and its derivatives (hereinafter collectively referred to simply as “kojic acids”) are very useful compounds, but since these compounds are water soluble, When blended in a low formulation, there is a limit to the adhesion after application. For example, after applying an O / W formulation of kojic acid, when the application surface gets wet with sweat or water, kojic acid flows down with the sweat or water, and the residual rate of kojic acid on the skin decreases. Therefore, there has been a problem that the stable functionality of kojic acid cannot be exhibited.
[0004]
In particular, kojic acid is known to be usable as an ultraviolet absorber. However, when a sunscreen agent containing kojic acid as an active ingredient is prepared in anticipation of this function, sweating may occur due to the use characteristics of the sunscreen agent. Because of the above-mentioned problems, kojic acid alone cannot achieve a stable sunblock effect, and various medicinal effects such as a whitening effect expected at the same time are also impaired.
[0005]
In recent years, consumers have demanded a formulation with a long-lasting sunscreen effect that does not contain a high amount of UV absorber from the viewpoint of reducing the burden on the skin and emphasizing the feeling of use. The development of a preparation that can be stably maintained, in particular, the functional characteristics of kojic acids stably even in an O / W preparation has been a continuing problem.
[0006]
[Problems to be solved by the invention]
An object of the present invention, a koji acid, as a skin friendly adhesive, by blending one or more selected from a particular cyanoacrylate compounds or a specific benzotriazole group-containing silicone derivative, conventional Koji is to solve the aforementioned problems of acid preparations, in particular, water resistance good SPF characteristics are retained, to provide a skin external preparation which is stable exhibited efficacy simultaneously kojic acid compound.
[0007]
[Means for Solving the Problems]
As a result of diligent research to solve this problem, the present inventor unexpectedly has one kind selected from a specific cyanoacrylate compound or a specific benzotriazole group-containing silicone derivative as a skin affinity agent together with kojic acids. Alternatively, the present invention has been completed by finding that blending two or more kinds has enhanced SPF and SPF characteristics with good water resistance, and further improved percutaneous absorption of kojic acids.
That is, according to the present invention, kojic acid and / or a derivative thereof, and a cyanoacrylate compound represented by the following formula (1) as a skin affinity agent, or represented by the following formula (2) and formula (3): An external preparation for skin, characterized in that one or more selected from benzotriazole group-containing silicone derivatives, which are conjugates of the above compounds, is blended.
[Chemical 1]
Figure 0004671205
(In the formula, R represents a linear or branched alkyl group.)
[Chemical 2]
Figure 0004671205
Wherein R may be the same or different and is selected from C 1 -C 10 alkyl, phenyl, 3,3,3-trifluoropropyl and trimethylsilyloxy groups, and on a number basis, at least 80% of the group R Is a methyl group, B may be the same or different and is selected from the group R and the group A, r is an integer from 0 to 50, s is an integer from 0 to 20, and s = 0 Then, at least one of the two groups B represents a group A, and A represents a monovalent group directly bonded to a silicon atom represented by the following formula (3) .
[Chemical 3]
Figure 0004671205
(In the formula, m is an integer from 1 to 10, and X represents hydrogen or a C1-C4 alkyl group.)
[0008]
DETAILED DESCRIPTION OF THE INVENTION
As kojic acid (5-oxy-2-oxymethyl-γ-pyrone) used as the first component in the present invention, pure product of 5-oxy-2-oxymethyl-γ-pyrone, kojic acid producing ability A fermented liquid mainly composed of kojic acid obtained by culturing a known strain having the above, a concentrated liquid of the fermented liquid, and a product obtained by extracting and crystallizing kojic acid from the fermented liquid.
[0009]
As a kojic acid derivative, there is a particular advantage in combination with a water-soluble derivative in view of the object of the present invention, but there is no particular limitation because an effect is recognized also for a fat-soluble derivative. 58-22151, JP-B-58-22152, JP-B-60-10005, JP-B-1-45472, JP-B-3-74229, JP-A-2933682, JP-A-2911204, JP-A-2919589 Kojic acid molecules disclosed by esterification of kojic acid, as disclosed in JP-A No. 2911208 and JP-A-5-78383, by binding a saccharide to the -CH 2 OH group at the 2-position of kojic acid. Known compounds such as kojic acid derivatives and kojic acid glycosides used alone or in combination of two or more Rukoto can.
[0010]
In the present invention, the kojic acid and / or a derivative thereof is used by directly applying to the affected part in a form for external use such as a cosmetic or quasi-drug acceptable cream or emulsion. In this case, the amount of kojic acid and / or its derivative is 0.001 to 10% by weight, preferably 0.1 to 5% by weight, based on the whole preparation.
[0011]
Examples of cyanoacrylate compounds used as the second component in the present invention include ethyl-2-cyano-3,3-diphenyl acrylate, 2-ethylhexyl-2-cyano-3,3-diphenyl acrylate, and octyl-2-cyano. -3,3-diphenyl acrylate is exemplified, and ethyl-2-cyano-3,3-diphenyl acrylate and 2-ethylhexyl-2-cyano-3,3-diphenyl acrylate are particularly preferable. Further, examples of the benzotriazole group-containing silicone include the following compounds 1 to 7, and compounds 1, 3, 4 and 6 are particularly preferable.
[Compound 1]
Figure 0004671205
[Compound 2]
Figure 0004671205
[Compound 3]
Figure 0004671205
[Compound 4]
Figure 0004671205
[Compound 5]
Figure 0004671205
[Compound 6]
Figure 0004671205
[0012]
The amount of the cyanoacrylate compound and the benzotriazole group-containing silicone derivative blended as the second component varies depending on the type, but is usually 0.001 to 10% by weight, preferably 0.8%, based on the total amount of the external preparation. 1 to 5% by weight.
[0013]
If a skin external preparation containing the above first component and second component group as essential components is prepared by a known production method, it has SPF characteristics with good water resistance and further improves percutaneous absorption of kojic acids. An external preparation for skin can be provided.
[0014]
Further, the preparation of the present invention is not limited to emulsification types such as O / W type emulsions and W / O type emulsions, and can be similarly applied to transparent type preparations depending on the selection of components. In addition to this, it may be used as a basic technique for making a multilayer emulsion type preparation such as O / W / O type or W / O / W type or a microcapsule preparation.
[0015]
The dosage form of the external preparation of the present invention is not particularly limited as long as it is suitable for external application. For example, a poultice, plaster, paste, cream, ointment, aerosol, emulsion, lotion, emulsion, essence, pack , Gels, powders, foundations, suncares, bath salts and other pharmaceuticals, quasi-drugs, and cosmetics that are widely used in known forms.
[0016]
Furthermore, when preparing the external preparation of the present invention, various known active ingredients that are commonly used, for example, carpronium chloride, cephalanthin, vitamin E, vitamin E nicotinate, nicotinic acid, nicotinic acid amide, benzyl nicotinate, and show Peripheral vasodilators such as tincture and chili pepper tincture, softeners such as camphor, menthol and mint oil, antibacterial agents such as hinokitiol, benzalkonium chloride, undecylenic acid, corticosteroids, ε-aminocaproic acid, lysozyme chloride, glycyrrhizin, Anti-inflammatory agents such as allantoin, whitening agents such as ascorbic acid and arbutin, various extracts derived from animals, plants and microorganisms such as placenta extract, licorice extract, purple root extract, lactic acid bacteria culture extract, etc. As long as there is no To be able to use.
[0017]
Furthermore, in addition to these known active ingredients, the skin external preparation of the present invention, in addition to base ingredients such as fats and oils, as well as known moisturizers, preservatives, antioxidants, chelating agents, pH adjusters Various additives such as fragrances, colorants, ultraviolet absorbers, and scattering agents can be used in combination as long as the object of the present invention is not impaired.
[0018]
【Example】
Next, the present invention will be described by disclosing test examples and formulation examples, but these disclosures show preferred embodiments of the present invention and do not limit the present invention in any way.
[0019]
<Test Example 1> SPF Measurement Test / Water Resistance Test SPF measurement was performed according to the Japan Cosmetic Industry Association SPF measurement method standard.
a) Test method 2 mg / cm 2 of each of the samples (1) to (3) in Table 1 was applied to 50 cm 2 of the back of 20 healthy men over 18 years old. Irradiation was performed on 0.5 cm 2 of the skin coated with (1) to (3) using a xenon arc solar simulator. MED was determined 24 hours after the end of irradiation, and SPF was calculated from the MED of each sample.
SPF = MED of sample application part / MED of sample non-application part
Further, in order to confirm the waterproof effect of the preparation of the present invention, a water resistance test was conducted on the samples (2) and (3) after the above-mentioned irradiation. After applying each sample for 15 minutes, in the indoor pool, repeat 20-minute underwater activities and 20-minute breaks for a total of 80-minute underwater activities, then dry the water naturally and irradiate using a xenon arc solar simulator. The SPF was calculated in the same manner.
[0020]
[Table 1]
Figure 0004671205
[0021]
[Table 2]
Figure 0004671205
[0022]
<Test results>
As shown in Table 2, it was confirmed that the SPF effect was improved by using kojic acid and a skin affinity agent in combination, and that the preparation of the present invention was excellent in water resistance.
[0023]
<Test Example 2> Transdermal absorbability test a) Test method In vitro treatment using the cream of Formulation Example 2 and Formulation Example 3 using Franz-type cells with the skin of the back of a hairless mouse (7 weeks old, male). Skin absorption experiments were performed. As a result of quantifying the time-dependent changes in the concentration of kojic acid and C18 (total amount) reaching the receptor fluid using HPLC, the results of FIG.
The results of the kojic acid derivative (2-ethoxymethyl-5-hydroxy-4H-pyran-4-one) according to Formulation Example 3 are shown in FIG.
[0024]
<Test results>
As shown in FIG. 1 to FIG. 2, the formulation of the present invention clearly promoted percutaneous absorption of kojic acids, and confirmed the effect of using kojic acid and a skin affinity agent in combination.
[0025]
[Prescription example]
The formulation example of the skin external preparation of this invention is shown below. In the formulation examples, “appropriate amount” means a ratio of 100% by weight as a whole.
[0026]
Figure 0004671205
[0027]
Figure 0004671205
[0028]
Figure 0004671205
[0029]
Figure 0004671205
[0030]
Figure 0004671205
[0031]
Figure 0004671205
[0032]
Figure 0004671205
[0033]
Figure 0004671205
[0034]
Figure 0004671205
[0035]
Figure 0004671205
[0036]
It was confirmed that each of the above formulations 1 to 10 is a preparation having an effect that is satisfactory for the purpose of the present invention, as shown in Table 1, FIG. 1 and FIG.
[0037]
【The invention's effect】
According to the present invention, the use of kojic acid and / or its derivatives with one or more specific ultraviolet absorbers suppresses the coloring of kojic acids and improves the usability of emulsification. An external skin preparation can be provided.
[Brief description of the drawings]
FIG. 1 is a graph showing the results of a transdermal absorbability test conducted using the cream of Formulation Example 2 and a cream obtained by removing Compound 1 from the cream.
FIG. 2 is a graph showing a transdermal absorbability test conducted using the cream of Formulation Example 3 and a cream obtained by removing 2-ethoxymethyl-5-hydroxy-4H-pyran-4-one as a kojic acid derivative from the cream. It is a graph which shows a result.

Claims (1)

コウジ酸および/またはその誘導体と、皮膚親和剤として下記式(1)で表されるシアノアクリレート系化合物、または、下記式(2)と式(3)で表される化合物の結合体であるベンゾトリアゾール基含有シリコーン誘導体から選ばれる1種または2種以上を配合したことを特徴とする皮膚外用剤。
Figure 0004671205
(式中、Rは直鎖または分鎖アルキル基を表す。)
Figure 0004671205
(式中、Rは同一でも異なっていてもよく、C−C10のアルキル、フェニル、3,3,3−トリフルオロプロピルおよびトリメチルシリルオキシ基から選択され、数基準で基Rの少なくとも80%はメチル基であり、Bは同一でも異なっていてもよく、基Rおよび基Aから選択され、rは0から50までの整数であり、sは0から20までの整数であり、s=0であれば、2つの基Bのうち少なくとも1つは基Aを示し、Aは下記式(3)で表されるケイ素原子に直接結合する1価の基を表す。)
Figure 0004671205
(式中、mは1から10までの整数であり、Xは水素またはC1−C4のアルキル基を表す。)
Benzo, which is a conjugate of kojic acid and / or a derivative thereof, and a cyanoacrylate compound represented by the following formula (1) or a compound represented by the following formula (2) and formula (3) as a skin affinity agent An external preparation for skin, comprising one or more selected from triazole group-containing silicone derivatives.
Figure 0004671205
(In the formula, R represents a linear or branched alkyl group.)
Figure 0004671205
Wherein R may be the same or different and is selected from C 1 -C 10 alkyl, phenyl, 3,3,3-trifluoropropyl and trimethylsilyloxy groups, and on a number basis, at least 80% of the group R Is a methyl group, B may be the same or different and is selected from the group R and the group A, r is an integer from 0 to 50, s is an integer from 0 to 20, and s = 0 Then, at least one of the two groups B represents a group A, and A represents a monovalent group directly bonded to a silicon atom represented by the following formula (3) .
Figure 0004671205
(In the formula, m is an integer from 1 to 10, and X represents hydrogen or a C1-C4 alkyl group.)
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Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH11507961A (en) * 1997-02-17 1999-07-13 ロレアル Sunscreen composition containing solid elastomeric organopolysiloxane

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JPH0696509B2 (en) * 1985-11-06 1994-11-30 ポーラ化成工業株式会社 Cosmetics
JPS63188609A (en) * 1987-01-30 1988-08-04 Sansho Seiyaku Kk External preparation preventing coloring
JP2974146B2 (en) * 1989-01-28 1999-11-08 三省製薬株式会社 Topical melanin production inhibitor
FR2642968B1 (en) * 1989-02-15 1991-06-07 Oreal COSMETIC USE OF BENZOTRIAZOLE-FUNCTIONAL DIORGANOPOLYSILOXANES AND NOVEL COSMETIC COMPOSITIONS CONTAINING THESE COMPOUNDS FOR PROTECTION OF THE SKIN AND HAIR
JP3661706B2 (en) * 1993-10-28 2005-06-22 三省製薬株式会社 Topical skin preparation
JP3656197B2 (en) * 1993-10-28 2005-06-08 三省製薬株式会社 Topical skin preparation
JP3661707B2 (en) * 1993-10-28 2005-06-22 三省製薬株式会社 Topical skin preparation
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JPH111420A (en) * 1997-06-09 1999-01-06 Shiseido Co Ltd Cosmetic
JPH11106323A (en) * 1997-09-30 1999-04-20 Sansho Seiyaku Co Ltd Skin lotion

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