JP2005015448A - Skin cosmetic - Google Patents
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- JP2005015448A JP2005015448A JP2003186418A JP2003186418A JP2005015448A JP 2005015448 A JP2005015448 A JP 2005015448A JP 2003186418 A JP2003186418 A JP 2003186418A JP 2003186418 A JP2003186418 A JP 2003186418A JP 2005015448 A JP2005015448 A JP 2005015448A
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Abstract
Description
【０００１】
【発明の属する技術分野】
本発明は、特に美白効果に優れ、更には優れた肌荒れ防止効果、老化防止効果及び美肌効果を発現し、皮膚を健やかに保つことのできる皮膚化粧料に関する。
【０００２】
【従来の技術】
従来、肌のしみやそばかす等の予防や治療を目的とする化粧料にはＬ−アスコルビン酸及びその誘導体、アルブチン等のハイドロキノン誘導体、コウジ酸等のピロン類が配合されている。
【０００３】
これらの物質は、メラニン生成の抑制、生成したメラニンの淡色漂白作用等の効果を有し、美白効果を有する物質として広く知られている。しかし、これらの物質は、例えばＬ−アスコルビン酸及びその誘導体の場合、保存安定性が不十分であったり、紫外線による炎症防止効果が十分に認められないことが多い。またハイドロキノン誘導体は安全性が十分でない等の問題がある。この様にメラニンの生成抑制効果、メラニンの淡色漂白作用、炎症防止効果、安全性等、総合的に優れた美白を目的とした化粧料を得ることは困難であった。
【０００４】
一方、４−（ｐ−ハイドロキシフェニル）−２−ブタノン（以下、ラズベリーケトンと略す）の配糖体はメラニン生成抑制効果があることが知られている（特許文献１参照）。また特定のビフェニル化合物にはチロシナーゼ活性阻害効果やメラニン生成抑制効果があることが知られている（特許文献２〜３参照）。しかし、これらを単独で配合した場合も、美白効果は充分に満足できるものではなかった。
【０００５】
【特許文献１】
特開平１０−１７４６２号公報
【特許文献２】
特開平６−１４５０４０号公報
【特許文献３】
特開平７−２５７４３号公報
【０００６】
【発明が解決しようとする課題】
上記事情において、本発明は、特に美白効果に優れ、更には優れた肌荒れ防止効果、老化防止効果及び美肌効果を発現し、皮膚を健やかに保つことのできる皮膚化粧料を提供することを目的とする。
【０００７】
【課題を解決するための手段】
そこで本発明者は鋭意研究した結果、 特定の配糖体の１種以上と、特定のビフェニル化合物の１種以上とを含有する皮膚化粧料が、紫外線障害によるメラニン生成を抑制すると共にメラニン色素の排泄を促し、相乗的に優れた美白効果を発現し、更には表皮の乾燥を防ぎ、皮膚の代謝を促進し、紫外線障害による皮膚の老化を防ぐ等、優れた肌荒れ防止効果、老化防止効果及び美肌効果を発現することを見出し、本発明を完成するに至った。
【０００８】
すなわち本発明は、下記一般式（１）
【化４】
（但し、Ｒは単糖類、二糖類から選ばれる糖の残基である）で表される配糖体と、下記一般式（２）又は一般式（３）で表されるビフェニル化合物の１種以上とを含有することを特徴とする皮膚化粧料である。
【００１０】
【化５】
（但し、Ｒ１はＣＨ３、Ｃ２Ｈ５、Ｃ３Ｈ７、ＣＨ２ＯＨ、Ｃ３Ｈ６ＯＨ、ＣＨ２ＣＨ＝ＣＨ２の置換基である）
【００１２】
【化６】
（但し、Ｒ２は、水素原子、若しくは炭素数１〜８の直鎖又は分岐鎖状の飽和炭化水素基である）
【００１４】
【発明の実施の形態】
以下、発明の実施の形態を詳述する。
【００１５】
本発明に用いられる配糖体の一部は公知の物質である（薬学雑誌：第９３巻、６号、７３３頁、１９７３年、およびフィトケミストリー：第２９巻、１２号、３８５３頁、１９９０年）。
【００１６】
本発明の配糖体を得る方法としては、天然物からの単離精製が可能である。また、アルブチンの合成方法として既に公知の方法（ＵＳＰ第３２０１３８５号公報）を用いて得ることができる。例えば、トルエン等の有機溶媒中においてラズベリーケトンとアセチル化糖を三フッ素化ホウ素やオキシ塩化リン等を触媒として縮合した後、アルカリ存在下にアセチル基を脱離することにより本発明の配糖体を白色の粉末結晶として容易に得ることもできる。
【００１７】
本発明で用いられる糖残基は、還元性の単糖類又は二糖類であり、具体的にはグルコース、ガラクトース、キシロース、マンノース、Ｎ−アセチルグルコサミン等の単糖類、マルトース、セロビオース、ゲンチビオース等の二糖類等を挙げることができる。尚、本発明の配糖体にはα結合及びβ結合を有する異性体が存在するが、そのどちらでも、あるいはそれらの混合物として用いることができる。
【００１８】
本発明で用いられる具体的な配糖体としては、ラズベリーケトン−Ｄ−グルコシド（α及びβ体）、ラズベリーケトン−Ｄ−ガラクトシド（α及びβ体）、ラズベリーケトン−Ｄ−キシロシド（α及びβ体）、ラズベリーケトン−Ｄ−マルトシド（α及びβ体）等を挙げることができる。これらの内、天然界に存在することが確認されており、また入手の容易さからラズベリーケトン−Ｄ−グルコシド（β体）がもっとも好ましい。尚、本発明に係る配糖体は、「人体用徐放性芳香組成物」として、既に提案されている（特開平７−１７９３２８号公報）。
【００１９】
本発明の特定の配糖体の配合量としては、特に限定されないが、皮膚化粧料の総量を基準として０．０１〜１０．０質量％が、本発明の効果を十分得ることができ好ましい。
【００２０】
本発明で用いられるビフェニル化合物は公知の物質であり、具体例としてデヒドロジクレオソール、デヒドロジオイゲノール、テトラハイドロマグノロール等が挙げられる（ジャーナル オブ オーガニック ケミストリィ、第２８巻、１０４８頁、１９６３年；日本化学会誌、第８７巻、第６号、６０３頁、１９６６年）。
【００２１】
その配合量は、皮膚化粧料の全量を基準として、０．０００１〜２０質量％が好ましく、更に好ましくは０．００１〜５質量％である。０．０００１質量％未満では十分な効果が得られず、２０質量％を超えてもその増量分に見合った効果の増大は見られないことがある。
【００２２】
本発明の皮膚化粧料には、上記原料の他に、色素、香料、防腐剤、界面活性剤、抗酸化剤、保湿剤等を、本発明の目的を達成する範囲内で適宜配合することができる。
【００２３】
本発明の皮膚化粧料の剤型としては、クリーム、乳液、化粧水、パック等が挙げられる。この皮膚化粧料は、例えば乳液等の場合、油相及び水相をそれぞれ加熱溶解したものを乳化分散して冷却する通常の方法により製造することができる。
【００２４】
【実施例】
以下、実施例及び比較例に基づいて本発明を詳述する。尚、実施例に記載の皮膚色明度回復試験法、しわ形成抑制試験方法（老化防止効果）、荒れ肌改善効果の測定法、官能テスト（美肌効果）は下記の通りである。
【００２５】
また、実施例におけるビフェニル化合物の名称を前記一般式のＲ１、Ｒ２の違いにより以下のごとく記載する。ビフェニル化合物１（Ｒ１；ＣＨ３）、ビフェニル化合物２（Ｒ１；Ｃ２Ｈ５）、ビフェニル化合物３（Ｒ１；Ｃ３Ｈ７）、ビフェニル化合物４（Ｒ１；ＣＨ２ＯＨ）、ビフェニル化合物５（Ｒ１；Ｃ３Ｈ６ＯＨ）、ビフェニル化合物６（Ｒ１；ＣＨ２ＣＨ＝ＣＨ２）、ビフェニル化合物７（Ｒ２；ＣＨ３）、ビフェニル化合物８（Ｒ２；Ｃ２Ｈ５）、ビフェニル化合物９（Ｒ２；Ｃ３Ｈ７）、ビフェニル化合物１０（Ｒ２；ｉｓｏ−Ｃ３Ｈ７）、ビフェニル化合物１１（Ｒ２；Ｃ８Ｈ１７）、ビフェニル化合物１２（Ｒ２；Ｈ）。
【００２６】
（１）皮膚色明度回復試験法
被験者２０名の背部皮膚にＵＶ−Ｂ領域の紫外線を最小紅斑量の２倍照射し、試料塗布部位と非塗布部位を設定して各々の皮膚の基準明度（Ｖ０値，Ｖ０’値）を測定した。引き続いて塗布部位には試料を１日２回ずつ１５週間連続塗布した後、３，６，９，１２，１５週間後の塗布部位及び非塗布部位の皮膚の明度（Ｖｎ値，Ｖｎ’値）を測定し、下記の判定基準にしたがって皮膚色の回復を評価した。尚、皮膚の明度（マンセル表色系Ｖ値）は高速分光色彩計で測定して得られたＸ，Ｙ，Ｚ値より算出した。また評価は被験者２０名ついて、３週間後の評価点の平均値で示した。
【００２７】
ΔＶ’・・・非塗布部位の回復値（Ｖｎ’−Ｖ０’）
【００２８】
（２）ヘアレスマウスによるしわ形成抑制試験
ヘアレスマウス（ＨＲ／ＩＣＲ、実験開始時６週齢）１０匹を用い、その背部に試料を８０μＬ塗布した。２時間後、７０％エタノールで皮膚表面上の試料を拭き取り、健康線用ランプ（東芝社製、ＳＥ２０）を６本用意し、１回の照射量が１ＭＥＤ以下となるように調節してＵＶ−Ｂ光の照射を行い、その直後に試料を塗布した。この操作を週５回、１６週間にわたって行った。照射のエネルギー量をＵＶ−Ｒａｄｉｏｍｅｔｅｒ（ＴＯＫＹＯ ＯＰＴＩＣＡＬ社製、ＵＶＲ−３０５／３６５Ｄ）を用いて測定した。試験終了後しわの度数を肉眼により下記基準（しわ指数）で評価した。試験結果は評価点の平均で示した。
【００２９】
しわ指数
０：しわが無形成
１：しわがわずかに形成
２：しわが微量形成
３：しわが若干形成
４：しわが強固に形成
【００３０】
（３）荒れ肌改善効果の測定試験法
下脚に荒れ肌を有する中高年被験者２０名を対象として４週間連続塗布効果を調べた。被験者の左側下脚試験部位に１日２回約１ｇの試料を塗布し、試験開始前及び終了後の皮膚の状態を下記の判定基準により判定した。右側下脚は試料を塗布せず対照とした。試験前後の試験部位と対照部位の判定結果を比較し、皮膚乾燥度が２段階以上改善された場合（例えば；＋→−，＋＋→±）を「有効」、１段階改善された場合を「やや有効」、変化がなかった場合を「無効」とした。試験結果は「有効」「やや有効」となった被験者の人数で示した。
【００３１】
皮膚の乾燥度の判定基準
− ：正常
± ：軽微乾燥、落屑なし
＋ ：乾燥、落屑軽度
＋＋ ：乾燥、落屑中等度
＋＋＋：乾燥、落屑顕著
【００３２】
（４）官能試験
被験者２０名が試料を１０日間連用した後の試料の特性を評価した。評価は、平滑性、美白効果、弾力性のアンケート項目に対し、「美白効果が感じられた」、「皮膚が滑らかになった」、「皮膚に張りが生じた」と回答した人数で示した。
【００３３】
実施例１〜１３，比較例１〜６
特定の配糖体とビフェニル化合物とを表１の組成において配合し、下記の調製方法に基いてスキンクリームを調製した。各々について前記の試験を実施し、その結果を表２、表３、表４、表５に示した。
組成
【００３４】
【表１】
【表２】
【表３】
【表４】
【表５】
調製方法
（Ａ）及び（Ｂ）の各成分をそれぞれ７０℃にて均一に溶解し、（Ａ）を攪拌しながら（Ｂ）を（Ａ）に注入して乳化分散した後、攪拌しながら温度５０℃まで冷却して（Ｃ）を加え、更に攪拌しながら温度３０℃まで冷却して調製する。
【００４０】
特性
本発明の実施例１〜１３のスキンクリームは、前記諸試験において良好な結果を示した。一方、比較例１〜６のスキンクリームは、十分な効果が認められず、本発明の実施例に比べて劣っていた。
【００４１】
実施例１４［スキンローション］
表６の組成により本発明のスキンローションを下記の製法によって調製した。
組成
【００４２】
【表６】
調製方法
（Ａ）及び（Ｂ）の各成分をそれぞれ混合溶解し、（Ｂ）を（Ａ）に加えて混合攪拌して調製した。
【００４４】
特性
この実施例１４のスキンローションは、前記諸試験において良好な結果を示した。
【００４５】
尚、上記実施例中で用いられた香料は、下記香料処方のものである。
【表７】
【発明の効果】
以上記載のごとく、本発明が、特に美白効果に優れ、更には優れた肌荒れ防止効果、老化防止効果及び美肌効果を発現し、皮膚を健やかに保つことのできる皮膚化粧料を提供することは明らかである。[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a skin cosmetic that is particularly excellent in a whitening effect, and further exhibits an excellent rough skin prevention effect, an anti-aging effect and a beautiful skin effect, and can keep the skin healthy.
[0002]
[Prior art]
Conventionally, cosmetics intended for prevention and treatment of skin spots, freckles and the like have been blended with L-ascorbic acid and its derivatives, hydroquinone derivatives such as arbutin, and pyrones such as kojic acid.
[0003]
These substances have effects such as inhibition of melanin production and light color bleaching of the produced melanin, and are widely known as substances having a whitening effect. However, in the case of L-ascorbic acid and its derivatives, for example, these substances often have insufficient storage stability, and the effect of preventing inflammation due to ultraviolet rays is not sufficiently observed. Hydroquinone derivatives also have problems such as insufficient safety. As described above, it has been difficult to obtain a cosmetic material that is comprehensively excellent in whitening, such as a melanin production inhibitory effect, a light-color bleaching action of melanin, an anti-inflammatory effect, and safety.
[0004]
On the other hand, glycosides of 4- (p-hydroxyphenyl) -2-butanone (hereinafter abbreviated as raspberry ketone) are known to have a melanin production inhibitory effect (see Patent Document 1). Moreover, it is known that a specific biphenyl compound has a tyrosinase activity inhibitory effect and a melanin production inhibitory effect (refer patent documents 2-3). However, even when these were blended alone, the whitening effect was not fully satisfactory.
[0005]
[Patent Document 1]
Japanese Patent Laid-Open No. 10-17462 [Patent Document 2]
JP-A-6-145040 [Patent Document 3]
Japanese Patent Laid-Open No. 7-25743 [0006]
[Problems to be solved by the invention]
In the above circumstances, the present invention has an object of providing a skin cosmetic that is particularly excellent in whitening effect, and further exhibits excellent skin roughness prevention effect, anti-aging effect and skin beautifying effect, and can keep the skin healthy. To do.
[0007]
[Means for Solving the Problems]
Therefore, as a result of earnest research, the present inventor has found that a skin cosmetic containing one or more specific glycosides and one or more specific biphenyl compounds suppresses the production of melanin due to ultraviolet ray damage and Promotes excretion, synergistically exhibits an excellent whitening effect, further prevents epidermis drying, promotes skin metabolism, prevents skin aging due to UV damage, etc. The present inventors have found that a skin beautifying effect is exhibited and have completed the present invention.
[0008]
That is, the present invention provides the following general formula (1)
[Formula 4]
(Wherein R is a residue of a sugar selected from monosaccharides and disaccharides) and a biphenyl compound represented by the following general formula (2) or general formula (3) It is a skin cosmetic characterized by containing the above.
[0010]
[Chemical formula 5]
(However, R 1 is a substituent of CH 3 , C 2 H 5 , C 3 H 7 , CH 2 OH, C 3 H 6 OH, CH 2 CH═CH 2 )
[0012]
[Chemical 6]
(However, R < 2 > is a hydrogen atom or a C1-C8 linear or branched saturated hydrocarbon group.)
[0014]
DETAILED DESCRIPTION OF THE INVENTION
Hereinafter, embodiments of the present invention will be described in detail.
[0015]
Some of the glycosides used in the present invention are known substances (Pharmaceutical Journal: 93, 6, 733, 1973, and Phytochemistry: 29, 12, 3853, 1990). ).
[0016]
The method for obtaining the glycoside of the present invention can be isolated and purified from natural products. Moreover, it can obtain using the already well-known method (USP 3201385 gazette) as a synthesis method of arbutin. For example, after condensing raspberry ketone and acetylated sugar in an organic solvent such as toluene using boron trifluoride or phosphorus oxychloride as a catalyst, the glucoside of the present invention is removed by eliminating the acetyl group in the presence of alkali. It can also be easily obtained as white powder crystals.
[0017]
The sugar residue used in the present invention is a reducing monosaccharide or disaccharide, specifically, monosaccharides such as glucose, galactose, xylose, mannose, N-acetylglucosamine, maltose, cellobiose, gentibiose and the like. Examples thereof include saccharides. The glycoside of the present invention includes isomers having an α bond and a β bond, either of which can be used as a mixture thereof.
[0018]
Specific glycosides used in the present invention include raspberry ketone-D-glucoside (α and β forms), raspberry ketone-D-galactoside (α and β forms), raspberry ketone-D-xyloside (α and β forms), Examples include raspberry ketone-D-maltoside (α and β isomers). Among these, it has been confirmed that it exists in the natural world, and raspberry ketone-D-glucoside (β form) is most preferable from the viewpoint of availability. The glycoside according to the present invention has already been proposed as a “sustained release fragrance composition for human body” (Japanese Patent Laid-Open No. 7-179328).
[0019]
The blending amount of the specific glycoside of the present invention is not particularly limited, but 0.01 to 10.0% by mass based on the total amount of the skin cosmetic is preferable because the effects of the present invention can be sufficiently obtained.
[0020]
The biphenyl compound used in the present invention is a known substance, and specific examples include dehydrodichloroeosol, dehydrodioigenol, tetrahydromagnolol (Journal of Organic Chemistry, 28, 1048, 1963; (The Chemical Society of Japan, Vol. 87, No. 6, 603, 1966).
[0021]
The blending amount is preferably 0.0001 to 20% by mass, more preferably 0.001 to 5% by mass, based on the total amount of the skin cosmetic. If it is less than 0.0001% by mass, a sufficient effect cannot be obtained, and if it exceeds 20% by mass, an increase in the effect commensurate with the increased amount may not be observed.
[0022]
In addition to the above-mentioned raw materials, the skin cosmetic of the present invention may be appropriately blended with pigments, fragrances, preservatives, surfactants, antioxidants, moisturizers and the like within the scope of achieving the object of the present invention. it can.
[0023]
Examples of the dosage form of the skin cosmetic of the present invention include creams, emulsions, lotions, packs and the like. For example, in the case of a milky lotion, this skin cosmetic can be produced by an ordinary method in which an oil phase and an aqueous phase are dissolved by heating and emulsified and cooled.
[0024]
【Example】
Hereinafter, the present invention will be described in detail based on examples and comparative examples. In addition, the skin color lightness recovery test method, wrinkle formation suppression test method (anti-aging effect), measurement method of rough skin improvement effect, and sensory test (skin-beautifying effect) described in Examples are as follows.
[0025]
Also, the name of the biphenyl compounds in Examples described as follows by the difference R 1, R 2 in the general formula. Biphenyl compound 1 (R 1 ; CH 3 ), biphenyl compound 2 (R 1 ; C 2 H 5 ), biphenyl compound 3 (R 1 ; C 3 H 7 ), biphenyl compound 4 (R 1 ; CH 2 OH), biphenyl Compound 5 (R 1 ; C 3 H 6 OH), biphenyl compound 6 (R 1 ; CH 2 CH═CH 2 ), biphenyl compound 7 (R 2 ; CH 3 ), biphenyl compound 8 (R 2 ; C 2 H 5 ), Biphenyl compound 9 (R 2 ; C 3 H 7 ), biphenyl compound 10 (R 2 ; iso-C 3 H 7 ), biphenyl compound 11 (R 2 ; C 8 H 17 ), biphenyl compound 12 (R 2 ; H).
[0026]
(1) Skin lightness recovery test method The back skin of 20 subjects was irradiated with UV rays in the UV-B region twice as much as the minimum erythema amount, the sample application site and the non-application site were set, and the standard brightness of each skin ( V 0 value, V 0 'value) were measured. Subsequently, the sample was applied to the application site twice a day for 15 weeks continuously, and then the lightness (V n value, V n ′) of the application site and non-application site after 3, 6, 9, 12, and 15 weeks. Value) was measured and skin color recovery was evaluated according to the following criteria. The lightness of the skin (Munsell color system V value) was calculated from X, Y, and Z values obtained by measurement with a high-speed spectral colorimeter. Moreover, evaluation was shown with the average value of the evaluation score after 20 weeks about 20 test subjects.
[0027]
ΔV′—Recovery value of non-application area (V n ′ −V 0 ′)
[0028]
(2) Wrinkle formation inhibition test using hairless mice Ten hairless mice (HR / ICR, 6 weeks of age at the start of the experiment) were used, and 80 μL of the sample was applied to the back. After 2 hours, wipe the sample on the skin surface with 70% ethanol, prepare six health line lamps (SE20, manufactured by Toshiba Corporation), and adjust the UV irradiation by adjusting the dose to 1 MED or less. The sample was applied immediately after irradiation with B light. This operation was performed 5 times a week for 16 weeks. The amount of irradiation energy was measured using a UV-Radiometer (manufactured by TOKYO OPTICAL, UVR-305 / 365D). After the test, the frequency of wrinkles was evaluated with the naked eye according to the following criteria (wrinkle index). The test results are shown as the average of the evaluation points.
[0029]
Wrinkle index 0: No wrinkle formation 1: Slight wrinkle formation 2: Small amount of wrinkle formation 3: Slight wrinkle formation 4: Strong wrinkle formation
(3) Measurement test method for effect of improving rough skin The effect of continuous application was examined for 20 middle-aged and older subjects having rough skin on the lower leg for 4 weeks. About 1 g of a sample was applied to the subject's left lower leg test site twice a day, and the skin condition before and after the test was determined according to the following criteria. The lower right leg was used as a control with no sample applied. The judgment results of the test site before and after the test and the control site are compared, and when the skin dryness is improved by two or more levels (for example, + → −, ++ → ±) is “effective”, and when the level is improved by 1 level, “Slightly effective” and “invalid” when there was no change. The test result was shown by the number of subjects who became “effective” and “slightly effective”.
[0031]
Judgment criteria for skin dryness-: Normal ±: Light dryness, no desquamation +: Dryness, mild desquamation ++: Dryness, moderate desquamation +++: Significant dryness, desquamation
(4) Sensory test The characteristics of the samples after 20 test subjects were used for 10 days were evaluated. The evaluation was shown by the number of respondents who answered that “whitening effect was felt”, “skin became smooth”, or “skin became stretched” for the questionnaire items of smoothness, whitening effect, and elasticity. .
[0033]
Examples 1-13, Comparative Examples 1-6
A specific glycoside and a biphenyl compound were blended in the composition shown in Table 1, and a skin cream was prepared based on the following preparation method. The above test was carried out for each, and the results are shown in Table 2, Table 3, Table 4, and Table 5.
Composition [0034]
[Table 1]
[Table 2]
[Table 3]
[Table 4]
[Table 5]
Each component of the preparation methods (A) and (B) is uniformly dissolved at 70 ° C., and (B) is poured into (A) while stirring (A) and emulsified and dispersed. Cool to 50 ° C., add (C), and further cool to 30 ° C. with stirring.
[0040]
Characteristics The skin creams of Examples 1 to 13 of the present invention showed good results in the above tests. On the other hand, the skin creams of Comparative Examples 1 to 6 were inferior to the examples of the present invention because sufficient effects were not recognized.
[0041]
Example 14 [Skin Lotion]
The skin lotion of the present invention was prepared by the following production method according to the composition shown in Table 6.
Composition [0042]
[Table 6]
The components of preparation methods (A) and (B) were mixed and dissolved, and (B) was added to (A) and mixed and stirred.
[0044]
Properties The skin lotion of Example 14 showed good results in the above tests.
[0045]
In addition, the fragrance | flavor used in the said Example is a thing of the following fragrance | flavor prescription.
[Table 7]
【The invention's effect】
As described above, it is clear that the present invention provides a skin cosmetic that is particularly excellent in whitening effect, and further exhibits excellent skin roughening prevention effect, anti-aging effect and skin care effect, and can keep the skin healthy. It is.
Claims (1)
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| JP2003186418A JP2005015448A (en) | 2003-06-30 | 2003-06-30 | Skin cosmetic |
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| JP2003186418A JP2005015448A (en) | 2003-06-30 | 2003-06-30 | Skin cosmetic |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006328048A (en) * | 2005-04-28 | 2006-12-07 | Kanebo Cosmetics Inc | Skin cosmetic |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006328048A (en) * | 2005-04-28 | 2006-12-07 | Kanebo Cosmetics Inc | Skin cosmetic |
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