JP5552741B2 - Whitening agent containing zinc as an active ingredient - Google Patents
Whitening agent containing zinc as an active ingredient Download PDFInfo
- Publication number
- JP5552741B2 JP5552741B2 JP2008522638A JP2008522638A JP5552741B2 JP 5552741 B2 JP5552741 B2 JP 5552741B2 JP 2008522638 A JP2008522638 A JP 2008522638A JP 2008522638 A JP2008522638 A JP 2008522638A JP 5552741 B2 JP5552741 B2 JP 5552741B2
- Authority
- JP
- Japan
- Prior art keywords
- zinc
- acid
- zinc salt
- salt
- appropriate amount
- 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.)
- Active
Links
- 230000002087 whitening effect Effects 0.000 title claims description 33
- 239000011701 zinc Substances 0.000 title description 39
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 title description 34
- 229910052725 zinc Inorganic materials 0.000 title description 33
- 239000003795 chemical substances by application Substances 0.000 title description 26
- 239000004480 active ingredient Substances 0.000 title description 4
- 239000000203 mixture Substances 0.000 claims description 53
- -1 amino acid ester Chemical class 0.000 claims description 47
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 40
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- 239000011668 ascorbic acid Substances 0.000 claims description 19
- CHCZPSBPZFXDQJ-UHFFFAOYSA-L zinc;2-oxopyrrolidine-1-carboxylate Chemical compound [Zn+2].[O-]C(=O)N1CCCC1=O.[O-]C(=O)N1CCCC1=O CHCZPSBPZFXDQJ-UHFFFAOYSA-L 0.000 claims description 19
- 229960005070 ascorbic acid Drugs 0.000 claims description 18
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
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- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 12
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 12
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 12
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 11
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- 210000004027 cell Anatomy 0.000 description 11
- HXEACLLIILLPRG-RXMQYKEDSA-N l-pipecolic acid Natural products OC(=O)[C@H]1CCCCN1 HXEACLLIILLPRG-RXMQYKEDSA-N 0.000 description 11
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- CANRESZKMUPMAE-UHFFFAOYSA-L Zinc lactate Chemical compound [Zn+2].CC(O)C([O-])=O.CC(O)C([O-])=O CANRESZKMUPMAE-UHFFFAOYSA-L 0.000 description 5
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- 238000000034 method Methods 0.000 description 5
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- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 5
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- 108091032973 (ribonucleotides)n+m Proteins 0.000 description 4
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- 239000002994 raw material Substances 0.000 description 1
- 238000003757 reverse transcription PCR Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000007788 roughening Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 230000009759 skin aging Effects 0.000 description 1
- 230000037380 skin damage Effects 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- YRWWOAFMPXPHEJ-OFBPEYICSA-K sodium L-ascorbic acid 2-phosphate Chemical compound [Na+].[Na+].[Na+].OC[C@H](O)[C@H]1OC(=O)C(OP([O-])([O-])=O)=C1[O-] YRWWOAFMPXPHEJ-OFBPEYICSA-K 0.000 description 1
- PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 description 1
- 235000010378 sodium ascorbate Nutrition 0.000 description 1
- 229960005055 sodium ascorbate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- GJBHGUUFMNITCI-QTNFYWBSSA-M sodium;(2s)-2-aminopentanedioate;hydron;hydrate Chemical compound O.[Na+].OC(=O)[C@@H](N)CCC([O-])=O GJBHGUUFMNITCI-QTNFYWBSSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003270 steroid hormone Substances 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 239000000606 toothpaste Substances 0.000 description 1
- 229940034610 toothpaste Drugs 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 150000003700 vitamin C derivatives Chemical class 0.000 description 1
- 239000012463 white pigment Substances 0.000 description 1
- 229940062776 zinc aspartate Drugs 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- RZLVQBNCHSJZPX-UHFFFAOYSA-L zinc sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Zn+2].[O-]S([O-])(=O)=O RZLVQBNCHSJZPX-UHFFFAOYSA-L 0.000 description 1
- KPKLKIOSPIATFO-QXGOIDDHSA-L zinc;(2s)-2-amino-3-phenylpropanoate Chemical compound [Zn+2].[O-]C(=O)[C@@H](N)CC1=CC=CC=C1.[O-]C(=O)[C@@H](N)CC1=CC=CC=C1 KPKLKIOSPIATFO-QXGOIDDHSA-L 0.000 description 1
- POEVDIARYKIEGF-CEOVSRFSSA-L zinc;(2s)-2-aminobutanedioate;hydron Chemical compound [Zn+2].[O-]C(=O)[C@@H](N)CC(O)=O.[O-]C(=O)[C@@H](N)CC(O)=O POEVDIARYKIEGF-CEOVSRFSSA-L 0.000 description 1
- WAMAIUZWKRNZBB-WFGSYIHQSA-L zinc;(2s,3s)-2-amino-3-methylpentanoate Chemical compound [Zn+2].CC[C@H](C)[C@H](N)C([O-])=O.CC[C@H](C)[C@H](N)C([O-])=O WAMAIUZWKRNZBB-WFGSYIHQSA-L 0.000 description 1
- GAMIYQSIKAOVTG-UHFFFAOYSA-L zinc;2-aminopentanedioate Chemical compound [Zn+2].[O-]C(=O)C(N)CCC([O-])=O GAMIYQSIKAOVTG-UHFFFAOYSA-L 0.000 description 1
- BUJKOUKORSHUMB-UHFFFAOYSA-L zinc;2-oxopyrrolidine-1-carboxylate;dihydrate Chemical compound O.O.[Zn+2].[O-]C(=O)N1CCCC1=O.[O-]C(=O)N1CCCC1=O BUJKOUKORSHUMB-UHFFFAOYSA-L 0.000 description 1
- ZNVKGUVDRSSWHV-UHFFFAOYSA-L zinc;4-hydroxybenzenesulfonate Chemical compound [Zn+2].OC1=CC=C(S([O-])(=O)=O)C=C1.OC1=CC=C(S([O-])(=O)=O)C=C1 ZNVKGUVDRSSWHV-UHFFFAOYSA-L 0.000 description 1
Images
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- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
本発明は皮膚の美白剤、およびこれを含有する化粧料組成物に関する。 The present invention relates to a skin lightening agent and a cosmetic composition containing the same.
皮膚の美白剤に関しては、アルブチン、エラグ酸、コウジ酸、ビタミンＣ誘導体や各種ハーブエキスなどが知られているが、皮膚にマイルドで化粧料への配合が容易な成分が求められている。
一方、亜鉛については、酸化亜鉛がおむつかぶれを抑制することが報告されている（例えば、ＦＥＢＳ Ｌｅｔｔｅｒｓ，３８４巻，９２〜９６ページ、１９９６年）。しかしながら、この化合物は水にも油性成分にも難溶で、化粧品や皮膚外用剤の成分として用いることが難しい。また、有機亜鉛塩の一種であるグリシン亜鉛塩について、メタロチオネインの誘導促進作用を有することが知られている（特開２００５−２４７７２９号公報）。これは抗酸化効果やラジカル補足能などの経路により、メラニン合成阻害や細胞毒性阻害などのＵＶによる皮膚損傷の抑制作用である。同じく有機亜鉛の一種であるピロリドンカルボン酸亜鉛塩やアシルアミノ酸亜鉛塩については、ＵＶにより惹起されるＡＰ−１やＮＦ−κＢなどの炎症因子を抑制することが知られている（特開２００６−０２２０９０号公報、国際公開ＷＯ２００５／１２３０６２号パンフレット）。
その他、有機亜鉛塩や無機亜鉛塩については、収れん作用、消炎作用、白色顔料、紫外線防御剤、消臭・殺菌剤の用途で化粧料組成物に配合することが知られているが、効果を期待できる濃度領域近傍での利用は皮膚に対する刺激性から、化粧品としての利用が難しかった。また低濃度での利用では、皮膚への上記有効性を見出せず、亜鉛化合物の化粧料への配合は進んでいない。As skin whitening agents, arbutin, ellagic acid, kojic acid, vitamin C derivatives and various herbal extracts are known. However, ingredients that are mild to skin and easy to be blended into cosmetics are required.
On the other hand, regarding zinc, it has been reported that zinc oxide suppresses diaper rash (for example, FEBS Letters, 384, 92-96, 1996). However, this compound is hardly soluble in water and oily components and is difficult to use as a component in cosmetics and skin external preparations. Further, glycine zinc salt, which is a kind of organic zinc salt, is known to have a metallothionein induction promoting action (Japanese Patent Laid-Open No. 2005-247729). This is an action of suppressing skin damage caused by UV, such as inhibition of melanin synthesis and inhibition of cytotoxicity, through pathways such as an antioxidant effect and radical scavenging ability. Similarly, pyrrolidonecarboxylic acid zinc salts and acylamino acid zinc salts, which are also a kind of organic zinc, are known to suppress UV-induced inflammatory factors such as AP-1 and NF-κB (Japanese Patent Laid-Open No. 2006-2006). No. 022090, International Publication WO2005 / 123062 Pamphlet).
In addition, organic zinc salts and inorganic zinc salts are known to be incorporated into cosmetic compositions for astringent, anti-inflammatory, white pigment, UV protection, deodorant and bactericidal agents. Use in the vicinity of the expected concentration range has been difficult to use as a cosmetic because of irritation to the skin. In addition, when it is used at a low concentration, the above-mentioned effectiveness on the skin is not found, and the compounding of zinc compounds into cosmetics has not progressed.
本発明者らは、上記目的を達成すべく鋭意検討を重ねた結果、亜鉛をヒト色素細胞（メラニン産生細胞（メラノサイト））に導入することにより、アスコルビン酸トランスポーターの発現促進効果を有することを見出し、これに伴い美白効果が得られることを見出した。
アスコルビン酸トランスポーターは、細胞へのアスコルビン酸の取り込みを促進する膜タンパク質であり（Ｈｉｒｏｙａｓｕ Ｔｓｕｋａｇｕｃｈｉ ｅｔｃ（１９９９）Ｎａｔｕｒｅ ３９９，７０−７５を参照せよ）。アスコルビン酸トランスポーターの発現増強により、ヒト色素細胞（メラニン産生細胞（メラノサイト））において、アスコルビン酸の細胞内への取り込み促進がおこり、メラニン産生が抑制される。
本発明の目的は、上記の知見に基づき、優れた美白作用を有する美白剤、およびこれを含有する化粧料組成物を得ることにある。
課題を解決するための手段
すなわち、本発明は、亜鉛を有効成分として含有することを特徴とする美白用組成物に関する。
皮膚刺激性、細胞内への導入効率などの観点から、現実的に実施可能な亜鉛の導入方法としては、亜鉛を亜鉛塩にして、一定濃度、皮膚に塗布することが必要であり、具体的には以下の発明を含む。
（１）亜鉛を有効成分として含有する美白剤。
（２）亜鉛が、ピロリドンカルボン酸亜鉛塩、グルコン酸亜鉛塩、スルホ石灰酸亜鉛塩、乳酸亜鉛塩、各種アミノ酸亜鉛塩、アシルアミノ酸亜鉛塩、硫酸亜鉛、塩化亜鉛および酸化亜鉛からなる群より選択される化合物である、（１）記載の美白剤。
（３）亜鉛が、ピロリドンカルボン酸亜鉛塩である（１）記載の美白剤。
（４）美白が、ヒト色素細胞（メラニン産生細胞（メラノサイト））のアスコルビン酸トランスポーターの発現増強を介してされるものである、上記（１）から（３）に記載の美白剤。
（５）亜鉛を、有効成分として配合することを特徴とする、美白用組成物。
（６）亜鉛が、ピロリドンカルボン酸亜鉛塩、グルコン酸亜鉛塩、スルホ石灰酸亜鉛塩、乳酸亜鉛塩、各種アミノ酸亜鉛塩、アシルアミノ酸亜鉛塩、硫酸亜鉛、塩化亜鉛および酸化亜鉛からなる群より選択される化合物である、（５）記載の美白用組成物。
（７）亜鉛が、ピロリドンカルボン酸亜鉛塩である（５）記載の美白用組成物。
（８）亜鉛を、組成物中に１μＭ〜１００ｍＭの濃度で存在するように配合することを特徴とする、上記（５）〜（７）に記載の美白用組成物。
（９）さらに、アスコルビン酸が配合される、上記（５）〜（８）に記載の美白用組成物。
（１０）１μＭ〜１００ｍＭの濃度の亜鉛、および、５ｍＭ〜６００ｍＭの濃度のアスコルビン酸を配合することを特徴とする上記（５）〜（９）に記載の美白用組成物。
（１１）さらに、Ｎ−アシル酸性アミノ酸エステル、アミノ酸またはアミノ酸誘導体が配合される、上記（５）〜（１０）に記載の美白用組成物。
（１２）軟膏、化粧水、ローション、クリーム、乳液、美容液、パック、ファンデーション、または液体ハンドソープである上記（５）〜（１１）に記載の美白用組成物。
（１３）肌の美白のための、亜鉛の使用。
（１４）肌の美白のための、ピロリドンカルボン酸亜鉛塩、グルコン酸亜鉛塩、スルホ石灰酸亜鉛塩、乳酸亜鉛塩、各種アミノ酸亜鉛塩、アシルアミノ酸亜鉛塩、硫酸亜鉛、塩化亜鉛および酸化亜鉛からなる群より選択される亜鉛塩の使用。
（１５）肌の美白のための、ピロリドンカルボン酸亜鉛塩の使用。
（１６）上記（５）〜（１１）に記載の組成物を皮膚に塗布することを特徴とする美白方法。As a result of intensive studies to achieve the above object, the present inventors have shown that the introduction of zinc into human pigment cells (melanin producing cells (melanocytes)) has an effect of promoting the expression of ascorbic acid transporter. It was found that a whitening effect can be obtained with the heading.
Ascorbic acid transporters are membrane proteins that promote the uptake of ascorbic acid into cells (see Hiroya Tsukaguchi etc (1999) Nature 399, 70-75). By enhancing the expression of the ascorbic acid transporter, the uptake of ascorbic acid into cells occurs in human pigment cells (melanin producing cells (melanocytes)), and melanin production is suppressed.
An object of the present invention is to obtain a whitening agent having an excellent whitening action and a cosmetic composition containing the same based on the above findings.
Means for Solving the Problems That is, the present invention relates to a whitening composition comprising zinc as an active ingredient.
From the viewpoint of skin irritation, introduction efficiency into cells, etc., as a practical zinc introduction method, it is necessary to make zinc a zinc salt and apply it to the skin at a certain concentration. Includes the following inventions.
(1) A whitening agent containing zinc as an active ingredient.
(2) Zinc is selected from the group consisting of zinc pyrrolidone carboxylic acid, zinc gluconate, zinc sulfolime, zinc lactate, various amino acid zinc salts, acyl amino acid zinc salts, zinc sulfate, zinc chloride and zinc oxide. The whitening agent according to (1), wherein
(3) The whitening agent according to (1), wherein the zinc is a pyrrolidone carboxylic acid zinc salt.
(4) The whitening agent according to any one of (1) to (3) above, wherein the whitening is performed through enhanced expression of an ascorbic acid transporter in human pigment cells (melanin producing cells (melanocytes)).
(5) A whitening composition comprising zinc as an active ingredient.
(6) Zinc is selected from the group consisting of zinc pyrrolidone carboxylic acid, zinc gluconate, zinc sulfolime, zinc lactate, various amino acid zinc salts, acyl amino acid zinc salts, zinc sulfate, zinc chloride and zinc oxide. The whitening composition according to (5), wherein
(7) The whitening composition according to (5), wherein the zinc is a pyrrolidone carboxylic acid zinc salt.
(8) The whitening composition as described in (5) to (7) above, wherein zinc is blended so as to be present in the composition at a concentration of 1 μM to 100 mM.
(9) The whitening composition as described in (5) to (8) above, further comprising ascorbic acid.
(10) The whitening composition as described in (5) to (9) above, wherein zinc at a concentration of 1 μM to 100 mM and ascorbic acid at a concentration of 5 mM to 600 mM are blended.
(11) The whitening composition according to the above (5) to (10), further comprising an N-acyl acidic amino acid ester, an amino acid or an amino acid derivative.
(12) The whitening composition according to the above (5) to (11), which is an ointment, lotion, lotion, cream, milky lotion, cosmetic liquid, pack, foundation, or liquid hand soap.
(13) Use of zinc for skin whitening.
(14) From pyrrolidone carboxylic acid zinc salt, gluconic acid zinc salt, sulfocalcic acid zinc salt, zinc lactate, various amino acid zinc salts, acylamino acid zinc salts, zinc sulfate, zinc chloride and zinc oxide for skin whitening Use of a zinc salt selected from the group consisting of:
(15) Use of pyrrolidone carboxylic acid zinc salt for skin whitening.
(16) A whitening method comprising applying the composition according to the above (5) to (11) to the skin.
図１は、ピロリドンカルボン酸亜鉛塩によるメラノサイトにおけるアスコルビン酸トランスポーターｍＲＮＡ発現増強効果を確認した図である。
発明の詳細な説明FIG. 1 is a diagram showing the effect of enhancing the expression of ascorbic acid transporter mRNA in melanocytes by pyrrolidone carboxylic acid zinc salt.
Detailed Description of the Invention
以下、本発明の詳細を説明する。
本発明において、美白とは、肌が美しく白いという概念を意味し、美白剤は、治療の目的のもの、および予防の目的のもののいずれをも包含する意味である。
本発明に用いられる亜鉛は、皮膚刺激性、細胞内への導入効率などの観点から、現実的に亜鉛を亜鉛塩にして、一定濃度、皮膚に塗布することが必要である。この場合有機亜鉛塩および無機亜鉛塩のいずれも使用することができる。有機亜鉛塩としては、ピロリドンカルボン酸亜鉛塩、グルコン酸亜鉛塩、スルホ石灰酸亜鉛塩、乳酸亜鉛塩、各種アミノ酸亜鉛塩、アシルアミノ酸亜鉛塩などが含まれる。無機亜鉛としては、硫酸亜鉛、塩化亜鉛、酸化亜鉛などが含まれる。
アミノ酸亜鉛塩としては、グリシン亜鉛塩、アラニン亜鉛塩、バリン亜鉛塩、ロイシン亜鉛塩、イソロイシン亜鉛塩、フェニルアラニン亜鉛塩、メチオニン亜鉛塩、トリプトファン亜鉛塩、アスパラギン亜鉛塩、グルタミン亜鉛塩、セリン亜鉛塩、スレオニン亜鉛塩、システイン亜鉛塩、チロシン亜鉛塩、アスパラギン酸亜鉛塩、グルタミン酸亜鉛塩、リジン亜鉛塩、アルギニン亜鉛塩、若しくはヒスチジン亜鉛塩などの各種アミノ酸亜鉛塩が挙げられる。
アシルアミノ酸亜鉛塩とは、アミノ酸のアミノ基にアシル基が結合した化合物の亜鉛塩であるが、例えば、アシルアミノ酸としては以下の構造式を有する化合物が挙げられる。
美白効果を高めるという観点において、血流促進効果を持つピロリドンカルボン酸の亜鉛塩は、血管内のアスコルビン酸などの有用物質を塗布部位に集めることが期待されるため、アスコルビン酸トランスポーターの発現促進効果がより顕著に美白効果に反映される亜鉛塩である。
ピロリドンカルボン酸亜鉛塩とは、２−ピロリドン−５−カルボン酸の亜鉛塩であって、各種水和物であってもよい。以下、単に「ＰＣＡ亜鉛塩」、「ＰＣＡＺｎ塩」ともいう。なお、実施例において使用したピロリドンカルボン酸亜鉛塩は２水和物であり、以下の構造を有する。
本発明の美白剤は、化粧料や皮膚外用剤などの組成物に配合して使用される。この際、その配合量を１μＭ〜１００ｍＭ（ＰＣＡ亜鉛塩として０．００００３５重量％〜３．５重量％）、好ましくは、１μＭ〜５０ｍＭ（ＰＣＡ亜鉛塩として０．００００３５重量％〜０．３５重量％）、更に好ましくは、１μＭ〜１０ｍＭ（ＰＣＡ亜鉛塩として０．００００３５重量％〜０．０３５重量％）配合する。多くの亜鉛塩の場合、３．５重量％以上の配合では皮膚に対して刺激感が生じる、あるいは、きしみ感などが発生する問題があり、また、培養皮膚細胞を用いた検討によれば、高濃度では目的の効果は起こらなくなり、好ましくない。
亜鉛を化粧料や皮膚外用剤に配合するとき、これらの成分以外に、一般に化粧料あるいは皮膚外用剤として使用される成分を本発明の効果を阻害しない範囲で添加することができる。
また、本発明の更なる態様は、亜鉛と、アスコルビン酸、Ｎ−アシル酸性アミノ酸エステル、アミノ酸およびアミノ酸誘導体からなる群より選択される１種また２種以上が同時に配合されてなる組成物に関する。
中でも、アスコルビン酸５〜６００ｍＭ程度、好ましくは５〜３００ｍＭ程度を、亜鉛と同時に配合することが、美白効果の観点から好ましい。この際、アスコルビン酸としては、化粧料に配合可能な形態であれば、各種誘導体を用いても良い。すなわち、アスコルビン酸のフリー体や各種塩（アスコルビン酸ナトリウム、アスコルビン酸−２−リン酸ナトリウム、アスコルビン酸−２−リン酸マグネシウム、アスコルビン酸−２−硫酸ナトリウム等）に加えて、各種配糖体（アスコルビル−２−グルコシド等）やアスコルビン酸エステル（６−ステアリン酸アスコルビル、６−パルミチン酸アスコルビル、２，６−ジパルミチン酸アスコルビル、２，３，５，６−テトラヘキシルデカン酸アスコルビル、トコフェリルアスコルビン酸等）等の各種誘導体を用いても良い。
本発明において用いるＮ−アシル酸性アミノ酸エステルは、次の構造で表されるものである。
特にＮ−アシル酸性ジエステルが好ましく、その好適な具体例としては、例えば、Ｎ−ラウロイルグルタミン酸ジ（コレステリルベヘニルオクチルドデシル）、Ｎ−ラウロイルグルタミン酸ジ（コレステリルオクチルドデシル）、Ｎ−ラウロイルグルタミン酸ジ（フィトステリル２−オクチルドデシル）、Ｎ−ラウロイルグルタミン酸ジ（オクチルドデシルフィトステリルベヘニル）などが挙げられ、それらは、味の素株式会社から、それぞれ、「エルデュウＣＬ−３０１」、「エルデュウＣＬ−２０２」、「エルデュウＰＳ−２０３」、「エルデュウＰＳ−３０４」の商品名で市販されている。
本発明において、このＮ−アシル酸性アミノ酸エステルは、保湿力や整肌性の向上に寄与し、また、安定性の向上にも寄与するが、その効果を適切に発現させるためには、その配合量は、０．０１重量％以上にすることが好ましく、０．１重量％以上にすることがより好ましく、０．５重量％以上にすることがさらに好ましく、また、Ｎ−アシル酸性アミノ酸エステルの配合量を必要以上に多くすると、べたつくおそれがあるので、２０重量％以下にすることが好ましく、１０重量％以下にすることがより好ましく、５重量％以下にすることがさらに好ましい。
アミノ酸またはアミノ酸誘導体は、保湿効果の向上に寄与させるために組成物中に配合されるが、そのアミノ酸としては、例えば、アラニン、アルギニン、アスパラギン、アスパラギン酸、シトルリン、システイン、シスチン、グルタミン、グルタミン酸、グリシン、ヒスチジン、オキシプロリン、イソロイシン、ロイシン、リジン、メチオニン、オルニチン、フェニルアラニン、プロリン、セリン、スレオニン、トリプトファン、チロシン、バリンなどが挙げられ、それらのＬ体、Ｄ体またはＤＬ体のいずれであってもよいし、また、それらの塩であってもよい。そのような塩としては、例えば、ナトリウム塩、カリウム塩、トリエタノールアミン塩などが挙げられる。
また、アミノ酸誘導体としては、前述のアミノ酸を環化、アシル化またはエステル化したものであって、例えば、アセチルグルタミン酸、アセチルメチオニン、アセチルシステイン、Ｎ，Ｎ−ジアセチル−Ｌ−シスチンジメチルエステル、アシルグルタミン酸塩、アシルグリシン塩、アシルアラニン塩、アシルアルギニンエチルエステル塩などが挙げられる。ただし、Ｎ−アシル酸性アミノ酸エステルは含まない。
これらの成分以外に、一般に化粧料あるいは皮膚外用剤として使用される成分を本発明の効果を阻害しない範囲で添加することができる。一般に化粧料あるいは皮膚外用剤に使用されている成分としては、抗酸化剤、抗炎症剤、紫外線吸収剤、細胞賦活剤、保湿剤、金属キレート剤、油性原料、界面活性剤、溶剤、高分子物質、粉体物質、色素類、香料、経皮吸収促進剤及びステロイドホルモン等を挙げることができる。
上記亜鉛を含有する組成物の形態には特に制限はなく、溶液状、ペースト状、ゲル状、固体状、粉末状等任意の形態をとることができる。また、本発明の組成物は、オイル、ローション、クリーム、乳液、ゲル、シャンプー、ヘアリンス、ヘアコンディショナー、エナメル、ファンデーション、リップスティック、おしろい、パック、軟膏、錠剤、注射液、顆粒、カプセル、香水、パウダー、オーデコロン、歯磨、石鹸、エアゾル、クレンジングフォーム等の他、皮膚老化防止改善剤、皮膚炎症防止改善剤、浴用剤、養毛剤、皮膚美容液、日焼け防止剤、色素性乾皮症・日光蕁麻疹等の光線過敏症の防止改善剤、光アレルギーの防止改善剤、光免疫抑制の防止改善剤あるいは、外傷・あかぎれ・ひびわれ等による肌荒れの防止改善剤、消毒剤、抗菌剤、殺虫剤、害虫駆除剤、角質溶解剤、表皮剥離剤、ニキビの防止改善剤、角化症・乾皮症・魚鱗癬・乾癬等の各種皮膚疾患の防止改善剤等に用いることができる。
更に組成物におけるその他の常用成分を、亜鉛を含有する組成物に本発明の効果を阻害しない範囲で添加することができる。組成物におけるその他の常用成分としては、防腐剤、褪色防止剤、緩衝剤、にきび用薬剤、ふけ・かゆみ防止剤、制汗防臭剤、熱傷用薬剤、抗ダニ・シラミ剤、角質軟化剤、乾皮症用薬剤、抗ウイルス剤、ホルモン類、ビタミン類、アミノ酸・ペプチド類、タンパク質類、収れん剤、清涼・刺激剤、動植物由来成分、抗生物質、抗真菌剤、育毛剤等を挙げることができる。Details of the present invention will be described below.
In the present invention, whitening means the concept that the skin is beautiful and white, and the whitening agent includes both for therapeutic purposes and for prevention purposes.
Zinc used in the present invention needs to be applied to the skin at a certain concentration in the form of zinc as a zinc salt from the viewpoint of skin irritation and introduction efficiency into cells. In this case, both an organic zinc salt and an inorganic zinc salt can be used. Examples of the organic zinc salt include pyrrolidone carboxylic acid zinc salt, gluconic acid zinc salt, sulfolime acid zinc salt, zinc lactate salt, various amino acid zinc salts, acylamino acid zinc salt and the like. Inorganic zinc includes zinc sulfate, zinc chloride, zinc oxide and the like.
As amino acid zinc salt, glycine zinc salt, alanine zinc salt, valine zinc salt, leucine zinc salt, isoleucine zinc salt, phenylalanine zinc salt, methionine zinc salt, tryptophan zinc salt, asparagine zinc salt, glutamine zinc salt, serine zinc salt, Examples include various amino acid zinc salts such as threonine zinc salt, cysteine zinc salt, tyrosine zinc salt, zinc aspartate, zinc glutamate, lysine zinc, arginine zinc, or histidine zinc.
The acylamino acid zinc salt is a zinc salt of a compound in which an acyl group is bonded to the amino group of the amino acid, and examples of the acylamino acid include compounds having the following structural formula.
In terms of enhancing the whitening effect, zinc salt of pyrrolidone carboxylic acid, which has an effect of promoting blood flow, is expected to collect useful substances such as ascorbic acid in the blood vessels at the application site, thus promoting the expression of ascorbate transporter It is a zinc salt whose effect is more remarkably reflected in the whitening effect.
The pyrrolidone carboxylic acid zinc salt is a zinc salt of 2-pyrrolidone-5-carboxylic acid and may be various hydrates. Hereinafter, it is also simply referred to as “PCA zinc salt” or “PCAZn salt”. In addition, the pyrrolidone carboxylic acid zinc salt used in the Examples is a dihydrate and has the following structure.
The whitening agent of the present invention is used by blending it with a composition such as a cosmetic or an external preparation for skin. At this time, the blending amount is 1 μM to 100 mM (0.000035 wt% to 3.5 wt% as PCA zinc salt), preferably 1 μM to 50 mM (0.000035 wt% to 0.35 wt% as PCA zinc salt). ), More preferably 1 μM to 10 mM (0.000035 wt% to 0.035 wt% as PCA zinc salt). In the case of many zinc salts, there is a problem in which a skin irritation feeling or a squeaky sensation occurs when the blending ratio is 3.5% by weight or more. A high concentration is not preferable because the desired effect does not occur.
When zinc is blended in cosmetics or skin external preparations, in addition to these components, components generally used as cosmetics or skin external preparations can be added within a range that does not impair the effects of the present invention.
Moreover, the further aspect of this invention is related with the composition by which zinc and the 1 type (s) or 2 or more types selected from the group which consists of ascorbic acid, N-acyl acidic amino acid ester, an amino acid, and an amino acid derivative are mix | blended simultaneously.
Especially, it is preferable from a viewpoint of a whitening effect to mix | blend about 5-600 mM ascorbic acid, Preferably about 5-300 mM simultaneously with zinc. In this case, ascorbic acid, various derivatives may be used as long as they can be incorporated into cosmetics. In other words, in addition to free forms of ascorbic acid and various salts (sodium ascorbate, sodium ascorbate-2-phosphate, magnesium ascorbate-2-magnesium phosphate, sodium ascorbate-2-sulfate, etc.), various glycosides (Such as ascorbyl-2-glucoside) and ascorbic acid ester (ascorbyl 6-stearate, ascorbyl 6-palmitate, ascorbyl 2,6-dipalmitate, ascorbyl 2,3,5,6-tetrahexyldecanoate, tocopheryl ascorbine Various derivatives such as acid may be used.
The N-acyl acidic amino acid ester used in the present invention is represented by the following structure.
N-acyl acidic diesters are particularly preferred, and suitable examples thereof include, for example, N-lauroyl glutamate di (cholesteryl behenyl octyldodecyl), N-lauroyl glutamate di (cholesteryl octyldodecyl), N-lauroyl glutamate di (phytosteryl 2) -Octyl dodecyl), N-lauroyl glutamate di (octyl dodecyl phytosteryl behenyl), and the like, which are available from Ajinomoto Co., Inc., respectively, "El Deu CL-301", "El Deu CL-202", "El Deu PS -203 "and" El Dew PS-304 ".
In the present invention, this N-acyl acidic amino acid ester contributes to improvement of moisturizing power and skin conditioning, and also contributes to improvement of stability. The amount is preferably 0.01% by weight or more, more preferably 0.1% by weight or more, further preferably 0.5% by weight or more, and the N-acyl acidic amino acid ester If the blending amount is increased more than necessary, stickiness may occur, so it is preferably 20% by weight or less, more preferably 10% by weight or less, and even more preferably 5% by weight or less.
An amino acid or an amino acid derivative is included in the composition to contribute to the improvement of the moisturizing effect. Examples of the amino acid include alanine, arginine, asparagine, aspartic acid, citrulline, cysteine, cystine, glutamine, glutamic acid, Glycine, histidine, oxyproline, isoleucine, leucine, lysine, methionine, ornithine, phenylalanine, proline, serine, threonine, tryptophan, tyrosine, valine, etc., and any of those L, D or DL forms It may also be a salt thereof. Examples of such salts include sodium salt, potassium salt, triethanolamine salt and the like.
Examples of amino acid derivatives include those obtained by cyclization, acylation or esterification of the above-mentioned amino acids, such as acetyl glutamic acid, acetyl methionine, acetyl cysteine, N, N-diacetyl-L-cystine dimethyl ester, acyl glutamic acid. Salts, acylglycine salts, acylalanine salts, acylarginine ethyl ester salts, and the like. However, N-acyl acidic amino acid ester is not included.
In addition to these components, components generally used as cosmetics or external preparations for skin can be added within a range that does not impair the effects of the present invention. Ingredients commonly used in cosmetics or skin external preparations include antioxidants, anti-inflammatory agents, UV absorbers, cell activators, moisturizers, metal chelators, oily raw materials, surfactants, solvents, polymers Substances, powder substances, pigments, fragrances, percutaneous absorption enhancers, steroid hormones, and the like.
There is no restriction | limiting in particular in the form of the said composition containing zinc, It can take arbitrary forms, such as solution form, paste form, gel form, solid form, and powder form. Further, the composition of the present invention comprises oil, lotion, cream, emulsion, gel, shampoo, hair rinse, hair conditioner, enamel, foundation, lipstick, funny, pack, ointment, tablet, injection solution, granule, capsule, perfume, Powder, eau de cologne, toothpaste, soap, aerosol, cleansing foam, etc., skin aging prevention improver, skin inflammation prevention improver, bath preparation, hair nourishing agent, skin beauty solution, sunscreen agent, xeroderma pigmentosum / Nikko urticaria Photosensitivity prevention and improvement agent, photoallergy prevention improvement agent, photoimmune suppression prevention improvement agent or skin roughening prevention and improvement agent such as trauma, scuffing and cracking, disinfectant, antibacterial agent, insecticide, pest control Agent, keratolytic agent, epidermis remover, acne prevention / amelioration agent, prevention of various skin diseases such as keratosis, psoriasis, ichthyosis and psoriasis It can be used to good agent.
Furthermore, other commonly used components in the composition can be added to the composition containing zinc as long as the effects of the present invention are not impaired. Other commonly used ingredients in the composition include preservatives, anti-fading agents, buffers, acne agents, anti-dandruff and itching agents, antiperspirant deodorants, burn agents, anti-ticks, lice agents, keratin softeners, Examples include dermatologic agents, antiviral agents, hormones, vitamins, amino acids / peptides, proteins, astringents, refreshing / stimulating agents, animal and plant derived components, antibiotics, antifungal agents, hair restorers, etc. .
以下、本発明を実施例（合成例、試験例および配合例）により更に具体的に説明するが、本発明はこれら実施例に限定されるものではない。尚、これらの実施例において、配合量は重量％で表した。
合成例 ピロリドンカルボン酸亜鉛塩の合成
ＤＬ−ＰＣＡ亜鉛塩は特開平３−１６８２４０号公報記載の方法に準じ、ＤＬ−ＰＣＡと酸化亜鉛を水中１００℃で２時間反応させた後、室温下５時間攪拌を続け、析出した結晶をろ別することにより合成した。Ｌ−ＰＣＡ亜鉛塩は以下の方法で合成した。オートクレーブ中にて、Ｌ−グルタミン酸ナトリウム１水和物（６１．１ｇ）の水溶液を１８０℃で２時間加熱し、５０ｗｔ％のピロリドンカルボン酸ナトリウム塩溶液を得た。５０ｗｔ％のピロリドンカルボン酸ナトリウム塩溶液１００．０ｇ（０．３３ｍｏｌ、ｐＨ７．７、光学純度８４％、Ｌ／Ｄ比率＝９２／８）に、硝酸（純度６０ｗｔ％）２．７ｇを添加し、ｐＨ５．２に調整した。硫酸亜鉛７水和物４７．６ｇ（０．１７ｍｏｌ）を水３４．２ｇに溶解した水溶液を、ピロリドンカルボン酸ナトリウム塩溶液（ｐＨ４．１）に添加した。この溶液を３０分間室温（ｐＨ３．７）で結晶を得るまで混和し、ろ過した。得られた結晶は水（２１．９ｇ）で洗浄し、３２．０ｇ（０．０９ｍｏｌ、収率５５％）のピロリドンカルボン酸亜鉛二水和物を得た。光学純度は９９．８％（Ｌ／Ｄ比率９９．９／０．１）であった。
試験例１ ピロリドンカルボン酸亜鉛塩のアスコルビン酸トランスポーターｍＲＮＡ発現増強効果
正常ヒト色素細胞をシャーレに正常ヒト色素細胞増殖用培地（クラボウ製）にて播種した。５％ＣＯ２、飽和水蒸気下、３７℃のインキュベータで１日、培養した。サンプルは正常色素細胞増殖用培地から添加している増殖因子を除いたもので調製した。シャーレにサンプル（ＰＣＡＺｎ塩など）１０μＭの濃度で調製した培地に交換し、インキュベータにて２４時間培養した。培養後、培地を吸引除去し、ＰＢＳでリンスした。細胞はＲＮｅａｓｙ Ｍｉｎｉ Ｋｉｔ（Ｑｕｉａｇｅｎ製）のプロトコールに従って、細胞内中のＲＮＡの抽出を行った。得られたＲＮＡから、定法に従いｃ−ＤＮＡを合成し、文献既知の方法にて（Ｃｈｒｉｓｔｏｐｈｅｒ Ｐ．Ｃｏｒｐｅ ｅｔｃ（２００５）Ｊ．Ｂｉｏｌ．Ｃｈｅｍ．２８０、５２１１−５２２０）、アスコルビン酸トランスポーター；ＳＶＣＴのＲＴ−ＰＣＲを行った（プライマー：センスプライマー；５’−ＣＴＧＡＧＣＴＣＡＴＧＧＣＧＡＴＣＴＡＣ−３’（配列番号１）、アンチセンス；５’−ＣＡＴＧＴＣＡＧＧＴＡＧＴＧＣＴＧＴＡＧＣＣＣＣＡ−３’（配列番号２））。得られたＤＮＡを電気泳動し、サンプルの有無によるＳＶＣＴのＲＮＡの発現量を評価した。電気泳動のバンドの評価は、ルミノ・イメージアナライザー（ＬＡＳ−３０００／富士フィルム製）を用い、Ｇ３ＰＤＨにて規格化した数値にて行った。
図１に示すように、ピロリドンカルボン酸亜鉛塩を１０μＭ添加することで、無添加のコントロールに比べ１０μＭ添加でＳＶＣＴは１４０％のＲＮＡ発現量の増加が確認された。これにより、ＮＨＥＭでのアスコルビン酸トランスポーターが増加し細胞内のアスコルビン酸濃度の増加、これに伴いＮＨＥＭのメラノソームでの酸化反応が抑制され、メラニン産生抑制効果が起こる。
試験例２ ＰＣＡＺｎ塩の血流促進効果
ＰＣＡＺｎ塩とその他のＺｎ塩との違いを血流促進効果（血液量増加）から確認した。各サンプルのＺｎ塩及び、Ｎａ塩を調製し、ヒト前腕に塗布し血流促進効果を目視にて評価した。サンプルは、▲１▼ＰＣＡＺｎ塩、▲２▼ＰＣＡＮａ塩、▲３▼グルコン酸Ｚｎ塩、▲４▼グルコン酸Ｎａ塩、▲５▼硫酸Ｚｎ塩、▲６▼硫酸Ｎａ２塩を用いた。濃度は５ｗｔ％とし、ｐＨは５．５〜６．５の間に調製した。上記サンプルを８０μｌ、前腕に半閉塞パッチし、３０分後パッチを除去し、目視評価を行った。さらに、３０分後、５０分後に目視観察を行い、表１に従い評点を付した。結果を表２に示す。結果は得られた評点の平均である。
これにより、血管内のアスコルビン酸などの有用物質を塗布部位に集めることで、ＰＣＡＺｎ塩はその他のＺｎ塩に比べ、より美白を高めることが期待される。
以下に、種々の製剤の配合例１〜１６を次に示す。これらの製剤は常法に従い調製した。尚、配合量は重量％で示した。
配合例１ 軟膏
Ｌ−ＰＣＡ亜鉛塩 ０．００１％
塩化ベンザルコニウム ０．１％
尿素 ２０．０％
白色ワセリン １５．０％
軽質流動パラフィン ６．０％
セタノール ３．０％
ステアリルアルコール ３．０％
モノステアリン酸グリセリル ５．０％
香料 適量
防腐剤 適量
緩衝剤 １．０％
精製水 残部
配合例２ 軟膏
グルコン酸亜鉛塩 ０．００２％
塩化ベンザルコニウム ０．１％
尿素 ２０．０％
白色ワセリン １５．０％
軽質流動パラフィン ６．０％
セタノール ３．０％
ステアリルアルコール ３．０％
モノステアリン酸グリセリル ５．０％
香料 適量
防腐剤 適量
緩衝剤 １．０％
精製水 残部
配合例３ 化粧水
Ｌ−ＰＣＡ亜鉛塩 ０．０３％
グリコール酸 ５．０％
グリセリン ３．０％
ソルビトール ２．０％
ポリオキシエチレン（２０）オレイルエーテル １．０％
エタノール １５．０％
パラフェノールスルホン酸亜鉛 ０．２％
緩衝剤 ０．１％
香料 ０．２％
防腐剤 適量
精製水 残部
配合例４ 化粧水
ＤＬ−ＰＣＡ亜鉛塩 ０．００５％
クエン酸 １．０％
尿素 ４．０％
サリチル酸 ２．０％
乳酸 ２．０％
グリセリン ２．０％
ベタイン ２．０％
ヒアルロン酸 ０．１％
エタノール １５．０％
緩衝剤 ０．１％
香料 ０．２％
防腐剤 適量
精製水 残部
配合例５ 化粧水
ＤＬ−ＰＣＡ亜鉛塩 ０．００５％
アスコルビン酸 １．０％
尿素 ４．０％
乳酸 ２．０％
グリセリン ２．０％
ベタイン ２．０％
ヒアルロン酸 ０．１％
エタノール １５．０％
緩衝剤 ０．１％
香料 ０．２％
防腐剤 適量
精製水 残部
配合例６ 化粧水
グリシン亜鉛塩 ０．００５％
クエン酸 １．０％
尿素 ４．０％
サリチル酸 ２．０％
乳酸 ２．０％
グリセリン ２．０％
ベタイン ２．０％
ヒアルロン酸 ０．１％
エタノール １５．０％
緩衝剤 ０．１％
香料 ０．２％
防腐剤 適量
精製水 残部
配合例７ ローション
Ｌ−ＰＣＡ亜鉛塩 ０．０１％
乳酸 ０．１％
フルーツ酸 ０．１％
グリセリン ４．０％
カオリン １．０％
カラミン ０．７％
カンフル ０．２％
エタノール １４．０％
香料 適量
精製水 残部
配合例８ ローション
Ｌ−ＰＣＡ亜鉛塩 ０．０１％
アスコルビン酸 ０．１％
フルーツ酸 ０．１％
グリセリン ４．０％
カオリン １．０％
カラミン ０．７％
カンフル ０．２％
エタノール １４．０％
香料 適量
精製水 残部
配合例９ ローション
塩化亜鉛塩 ０．００５％
乳酸 ０．１％
フルーツ酸 ０．１％
グリセリン ４．０％
カオリン １．０％
カラミン ０．７％
カンフル ０．２％
エタノール １４．０％
香料 適量
精製水 残部
配合例１０ クリーム
Ｌ−ＰＣＡ亜鉛塩 ０．０１％
レゾルシノール ０．１％
コウジ酸 １．０％
ステアリン酸 ２．０％
ポリオキシエチレン（２５）セチルエーテル ３．０％
モノステアリン酸グリセリル ２．０％
オクチルドデカノール １０．０％
セタノール ６．０％
還元ラノリン ４．０％
スクワラン ９．０％
１，３−ブチレングリコール ６．０％
ポリエチレングリコール（１５００） ４．０％
防腐剤 適量
香料 適量
精製水 残部
配合例１１ クリーム
グルコン酸亜鉛塩 ０．０２％
レゾルシノール ０．１％
コウジ酸 １．０％
ステアリン酸 ２．０％
ポリオキシエチレン（２５）セチルエーテル ３．０％
モノステアリン酸グリセリル ２．０％
オクチルドデカノール １０．０％
セタノール ６．０％
還元ラノリン ４．０％
スクワラン ９．０％
１，３−ブチレングリコール ６．０％
ポリエチレングリコール（１５００） ４．０％
防腐剤 適量
香料 適量
精製水 残部
配合例１２ クリーム
グルコン酸亜鉛塩 ０．０２％
レゾルシノール ０．１％
アスコルビン酸 ５．０％
ステアリン酸 ２．０％
ポリオキシエチレン（２５）セチルエーテル ３．０％
モノステアリン酸グリセリル ２．０％
オクチルドデカノール １０．０％
セタノール ６．０％
還元ラノリン ４．０％
スクワラン ９．０％
１，３−ブチレングリコール ６．０％
ポリエチレングリコール（１５００） ４．０％
防腐剤 適量
香料 適量
精製水 残部
配合例１３ クリーム
ＤＬ−ＰＣＡ亜鉛塩 ０．０１％
グリコール酸 ２．０％
固形パラフィン ５．０％
ミツロウ １０．０％
ワセリン １５．０％
流動パラフィン ４１．０％
１，３−ブチレングリコール ４．０％
モノステアリン酸グリセリン ２．０％
モノラウリン酸ポリオキシエチレンソルビタン（２０） ２．０％
ホウ砂 ０．２％
防腐剤 適量
香料 適量
酸化防止剤 適量
精製水 残部
配合例１４ 乳液
Ｌ−ＰＣＡ亜鉛塩 ０．０２％
乳酸 ２．０％
ステアリルアルコール ０．５％
硬化パーム油 ３．０％
流動パラフィン ３５．０％
ジプロピレングリコール ６．０％
ポリエチレングリコール（４００） ４．０％
セスキオレイン酸ソルビタン １．６％
ポリオキシエチレン（２０）オレイルエーテル ２．４％
カルボキシビニルポリマー １．５％
水酸化カリウム ０．１％
キレート剤 適量
防腐剤 適量
香料 適量
精製水 残部
配合例１５ 乳液
硫酸亜鉛塩 ０．０１％
乳酸 ２．０％
ステアリルアルコール ０．５％
硬化パーム油 ３．０％
流動パラフィン ３５．０％
ジプロピレングリコール ６．０％
ポリエチレングリコール（４００） ４．０％
セスキオレイン酸ソルビタン １．６％
ポリオキシエチレン（２０）オレイルエーテル ２．４％
カルボキシビニルポリマー １．５％
水酸化カリウム ０．１％
キレート剤 適量
防腐剤 適量
香料 適量
精製水 残部
配合例１６ 美容液
Ｌ−ＰＣＡ亜鉛塩 ０．０５％
フルーツ酸 ０．５％
ジプロピレングリコール ５．０％
ポリエチレングリコール（４００） ５．０％
エタノール １０．０％
カルボキシビニルポリマー ０．５％
アルギン酸ナトリウム ０．５％
水酸化カリウム ０．２％
モノステアリン酸ポリオキシエチレン（２０）ソルビタン １．０％
モノオレイン酸ソルビット ０．５％
オレイルアルコール ０．５％
プラセンタエキス ０．２％
酢酸ｄｌ−α−トコフェロール ０．２％
香料 適量
防腐剤 適量
褪色防止剤 適量
精製水 残部
配合例１７ 美容液
Ｌ−ＰＣＡ亜鉛塩 ０．０５％
アスコルビン酸 ２．０％
ジプロピレングリコール ５．０％
ポリエチレングリコール（４００） ５．０％
エタノール １０．０％
カルボキシビニルポリマー ０．５％
アルギン酸ナトリウム ０．５％
水酸化カリウム ０．２％
モノステアリン酸ポリオキシエチレン（２０）ソルビタン １．０％
モノオレイン酸ソルビット ０．５％
オレイルアルコール ０．５％
プラセンタエキス ０．２％
酢酸ｄｌ−α−トコフェロール ０．２％
香料 適量
防腐剤 適量
褪色防止剤 適量
精製水残部
配合例１８ 美容液
乳酸亜鉛塩 ０．００５％
フルーツ酸 ０．５％
ジプロピレングリコール ５．０％
ポリエチレングリコール（４００） ５．０％
エタノール １０．０％
カルボキシビニルポリマー ０．５％
アルギン酸ナトリウム ０．５％
水酸化カリウム ０．２％
モノステアリン酸ポリオキシエチレン（２０）ソルビタン １．０％
モノオレイン酸ソルビット ０．５％
オレイルアルコール ０．５％
プラセンタエキス ０．２％
酢酸ｄｌ−α−トコフェロール ０．２％
香料 適量
防腐剤 適量
褪色防止剤 適量
精製水 残部
配合例１９ パック
ＤＬ−ＰＣＡ亜鉛塩 ０．０３％
イソプロパノール ２．０％
ポリビニルアルコール １５．０％
カルボキシメチルセルロース ５．０％
１，３−ブチレングリコール ５．０％
エタノール １２．０％
ポリオキシエチレン（２０）オレイルエーテル ０．５％
香料 適量
防腐剤 適量
緩衝剤 適量
精製水 残部
配合例２０ パック
グルコン酸亜鉛塩 ０．０３％
イソプロパノール ２．０％
ポリビニルアルコール １５．０％
カルボキシメチルセルロース ５．０％
１，３−ブチレングリコール ５．０％
エタノール １２．０％
ポリオキシエチレン（２０）オレイルエーテル ０．５％
香料 適量
防腐剤 適量
緩衝剤 適量
精製水 残部
配合例２１ ファンデーション
ＤＬ−ＰＣＡ亜鉛塩 ０．１％
サリチル酸 ０．５％
流動パラフィン １０．０％
モノオレイン酸ポリオキシエチレン（２０）ソルビタン ３．５％
プロピレングリコール ３．０％
酸化チタン ９．０％
カオリン ２４．０％
タルク ４２．０％
着色顔料 ３．０％
香料 適量
防腐剤 適量
酸化防止剤 適量
配合例２２ 液体ハンドソープ
Ｌ−ＰＣＡ亜鉛塩 ０．１％
ラウリル硫酸ナトリウム ３０．０％
ベタイン ３．０％
グリセリン脂肪酸エステル １．０％
フェノキシエタノール １．０％
ＥＤＴＡ ０．１％
精製水 残部EXAMPLES Hereinafter, although an Example (synthesis example, a test example, and a compounding example) demonstrates this invention further more concretely, this invention is not limited to these Examples. In these examples, the blending amount was expressed in wt%.
Synthesis Example Synthesis of Pyrrolidone Carboxylic Acid Zinc Salt DL-PCA zinc salt is prepared by reacting DL-PCA and zinc oxide in water at 100 ° C. for 2 hours in accordance with the method described in JP-A-3-168240, and then at room temperature for 5 hours. The stirring was continued and the precipitated crystals were separated by filtration. L-PCA zinc salt was synthesized by the following method. In an autoclave, an aqueous solution of sodium L-glutamate monohydrate (61.1 g) was heated at 180 ° C. for 2 hours to obtain a 50 wt% pyrrolidonecarboxylic acid sodium salt solution. To 100.0 g (0.33 mol, pH 7.7, optical purity 84%, L / D ratio = 92/8) of 50 wt% pyrrolidone carboxylic acid sodium salt solution, 2.7 g of nitric acid (
Test Example 1 Ascorbic Acid Transporter mRNA Expression Enhancement Effect of Pyrrolidone Carboxylic Acid Zinc Salt Normal human pigment cells were seeded on a petri dish in a normal human pigment cell growth medium (manufactured by Kurabo Industries). The cells were cultured in an incubator at 37 ° C. for 1 day under 5% CO 2 and saturated steam. The sample was prepared by removing the growth factor added from the normal pigment cell growth medium. The culture medium was replaced with a medium prepared with a sample (PCAZn salt, etc.) at a concentration of 10 μM, and cultured in an incubator for 24 hours. After culturing, the medium was removed by suction and rinsed with PBS. The cells were extracted from RNA in the cells according to the protocol of RNeasy Mini Kit (manufactured by Qiagen). From the obtained RNA, c-DNA was synthesized according to a conventional method, and a method known in the literature (Christopher P. Corp et c (2005) J. Biol. Chem. 280, 5211-5220), ascorbic acid transporter; SVCT RT-PCR was performed (primer: sense primer; 5'-CTGAGCTCATGGCGATTAC-3 '(SEQ ID NO: 1), antisense; 5'-CATGTCAGGTAGTGCTGTTAGCCCCA-3' (SEQ ID NO: 2)). The obtained DNA was electrophoresed to evaluate the expression level of SVCT RNA depending on the presence or absence of the sample. The evaluation of the band of electrophoresis was performed using a numerical value standardized by G3PDH using a lumino image analyzer (LAS-3000 / manufactured by Fuji Film).
As shown in FIG. 1, by adding 10 μM pyrrolidone carboxylic acid zinc salt, SVCT increased 140% in RNA expression level when added at 10 μM compared to the control without addition. As a result, the ascorbic acid transporter in NHEM increases to increase the intracellular ascorbic acid concentration, and accordingly, the oxidation reaction of NHEM in melanosomes is suppressed, and the melanin production suppressing effect occurs.
Test Example 2 Blood Flow Promoting Effect of PCAZn Salt The difference between the PCAZn salt and other Zn salts was confirmed from the blood flow promoting effect (blood volume increase). The Zn salt and Na salt of each sample were prepared and applied to a human forearm to visually evaluate the blood flow promoting effect. Samples were (1) PCAZn salt, (2) PCANA salt, (3) Zn gluconate, (4) Na gluconate, (5) Zn sulfate, and (6) Na 2 sulfate. The concentration was 5 wt%, and the pH was adjusted between 5.5 and 6.5. 80 μl of the sample was semi-occluded patched on the forearm, 30 minutes later, the patch was removed, and visual evaluation was performed. Further, visual observation was performed after 30 minutes and after 50 minutes, and a score was assigned according to Table 1. The results are shown in Table 2. The result is the average of the scores obtained.
Thereby, PCAZn salt is expected to enhance whitening more than other Zn salts by collecting useful substances such as ascorbic acid in blood vessels at the application site.
Hereinafter, Formulation Examples 1 to 16 of various preparations are shown below. These preparations were prepared according to a conventional method. In addition, the compounding quantity was shown by weight%.
Formulation Example 1 Ointment L-PCA Zinc Salt 0.001%
Benzalkonium chloride 0.1%
Urea 20.0%
White petrolatum 15.0%
Light liquid paraffin 6.0%
Cetanol 3.0%
Stearyl alcohol 3.0%
Glyceryl monostearate 5.0%
Perfume Appropriate amount Preservative Appropriate amount Buffer 1.0%
Purified water balance
Formulation Example 2 Ointment Zinc gluconate 0.002%
Benzalkonium chloride 0.1%
Urea 20.0%
White petrolatum 15.0%
Light liquid paraffin 6.0%
Cetanol 3.0%
Stearyl alcohol 3.0%
Glyceryl monostearate 5.0%
Perfume Appropriate amount Preservative Appropriate amount Buffer 1.0%
Purified water balance
Formulation Example 3 Lotion L-PCA Zinc Salt 0.03%
Glycolic acid 5.0%
Glycerol 3.0%
Sorbitol 2.0%
Polyoxyethylene (20) oleyl ether 1.0%
Ethanol 15.0%
Zinc paraphenol sulfonate 0.2%
Buffer 0.1%
Fragrance 0.2%
Preservative Appropriate amount of purified water balance
Formulation Example 4 Lotion DL-PCA zinc salt 0.005%
Citric acid 1.0%
Urea 4.0%
Salicylic acid 2.0%
Lactic acid 2.0%
Glycerin 2.0%
Betaine 2.0%
Hyaluronic acid 0.1%
Ethanol 15.0%
Buffer 0.1%
Fragrance 0.2%
Preservative Appropriate amount of purified water balance
Formulation Example 5 Lotion DL-PCA zinc salt 0.005%
Ascorbic acid 1.0%
Urea 4.0%
Lactic acid 2.0%
Glycerin 2.0%
Betaine 2.0%
Hyaluronic acid 0.1%
Ethanol 15.0%
Buffer 0.1%
Fragrance 0.2%
Preservative Appropriate amount of purified water balance
Formulation Example 6 Lotion Lotion Glycine zinc salt 0.005%
Citric acid 1.0%
Urea 4.0%
Salicylic acid 2.0%
Lactic acid 2.0%
Glycerin 2.0%
Betaine 2.0%
Hyaluronic acid 0.1%
Ethanol 15.0%
Buffer 0.1%
Fragrance 0.2%
Preservative Appropriate amount of purified water balance
Formulation Example 7 Lotion L-PCA zinc salt 0.01%
Lactic acid 0.1%
Fruit acid 0.1%
Glycerin 4.0%
Kaolin 1.0%
Calamine 0.7%
Canful 0.2%
Ethanol 14.0%
Perfume appropriate amount purified water balance
Formulation Example 8 Lotion L-PCA zinc salt 0.01%
Ascorbic acid 0.1%
Fruit acid 0.1%
Glycerin 4.0%
Kaolin 1.0%
Calamine 0.7%
Canful 0.2%
Ethanol 14.0%
Perfume appropriate amount purified water balance
Formulation Example 9 Lotion Zinc chloride salt 0.005%
Lactic acid 0.1%
Fruit acid 0.1%
Glycerin 4.0%
Kaolin 1.0%
Calamine 0.7%
Canful 0.2%
Ethanol 14.0%
Perfume Appropriate amount of purified water balance
Formulation Example 10 Cream L-PCA zinc salt 0.01%
Resorcinol 0.1%
Kojic acid 1.0%
Stearic acid 2.0%
Polyoxyethylene (25) cetyl ether 3.0%
Glyceryl monostearate 2.0%
Octyldodecanol 10.0%
Cetanol 6.0%
Reduced lanolin 4.0%
Squalane 9.0%
1,3-butylene glycol 6.0%
Polyethylene glycol (1500) 4.0%
Preservative Appropriate amount of perfume Appropriate amount of purified water The remainder
Formulation Example 11 Cream Zinc gluconate 0.02%
Resorcinol 0.1%
Kojic acid 1.0%
Stearic acid 2.0%
Polyoxyethylene (25) cetyl ether 3.0%
Glyceryl monostearate 2.0%
Octyldodecanol 10.0%
Cetanol 6.0%
Reduced lanolin 4.0%
Squalane 9.0%
1,3-butylene glycol 6.0%
Polyethylene glycol (1500) 4.0%
Preservative Appropriate amount of perfume Appropriate amount of purified water The remainder
Formulation Example 12 Cream Zinc gluconate 0.02%
Resorcinol 0.1%
Ascorbic acid 5.0%
Stearic acid 2.0%
Polyoxyethylene (25) cetyl ether 3.0%
Glyceryl monostearate 2.0%
Octyldodecanol 10.0%
Cetanol 6.0%
Reduced lanolin 4.0%
Squalane 9.0%
1,3-butylene glycol 6.0%
Polyethylene glycol (1500) 4.0%
Preservative Appropriate amount of perfume Appropriate amount of purified water The remainder
Formulation Example 13 Cream DL-PCA zinc salt 0.01%
Glycolic acid 2.0%
Solid paraffin 5.0%
Beeslow 10.0%
Vaseline 15.0%
Liquid paraffin 41.0%
1,3-butylene glycol 4.0%
Glycerol monostearate 2.0%
Polyoxyethylene sorbitan monolaurate (20) 2.0%
Borax 0.2%
Preservative Appropriate amount of perfume Appropriate amount Antioxidant Appropriate amount of purified water Remainder
Formulation Example 14 Latex L-PCA zinc salt 0.02%
Lactic acid 2.0%
Stearyl alcohol 0.5%
Hardened palm oil 3.0%
Liquid paraffin 35.0%
Dipropylene glycol 6.0%
Polyethylene glycol (400) 4.0%
Sorbitan sesquioleate 1.6%
Polyoxyethylene (20) oleyl ether 2.4%
Carboxyvinyl polymer 1.5%
Potassium hydroxide 0.1%
Chelating agent appropriate amount preservative appropriate amount perfume appropriate amount purified water balance
Formulation Example 15 Latex Zinc sulfate 0.01%
Lactic acid 2.0%
Stearyl alcohol 0.5%
Hardened palm oil 3.0%
Liquid paraffin 35.0%
Dipropylene glycol 6.0%
Polyethylene glycol (400) 4.0%
Sorbitan sesquioleate 1.6%
Polyoxyethylene (20) oleyl ether 2.4%
Carboxyvinyl polymer 1.5%
Potassium hydroxide 0.1%
Chelating agent appropriate amount preservative appropriate amount perfume appropriate amount purified water balance
Formulation Example 16 Cosmetic liquid L-PCA zinc salt 0.05%
Fruit acid 0.5%
Dipropylene glycol 5.0%
Polyethylene glycol (400) 5.0%
Ethanol 10.0%
Carboxy vinyl polymer 0.5%
Sodium alginate 0.5%
Potassium hydroxide 0.2%
Polystearic acid polyoxyethylene (20) sorbitan 1.0%
Sorbit monooleate 0.5%
Oleyl alcohol 0.5%
Placenta extract 0.2%
Dl-α-tocopherol acetate 0.2%
Perfume Appropriate amount Preservative Appropriate amount Anti-fading agent Appropriate amount of purified water balance
Formulation Example 17 Cosmetic liquid L-PCA zinc salt 0.05%
Ascorbic acid 2.0%
Dipropylene glycol 5.0%
Polyethylene glycol (400) 5.0%
Ethanol 10.0%
Carboxy vinyl polymer 0.5%
Sodium alginate 0.5%
Potassium hydroxide 0.2%
Polystearic acid polyoxyethylene (20) sorbitan 1.0%
Sorbit monooleate 0.5%
Oleyl alcohol 0.5%
Placenta extract 0.2%
Dl-α-tocopherol acetate 0.2%
Perfume Appropriate amount Preservative Appropriate amount Anti-fading agent Appropriate amount Purified water balance
Formulation Example 18 Cosmetic liquid <br/> Zinc lactate salt 0.005%
Fruit acid 0.5%
Dipropylene glycol 5.0%
Polyethylene glycol (400) 5.0%
Ethanol 10.0%
Carboxy vinyl polymer 0.5%
Sodium alginate 0.5%
Potassium hydroxide 0.2%
Polystearic acid polyoxyethylene (20) sorbitan 1.0%
Sorbit monooleate 0.5%
Oleyl alcohol 0.5%
Placenta extract 0.2%
Dl-α-tocopherol acetate 0.2%
Perfume Appropriate amount Preservative Appropriate amount Anti-fading agent Appropriate amount of purified water balance
Formulation Example 19 Pack DL-PCA zinc salt 0.03%
Isopropanol 2.0%
Polyvinyl alcohol 15.0%
Carboxymethylcellulose 5.0%
1,3-butylene glycol 5.0%
Ethanol 12.0%
Polyoxyethylene (20) oleyl ether 0.5%
Perfume Appropriate amount Preservative Appropriate amount Buffer agent Appropriate amount of purified water Remainder
Formulation Example 20 Pack Zinc gluconate 0.03%
Isopropanol 2.0%
Polyvinyl alcohol 15.0%
Carboxymethylcellulose 5.0%
1,3-butylene glycol 5.0%
Ethanol 12.0%
Polyoxyethylene (20) oleyl ether 0.5%
Perfume Appropriate amount Preservative Appropriate amount Buffer agent Appropriate amount of purified water Remainder
Formulation Example 21 Foundation DL-PCA zinc salt 0.1%
Salicylic acid 0.5%
Liquid paraffin 10.0%
Polyoxyethylene (20) sorbitan monooleate 3.5%
Propylene glycol 3.0%
Titanium oxide 9.0%
Kaolin 24.0%
Talc 42.0%
Color pigment 3.0%
Perfume Appropriate amount Preservative Appropriate amount
Formulation Example 22 Liquid Hand Soap L-PCA Zinc Salt 0.1%
Sodium lauryl sulfate 30.0%
Betaine 3.0%
Glycerin fatty acid ester 1.0%
Phenoxyethanol 1.0%
EDTA 0.1%
Purified water balance
本発明は、化粧品の分野において利用可能である。
［配列表］
[Sequence Listing]
Claims (4)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2008522638A JP5552741B2 (en) | 2006-06-23 | 2007-06-21 | Whitening agent containing zinc as an active ingredient |
Applications Claiming Priority (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2006173918 | 2006-06-23 | ||
| JP2006173918 | 2006-06-23 | ||
| JP2006223941 | 2006-08-21 | ||
| JP2006223941 | 2006-08-21 | ||
| US86649906P | 2006-11-20 | 2006-11-20 | |
| US86650306P | 2006-11-20 | 2006-11-20 | |
| US60/866,503 | 2006-11-20 | ||
| US60/866,499 | 2006-11-20 | ||
| JP2006329172 | 2006-12-06 | ||
| JP2006329172 | 2006-12-06 | ||
| US87184506P | 2006-12-26 | 2006-12-26 | |
| US60/871,845 | 2006-12-26 | ||
| JP2008522638A JP5552741B2 (en) | 2006-06-23 | 2007-06-21 | Whitening agent containing zinc as an active ingredient |
| PCT/JP2007/063051 WO2007148832A1 (en) | 2006-06-23 | 2007-06-21 | Skin whitening agent containing zinc as active ingredient |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPWO2007148832A1 JPWO2007148832A1 (en) | 2009-11-19 |
| JP5552741B2 true JP5552741B2 (en) | 2014-07-16 |
Family
ID=44766892
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008522638A Active JP5552741B2 (en) | 2006-06-23 | 2007-06-21 | Whitening agent containing zinc as an active ingredient |
| JP2008522615A Active JP5423002B2 (en) | 2006-06-23 | 2007-06-21 | Collagen synthesis promoter containing zinc as an active ingredient |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008522615A Active JP5423002B2 (en) | 2006-06-23 | 2007-06-21 | Collagen synthesis promoter containing zinc as an active ingredient |
Country Status (2)
| Country | Link |
|---|---|
| JP (2) | JP5552741B2 (en) |
| TW (2) | TW200808365A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3192493B1 (en) | 2014-09-10 | 2023-07-12 | Ajinomoto Co., Inc. | Moisturizer and cosmetic containing same |
| CN113491654A (en) * | 2020-04-07 | 2021-10-12 | 美特瑞生物科技(上海)有限公司 | Formula of whitening skin care product |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993014748A1 (en) * | 1992-02-03 | 1993-08-05 | Otsuka Pharmaceutical Co., Ltd. | Remedy for dermatopathy and metallothionein inducer |
| JPH09301846A (en) * | 1996-03-15 | 1997-11-25 | Shiseido Co Ltd | Aqueous thickened gel-like composition and liquid water in oil type emulsified composition |
| JP2002167319A (en) * | 2000-09-22 | 2002-06-11 | Asahi Kasei Corp | Bleaching cosmetic |
| JP2005023042A (en) * | 2003-07-04 | 2005-01-27 | Noevir Co Ltd | External preparation for skin |
| JP2006016401A (en) * | 2005-07-12 | 2006-01-19 | Noevir Co Ltd | Dermatologic preparation for external use and method for promoting permeation of bleaching agent by using the same |
| JP2006022090A (en) * | 2004-06-08 | 2006-01-26 | Ajinomoto Co Inc | Inflammation inhibitor composed of pyrrolidonecarboxylic acid zinc salt |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58180410A (en) * | 1982-04-16 | 1983-10-21 | Shiseido Co Ltd | Cosmetic |
| FR2697161B1 (en) * | 1992-10-26 | 1995-01-13 | Jouvance Daniel | Cosmetic product with stabilized redox potential. |
| DE4410238A1 (en) * | 1994-03-25 | 1995-09-28 | Beiersdorf Ag | Skin care products |
| US6066327A (en) * | 1997-12-17 | 2000-05-23 | Color Access, Inc. | Antioxidant mixture |
| JPH11189522A (en) * | 1997-12-25 | 1999-07-13 | Ajinomoto Co Inc | Cosmetic and skin preparation for external use |
| JP2000355516A (en) * | 1999-06-14 | 2000-12-26 | Ajinomoto Co Inc | New composition for cosmetic |
| JP4577996B2 (en) * | 2001-01-18 | 2010-11-10 | 株式会社ノエビア | Skin cosmetics |
| DE60211581D1 (en) * | 2001-03-23 | 2006-06-29 | Oreal | Skin treatment agent containing fibers and ubiquinones |
| JP2003277219A (en) * | 2002-03-20 | 2003-10-02 | Sukoyaka Shokuhin Kk | Process for enhancing improving effects of cosmetic vegetable oil and cream on skin condition such as improving effects on wrinkle and pigmented spot and enhancing effects on senile wart and mole |
| JP4377263B2 (en) * | 2004-03-03 | 2009-12-02 | 日光ケミカルズ株式会社 | Cosmetics and external preparation for skin |
-
2007
- 2007-06-21 JP JP2008522638A patent/JP5552741B2/en active Active
- 2007-06-21 TW TW96122284A patent/TW200808365A/en unknown
- 2007-06-21 TW TW96122286A patent/TW200808717A/en unknown
- 2007-06-21 JP JP2008522615A patent/JP5423002B2/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993014748A1 (en) * | 1992-02-03 | 1993-08-05 | Otsuka Pharmaceutical Co., Ltd. | Remedy for dermatopathy and metallothionein inducer |
| JPH09301846A (en) * | 1996-03-15 | 1997-11-25 | Shiseido Co Ltd | Aqueous thickened gel-like composition and liquid water in oil type emulsified composition |
| JP2002167319A (en) * | 2000-09-22 | 2002-06-11 | Asahi Kasei Corp | Bleaching cosmetic |
| JP2005023042A (en) * | 2003-07-04 | 2005-01-27 | Noevir Co Ltd | External preparation for skin |
| JP2006022090A (en) * | 2004-06-08 | 2006-01-26 | Ajinomoto Co Inc | Inflammation inhibitor composed of pyrrolidonecarboxylic acid zinc salt |
| JP2006016401A (en) * | 2005-07-12 | 2006-01-19 | Noevir Co Ltd | Dermatologic preparation for external use and method for promoting permeation of bleaching agent by using the same |
Also Published As
| Publication number | Publication date |
|---|---|
| JPWO2007148831A1 (en) | 2009-11-19 |
| TW200808717A (en) | 2008-02-16 |
| TW200808365A (en) | 2008-02-16 |
| JPWO2007148832A1 (en) | 2009-11-19 |
| JP5423002B2 (en) | 2014-02-19 |
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