JP5399701B2 - Whitening skin external preparation and skin whitening method - Google Patents

Whitening skin external preparation and skin whitening method Download PDF

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JP5399701B2
JP5399701B2 JP2008505150A JP2008505150A JP5399701B2 JP 5399701 B2 JP5399701 B2 JP 5399701B2 JP 2008505150 A JP2008505150 A JP 2008505150A JP 2008505150 A JP2008505150 A JP 2008505150A JP 5399701 B2 JP5399701 B2 JP 5399701B2
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祐子 福島
研 板倉
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • A61Q19/02Preparations for care of the skin for chemically bleaching or whitening the skin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/70Carbohydrates; Sugars; Derivatives thereof
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60Sugars; Derivatives thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61P17/00Drugs for dermatological disorders
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • A61P17/16Emollients or protectives, e.g. against radiation
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

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Description

本発明は、新規な美白用皮膚外用剤及び皮膚の美白方法に関する。   The present invention relates to a novel skin external preparation for whitening and a skin whitening method.

従来、高級脂肪酸のエステル類は、系の安定化に寄与する剤、例えば、界面活性剤等として、皮膚外用剤に広く使用されている。例えば、製剤安定性の向上を目的として、脂肪酸エステル類が配合された皮膚外用剤が提案されている(特許文献1)。また、炭素数12〜22の飽和もしくは不飽和脂肪酸を含むショ糖エステル型の非イオン界面活性剤を膜の成分として含有する活性成分担体が開示され、化粧品への利用も提案されている(特許文献2)。
また、高級脂肪酸及びその誘導体等そのものを、美白剤等の有効成分として皮膚外用剤に配合することも提案され、例えば、炭素数18〜22で、且つ分子構造中の不飽和数が2以上のリノール酸等の脂肪酸、その塩、又はその一価もしくは二価アルコールとのエステルを活性成分として含有する美白化粧料が提案されている(特許文献3)。また、リノール酸等の脂肪酸等と、甘草から抽出された油溶性エキスとを含有する美白化粧料(特許文献4)が提案されている。
特開平9−294927号公報 特許第3414752号公報 特開昭63−284109号公報 特開平5−194176号公報
Conventionally, esters of higher fatty acids have been widely used in skin external preparations as agents that contribute to the stabilization of the system, such as surfactants. For example, an external preparation for skin containing fatty acid esters has been proposed for the purpose of improving formulation stability (Patent Document 1). Further, an active ingredient carrier containing a sucrose ester type nonionic surfactant containing a saturated or unsaturated fatty acid having 12 to 22 carbon atoms as a component of a film is disclosed, and its use in cosmetics is also proposed (patent) Reference 2).
In addition, it has also been proposed to blend higher fatty acids and derivatives thereof as active ingredients such as whitening agents into an external preparation for skin, for example, having 18 to 22 carbon atoms and an unsaturated number of 2 or more in the molecular structure. Whitening cosmetics containing fatty acids such as linoleic acid, salts thereof, or esters thereof with mono- or dihydric alcohols as active ingredients have been proposed (Patent Document 3). Moreover, whitening cosmetics (patent document 4) containing fatty acids such as linoleic acid and an oil-soluble extract extracted from licorice have been proposed.
Japanese Patent Laid-Open No. 9-294927 Japanese Patent No. 3414752 JP 63-284109 A JP-A-5-194176

しかし、リノール酸、その塩又はそのアルコールとのエステルを実際に皮膚外用剤に配合すると、経時で変臭・変色を起こし易く、保存安定性の点で問題がある。
従って、本発明は、経時における変臭・変色がなく(もしくは少なく)、保存安定性が良好であるとともに、リノール酸を配合した場合と同様の優れた美白効果を奏する皮膚外用剤を提供することを課題とする。
However, when linoleic acid, a salt thereof or an ester thereof with alcohol is actually added to the external preparation for skin, odor and discoloration are likely to occur over time, and there is a problem in terms of storage stability.
Accordingly, the present invention provides an external preparation for skin that has no (or less) odor and discoloration over time, has good storage stability, and exhibits the same whitening effect as when linoleic acid is blended. Is an issue.

本発明者らは、リノール酸と同様の優れた美白効果を奏する化合物を探索した結果、ショ糖とリノール酸とがエステル結合したショ糖リノール酸エステルは、リノール酸と同様の優れた美白効果を奏することを見出した。さらに、ショ糖リノール酸エステルは、遊離脂肪酸よりも格段に経皮吸収効果が高く、且つ製剤中での安定性にも優れているとの知見を得、これらの知見に基づいてさらに検討を重ね、本発明を完成した。
即ち、本発明は、上記課題を解決するため、ショ糖リノール酸エステルを有効成分として含有する美白用皮膚外用剤を提供する。
As a result of searching for a compound having an excellent whitening effect similar to linoleic acid, the present inventors have found that sucrose linoleic acid ester in which sucrose and linoleic acid are ester-bonded has an excellent whitening effect similar to linoleic acid. I found out to play. In addition, sucrose linoleic acid ester has obtained the knowledge that it has a much higher transdermal absorption effect than free fatty acids and is also excellent in stability in the preparation, and further studies are made based on these findings. The present invention has been completed.
That is, this invention provides the skin external preparation for whitening which contains a sucrose linoleic acid ester as an active ingredient in order to solve the said subject.

本発明の皮膚外用剤に用いられる前記ショ糖リノール酸エステルの1分子中のエステル結合の数については、特に制限されず、モノエステル体、ジエステル体、及びトリ、テトラ又はそれ以上の複数のエステル結合を有するポリエステル体(以下、3以上のエステル結合を含むエステル体を「ポリエステル体」という場合がある)のいずれであってもよく、またこれらから選択される2種以上の混合物であってもよい。本発明の好ましい態様として、前記ショ糖リノール酸エステルが、ジエステル体を20質量%以上含む前記美白用皮膚外用剤;前記ショ糖リノール酸エステルが、モノエステル体を20質量%以上含む前記美白用皮膚外用剤;ならびに前記ショ糖リノール酸エステルが、ジエステル体を20質量%以上、及びモノエステル体を20質量%以上含む前記美白用皮膚外用剤;が提供される。   The number of ester bonds in one molecule of the sucrose linoleic acid ester used in the external preparation for skin of the present invention is not particularly limited, and is a monoester, a diester, and a plurality of tri, tetra, or more esters. Any of polyester bodies having a bond (hereinafter, an ester body containing 3 or more ester bonds may be referred to as “polyester body”), or a mixture of two or more selected from these. Good. As a preferred embodiment of the present invention, the sucrose linoleic acid ester contains 20% by mass or more of a diester, and the skin whitening agent for whitening; the sucrose linoleic acid ester contains 20% by mass or more of a monoester. And a skin external preparation for skin whitening, wherein the sucrose linoleic acid ester contains 20% by mass or more of a diester and 20% by mass or more of a monoester.

また、本発明の美白用皮膚外用剤は、さらに、ショ糖リノール酸エステル以外の美白剤の少なくとも一種を含有しているのが好ましく、前記美白剤が、アスコルビン酸及びその誘導体、アルブチン並びにエラグ酸から選ばれる少なくとも一種であるのが好ましい。
また、別の観点から、本発明によって、ショ糖リノール酸エステルを有効成分として用いる皮膚の美白方法;及びショ糖リノール酸エステルを添加することを含む美白用化粧料の製造方法;が提供される。
Further, the skin whitening external preparation of the present invention preferably further contains at least one whitening agent other than sucrose linoleic acid ester, and the whitening agent is ascorbic acid and its derivatives, arbutin and ellagic acid. It is preferably at least one selected from
In another aspect, the present invention provides a skin whitening method using sucrose linoleic acid ester as an active ingredient; and a method for producing a whitening cosmetic comprising adding sucrose linoleic acid ester. .

本発明によれば、経時における変臭・変色がなく(もしくは少なく)、保存安定性が良好であるとともに、リノール酸を配合した場合と同様の優れた美白効果を奏する皮膚外用剤を提供することができる。   According to the present invention, there is provided an external preparation for skin that has no (or less) odor and discoloration over time, has good storage stability, and has the same excellent whitening effect as when linoleic acid is blended. Can do.

以下、本発明について詳細に説明する。なお、本明細書において、「〜」はその前後の数値を含む範囲を意味するものとする。また、数値について、「以上」は、その数値及びその数値を超える範囲を意味し、及び「以下」は、その数値及びその数値未満の範囲を意味する。
本発明は、ショ糖リノール酸エステルを有効成分として含有する美白用皮膚外用剤に関する。ショ糖は、リノール酸のカルボキシル基とエステル結合可能な8つの水酸基を有する。本発明に用いるショ糖リノール酸エステルは、モノエステル体、ジエステル体、及びポリエステル体のいずれであってもよいし、これらのうちの2種又は3種を所定の割合で含む混合物であってもよい。また、ショ糖のいずれの位置の水酸基がリノール酸のカルボキシル基とエステル結合していてもよい。
Hereinafter, the present invention will be described in detail. In the present specification, “to” means a range including numerical values before and after. Regarding numerical values, “above” means the numerical value and a range exceeding the numerical value, and “below” means the numerical value and a range less than the numerical value.
The present invention relates to a whitening skin external preparation containing sucrose linoleic acid ester as an active ingredient. Sucrose has eight hydroxyl groups that can be esterified with the carboxyl group of linoleic acid. The sucrose linoleic acid ester used in the present invention may be any of a monoester, a diester, and a polyester, or may be a mixture containing two or three of these in a predetermined ratio. Good. Further, the hydroxyl group at any position of sucrose may be ester-bonded to the carboxyl group of linoleic acid.

前記ショ糖リノール酸エステルは、一般的なエステル化反応により製造することができる。例えば、ショ糖、リノール酸又はリノール酸のアルコールエステル(例えばリノール酸メチル)及び炭酸水素カリウム等の触媒を、ジメチルスルホキシド(DMSO)等の有機溶媒中に溶解し、エステル化反応を進行させる。その後、DMSO等の有機溶媒を除去し、所望により、水洗等することで得られる。触媒中和用に無水クエン酸等を添加してもよい。エステル化反応進行時には、必要により、加熱又は冷却してもよいし、また反応液を攪拌してもよい。ショ糖及びリノール酸の仕込み量を調整することで、又は温度等の反応条件を調整することで、例えば、モノエステル体、ジエステル体及びポリエステル体を、所望の割合で含むショ糖リノール酸エステルが得られる。モノエステル体、ジエステル体及び各種のポリエステル体を単離する場合や、異なる組成比のショ糖リノール酸エステルを調製する場合は、エステル化反応により得られたモノエステル体、ジエステル体及びポリエステル体の混合物を、カラムクロマトグラフィー等で精製するのが好ましい。また、得られる生成物中には、未反応のショ糖が含まれる場合もあるが、そのまま皮膚外用剤中に配合してもよいし、上記精製法等で除去してから配合してもよい。   The sucrose linoleic acid ester can be produced by a general esterification reaction. For example, sucrose, linoleic acid, or an alcohol ester of linoleic acid (for example, methyl linoleate) and a catalyst such as potassium hydrogen carbonate are dissolved in an organic solvent such as dimethyl sulfoxide (DMSO) to advance the esterification reaction. Thereafter, an organic solvent such as DMSO is removed and, if desired, obtained by washing with water. Anhydrous citric acid or the like may be added for catalyst neutralization. When the esterification reaction proceeds, if necessary, it may be heated or cooled, and the reaction solution may be stirred. By adjusting the amount of sucrose and linoleic acid charged, or by adjusting the reaction conditions such as temperature, for example, a sucrose linoleic acid ester containing a monoester body, a diester body and a polyester body in a desired ratio can get. When isolating monoesters, diesters and various polyesters, or when preparing sucrose linoleic acid esters with different composition ratios, the monoesters, diesters and polyesters obtained by the esterification reaction The mixture is preferably purified by column chromatography or the like. In addition, the product obtained may contain unreacted sucrose, but it may be blended in the skin external preparation as it is, or may be blended after being removed by the purification method or the like. .

ショ糖とリノール酸のエステル体のうち、細胞毒性が低い点及び美白効果が高い点で、ジエステル体が好ましく、ジエステル体を多く含有するショ糖リノール酸エステルを用いるのが好ましい。用いるショ糖リノール酸エステルは、ジエステル体を20質量%以上含有しているのが好ましく、30質量%以上含有しているのがより好ましく、50質量%以上含有しているのがさらに好ましい。一方、モノエステル体は、細胞毒性の観点からは、ジエステル体に劣るものの、美白効果は最も高いので、用いるショ糖リノール酸エステル中にある程度含有されているのが好ましい。用いるショ糖リノール酸エステルは、モノエステル体を20質量%以上含有しているのが好ましく、30質量%以上含有しているのがより好ましく、40質量%以上含有しているのがさらに好ましい。   Of the ester bodies of sucrose and linoleic acid, diester bodies are preferred in terms of low cytotoxicity and high whitening effect, and sucrose linoleic acid esters containing a large amount of diester bodies are preferably used. The sucrose linoleic acid ester to be used preferably contains 20% by mass or more of a diester, more preferably 30% by mass or more, and still more preferably 50% by mass or more. On the other hand, monoesters are inferior to diesters from the viewpoint of cytotoxicity, but have the highest whitening effect, and therefore are preferably contained to some extent in the sucrose linoleate used. The sucrose linoleic acid ester to be used preferably contains 20% by mass or more of a monoester, more preferably 30% by mass or more, and further preferably 40% by mass or more.

ショ糖リノール酸エステルは、そのエステル化の程度や、モノ、ジ及びポリエステル体等の組成比に応じて、常温における状態が異なり、固体〜ペースト状の形態で存在する。例えば、モノエステル体の比率が高くなると、常温で固体となり、ジ又はポリエステル体の比率が高くなるとペースト状になる。この形態はいずれであってもよく、皮膚外用剤の剤型に応じて配合しやすい形態となるように、モノ、ジ及びポリエステル体の比率を調整してもよい。   The sucrose linoleic acid ester varies in the state at room temperature depending on the degree of esterification and the composition ratio of mono-, di-, and polyester bodies, and exists in a solid to paste form. For example, when the ratio of the monoester body becomes high, it becomes solid at room temperature, and when the ratio of the di- or polyester body becomes high, it becomes a paste. This form may be any, and the ratio of the mono-, di-, and polyester bodies may be adjusted so that the form can be easily blended according to the dosage form of the external preparation for skin.

本発明の美白用皮膚外用剤中のショ糖リノール酸エステルの含有量の好ましい範囲は、皮膚外用剤の剤型やショ糖リノール酸エステルのモノ、ジ及びポリエステル体等の組成比に応じて変動するが、一般的には、皮膚外用剤の全質量中、0.01〜20質量%であるのが好ましく、0.1〜5質量%であるのがより好ましい。ショ糖リノール酸エステルの含有量が前記範囲であると、ショ糖リノール酸エステルの配合に起因するべたつき感を生じることなく、優れた美白効果を有する皮膚外用剤となる。また、上記した通り、皮膚外用剤の剤型によってショ糖リノール酸エステルの含有量の好ましい範囲も変動し、例えば、化粧水の形態では、0.01〜3質量%が好ましく、0.1〜1質量%がより好ましい。また、乳液の形態では、0.01〜15質量%が好ましく、0.5〜10質量%がより好ましい。また、クリームの形態では、0.01〜20質量%が好ましく、0.5〜15質量%がより好ましい。   The preferred range of the content of sucrose linoleic acid ester in the whitening skin external preparation of the present invention varies depending on the dosage form of the external skin preparation and the composition ratio of mono-, di- and polyester bodies of sucrose linoleic acid ester. However, generally, it is preferably 0.01 to 20% by mass and more preferably 0.1 to 5% by mass in the total mass of the external preparation for skin. When the content of the sucrose linoleic acid ester is within the above range, the skin external preparation has an excellent whitening effect without causing a sticky feeling due to the blending of the sucrose linoleic acid ester. In addition, as described above, the preferable range of the content of sucrose linoleic acid ester varies depending on the dosage form of the external preparation for skin, for example, in the form of a skin lotion, preferably 0.01 to 3% by mass, 1% by mass is more preferable. Moreover, 0.01-15 mass% is preferable in the form of an emulsion, and 0.5-10 mass% is more preferable. Moreover, in the form of a cream, 0.01-20 mass% is preferable and 0.5-15 mass% is more preferable.

また、本発明の皮膚外用剤は、乳化型皮膚外用剤であってもよく、かかる場合は、W/O型及びO/W型のいずれであってもよい。ショ糖リノール酸エステルは、水相及び油相のいずれにも添加可能であり、皮膚外用剤の調製を容易にする点でも有用な剤である。   In addition, the skin external preparation of the present invention may be an emulsified skin external preparation, and in such a case, either the W / O type or the O / W type may be used. Sucrose linoleic acid ester can be added to both the aqueous phase and the oil phase, and is also a useful agent in terms of facilitating preparation of a skin external preparation.

本発明において、ショ糖リノール酸エステルは、美白用皮膚外用剤の有効成分、即ち、美白剤として用いられる。なお、本明細書において「美白」の用語は、肌を白くする効果のみならず、肌の黒化を抑制する効果も含む意味で用いるものとする。例えば、しみ、そばかす等の色素沈着を改善する効果のみならず、色素沈着を抑制する効果も含むものとする。ショ糖リノール酸エステルが美白効果を奏する機構の詳細については定かでないが、ショ糖リノール酸エステルが、メラニンの合成を促進するチロシナーゼタンパク質に対して分解促進能を有することに起因するものと推察される。   In the present invention, sucrose linoleic acid ester is used as an active ingredient of a skin whitening external preparation, that is, a whitening agent. In the present specification, the term “whitening” is used to include not only the effect of whitening the skin but also the effect of suppressing the blackening of the skin. For example, it includes not only the effect of improving pigmentation such as stains and freckles but also the effect of suppressing pigmentation. The details of the mechanism of whitening effect of sucrose linoleate are not clear, but it is assumed that sucrose linoleate has the ability to promote degradation of tyrosinase protein that promotes melanin synthesis. The

本発明の皮膚外用剤は、ショ糖リノール酸エステルとともに、他の薬効成分を含有していてもよい。特に、他の美白剤と組み合わせると美白効果がより高くなるので好ましく、さらにショ糖リノール酸エステルの上記推定機構とは異なる機構により美白効果を奏する美白剤と組み合わせると、その効果が相乗的に高められるので好ましい。ここで、皮膚の黒化のメカニズムの概略は、紫外線やケラチノサイトより分泌されるメラノサイト活性化因子等の刺激により、メラノサイト内でチロシナーゼ遺伝子の発現が高まってチロシナーゼタンパク質が合成され、このチロシナーゼタンパク質の酵素反応により、チロシンからメラニンが合成され、その後、メラニンがケラチノサイトへと受け渡され、皮膚の色が黒くなると考えられている。従来公知の美白剤として、以下の機構により美白効果を奏する剤がそれぞれ知られている;
(1) メラノサイト活性化因子がメラノサイトに作用するのを阻害する、
(2) メラノサイト内のチロシナーゼタンパク質の活性を阻害する、
(3) チロシナーゼタンパク質の分解を促進する、
(4) チロシンからメラニンへの合成の際の酸化を抑制する。
上記した通り、ショ糖リノール酸エステルは、(3)の機構によりメラニンの合成を抑制して、美白効果を奏すると推察される。従って、(1)、(2)及び(4)の機構により美白効果を奏する美白剤と組み合わせるのが好ましく、機構の連関性から、(2)又は(4)の機構により美白効果を奏する美白剤と組み合わせるのがより好ましい。(1)の機構により美白効果を奏する美白剤としては、t−AMCHA(t−4−アミノメチル−シクロヘキサンカルボン酸)、カモミラET等が挙げられる。(2)の機構により美白効果を奏する美白剤としては、アルブチン、エラグ酸、ルシノール(4−n−ブチルレゾルシノール)、t−AMCHA、アスコルビン酸及びその誘導体が挙げられる。(4)の機構により美白効果を奏する美白剤としては、アスコルビン酸及びその誘導体が挙げられる。中でも、アルブチン、エラグ酸並びにアスコルビン酸及びその誘導体から選ばれる少なくとも一種と組み合わせるのが好ましい。アスコルビン酸の誘導体の好ましい例としては、アスコルビン酸リン酸エステルマグネシウム塩、アスコルビン酸リン酸エステルナトリウム塩、アスコルビン酸パルミチン酸エステル、アスコルビン酸グルコシド、アスコルビン酸エチルが挙げられる。
The external preparation for skin of the present invention may contain other medicinal ingredients together with sucrose linoleic acid ester. In particular, it is preferable to combine with other whitening agents because the whitening effect is higher, and when combined with a whitening agent that exhibits a whitening effect by a mechanism different from the above estimated mechanism of sucrose linoleic acid ester, the effect is synergistically enhanced. This is preferable. Here, the outline of the mechanism of skin blackening is that tyrosinase protein expression is increased in melanocytes by the stimulation of melanocyte activator secreted from ultraviolet rays and keratinocytes, and tyrosinase protein is synthesized. It is thought that melanin is synthesized from tyrosine by the reaction, and then melanin is transferred to keratinocytes, and the skin color becomes black. As conventionally known whitening agents, agents that exhibit a whitening effect by the following mechanisms are known, respectively;
(1) inhibits melanocyte activator from acting on melanocytes,
(2) inhibits the activity of tyrosinase protein in melanocytes,
(3) promote the degradation of tyrosinase protein,
(4) Suppresses oxidation during synthesis from tyrosine to melanin.
As described above, it is speculated that sucrose linoleic acid ester suppresses the synthesis of melanin by the mechanism of (3) and exhibits a whitening effect. Therefore, it is preferable to combine it with a whitening agent that exhibits a whitening effect by the mechanism of (1), (2), and (4). From the relationship of the mechanism, a whitening agent that exhibits a whitening effect by the mechanism of (2) or (4) It is more preferable to combine with. Examples of the whitening agent that exhibits a whitening effect by the mechanism (1) include t-AMCHA (t-4-aminomethyl-cyclohexanecarboxylic acid), chamomile ET, and the like. Examples of the whitening agent having a whitening effect by the mechanism (2) include arbutin, ellagic acid, lucinol (4-n-butylresorcinol), t-AMCHA, ascorbic acid and derivatives thereof. Examples of the whitening agent having a whitening effect by the mechanism (4) include ascorbic acid and its derivatives. Among them, it is preferable to combine with at least one selected from arbutin, ellagic acid, ascorbic acid and derivatives thereof. Preferable examples of the derivatives of ascorbic acid include ascorbic acid phosphate magnesium salt, ascorbic acid phosphate sodium salt, ascorbyl palmitate, ascorbic acid glucoside, and ethyl ascorbate.

本発明の皮膚外用剤には、上記必須成分の他に、化粧料や医薬部外品、外用医薬品等に通常使用される各種の成分、即ち、水、アルコール、油剤、界面活性剤、増粘剤、粉体、キレート剤、pH調整剤、各種薬効剤、動植物・微生物由来の抽出物、香料等を、本発明の効果を損なわない範囲で適宜加えることができる。各種薬効剤としては、例えば、抗酸化剤、細胞賦活剤、抗炎症剤、紫外線防止剤等が挙げられ、これらの薬効剤を併用して、本発明の効果を更に高める、もしくは他の効果をさらに付加してもよい。   In addition to the above essential components, the external preparation for skin of the present invention includes various components that are usually used in cosmetics, quasi-drugs, external medicines, etc., that is, water, alcohol, oils, surfactants, thickeners. Agents, powders, chelating agents, pH adjusting agents, various medicinal agents, extracts derived from animals, plants and microorganisms, fragrances, and the like can be added as appropriate within the range not impairing the effects of the present invention. Examples of the various medicinal agents include antioxidants, cell activators, anti-inflammatory agents, UV inhibitors, and the like, and these medicinal agents are used in combination to further enhance the effects of the present invention, or other effects. Further, it may be added.

本発明の皮膚外用剤の形態については、特に限定されず、例えば、乳液、クリーム、化粧水、パック、洗浄料、メーキャップ化粧料、分散液、軟膏、液剤、エアゾール、貼付剤、パップ剤、リニメント剤等の、いずれの形態の化粧料であっても、外用医薬品等であってもよい。   The form of the external preparation for skin of the present invention is not particularly limited, and examples thereof include emulsions, creams, lotions, packs, cleaning agents, makeup cosmetics, dispersions, ointments, liquids, aerosols, patches, cataplasms, liniments. Any form of cosmetic, such as an agent, may be an external medicine.

以下に実施例を挙げて本発明をさらに具体的に説明するが、本発明の範囲は下記の実施例に限定されることはない。
[例1:ショ糖リノール酸エステルの調製]
まず、反応容器に、ショ糖を76質量部、リノール酸メチルを64質量部、ジメチルスルホキシド(DMSO)を190質量部及び触媒(炭酸水素化カリウム)を2〜2.5質量部を入れ、ショ糖とリノール酸とのエステル化反応を進行させた。反応終了後、触媒中和用に無水クエン酸を添加し、DMSOを除去し、その後、水洗して生成物(試料1)を得た。
この生成物を、逆相カラムクロマトグラフィー(溶離液はエタノール→ヘキサン)により分画し、それぞれの分画を混合等することで、表1に示す組成の試料2〜4をそれぞれ得た。
得られた試料1〜4について、イヤトロスキャン分析法(TLC/FID分析法)により、モノエステル、ジエステル、及びポリエステルの組成を調べ、全体を100とした時の質量%で求めた結果を表1に示した。なお、分析には、株式会社ヤトロンの薄層自動検出装置イヤトロンスキャンTH−10を用いた。
The present invention will be described more specifically with reference to the following examples. However, the scope of the present invention is not limited to the following examples.
[Example 1: Preparation of sucrose linoleic acid ester]
First, 76 parts by mass of sucrose, 64 parts by mass of methyl linoleate, 190 parts by mass of dimethyl sulfoxide (DMSO) and 2 to 2.5 parts by mass of a catalyst (potassium hydrogencarbonate) were placed in a reaction vessel. The esterification reaction between sugar and linoleic acid was allowed to proceed. After completion of the reaction, anhydrous citric acid was added to neutralize the catalyst, DMSO was removed, and then washed with water to obtain a product (sample 1).
This product was fractionated by reversed-phase column chromatography (eluent: ethanol → hexane), and the fractions were mixed to obtain Samples 2 to 4 having the compositions shown in Table 1, respectively.
About the obtained samples 1-4, the composition of monoester, diester, and polyester was investigated by the eartro scan analysis method (TLC / FID analysis method), and the result calculated | required by the mass% when the whole was set to 100 is represented. It was shown in 1. In addition, the thin layer automatic detection apparatus Iatron scan TH-10 of Yatron Co., Ltd. was used for the analysis.

Figure 0005399701
Figure 0005399701

[例2:メラニン産生抑制効果]
2枚の6穴のシャーレに培地を適量採取し、マウス由来B16メラノーマ細胞を播種し、37℃、二酸化炭素濃度5v/v%中にて静置した。翌日、各試料を最終濃度が所定の濃度となるようにエタノールに溶解した検体調製液を添加混和した。尚、対照は溶液(エタノール)のみを添加混合した。培養5日目に培地を交換し、再度検体調製液を添加する。翌日、培地を撤去し、1枚のシャーレについて細胞をリン酸緩衝液にて洗浄した後回収し、B16メラノーマ培養細胞の白色化度を以下の基準にて目視で評価した。
(判定基準)
++:対照に対して極めて白色である。
+:対照に対して明らかに白色である。
±:対照に対してやや白色である。
−:対照と同じ黒色である。
[Example 2: Melanin production inhibitory effect]
An appropriate amount of the medium was collected in two 6-well petri dishes, seeded with mouse-derived B16 melanoma cells, and allowed to stand at 37 ° C. in a carbon dioxide concentration of 5 v / v%. On the next day, a sample preparation solution in which each sample was dissolved in ethanol so that the final concentration was a predetermined concentration was added and mixed. As a control, only a solution (ethanol) was added and mixed. On the fifth day of culture, the medium is changed, and the sample preparation solution is added again. On the next day, the medium was removed, the cells were washed with a phosphate buffer in one petri dish, and then collected, and the degree of whitening of the cultured B16 melanoma cells was visually evaluated according to the following criteria.
(Criteria)
++: Extremely white relative to the control.
+: Clearly white relative to the control.
±: Slightly white with respect to the control.
-: The same black color as the control.

残りの1枚のシャーレについて、細胞をホルマリン固定後、1%クリスタルバイオレット溶液を添加し、染色した。各検体濃度に対する生存細胞数(A)及び対照の細胞数(B)をモノセルレータによって測定し、(A)/(B)%の比率により細胞生存率を算出した。
各試料のそれぞれの濃度における白色化度の評価、及び細胞生育率を下記表2に示す。
For the remaining one petri dish, cells were fixed with formalin, and then a 1% crystal violet solution was added and stained. The number of viable cells (A) and the number of control cells (B) for each analyte concentration were measured with a monocellator, and the cell viability was calculated by the ratio of (A) / (B)%.
Table 2 below shows the evaluation of the degree of whitening and the cell growth rate at each concentration of each sample.

Figure 0005399701
ND:判定不能
Figure 0005399701
ND: Cannot be determined

上記結果より、ショ糖リノール酸エステルの試料1〜4はいずれも、リノール酸と同等の高いメラニン産生抑制能を示した。特に、モノエステル体の割合が20質量%以上である試料2、ジエステル体の割合が20質量%以上である試料3、及び双方の割合が20質量%以上である試料1は、特に高いメラニン産生抑制能を示した。   From the above results, all samples 1 to 4 of sucrose linoleic acid ester showed a high melanin production inhibitory ability equivalent to linoleic acid. In particular, Sample 2 in which the proportion of monoester is 20% by mass or more, Sample 3 in which the proportion of diester is 20% by mass or more, and Sample 1 in which the proportion of both is 20% by mass or more are particularly high in melanin production. Suppressive ability was shown.

[例3:ヒトUV惹起色素沈着抑制試験]
例1で調製した試料1を1質量%配合したクリーム1、及び試料1を1質量%及びアルブチンを3質量%配合したクリーム2をそれぞれ調製した。また、比較用に、アルブチンのみを3質量%配合したクリーム3と、試料1及びアルブチンの両者を配合していないブランククリームをそれぞれ調製した。各クリームの組成を表3にそれぞれ示す。以下の製造方法によりそれぞれ調製した。
A. 成分4〜7を混合し、70℃で加熱溶解する。
B. 成分1〜3を混合した後70℃に加温し、Aを入れ乳化した後、成分8〜11を添加混合する。
C. 成分12〜14を混合溶解し、Bに添加し均一に混合する。
D. Cを容器に充填し試験用クリームを得た。
[Example 3: Human UV-induced pigmentation inhibition test]
Cream 1 containing 1% by mass of Sample 1 prepared in Example 1 and Cream 2 containing 1% by mass of Sample 1 and 3% by mass of arbutin were prepared. Moreover, the cream 3 which mix | blended 3 mass% only of arbutin and the blank cream which did not mix | blend both the sample 1 and arbutin were prepared for the comparison, respectively. Table 3 shows the composition of each cream. Each was prepared by the following production method.
A. Ingredients 4-7 are mixed and dissolved by heating at 70 ° C.
B. Components 1 to 3 are mixed, then heated to 70 ° C., A is added and emulsified, and then components 8 to 11 are added and mixed.
C. Components 12 to 14 are mixed and dissolved, added to B, and mixed uniformly.
D. C was filled into a container to obtain a test cream.

Figure 0005399701
Figure 0005399701

被験者の上腕内側部の4箇所に、約1MEDの紫外線を3日間(1日目〜3日目まで)照射して、人工的に色素沈着を形成した。
また、それぞれのクリームを4箇所の照射部に7日間(照射1日目〜7日目まで)、1日2回塗布を行った。
尚、ヒトUV惹起色素沈着抑制能については、目視判定を照射及びクリーム塗布から7日目に、色差測定判定を3日目と7日目にそれぞれ下記の方法にて判定し、評価を行った。
・目視判定
3名の熟練判定者が、複数の被験者について、ブランククリームの塗布部位と、クリーム1〜3をそれぞれ塗布した塗布部位の計4箇所の色素沈着の程度を比較し、その差を3段階(+1、0、−1:但し、「−1」の評価が最も紫外線による色素沈着の程度が高く、「0」、「+1」になるにしたがって色素沈着の程度が低く、通常の肌色に近づいたという評価である)で評価した。判定者の評価の数値の平均値(但し、ブランククリームの塗布部位の平均値を0として換算した平均値)を目視ポイントとした。なお、判定は、上記作業を7日間行った後に実施した。結果を下記表4に示す。
・色差測定判定
ミノルタ色彩色差計CR−200を用いて、ブランククリームの塗布部位と、クリーム1〜3をそれぞれ塗布した部位との色差を測定した。測定は、上記作業を3日間行った後と、7日間行った後に実施した。結果を下記表5に示す。
Four places on the inner side of the upper arm of the subject were irradiated with ultraviolet rays of about 1 MED for 3 days (from day 1 to day 3) to artificially form pigmentation.
Each cream was applied twice a day for 7 days (from the first day to the seventh day of irradiation) on four irradiated parts.
The ability to suppress human UV-induced pigmentation was evaluated by determining the visual determination on the 7th day after irradiation and cream application, and determining the color difference measurement on the 3rd and 7th days by the following methods. .
-Visual judgment Three skilled judges have compared the degree of pigmentation of a total of four places, the application part of a blank cream, and the application part which applied creams 1-3 about a plurality of subjects, and the difference is 3 Stage (+1, 0, −1: However, the evaluation of “−1” indicates the highest degree of pigmentation due to ultraviolet rays, and the degree of pigmentation decreases as “0” and “+1” indicate normal skin color. It was an evaluation of approaching). The average value of the numerical values of the judge's evaluation (however, the average value obtained by converting the average value of the blank cream application site to 0) was taken as the visual point. The determination was made after the above work was performed for 7 days. The results are shown in Table 4 below.
-Color difference measurement determination The color difference of the application | coating site | part of a blank cream and the site | part which each applied the creams 1-3 was measured using Minolta color difference meter CR-200. The measurement was performed after the above work was performed for 3 days and after 7 days. The results are shown in Table 5 below.

Figure 0005399701
Figure 0005399701

Figure 0005399701
Figure 0005399701

上記表4及び表5に示した結果から、ショ糖リノール酸エステルである試料1を含有するクリーム1及び2は、いずれも優れたヒトUV惹起色素沈着抑制能を示すことが理解できる。特に、ショ糖リノール酸エステル及びアルブチンの双方を含有するクリーム2は、アルブチンのみを含有するクリーム3と比較して、格段に優れたヒトUV惹起色素沈着抑制能を示すことが理解できる。   From the results shown in Tables 4 and 5 above, it can be understood that creams 1 and 2 containing Sample 1 which is a sucrose linoleic acid ester exhibit excellent human UV-induced pigmentation-inhibiting ability. In particular, it can be understood that the cream 2 containing both sucrose linoleic acid ester and arbutin exhibits a far superior ability to suppress human UV-induced pigmentation compared to the cream 3 containing only arbutin.

[例4:くすみ改善効果の評価]
下記表6に示す組成の化粧水を以下の方法でそれぞれ調製した。
A. 成分1〜11を均一に混合溶解し、70℃に加温した。
B. 成分12〜17を均一に混合溶解し、70℃に加温した。
C. BにAを加えてホモミキサーで攪拌し、容器に充填し化粧水を得た。
[Example 4: Evaluation of dullness improvement effect]
The lotions having the compositions shown in Table 6 below were prepared by the following methods.
A. Components 1 to 11 were mixed and dissolved uniformly and heated to 70 ° C.
B. Ingredients 12 to 17 were mixed and dissolved uniformly and heated to 70 ° C.
C. A was added to B, stirred with a homomixer, filled into a container, and a lotion was obtained.

下記表7に示す組成のクリームを以下の方法でそれぞれ調製した。
A. 成分1〜11を70℃で加温溶解し、均一に混合した。
B. 成分12〜20を70℃で加温溶解し、均一に混合した。
C. AにBを加えてホモミキサーで攪拌、乳化後、容器に充填しW/O型クリームを得た。
Creams having the compositions shown in Table 7 below were prepared by the following methods.
A. Ingredients 1 to 11 were dissolved by heating at 70 ° C. and mixed uniformly.
B. Ingredients 12 to 20 were dissolved by heating at 70 ° C. and mixed uniformly.
C. B was added to A, stirred and emulsified with a homomixer, and then filled into a container to obtain a W / O type cream.

調製した各化粧水及び各W/O型クリームについて、下記の方法および基準により評価した。
(試験方法:くすみ改善効果)
化粧水1〜6及びW/O型クリーム4〜7に関して、1品につき35〜59才の女性10名をパネルとし、毎日朝と夜の2回、12週間にわたって洗顔後に被験化粧水またはクリームの適量を顔面左半分に塗布してもらった。同時に、比較用化粧水7〜8及び比較用W/O型クリーム8〜10に関して、上記と同様の方法で適量を顔面右半分に塗布してもらった。塗布によるくすみ改善効果を、以下のそれぞれの基準によって評価した。
(評価基準)
くすみ改善効果
<評価> <内容>
有 効 肌のくすみが目立たなくなった。
やや有効 肌のくすみがあまり目立たなくなった。
無 効 使用前と変化がなかった。
<判定>
◎:有効及びやや有効が9名以上
○:有効及びやや有効が6名以上8名以下
△:有効及びやや有効が3名以上5名以下
×:有効及びやや有効が2名以下
評価結果を表6及び7にそれぞれ示す。
Each prepared lotion and each W / O type cream was evaluated by the following methods and criteria.
(Test method: Dullness improvement effect)
With regard to lotion 1-6 and W / O type cream 4-7, 10 females aged 35-59 years per panel were used as panels. Appropriate amount was applied to the left half of the face. At the same time, with respect to the comparative lotions 7 to 8 and the comparative W / O creams 8 to 10, an appropriate amount was applied to the right half of the face in the same manner as described above. The dullness improvement effect by application was evaluated according to the following criteria.
(Evaluation criteria)
Dullness improvement effect <Evaluation><Contents>
Effective Skin dullness is not noticeable.
Slightly effective Skin dullness is less noticeable.
Invalid No change from before use.
<Judgment>
◎: Effective and slightly effective is 9 or more ○: Effective and slightly effective is 6 or more and 8 or less △: Effective and slightly effective is 3 or more and 5 or less ×: Effective and slightly effective is 2 or less Evaluation result is shown Shown in 6 and 7, respectively.

(肌の保湿感と柔軟性に関する評価方法)
化粧水1〜8及びW/O型クリーム4〜10の各試料につき、(イ)肌の保湿感、(ロ)肌の柔軟性について上記10名の女性パネル員により官能検査を行った。官能検査は、毎日朝と夜の2回、12週間にわたって使用した後、サンプル毎に、下記絶対評価基準に基づき7段階で評価を行い、その評点の平均値を更に下記判定基準に基づき判定した。
<絶対評価基準>
(評点): (評価)
6 : 非常に良い
5 : 良い
4 : やや良い
3 : 普通
2 : やや悪い
1 : 悪い
0 : 非常に悪い
<判定基準>
(評点の平均値) :(判定)
5.0以上 : ◎ (非常に良好)
3.5以上、5.0未満 : ○ (良好)
1.0以上、3.5未満 : △ (やや不良)
1.0未満 : × (不良)
評価結果を表6及び7にそれぞれ併記する。
(Evaluation method for skin moisturizing feeling and flexibility)
For each sample of lotions 1 to 8 and W / O type creams 4 to 10, a sensory test was conducted by (10) moisturizing feeling of skin and (b) skin flexibility by the 10 female panel members. The sensory test was used twice a day in the morning and at night for 12 weeks, and then each sample was evaluated in 7 stages based on the following absolute evaluation criteria, and the average score was further determined based on the following criteria. .
<Absolute evaluation criteria>
(Score): (Evaluation)
6: Very good 5: Good 4: Somewhat good 3: Normal 2: Somewhat bad 1: Bad 0: Very bad <Criteria>
(Average score): (Judgment)
5.0 or higher: ◎ (very good)
3.5 or more and less than 5.0: ○ (Good)
1.0 or more and less than 3.5: △ (somewhat poor)
Less than 1.0: × (defect)
The evaluation results are shown in Tables 6 and 7, respectively.

(保存安定性試験(変臭・変色))
化粧水1〜8及びW/O型クリーム4〜10の各試料につき、5℃及び40℃の恒温槽に、それぞれ3ヶ月間保存した後、経日による臭いと色の変化を比較した。評価は、5℃保存のサンプルを基準とし、これに対して40℃保存のサンプルを比較し、下記の評価基準により評価した。
(評価基準)
◎:基準品と変化(変臭、変色)がない。
○:基準品と比較してやや変化(変臭、変色)があるが、問題ない。
×:基準品と比べ明らかに変化(変臭、変色)があり、問題である。
結果を表6及び表7にそれぞれ示す。


(Storage stability test (odour and discoloration))
The samples of lotions 1 to 8 and W / O type creams 4 to 10 were stored in thermostats at 5 ° C. and 40 ° C. for 3 months, respectively, and then the odor and color change due to aging were compared. Evaluation was based on a sample stored at 5 ° C., and a sample stored at 40 ° C. was compared with the sample, and evaluated according to the following evaluation criteria.
(Evaluation criteria)
A: There is no change (odour, discoloration) from the standard product.
○: There is a slight change (odour, discoloration) compared to the standard product, but there is no problem.
X: There is a clear change (odour, discoloration) compared to the standard product, which is a problem.
The results are shown in Table 6 and Table 7, respectively.


Figure 0005399701
Figure 0005399701

Figure 0005399701
Figure 0005399701

表6及び表7の結果より明らかなように、本発明品である化粧水1〜6及びW/O型クリーム4〜7は、くすみ改善効果、保存安定性、肌の保湿性、肌の柔軟性に優れるものであり、使用感も良好なものであった。一方、比較品である化粧水7〜8及びW/O型クリーム8〜10は、全ての評価項目について本発明品と同等なものはなかった。
例えば、化粧水7及び8では、ショ糖リノール酸エステルの替わりに、ショ糖とステアリン酸とがエステル結合したショ糖ジステアリン酸エステル、及びショ糖とパルミチン酸とがエステル結合したショ糖ジパルミチン酸エステルをそれぞれ配合したが、化粧水1〜6のようなくすみ改善効果は得られなかった。
また、W/O型クリーム8及び9では、ショ糖リノール酸エステルの替わりに、ショ糖ジステアリン酸エステル及びショ糖ジパルミチン酸エステルをそれぞれ配合したが、同様に、クリーム4〜7のようなくすみ改善効果が得られなかった。
また、W/O型クリーム10では、ショ糖リノール酸エステルの替わりに、リノール酸を配合したが、特に変臭、変色が観察され、保存安定性に問題があった。
As is clear from the results of Tables 6 and 7, the skin lotions 1 to 6 and the W / O creams 4 to 7 that are the products of the present invention have a dullness improving effect, storage stability, skin moisture retention, skin flexibility. It was excellent in the properties and the usability was also good. On the other hand, lotions 7 to 8 and W / O type creams 8 to 10 as comparative products were not equivalent to the products of the present invention for all evaluation items.
For example, in lotions 7 and 8, in place of sucrose linoleate, sucrose distearate in which sucrose and stearic acid are ester-bonded, and sucrose dipalmitate in which sucrose and palmitic acid are ester-bonded Although each ester was blended, the dullness improving effect was not obtained as in skin lotions 1-6.
In addition, in W / O type creams 8 and 9, sucrose distearate and sucrose dipalmitate were blended in place of sucrose linoleate, respectively. The improvement effect was not obtained.
Moreover, in W / O type cream 10, linoleic acid was blended in place of sucrose linoleic acid ester. However, particularly, odor and discoloration were observed, and there was a problem in storage stability.

[例5:紫外線防止美容液の調製]
表8に示す組成の美容液を、下記方法により調製した。
A. 成分1〜11を70℃で加温溶解し、均一に混合した。
B. 成分12〜18を70℃で加温溶解し、均一に混合した。
C. BにAを加えてホモミキサーで攪拌し、容器に充填し美容液を得た。
[Example 5: Preparation of UV-preventing serum]
A cosmetic liquid having the composition shown in Table 8 was prepared by the following method.
A. Ingredients 1 to 11 were dissolved by heating at 70 ° C. and mixed uniformly.
B. Ingredients 12 to 18 were dissolved by heating at 70 ° C. and mixed uniformly.
C. A was added to B, and the mixture was stirred with a homomixer and filled in a container to obtain a serum.

Figure 0005399701
Figure 0005399701

調製した紫外線防止美容液は、美白効果に優れ、使用感も良好であった。また、経時による変色・変臭も観察されなかった。   The prepared UV-preventing cosmetic liquid was excellent in whitening effect and good in use. Further, no discoloration or odor change over time was observed.

[例6:クレンジングクリームの調製]
表9に示す組成のクレンジングクリームを、下記の方法により調製した。
A. 成分1〜12を70℃で加温溶解し、均一に混合した。
B. 成分13〜17を70℃で加温溶解し、均一に混合した。
C. BにAを加えてホモミキサーで攪拌、乳化後、容器に充填し、クレンジングクリームを得た。
[Example 6: Preparation of cleansing cream]
Cleansing creams having the compositions shown in Table 9 were prepared by the following method.
A. Ingredients 1-12 were dissolved by heating at 70 ° C. and mixed uniformly.
B. Ingredients 13 to 17 were dissolved by heating at 70 ° C. and mixed uniformly.
C. A was added to B and stirred and emulsified with a homomixer, and then filled into a container to obtain a cleansing cream.

Figure 0005399701
Figure 0005399701

調製したクレンジングクリームは、美白効果に優れ、使用感も良好であった。また、経時による変色・変臭も観察されなかった。   The prepared cleansing cream had an excellent whitening effect and a good feeling when used. Further, no discoloration or odor change over time was observed.

[例7:パックの調製]
下記表10に示す組成のパックを、下記の方法により調製した。
A. 成分4〜8を混合し、70℃で加熱溶解する。
B. 成分1〜3を混合した後70℃に加温し、Aを入れ乳化した後、成分9〜11を添加混合する。
C. Bに成分12を添加し中和し、成分13〜15を添加し混合する。
D. Cを容器に充填しパックを得た。
[Example 7: Preparation of pack]
A pack having the composition shown in Table 10 below was prepared by the following method.
A. Components 4 to 8 are mixed and dissolved by heating at 70 ° C.
B. Components 1 to 3 are mixed and then heated to 70 ° C., A is added and emulsified, and then components 9 to 11 are added and mixed.
C. Component 12 is added to B to neutralize, and components 13 to 15 are added and mixed.
D. C was filled into a container to obtain a pack.

Figure 0005399701
Figure 0005399701

調製したパックは、美白効果に優れ、使用感も良好であった。また、経時による変色・変臭も観察されなかった。   The prepared pack had an excellent whitening effect and a good feeling when used. Further, no discoloration or odor change over time was observed.

[例8:リキッドファンデーションの調製]
(成分) 質量%
(1)液状ラノリン 2.0
(2)流動パラフィン 5.0
(3)ステアリン酸 2.0
(4)セタノール 1.0
(5)自己乳化型モノステアリン酸グリセリル 1.0
(6)パラメトキシケイ皮酸−2−エチルヘキシル 8.0
(7)4−tert−ブチル−4’−メトキシジベンゾイルメタン
2.0
(8)試料3(例1で調製) 0.5
(9)パラオキシ安息香酸メチル 0.1
(10)グリセリン 5.0
(11)トリエタノールアミン 1.0
(12)カルボキシメチルセルロース 0.2
(13)ベントナイト 0.5
(14)精製水 残量
(15)酸化チタン 6.0
(16)微粒子酸化亜鉛 5.0
(17)マイカ 2.0
(18)タルク 4.0
(19)着色顔料 4.0
(20)オウゴン抽出物*1 0.5
(21)香料 適量
*1 一丸ファルコス社製
[Example 8: Preparation of liquid foundation]
(Ingredient) Mass%
(1) Liquid lanolin 2.0
(2) Liquid paraffin 5.0
(3) Stearic acid 2.0
(4) Cetanol 1.0
(5) Self-emulsifying glyceryl monostearate 1.0
(6) Paramethoxycinnamic acid-2-ethylhexyl 8.0
(7) 4-tert-butyl-4'-methoxydibenzoylmethane
2.0
(8) Sample 3 (prepared in Example 1) 0.5
(9) Methyl paraoxybenzoate 0.1
(10) Glycerin 5.0
(11) Triethanolamine 1.0
(12) Carboxymethylcellulose 0.2
(13) Bentonite 0.5
(14) Purified water remaining amount (15) Titanium oxide 6.0
(16) Fine zinc oxide 5.0
(17) Mica 2.0
(18) Talc 4.0
(19) Color pigment 4.0
(20) Ogon extract * 1 0.5
(21) Fragrance appropriate amount * 1 Made by Ichimaru Falcos

(製法)
A.成分(1)〜(8)を混合溶解する。
B.Aに成分(15)〜(19)を加え、均一に混合し、70℃に保つ。
C.成分(9)〜(14)を均一に溶解し、70℃に保つ。
D.CにBを添加して、均一に乳化する。
E.Dを冷却後、成分(20)、(21)を添加してリキッドファンデーションを得た。
(Manufacturing method)
A. Components (1) to (8) are mixed and dissolved.
B. Ingredients (15) to (19) are added to A, mixed uniformly, and kept at 70 ° C.
C. Ingredients (9) to (14) are uniformly dissolved and kept at 70 ° C.
D. B is added to C and emulsified uniformly.
E. After cooling D, components (20) and (21) were added to obtain a liquid foundation.

例8のリキッドファンデーションは保存安定性に優れ、また肌なじみが非常によい使用感に優れたリキッドファンデーションであった。また、上記リキッドファンデーションを肌に塗布することにより、優れた美白効果があった。   The liquid foundation of Example 8 was a liquid foundation having excellent storage stability and excellent skin feel and excellent usability. Moreover, there was an excellent whitening effect by applying the above liquid foundation to the skin.

[例9:日焼け止め乳液の調製]
(成分) 質量%
(1)ポリオキシアルキレン変性オルガノポリシロキサン 1.0
(2)ジメチルポリシロキサン 5.0
(3)オクタメチルシクロテトラシロキサン 20.0
(4)イソノナン酸イソトリデシル 5.0
(5)パラメトキシケイ皮酸−2−エチルヘキシル 5.0
(6)水添レシチン*1 1.0
(7)試料4(例1で調製) 0.5
(8)パラオキシ安息香酸メチル 0.1
(9)シリコーン処理微粒子酸化チタン 10.0
(10)シリコーン処理微粒子酸化亜鉛 10.0
(11)ポリスチレン末 3.0
(12)トリメチルシロキシケイ酸 0.5
(13)ジプロピレングリコール 3.0
(14)エチルアルコール 10.0
(15)精製水 残量
(16)塩化ナトリウム 0.2
(17)サンザシ抽出物*2 1.0
(18)香料 適量
*1 日光ケミカルズ社製 ニッコールレシノールS−10E
*2 丸善製薬社製
[Example 9: Preparation of sunscreen emulsion]
(Ingredient) Mass%
(1) Polyoxyalkylene-modified organopolysiloxane 1.0
(2) Dimethylpolysiloxane 5.0
(3) Octamethylcyclotetrasiloxane 20.0
(4) Isotridecyl isononanoate 5.0
(5) Paramethoxycinnamic acid-2-ethylhexyl 5.0
(6) Hydrogenated lecithin * 1 1.0
(7) Sample 4 (prepared in Example 1) 0.5
(8) Methyl paraoxybenzoate 0.1
(9) Silicone-treated fine particle titanium oxide 10.0
(10) Silicone-treated fine particle zinc oxide 10.0
(11) Polystyrene powder 3.0
(12) Trimethylsiloxysilicic acid 0.5
(13) Dipropylene glycol 3.0
(14) Ethyl alcohol 10.0
(15) Purified water remaining amount (16) Sodium chloride 0.2
(17) Hawthorn extract * 2 1.0
(18) Fragrance appropriate amount * 1 Nikkor Resinol S-10E manufactured by Nikko Chemicals
* 2 Made by Maruzen Pharmaceutical Co., Ltd.

(製法)
A.成分(1)〜(12)を混合する。
B.成分(13)〜(16)を混合する。
C.AにBを添加して、均一に乳化する。
D.Cに成分(17)、(18)を加えて日焼け止め乳液を得た。
(Manufacturing method)
A. Components (1) to (12) are mixed.
B. Components (13) to (16) are mixed.
C. Add B to A and emulsify uniformly.
D. Components (17) and (18) were added to C to obtain a sunscreen emulsion.

例9の日焼け止め乳液は、保存安定性に優れ、また肌なじみが非常によい使用感に優れたものであった。また、上記日焼け止め乳液を肌に塗布することにより、優れた美白効果があった。   The sunscreen emulsion of Example 9 was excellent in storage stability and very comfortable to use on the skin. Moreover, there was an excellent whitening effect by applying the sunscreen emulsion to the skin.

本発明によれば、美白効果に優れ、経時安定性も良好な、乳液、クリーム、化粧水、パック、洗浄料、メーキャップ化粧料等の皮膚外用剤を提供することができる。   ADVANTAGE OF THE INVENTION According to this invention, skin external preparations, such as a milky lotion, a cream, a lotion, a pack, a washing | cleaning agent, and makeup | decoration cosmetics, which are excellent in the whitening effect and favorable with time can be provided.

Claims (6)

ショ糖リノール酸エステルを有効成分として含有する美白用皮膚外用剤であって、
前記ショ糖リノール酸エステルが、ジエステル体を20質量%以上含む、美白用皮膚外用剤。
An external preparation for skin whitening containing sucrose linoleic acid ester as an active ingredient,
The skin external preparation for whitening in which the said sucrose linoleic acid ester contains 20 mass% or more of diester bodies.
ショ糖リノール酸エステルを有効成分として含有する美白用皮膚外用剤であって、
前記ショ糖リノール酸エステルが、モノエステル体を20質量%以上含む、美白用皮膚外用剤。
An external preparation for skin whitening containing sucrose linoleic acid ester as an active ingredient,
A skin external preparation for whitening, wherein the sucrose linoleic acid ester contains 20% by mass or more of a monoester.
ショ糖リノール酸エステルを有効成分として含有する美白用皮膚外用剤であって、
前記ショ糖リノール酸エステルが、モノエステル体を20質量%以上、及びジエステル体を20質量%以上含む、美白用皮膚外用剤。
An external preparation for skin whitening containing sucrose linoleic acid ester as an active ingredient,
The skin external preparation for whitening in which the said sucrose linoleic acid ester contains 20 mass% or more of monoester bodies, and 20 mass% or more of diester bodies.
ショ糖リノール酸エステル以外の美白剤の少なくとも一種をさらに含有する請求項1〜3のいずれか1項に記載の美白用皮膚外用剤。 The skin external preparation for whitening according to any one of claims 1 to 3, further comprising at least one whitening agent other than sucrose linoleic acid ester. 前記美白剤が、アスコルビン酸及びその誘導体、アルブチン並びにエラグ酸から選ばれる少なくとも一種である請求項4に記載の美白用皮膚外用剤。 The skin external preparation for whitening according to claim 4, wherein the whitening agent is at least one selected from ascorbic acid and derivatives thereof, arbutin and ellagic acid. ジエステル体を20質量%以上もしくはモノエステル体を20質量%以上、またはモノエステル体を20質量%以上及びジエステル体を20質量%以上含む、ショ糖リノール酸エステルを有効成分として用いる、皮膚の美白方法(医療行為を除く。)。
Skin whitening using sucrose linoleic acid ester as an active ingredient, containing 20% by mass or more of a diester or 20% by mass or more of a monoester, or 20% by mass or more of a monoester and 20% by mass or more of a diester Method (excluding medical practice).
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JPWO2007105706A1 (en) 2009-07-30
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TW200800282A (en) 2008-01-01
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