JP3632164B2 - Skin cosmetics - Google Patents

Skin cosmetics Download PDF

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Publication number
JP3632164B2
JP3632164B2 JP01741097A JP1741097A JP3632164B2 JP 3632164 B2 JP3632164 B2 JP 3632164B2 JP 01741097 A JP01741097 A JP 01741097A JP 1741097 A JP1741097 A JP 1741097A JP 3632164 B2 JP3632164 B2 JP 3632164B2
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Japan
Prior art keywords
skin
nicotinic acid
effect
biphenyl compound
test
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JP01741097A
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Japanese (ja)
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JPH10194958A (en
Inventor
俊雄 引間
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株式会社カネボウ化粧品
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Description

【0001】
【発明の属する技術分野】
本発明は、特に美白効果に優れ、さらに優れた肌荒れ防止効果、老化防止効果及び美肌効果を発現し、皮膚を健やかに保つことのできる皮膚化粧料に関する。
【0002】
【従来技術及び発明が解決しようとする課題】
従来より、肌のしみやそばかす等の予防や治療を目的とする化粧料にはL−アスコルビン酸およびその誘導体、アルブチン等のハイドロキノン誘導体、コウジ酸等のピロン類が配合されいる。
【0003】
これらの物質は、メラニン生成の抑制、生成したメラニンの淡色漂白作用等の効果を有し、美白効果を有する物質として広く知られている。しかし、これらの物質は、例えばL−アスコルビン酸およびその誘導体は保存安定性が不十分で会ったり、紫外線による炎症防止効果が十分に認められないことが多い。またハイドロキノン誘導体やピロン類は安全性が十分でないなど問題がある。この様にメラニンの生成抑制効果、メラニンの淡色化作用、炎症防止効果、安全性等、総合的に優れた美白を目的とした化粧料を得ることは困難であった。
【0004】
一方、特定のビフェニル化合物にはチロシナーゼ活性阻害効果やメラニン生成抑制効果があることが知られている(特開平6−145040号公報、特開平7−25743号公報)。しかし、これを単独で配合した場合も、美白効果は満足できるものではなかった。
【0005】
そこで本発明者らは鋭意研究した結果、表皮細胞セラミド合成促進物質と、特定のビフェニル化合物を含有する皮膚化粧料は、紫外線障害によるメラニン生成を抑制すると共に、表皮の脂質であるセラミドの合成を促して皮膚の代謝を促進し、結果としてメラニンの排泄を促し、優れた美白効果を発現することを見出した。さらに、皮膚の乾燥を防ぎ、肌荒れやしわを防ぐなど、優れた肌荒れ防止効果、老化防止効果、及び美肌効果を発現することを見出し、本発明を完成するに至った。
【0006】
本発明の目的は、特に美白効果に優れ、さらに優れた肌荒れ防止効果、老化防止効果及び美肌効果を発現し、皮膚を健やかに保つことのできる皮膚化粧料を提供することにある。
【0007】
【課題を解決するための手段】
上記目的を達成する本発明は、表皮細胞セラミド合成促進物質と、下記一般式(1)及び(2)で表されるビフェニル化合物から選ばれる少なくとも一種を含有する皮膚化粧料である。
【0008】
【化3】
【0009】
(但し、RはCH、C、C、CHOH、COH、CHCH=CHの置換基である)
【0010】
【化4】
【0011】
(但し、Rは、水素原子もしくは炭素数1から8の直鎖又は分岐鎖状の飽和炭化水素基である)
【0012】
【発明の実施の形態】
以下、本発明の実施の形態を詳述する。
【0013】
本発明に用いられる表皮細胞セラミド合成促進物質として挙げられるニコチン酸及びその誘導体としては、ニコチン酸、ニコチン酸アミド、メチルニコチン酸、エチルニコチン酸、ベンジルニコチン酸、ニコチン酸トコフェロール、クエン酸ニカメタート等があり、ニコチニルアルコール及びその塩としては、ニコチニルアルコール、酒石酸ニコチニルアルコール等があるが、これらに限定されるものではない。
【0014】
表皮細胞セラミド合成促進物質の含有量は化粧料の処方成分全量を基準として0.001〜20.0重量%が好ましい
【0015】
本発明に用いられるビフェニル化合物は公知の物質であり、例えば具体例としてデヒドロジクレオソール、デヒドロジオイゲノール、テトラハイドロマグノロール等が挙げられる(ジャーナル オブ オーガニック ケミストリィ、第28巻、1048頁、1963年:日本化学会誌、第87巻、第6号、603頁、1966年)。
【0016】
その配合量は化粧料全量中、0.0001〜20重量%が好ましい。
【0017】
本発明の化粧料には、上記原料の他に、色素、香料、防腐剤、界面活性剤、抗酸化剤、保湿剤などを、本発明の目的を達成する範囲内で適宜配合することができる。
【0018】
本発明の化粧料の剤型としては、クリーム、乳液、化粧水、パックなどが挙げられる。この化粧料は、例えば乳液等の場合、油相及び水相をそれぞれ加熱溶解したものを乳化分散して冷却する通常の方法により製造することができる。
【0019】
【実施例】
以下、実施例及び比較例に基づいて本発明を詳述する。尚、実施例に示す%とは重量%である。実施例に記載の皮膚色明度回復試験法、しわ形成抑制試験方法(老化防止効果)、荒れ肌改善効果の測定法、官能テスト(美肌効果)は下記のとおりである。
【0020】
尚、実施例におけるビフェニル化合物の名称を前記一般式のR、Rの違いにより以下のごとく記載する。
ビフェニル化合物1(R;CH)、ビフェニル化合物2(R;C)、ビフェニル化合物3(R;C)、ビフェニル化合物4(R;CHOH)、ビフェニル化合物5(R;COH)、ビフェニル化合物6(R;CHCH=CH)、ビフェニル化合物7(R;CH)、ビフェニル化合物8(R;C)、ビフェニル化合物9(R;C)、ビフェニル化合物10(R;iso−C)、ビフェニル化合物11(R;C17)、ビフェニル化合物12(R;H)。
【0021】
(1)皮膚色明度回復試験法
被験者20名の背部皮膚にUV−B領域の紫外線を最小紅斑量の2倍照射し、試料塗布部位と非塗布部位を設定して各々の皮膚の基準明度(V値,V´値)を測定した。引き続いて塗布部位には試料を1日2回ずつ15週間連続塗布した後、3,6,9,12,15週間後の塗布部位及び非塗布部位の皮膚の明度(Vn 値,Vn ´値)を測定し、下記の判定基準にしたがって皮膚色の回復を評価した。
尚、皮膚の明度(マンセル表色系V値)は高速分光色彩計で測定して得られたX,Y,Z値より算出した。また評価は被験者20名ついて、6週間後の評価点の平均値で示した。
【0022】
(2)ヘアレスマウスによるしわ形成抑制試験
ヘアレスマウス(HR/ICR、実験開始時6週齢)10匹を用い、その背部に試料を80μl塗布した。2時間後、70%エタノールで皮膚表面上の試料を拭き取り、健康線用ランプ(東芝製、SE20)を6本用意し、1回の照射量が1MED以下となるように調整してUV−B光の照射を行い、その直後に試料を塗布した。この操作を週5回、16週間にわたって行った。照射のエネルギー料をUV−Radiometer(TOKYO OPTICAL社製、UVR−305/365D)を用いて測定した。試験終了後しわの度数を肉眼により下記基準(しわ指数)で評価した。試験結果は評価点の平均で示した。
【0023】
(3)荒れ肌改善効果の測定試験法
下脚に荒れ肌を有する中高年被験者20名を対象として4週間連続塗布効果を調べた。被験者の左側下脚試験部位に1日2回約1gの試料を塗布し、試験開始前及び終了後の皮膚の状態を下記の判定基準により判定した。右側下脚は試料を塗布せず対照とした。
試験前後の試験部位と対照部位の判定結果を比較し、皮膚乾燥度が2段階以上改善された場合(例えば;+→−,++→±)を「有効」、1段階改善された場合を「やや有効」、変化がなかった場合を「無効」とした。試験結果は「有効」「やや有効」となった被験者の人数で示した。
【0024】
(4)官能試験
被験者20名が試料を10日間連用した後の試料の特性を評価した。評価は、平滑性、美白効果、弾力性のアンケート項目に対し、「皮膚が滑らかになった」、「美白効果が感じられた」、「皮膚に張りが生じた」と回答した人数で示した。
【0025】
実施例1〜12,比較例1〜10
表皮細胞セラミド合成促進物質と、ビフェニル化合物を表1の組成において配合し、下記の調製方法に基づいてスキンクリームを調製した。各々について前記の試験を実施し、その結果を表2、表3に示した。
組成
【0026】
【表1】
【0027】
【表2】
【0028】
【表3】
【0029】
調製方法
(A)(B)を70℃にて均一に溶解し、(A)を攪拌しながら(B)を(A)に注入して乳化分散した後、攪拌しながら温度50℃まで冷却して(C)を加え、温度30℃まで冷却して調製する。
【0030】
特性
本発明の実施例1〜12のスキンクリームは、前記諸試験において良好な結果を示した。一方、比較例1〜10のスキンクリームは、十分な効果が認められず、本発明の実施例に比べて劣っていた。
【0031】
実施例13[スキンローション]
表4の組成により本発明のスキンローションを下記の製法によって調製した。
組成
【0032】
【表4】
【0033】
調製法
(A),(B)の各成分をそれぞれ混合溶解し、(B)を(A)に加えて混合攪拌して調製した。
【0034】
特性
この実施例13のスキンローションは、前記諸試験において良好な結果を示した。
【0035】
【発明の効果】
以上記載のごとく、本発明が、特に美白効果に優れ、さらに優れた肌荒れ防止効果、老化防止効果及び美肌効果を発現し、皮膚を健やかに保つことのできる優れた皮膚化粧料を提供することは明らかである。
[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a skin cosmetic that is particularly excellent in whitening effect, and that exhibits excellent skin roughness preventing effect, anti-aging effect and skin beautifying effect, and can keep skin healthy.
[0002]
[Prior Art and Problems to be Solved by the Invention]
Conventionally, cosmetics intended for prevention and treatment of skin spots, freckles, and the like have been formulated with L-ascorbic acid and its derivatives, hydroquinone derivatives such as arbutin, and pyrones such as kojic acid.
[0003]
These substances have effects such as inhibition of melanin production and light color bleaching of the produced melanin, and are widely known as substances having a whitening effect. However, in these substances, for example, L-ascorbic acid and its derivatives often meet with insufficient storage stability, and the anti-inflammatory effect by ultraviolet rays is often not sufficiently observed. Hydroquinone derivatives and pyrones have problems such as insufficient safety. As described above, it has been difficult to obtain a cosmetic material that is comprehensively excellent in whitening, such as a melanin production inhibitory effect, a melanin lightening effect, an inflammation prevention effect, and safety.
[0004]
On the other hand, it is known that specific biphenyl compounds have a tyrosinase activity inhibitory effect and a melanin production inhibitory effect (Japanese Patent Laid-Open Nos. 6-145040 and 7-25743). However, even when this was blended alone, the whitening effect was not satisfactory.
[0005]
Therefore, as a result of intensive studies, the present inventors have found that a skin cosmetic preparation containing an epidermal cell ceramide synthesis promoting substance and a specific biphenyl compound suppresses the production of melanin due to UV damage and synthesizes ceramide, a lipid of the epidermis. It was found that it promotes skin metabolism and, as a result, promotes melanin excretion and exhibits an excellent whitening effect. Furthermore, the present inventors have found that it exhibits excellent skin roughness prevention effects, anti-aging effects, and skin beautifying effects such as preventing skin dryness and preventing skin roughness and wrinkles, and has completed the present invention.
[0006]
An object of the present invention is to provide a skin cosmetic that is particularly excellent in whitening effect, and that exhibits excellent skin roughness prevention effect, anti-aging effect and skin beautifying effect, and can keep skin healthy.
[0007]
[Means for Solving the Problems]
The present invention that achieves the above object is a skin cosmetic containing an epidermal cell ceramide synthesis promoting substance and at least one selected from biphenyl compounds represented by the following general formulas (1) and (2).
[0008]
[Chemical 3]
[0009]
(However, R 1 is a substituent of CH 3 , C 2 H 5 , C 3 H 7 , CH 2 OH, C 3 H 6 OH, CH 2 CH═CH 2 )
[0010]
[Formula 4]
[0011]
(However, R 2 is a hydrogen atom or a linear or branched saturated hydrocarbon group having 1 to 8 carbon atoms.)
[0012]
DETAILED DESCRIPTION OF THE INVENTION
Hereinafter, embodiments of the present invention will be described in detail.
[0013]
Examples of nicotinic acid and derivatives thereof as epidermal cell ceramide synthesis promoting substances used in the present invention include nicotinic acid, nicotinic acid amide, methyl nicotinic acid, ethyl nicotinic acid, benzyl nicotinic acid, tocopherol nicotinate, and nitricate citrate. Examples of nicotinyl alcohol and salts thereof include nicotinyl alcohol and nicotinyl alcohol tartrate, but are not limited thereto.
[0014]
The content of the epidermal cell ceramide synthesis promoting substance is preferably 0.001 to 20.0% by weight based on the total amount of prescription ingredients of cosmetics.
The biphenyl compound used in the present invention is a known substance, and specific examples thereof include dehydrodichloroeosol, dehydrodioigenol, tetrahydromagnolol and the like (Journal of Organic Chemistry, 28, 1048, 1963). : Journal of the Chemical Society of Japan, Vol. 87, No. 6, 603, 1966).
[0016]
The blending amount is preferably 0.0001 to 20% by weight in the total amount of the cosmetic.
[0017]
In the cosmetic of the present invention, in addition to the above-mentioned raw materials, pigments, fragrances, preservatives, surfactants, antioxidants, moisturizers and the like can be appropriately blended within the scope of achieving the object of the present invention. .
[0018]
Examples of the dosage form of the cosmetic of the present invention include creams, emulsions, lotions and packs. For example, in the case of a milky lotion, this cosmetic can be produced by an ordinary method in which an oil phase and an aqueous phase are each dissolved by heating and emulsified and cooled.
[0019]
【Example】
Hereinafter, the present invention will be described in detail based on examples and comparative examples. In addition,% shown in an Example is weight%. The skin lightness recovery test method, wrinkle formation suppression test method (anti-aging effect), rough skin improvement effect measurement method, and sensory test (skin-beautifying effect) described in Examples are as follows.
[0020]
In addition, the name of the biphenyl compound in an Example is described as follows with the difference of R < 1 >, R < 2 > of the said general formula.
Biphenyl compound 1 (R 1 ; CH 3 ), biphenyl compound 2 (R 1 ; C 2 H 5 ), biphenyl compound 3 (R 1 ; C 3 H 7 ), biphenyl compound 4 (R 1 ; CH 2 OH), biphenyl Compound 5 (R 1 ; C 3 H 6 OH), biphenyl compound 6 (R 1 ; CH 2 CH═CH 2 ), biphenyl compound 7 (R 2 ; CH 3 ), biphenyl compound 8 (R 2 ; C 2 H 5 ), Biphenyl compound 9 (R 2 ; C 3 H 7 ), biphenyl compound 10 (R 2 ; iso-C 3 H 7 ), biphenyl compound 11 (R 2 ; C 8 H 17 ), biphenyl compound 12 (R 2 ; H).
[0021]
(1) Skin lightness recovery test method The back skin of 20 subjects was irradiated with UV rays in the UV-B region twice as much as the minimum erythema amount, the sample application site and the non-application site were set, and the standard brightness of each skin ( (V 0 value, V 0 ′ value) were measured. Subsequently, after continuously applying the sample to the application site twice a day for 15 weeks, the brightness of the skin at the application site and non-application site after 3, 6, 9, 12, 15 weeks (Vn value, Vn ′ value) The skin color recovery was evaluated according to the following criteria.
The lightness of the skin (Munsell color system V value) was calculated from X, Y, and Z values obtained by measurement with a high-speed spectral colorimeter. The evaluation was shown as an average value of evaluation points after 6 weeks for 20 subjects.
[0022]
(2) Wrinkle formation inhibition test using hairless mice Ten hairless mice (HR / ICR, 6 weeks of age at the start of the experiment) were used, and 80 μl of the sample was applied to the back. After 2 hours, wipe off the sample on the skin surface with 70% ethanol, prepare 6 health line lamps (Toshiba, SE20), and adjust each dose to 1 MED or less, UV-B The sample was applied immediately after light irradiation. This operation was performed 5 times a week for 16 weeks. The irradiation energy charge was measured using a UV-Radiometer (manufactured by TOKYO OPTICAL, UVR-305 / 365D). After the test, the frequency of wrinkles was evaluated with the naked eye according to the following criteria (wrinkle index). The test result was shown by the average of evaluation points.
[0023]
(3) Measurement test method for effect of improving rough skin The effect of continuous application was examined for 20 middle-aged and older subjects having rough skin on the lower leg for 4 weeks. About 1 g of a sample was applied to the subject's left lower leg test site twice a day, and the skin condition before and after the test was determined according to the following criteria. The lower right leg was used as a control with no sample applied.
The judgment results of the test site before and after the test and the control site are compared, and when the skin dryness is improved by two or more levels (for example, + → −, ++ → ±) is “effective”, and when the level is improved by 1 level, “Slightly effective” and “invalid” when there was no change. The test result was shown by the number of subjects who became “effective” and “slightly effective”.
[0024]
(4) Sensory test The characteristics of the sample after 20 test subjects were used for 10 days were evaluated. The evaluation was shown by the number of respondents who answered “Skin became smooth”, “I felt a whitening effect”, and “Skin was stretched” for questionnaire items on smoothness, whitening effect, and elasticity. .
[0025]
Examples 1-12, Comparative Examples 1-10
An epidermal cell ceramide synthesis promoting substance and a biphenyl compound were blended in the composition shown in Table 1, and a skin cream was prepared based on the following preparation method. The above test was carried out for each, and the results are shown in Tables 2 and 3.
Composition [0026]
[Table 1]
[0027]
[Table 2]
[0028]
[Table 3]
[0029]
Preparation method (A) (B) is uniformly dissolved at 70 ° C., and (B) is injected into (A) while emulsifying and dispersing while stirring (A), and then cooled to 50 ° C. with stirring. (C) is added and cooled to a temperature of 30 ° C.
[0030]
Characteristics The skin creams of Examples 1 to 12 of the present invention showed good results in the above tests. On the other hand, the skin creams of Comparative Examples 1 to 10 were inferior to the examples of the present invention because sufficient effects were not recognized.
[0031]
Example 13 [Skin Lotion]
The skin lotion of the present invention was prepared by the following production method according to the composition shown in Table 4.
Composition [0032]
[Table 4]
[0033]
The components of preparation methods (A) and (B) were mixed and dissolved, and (B) was added to (A) and mixed and stirred.
[0034]
Properties The skin lotion of Example 13 showed good results in the above tests.
[0035]
【The invention's effect】
As described above, the present invention provides an excellent skin cosmetic that is particularly excellent in whitening effect, and that exhibits excellent skin roughness prevention effect, anti-aging effect and skin beautifying effect, and can keep the skin healthy. it is obvious.

Claims (1)

ニコチン酸、ニコチン酸アミド、メチルニコチン酸、エチルニコチン酸、ベンジルニコチン酸、ニコチン酸トコフェロール、クエン酸ニカメタート、ニコチニルアルコール及びその塩からなる群から選ばれる少なくとも1種の表皮細胞セラミド合成促進物質と、下記一般式(1)及び(2)で表されるビフェニル化合物から選ばれる少なくとも一種を含有する皮膚化粧料。
At least one epidermal cell ceramide synthesis promoter selected from the group consisting of nicotinic acid, nicotinic acid amide, methyl nicotinic acid, ethyl nicotinic acid, benzyl nicotinic acid, tocopherol nicotinate, nicamethate citrate, nicotinyl alcohol and salts thereof ; A skin cosmetic containing at least one selected from biphenyl compounds represented by the following general formulas (1) and (2).
JP01741097A 1997-01-14 1997-01-14 Skin cosmetics Expired - Lifetime JP3632164B2 (en)

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US6309657B2 (en) 1999-02-12 2001-10-30 The Procter & Gamble Company Cosmetic compositions
US6455055B1 (en) 1999-02-12 2002-09-24 The Procter & Gamble Company Cosmetic compositions
US6224888B1 (en) 1999-02-12 2001-05-01 The Procter & Gamble Company Cosmetic compositions
JP2005015450A (en) * 2003-06-30 2005-01-20 Kanebo Cosmetics Inc Skin cosmetic
AU2006233101B2 (en) * 2005-02-23 2011-09-01 Arbiser, Jack Honokiol derivatives for the treatment of proliferative disorders

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