JPH05163131A - Skin cosmetic - Google Patents

Skin cosmetic

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Publication number
JPH05163131A
JPH05163131A JP35249691A JP35249691A JPH05163131A JP H05163131 A JPH05163131 A JP H05163131A JP 35249691 A JP35249691 A JP 35249691A JP 35249691 A JP35249691 A JP 35249691A JP H05163131 A JPH05163131 A JP H05163131A
Authority
JP
Japan
Prior art keywords
skin
cosmetic
action
astringent
skin cosmetic
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.)
Granted
Application number
JP35249691A
Other languages
Japanese (ja)
Other versions
JP2902842B2 (en
Inventor
Takeshi Sakamaki
剛 坂巻
Mitsuo Kondo
光男 近藤
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Kanebo Ltd
Original Assignee
Kanebo Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Kanebo Ltd filed Critical Kanebo Ltd
Priority to JP35249691A priority Critical patent/JP2902842B2/en
Publication of JPH05163131A publication Critical patent/JPH05163131A/en
Application granted granted Critical
Publication of JP2902842B2 publication Critical patent/JP2902842B2/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Abstract

PURPOSE:To obtain a skin cosmetic having improved stability with time, excellently astringing action and conditioning and protecting action on skin by using both a polyphenol compound and an alkylglycoside. CONSTITUTION:A skin cosmetic using both a polyphenol (e.g. tannin of Japanese persimmon or pyrogallol) and an alkylglycoside (e.g. dodecyl-beta-D-maltoside) having excellently pharmaceutically manufacturing function without forming a complex between both molecules. For example, toilet lotion, milky lotion, cream, pack, cleansing, face washing agent, make-up base, foundation, lip cream or lipstick may be cited as the cosmetic.

Description

【発明の詳細な説明】Detailed Description of the Invention

【0001】[0001]

【産業上の利用分野】本発明は、経日安定性が良好で、
優れた収斂作用及び整肌・保護作用を有する皮膚化粧料
に関する。
BACKGROUND OF THE INVENTION The present invention has good stability over time,
The present invention relates to a skin cosmetic having excellent astringent action and skin conditioning / protecting action.

【0002】[0002]

【従来の技術及び発明が解決しようとする課題】従来、
皮膚化粧料に、皮膚に対する収斂作用及び整肌・保護作
用発現の有効成分として亜鉛化合物(例えば、パラフェ
ノールスルホン酸亜鉛,酸化亜鉛)及びアルミニウム化
合物(例えば、塩化アルミニウム、塩基性塩化アルミニ
ウム等)が配合されるが、これらは皮膚刺激を伴うか、
効果が不充分である等の問題があり、満足のいくものが
得られなかった。
2. Description of the Related Art Conventionally, the problems to be solved by the invention
Zinc compounds (for example, zinc paraphenolsulfonate, zinc oxide) and aluminum compounds (for example, aluminum chloride, basic aluminum chloride, etc.) as active ingredients for astringent action and skin conditioning / protecting action on skin are contained in skin cosmetics. Are included, but are they accompanied by skin irritation?
There was a problem that the effect was insufficient, etc., and a satisfactory product could not be obtained.

【0003】このような状況に鑑み、本発明者は、柿に
含有している縮合型タンニンが極めて優れた収斂作用及
び整肌・保護作用を有し、皮膚刺激がなく、皮膚化粧料
に配合するのに非常に適した有効成分であることを見出
した(特開昭61−236713号公報)。
In view of such a situation, the present inventor has found that the condensed tannin contained in persimmon has an extremely excellent astringent action and skin conditioning / protecting action, and has no skin irritation and is incorporated into a skin cosmetic composition. It was found that the active ingredient is very suitable for the treatment (Japanese Patent Laid-Open No. 61-236713).

【0004】一方、ポリオキシエチレン付加型非イオン
界面活性剤は、ポリオキシエチレン鎖長及びアルキル鎖
長を任意に設定することができるので、乳化剤、可溶化
剤、分散剤として皮膚化粧料に汎用されている。しか
し、ポリオキシエチレン付加型非イオン界面活性剤とポ
リフェノール化合物の組合せから成る皮膚化粧料を製造
するとき、両分子間の相互作用による複合体が不溶物と
して生成するために、皮膚化粧料としての製剤機能が損
なわれ、同時に、皮膚に対する収斂作用及び整肌・保護
作用も充分に満足されないという問題を持つことが判明
した。
On the other hand, the polyoxyethylene-addition type nonionic surfactant can be arbitrarily set in the polyoxyethylene chain length and the alkyl chain length, and is therefore widely used in skin cosmetics as an emulsifier, a solubilizer and a dispersant. Has been done. However, when a skin cosmetic comprising a combination of a polyoxyethylene addition type nonionic surfactant and a polyphenol compound is produced, a complex is produced as an insoluble substance due to an interaction between both molecules, and therefore, as a skin cosmetic. It was found that the formulation function is impaired, and at the same time, the astringent action on the skin and the skin conditioning / protecting action are not sufficiently satisfied.

【0005】そこで、本発明者等は、この欠点を改良せ
んとして鋭意検討した結果、ポリフェノール化合物とア
ルキルグリコシドを組合せて使用するとき、両分子間で
複合体を形成することなく、優れた製剤機能を有する皮
膚化粧料が得られることを見出し、本発明を完成した。
The inventors of the present invention have made extensive studies as a remedy for this drawback. As a result, when a polyphenol compound and an alkyl glycoside are used in combination, an excellent formulation function is achieved without forming a complex between both molecules. It was found that a skin cosmetic having the following can be obtained, and the present invention was completed.

【0006】即ち、本発明は、経日安定性が良好で、優
れた収斂作用及び整肌・保護作用を有する皮膚化粧料を
提供することを目的とするものである。
That is, an object of the present invention is to provide a skin cosmetic having good stability over time and having excellent astringent action and skin conditioning / protecting action.

【0007】[0007]

【課題を解決するための手段】上記の目的を達成するた
めに、本発明の皮膚化粧料は次のような構成をとる。即
ち、ポリフェノール化合物とアルキルグリコシドとを含
有することを特徴とする皮膚化粧料である。
In order to achieve the above object, the skin cosmetic of the present invention has the following constitution. That is, it is a skin cosmetic containing a polyphenol compound and an alkyl glycoside.

【0008】本発明におけるポリフェノール化合物とし
て、例えば、没食子酸、没食子酸エステル(プロピルエ
ステル、イソアミルエステル、オクチルエステル、ドデ
シルエステル等)、ピロガロール、フロログリシン、カ
テキン、エピカテキン、ガロカテキン、カテキンガレー
ト、ガロカテキンガレート、エピカテキンガレート、エ
ピガロカテキンガレート、エピガロカテキン、グルコガ
リン、プロアントシアニジン及びそのポリマー、フラボ
ン類(例えば、ルチン、クエルセチン、クエルセタギ
ン、クエルセタギチン、ゴシペチン等)、エラグ酸、ペ
ンタ−O−ガロイルグルコース、タンニン酸、ガロタン
ニン(シャクヤク抽出物のタンニン)、エラジタンニン
(ゲンノショウコ、アカメガシワ、ザクロ皮、サンシュ
ユ、詞子等から抽出した各タンニン)、縮合型タンニン
(渋柿、茶、桂皮、阿仙薬、地楡茶等から抽出した各タ
ンニン)、ウラジロガシ皮、ミズナラ皮、同堅果等から
抽出した各タンニン等を挙げることができる。
Examples of the polyphenol compound in the present invention include gallic acid, gallic acid esters (propyl ester, isoamyl ester, octyl ester, dodecyl ester, etc.), pyrogallol, phloroglysin, catechin, epicatechin, gallocatechin, catechin gallate, gallocatechin. Galate, epicatechin gallate, epigallocatechin gallate, epigallocatechin, glucogallin, proanthocyanidins and polymers thereof, flavones (for example, rutin, quercetin, quercetagin, quercetaginine, gosipetin, etc.), ellagic acid, penta-O-galloyl glucose , Tannic acid, gallotannin (tannin of peony extract), ellagitannin (genoshoko, red-skinned wrinkles, pomegranate skin, sanshuyu, koshiko, etc.) Each tannin) has, condensed tannins (astringent persimmon, tea, cinnamon, Uncaria gambir Roxburgh, each tannin extracted from Chinire tea, etc.), Quercus salicina bark, oak bark, may be mentioned the tannin or the like extracted from the nuts and the like.

【0009】また、本発明におけるアルキルグリコシド
とは、炭素数8〜22のアルキル基又はアルケニル基と
1〜5個の炭素数5〜6の還元糖に由来する糖部から構
成されるもので、単糖類ではグルコース、ガラクトー
ス、キシロース、フラクトース、マンノース、リキソー
ス、アピビノース等が、2糖以上ではマルトース、キシ
ロビオース、イソマンノース、ラクトース、スクロー
ス、ラフィノース、マルトトリオース等が挙げられる。
そして、これらのうち特に好ましい原料は、コスト面か
らグルコース、フラクトース、マルトース、スクロース
である。そして、糖部が2個以上から構成されたアルキ
ルグリコシドの場合、その糖鎖の結合様式は、1−2、
1−3、1−4、1−6結合、更にα,β−ピラノシ
ド、又はフラノシド結合及びこれらが任意に混合された
ものが可能である。従って、例えばデシル−β−D−グ
リコシド、テトラデシル−α−D−フルクトシド、ドデ
シル−β−D−マルトシド、オクタデシル−α−D−ス
クロシド等が挙げられる。
The alkyl glycoside in the present invention is composed of an alkyl group or an alkenyl group having 8 to 22 carbon atoms and a sugar moiety derived from 1 to 5 reducing sugars having 5 to 6 carbon atoms. Examples of monosaccharides include glucose, galactose, xylose, fructose, mannose, lyxose, and apibinose, and examples of disaccharides or more include maltose, xylobiose, isomannose, lactose, sucrose, raffinose, maltotriose, and the like.
Of these, particularly preferable raw materials are glucose, fructose, maltose, and sucrose from the viewpoint of cost. And, in the case of an alkyl glycoside composed of two or more sugar moieties, the binding mode of the sugar chain is 1-2,
It is possible to use 1-3, 1-4, 1-6 bonds, further α, β-pyranoside bonds, or furanoside bonds and any mixture thereof. Therefore, for example, decyl-β-D-glycoside, tetradecyl-α-D-fructoside, dodecyl-β-D-maltoside, octadecyl-α-D-sucroside and the like can be mentioned.

【0010】本発明の皮膚化粧料としては、例えば、化
粧水、乳液、クリーム、パック、クレンジング、洗顔
料、メイクアップベース、ファンデーション、リップク
リーム、口紅等が挙げられるが、特に、これらに限定さ
れず、他の皮膚化粧料及び医薬部外品に適用することが
できる。
The skin cosmetics of the present invention include, for example, lotion, emulsion, cream, pack, cleansing, face wash, makeup base, foundation, lip balm, lipstick, etc., but are not particularly limited thereto. Instead, it can be applied to other skin cosmetics and quasi drugs.

【0011】[0011]

【実施例】実施例によって本発明を更に詳細に説明す
る。実施例に示す部とは、重量部を意味する。
The present invention will be described in more detail by way of examples. The parts shown in the examples mean parts by weight.

【0012】尚、実施例を詳述するに先立ち、そこで使
用する試験方法について述べる。
Before describing the embodiments in detail, the test method used therein will be described.

【0013】1.経日安定性試験方法 実施例及び比較例に示した皮膚化粧料を製造直後及び4
0℃の恒温槽に密閉容器中に6ケ月間放置後(加速試
験)、外観を肉眼にて評価した。
1. Method for testing stability over time Immediately after the production of the skin cosmetics shown in Examples and Comparative Examples and 4
After leaving it in a closed container in a thermostat at 0 ° C. for 6 months (acceleration test), the appearance was visually evaluated.

【0014】2.有用性(皮膚への収斂作用及び整肌・
保護作用)試験方法 実施例及び比較例に示した皮膚化粧料の皮膚に対する収
斂作用に関し、荒れ肌性の者から選択された専門検査員
10名が、1日1回、7日間連続して試料の皮膚化粧料
0.3gを肌に均一に塗布して、実用テストを行った
後、8日目の皮膚の状態を判断し、次の基準で評価し
た。 5:皮膚の収斂作用は大変良い。 4:皮膚の収斂性はやや良い。 3:皮膚の収斂性は普通。 2:皮膚の収斂性はやや悪い。 1:皮膚の収斂性は悪い。 さらに、荒肌改善性の視点から整肌・保護作用に関して
も上記と同様に判断し、同様の5段階基準で評価した。
尚、10人の専門検査員による評価点の平均値を各試料
の得点とした。
2. Utility (astringent effect on skin and skin conditioning
Protective Effect) Test Method Regarding the astringent effect of the skin cosmetics shown in Examples and Comparative Examples on the skin, 10 professional inspectors selected from those who have rough skin are tested once a day for 7 consecutive days. After 0.3 g of skin cosmetics was uniformly applied to the skin and a practical test was performed, the skin condition on the 8th day was judged and evaluated according to the following criteria. 5: The astringent action of the skin is very good. 4: The astringency of the skin is slightly good. 3: Normal astringency of the skin. 2: The astringency of the skin is rather poor. 1: Skin has poor astringency. Further, from the viewpoint of improving rough skin, the skin conditioning / protecting action was also judged in the same manner as above, and evaluated on the basis of the same 5 grades.
The average value of the evaluation points by 10 professional inspectors was used as the score of each sample.

【0015】実施例1(収斂化粧水) (1) 処方 エタノール 10.0部 柿タンニン(縮合型) 0.5部 クエン酸ナトリウム 0.05部 クエン酸 0.05部 エリソルビン酸 0.4部 エデト酸二ナトリウム 0.1部 ドデシル−β−D−マルトシド 0.4部 香料 0.05部 精製水 88.45部 (2) 製造法Example 1 (Astringent lotion) (1) Formulation Ethanol 10.0 parts Persimmon tannin (condensation type) 0.5 parts Sodium citrate 0.05 parts Citric acid 0.05 parts Erythorbic acid 0.4 parts EDET Disodium acid salt 0.1 part Dodecyl-β-D-maltoside 0.4 part Perfume 0.05 part Purified water 88.45 part (2) Production method

【0016】上記成分に成分〜を溶解し、この溶
液に成分に成分及び成分を溶解したものを加え、
混合によって均一系にして、本発明の収斂化粧水を得
た。この収斂化粧水を試料として前記諸試験を実施し、
得られた結果を表1に示す。皮膚の収斂作用及び整肌・
保護作用(荒肌改善性)は大変良く、6ケ月間放置後の
外観も沈澱物が生じることなく透明で、化粧料としての
製剤機能を有していた。
Ingredients (1) to (5) are dissolved in the above ingredients, and the solution and the ingredients and the ingredients are dissolved,
A uniform system was obtained by mixing to obtain the astringent lotion of the present invention. Performed the above-mentioned tests using this astringent lotion as a sample,
The results obtained are shown in Table 1. Astringent action and skin conditioning
The protective action (improvement of rough skin) was very good, and the appearance after standing for 6 months was transparent with no precipitates and had a formulation function as a cosmetic.

【0017】[0017]

【表1】 [Table 1]

【0018】比較例1 実施例1に記載の処方成分の代わりにポリオキシエチ
レン(20モル)ソルビタンオレートを用いた他は、同
様の処方及び製造法によって比較例1の収斂化粧水を得
た。これを試料として前記諸試験を実施し、得られた結
果を表1に示す。試料の製造直後、試料に白濁が生じる
と同時に、香料が浮遊ないし分離した。皮膚の収斂作用
が悪く、整肌・保護作用も、やや悪かった。また、6ケ
月間放置後の外観は、2層分離状態を呈し、白濁物も残
存して、化粧料としての製剤機能を失っていた。
Comparative Example 1 Astringent lotion of Comparative Example 1 was obtained by the same formulation and manufacturing method except that polyoxyethylene (20 mol) sorbitan oleate was used in place of the formulation components described in Example 1. The above-mentioned various tests were carried out using this as a sample, and the obtained results are shown in Table 1. Immediately after the preparation of the sample, the sample became cloudy and the perfume floated or separated. The astringent effect on the skin was poor, and the skin conditioning / protecting effect was also poor. In addition, the appearance after being left for 6 months was in a two-layer separated state, white turbidity remained, and the formulation function as a cosmetic was lost.

【0019】実施例2(クリーム) (1) 処方 1 スクワラン 25.0部 2 セチルアルコール 3.0部 3 トリ−2−エチルヘキサン酸グリセリン 5.0部 4 デシルグルコシド(β/α=1) 1.0部 5 テトラデシルグルコシド(β/α=1) 1.0部 6 ステアリン酸 0.5部 7 キサンタンガム 0.1部 8 ドデシルマルトシド(β/α=3) 0.7部 9 パラオキシ安息香酸メチル 0.2部 10 エデト酸二ナトリウム 0.1部 11 クエン酸ナトリウム 0.1部 12 L−アスコルビン酸 0.1部 13 タンニン酸(加水分解型) 0.1部 14 香料 0.1部 15 精製水 63.0部 (2) 製造法Example 2 (Cream) (1) Formulation 1 Squalane 25.0 parts 2 Cetyl alcohol 3.0 parts 3 Glycerin tri-2-ethylhexanoate 5.0 parts 4 Decyl glucoside (β / α = 1) 1 0.0 part 5 tetradecyl glucoside (β / α = 1) 1.0 part 6 stearic acid 0.5 part 7 xanthan gum 0.1 part 8 dodecyl maltoside (β / α = 3) 0.7 part 9 paraoxybenzoic acid Methyl 0.2 part 10 Disodium edetate 0.1 part 11 Sodium citrate 0.1 part 12 L-Ascorbic acid 0.1 part 13 Tannic acid (hydrolyzable) 0.1 part 14 Perfume 0.1 part 15 Purified water 63.0 parts (2) Manufacturing method

【0020】上記成分1〜5を約80℃にて均一に溶解す
る(溶液I) 。上記成分の水溶性成分7〜9及び15の一
部を約80℃にて均一に溶解する(溶液II)。上記成分15
の残部に10〜13を常温にて均一に溶解する(溶液III
)。次に、溶液Iをホモジナイザーで攪拌しながら、
溶液IIを添加し、乳化した後、冷却する。尚、その冷却
過程の70℃で成分14を添加して30℃まで降温後、溶液II
Iを添加し、攪拌を停止した。このようにして得られた
クリームを試料として前記諸試験を実施し、得られた結
果を表1に示す。皮膚の収斂作用及び整肌・保護作用は
やや良好で、6ケ月間放置後の外観もきめが良く均一
で、化粧料としての製剤機能を有していた。
The above components 1 to 5 are uniformly dissolved at about 80 ° C. (solution I). A part of the water-soluble components 7 to 9 and 15 of the above components are uniformly dissolved at about 80 ° C. (Solution II). Ingredient 15
Dissolve 10 to 13 uniformly in the rest of the solution at room temperature (Solution III
). Next, while stirring Solution I with a homogenizer,
Solution II is added, emulsified and cooled. In the cooling process, component 14 was added at 70 ° C and the temperature was lowered to 30 ° C.
I was added and stirring was stopped. The creams thus obtained were used as samples for the above-mentioned tests, and the results are shown in Table 1. The skin astringent action and skin conditioning / protecting action were slightly good, and the appearance after being left for 6 months had a good texture and was uniform, and had a formulation function as a cosmetic.

【0021】比較例2 実施例2に記載の処方成分の代わりにポリオキシエチ
レン(2モル)セチルエーテルを、成分及びの代わ
りにポリオキシエチレン(20モル)オレイルエーテル
を用いた他は、同様の処方及び製造法によって比較例2
のクリームを得た。これを試料として前記諸試験を実施
し、得られた結果を表1に示す。試料の製造直後の外観
は、クリームのきめが悪く、乳化不良であった。その製
剤の有効性を試験したところ、皮膚の収斂作用は悪く、
整肌・保護作用も悪かった。また、6ケ月間放置後の外
観は、水相と油相が分離し、化粧料としての製剤機能を
失っていた。
Comparative Example 2 The same as Example 2 except that polyoxyethylene (2 mol) cetyl ether was used in place of the formulation component and polyoxyethylene (20 mol) oleyl ether was used in place of component and. Comparative Example 2 depending on the formulation and manufacturing method
Got the cream. The above-mentioned various tests were carried out using this as a sample, and the obtained results are shown in Table 1. As for the appearance of the sample immediately after the production, the cream had a bad texture and poor emulsification. When the efficacy of the formulation was tested, the skin astringent effect was poor,
The skin conditioning and protective effects were also poor. In addition, the appearance after being left for 6 months was such that the aqueous phase and the oil phase were separated and the formulation function as a cosmetic was lost.

【0022】[0022]

【発明の効果】以上記載のごとく、本発明の皮膚化粧料
は、経日安定性が良好で、極めて優れた収斂作用及び整
肌・保護作用を有するものである。
EFFECTS OF THE INVENTION As described above, the skin cosmetic of the present invention has good stability over time and has a very excellent astringent action and skin conditioning / protecting action.

───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.5 識別記号 庁内整理番号 FI 技術表示箇所 A61K 7/00 W 8615−4C ─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 5 Identification code Internal reference number FI technical display area A61K 7/00 W 8615-4C

Claims (1)

【特許請求の範囲】[Claims] 【請求項1】 ポリフェノール化合物とアルキルグリコ
シドとを含有することを特徴とする皮膚化粧料。
1. A skin cosmetic containing a polyphenol compound and an alkyl glycoside.
JP35249691A 1991-12-13 1991-12-13 Skin cosmetics Expired - Lifetime JP2902842B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP35249691A JP2902842B2 (en) 1991-12-13 1991-12-13 Skin cosmetics

Applications Claiming Priority (1)

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Cited By (9)

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WO1994029404A1 (en) * 1993-06-14 1994-12-22 Berkem Polyphenol derivative compositions and preparation thereof
JPH10306011A (en) * 1997-05-07 1998-11-17 Pola Chem Ind Inc Ununiformity improving cosmetic
EP0998898A1 (en) * 1998-10-01 2000-05-10 Beiersdorf Aktiengesellschaft Use of alkylglycosides for stabilizing of flavones, flavanones or flavonoids, and synergistic mixtures, cosmetic and dermatological preparations containing them
JP2001270881A (en) * 2000-03-24 2001-10-02 Kyowa Hakko Kogyo Co Ltd Proanthocyanidin-containing composition
KR100367563B1 (en) * 1998-12-16 2003-02-19 주식회사 참 존 Whitening cosmetics containing persimmon leaf extract
US6685970B1 (en) 1999-09-21 2004-02-03 Kyowa Hakko Kogyo Co., Ltd. Compositions containing proanthocyanidin and a vitamin B6 derivative or a salt thereof
US8114829B2 (en) 2005-02-22 2012-02-14 Human Matrix Sciences, Llc Elastin protective polyphenolics and methods of using the same
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US8642578B2 (en) * 2005-03-29 2014-02-04 Human Matrix Sciences, Llc Elastin protective polyphenolics and methods of using the same

Cited By (16)

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FR2706478A1 (en) * 1993-06-14 1994-12-23 Ovi Sa Compositions of phenolic derivatives, their preparation and their applications as antioxidants.
WO1994029404A1 (en) * 1993-06-14 1994-12-22 Berkem Polyphenol derivative compositions and preparation thereof
JPH10306011A (en) * 1997-05-07 1998-11-17 Pola Chem Ind Inc Ununiformity improving cosmetic
EP0998898A1 (en) * 1998-10-01 2000-05-10 Beiersdorf Aktiengesellschaft Use of alkylglycosides for stabilizing of flavones, flavanones or flavonoids, and synergistic mixtures, cosmetic and dermatological preparations containing them
KR100367563B1 (en) * 1998-12-16 2003-02-19 주식회사 참 존 Whitening cosmetics containing persimmon leaf extract
US6685970B1 (en) 1999-09-21 2004-02-03 Kyowa Hakko Kogyo Co., Ltd. Compositions containing proanthocyanidin and a vitamin B6 derivative or a salt thereof
US6926914B2 (en) 2000-03-24 2005-08-09 Kyowa Hakko Kogyo Co., Ltd. Proanthocyanidin-containing composition
US6506419B2 (en) 2000-03-24 2003-01-14 Kyowa Hakko Kogyo Co., Ltd Proanthocyanidin-containing composition
JP2001270881A (en) * 2000-03-24 2001-10-02 Kyowa Hakko Kogyo Co Ltd Proanthocyanidin-containing composition
JP4574788B2 (en) * 2000-03-24 2010-11-04 協和発酵バイオ株式会社 Proanthocyanidin-containing composition
US8114829B2 (en) 2005-02-22 2012-02-14 Human Matrix Sciences, Llc Elastin protective polyphenolics and methods of using the same
US8642578B2 (en) * 2005-03-29 2014-02-04 Human Matrix Sciences, Llc Elastin protective polyphenolics and methods of using the same
US9254300B2 (en) 2005-03-29 2016-02-09 Human Matrix Sciences, Llc Elastin protective polyphenolics and methods of using the same
US10004779B2 (en) 2005-03-29 2018-06-26 Human Matrix Services, LLC Elastin protective polyphenolics and methods of using the same
FR2978040A1 (en) * 2011-07-22 2013-01-25 Oreal METHOD FOR TREATING HUMAN TRANSPIRATION USING POLYPHENOLS AND CATALYTIC ENZYMATIC AND / OR CHEMICAL OXIDATION SYSTEM
WO2013013901A1 (en) * 2011-07-22 2013-01-31 L'oreal Process for treating human perspiration using polyphenols and an enzymatic and/or chemical catalytic oxidation system

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