JP4227332B2 - Pyridoxine derivatives, and skin cosmetics and hair cosmetics containing the pyridoxine derivatives - Google Patents
Pyridoxine derivatives, and skin cosmetics and hair cosmetics containing the pyridoxine derivatives Download PDFInfo
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- JP4227332B2 JP4227332B2 JP2002001507A JP2002001507A JP4227332B2 JP 4227332 B2 JP4227332 B2 JP 4227332B2 JP 2002001507 A JP2002001507 A JP 2002001507A JP 2002001507 A JP2002001507 A JP 2002001507A JP 4227332 B2 JP4227332 B2 JP 4227332B2
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- Prior art keywords
- pyridoxine
- skin
- cosmetics
- tri
- fatty acid
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- 150000003227 pyridoxines Chemical class 0.000 title description 6
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- 239000000600 sorbitol Substances 0.000 description 1
- 239000008347 soybean phospholipid Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- WNIFXKPDILJURQ-UHFFFAOYSA-N stearyl glycyrrhizinate Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C)CCC(C(=O)OCCCCCCCCCCCCCCCCCC)(C)CC5C4=CC(=O)C3C21C WNIFXKPDILJURQ-UHFFFAOYSA-N 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- 229960005066 trisodium edetate Drugs 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
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- Pyridine Compounds (AREA)
- Cosmetics (AREA)
Description
【０００１】
【発明が属する技術分野】
本発明は、分枝した炭素数８〜２４の脂肪酸でアシル化された、溶解性、安定性、及び皮膚透過性に優れたピリドキシントリ分枝脂肪酸エステルに関する。
【０００２】
【従来の技術】
従来からビタミンＢ６類としては、ピリドキシン塩酸塩が皮膚改善剤、抗皮膚炎症剤、皮脂抑制剤、ニキビ予防剤として皮膚化粧料及び頭髪化粧料に広く使用されてきた。しかしピリドキシン塩酸塩は酸性、アルカリ性下では加熱に対して安定であるが、中性では加熱に対して不安定であることが知られている。また光あるいは紫外線によって徐々に分解を起こし、酸化に対しても安定性は良好ではない。また更に、ピリドキシン塩酸塩はその水溶性のため、直接皮膚に塗布しても皮膚に浸透することはなく、そのままではその有効性を発揮することはできなかった。このためピリドキシン塩酸塩の持つ皮膚改善作用、抗皮膚炎作用における有効性にもかかはらず、化粧料に配合し難いという欠点があった。
【０００３】
このような欠点を改善する方法として、ピリドキシン脂肪酸エステル等のピリドキシン誘導体が提案されている。
【０００４】
しかしながら従来の脂肪酸でアシル化されたピリドキシン脂肪酸エステル、例えばジステアリン酸ピリドキシン、トリステアリン酸ピリドキシン等は融点が高く、通常の常温においては粉末状態で油への溶解性も不十分であり、化粧品への適用は困難である場合が多かった。Ｊ．Ａｍ．Ｏｉｌ Ｃｈｅｍ．Ｓｏｃ．３３１９５６、１１６には、ピリドキシン誘導体のオリーブ油への溶解性が報告されているが、特に安定化のためにトリエステルとしたピリドキシントリ脂肪酸エステルは、溶解性が低いことが示されている。
【０００５】
これらを改善するために不飽和脂肪酸でアシル化されたピリドキシントリ不飽和脂肪酸エステルが試みられている。これらは液状であり、化粧品等への溶解性は良好なものとなるが、酸化に対しては不安定で実用性には問題があった。
【０００６】
【発明が解決しようとする課題】
このような従来のピリドキシン脂肪酸エステルの欠点を改善し、皮膚化粧料、頭髪化粧料等への溶解性を改善し、かつ安定性を高めたピリドキシン脂肪酸エステル誘導体を提供することを目的とした。
【０００７】
【課題を解決するための手段】
本発明者等は、これらの問題を解決すべく鋭意研究した結果、分枝脂肪酸でアシル化されたピリドキシントリ脂肪酸エステルが、油に対する溶解性に優れ、かつ経時安定性も良好であることを見出した。
【０００８】
すなわち、ピリドキシントリ分枝脂肪酸エステルは、油に対する溶解性が良好で、かつ経時的にも安定であること、更にこのピリドキシン脂肪酸エステルを配合た化粧料は、優れた皮膚改善作用、抗皮膚炎症作用、皮脂抑制作用、ニキビ予防剤作用、頭皮改善作用を有することを見出し、本発明を完成した。
【０００９】
【発明の実施の形態】
以下に実施例を挙げて本発明を具体的に説明するが、本発明の技術的範囲がこれらに限定されるものではない。本発明の化合物は、一般式（１）で表されるピリドキシントリ分枝脂肪酸エステルである。式中Ｒは分枝した炭素数８〜２４の脂肪酸残基である。具体的には、２−エチルヘキサン酸、３，５，５−トリメチルヘキサン酸、２−ブチルオクタン酸、２−ヘキシルデカン酸、イソステアリン酸等の分枝脂肪酸残基が挙げられる。
【００１０】
これらの化合物は、例えばピリドキシン塩酸塩のＮ，Ｎ−ジメチルホルムアミド、ピリジン溶液中に脂肪酸クロリドを加えて反応させることによって容易に得ることができるが、これらの方法に限定されるものではない。
【００１１】
本発明のピリドキシントリ分枝脂肪酸エステルは、一般的に化粧料であれば特に使用が限定されることは無く、皮膚化粧料、頭髪化粧料、メーキャップ化粧料等の各種の化粧料に添加することができる。また本発明のピリドキシントリ分枝脂肪酸エステルは、特に添加量を制限されることは無いが、実質的には０．０１重量％〜５重量％が好適な使用範囲である。これ以下の濃度では皮膚改善作用・抗皮膚炎作用等の効果が期待できず、またこれ以上の濃度では効果の向上が期待できない。
【００１２】
本発明の化粧料には、本発明の効果を損なわない範囲で化粧品、医薬部外品等の化粧料に配合される成分として動植物油由来の硬化油、天然由来のロウ、炭化水素系の油相成分、動植物由来の油相成分、シリコーン系の油相成分、フッ素系の油相成分、高級アルコール、増粘剤、紫外線吸収剤、粉体、顔料、色材、陰イオン性界面活性剤、陽イオン性界面活性剤、非イオン性界面活性剤、多価アルコール、糖、高分子化合物、生理活性成分、経皮吸収促進剤、溶媒、酸化防止剤、香料、防腐剤等を配合することができる。
【００１３】
【実施例】
更に本発明を詳細に説明するが、本発明の技術的範囲が実施例に限定されるものではない。
【００１４】
実施例１：トリ２−ブチルオクタン酸ピリドキシンの合成
ピリドキシン塩酸塩５ｇをＤＭＦ５０ｇ、ピリジン９．６ｇに溶解し、室温で２−ブチルオクタノイルクロリド１６．５ｇを滴下した。数時間反応した後、ヘキサン５０ｇ、水５０ｇを添加し抽出した。次いで希塩酸水溶液、飽和炭酸水素ナトリウム水溶液、飽和食塩水で中性になるまで洗った。無水硫酸ナトリウムで脱水後、減圧下に溶媒を留去した。カラムクロマトグラフィーで精製して、無色透明液体１７ｇを得た。
【００１５】
実施例２：トリ２−ヘキシルデカン酸ピリドキシンの合成
ピリドキシン塩酸塩５ｇをＤＭＦ５０ｇ、ピリジン５．７ｇに溶解し、室温で２−ヘキシルデカノイルクロリド２０ｇを滴下した。数時間反応した後、ヘキサン５０ｇ、水５０ｇを添加し抽出した。次いで希塩酸水溶液、飽和炭酸水素ナトリウム水溶液、飽和食塩水で中性になるまで洗った。無水硫酸ナトリウムで脱水後、減圧下に溶媒を留去した。カラムクロマトグラフィーで精製して、無色透明液体１９ｇを得た。
【００１６】
比較例１：トリステアリン酸ピリドキシンの合成
実施例１の合成法に準じて合成物を得た。
【００１７】
（溶解性の評価）
実施例１のトリ２−ブチルオクタン酸ピリドキシン（ＰＩＮ−ＴＢＯ）、実施例２のトリ２−ヘキシルデカン酸ピリドキシン（ＰＩＮ−ＴＨＤ）、及び比較例１のトリステアリン酸ピリドキシン（ＰＩＮ−ＴＳ）の表１に示す溶剤に対する５重量％・室温での溶解性の評価を行った。
（溶解性の評価基準）
○：溶解
△：一部溶解
×：不溶
【００１８】
【表１】
【００１９】
次にトリ２−ヘキシルデカン酸ピリドキシン（ＰＩＮ−ＴＨＤ）を用いた化粧品として皮膚外用剤の実施例について述べる。比較例としてジステアリン酸ピリドキシン（ＰＩＮ−ＤＳ）を用いた。
【００２０】
実施例３〜６、比較例２〜５：評価用皮膚外用剤処方
（処方） 重量％
油相
モノステアリン酸グリセリル（自己乳化型） ５．０
ポリオキシエチレン（２５）セチルエーテル １．５
セタノール ５．０
スクワラン ８．０
トリ（カプリル・カプロン酸）グリセリル ８．０
表２に記載のピリドキシン誘導体 ３．０
水相
１，３−ブチレングリコール ５．０
キサンタンガム ０．２
クエン酸 表２に記載の量
リン酸水素二ナトリウム 表２に記載の量
プロピルパラベン ０．１
メチルパラベン ０．２
精製水 残部
（調製法）
実施例３〜６、比較例２〜５の評価用皮膚外用剤処方処方を、上述の安定性の評価に従って測定した結果を表２に、皮膚改善作用の評価に従って測定した結果を表３に示す。
【００２１】
（安定性の評価）
ｐＨの違いによるピリドキシン誘導体の安定性を調べるために実施例３〜６、比較例２〜５の皮膚外用剤を密閉容器に入れ、４５℃恒温槽中に2ヶ月間放置した。放置後２重量％エタノール溶液を調製し、高速液体クロマトグラフ法によりトリ２−ヘキシルデカン酸ピリドキシンを標準に用いて定量を行った。
【００２２】
（皮膚改善作用の評価）
３５〜５５才の女性をモニターとして（１０名）、実施例３〜６、比較例２〜５の皮膚外用剤を一週間連続使用した後の皮膚改善の効果について、下記基準に基づく自己評価に基づいて評価した。
（皮膚改善作用の評価基準）
◎：明らかに皮膚の状態が改善された。
○：皮膚の状態が改善された。
△：若干、皮膚の状態が改善された。
×：全く皮膚の状態が改善されることはない。
【００２３】
【表２】
【００２４】
【表３】
【００２５】
更にトリ２−ブチルオクタン酸ピリドキシン、及びトリ２−ヘキシルデカン酸ピリドキシンを実際の化粧品処方に利用した例を示す。
【００２６】
実施例７：スキンローション１
（処方） 重量％
Ａ相
トリ２−ブチルオクタン酸ピリドキシン ０．２
水酸化大豆リン脂質 ２．０
Ｂ相
１，３−ブチレングリコール １０．０
メチルパラベン 適量
精製水 残部
Ｃ相
アクリル酸・メタクリル酸アルキル共重合体水溶液 ５．０
トリエタノールアミン ０．１
クエン酸 ０．０５
クエン酸ナトリウム ０．２
精製水 １５．０
（調製方法）
室温で均一に混合したＡ相に、７０℃で加温溶解した後室温まで冷却したＢ相を攪拌しながら添加して可溶化物を調製する。続いて、Ｃ相を室温で均一混合してゲルを調製し、このゲルに攪拌しながら可溶化物を少しずつ添加して調製した。
【００２７】
実施例８：スキンローション２
（処方） 重量％
油相
トリ２−ヘキシルデカン酸ピリドキシン ０．１５
ポリオキシエチレン２０ポリオキシプロピレン４セチルエーテル ０．６
マカデミアナッツ油 ０．１
水相
ヒアルロン酸ナトリウム１％水溶液 ５．０
１，３−ブチレングリコール ５．０
ジプロピレングリコール ５．０
メチルパラベン 適量
精製水 残部
（調製方法）
油相及び水相を７０℃に加温して均一に溶解した後、油相に水相を攪拌しながら添加する。攪拌を続けながら３５℃まで冷却して調製した。
【００２８】
実施例９：アクネ用ローション
（処方） 重量％
油相
消炎剤 適量
エデト酸三ナトリウム ０．０５
精製水 残部
（調製方法）
実施例８と同様の方法で調製した。
【００２９】
実施例１０：保湿ゲル
ソルビトール発酵多糖液 １．５
キサンタンガム２％水溶液 ５．０
１，３−ブチレングリコール ５．０
ジプロピレングリコール ２．０
メチルパラベン 適量
精製水 残部
（調製方法）
実施例８と同様の方法で調製した。
【００３０】
実施例１１：美容オイル
（処方） 重量％
トリ２−ヘキシルデカン酸ピリドキシン ０．２
ミリスチン酸イソセチル １０．０
マカデミアナッツ油 ５．０
ホホバ油 ５．０
天然ビタミンＥ ０．１
オリーブスクワラン 残部
（調製方法）
全ての成分を室温で均一になるまで混合し、調製する。
【００３１】
実施例１２：エモリエントクリーム
（処方） 重量％
油相
トリ２−ヘキシルデカン酸ピリドキシン ０．２
オリーブスクワラン １０．０
ミリスチン酸イソセチル ６．０
トリ２−エチルヘキサン酸グリセリル ３．０
ホホバ油 １．０
メチルポリシロキサン ０．２
セタノール ５．０
ポリオキシエチレン２０セチルエーテル １．０
テトラオレイン酸ポリオキシエチレン４０ソルビット ０．５
モノステアリン酸グリセリル １．０
天然ビタミンＥ ０．１
プロピルパラベン 適量
水相
ソルビトール発酵多糖液 １．５
キサンタンガム ０．１
１，３−ブチレングリコール ５．０
クエン酸 ０．１
クエン酸ナトリウム ０．４
メチルパラベン 適量
精製水 残部
（調製方法）
実施例８と同様の方法で調製した。
【００３２】
実施例１３：敏感肌用クリーム
（処方） 重量％
油相
トリ２−ブチルオクタン酸ピリドキシン ０．１
オリーブスクワラン ８．０
トリ２−エチルヘキサン酸グリセリル ６．０
パルミチン酸セチル ５．０
ミツロウ １．５
ベヘニルアルコール １．０
バチルアルコール １．３
大豆レシチン １．３
グリチルレチン酸ステアリル ０．２
４−ｔｅｒｔ−ブチル−４‘−メトキシベンゾイルメタン ０．３
デカメチルペンタシロキサン ４．０
メチルポリシロキサン ０．３
プロピルパラベン 適量
水相
キサンタンガム２％水溶液 １０．０
グリセリン ３．０
フェノキシエタノール ０．２
ハマメリスエキス ０．２
メチルパラベン 適量
精製水 残部
（調製方法）
実施例８と同様の方法で調製した。
【００３３】
実施例１４：ヘアトニック
（処方） 重量％
Ａ相
トリ２−ヘキシルデカン酸ピリドキシン ０．２
高重合シリコーン ０．３
環状シリコーン ０．３
ビタミンＥ配合リポソーム ４．０
ポリオキシエチレントリデシルエーテル酢酸ナトリウム ０．１
グリセリン ０．３
精製水 １０．０
Ｂ相
ポリオキシエチレン５０硬化ヒマシ油 ０．５
メントール ０．１
防腐剤 適量
エタノール １０．０
精製水 残部
（調製方法）
室温で均一に混合して乳濁させたＡ相に、３５℃で加温溶解した後室温まで冷却したＢ相を攪拌しながら添加して調製した。
【００３４】
（皮膚改善作用の評価）
皮膚改善作用の評価は実施例３〜６、比較例２〜５の皮膚改善作用と同様にして行った。その結果を表４に示す。
【００３５】
（頭皮改善作用の評価）
実施例１４における頭皮改善作用の評価は、３５〜５５才の女性１０名、４０〜５５才の男性５名をモニターとして、一週間連続使用した後の頭皮改善の効果について評価したところ、全てのモニターについて頭皮の油性感の改善が見られた。
【００３６】
【表４】
【発明の効果】
本発明のピリドキシントリ分枝脂肪酸エステルは、優れた皮膚改善作用及び頭皮改善作用を有し、かつ油の溶解性、及び経時的安定性に優れる。[0001]
[Technical field to which the invention belongs]
The present invention relates to a pyridoxine tri-branched fatty acid ester acylated with a branched fatty acid having 8 to 24 carbon atoms and having excellent solubility, stability, and skin permeability.
[0002]
[Prior art]
The vitamin B 6 such conventionally, pyridoxine hydrochloride skin improvement agents, anti-skin-inflammatory agents, sebum inhibitors, have been used extensively in skin cosmetic and a hair cosmetic as acne prophylactic agent. However, pyridoxine hydrochloride is known to be stable to heating under acidic and alkaline conditions, but unstable to heating when neutral. Moreover, it gradually decomposes by light or ultraviolet rays, and its stability against oxidation is not good. Furthermore, since pyridoxine hydrochloride is water-soluble, it does not penetrate into the skin even when applied directly to the skin, and its effectiveness cannot be exhibited as it is. For this reason, there is a drawback that pyridoxine hydrochloride is difficult to be incorporated into cosmetics regardless of its effectiveness in improving skin and anti-dermatitis.
[0003]
As a method for improving such a defect, pyridoxine derivatives such as pyridoxine fatty acid esters have been proposed.
[0004]
However, conventional pyridoxine fatty acid esters acylated with fatty acids, such as pyridoxine distearate and pyridoxine tristearate, have a high melting point, and are not sufficiently soluble in oil in a powder state at normal room temperature, and are therefore not suitable for cosmetics. Application was often difficult. J. et al. Am. Oil Chem. Soc. 331956 and 116 report the solubility of pyridoxine derivatives in olive oil, but it is shown that pyridoxine trifatty acid ester, which is a triester for stabilization, has low solubility.
[0005]
In order to improve these, pyridoxine triunsaturated fatty acid esters acylated with unsaturated fatty acids have been tried. These are liquid and have good solubility in cosmetics and the like, but they are unstable to oxidation and have problems in practical use.
[0006]
[Problems to be solved by the invention]
An object of the present invention is to provide a pyridoxine fatty acid ester derivative that improves the drawbacks of such conventional pyridoxine fatty acid esters, improves solubility in skin cosmetics, hair cosmetics, and the like, and has improved stability.
[0007]
[Means for Solving the Problems]
As a result of diligent research to solve these problems, the present inventors have found that pyridoxine trifatty acid ester acylated with a branched fatty acid has excellent solubility in oil and good stability over time. It was.
[0008]
That is, pyridoxine tri-branched fatty acid ester has good solubility in oil and is stable over time, and cosmetics containing this pyridoxine fatty acid ester have excellent skin-improving action and anti-skin inflammation action. They have found that they have sebum-suppressing action, acne-preventing action, and scalp improving action, and have completed the present invention.
[0009]
DETAILED DESCRIPTION OF THE INVENTION
EXAMPLES The present invention will be specifically described below with reference to examples, but the technical scope of the present invention is not limited to these examples. The compound of the present invention is a pyridoxine tri-branched fatty acid ester represented by the general formula (1). In the formula, R is a branched fatty acid residue having 8 to 24 carbon atoms. Specific examples include branched fatty acid residues such as 2-ethylhexanoic acid, 3,5,5-trimethylhexanoic acid, 2-butyloctanoic acid, 2-hexyldecanoic acid and isostearic acid.
[0010]
These compounds can be easily obtained by adding and reacting, for example, N, N-dimethylformamide of pyridoxine hydrochloride or pyridine solution with fatty acid chloride, but are not limited to these methods.
[0011]
The use of the pyridoxine tri-branched fatty acid ester of the present invention is not particularly limited as long as it is generally a cosmetic, and it may be added to various cosmetics such as skin cosmetics, hair cosmetics, makeup cosmetics, etc. Can do. Further, the amount of the pyridoxine tri-branched fatty acid ester of the present invention is not particularly limited, but substantially 0.01% by weight to 5% by weight is a preferable use range. At concentrations below this level, effects such as skin improvement and anti-dermatitis effects cannot be expected, and at concentrations above this level, improvement in effects cannot be expected.
[0012]
The cosmetics of the present invention include hardened oils derived from animal and vegetable oils, natural waxes, and hydrocarbon oils as ingredients to be blended in cosmetics such as cosmetics and quasi-drugs as long as the effects of the present invention are not impaired. Phase components, animal and plant-derived oil phase components, silicone-based oil phase components, fluorine-based oil phase components, higher alcohols, thickeners, UV absorbers, powders, pigments, coloring materials, anionic surfactants, Cationic surfactants, nonionic surfactants, polyhydric alcohols, sugars, polymer compounds, physiologically active ingredients, transdermal absorption accelerators, solvents, antioxidants, fragrances, preservatives, etc. it can.
[0013]
【Example】
Further, the present invention will be described in detail, but the technical scope of the present invention is not limited to the examples.
[0014]
Example 1: Synthesis of pyridoxine tri-2-butyloctanoate 5 g of pyridoxine hydrochloride was dissolved in 50 g of DMF and 9.6 g of pyridine, and 16.5 g of 2-butyloctanoyl chloride was added dropwise at room temperature. After reacting for several hours, 50 g of hexane and 50 g of water were added and extracted. Subsequently, it was washed with a dilute hydrochloric acid aqueous solution, a saturated aqueous sodium hydrogen carbonate solution, and a saturated saline solution until neutrality. After dehydration with anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. Purification by column chromatography gave 17 g of a colorless transparent liquid.
[0015]
Example 2: Synthesis of pyridoxine tri-2-hexyldecanoate 5 g of pyridoxine hydrochloride was dissolved in 50 g of DMF and 5.7 g of pyridine, and 20 g of 2-hexyldecanoyl chloride was added dropwise at room temperature. After reacting for several hours, 50 g of hexane and 50 g of water were added and extracted. Subsequently, it was washed with a dilute hydrochloric acid aqueous solution, a saturated aqueous sodium hydrogen carbonate solution, and a saturated saline solution until neutrality. After dehydration with anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. Purification by column chromatography gave 19 g of a colorless transparent liquid.
[0016]
Comparative Example 1: Synthesis of pyridoxine tristearate A synthetic product was obtained according to the synthesis method of Example 1.
[0017]
(Evaluation of solubility)
Table of trido-2-butyloctanoic acid pyridoxine (PIN-TBO) of Example 1, pyridoxine tri-2-hexyldecanoate (PIN-THD) of Example 2, and pyridoxine tristearate (PIN- TS ) of Comparative Example 1 The solubility at 5% by weight and room temperature in the solvent shown in Fig. 1 was evaluated.
(Solubility evaluation criteria)
○: dissolved Δ: partially dissolved ×: insoluble
[Table 1]
[0019]
Next, examples of external preparations for skin as cosmetics using pyridoxine tri-2-hexyldecanoate (PIN-THD) will be described. As a comparative example, pyridoxine distearate (PIN-DS) was used.
[0020]
Examples 3 to 6, Comparative Examples 2 to 5: Formulation for skin external preparation for evaluation (prescription)% by weight
Oil phase glyceryl monostearate (self-emulsifying) 5.0
Polyoxyethylene (25) cetyl ether 1.5
Cetanol 5.0
Squalane 8.0
Tri (capryl / caproic acid) glyceryl 8.0
Pyridoxine derivatives listed in Table 2 3.0
Aqueous phase 1,3-butylene glycol 5.0
Xanthan gum 0.2
Citric acid Amount described in Table 2 Disodium hydrogen phosphate Amount described in Table 2 Propylparaben 0.1
Methylparaben 0.2
Purified water balance (preparation method)
Table 2 shows the results of measuring the external preparation formulations for evaluation of Examples 3 to 6 and Comparative Examples 2 to 5 according to the above-described stability evaluation, and Table 3 shows the results of measuring according to the evaluation of the skin improvement effect. .
[0021]
(Evaluation of stability)
In order to examine the stability of the pyridoxine derivative due to the difference in pH, the skin external preparations of Examples 3 to 6 and Comparative Examples 2 to 5 were placed in a sealed container and left in a 45 ° C. constant temperature bath for 2 months. After standing, a 2 wt% ethanol solution was prepared, and quantified by high performance liquid chromatography using pyridoxine tri-2-hexyldecanoate as a standard.
[0022]
(Evaluation of skin improvement effect)
35-55-year-old women as monitors (10 persons), self-assessment based on the following criteria for the effects of skin improvement after continuous use of the skin external preparations of Examples 3-6 and Comparative Examples 2-5 for one week Based on the evaluation.
(Evaluation criteria for skin improvement effect)
A: The skin condition was clearly improved.
○: Skin condition was improved.
Δ: The skin condition was slightly improved.
X: Skin condition is not improved at all.
[0023]
[Table 2]
[0024]
[Table 3]
[0025]
Furthermore, an example is shown in which pyridoxine tri-2-butyloctanoate and pyridoxine tri-2-hexyldecanoate are used in an actual cosmetic formulation.
[0026]
Example 7: Skin lotion 1
(Prescription) Weight%
Phase A tri-2-butyloctanoate pyridoxine 0.2
Hydroxylated soybean phospholipid 2.0
Phase B 1,3-butylene glycol 10.0
Methyl paraben Appropriate amount of purified water The remaining C phase aqueous solution of acrylic acid / alkyl methacrylate copolymer 5.0
Triethanolamine 0.1
Citric acid 0.05
Sodium citrate 0.2
Purified water 15.0
(Preparation method)
A solubilized product is prepared by adding, with stirring, phase B, which has been heated and dissolved at 70 ° C. and then cooled to room temperature, to phase A uniformly mixed at room temperature. Subsequently, a gel was prepared by uniformly mixing Phase C at room temperature, and a solubilizate was added little by little while stirring the gel.
[0027]
Example 8: Skin lotion 2
(Prescription) Weight%
Oil phase Tri-2-hexyldecanoate pyridoxine 0.15
Polyoxyethylene 20 polyoxypropylene 4 cetyl ether 0.6
Macadamia nut oil 0.1
Aqueous phase Sodium hyaluronate 1% aqueous solution 5.0
1,3-butylene glycol 5.0
Dipropylene glycol 5.0
Methyl paraben Appropriate amount of purified water The remainder (preparation method)
The oily phase and the aqueous phase are heated to 70 ° C. and dissolved uniformly, and then the aqueous phase is added to the oily phase with stirring. It was prepared by cooling to 35 ° C. with continued stirring.
[0028]
Example 9: Acne Lotion (Prescription) Weight%
Oil phase
Purified water balance (preparation method)
Prepared in the same manner as in Example 8.
[0029]
Example 10: Moisturizing gel
Xanthan gum 2% aqueous solution 5.0
1,3-butylene glycol 5.0
Dipropylene glycol 2.0
Methyl paraben Appropriate amount of purified water The remainder (preparation method)
Prepared in the same manner as in Example 8.
[0030]
Example 11: Beauty oil (prescription)% by weight
Pyridoxine tri-2-hexyldecanoate 0.2
Isocetyl myristate 10.0
Macadamia nut oil 5.0
Jojoba oil 5.0
Natural vitamin E 0.1
The remaining olive squalane (preparation method)
Mix and prepare all ingredients until uniform at room temperature.
[0031]
Example 12: Emollient cream (formulation)% by weight
Oil phase tri-2-hexyldecanoate pyridoxine 0.2
Olive Squalane 10.0
Isocetyl myristate 6.0
Glyceryl tri-2-ethylhexanoate 3.0
Jojoba oil 1.0
Methylpolysiloxane 0.2
Cetanol 5.0
Polyoxyethylene 20 cetyl ether 1.0
Tetraoleic acid polyoxyethylene 40 sorbit 0.5
Glyceryl monostearate 1.0
Natural vitamin E 0.1
Propylparaben appropriate amount aqueous phase sorbitol fermentation polysaccharide solution 1.5
Xanthan gum 0.1
1,3-butylene glycol 5.0
Citric acid 0.1
Sodium citrate 0.4
Methyl paraben Appropriate amount of purified water The remainder (preparation method)
Prepared in the same manner as in Example 8.
[0032]
Example 13: Sensitive Skin Cream (Prescription) Weight%
Oil phase tri-2-butyloctanoic acid pyridoxine 0.1
Olive Squalane 8.0
Glyceryl tri-2-ethylhexanoate 6.0
Cetyl palmitate 5.0
Beeswax 1.5
Behenyl alcohol 1.0
Batyl alcohol 1.3
Soy lecithin 1.3
Stearyl glycyrrhetinate 0.2
4-tert-butyl-4'-methoxybenzoylmethane 0.3
Decamethylpentasiloxane 4.0
Methyl polysiloxane 0.3
Propylparaben appropriate amount aqueous phase xanthan gum 2% aqueous solution 10.0
Glycerin 3.0
Phenoxyethanol 0.2
Hamamelis extract 0.2
Methyl paraben Appropriate amount of purified water The remainder (preparation method)
Prepared in the same manner as in Example 8.
[0033]
Example 14: Hair tonic (prescription)% by weight
Phase A tripyridoxine tri-2-hexyldecanoate 0.2
Highly polymerized silicone 0.3
Cyclic silicone 0.3
Liposomes with vitamin E 4.0
Sodium polyoxyethylene tridecyl ether acetate 0.1
Glycerin 0.3
Purified water 10.0
Phase B polyoxyethylene 50 hydrogenated castor oil 0.5
Menthol 0.1
Preservative appropriate amount ethanol 10.0
Purified water balance (preparation method)
It was prepared by adding, with stirring, Phase B, which was dissolved by heating at 35 ° C. to Phase A, which was uniformly mixed and emulsified at room temperature, and then cooled to room temperature.
[0034]
(Evaluation of skin improvement effect)
The skin improvement effect was evaluated in the same manner as the skin improvement effects of Examples 3 to 6 and Comparative Examples 2 to 5. The results are shown in Table 4.
[0035]
(Evaluation of scalp improvement)
The evaluation of the scalp improving effect in Example 14 was carried out using 10 females of 35 to 55 years old and 5 males of 40 to 55 years old as monitors, and the effects of scalp improvement after continuous use for one week were evaluated. The monitor showed an improvement in the oily feel of the scalp.
[0036]
[Table 4]
【The invention's effect】
The pyridoxine tri-branched fatty acid ester of the present invention has excellent skin-improving action and scalp-improving action, and is excellent in oil solubility and stability over time.
Claims (4)
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| CN111333571A (en) * | 2020-03-07 | 2020-06-26 | 南雄阳普医疗科技有限公司 | Method for synthesizing vitamin B6 triisopalmitate |
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