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JPH0632710A - Skin external preparation - Google Patents

Skin external preparation

Info

Publication number
JPH0632710A
JPH0632710A JP4227728A JP22772892A JPH0632710A JP H0632710 A JPH0632710 A JP H0632710A JP 4227728 A JP4227728 A JP 4227728A JP 22772892 A JP22772892 A JP 22772892A JP H0632710 A JPH0632710 A JP H0632710A
Authority
JP
Japan
Prior art keywords
retinol
external preparation
skin
skin external
present
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
JP4227728A
Other languages
Japanese (ja)
Other versions
JP3545429B2 (en
Inventor
Takeshi Yanagida
威 柳田
Okihiko Sakamoto
興彦 阪本
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.)
Shiseido Co Ltd
Original Assignee
Shiseido Co 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
Priority to JP22772892A priority Critical patent/JP3545429B2/en
Application filed by Shiseido Co Ltd filed Critical Shiseido Co Ltd
Priority to US08/204,286 priority patent/US5484816A/en
Priority to DE1993634151 priority patent/DE69334151T2/en
Priority to DE69333526T priority patent/DE69333526T2/en
Priority to KR1019940700795A priority patent/KR100295030B1/en
Priority to EP93914997A priority patent/EP0608433B1/en
Priority to AT04000012T priority patent/ATE365530T1/en
Priority to EP04000012A priority patent/EP1433477B1/en
Priority to ES93914997T priority patent/ES2221921T3/en
Priority to TW82105572A priority patent/TW302284B/zh
Priority to AT93914997T priority patent/ATE266999T1/en
Priority to ES04000012T priority patent/ES2289370T3/en
Priority to PCT/JP1993/000969 priority patent/WO1994001074A1/en
Priority to EP06075806A priority patent/EP1714640A1/en
Priority to TW85115876A priority patent/TW317502B/zh
Publication of JPH0632710A publication Critical patent/JPH0632710A/en
Priority to US08/429,905 priority patent/US6024941A/en
Application granted granted Critical
Publication of JP3545429B2 publication Critical patent/JP3545429B2/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

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  • Medicinal Preparation (AREA)
  • Cosmetics (AREA)

Abstract

PURPOSE:To obtain a skin external preparation remarkably improved in stability of retinol. CONSTITUTION:This skin external preparation is obtained by blending retinol together with one or two or more of polyethylene glycol and/or polypropylene glycol.

Description

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

【0001】[0001]

【産業上の利用分野】本発明はレチノールの安定性を著
しく向上させた皮膚外用剤に関するものである。
BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an external preparation for skin in which retinol stability is remarkably improved.

【0002】[0002]

【従来の技術】レチノールは皮膚角化症等の予防、治療
や、皮膚老化の防止、回復に有効な成分であることが知
られている。
2. Description of the Related Art Retinol is known to be an effective component for the prevention and treatment of cutaneous keratoses and the like, and the prevention and recovery of skin aging.

【0003】しかしながらレチノールは構造的に極めて
不安定であり、光、空気、熱、金属イオン等により容易
に種々の異性化、分解、重合等を起こすため、安定に皮
膚外用剤に配合することが困難であった。安定化を目的
として脂肪酸エステル化などの手法が試みられている
が、エステル化は安定化には効果があるものの皮膚への
作用という面ではレチノール自身よりはるかに劣ってし
まう。
However, retinol is structurally extremely unstable and easily undergoes various isomerizations, decompositions, polymerizations and the like due to light, air, heat, metal ions, etc., so that it can be stably compounded in an external preparation for skin. It was difficult. Although methods such as fatty acid esterification have been attempted for the purpose of stabilization, esterification is effective for stabilization but is far inferior to retinol itself in terms of action on the skin.

【0004】[0004]

【発明が解決しようとする課題】本発明者らは係る事情
に鑑み鋭意研究の結果、レチノールとともにポリエチレ
ングリコール(以下PEGと省略する。)、ポリプロピ
レングリコール(以下PPGと省略する。)の一種また
は二種以上を配合すればレチノールの安定性が著しく向
上することを見出し、本発明を完成するに至った。
DISCLOSURE OF THE INVENTION As a result of intensive studies conducted by the present inventors in view of such circumstances, one or two of polyethylene glycol (hereinafter abbreviated as PEG) and polypropylene glycol (hereinafter abbreviated as PPG) together with retinol was found. It has been found that the stability of retinol is remarkably improved by mixing at least one species, and the present invention has been completed.

【0005】[0005]

【課題を解決するための手段】すなわち本発明の要旨
は、レチノールと、PEG、PPGの一種または二種以
上を配合することを特徴とする皮膚外用剤に存在する。
Means for Solving the Problems That is, the gist of the present invention resides in an external preparation for skin characterized by containing retinol and one or more of PEG and PPG.

【0006】以下、本発明の構成について詳述する。The structure of the present invention will be described in detail below.

【0007】本発明に用いられるレチノールは別名ビタ
ミンAと呼ばれ、末端が水酸基であるレチノール自身を
示し、その脂肪酸エステルは含まない。all−トラン
ス型または13−シス型であることが望ましく、それら
の混合物であっても構わない。
The retinol used in the present invention is also called vitamin A, which means retinol itself having a hydroxyl group at the terminal and does not contain its fatty acid ester. All-trans type or 13-cis type is desirable, and a mixture thereof may be used.

【0008】本発明に従って皮膚外用剤に配合される量
としては特に制限はないが、レチノールとしての肌への
効果を考えると0.0001重量%以上であり、レチノ
ールの効果を強く訴求するためには好ましくは0.00
1重量%以上である。配合上限は皮膚外用剤としての性
質上好ましくは1重量%である。
There is no particular limitation on the amount to be added to the external preparation for skin according to the present invention, but considering the effect on the skin as retinol, it is 0.0001% by weight or more, and in order to strongly appeal the effect of retinol. Is preferably 0.00
It is 1% by weight or more. The upper limit of the compounding ratio is preferably 1% by weight in view of the property as an external preparation for skin.

【0009】また本発明に配合されるPEG、PPGと
してはPEG200、PEG300、PEG400、P
EG1500、PEG4000、PEG6000、PE
G20000などや、PPG400、PPG750、P
PG1200、PPG2000、PPG3000などが
有名である。
The PEG and PPG blended in the present invention include PEG200, PEG300, PEG400, P
EG1500, PEG4000, PEG6000, PE
G20000, PPG400, PPG750, P
PG1200, PPG2000, PPG3000, etc. are famous.

【0010】これらを一種または二種以上配合するが、
本発明の効果を発揮する目的で配合される量としては
0.1重量%以上が必要であり、過剰に配合しても本発
明の効果を阻害するものではない。しかしながら著しく
過剰に配合した場合、皮膚外用剤としての品質を損ねる
ことがあるので注意が必要である。
These are blended in one kind or two or more kinds,
The amount added for the purpose of exerting the effect of the present invention is required to be 0.1% by weight or more, and an excessive amount of addition does not inhibit the effect of the present invention. However, it is necessary to exercise caution because if it is excessively blended, the quality of the external preparation for the skin may be impaired.

【0011】本発明においてレチノールとPEGおよび
/またはPPGを配合される皮膚外用剤基剤としては通
常の皮膚外用剤基剤ならばいずれのものも利用できる。
すなわち、液状、ゲル状、ペースト状、クリーム状、あ
るいは粉末状、固状などのもので、皮膚外用剤を修飾す
る成分として保湿剤、油分、界面活性剤、増粘剤、金属
封鎖剤、その他の紫外線吸収剤、薬剤、色素、香料など
が併用できることは言うまでもない。
In the present invention, as a skin external preparation base containing retinol and PEG and / or PPG, any conventional skin external preparation base can be used.
That is, liquid, gel, paste, cream, powder, solid or the like, as a component for modifying the skin external preparation, a moisturizer, an oil, a surfactant, a thickener, a sequestering agent, etc. It goes without saying that the ultraviolet absorbers, drugs, dyes, fragrances, etc. can be used in combination.

【0012】[0012]

【実施例】次に本発明をより多くの実施例で詳述するが
本発明はこれにより限定されるものではない。
EXAMPLES The present invention will now be described in more detail with reference to more examples, but the present invention is not limited thereto.

【0013】[0013]

【表1】 [Table 1]

【0014】実施例1、2および3では比較例に比べレ
チノールの安定性が向上しているが、これは本発明に係
る効果である。
In Examples 1, 2 and 3, the stability of retinol is improved as compared with Comparative Example, which is an effect according to the present invention.

【0015】レチノールの定量方法 エタノールを溶媒として用いた325nmでの吸光度測
定法により定量を実施した。なお計算にあたっては極大
吸収325nm E(1%,1cm)=1835とし
た。
Quantitative Method of Retinol Quantitative analysis was carried out by an absorbance measuring method at 325 nm using ethanol as a solvent. In the calculation, the maximum absorption was 325 nm E (1%, 1 cm) = 1835.

【0016】 実施例4 クリーム (重量%) A.セタノール 3 グリセリルモノステアレート 2 POE(25)セチルエーテル 1 ステアリン酸 3 ワセリン 3 イソプロピルミリステート 5 スクワラン 5 レチノール 0.1 BHT 0.05 香料 適量 B.PEG1500 3 グリセリン 9 水酸化カリウム 0.2 精製水 全体を100とする量 Aの油相部分とBの水相部分をそれぞれ70℃で加熱溶
解し、AをBに加え乳化する。そののち冷却処理をして
クリームを得る。
Example 4 Cream (wt%) A. Cetanol 3 Glyceryl monostearate 2 POE (25) cetyl ether 1 Stearic acid 3 Vaseline 3 Isopropyl myristate 5 Squalane 5 Retinol 0.1 BHT 0.05 Fragrance Suitable amount B. PEG1500 3 glycerin 9 potassium hydroxide 0.2 Purified water based on the total amount of 100 The oil phase portion of A and the water phase portion of B are dissolved by heating at 70 ° C., and A is added to B to emulsify. Then, it is cooled to obtain a cream.

【0017】 実施例5 リップスティック (重量%) 固形パラフィン 8 カルナウバロウ 2 キャンデリラロウ 4 マイクロクリスタリンワックス 6 水添ラノリン 15 イソプロピルパルミテート 全体を100とする量 グリセリルジイソステアレート 30 PPG3000 15 レチノール 1 BHT 0.3 調合色剤(赤色系) 7 香料 適量 上記の各原料を80℃で加熱溶解し、そののち所定の容
器に流し込みリップスティックを得る。
Example 5 Lipstick (wt%) Solid paraffin 8 Carnauba wax 2 Candelilla wax 4 Microcrystalline wax 6 Hydrogenated lanolin 15 Isopropyl palmitate Amount based on 100 Glyceryl diisostearate 30 PPG 3000 15 Retinol 1 BHT 0 .3 Coloring agent (red) 7 Perfume Suitable amount Each of the above raw materials is heated and melted at 80 ° C., and then poured into a predetermined container to obtain a lipstick.

【0018】 実施例6 化粧水 (重量%) レチノール 0.0001 オレイルアルコール 0.001 α−トコフェロール 0.005 POE(20)オクチルドデカノール 0.8 エタノール 8 PEG300 3 PEG1500 1 メチルパラベン 0.15 乳酸 0.03 乳酸ナトリウム 0.07 精製水 全体を100とする量Example 6 Lotion (wt%) retinol 0.0001 oleyl alcohol 0.001 α-tocopherol 0.005 POE (20) octyldodecanol 0.8 ethanol 8 PEG300 3 PEG 1500 1 methylparaben 0.15 lactic acid 0. 03 Sodium lactate 0.07 Purified water 100

【0019】 実施例7 アイリンクルオイル (重量%) オリーブオイル 40 2−エチルヘキサン酸トリグリセリド 26 スクワラン 30 PPG4000 2 PEG20000 0.9 δ−トコフェロール 1 レチノール 0.1Example 7 Eye Wrinkle Oil (% by Weight) Olive Oil 40 2-Ethylhexanoic Acid Triglyceride 26 Squalane 30 PPG4000 2 PEG20000 0.9 δ-Tocopherol 1 Retinol 0.1

【0020】 実施例8 美容ペースト PEG300 30 PEG1500 40 PEG4000 10 レチノール 0.3 イソプロピルミリステート 5 POE(25)セチルエーテル 2 ステアリン酸 5 精製水 全体を100とする量Example 8 Beauty Paste PEG300 30 PEG1500 40 PEG4000 10 Retinol 0.3 Isopropyl myristate 5 POE (25) Cetyl ether 2 Stearic acid 5 Purified water 100 parts in total

【0021】 実施例9 ナイトクリーム スクワラン 15 イソプロピルミリステート 5 二酸化ケイ素 3 ワセリン 6 グリセリルモノイソステアレート 2 POE(7)硬化ヒマシ油 1.5 プロピルパラベン 0.2 レチノール 0.4 PEG6000 3 PEG400 3 グリセリン 17 精製水 全体を100とする量Example 9 Night Cream Squalane 15 Isopropylmyristate 5 Silicon Dioxide 3 Vaseline 6 Glyceryl Monoisostearate 2 POE (7) Hydrogenated Castor Oil 1.5 Propylparaben 0.2 Retinol 0.4 PEG6000 3 PEG400 3 Glycerin 17 Amount of purified water as 100

【0022】実施例4〜9の皮膚外用剤は日常的な使用
においてレチノールの安定性に優れたものであった。
The skin external preparations of Examples 4 to 9 were excellent in retinol stability in daily use.

【0023】[0023]

【発明の効果】本発明の皮膚外用剤においてはポリエチ
レングリコールおよび/またはポリプロピレングリコー
ルを配合することによりレチノールの安定性を著しく向
上させることができる。
INDUSTRIAL APPLICABILITY In the external preparation for skin of the present invention, the stability of retinol can be markedly improved by incorporating polyethylene glycol and / or polypropylene glycol.

Claims (1)

【特許請求の範囲】[Claims] 【請求項1】 レチノールとともにポリエチレングリコ
ールおよび/またはポリプロピレングリコールを配合し
たことを特徴とする皮膚外用剤。
1. An external preparation for skin, comprising polyethylene glycol and / or polypropylene glycol mixed with retinol.
JP22772892A 1992-07-13 1992-07-13 Retinol stable combination skin external preparation Expired - Fee Related JP3545429B2 (en)

Priority Applications (16)

Application Number Priority Date Filing Date Title
JP22772892A JP3545429B2 (en) 1992-07-13 1992-07-13 Retinol stable combination skin external preparation
AT93914997T ATE266999T1 (en) 1992-07-13 1993-07-13 DERMATOLOGICAL COMPOSITION
DE69333526T DE69333526T2 (en) 1992-07-13 1993-07-13 DERMATOLOGICAL COMPOSITION
KR1019940700795A KR100295030B1 (en) 1992-07-13 1993-07-13 Skin external composition
EP93914997A EP0608433B1 (en) 1992-07-13 1993-07-13 Composition for dermatologic preparation
AT04000012T ATE365530T1 (en) 1992-07-13 1993-07-13 STABILIZED SKIN CARE PRODUCT CONTAINING RETINOL FOR EXTERNAL USE
EP04000012A EP1433477B1 (en) 1992-07-13 1993-07-13 Stabilised external skin treatment composition comprising retinol
ES93914997T ES2221921T3 (en) 1992-07-13 1993-07-13 COMPOSITION FOR DERMATOLOGICAL PREPARATION.
US08/204,286 US5484816A (en) 1992-07-13 1993-07-13 External skin treatment composition
DE1993634151 DE69334151T2 (en) 1992-07-13 1993-07-13 Retinol-containing, stabilized skin care product for external use
ES04000012T ES2289370T3 (en) 1992-07-13 1993-07-13 STABILIZED COMPOSITION FOR EXTERNAL SKIN TREATMENT THAT RETINOL INCLUDES.
PCT/JP1993/000969 WO1994001074A1 (en) 1992-07-13 1993-07-13 Composition for dermatologic preparation
EP06075806A EP1714640A1 (en) 1992-07-13 1993-07-13 Stabilised external skin treatment composition comprising retinol.
TW85115876A TW317502B (en) 1992-07-13 1993-07-13
TW82105572A TW302284B (en) 1992-07-13 1993-07-13
US08/429,905 US6024941A (en) 1992-07-13 1995-04-27 External skin treatment composition

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP22772892A JP3545429B2 (en) 1992-07-13 1992-07-13 Retinol stable combination skin external preparation

Publications (2)

Publication Number Publication Date
JPH0632710A true JPH0632710A (en) 1994-02-08
JP3545429B2 JP3545429B2 (en) 2004-07-21

Family

ID=16865431

Family Applications (1)

Application Number Title Priority Date Filing Date
JP22772892A Expired - Fee Related JP3545429B2 (en) 1992-07-13 1992-07-13 Retinol stable combination skin external preparation

Country Status (1)

Country Link
JP (1) JP3545429B2 (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5614149A (en) * 1993-07-08 1997-03-25 Nippon Yakin Kogyo Co., Ltd. Stainless steels for coins and method of producing coins of stainless steel
WO2002056852A1 (en) 2001-01-19 2002-07-25 Shiseido Company, Ltd. Cosmetics
KR100402576B1 (en) * 2000-07-05 2003-10-22 동아제약 주식회사 Cosmetic composition containing retinol by multiple stabilization
US10260807B2 (en) 2013-07-05 2019-04-16 Freund Corporation Drying device and continuous granule production system
WO2020137785A1 (en) 2018-12-28 2020-07-02 株式会社 資生堂 Retinol-containing oil-in-water type emulsified cosmetic material

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5218811A (en) * 1975-08-01 1977-02-12 Eisai Co Ltd Preparation of aqueous solution of fat- soluble substances
JPS5655307A (en) * 1979-10-12 1981-05-15 Kobayashi Kooc:Kk Opacifying cosmetic
JPS61291514A (en) * 1985-06-19 1986-12-22 Kanebo Ltd Solubilized water-based clean cosmetic
JPH01268617A (en) * 1988-02-26 1989-10-26 L'oreal Sa Skin beauty improving cosmetics composed of polyvitamin mixture
JPH03173831A (en) * 1982-07-13 1991-07-29 L'oreal Sa Cosmetic or pharmaceutical composition
JPH03188007A (en) * 1989-12-18 1991-08-16 Kanebo Ltd Transparent cosmetic of solubilization type
JPH0449214A (en) * 1990-06-15 1992-02-18 Kanebo Ltd Transparent cosmetic of solubilization type
JPH0640878A (en) * 1991-03-20 1994-02-15 L'oreal Sa Cosmetics composition opposing aging of skin

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5218811A (en) * 1975-08-01 1977-02-12 Eisai Co Ltd Preparation of aqueous solution of fat- soluble substances
JPS5655307A (en) * 1979-10-12 1981-05-15 Kobayashi Kooc:Kk Opacifying cosmetic
JPH03173831A (en) * 1982-07-13 1991-07-29 L'oreal Sa Cosmetic or pharmaceutical composition
JPS61291514A (en) * 1985-06-19 1986-12-22 Kanebo Ltd Solubilized water-based clean cosmetic
JPH01268617A (en) * 1988-02-26 1989-10-26 L'oreal Sa Skin beauty improving cosmetics composed of polyvitamin mixture
JPH03188007A (en) * 1989-12-18 1991-08-16 Kanebo Ltd Transparent cosmetic of solubilization type
JPH0449214A (en) * 1990-06-15 1992-02-18 Kanebo Ltd Transparent cosmetic of solubilization type
JPH0640878A (en) * 1991-03-20 1994-02-15 L'oreal Sa Cosmetics composition opposing aging of skin

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5614149A (en) * 1993-07-08 1997-03-25 Nippon Yakin Kogyo Co., Ltd. Stainless steels for coins and method of producing coins of stainless steel
KR100402576B1 (en) * 2000-07-05 2003-10-22 동아제약 주식회사 Cosmetic composition containing retinol by multiple stabilization
WO2002056852A1 (en) 2001-01-19 2002-07-25 Shiseido Company, Ltd. Cosmetics
US7169379B2 (en) 2001-01-19 2007-01-30 Shiseido Co., Ltd. Cosmetics
US10260807B2 (en) 2013-07-05 2019-04-16 Freund Corporation Drying device and continuous granule production system
WO2020137785A1 (en) 2018-12-28 2020-07-02 株式会社 資生堂 Retinol-containing oil-in-water type emulsified cosmetic material

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