JPS61215316A - External agent for skin - Google Patents

External agent for skin

Info

Publication number
JPS61215316A
JPS61215316A JP5648985A JP5648985A JPS61215316A JP S61215316 A JPS61215316 A JP S61215316A JP 5648985 A JP5648985 A JP 5648985A JP 5648985 A JP5648985 A JP 5648985A JP S61215316 A JPS61215316 A JP S61215316A
Authority
JP
Japan
Prior art keywords
skin
dimethylethyl
ester
methoxydibenzoylmethane
unsaturated alkyl
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
JP5648985A
Other languages
Japanese (ja)
Other versions
JPH0645531B2 (en
Inventor
Takeshi Yanagida
威 柳田
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
Application filed by Shiseido Co Ltd filed Critical Shiseido Co Ltd
Priority to JP60056489A priority Critical patent/JPH0645531B2/en
Publication of JPS61215316A publication Critical patent/JPS61215316A/en
Publication of JPH0645531B2 publication Critical patent/JPH0645531B2/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • 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
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37Esters of carboxylic acids
    • 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
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35Ketones, e.g. benzophenone
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Emergency Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Cosmetics (AREA)

Abstract

PURPOSE:To provide an external agent for skin, composed of a specific ultraviolet absorber in combination with the ester of an acid and an alcohol each having 9-31C straight or branched unsaturated alkyl residue, having improved compatibility to base, preventing the deterioration caused by the precipitation of crystals and having excellent ultraviolet-shielding effect and high quality. CONSTITUTION:The objective agent can be produced by adding the ester of an acid and an alcohol each having 9-31C straight or branched unsaturated alkyl residue such as 2-hexyldecyl myristate to a dermatic agent for external use containing preferably 0.01-10% 4-(1,1-dimethylethyl)-4'- methoxydibenzoylmethane as an ultraviolet absorber capable of absorbing sunlight, especially ultraviolet ray having relatively long wavelength and harmful to the skin (UV-A). The amount of the ester is >=1/2 of the UV-absorber. The obtained external agent for skin has improved compatibility of the above UV- absorber to the base of the external agent and excellent ultraviolet-absorbing effect and quality and is storable stably for a long period with little deterioration.

Description

【発明の詳細な説明】 [産業上の利用分野] 本発明は4− (1,1−ジメチルエチル)−4°−メ
トキシジベンゾイルメタンとともに、炭素数9ないし3
1の直鎖、分岐、不飽和アルキル残基を持つ酸と炭素数
9ないし31の直鎖、分岐、不飽和アルキル残基を持つ
アルコールのエステルを配合することにより優れた紫外
線防御効果と、すぐれた品質をもつ皮膚外用剤に関する
ものである。
Detailed Description of the Invention [Industrial Field of Application] The present invention relates to 4-(1,1-dimethylethyl)-4°-methoxydibenzoylmethane, which has 9 to 3 carbon atoms;
By blending an acid with a linear, branched, or unsaturated alkyl residue of 1 and an ester of an alcohol with a linear, branched, or unsaturated alkyl residue of 9 to 31 carbon atoms, it has an excellent UV protection effect and excellent UV protection. This topic relates to external skin preparations with superior quality.

[従来の技術] 太陽光線は日焼けをおこすばかりか、その日焼けのため
に皮膚の老化を促進することが知られている。
[Prior Art] It is known that sunlight not only causes sunburn, but also accelerates skin aging due to the sunburn.

太陽光線を防ぐように配慮きれた皮膚外用剤はすくなく
ないが、そのいずれもが粉末を配合して主として反射、
散乱によって対処したもの、あるいはUV−Bとよばれ
る比較的波長の短かい紫外線のみを吸収するサリチル酸
誘導体、アミノ安、じ香酸誘導体のような物質を配合し
たものであった。
There are many external skin preparations that are carefully designed to protect against sunlight, but all of them contain powder that mainly protects against sunlight.
Some methods used scattering methods to deal with the problem, or others included substances such as salicylic acid derivatives, aminoaminobenzene, and dizoic acid derivatives that absorb only ultraviolet rays with relatively short wavelengths called UV-B.

[発明が解決しようとする問題点] 4−(1,1−ジメチルエチル)−4′−メトキシジベ
ンゾイルメタンは太陽光線、特に皮膚に対して有害なU
V−Aとよばれる比較的長波長の紫外線を吸収する物質
として近年脚光をあびているが、皮膚外用剤基剤との相
溶性が悪く、溶解状態で皮膚外用剤に配合しても比較的
短時間のうちに結晶として析出してしまうことが多い。
[Problems to be solved by the invention] 4-(1,1-dimethylethyl)-4'-methoxydibenzoylmethane is harmful to sunlight, especially U, which is harmful to the skin.
In recent years, it has been attracting attention as a substance called VA that absorbs relatively long wavelength ultraviolet rays, but it has poor compatibility with the base of external skin preparations, and even if it is incorporated into external skin preparations in a dissolved state, it has a relatively short lifespan. It often precipitates as crystals over time.

結晶として析出した場合は皮膚外用剤の品質な著しく損
ねることは言うまでもなく、本来の目的の紫外線吸収能
ざえも発揮できない状態となってしまう。
If it precipitates as crystals, it goes without saying that the quality of the external skin preparation will be significantly impaired, and the originally intended ultraviolet absorbing ability will not be achieved.

L問題点を解決するための手段] 本発明者は係る事情に鑑み鋭意研究の結果、4−(1,
1−ジメチルエチル)−4′−メトキシジベンゾイルメ
タンとともに、炭素数9ないし31の直鎖、分岐、不飽
和アルキル残基を持つ酸と炭素数9ないし31の直鎖、
分岐、不飽和アルキル残基を持つアルコールのエステル
を配合すれば、紫外線吸収効果に優れることはもちろん
、長期間安定性に優れ品質劣化をおこすことのすくない
皮膚外用剤を得られることを見出し本発明を完成するに
至った。
Means for Solving the L Problem] In view of the circumstances, the present inventor has conducted intensive research and found that 4-(1,
1-dimethylethyl)-4'-methoxydibenzoylmethane, an acid having a straight chain, branched or unsaturated alkyl residue having 9 to 31 carbon atoms, and a straight chain having 9 to 31 carbon atoms;
It was discovered that by blending an alcohol ester with a branched, unsaturated alkyl residue, it is possible to obtain an external skin preparation that not only has excellent ultraviolet absorption effects but also has long-term stability and is less prone to quality deterioration.The present invention has been made. I was able to complete it.

すなわち本発明は優れた紫外線吸収効果、優れた品質を
もつ皮膚外用剤を提供するものである。
That is, the present invention provides an external preparation for skin that has an excellent ultraviolet absorption effect and excellent quality.

以下、本発明の構成について詳述する。Hereinafter, the configuration of the present invention will be explained in detail.

本発明で用いられる4−(1,1−ジメチルエチル)−
4°−メトキシジベンゾイルメタンは、特開昭55−6
6535に示きれる方法で製造され、シボダン株式会社
より「パルソール1789」の商品名で供給されている
4-(1,1-dimethylethyl)- used in the present invention
4°-Methoxydibenzoylmethane is disclosed in JP-A-55-6
6535, and is supplied by Sibodan Co., Ltd. under the trade name "Pulsol 1789".

皮膚外用剤に配合する量としては期待する紫外線吸収効
果に応じて任意であるが、極端に配合量が多い場合には
、皮膚外用剤基剤の分量がすくなくなり、好ましくない
。好ましくは0.01〜IQ%である。0.01%以下
では紫外線吸収効果が少なく本来の目的を発揮できず、
10%を越える場合には皮膚外用剤基剤の分量が減り皮
膚外用剤そのものとしての品質が損なわれる。
The amount to be added to the skin external preparation is arbitrary depending on the expected ultraviolet absorption effect, but if the amount is extremely large, the amount of the skin external preparation base will be reduced, which is not preferable. Preferably it is 0.01 to IQ%. If it is less than 0.01%, the UV absorption effect is small and the original purpose cannot be achieved.
If it exceeds 10%, the amount of the skin external preparation base decreases and the quality of the skin external preparation itself is impaired.

また本発明の効果を発揮する目的で配合される炭素数9
ないし31の直鎖、分岐、不飽和アルキル残基を持つ酸
と炭素数9ないし31の直鎖、分岐、不飽和アルキル残
基を持つアルコールのエステルとしては、たとえば2−
ヘキシルデシルミリステート、2−才クチルドデシル−
2°−イソへブチルイソウンデカノエート、オレイルオ
レート、2−へブチルウンデシルパルミテート等の合成
油、あるいは植物油のホホバオイル、深海魚油のオレン
ジラフイー油、ピースワックスなどの天然油などがある
Also, carbon number 9 is blended for the purpose of exhibiting the effects of the present invention.
Examples of the ester of an acid having a straight chain, branched or unsaturated alkyl residue having 9 to 31 carbon atoms and an alcohol having a straight chain, branched or unsaturated alkyl residue having 9 to 31 carbon atoms include 2-
hexyldecyl myristate, 2-year-old cutyldodecyl-
These include synthetic oils such as 2°-isohebutyl isoundecanoate, oleyl oleate, and 2-hebutyl undecyl palmitate, and natural oils such as vegetable oil jojoba oil, deep sea fish oil orange roughy oil, and peace wax. .

これらのエステル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4−
 (1,1−ジメチルエチル)−4°−メトキシジベン
ゾイルメタンの量に対して1/2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。
One or more of these esters may be blended, but the amount blended for the purpose of exhibiting the effects of the present invention is 4-
It is necessary to use at least 1/2 of the amount of (1,1-dimethylethyl)-4°-methoxydibenzoylmethane, and even if it is added in excess, the effects of the present invention will not be impaired.

本発明において4−(1,1−ジメチルエチル)−4°
−メトキシジベンゾイルメタンと炭素数9ないし31の
直鎖、分岐、不飽和アルキル残基を持つ酸と炭素数9な
いし31の直鎖、分岐、不飽和アルキル残基を持つアル
コールのエステル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
In the present invention, 4-(1,1-dimethylethyl)-4°
- A mixture of methoxydibenzoylmethane, an acid having a straight chain, branched, or unsaturated alkyl residue having 9 to 31 carbon atoms, and an ester of an alcohol having a straight chain, branched, or unsaturated alkyl residue having 9 to 31 carbon atoms. As the base for external skin preparations, any conventional skin external preparation base can be used.

すなわち、液状、ゲル状、ペースト状、クリーム状など
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、香料などが併用で伊ることは言う
までもない。
That is, it is in the form of liquid, gel, paste, cream, etc., and the ingredients that modify the external skin preparation include moisturizers, oils, surfactants, thickeners, sequestering agents, other ultraviolet absorbers, drugs, Needless to say, dyes, fragrances, etc. can be used in combination.

[実施例] 〈実施例1〉 サンスクリーンオイル 4−(1,1−ジメチルエチル)     2wt%−
4°−メトキシジベンゾイル メタン グリセリルモノオレート        2ホホバ油 
            20流動パラフイン    
      76[発明の効果] 実施例1は本発明にしたがって4− (1,1−ジメチ
ルエチル)−4′’−メトキシジベンゾイルメタンと、
炭素数9ないし31の直鎖、分岐、不飽和アルキル茂基
を持つ酸と炭素数9ないし31の直鎖、分岐、不飽和ア
ルキル残基を持つアルコールのエステルを配合した皮膚
外用剤である。
[Example] <Example 1> Sunscreen oil 4-(1,1-dimethylethyl) 2wt%-
4°-Methoxydibenzoyl methane glyceryl monooleate 2 Jojoba oil
20 liquid paraffin
76 [Effects of the Invention] Example 1 shows that according to the present invention, 4-(1,1-dimethylethyl)-4''-methoxydibenzoylmethane,
This is an external skin preparation containing an acid having a straight chain, branched, or unsaturated alkyl group having 9 to 31 carbon atoms and an ester of an alcohol having a straight chain, branched, or unsaturated alkyl residue having 9 to 31 carbon atoms.

一方、4−(1,1−ジメチルエチル)−4°−メトキ
シジベンゾイルメタンを配合しない場合、およびエステ
ルを配合しない場合を対照例として下記に示す。
On the other hand, the case where 4-(1,1-dimethylethyl)-4°-methoxydibenzoylmethane is not blended and the case where ester is not blended are shown below as control examples.

〈対照例1〉 4− (1,1−ジメチルエチル)     2wt%
−4′−メトキシジベンゾイル メタン グリセリルモノオレート        2流動パラフ
イン          96く対照例2〉 グリセリルモノオレート        2wt%ホホ
バ油             20流動パラフイン 
         78表1に保存安定性および紫外線
防御効果を示す。
<Control example 1> 4-(1,1-dimethylethyl) 2wt%
-4'-methoxydibenzoylmethane glyceryl monooleate 2 liquid paraffin 96 Control example 2> Glyceryl monooleate 2 wt% jojoba oil 20 liquid paraffin
78 Table 1 shows the storage stability and UV protection effect.

実施例1および対照例1.2の皮膚外用剤はいずれもサ
ンスクリーンオイルとして使用されるものである。
The skin external preparations of Example 1 and Control Examples 1.2 are both used as sunscreen oils.

対照例1は製造厘後は均一な液状であるものの4− (
1,1−ジメチルエチル)−4°−メトキシジベンゾイ
ルメタンが徐々に析出し皮膚外用剤としての品質が劣化
し紫外線防御効果ざえも減少してくる。
Control example 1 was a homogeneous liquid after production, but 4-(
1,1-dimethylethyl)-4[deg.]-methoxydibenzoylmethane gradually precipitates, deteriorating its quality as an external skin preparation and reducing its ultraviolet protection effect.

対照例2は結晶が析出することはないが紫外線防御効果
については当然期待できない。
In Control Example 2, no crystals were precipitated, but of course no UV protection effect could be expected.

これに対し実施例1は、製造1後はもちろん長期間保存
したあとでも結晶が析出することがなく、紫外線防御効
果に優れ、品質が安定している。
On the other hand, in Example 1, no crystals were precipitated not only after production but also after long-term storage, excellent UV protection effect, and stable quality.

これは本発明に係る技術を応用した結果である。This is a result of applying the technology according to the present invention.

(以下余白) 表1.室温保存品の結晶析出 評価  O:析出なし ×:析出あや 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。
(Left below) Table 1. Evaluation of crystal precipitation of products stored at room temperature O: No precipitation ×: Fair precipitation Next, the present invention will be described in detail with more examples, but the present invention is not limited thereto.

(以下余白) 実施例2 実施例2 A、セタノール           3wt%グリセ
リルモノステアレート   2 ステアリンM3 ワセリン            3 ホホバ油            3 2−ヘキシルデシルミリステート 4 スクワラン           5 4− (1,1−ジメチルエチル) 2−4′−メトキ
シジベンゾイル メタン 香料             適量 B、プロピレングリコール      3・ 水酸化カ
リウム         (12精製水      全
体を100とする量Aの油相部分とBの水槽部分をそれ
ぞれ70℃で加熱溶解し、Aを已に加え乳化する。その
のち冷却処理をしてクリームを得る。
(Leaving space below) Example 2 Example 2 A, Setanol 3 wt% glyceryl monostearate 2 Stearin M3 Vaseline 3 Jojoba oil 3 2-hexyldecyl myristate 4 Squalane 5 4- (1,1-dimethylethyl) 2-4' -Methoxydibenzoylmethane fragrance Appropriate amount B, Propylene glycol 3. Potassium hydroxide (12 Purified water Amount, taking the whole as 100) Heat and dissolve the oil phase part of A and the water tank part of B at 70℃, then add A. Emulsify and then cool to obtain cream.

実施例3 4− (1,1−ジメチルエチル)  5wt%−4′
−メトキシジベンゾイル メタン 固形パラフィン        2゜ ワセリン            20ヒマシ油   
        4゜ オレイルオレート         5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 3 4-(1,1-dimethylethyl) 5wt%-4'
-Methoxydibenzoylmethane Solid paraffin 2° Vaseline 20 Castor oil
4゜oleyl oleate 5 Mixed coloring agent (red color) 7 Fragrance
Appropriate amounts of each of the above raw materials are heated and melted at 80°C, and then poured into a predetermined container to obtain a lipstick.

(以下余白) 実施例4 A、ステアリルアルコール      2wt%グリセ
リルモノステアレート   2 POE (50)  オレイルエーテル    2ステ
アリン酸          2 精製ラノリン           22−へブチルウ
ンデシル     2 パルミテート 2−オクチルトチ゛シルー2゛−5 イソへブチルイソウンデカノエート 4− (1,1−ジメチルエチル) 2−4゛−メトキ
シジベンゾイル メタン 防腐剤             適量香料     
         適量B5グリセリン       
   5水酸化カリウム         0.2精製
水      全体を100とする量C1調合粉末・ 
          1゜Aの油相原料、Bの水相原料
をそれぞれ70℃で加#、溶解したのちAを已に加えて
乳化する。そのものにCの粉末部を分散処理しついで冷
却処理して、クリーム状ファンデーションを得る。
(Left below) Example 4 A, Stearyl alcohol 2wt% glyceryl monostearate 2 POE (50) Oleyl ether 2 Stearic acid 2 Purified lanolin 22-Hebutylundecyl 2 Palmitate 2-Octylthothiyl 2-5 Isoto Butyl isoundecanoate 4-(1,1-dimethylethyl) 2-4'-methoxydibenzoylmethane Preservative Appropriate amount Fragrance
Appropriate amount of B5 glycerin
5 Potassium hydroxide 0.2 Purified water Amount to make the whole 100 C1 Mixed powder
1°A oil phase raw material and B water phase raw material were each added at 70°C to dissolve, and then A was added to emulsify. The powder part of C is dispersed therein and then cooled to obtain a cream-like foundation.

実施例5 オレンジラフイー油      50wt%ホホバ油 
          30 流動パラフイン        10 4− (1,1−ジメチルエチル)10−4′−メトキ
シジベンゾイル メタン 色素             aiM香料     
        適量 上記の各成分を50℃で加熱溶解したのち攪拌冷却しボ
ディ用オイルを得る。
Example 5 Orange roughy oil 50wt% jojoba oil
30 Liquid paraffin 10 4-(1,1-dimethylethyl)10-4'-methoxydibenzoylmethane dye aiM fragrance
Appropriate amounts of each of the above components are heated and dissolved at 50°C, and then cooled with stirring to obtain a body oil.

(以下余白) 実施例6 固形パラフィン        10wt%流動パラフ
ィン   全体を100とする量ワセリン      
     20 グリセリルモノミリステート10 オレイルオレート         0.054− (
1,1−ジメチルエチル)0.1−4′−メトキシジベ
ンゾイル メタン 色素             適量 香料             適量 上記の各成分を50℃で加熱溶解したのち攪拌冷却しボ
ディ用ゲルを得る。
(Left below) Example 6 Solid paraffin 10wt% liquid paraffin Amount to make the whole 100 Vaseline
20 glyceryl monomyristate 10 oleyl oleate 0.054- (
(1,1-dimethylethyl) 0.1-4'-methoxydibenzoylmethane dye (appropriate amount) Perfume (appropriate amount) Each of the above components was dissolved by heating at 50°C, and then cooled with stirring to obtain a body gel.

★施例2〜6の皮膚外用剤は紫外線吸収効果に優れ、ま
た製造後3ケ月経ても結晶の析出による品質の劣化は皆
無であった。
*The external skin preparations of Examples 2 to 6 had excellent ultraviolet absorption effects, and there was no deterioration in quality due to crystal precipitation even 3 months after production.

これは本発明に係る技術を応用した結果である。This is a result of applying the technology according to the present invention.

Claims (1)

【特許請求の範囲】[Claims] 4−(1,1−ジメチルエチル)−4′−メトキシジベ
ンゾイルメタンとともに炭素数9ないし31の直鎖、分
岐、不飽和アルキル残基を持つ酸と炭素数9ないし31
の直鎖、分岐、不飽和アルキル残基を持つアルコールの
エステルを配合したことを特徴とする皮膚外用剤。
4-(1,1-dimethylethyl)-4'-methoxydibenzoylmethane, an acid having a straight chain, branched, or unsaturated alkyl residue having 9 to 31 carbon atoms, and 4-(1,1-dimethylethyl)-4'-methoxydibenzoylmethane;
A skin external preparation characterized by containing an alcohol ester having a linear, branched, or unsaturated alkyl residue.
JP60056489A 1985-03-20 1985-03-20 External skin preparation Expired - Lifetime JPH0645531B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP60056489A JPH0645531B2 (en) 1985-03-20 1985-03-20 External skin preparation

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP60056489A JPH0645531B2 (en) 1985-03-20 1985-03-20 External skin preparation

Publications (2)

Publication Number Publication Date
JPS61215316A true JPS61215316A (en) 1986-09-25
JPH0645531B2 JPH0645531B2 (en) 1994-06-15

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JP60056489A Expired - Lifetime JPH0645531B2 (en) 1985-03-20 1985-03-20 External skin preparation

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH03170416A (en) * 1989-11-10 1991-07-24 Unilever Nv Anti-sunburn composition
WO1994021223A1 (en) * 1993-03-16 1994-09-29 Unilever Plc Skin emollients
EP0791353A1 (en) * 1996-02-26 1997-08-27 Shiseido Company Limited Ultraviolet absorbing composition
FR2768730A1 (en) * 1997-09-25 1999-03-26 Jean Noel Thorel Photostabilization of 4-(tert.butyl)-4'-methoxy dibenzoylmethane against UV
WO2005110482A1 (en) * 2004-05-13 2005-11-24 Hisamitsu Pharmaceutical Co., Inc. Percutaneous pharmaceutical preparation for external use containing nonsteroidal antiinflammatory analgesic

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6056488A (en) * 1983-09-08 1985-04-02 Kishimoto Akira Method and device for producing welded can body

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6056488A (en) * 1983-09-08 1985-04-02 Kishimoto Akira Method and device for producing welded can body

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH03170416A (en) * 1989-11-10 1991-07-24 Unilever Nv Anti-sunburn composition
WO1994021223A1 (en) * 1993-03-16 1994-09-29 Unilever Plc Skin emollients
EP0791353A1 (en) * 1996-02-26 1997-08-27 Shiseido Company Limited Ultraviolet absorbing composition
US5849272A (en) * 1996-02-26 1998-12-15 Shiseido Co., Ltd. Ultraviolet absorbing composition
FR2768730A1 (en) * 1997-09-25 1999-03-26 Jean Noel Thorel Photostabilization of 4-(tert.butyl)-4'-methoxy dibenzoylmethane against UV
WO2005110482A1 (en) * 2004-05-13 2005-11-24 Hisamitsu Pharmaceutical Co., Inc. Percutaneous pharmaceutical preparation for external use containing nonsteroidal antiinflammatory analgesic

Also Published As

Publication number Publication date
JPH0645531B2 (en) 1994-06-15

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