JP2005132729A - Cosmetic - Google Patents

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JP2005132729A
JP2005132729A JP2003366976A JP2003366976A JP2005132729A JP 2005132729 A JP2005132729 A JP 2005132729A JP 2003366976 A JP2003366976 A JP 2003366976A JP 2003366976 A JP2003366976 A JP 2003366976A JP 2005132729 A JP2005132729 A JP 2005132729A
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fatty acid
cosmetic
mixed fatty
acid ester
phase
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Jun Imanishi
潤 今西
Yasunori Noguchi
安則 野口
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Sakamoto Yakuhin Kogyo Co Ltd
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Sakamoto Yakuhin Kogyo Co Ltd
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Abstract

<P>PROBLEM TO BE SOLVED: To prepare a cosmetic having a good moist (emollient) feeling in a wide range of cosmetic fields such as a cream, a milky lotion, a lipstick or an ointment by formulating a mixed fatty acid ester having excellent water hydration properties with the cosmetic. <P>SOLUTION: This cosmetic is obtained by formulating the mixed fatty acid ester prepared by carrying out an esterification reaction of a polyglycerol having 2-15 average degree of polymerization calculated from the hydroxyl value with a dimer acid of a 36C aliphatic dibasic acid and a 12-22C saturated fatty acid and/or a 12-22C unsaturated fatty acid. <P>COPYRIGHT: (C)2005,JPO&NCIPI

Description

本発明は、優れた抱水性を有する混合脂肪酸エステルを配合する化粧料に関するものである。   The present invention relates to a cosmetic containing a mixed fatty acid ester having excellent water repellency.

従来、油性原料は化粧品の主要原料として広範囲に使われ、クリームや乳液の重要な成分として、皮膚からの水分の蒸散を抑制したり、使用感触を向上させる等の目的で使用されている。油性原料には植物油、動物油等の天然油性成分、これらの油脂、ロウ類から精製分離された高級アルコールや高級脂肪酸、石油の原油を分留精製して得る炭化水素油類、あるいは合成されたエステルオイルがある。その中でも、ラノリンは優れた抱水性と皮膚親和性から、皮膚保護性が良好な油剤として評価され、基礎化粧料、メークアップ化粧料を始め、多くの化粧料に使用されてきた。しかし、色相及び臭いの点において化粧品原料としては欠点がある。加えて天然物であるため、品質が一定しないことや、長時間のうちに酸敗する等の問題があった。このためラノリンの構成成分の一部を取り出したり、これに他の物質を反応させたラノリン誘導体が開発されているが、ラノリンの最大の特性である抱水性が損なわれているのが現状である。このことから、ラノリンの代替原料について、以前より開発されている。例えば、特許文献1〜2には、抱水性油剤が数品記載されている。しかし、これらの中でラノリンの抱水率を超える、高い抱水性能を有し、且つ植物由来である油剤について記載はない。
特開平11−246354号公報 特開2002−255738号公報
Conventionally, oil-based raw materials have been widely used as the main raw materials for cosmetics, and are used as important ingredients in creams and emulsions for the purpose of suppressing the transpiration of moisture from the skin and improving the feeling of use. Oily raw materials include natural oil components such as vegetable oils and animal oils, these fats and oils, higher alcohols and higher fatty acids refined and separated from waxes, hydrocarbon oils obtained by fractional purification of petroleum crude oils, or synthesized esters There is oil. Among them, lanolin has been evaluated as an oil agent with good skin protection due to its excellent water repellency and skin affinity, and has been used in many cosmetics including basic cosmetics and makeup cosmetics. However, it has drawbacks as a cosmetic raw material in terms of hue and odor. In addition, since it is a natural product, there are problems such as inconsistent quality and acidification over a long period of time. For this reason, lanolin derivatives have been developed in which some of the constituents of lanolin are extracted or reacted with other substances, but the water-holding property, which is the greatest characteristic of lanolin, has been impaired. . Therefore, alternative materials for lanolin have been developed. For example, Patent Literatures 1 and 2 describe several water-containing oil agents. However, among these, there is no description of an oil agent having a high water holding performance exceeding the water holding rate of lanolin and derived from plants.
JP 11-246354 A JP 2002-255738 A

本発明が解決しようとする課題は、ラノリンと同等以上の高い抱水性を有する油性原料を開発し、この油性原料を配合した化粧料を提供することである。   The problem to be solved by the present invention is to develop an oily raw material having a high water holding property equal to or higher than that of lanolin, and to provide a cosmetic containing this oily raw material.

本発明者らは、上記問題を解決するため鋭意検討した結果、特定のポリグリセリンと特定の脂肪酸とをエステル化してなる混合脂肪酸エステルが、上記課題を解決し得ることを見出だし、本発明を完成するに至った。即ち、本発明は、水酸基価から算出した平均重合度2〜15のポリグリセリンに、炭素数36の脂肪族二塩基酸のダイマー酸と、炭素数12〜22の飽和脂肪酸及び/又は不飽和脂肪酸とをエステル化反応して得た混合脂肪酸エステルを配合する化粧料に関するものである。   As a result of intensive studies to solve the above problems, the present inventors have found that a mixed fatty acid ester obtained by esterifying a specific polyglycerin and a specific fatty acid can solve the above problems, and It came to be completed. That is, the present invention relates to polyglycerin having an average degree of polymerization of 2 to 15 calculated from the hydroxyl value, dimer acid of an aliphatic dibasic acid having 36 carbon atoms, saturated fatty acid and / or unsaturated fatty acid having 12 to 22 carbon atoms. It is related with the cosmetics which mix | blend the mixed fatty acid ester obtained by esterifying.

本発明の優れた抱水性を有する混合脂肪酸エステルを化粧料に配合することにより、しっとり感が良好な化粧料を得ることができる。また、本発明の混合脂肪酸エステルは、ラノリンの代替原料としての使用も可能である。   By blending the mixed fatty acid ester having excellent water-holding property of the present invention with a cosmetic, a cosmetic with a good moist feeling can be obtained. The mixed fatty acid ester of the present invention can also be used as an alternative raw material for lanolin.

以下に本発明を詳細にする。   The present invention is described in detail below.

本発明の混合脂肪酸エステルに使用する、平均重合度2〜15のポリグリセリンは、水酸基価から算出した平均重合度で2〜15、好ましくは2〜10のポリグリセリンである。   The polyglycerin having an average degree of polymerization of 2 to 15 used in the mixed fatty acid ester of the present invention is a polyglycerin having an average degree of polymerization calculated from the hydroxyl value of 2 to 15, preferably 2 to 10.

また、本発明の混合脂肪酸エステルに使用する、炭素数36の脂肪族二塩基酸であるダイマー酸は、特に限定はなく炭素数18の不飽和脂肪酸を原料とし得られる、ダイマー酸純分が70%以上、好ましくは80%以上のものを使用する。エステル化に用いる混合脂肪酸中のダイマー酸含有率は10〜70重量%、好ましくは20〜50重量%である。上記範囲外では、目的の抱水性を発揮することができない。   The dimer acid, which is an aliphatic dibasic acid having 36 carbon atoms, used for the mixed fatty acid ester of the present invention is not particularly limited, and the dimer acid pure content obtained using an unsaturated fatty acid having 18 carbon atoms as a raw material is 70. % Or more, preferably 80% or more. The dimer acid content in the mixed fatty acid used for esterification is 10 to 70% by weight, preferably 20 to 50% by weight. Outside the above range, the desired water retention cannot be exhibited.

また、混合する脂肪酸である炭素数12〜22の飽和脂肪酸及び/又は不飽和脂肪酸は、特に限定はなく、例えばラウリン酸、ミリスチン酸、ステアリン酸、ベヘニン酸、イソパルミチン酸、イソステアリン酸、オレイン酸、リノール酸、エルカ酸等が挙げられ、これらの1種又は2種以上を使用する。エステル化に用いる混合脂肪酸中、炭素数12〜22の飽和脂肪酸及び/又は不飽和脂肪酸含有率は30〜90重量%、好ましくは40〜80重量%である。上記範囲外では、目的の抱水性を発揮することができない。   Further, the saturated fatty acid and / or unsaturated fatty acid having 12 to 22 carbon atoms, which is a fatty acid to be mixed, is not particularly limited. , Linoleic acid, erucic acid and the like, and one or more of these are used. In the mixed fatty acid used for esterification, the content of saturated fatty acid having 12 to 22 carbon atoms and / or unsaturated fatty acid is 30 to 90% by weight, preferably 40 to 80% by weight. Outside the above range, the desired water retention cannot be exhibited.

本発明のポリグリセリンに対する混合脂肪酸のエステル化率は、70〜100%、好ましくは90〜100%である。エステル化率が70%未満の混合脂肪酸エステルを配合した化粧料は、ベタツキ感が出て使用性の悪いものとなる。   The esterification rate of the mixed fatty acid with respect to the polyglycerol of the present invention is 70 to 100%, preferably 90 to 100%. A cosmetic compounded with a mixed fatty acid ester having an esterification rate of less than 70% is sticky and has poor usability.

本発明の混合脂肪酸エステルの製造方法は、以下の方法で行うことができる。ポリグリセリンに所定量の混合脂肪酸を仕込む。この場合、各脂肪酸を混合してからポリグリセリンに仕込むか、各脂肪酸を一種ずつポリグリセリンに仕込むかは問わず、最終的に各脂肪酸が所定量仕込まれていれば良い。次に混合脂肪酸を仕込んだポリグリセリンに水酸化ナトリウム等のアルカリ触媒を加えた後、常圧もしくは減圧下で、常法に従ってエステル化反応を行う。以上のエステル化反応で得られた混合脂肪酸エステルを用い、公知の化粧料の調製方法によって、本発明の混合脂肪酸エステルを含有してなる化粧料を調製することができる。   The manufacturing method of the mixed fatty acid ester of this invention can be performed with the following method. A predetermined amount of mixed fatty acid is charged into polyglycerin. In this case, it does not matter whether each fatty acid is mixed and then charged into polyglycerin or each fatty acid is charged into polyglycerin one by one as long as a predetermined amount of each fatty acid is finally charged. Next, after adding an alkali catalyst such as sodium hydroxide to the polyglycerin charged with the mixed fatty acid, an esterification reaction is carried out according to a conventional method under normal pressure or reduced pressure. A cosmetic comprising the mixed fatty acid ester of the present invention can be prepared by a known cosmetic preparation method using the mixed fatty acid ester obtained by the above esterification reaction.

以下、実施例及び比較例により本発明を具体的に説明するが、本発明の範囲はこれらの実施例により限定されるものではない。   EXAMPLES Hereinafter, although an Example and a comparative example demonstrate this invention concretely, the scope of the present invention is not limited by these Examples.

〈実施例1〉
混合脂肪酸エステルは以下のように合成した。尚、実施例及び比較例に用いたポリグリセリン、脂肪酸は全て植物由来品である。
ジグリセリン100gとベヘニン酸213g、オレイン酸340g、ダイマー酸172gから成る混合脂肪酸を反応容器に入れ、0.2gの水酸化ナトリウムを加えた後、窒素気流下において250℃、10時間の条件下で反応を行い、混合脂肪酸エステル782gを得た。
<Example 1>
The mixed fatty acid ester was synthesized as follows. In addition, all the polyglycerol and fatty acid used for the Example and the comparative example are plant origin products.
A mixed fatty acid consisting of 100 g of diglycerin, 213 g of behenic acid, 340 g of oleic acid, and 172 g of dimer acid is put in a reaction vessel, 0.2 g of sodium hydroxide is added, and then under a nitrogen stream at 250 ° C. for 10 hours. Reaction was performed to obtain 782 g of mixed fatty acid ester.

〈実施例2〉
ジグリセリン100gとベヘニン酸107g、オレイン酸340g、ダイマー酸345gから成る混合脂肪酸を反応容器に入れ、実施例1と同様の条件で反応を行い、混合脂肪酸エステル842gを得た。
<Example 2>
A mixed fatty acid consisting of 100 g of diglycerin, 107 g of behenic acid, 340 g of oleic acid, and 345 g of dimer acid was placed in a reaction vessel and reacted under the same conditions as in Example 1 to obtain 842 g of a mixed fatty acid ester.

〈比較例1〉
混合脂肪酸エステルは以下のように合成した。
ジグリセリン100gとベヘニン酸427g、オレイン酸340g、を反応容器に入れ、実施例1と同様の条件で反応を行い、混合脂肪酸エステル823gを得た。
<Comparative example 1>
The mixed fatty acid ester was synthesized as follows.
100 g of diglycerin, 427 g of behenic acid and 340 g of oleic acid were put in a reaction vessel and reacted under the same conditions as in Example 1 to obtain 823 g of a mixed fatty acid ester.

〈比較例2〉
ジグリセリン100gとオレイン酸679gを反応容器に入れ、実施例1と同様の条件で反応を行い、脂肪酸エステル736gを得た。
<Comparative example 2>
100 g of diglycerin and 679 g of oleic acid were put in a reaction vessel and reacted under the same conditions as in Example 1 to obtain 736 g of a fatty acid ester.

(抱水性試験)
実施例及び比較例で得られた試料1gとワセリン9gを撹拌しながら、徐々に水を滴下し、離水するまで抱水させ、試料(10g)に対して抱水された水の量を百分率で示した。測定結果を表1に示す。実施例1〜2の混合脂肪酸エステルは、抱水率がラノリンに比べて200%程度高く、抱水性に優れていることがわかる。一方、比較例1〜2のエステル化物は抱水率の面において不十分な(ラノリンより悪い)結果であった。
(Water retention test)
While stirring 1 g of the sample obtained in Examples and Comparative Examples and 9 g of petroleum jelly, water was gradually added dropwise until water was removed, and the amount of water held in the sample (10 g) was expressed in percentage. Indicated. The measurement results are shown in Table 1. It can be seen that the mixed fatty acid esters of Examples 1 and 2 have a water retention rate of about 200% higher than that of lanolin and are excellent in water retention. On the other hand, the esterified products of Comparative Examples 1 and 2 were insufficient (inferior to lanolin) in terms of water retention.

Figure 2005132729
Figure 2005132729

(化粧料の調製)
前記実施例及び比較例の混合脂肪酸エステルを配合して、各種化粧料を調製した。尚、配合比率及び化粧料の調製方法は、以下の配合実施例1〜4、配合比較例1〜2に記した。また、健常者パネラー20名にて、「しっとり感」、「べたつき感のなさ」等、使用性について官能評価を行った。評価は下記の絶対評価基準に従い、5段階評価し、評点の平均値を、4段階判定基準を用いて判定した。
・絶対評価基準 ・4段階判定基準
(評点):(評価) (評点の平均点) :(判定)
5点:非常に良好 4.5点以上 :◎
4点:良好 4.0点以上4.5点未満:○
3点:普通 3.0点以上4.0点未満:△
2点:やや不良 3.0点未満 :×
1点:不良
併せて、各試料を50℃の恒温槽に1ヶ月放置後の外観を目視にて、以下の基準にて経時安定性を評価した。
・基準
状態変化なし :○
分離等の状態変化がある:×
これら、官能評価及び経時安定性評価の結果を表2に示す。配合実施例1〜4の化粧料は、「しっとり感」、「べたつき感のなさ」等の使用性及び経時安定性が優れたものであった。一方、配合比較例1〜2の化粧料は使用性及び経時安定性において満足するものではなかった。
(Preparation of cosmetics)
Various cosmetics were prepared by blending the mixed fatty acid esters of Examples and Comparative Examples. In addition, the blending ratio and the preparation method of cosmetics were described in the following blending examples 1 to 4 and blending comparative examples 1 and 2. In addition, 20 healthy panelists performed sensory evaluations on usability such as “moist feeling” and “no stickiness”. Evaluation was carried out according to the following absolute evaluation criteria in five levels, and the average value of the scores was determined using a four-level criterion.
・ Absolute evaluation criteria ・ 4-step criteria (rating): (evaluation) (average score): (determination)
5 points: Very good 4.5 points or more: ◎
4 points: Good 4.0 points or more and less than 4.5 points: ○
3 points: Normal 3.0 points or more and less than 4.0 points: △
2 points: Slightly less than 3.0 points: ×
1 point: Defect In addition, each sample was visually observed for 1 month in a thermostatic bath at 50 ° C., and the temporal stability was evaluated according to the following criteria.
・ Standard No change in state: ○
There are state changes such as separation: ×
Table 2 shows the results of sensory evaluation and temporal stability evaluation. The cosmetics of Formulation Examples 1 to 4 were excellent in usability such as “moist feeling” and “no stickiness” and stability over time. On the other hand, the cosmetics of Formulation Comparative Examples 1 and 2 were not satisfactory in terms of usability and stability over time.

Figure 2005132729
Figure 2005132729

(1)配合実施例1 エモリエントクリーム
A相 (重量%)
実施例1の混合脂肪酸エステル 5.00
スクワラン 7.50
モノミリスチン酸デカグリセリル 2.00
ステアリン酸 3.50
モノステアリン酸グリセリン 2.00
トリ−2エチルヘキサン酸グリセリル 5.00
B相
グリセリン 7.00
10%−水酸化カリウム水溶液 1.00
精製水 67.00
A相を80℃にて溶解し、これに80℃に加温したB相を徐々に添加していき乳化した。乳化後、35℃まで冷却してエモリエントクリームを得た。
(1) Formulation Example 1 Emollient cream phase A (% by weight)
Mixed fatty acid ester of Example 1 5.00
Squalane 7.50
Decaglyceryl monomyristate 2.00
Stearic acid 3.50
Glycerol monostearate 2.00
Glyceryl tri-2-ethylhexanoate 5.00
Phase B Glycerin 7.00
10% -potassium hydroxide aqueous solution 1.00
Purified water 67.00
Phase A was dissolved at 80 ° C., and phase B heated to 80 ° C. was gradually added to emulsify. After emulsification, the emulsion was cooled to 35 ° C. to obtain an emollient cream.

(2)配合実施例2 ミルキーローション
A相 (重量%)
実施例2の混合脂肪酸エステル 2.50
モノオレイン酸デカグリセリル 1.00
B相
1%−カルボキシビニルポリマー 5.00
10%−水酸化カリウム水溶液 1.00
1,3−ブチレングリコール 5.00
グリセリン 2.00
精製水 83.50
A相を80℃にて溶解し、これに80℃に加温したB相を徐々に添加していき乳化した。乳化後、35℃まで冷却してミルキーローションを得た。
(2) Formulation Example 2 Milky Lotion Phase A (wt%)
Mixed fatty acid ester of Example 2 2.50
Decaglyceryl monooleate 1.00
Phase B 1% -carboxyvinyl polymer 5.00
10% -potassium hydroxide aqueous solution 1.00
1,3-butylene glycol 5.00
Glycerin 2.00
Purified water 83.50
Phase A was dissolved at 80 ° C., and phase B heated to 80 ° C. was gradually added to emulsify. After emulsification, the mixture was cooled to 35 ° C. to obtain a milky lotion.

(3)配合実施例3 口紅
A相 (重量%)
実施例1の混合脂肪酸エステル 20.00
セレシン 23.50
ヒマシ油 27.00
流動パラフィン 15.00
カルナウバロウ 7.00
キャンデリラロウ 5.00
B相
酸化チタン 2.00
赤色系色素 0.50
A相を80℃にて加温して均一溶解した後、冷却しロールミルで均一に練る。これにB相を添加し脱泡後、型に流し込み急冷して口紅を得た。
(3) Formulation Example 3 Lipstick Phase A (wt%)
Mixed fatty acid ester of Example 1 20.00
Ceresin 23.50
Castor oil 27.00
Liquid paraffin 15.00
Carnauba Arrow 7.00
Candelilla Row 5.00
Phase B titanium oxide 2.00
Red pigment 0.50
A phase A is heated at 80 ° C. and uniformly dissolved, then cooled and uniformly kneaded with a roll mill. Phase B was added thereto and defoamed, then poured into a mold and rapidly cooled to obtain lipstick.

(4)配合実施例4 軟膏基剤
A相 (重量%)
実施例2の混合脂肪酸エステル 10.00
流動パラフィン 13.00
ワセリン 10.00
セチルアルコール 10.00
モノイソステアリン酸デカグリセリル 3.00
B相
ラウリル硫酸ナトリウム 1.00
精製水 53.00
A相を80℃にて溶解し、これに80℃に加温したB相を徐々に添加していき乳化した。乳化後、35℃まで冷却して軟膏基剤を得た。
(4) Formulation Example 4 Ointment base A phase (wt%)
Mixed fatty acid ester of Example 2 10.00
Liquid paraffin 13.00
Vaseline 10.00
Cetyl alcohol 10.00
Decaglyceryl monoisostearate3.00
Phase B Sodium lauryl sulfate 1.00
Purified water 53.00
Phase A was dissolved at 80 ° C., and phase B heated to 80 ° C. was gradually added to emulsify. After emulsification, the mixture was cooled to 35 ° C. to obtain an ointment base.

(1)配合比較例1 エモリエントクリーム
A相 (重量%)
比較例1の混合脂肪酸エステル 5.00
スクワラン 7.50
モノミリスチン酸デカグリセリル 2.00
ステアリン酸 3.50
モノステアリン酸グリセリン 2.00
トリ−2エチルヘキサン酸グリセリル 5.00
B相
グリセリン 7.00
10%−水酸化カリウム水溶液 1.00
精製水 67.00
A相を80℃にて溶解し、これに80℃に加温したB相を徐々に添加していき乳化した。乳化後、35℃まで冷却してエモリエントクリームを得た。
(1) Formulation Comparative Example 1 Emollient Cream Phase A (% by weight)
Mixed fatty acid ester of Comparative Example 1 5.00
Squalane 7.50
Decaglyceryl monomyristate 2.00
Stearic acid 3.50
Glycerol monostearate 2.00
Glyceryl tri-2-ethylhexanoate 5.00
Phase B Glycerin 7.00
10% -potassium hydroxide aqueous solution 1.00
Purified water 67.00
Phase A was dissolved at 80 ° C., and phase B heated to 80 ° C. was gradually added to emulsify. After emulsification, the emulsion was cooled to 35 ° C. to obtain an emollient cream.

(2)配合比較例2 ミルキーローション
A相 (重量%)
比較例2の脂肪酸エステル 2.50
モノオレイン酸デカグリセリル 1.00
B相
1%−カルボキシビニルポリマー 5.00
10%−水酸化カリウム水溶液 1.00
1,3−ブチレングリコール 5.00
グリセリン 2.00
精製水 83.50
A相を80℃にて溶解し、これに80℃に加温したB相を徐々に添加していき乳化した。乳化後、35℃まで冷却してミルキーローションを得た。
(2) Formulation Comparative Example 2 Milky Lotion Phase A (wt%)
Fatty acid ester of Comparative Example 2.50
Decaglyceryl monooleate 1.00
Phase B 1% -carboxyvinyl polymer 5.00
10% -potassium hydroxide aqueous solution 1.00
1,3-butylene glycol 5.00
Glycerin 2.00
Purified water 83.50
Phase A was dissolved at 80 ° C., and phase B heated to 80 ° C. was gradually added to emulsify. After emulsification, the mixture was cooled to 35 ° C. to obtain a milky lotion.

本発明の優れた抱水性を有する混合脂肪酸エステルを化粧料に配合することにより、しっとり感が良好な化粧料を得ることができる。また、本発明の混合脂肪酸エステルを配合する化粧料は、しっとり感(エモリエント性)が良好なものとなり、クリーム、ミルキーローション、口紅、軟膏など幅広い用途に利用が可能である。
By blending the mixed fatty acid ester having excellent water-holding property of the present invention with a cosmetic, a cosmetic with a good moist feeling can be obtained. Moreover, the cosmetics containing the mixed fatty acid ester of the present invention have a good moist feeling (emollient) and can be used in a wide range of applications such as creams, milky lotions, lipsticks and ointments.

Claims (1)

水酸基価から算出した平均重合度2〜15のポリグリセリンに、炭素数36の脂肪族二塩基酸のダイマー酸と、炭素数12〜22の飽和脂肪酸及び/又は不飽和脂肪酸とをエステル化反応して得た混合脂肪酸エステルを配合する化粧料。
A polyglycerin having an average degree of polymerization of 2 to 15 calculated from the hydroxyl value is esterified with a dimer acid of an aliphatic dibasic acid having 36 carbon atoms and a saturated fatty acid and / or unsaturated fatty acid having 12 to 22 carbon atoms. Cosmetics containing the mixed fatty acid ester obtained.
JP2003366976A 2003-10-28 2003-10-28 Cosmetic Pending JP2005132729A (en)

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JP2008115091A (en) * 2006-11-01 2008-05-22 Nippon Emulsion Kk Nonionic surfactant, and cosmetic and agent for external use each using the same
DE202008006004U1 (en) 2008-04-30 2008-07-10 Kokyu Alcohol Kogyo Co., Ltd., Narita-shi Oil base and externally applicable preparation containing the same
JP2009533406A (en) * 2006-04-13 2009-09-17 クローダ インターナショナル パブリック リミティド カンパニー Oil phase structurant
WO2010070808A1 (en) 2008-12-16 2010-06-24 高級アルコール工業株式会社 Hydroxyl compounds and cosmetics containing same
US7993631B2 (en) 2006-04-14 2011-08-09 Kokyu Alcohol Kogyo Co., Ltd. Oil base and external preparation containing same
JP2011162492A (en) * 2010-02-10 2011-08-25 Naris Cosmetics Co Ltd Milky cosmetic
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Cited By (13)

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Publication number Priority date Publication date Assignee Title
US9820932B2 (en) 2005-03-10 2017-11-21 Kokyu Alcohol Kogyo Co., Ltd. Cosmetic
JP2009533406A (en) * 2006-04-13 2009-09-17 クローダ インターナショナル パブリック リミティド カンパニー Oil phase structurant
US7993631B2 (en) 2006-04-14 2011-08-09 Kokyu Alcohol Kogyo Co., Ltd. Oil base and external preparation containing same
JP2008115091A (en) * 2006-11-01 2008-05-22 Nippon Emulsion Kk Nonionic surfactant, and cosmetic and agent for external use each using the same
DE202008006004U1 (en) 2008-04-30 2008-07-10 Kokyu Alcohol Kogyo Co., Ltd., Narita-shi Oil base and externally applicable preparation containing the same
WO2010070808A1 (en) 2008-12-16 2010-06-24 高級アルコール工業株式会社 Hydroxyl compounds and cosmetics containing same
KR20110095889A (en) 2008-12-16 2011-08-25 고큐 아르코르 고교 가부시키가이샤 Hydroxyl compounds and cosmetics containing same
US8334400B2 (en) 2008-12-16 2012-12-18 Kokyu Alcohol Kogyo Co., Ltd. Hydroxyl compound and a cosmetic comprising the same
JP2010143834A (en) * 2008-12-16 2010-07-01 Kokyu Alcohol Kogyo Co Ltd Hydroxyl compound and cosmetic comprising the same
JP2011162492A (en) * 2010-02-10 2011-08-25 Naris Cosmetics Co Ltd Milky cosmetic
EP3868809A1 (en) * 2020-02-21 2021-08-25 Nouryon Chemicals International B.V. Biodegradable polyesters for water-resistant water-in-oil suncare formulations
EP3868808A1 (en) * 2020-02-21 2021-08-25 Nouryon Chemicals International B.V. Biodegradable polyesters for water-resistant anhydrous suncare formulations
EP3868810A1 (en) * 2020-02-21 2021-08-25 Nouryon Chemicals International B.V. Biodegradable polyesters for water-resistant oil-in-water suncare formulations

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