JP2017008000A - Ester oil - Google Patents
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Abstract
Description
本発明は、シリコーン油を始めとする各種油剤との相溶性に優れ、皮膚や毛髪等に適用した場合に、優れた使用感をもたらすことが望まれるエステル油剤に関する。 The present invention relates to an ester oil agent that is excellent in compatibility with various oil agents including silicone oil, and that is desired to provide excellent usability when applied to skin, hair, and the like.
化粧料用のエステル油剤に求められる機能は用途により異なるが、化粧料及び皮膚外用剤に用いられる他の油性成分との相溶性に優れること、肌なじみやコク感等の使用感に優れること、クレンジング力に優れること、粉体の分散性に優れることなどが挙げられる。 The functions required of cosmetic ester oils vary depending on the application, but are excellent in compatibility with other oily components used in cosmetics and skin external preparations, excellent in feeling of use such as skin familiarity and richness, Examples thereof include excellent cleansing power and excellent powder dispersibility.
特に近年、良好な使用感を求めてシリコーン類が化粧料及び皮膚外用剤に多用されるようになり、化粧料用及び皮膚外用剤用のエステル油剤の機能として、シリコーン類との相溶性に優れることを求める傾向が強くなっている。 Particularly in recent years, silicones have been frequently used in cosmetics and skin external preparations in search of a good feeling of use, and as a function of ester oils for cosmetics and skin external preparations, they are excellent in compatibility with silicones. There is a growing tendency to seek.
このようなシリコーン類との相溶性に優れるエステル油剤としては、イソノナン酸イソノニルや飽和分岐二価アルコールとネオペンタン酸とのジエステルなどが提案されている（例えば、特許文献１参照。）。
また、肌なじみやコク感等の使用感に優れるエステル油剤としては、イソステアリン酸イソステアリルなどが提案されている。
As ester oil agents excellent in compatibility with such silicones, isononyl isononanoate, diesters of saturated branched dihydric alcohols and neopentanoic acid have been proposed (for example, see Patent Document 1).
In addition, as an ester oil agent excellent in feeling of use such as skin familiarity and richness, isostearyl isostearate has been proposed.
しかしながら、従来のエステル類は必ずしも化粧料用のエステル油剤に求められる機能の全てを満足するものではなかった。すなわち、汎用されているイソノナン酸イソノニルや飽和分岐二価アルコールとネオペンタン酸とのジエステルなどは、シリコーン類との相溶性に優れるが、肌なじみやコク感等の使用感は良くないなどの欠点を有している。
また、汎用されているイソステアリン酸イソステアリルは肌なじみやコク感等の使用感も十分ではなく、シリコーン類との相溶性が良くないなどの欠点を有している。
このような背景から、化粧料に用いられるシリコーン類を始めとした油性成分との相溶性に優れ、かつ肌なじみやコク感等の使用感に優れるエステル油剤が望まれていた。
However, conventional esters do not always satisfy all of the functions required for ester oils for cosmetics. In other words, isononyl isononanoate and diesters of saturated branched dihydric alcohol and neopentanoic acid, which are widely used, have excellent compatibility with silicones, but have disadvantages such as poor skin feel and rich feeling. Have.
Further, isostearyl isostearate, which is widely used, has drawbacks such as poor skin compatibility and rich feeling, and poor compatibility with silicones.
From such a background, there has been a demand for an ester oil agent that is excellent in compatibility with oily components such as silicones used in cosmetics and is excellent in use feeling such as skin familiarity and richness.
本発明は、化粧料に用いられるシリコーン類を始めとする油性成分との相溶性に優れ、かつ肌なじみやコク感等の使用感に優れるエステル油剤を提供することを目的とする。 An object of this invention is to provide the ester oil agent which is excellent in compatibility with oily components including silicones used for cosmetics, and is excellent in use feelings, such as skin familiarity and richness.
本発明者らは上記課題を解決すべく検討を行った結果、特定の分岐構造を有する脂肪酸とアルコールからなるエステル油剤が、シリコーン類を始めとする油性成分との相溶性に優れ、かつ肌なじみやコク感等の使用感に優れることを見出し、本発明を完成させた。 As a result of studies conducted by the present inventors to solve the above-mentioned problems, an ester oil agent comprising a fatty acid having a specific branched structure and an alcohol is excellent in compatibility with oily components such as silicones and is familiar to the skin. As a result, the present invention was completed.
本発明により、シリコーン類との相溶性に優れ、かつ肌なじみやコク感等の使用感に優れるエステル油剤を得ることができる。また、本発明により、上記の優れた機能を持つエステル油剤を用いることで、特徴的な化粧料又は皮膚外用剤を製造することができる。 By this invention, the ester oil agent which is excellent in compatibility with silicones, and is excellent in use feelings, such as skin familiarity and richness, can be obtained. Further, according to the present invention, a characteristic cosmetic or skin external preparation can be produced by using the ester oil agent having the above-mentioned excellent function.
以下、本発明について詳細に説明する。
本発明の優れた機能を発現させるためには、特定の分岐構造を有する脂肪酸とアルコールからなるエステル油剤を用いることが必須である。
ここで特定の分岐構造を有する脂肪酸としては、例えば、１６−メチルヘプタデカン酸、２−オクチルデカン酸、２−（４−メチルヘキシル）−８−メチルデカン酸、２−（１，３，３−トリメチルブチル）−５，７，７−トリメチルオクタン酸が挙げられ、好ましくは２−オクチルデカン酸、２−（４−メチルヘキシル）−８−メチルデカン酸、さらに好ましくは２−（１，３，３−トリメチルブチル）−５，７，７−トリメチルオクタン酸である。
Hereinafter, the present invention will be described in detail.
In order to develop the excellent function of the present invention, it is essential to use an ester oil agent composed of a fatty acid having a specific branched structure and an alcohol.
Examples of fatty acids having a specific branched structure include 16-methylheptadecanoic acid, 2-octyldecanoic acid, 2- (4-methylhexyl) -8-methyldecanoic acid, 2- (1,3,3- Trimethylbutyl) -5,7,7-trimethyloctanoic acid, preferably 2-octyldecanoic acid, 2- (4-methylhexyl) -8-methyldecanoic acid, more preferably 2- (1,3,3). -Trimethylbutyl) -5,7,7-trimethyloctanoic acid.
特定の分岐構造を有するアルコールとしては、例えば、２−オクチルデカノール、２−（４−メチルヘキシル）−８−メチルデカノール、２−（１，３，３−トリメチルブチル）−５，７，７−トリメチルオクタノール、２−オクチルドデカノール、２−ヘキシルデカノールが挙げられるが、好ましくは２−（１，３，３−トリメチルブチル）−５，７，７−トリメチルオクタノールである。 Examples of the alcohol having a specific branched structure include 2-octyldecanol, 2- (4-methylhexyl) -8-methyldecanol, 2- (1,3,3-trimethylbutyl) -5,7, Although 7-trimethyloctanol, 2-octyldodecanol, and 2-hexyldecanol are mentioned, 2- (1,3,3-trimethylbutyl) -5,7,7-trimethyloctanol is preferable.
本発明のエステル油剤の製造方法は必ずしも限定されないが、前記脂肪酸より選ばれる少なくとも１種以上の脂肪酸と、前記アルコールより選ばれる少なくとも１種以上のアルコールをリン酸触媒下にて２００〜２６０℃で脱水縮合反応を行う。得られたエステル油剤に対して、例えばカラム精製や分子蒸留を行うことで遊離の脂肪酸やアルコールを除去し、純度が９０重量％以上のエステル油剤を得ることができる。 Although the manufacturing method of the ester oil agent of this invention is not necessarily limited, At least 1 or more types of alcohol chosen from the said fatty acid and at least 1 or more types of alcohol chosen from the said alcohol are 200-260 degreeC under a phosphoric acid catalyst. Perform dehydration condensation reaction. For example, by performing column purification or molecular distillation on the obtained ester oil agent, free fatty acids and alcohol can be removed, and an ester oil agent having a purity of 90% by weight or more can be obtained.
得られた本発明であるエステル油剤は、例えば、１６−メチルヘプタデカン酸２−（１，３，３−トリメチルブチル）−５，７，７−トリメチルオクチル、２−オクチルデカン酸２−オクチルデシル、２−オクチルデカン酸２−（４−メチルヘキシル）−８−メチルデシル、２−オクチルデカン酸２−（１，３，３−トリメチルブチル）−５，７，７−トリメチルオクチル、２−オクチルデカン酸２−オクチルドデシル、２−オクチルデカン酸２−ヘキシルデシル、２−（４−メチルヘキシル）−８−メチルデカン酸２−オクチルデシル、２−（４−メチルヘキシル）−８−メチルデカン酸２−（４−メチルヘキシル）−８−メチルデシル、２−（４−メチルヘキシル）−８−メチルデカン酸２−（１，３，３−トリメチルブチル）−５，７，７−トリメチルオクチル、２−（４−メチルヘキシル）−８−メチルデカン酸２−オクチルドデシル、２−（４−メチルヘキシル）−８−メチルデカン酸２−ヘキシルデシル、２−（１，３，３−トリメチルブチル）−５，７，７−トリメチルオクタン酸２−オクチルデシル、２−（１，３，３−トリメチルブチル）−５，７，７−トリメチルオクタン酸２−（４−メチルヘキシル）−８−メチルデシル、２−（１，３，３−トリメチルブチル）−５，７，７−トリメチルオクタン酸２−（１，３，３−トリメチルブチル）−５，７，７−トリメチルオクチル、２−（１，３，３−トリメチルブチル）−５，７，７−トリメチルオクタン酸２−オクチルドデシル、２−（１，３，３−トリメチルブチル）−５，７，７−トリメチルオクタン酸２−ヘキシルデシルであり、好ましくは１６−メチルヘプタデカン酸２−（１，３，３−トリメチルブチル）−５，７，７−トリメチルオクチル、２−オクチルデカン酸２−（１，３，３−トリメチルブチル）−５，７，７−トリメチルオクチル、２−（４−メチルヘキシル）−８−メチルデカン酸２−（１，３，３−トリメチルブチル）−５，７，７−トリメチルオクチル、２−（１，３，３−トリメチルブチル）−５，７，７−トリメチルオクタン酸２−オクチルデシル、２−（１，３，３−トリメチルブチル）−５，７，７−トリメチルオクタン酸２−（４−メチルヘキシル）−８−メチルデシル、２−（１，３，３−トリメチルブチル）−５，７，７−トリメチルオクタン酸２−（１，３，３−トリメチルブチル）−５，７，７−トリメチルオクチル、２−（１，３，３−トリメチルブチル）−５，７，７−トリメチルオクタン酸２−オクチルドデシル、２−（１，３，３−トリメチルブチル）−５，７，７−トリメチルオクタン酸２−ヘキシルデシルが挙げられる。
本発明であるエステル油剤以外の場合、各種油剤との相溶性に優れ、同時に優れた使用感を有するエステル油剤を提供することはできない。
The obtained ester oil agent of the present invention is, for example, 16-methylheptadecanoic acid 2- (1,3,3-trimethylbutyl) -5,7,7-trimethyloctyl, 2-octyldecanoic acid 2-octyldecyl 2-octyldecanoic acid 2- (4-methylhexyl) -8-methyldecyl, 2-octyldecanoic acid 2- (1,3,3-trimethylbutyl) -5,7,7-trimethyloctyl, 2-octyldecane 2-octyldodecyl acid, 2-hexyldecyl 2-octyldecanoate, 2-octyldecyl 2- (4-methylhexyl) -8-methyldecanoate, 2- (4-methylhexyl) -8-methyldecanoic acid 2- ( 4-methylhexyl) -8-methyldecyl, 2- (4-methylhexyl) -8-methyldecanoic acid 2- (1,3,3-trimethylbutyl) -5,7 7-trimethyloctyl, 2- (4-methylhexyl) -8-methyldecanoic acid 2-octyldodecyl, 2- (4-methylhexyl) -8-methyldecanoic acid 2-hexyldecyl, 2- (1,3,3- Trimethylbutyl) -5,7,7-trimethyloctanoate 2-octyldecyl, 2- (1,3,3-trimethylbutyl) -5,7,7-trimethyloctanoate 2- (4-methylhexyl) -8 -Methyldecyl, 2- (1,3,3-trimethylbutyl) -5,7,7-trimethyloctanoate 2- (1,3,3-trimethylbutyl) -5,7,7-trimethyloctyl, 2- ( 1,3,3-trimethylbutyl) -5,7,7-trimethyloctanoate 2-octyldodecyl, 2- (1,3,3-trimethylbutyl) -5,7,7-trimethyloctane 2-hexyldecyl, preferably 2- (1,3,3-trimethylbutyl) -5,7,7-trimethyloctyl 16-methylheptadecanoate, 2- (1,3,3) 2-octyldecanoate -Trimethylbutyl) -5,7,7-trimethyloctyl, 2- (4-methylhexyl) -8-methyldecanoic acid 2- (1,3,3-trimethylbutyl) -5,7,7-trimethyloctyl, 2 -(1,3,3-trimethylbutyl) -5,7,7-trimethyloctanoic acid 2-octyldecyl, 2- (1,3,3-trimethylbutyl) -5,7,7-trimethyloctanoic acid 2- (4-Methylhexyl) -8-methyldecyl, 2- (1,3,3-trimethylbutyl) -5,7,7-trimethyloctanoic acid 2- (1,3,3-trimethylbutyl) -5,7, 7-to Limethyloctyl, 2- (1,3,3-trimethylbutyl) -5,7,7-trimethyloctanoate 2-octyldodecyl, 2- (1,3,3-trimethylbutyl) -5,7,7- An example is 2-hexyldecyl trimethyloctanoate.
In the case other than the ester oil agent of the present invention, it is not possible to provide an ester oil agent that is excellent in compatibility with various oil agents and at the same time has an excellent feeling of use.
前記本発明品が配合されうる化粧料は特に限定されるものではなく、乳液、クレンジングクリーム、リップクリーム、ハンドクリーム、サンスクリーン剤等の皮膚化粧料、メイクアップベースクリーム、リキッド及びパウダーファンデーション、アイカラー、チークカラー等のメイクアップ化粧料、リップスティック、リップグロス等の口紅用組成物、ヘアークリーム、ヘアトリートメント等の毛髪用化粧料、ボディローション、ボディクリーム等の身体用化粧料が挙げられるが、リッチな使用感を与えるコク感に優れることが望ましい。
次に実施例をあげて本発明をより詳細に説明するが、本発明はこれらにより限定されるものではない。配合量は全て質量％で表されるものである。
Cosmetics to which the product of the present invention can be blended are not particularly limited, and skin cosmetics such as milky lotion, cleansing cream, lip balm, hand cream, sunscreen agent, makeup base cream, liquid and powder foundation, eye Examples include makeup cosmetics such as color and teak color, lipstick compositions such as lipsticks and lip gloss, hair cosmetics such as hair creams and hair treatments, and body cosmetics such as body lotions and body creams. It is desirable to have a rich feeling that gives a rich feeling of use.
EXAMPLES Next, although an Example is given and this invention is demonstrated in detail, this invention is not limited by these. All compounding amounts are expressed by mass%.
実施例１
１６−メチルヘプタデカン酸２−（１，３，３−トリメチルブチル）−５，７，７−トリメチルオクチルの製造方法
攪拌機、温度計、ガス挿入管を備えた１Ｌの反応器に１６−メチルヘプタデカン酸３５８．７５ｇ（１．０モル）と２−（１，３，３−トリメチルブチル）−５，７，７−トリメチルオクタノール３４１．２５ｇ（１．０モル）を量り込んだ。リン酸触媒下にて質素を吹き込みながら２４０℃で１２ｈ加熱反応させた。反応終了後のサンプル２３０ｇをヘキサン２３０ｇで希釈し、２００ｇのシリカゲルを充填したカラムに通液し、２３０ｇのヘキサンで押出しを実施した。得られたサンプルに含まれるヘキサンをエバポレーターで完全に除去し、純度９０％以上の本発明品Ａ−３を得た。
Example 1
Method for producing 16-methylheptadecanoic acid 2- (1,3,3-trimethylbutyl) -5,7,7-trimethyloctyl 16-methylhepta in a 1 L reactor equipped with a stirrer, thermometer and gas insertion tube 358.75 g (1.0 mol) of decanoic acid and 341.25 g (1.0 mol) of 2- (1,3,3-trimethylbutyl) -5,7,7-trimethyloctanol were weighed in. The reaction was conducted by heating at 240 ° C. for 12 hours while blowing the raw material under a phosphoric acid catalyst. 230 g of the sample after completion of the reaction was diluted with 230 g of hexane, passed through a column packed with 200 g of silica gel, and extruded with 230 g of hexane. Hexane contained in the obtained sample was completely removed with an evaporator to obtain the product A-3 of the present invention having a purity of 90% or more.
実施例２
２−オクチルデカン酸２−オクチルデシルの製造方法
攪拌機、温度計、ガス挿入管を備えた１Ｌの反応器に２−オクチルデカン酸３５８．７５ｇ（１．０モル）と２−オクチルデカノール３４１．２５ｇ（１．０モル）を量り込んだ。その後の反応・精製は実施例１と同条件で実施し、純度９０％以上の本発明品Ｂ−１を得た。
Example 2
Production method of 2-octyldecyl 2-octyldecanoate In a 1 L reactor equipped with a stirrer, a thermometer, and a gas insertion tube, 358.75 g (1.0 mol) of 2-octyldecanoic acid and 2-octyldecanol 341. 25 g (1.0 mol) was weighed out. The subsequent reaction and purification were carried out under the same conditions as in Example 1 to obtain the product B-1 of the present invention having a purity of 90% or more.
実施例３
２−オクチルデカン酸２−（４−メチルヘキシル）−８−メチルデシルの製造方法
攪拌機、温度計、ガス挿入管を備えた１Ｌの反応器に２−オクチルデカン酸３５８．７５ｇ（１．０モル）と２−（４−メチルヘキシル）−８−メチルデカノール３４１．２５ｇ（１．０モル）を量り込んだ。その後の反応・精製は実施例１と同条件で実施し、純度９０％以上の本発明品Ｂ−２を得た。
Example 3
Production method of 2- (4-methylhexyl) -8-methyldecyl 2-octyldecanoate In a 1 L reactor equipped with a stirrer, thermometer and gas insertion tube, 358.75 g (1.0 mol) of 2-octyldecanoic acid And 341.25 g (1.0 mol) of 2- (4-methylhexyl) -8-methyldecanol were weighed. The subsequent reaction and purification were carried out under the same conditions as in Example 1 to obtain the product B-2 of the present invention having a purity of 90% or more.
実施例４
２−オクチルデカン酸２−（１，３，３−トリメチルブチル）−５，７，７−トリメチルオクチルの製造方法
攪拌機、温度計、ガス挿入管を備えた１Ｌの反応器に２−オクチルデカン酸３５８．７５ｇ（１．０モル）と２−（１，３，３−トリメチルブチル）−５，７，７−トリメチルオクタノール３４１．２５ｇ（１．０モル）を量り込んだ。その後の反応・精製は実施例１と同条件で実施し、純度９０％以上の本発明品Ｂ−３を得た。
Example 4
2-octyldecanoic acid production method of 2- (1,3,3-trimethylbutyl) -5,7,7-trimethyloctyl 2-octyldecanoic acid in a 1 L reactor equipped with a stirrer, thermometer and gas insertion tube 358.75 g (1.0 mol) and 2- (1,3,3-trimethylbutyl) -5,7,7-trimethyloctanol 341.25 g (1.0 mol) were weighed in. The subsequent reaction / purification was carried out under the same conditions as in Example 1 to obtain the product B-3 of the present invention having a purity of 90% or more.
実施例５
２−オクチルデカン酸２−オクチルドデシルの製造方法
攪拌機、温度計、ガス挿入管を備えた１Ｌの反応器に２−オクチルデカン酸３４１．６０ｇ（１．０モル）と２−オクチルドデカノール３５８．４０ｇ（１．０モル）を量り込んだ。その後の反応・精製は実施例１と同条件で実施し、純度９０％以上の本発明品Ｂ−４を得た。
Example 5
Method for producing 2-octyldecanoic acid 2-octyldodecyl 2-octyldecanoic acid 341.60 g (1.0 mol) and 2-octyldodecanol 358. were added to a 1 L reactor equipped with a stirrer, thermometer and gas insertion tube. 40 g (1.0 mol) was weighed out. The subsequent reaction and purification were carried out under the same conditions as in Example 1 to obtain the product B-4 of the present invention having a purity of 90% or more.
実施例６
２−オクチルデカン酸２−ヘキシルデシルの製造方法
攪拌機、温度計、ガス挿入管を備えた１Ｌの反応器に２−オクチルデカン酸３７８．００ｇ（１．０モル）と２−ヘキシルデカノール３２２．００ｇ（１．０モル）を量り込んだ。その後の反応・精製は実施例１と同条件で実施し、純度９０％以上の本発明品Ｂ−５を得た。
Example 6
Production method of 2-hexyldecyl 2-octyldecanoate In a 1 L reactor equipped with a stirrer, thermometer, and gas insertion tube, 378.00 g (1.0 mol) of 2-octyldecanoic acid and 322.00 g of 2-hexyldecanol ( 1.0 mol) was weighed out. The subsequent reaction and purification were carried out under the same conditions as in Example 1 to obtain the product B-5 of the present invention having a purity of 90% or more.
実施例７
２−（４−メチルヘキシル）−８−メチルデカン酸２−オクチルデシルの製造方法
攪拌機、温度計、ガス挿入管を備えた１Ｌの反応器に２−（４−メチルヘキシル）−８−メチルデカン酸３５８．７５ｇ（１．０モル）と２−オクチルデカノール３４１．２５ｇ（１．０モル）を量り込んだ。その後の反応・精製は実施例１と同条件で実施し、純度９０％以上の本発明品Ｃ−１を得た。
Example 7
Method for producing 2- (4-methylhexyl) -8-methyldecanoic acid 2-octyldecyl 2- (4-methylhexyl) -8-methyldecanoic acid 358 in a 1 L reactor equipped with a stirrer, thermometer and gas insertion tube .75 g (1.0 mol) and 341.25 g (1.0 mol) of 2-octyldecanol were weighed. The subsequent reaction and purification were carried out under the same conditions as in Example 1 to obtain the product C-1 of the present invention having a purity of 90% or more.
実施例８
２−（４−メチルヘキシル）−８−メチルデカン酸２−（４−メチルヘキシル）−８−メチルデシルの製造方法
攪拌機、温度計、ガス挿入管を備えた１Ｌの反応器に２−（４−メチルヘキシル）−８−メチルデカン酸３５８．７５ｇ（１．０モル）と２−（４−メチルヘキシル）−８−メチルデカン酸２−（４−メチルヘキシル）−８−メチルデカノール３４１．２５ｇ（１．０モル）を量り込んだ。その後の反応・精製は実施例１と同条件で実施し、純度９０％以上の本発明品Ｃ−２を得た。
Example 8
Method for producing 2- (4-methylhexyl) -8-methyldecanoic acid 2- (4-methylhexyl) -8-methyldecyl 2- (4-methylhexyl) was added to a 1 L reactor equipped with a stirrer, thermometer and gas insertion tube. Hexyl) -8-methyldecanoic acid 358.75 g (1.0 mol) and 2- (4-methylhexyl) -8-methyldecanoic acid 2- (4-methylhexyl) -8-methyldecanol 341.25 g (1. 0 mol) was weighed out. The subsequent reaction and purification were carried out under the same conditions as in Example 1 to obtain the product C-2 of the present invention having a purity of 90% or more.
実施例９
２−（４−メチルヘキシル）−８−メチルデカン酸２−（１，３，３−トリメチルブチル）−５，７，７−トリメチルオクチルの製造方法
攪拌機、温度計、ガス挿入管を備えた１Ｌの反応器に２−（４−メチルヘキシル）−８−メチルデカン酸３５８．７５ｇ（１．０モル）と２−（１，３，３−トリメチルブチル）−５，７，７−トリメチルオクタノール３４１．２５ｇ（１．０モル）を量り込んだ。その後の反応・精製は実施例１と同条件で実施し、純度９０％以上の本発明品Ｃ−３を得た。
Example 9
2- (4-Methylhexyl) -8-methyldecanoic acid 2- (1,3,3-trimethylbutyl) -5,7,7-trimethyloctyl production method 1 L equipped with stirrer, thermometer and gas insertion tube In the reactor, 358.75 g (1.0 mol) of 2- (4-methylhexyl) -8-methyldecanoic acid and 341.25 g of 2- (1,3,3-trimethylbutyl) -5,7,7-trimethyloctanol (1.0 mol) was weighed out. The subsequent reaction and purification were carried out under the same conditions as in Example 1 to obtain the product C-3 of the present invention having a purity of 90% or more.
実施例１０
２−（４−メチルヘキシル）−８−メチルデカン酸２−オクチルドデシルの製造方法
攪拌機、温度計、ガス挿入管を備えた１Ｌの反応器に２−（４−メチルヘキシル）−８−メチルデカン酸３４１．６０ｇ（１．０モル）と２−オクチルドデカノール３５８．４０ｇ（１．０モル）を量り込んだ。その後の反応・精製は実施例１と同条件で実施し、純度９０％以上の本発明品Ｃ−４を得た。
Example 10
Method for producing 2- (4-methylhexyl) -8-methyldecanoic acid 2-octyldodecyl 2- (4-methylhexyl) -8-methyldecanoic acid 341 in a 1 L reactor equipped with a stirrer, thermometer and gas insertion tube .60 g (1.0 mol) and 2-octyldodecanol 358.40 g (1.0 mol) were weighed. The subsequent reaction and purification were carried out under the same conditions as in Example 1 to obtain the product C-4 of the present invention having a purity of 90% or more.
実施例１１
２−（４−メチルヘキシル）−８−メチルデカン酸２−ヘキシルデシルの製造方法
攪拌機、温度計、ガス挿入管を備えた１Ｌの反応器に２−（４−メチルヘキシル）−８−メチルデカン酸３７８．００ｇ（１．０モル）と２−ヘキシルデカノール３２２．００ｇ（１．０モル）を量り込んだ。その後の反応・精製は実施例１と同条件で実施し、純度９０％以上の本発明品Ｃ−５を得た。
Example 11
Method for producing 2-hexyldecyl 2- (4-methylhexyl) -8-methyldecanoate 2- (4-methylhexyl) -8-methyldecanoic acid 378 in a 1 L reactor equipped with a stirrer, thermometer and gas insertion tube 0.000 g (1.0 mol) and 2-hexyldecanol 322.00 g (1.0 mol) were weighed in. The subsequent reaction / purification was carried out under the same conditions as in Example 1 to obtain the product C-5 of the present invention having a purity of 90% or more.
実施例１２
２−（１，３，３−トリメチルブチル）−５，７，７−トリメチルオクタン酸２−オクチルデシルの製造方法
攪拌機、温度計、ガス挿入管を備えた１Ｌの反応器に２−（１，３，３−トリメチルブチル）−５，７，７−トリメチルオクタン酸２９６．１０ｇ（０．７モル）と２−オクチルデカノール４０３．９０ｇ（１．０モル）を量り込んだ。その後の反応・精製は実施例１と同条件で実施し、純度９０％以上の本発明品Ｄ−１を得た。
Example 12
Method for producing 2- (1,3,3-trimethylbutyl) -5,7,7-trimethyloctanoate 2-octyldecyl 2- (1,2-triethyloctylate) was added to a 1 L reactor equipped with a stirrer, thermometer and gas insertion tube. 3,3-Trimethylbutyl) -5,7,7-trimethyloctanoic acid 296.10 g (0.7 mol) and 2-octyldecanol 403.90 g (1.0 mol) were weighed. The subsequent reaction and purification were carried out under the same conditions as in Example 1 to obtain the product D-1 of the present invention having a purity of 90% or more.
実施例１３
２−（１，３，３−トリメチルブチル）−５，７，７−トリメチルオクタン酸２−（４−メチルヘキシル）−８−メチルデシルの製造方法
攪拌機、温度計、ガス挿入管を備えた１Ｌの反応器に２−（１，３，３−トリメチルブチル）−５，７，７−トリメチルオクタン酸２９６．１０ｇ（０．７モル）と２−（４−メチルヘキシル）−８−メチルデカノール４０３．９０ｇ（１．０モル）を量り込んだ。その後の反応・精製は実施例１と同条件で実施し、純度９０％以上の本発明品Ｄ−２を得た。
Example 13
Method for producing 2- (1,3,3-trimethylbutyl) -5,7,7-trimethyloctanoic acid 2- (4-methylhexyl) -8-methyldecyl 1 L equipped with stirrer, thermometer and gas insertion tube In the reactor, 296.10 g (0.7 mol) of 2- (1,3,3-trimethylbutyl) -5,7,7-trimethyloctanoic acid and 2- (4-methylhexyl) -8-methyldecanol 403 .90 g (1.0 mole) was weighed in. The subsequent reaction and purification were carried out under the same conditions as in Example 1 to obtain the product D-2 of the present invention having a purity of 90% or more.
実施例１４
２−（１，３，３−トリメチルブチル）−５，７，７−トリメチルオクタン酸２−（１，３，３−トリメチルブチル）−５，７，７−トリメチルオクチルの製造方法
攪拌機、温度計、ガス挿入管を備えた１Ｌの反応器に２−（１，３，３−トリメチルブチル）−５，７，７−トリメチルオクタン酸２９６．１０ｇ（０．７モル）と２−（１，３，３−トリメチルブチル）−５，７，７−トリメチルオクタノール４０３．９０ｇ（１．０モル）を量り込んだ。その後の反応・精製は実施例１と同条件で実施し、純度９０％以上の本発明品Ｄ−３を得た。
Example 14
Method for producing 2- (1,3,3-trimethylbutyl) -5,7,7-trimethyloctanoic acid 2- (1,3,3-trimethylbutyl) -5,7,7-trimethyloctyl Stirrer, thermometer In a 1 L reactor equipped with a gas insertion tube, 296.10 g (0.7 mol) of 2- (1,3,3-trimethylbutyl) -5,7,7-trimethyloctanoic acid and 2- (1,3 , 3-trimethylbutyl) -5,7,7-trimethyloctanol 403.90 g (1.0 mol) was weighed in. The subsequent reaction and purification were carried out under the same conditions as in Example 1 to obtain the product D-3 of the present invention having a purity of 90% or more.
実施例１５
２−（１，３，３−トリメチルブチル）−５，７，７−トリメチルオクタン酸２−オクチルドデシルの製造方法
攪拌機、温度計、ガス挿入管を備えた１Ｌの反応器に２−（１，３，３−トリメチルブチル）−５，７，７−トリメチルオクタン酸２８０．００ｇ（０．７モル）と２−オクチルドデカノール４２０．００ｇ（１．０モル）を量り込んだ。その後の反応・精製は実施例１と同条件で実施し、純度９０％以上の本発明品Ｄ−４を得た。
Example 15
Method for producing 2- (1,3,3-trimethylbutyl) -5,7,7-trimethyloctanoic acid 2-octyldodecyl 2- (1,1) equipped with a stirrer, thermometer and gas insertion tube 3,3-trimethylbutyl) -5,7,7-trimethyloctanoic acid 280.00 g (0.7 mol) and 2-octyldodecanol 420.00 g (1.0 mol) were weighed. The subsequent reaction and purification were carried out under the same conditions as in Example 1 to obtain the product D-4 of the present invention having a purity of 90% or more.
実施例１６
２−（１，３，３−トリメチルブチル）−５，７，７−トリメチルオクタン酸２−ヘキシルデシルの製造方法
攪拌機、温度計、ガス挿入管を備えた１Ｌの反応器に２−（１，３，３−トリメチルブチル）−５，７，７−トリメチルオクタン酸３１５．００ｇ（０．７モル）と２−ヘキシルデカノール３８５．００ｇ（１．０モル）を量り込んだ。その後の反応・精製は実施例１と同条件で実施し、純度９０％以上の本発明品Ｄ−５を得た。
Example 16
Method for producing 2- (1,3,3-trimethylbutyl) -5,7,7-trimethyloctanoic acid 2-hexyldecyl 2- (1,1) equipped with a stirrer, thermometer and gas insertion tube 3,3-trimethylbutyl) -5,7,7-trimethyloctanoic acid 315.00 g (0.7 mol) and 2-hexyldecanol 385.00 g (1.0 mol) were weighed in. The subsequent reaction and purification were carried out under the same conditions as in Example 1 to obtain the product D-5 of the present invention having a purity of 90% or more.
試験例１
ジメチコンとの相溶性
本発明のエステル油剤１６品と、比較例としてイソステアリン酸イソステアリル（高級アルコール工業社製ＩＳＩＳ）、水添ポリイソブテン（日油株式会社製パールリーム６）、イソノナン酸イソノニル（日清オイリオ社製サラコス９９）、特開２００５−２０６５７３号公報記載のジネオペンタン酸メチルペンタンジオール（日本精化社製ネオソリューＭＰ）を用いた。試験はジメチコン（信越化学工業株式会社製ＫＦ−９６Ａ−１００ＣＳ）１０重量％又は５０重量％にそれぞれの油剤を９０重量％又は５０重量％添加し、攪拌下で７０℃まで加熱した。その後常温まで冷却して一晩静置し、相溶性を目視で評価した。
Test example 1
Compatibility with dimethicone 16 products of the ester oil agent of the present invention and, as comparative examples, isostearyl isostearate (ISIS manufactured by Higher Alcohol Industry), hydrogenated polyisobutene (Pearl Ream 6 manufactured by NOF Corporation), isononyl isononanoate (Nisshin) Oilicos Saracos 99) and methylpentanediol dineopentanoate described in JP 2005-206573 A (Neosol MP manufactured by Nippon Seika Co., Ltd.) were used. In the test, 90% by weight or 50% by weight of each oil agent was added to 10% by weight or 50% by weight of dimethicone (KF-96A-100CS manufactured by Shin-Etsu Chemical Co., Ltd.) and heated to 70 ° C. with stirring. Thereafter, the mixture was cooled to room temperature and allowed to stand overnight, and the compatibility was visually evaluated.
結果を下記の評価基準に基づき表１に示す。
３：ジメチコン５０重量％まで相溶
２：ジメチコン１０重量％まで相溶
１：相溶性なし
The results are shown in Table 1 based on the following evaluation criteria.
3: Compatible up to 50% by weight of dimethicone 2: Compatible up to 10% by weight of dimethicone 1: No compatibility
試験例２
皮膚塗布時の使用感
本発明のエステル油剤１６品と、比較例としてイソステアリン酸イソステアリル（高級アルコール工業社製ＩＳＩＳ）、水添ポリイソブテン（日油株式会社製パールリーム６）、イソノナン酸イソノニル（日清オイリオ社製サラコス９９）、特開２００５−２０６５７３号公報記載のジネオペンタン酸メチルペンタンジオール（日本精化社製ネオソリューＭＰ）を用いた。試験はパネラーの左手上腕を市販洗浄剤にて洗浄し、タオルドライ後にスポイトで各油剤を一滴滴下し、指１本で１０回、回しながら馴染ませ、肌なじみとコク感を評価した。評価は専門パネラーに依頼し、５段階で評価した。
Test example 2
Usability at the time of skin application 16 ester oil preparations of the present invention and, as comparative examples, isostearyl isostearate (ISIS manufactured by Higher Alcohol Industry Co., Ltd.), hydrogenated polyisobutene (Pearl Ream 6 manufactured by NOF Corporation), isononyl isononanoate (Japan) Seiakos 99 manufactured by Kiyoi Rio Co., Ltd.) and methylpentanediol dineopentanoate described in JP-A-2005-206573 (Neosol MP manufactured by Nippon Seika Co., Ltd.) were used. In the test, the upper left arm of the panel was washed with a commercially available detergent, and after a towel was dried, a drop of each oil was dropped with a dropper, and it was blended while turning 10 times with one finger to evaluate skin familiarity and richness. Evaluation was requested from a specialized panelist and was evaluated in five stages.
結果を下記の評価基準に基づき表１に示す。
５：かなり優れている
４：優れている
３：普通
２：劣っている
１：かなり劣っている
The results are shown in Table 1 based on the following evaluation criteria.
5: Very good 4: Excellent 3: Normal 2: Inferior 1: Very inferior
試験例３
クレンジング力
本発明のエステル油剤１６品と、比較例としてイソステアリン酸イソステアリル（高級アルコール工業社製ＩＳＩＳ）、水添ポリイソブテン（日油株式会社製パールリーム６）、イソノナン酸イソノニル（日清オイリオ社製サラコス９９）、特開２００５−２０６５７３号公報記載のジネオペンタン酸メチルペンタンジオール（日本精化社製ネオソリューＭＰ）を用いた。試験には市販ファンデーション（株式会社資生堂社製マキアージュ／パーフェクトマルチベース）を用い、バイオスキン上に一定量塗布して１時間乾燥後に試験を行なった。各油剤をスポイトで一滴滴下し、指１本で擦り洗いを２０往復実施してキムワイプにて拭き取りを行った。
Test example 3
Cleansing power 16 ester oil preparations of the present invention and, as comparative examples, isostearyl isostearate (ISIS manufactured by Higher Alcohol Industry Co., Ltd.), hydrogenated polyisobutene (Pearl Ream 6 manufactured by NOF Corporation), isononyl isononanoate (manufactured by Nisshin Oilio Co., Ltd.) Saracos 99) and methylpentanediol dineopentanoate described in JP-A-2005-206573 (Neosol MP manufactured by Nippon Seika Co., Ltd.) were used. A commercially available foundation (Makiage / Perfect Multibase manufactured by Shiseido Co., Ltd.) was used for the test, and a certain amount was applied onto the bioskin and dried for 1 hour. One drop of each oil was dropped with a dropper, scrubbed with one finger 20 times, and wiped off with Kimwipe.
結果を下記の評価基準に基づき表１に示す。
５：かなり優れている
４：優れている
３：普通
２：劣っている
１：かなり劣っている
The results are shown in Table 1 based on the following evaluation criteria.
5: Very good 4: Excellent 3: Normal 2: Inferior 1: Very inferior
試験例４
粉体分散性
本発明のエステル油剤１６品と、比較例としてイソステアリン酸イソステアリル（高級アルコール工業社製ＩＳＩＳ）、水添ポリイソブテン（日油株式会社製パールリーム６）、イソノナン酸イソノニル（日清オイリオ社製サラコス９９）、特開２００５−２０６５７３号公報記載のジネオペンタン酸メチルペンタンジオール（日本精化社製ネオソリューＭＰ）を用いた。それぞれの油剤に微粒子酸化チタン（テイカ社製ＭＴ−１００ＴＶ）を５重量％添加し、５０ｍｌのファルコンチューブに３０ｍｌ加え、静置２時間後の沈降量から粉体分散性を評価した。
Test example 4
Powder dispersibility 16 ester oil preparations of the present invention and, as comparative examples, isostearyl isostearate (ISIS manufactured by Higher Alcohol Industry Co., Ltd.), hydrogenated polyisobutene (Pearl Ream 6 manufactured by NOF Corporation), isononyl isononanoate (Nisshin Oilio) Salacos 99), and methylpentanediol dineopentanoate described in JP-A-2005-206573 (Neosol MP manufactured by Nippon Seika Co., Ltd.) were used. To each oil agent, 5% by weight of fine particle titanium oxide (MT-100TV manufactured by Teika) was added, 30 ml was added to a 50 ml Falcon tube, and the powder dispersibility was evaluated from the sedimentation amount after 2 hours of standing.
結果を下記の評価基準に基づき表１に示す。
５：沈降量０−５ｍｌ
４：沈降量５−１０ｍｌ
３：沈降量１０−１５ｍｌ
２：沈降量１５−２０ｍｌ
１：沈降量２０ｍｌ以上
The results are shown in Table 1 based on the following evaluation criteria.
5: Sedimentation amount 0-5ml
4: Sedimentation amount 5-10ml
3: Sedimentation amount 10-15ml
2: Sedimentation amount 15-20ml
1: Sedimentation amount 20ml or more
総合評価
本発明のエステル油剤１６品と、比較例としてイソステアリン酸イソステアリル（高級アルコール工業社製ＩＳＩＳ）、水添ポリイソブテン（日油株式会社製パールリーム６）、イソノナン酸イソノニル（日清オイリオ社製サラコス９９）、特開２００５−２０６５７３号公報記載のジネオペンタン酸メチルペンタンジオール（日本精化社製ネオソリューＭＰ）について、ジメチコンとの相溶性、皮膚塗布時の使用感、クレンジング力、粉体分散性から総合評価を行い、結果を表１に示す。
Comprehensive evaluation 16 ester oil agents of the present invention and, as comparative examples, isostearyl isostearate (ISIS manufactured by Higher Alcohol Industry Co., Ltd.), hydrogenated polyisobutene (Pearl Ream 6 manufactured by NOF Corporation), isononyl isononanoate (manufactured by Nisshin Oilio Co., Ltd.) Saracos 99), methylpentanediol dineopentanoate described in JP-A-2005-206573 (Neosol MP manufactured by Nippon Seika Co., Ltd.), compatibility with dimethicone, usability when applied to the skin, cleansing power, powder dispersibility Comprehensive evaluation was performed and the results are shown in Table 1.
表１の結果から明らかなように、本発明品は油剤との相溶性に優れ、同時に肌なじみやコク感のような使用感も優れている。また、相溶性や使用感に限らずクレンジング力や粉体分散性にも優れている。 As is apparent from the results in Table 1, the product of the present invention is excellent in compatibility with the oil agent, and at the same time, the feeling of use such as skin familiarity and richness is excellent. Moreover, it is excellent not only in compatibility and usability but also in cleansing power and powder dispersibility.
本発明により、上記の優れた機能を持つエステル油剤を用いることで、特徴的な化粧料又は皮膚外用剤を製造することができ産業上貢献大である。 According to the present invention, by using the ester oil agent having the above-described excellent function, a characteristic cosmetic or external preparation for skin can be produced, which is industrially significant.
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| KR20240060590A (en) | 2021-09-09 | 2024-05-08 | 닛신 오일리오그룹 가부시키가이샤 | Liquid oil composition, and cosmetics containing the composition |
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| KR20240060590A (en) | 2021-09-09 | 2024-05-08 | 닛신 오일리오그룹 가부시키가이샤 | Liquid oil composition, and cosmetics containing the composition |
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