JP5000033B2 - Advanced hydrogenated lecithin - Google Patents

Description

【０１３０】
（調製例１）
卵黄由来精製レシチン（組成、ＰＣ：７９．８％；ＰＥ：１３．５％；ＬＰＣ：１．６％；ＳＭ：２．０％；ＬＰＥ：０．８％）２０ｇを、ｎ−ヘキサン、エタノール、および水の１０／２／４（ｖ／ｖ／ｖ）混合溶媒２００ｍＬに溶解し、５％白金−活性炭触媒１ｇを加えた。この混合物を、１．５〜２．０気圧の水素雰囲気中、３０〜３５℃で５２時間撹拌した。反応混合物からセライトを用いて触媒を濾過して除いた。
【０１３１】
濾液を約１４０ｍＬまで減圧濃縮し、温アセトン１４０ｍＬを加えて撹拌後、−１０℃まで約５時間をかけて冷却し、析出した水素添加レシチンを濾取し、減圧下に乾燥した。収量は、１８．０ｇであった。
【０１３２】
必要に応じてエタノールに加熱溶解した後、濃縮・乾燥して残留溶媒をエタノールに置換する。こうして得られた水素添加レシチンは、前記の方法でヨウ素価を精密に測定すると０．０３であった。また、レシチン組成は、ＰＣ：７９．０％；ＰＥ：１２．８％；ＬＰＣ：３．１％；ＳＭ：１．７％；ＬＰＥ：１．８％であった。
【０１３３】
（調製例２）
卵黄由来精製レシチン（組成、ＰＣ：７９．８％；ＰＥ：１３．５％；ＬＰＣ：１．６％；ＳＭ：２．０％；ＬＰＥ：０．８％）２０ｇを、ｎ−ヘキサン、エタノール、および水の１０／２／４（ｖ／ｖ／ｖ）混合溶媒２００ｍＬに溶解し、クエン酸０．４ｇおよび５％パラジウム−活性炭触媒２ｇを加えた。この混合物を、１．５〜２．０気圧の水素雰囲気中、３０〜３５℃で６０時間撹拌した。反応混合物に１４％アンモニア水０．８ｍＬを加えてクエン酸を中和しアンモニウム塩として析出させ、以下、調製例１と同様に処理してヨウ素価を測定した。その結果、ヨウ素価０．０１、レシチン組成：ＰＣ：７９．５％；ＰＥ：１２．５％；ＬＰＣ：３．２％；ＳＭ：１．５％；ＬＰＥ：１．９％の水素添加卵黄レシチン１７．８ｇを得た。
【０１３４】
（調製例３）
ＰＣ含有量６０．５％の卵黄由来精製レシチンを原料として用い、反応時間を５５時間としたこと以外は調製例１と同様にして、ヨウ素価０．１８の水素添加卵黄レシチンを得た。
【０１３５】
（調製例４）
ＰＣ含有量３１．３％の卵黄由来精製レシチンを原料として用い、反応時間を６０時間としたこと以外は調製例１と同様にして、ヨウ素価０．２５の水素添加卵黄レシチンを得た。
【０１３６】
（調製例５）
原料のレシチンとして、ＰＣ含有率８５．６％の大豆レシチンを用いたこと以外は調製例１と同様にして、ヨウ素価０．０９の水素添加大豆レシチンを得た。
【０１３７】
（調製例６）
原料のレシチンとして、ＰＣ含有率７０．４％の大豆レシチンを用いたこと以外は調製例１と同様にして、ヨウ素価０．２１の水素添加大豆レシチンを得た。
【０１３８】
（調製例７）
原料のレシチンとして、ＰＣ含有率３０．６％の大豆レシチンを用いたこと以外は調製例１と同様にして、ヨウ素価０．１６の水素添加卵黄レシチンを得た。
【０１３９】
（調製比較例１）
水素添加反応に使用した溶媒を、ｎ−ヘキサンのみからなる溶媒としたこと以外は調製例１と同様にして、ヨウ素価０．５０の水素添加卵黄レシチンを得た。
【０１４０】
（調製比較例２）
水素添加反応に使用した溶媒を、ｎ−ヘキサンのみからなる溶媒としたこと、および反応時間を２４時間としたこと以外は調製例１と同様にして、ヨウ素価１．８５の水素添加卵黄レシチンを得た。
【０１４１】
（調製比較例３）
水素添加反応に使用した溶媒を、ｎ−ヘキサンのみからなる溶媒としたこと、および反応時間を６０時間としたこと以外は調製例６と同様にして、ヨウ素価０．６２の水素添加大豆レシチンを得た。
【０１４２】
（調製比較例４）
水素添加反応に使用した溶媒を、ｎ−ヘキサンのみからなる溶媒としたこと、および反応時間を２４時間としたこと以外は調製例６と同様にして、ヨウ素価２．３１の水素添加大豆レシチンを得た。
【０１４３】
（実施例１）
調製例１で得た水素添加卵黄レシチン（ヨウ素価０．０３）と、調製例４で得た水素添加卵黄レシチン（ヨウ素価０．２５）と、調製比較例１で作成した水素添加卵黄レシチン（ヨウ素価０．５０）と、調製比較例２で作成した水素添加卵黄レシチン（ヨウ素価１．８５）とをガラス瓶に密封し、５０℃における加速試験で比較した。
【０１４４】
上記の各種水素添加レシチン粉末をガラス瓶に密封して、５０℃で放置し、粉末の色の変化および臭いの変化を観察した。得られた結果を以下の表１に示す。なお、表中で「ＯＫ」とは、悪臭が生じなかったことを示す。
【０１４５】
【表１】

【０１４６】
（実施例２）
調製例５、６ならびに調製比較例３および４で得られた水素添加レシチン粉末をガラス瓶に密封して、５０℃で放置し、粉末の色の変化および臭いの変化を観察した。得られた結果を以下の表２に示す。なお、表中で「ＯＫ」とは、悪臭が生じなかったことを示す。
【０１４７】
【表２】

【０１４８】
（実施例３）
調製例５、ならびに調製比較例３および４で得られた水素添加レシチン粉末を常法に従い配合して、それぞれ中性クリーム（親水軟膏）を得た。得られた中性クリームの配合は、以下の通りである：
白色ワセリン ２５％
ステアリルアルコール １８％
スクアレン ３％
コレステロール ０．３％
プロピレングリコール １０％
ラウリル硫酸ナトリウム １．５％
水素添加レシチン ２％
防腐剤 ０．０４％
（１００％の残りは、精製水である）。
【０１４９】
得られた中性クリームを容器中に密閉し、５０℃で放置し、粉末の色の変化および臭いの変化を観察した。得られた結果を以下の表３に示す。なお、表中で「ＯＫ」とは、悪臭が生じなかったことを示す。
【０１５０】
【表３】

【０１５１】
【発明の効果】
本発明によれば、ヨウ素価が極めて低く、長期保存可能で、極めて安定な、化粧料配合材料やその他の添加物として有用な水素添加レシチンおよびその製造方法が提供される。[0001]
BACKGROUND OF THE INVENTION
The present invention relates to highly hydrogenated lecithin and a method for producing the same.
[0002]
[Prior art]
Lecithin is widely used in various fields such as foods, cosmetics and pharmaceuticals because of its excellent physical properties. Lecithin, especially egg yolk lecithin, has become a valuable cosmetic compounding material because of its excellent emulsifying power, extensibility, and touch, but it has disadvantages such as being colored or giving off an odor during long-term storage. Have. This shortcoming of storage stability is due to the presence of unsaturated fatty acids in the fatty acids that make up phospholipids, and their unsaturated double bonds are easily oxidized during storage.
[0003]
As a method for overcoming this drawback, a method of catalytically hydrogenating an unsaturated double bond in lecithin to hydrogenated lecithin in the presence of hydrogen and a hydrogenation catalyst is known and has already been put into practical use.
[0004]
At this time, the degree of hydrogenation can be determined by how much the iodine value, which is an index of the presence of the unsaturated double bond, decreases. The iodine value is closely related to the stability of hydrogenated lecithin during long-term storage, and hydrogenated lecithin, whose iodine value is almost zero, has extremely high added value as a cosmetic compounding material.
[0005]
Normal lecithin has an iodine value of 60-90. When lecithin is hydrogenated by a conventional hydrogenation method, hydrogenated lecithin having an iodine value of 1 or more can be obtained relatively easily. However, in the conventional method, it is not easy to highly hydrogenate until the iodine value becomes less than 1, particularly less than 0.3, or even close to 0.
[0006]
For example, in the conventional technology of hydrogenation of egg yolk lecithin, various phospholipids present in lecithin are isolated, for example, 95% of phosphatidylcholine (hereinafter also referred to as “PC”) present in the largest amount. An example of hydrogenation to an iodine value of less than 1 after purification as described above and a catalytic hydrogenation reaction is known.
[0007]
However, when the various phospholipids present in egg yolk lecithin are not separated, that is, when lecithin that maintains the natural phospholipid composition ratio is subjected to a catalytic hydrogenation reaction, the iodine value depends on the reaction conditions. Under normal conditions, it could only be lowered to 2-3, and even in the best case, it could only be lowered to about 1.
[0008]
Similarly, in the case of soybean lecithin, there are those with an iodine value of 1 to 0.5, but it was difficult to make it lower.
[0009]
For this reason, conventionally, lecithin having an iodine value of less than 1 or lecithin having an iodine value of less than 0.5 has been difficult to obtain.
[0010]
In particular, there has not yet been reported a technique capable of highly hydrogenating the iodine value to 0.3 or less, and the existence of such highly hydrogenated lecithin has not been known. Furthermore, in the case of egg yolk lecithin, no technology has been reported yet that can highly hydrogenate the iodine value to 0.3 or less while maintaining the composition of various phospholipids of natural lecithin, and such hydrogenation has been highly hydrogenated. The existence of egg yolk lecithin was not known.
[0011]
[Problems to be solved by the invention]
Accordingly, an object of the present invention is to provide a lecithin that can be stored for a long period of time and a method for producing the same. Specifically, an object is to provide hydrogenated lecithin having an iodine value of 0.3 or less, preferably 0.1 or less. Furthermore, it aims at providing the compounding agent using such a lecithin, and providing cosmetics, a pharmaceutical, a functional food, etc. using such a compounding agent.
[0012]
[Means for Solving the Problems]
As a result of intensive studies to produce hydrogenated lecithin having an iodine value of 0.3 or less, preferably 0.1 or less by catalytic hydrogenation of lecithin, the present inventors have completed the following present invention. It was.
[0013]
The hydrogenated lecithin of the present invention is a hydrogenated lecithin having an iodine value of 0.3 or less.
[0014]
In a preferred embodiment, the iodine value is 0.1 or less.
[0015]
In addition, according to the present invention, there is provided natural egg yolk-derived hydrogenated egg yolk lecithin having an iodine value of 0.3 or less and maintaining the composition of phospholipids in natural lecithin.
[0016]
In a preferred embodiment, the hydrogenated egg yolk lecithin has an iodine value of 0.1 or less.
[0017]
The cosmetic composition of the present invention contains hydrogenated lecithin having an iodine value of 0.3 or less.
[0018]
In one embodiment, the hydrogenated lecithin is a hydrogenated lecithin derived from a natural product.
[0019]
In one embodiment, the hydrogenated lecithin is hydrogenated egg yolk lecithin.
[0020]
In one embodiment, the hydrogenated lecithin is hydrogenated soybean lecithin.
[0021]
The method of the present invention is a method for producing hydrogenated lecithin,
Hydrogenation of natural lecithin in a reaction solution containing a mixed solvent of an aliphatic saturated hydrocarbon, an aliphatic alcohol, and water in a hydrogen atmosphere in the presence of a hydrogenation catalyst to an iodine value of 0.3 or less Process. Preferably, the reaction is performed in a reaction solution containing 0.01 to 5% by weight of an organic acid.
[0022]
In one embodiment, the aliphatic saturated hydrocarbon is n-hexane and the aliphatic alcohol is ethanol.
[0023]
In a preferred embodiment, the mixing ratio of the mixed solvent is
As a volume ratio of saturated aliphatic hydrocarbon: aliphatic alcohol: water
100: (20-300): (10-300)
It is.
[0024]
In one embodiment of the production method of the present invention, the method further includes the step of precipitating hydrogenated lecithin from acetone.
[0025]
In another aspect, a solution, emulsion or lysate containing the hydrogenated lecithin of the present invention is provided.
[0026]
In another aspect, a liposome comprising the hydrogenated lecithin of the present invention is provided.
[0027]
In another aspect, a pigment surface-treated with the hydrogenated lecithin of the present invention is provided.
[0028]
DETAILED DESCRIPTION OF THE INVENTION
(Hydrogenated lecithin)
Lecithin is a general term for various phospholipids. In natural lecithin, phosphatidylcholine (PC), phosphatidylethanolamine (PE), lysophosphatidylcholine (LPC), lysophosphatidylethanolamine (LPE), sphingomyelin (SM), phosphatidic acid Etc. exist at a predetermined ratio.
[0029]
Lecithin includes both plant and animal lecithin.
[0030]
As plant lecithin, for example, soy lecithin, rape seed lecithin, sunflower lecithin, safflower lecithin, cottonseed lecithin, corn lecithin, linseed lecithin, sesame lecithin, olive lecithin, rice lecithin, kirirecithin, gray precitin, avocado lecithin, A palm lecithin, a palm lecithin, etc. are mentioned. Each of these is obtained from the plant seed. Soy lecithin is preferred.
[0031]
Plant lecithin is usually separated as a gum when extracting and purifying oils and fats from plant seeds.
[0032]
Soy lecithin is a lecithin obtained from soybeans, and is a mixture of the above phospholipids. There are some variations depending on environmental factors, but generally phosphatidylcholine (PC) is 24-32%, phosphatidylethanolamine. (PE) is 20 to 28%, phosphatidylinositol (PI) is 12 to 20%, and phosphatidic acid (PA) is 3 to 15%.
[0033]
Any known soy lecithin can be used. Soy lecithin may be used in its natural composition. However, you may use what gave the process which raises a phosphatidylcholine (PC) content as needed.
[0034]
Examples of animal lecithin include egg yolk lecithin and lecithin extracted from seafood. Lecithins other than egg yolk lecithin can be used, but egg yolk lecithin is preferred.
[0035]
“Yellow yolk lecithin” is a lecithin derived from egg yolk and is a mixture of the above phospholipids. Generally, phosphatidylcholine (PC) is 75 to 85, although there are some fluctuations depending on chicken food and other environmental factors. %, Phosphatidylethanolamine (PE) 10-20%, and lysophosphatidylcholine (LPC), lysophosphatidylethanolamine (LPE), and sphingomyelin (SM) each present in a few percent.
[0036]
Any known natural egg yolk lecithin can be used. For example, it can be separated and purified from natural egg yolk.
[0037]
Natural egg yolk lecithin is a lecithin extracted from natural egg yolk that has not been hydrogenated and has undergone any other artificial manipulation that can fluctuate the content of unsaturated double bonds. Not lecithin.
[0038]
In egg yolk lecithin, “the composition of the phospholipid is maintained” means that the composition of the phospholipid is not substantially changed except that the unsaturated double bond is hydrogenated. The maximum value of the variation of the composition ratio with respect to is preferably 10% or less, more preferably 5% or less.
[0039]
The iodine value refers to a value expressed by the number of grams with respect to 100 g of a sample by converting the amount of halogen absorbed when lecithin is allowed to act on halogen to iodine. A conventionally known method can be used as a specific method for measuring the iodine value. However, in the case of lecithin having an iodine value of 1 or less, iodine is taken into the liposome formed by lecithin, the reactivity is lowered, the iodine-starch reaction is inhibited, and the iodine value measurement accuracy is lowered. Therefore, in such a case, the iodine value is measured with good accuracy by measuring the iodine value after hydrolyzing lecithin in advance and losing the liposome-forming ability of lecithin. Therefore, the “iodine value” in the present invention refers to a value measured after hydrolyzing lecithin.
[0040]
In the case of natural lecithin which is not hydrogenated, the iodine value is usually 60-90. The iodine value of hydrogenated lecithin obtained conventionally is usually 2 to 10. On the other hand, the highly hydrogenated lecithin of the present invention has an iodine value of 0.3 or less, preferably 0.1 or less, whereby the long-term storage stability is remarkably improved. As a result, the usefulness of the
[0041]
(Production method of hydrogenated lecithin)
Next, the manufacturing method of the hydrogenated lecithin of this invention is demonstrated.
[0042]
The hydrogenated lecithin of the present invention can be produced by hydrogenating natural lecithin in a hydrogen atmosphere in the presence of a hydrogenation catalyst.
[0043]
The hydrogen atmosphere is usually formed by high-purity hydrogen gas, but any other gas can coexist as long as it does not inhibit the catalytic hydrogenation reaction.
[0044]
The organic acid added as a weakly acidic substance to the reaction solution is preferably an organic carboxylic acid, more preferably an organic polyvalent carboxylic acid. For example, citric acid, malic acid, tartaric acid and the like can be suitably used.
[0045]
By slightly adding a weakly acidic substance and tilting the reaction solution to a slightly acidic side, it is considered that the deactivation of the catalyst is suppressed, and as a result, a low iodine value is achieved.
[0046]
As the catalyst used in the hydrogenation reaction of the present invention, any hydrogenation catalyst conventionally used for hydrogenation of unsaturated fats and oils can be used. Specifically, a palladium-containing catalyst and a platinum-containing catalyst such as a palladium-activated carbon catalyst and a platinum-activated carbon catalyst can be used. Most preferred is a platinum / activated carbon catalyst.
[0047]
A larger amount of the catalyst is advantageous, but it is necessary to determine it in consideration of economy, and usually 0.1 to 20 parts by weight is preferable as the weight of the active metal per 100 parts by weight of lecithin. The amount is more preferably 2 to 15 parts by weight, still more preferably 0.2 to 5 parts by weight. When the amount of the catalyst is too large, it is difficult to remove the catalyst after the reaction. However, in order to advance the reaction efficiently, it is preferable that the amount of the catalyst is large. For example, when it is desired to proceed the reaction particularly efficiently, the active metal weight is preferably 0.5 to 5 parts by weight, particularly preferably 0.8 to 2.5 parts by weight per 100 parts by weight of lecithin.
[0048]
Usually, in the catalytic hydrogenation reaction, in addition to the type and amount of catalyst, the type of reaction solvent, the concentration and temperature of the reaction solution, the reaction time, the stirring efficiency, the hydrogen pressure, and the like affect the efficiency of hydrogenation.
[0049]
In particular, in the production method of the present invention, the reaction solvent, the reaction temperature, the concentration of the reaction solution, the reaction time, and the post-treatment method can have a particular influence.
[0050]
In the method of the present invention, the selection of the reaction solvent is particularly important. Conventionally, the hydrogenation reaction of lecithin is carried out in an aliphatic saturated hydrocarbon solvent such as n-hexane or n-heptane. In some cases, aliphatic alcohols such as methanol, ethanol, and isopropyl alcohol are used in combination with these aliphatic saturated hydrocarbons. However, in these solvents, usually only hydrogenated lecithin having an iodine value of about 1 to 3 can be obtained.
[0051]
According to the method of the present invention, hydrogenated lecithin having a very low iodine value can be obtained by carrying out the reaction in a mixed solvent containing an aliphatic saturated hydrocarbon, an aliphatic alcohol, and water.
[0052]
When three types of solvents, aliphatic saturated hydrocarbons, aliphatic alcohols, and water are mixed, a uniform and stable solvent system is usually not formed. Therefore, a mixed solvent obtained by mixing three kinds of solvents, that is, an aliphatic saturated hydrocarbon, an aliphatic alcohol, and water is not usually used as a solvent for a chemical reaction system. However, surprisingly, according to the present invention, it is possible to obtain a reaction system that is uniform and stable enough to perform a hydrogenation reaction, which is composed of a mixed solvent system containing these three types of solvents. That is, it has been found that lecithin hydrogenation can be carried out in a mixed solvent system containing the above three types of solvents. In the method of the present invention, lecithin is added to a system containing the above three solvents. For this reason, it is considered that lecithin acts as a surfactant, and as a result, lecithin, aliphatic saturated hydrocarbons, aliphatic alcohol, and water as a whole are uniform enough to perform the hydrogenation reaction. It is thought that a stable reaction system can be obtained.
[0053]
As a mixing ratio of the three kinds of solvents, the ratio of aliphatic saturated hydrocarbon to aliphatic alcohol to water is preferably a ratio of 100 to (10 to 600) to (5 to 600) in volume ratio. . A ratio of 100 to (20 to 300) to (10 to 300) is more preferable. More preferred is a ratio of 100 to (50 to 200) to (50 to 200).
[0054]
Here, as the aliphatic hydrocarbon, any aliphatic hydrocarbon solvent can be used. Typically, pentane, n-hexane, n-heptane, and the like can be given. Preferably, it is n-hexane. The aliphatic hydrocarbon may be a single aliphatic hydrocarbon or a mixture of a plurality of aliphatic hydrocarbons.
[0055]
Any aliphatic alcohol solvent can be used as the aliphatic alcohol. Typically, methanol, ethanol, isopropyl alcohol, etc. are mentioned, for example. The aliphatic alcohol may be a single aliphatic alcohol or a mixture of a plurality of aliphatic alcohols.
[0056]
Regarding the reaction temperature, it is said that it is more advantageous to heat in the normal catalytic hydrogenation reaction of fats and oils. However, in the lecithin hydrogenation reaction, on the contrary, it has been found that if the temperature is high, the catalyst may be deactivated quickly, which may hinder the achievement of a low iodine value. If the reaction temperature is too high, unhydrogenated lecithin tends to be denatured.
[0057]
Therefore, 0-80 degreeC is preferable, as for the reaction temperature in the method of this invention, 10-40 degreeC is more preferable, More preferably, it is 20-40 degreeC.
[0058]
The concentration of the reaction solution has a relatively large influence on the efficiency of hydrogenation. When the concentration is high, it is difficult to obtain a low iodine value. On the other hand, when the concentration is low, the manufacturing cost increases. Therefore, it is necessary to select an appropriate concentration in consideration of the iodine value to be obtained and the economy. Therefore, the concentration of egg yolk lecithin in the reaction solution is preferably 0.01 to 2 g / ml, more preferably 0.02 to 0.5 g / ml, still more preferably 0.05 to 0, based on the volume of the solvent. .2 g / ml.
[0059]
Although the reaction time depends on the catalyst concentration, it is preferably longer than the usual hydrogenation of unsaturated compounds. The reaction time is preferably 4 to 100 hours, more preferably 6 to 72 hours. More preferably, it is 30 to 72 hours, and particularly preferably 48 to 72 hours.
[0060]
Note that the hydrogen pressure does not significantly affect the final iodine value. Thus, any hydrogen pressure can be used. High-pressure conditions that are said to be appropriate in the usual catalytic hydrogenation of fats and oils are not necessarily advantageous. Therefore, in consideration of operability and economy, the hydrogen pressure is preferably 1 to 50 atm, and more preferably 1 to 20 atm.
[0061]
In one embodiment, the hydrogenated lecithin of the present invention comprises 0.01 to 5% by weight, preferably 0.02 to 3% by weight, based on natural lecithin in a hydrogen atmosphere, organic acid, and the total weight of the reaction solution. %, More preferably 0.05 to 2% by weight in a reaction solution containing hydrogenated catalyst in the presence of a hydrogenation catalyst.
[0062]
In one embodiment, after the hydrogenation reaction, the lecithin is purified by a method of precipitating from an organic solvent, preferably acetone, which does not substantially dissolve at room temperature. As a result, it is possible to remove a slight color and odor remaining in the lecithin after hydrogenation and to further suppress the iodine value.
[0063]
By the above production method, highly hydrogenated lecithin hydrogenated to an iodine value of 0.3 or less can be produced. In particular, in the case of egg yolk lecithin, highly hydrogenated lecithin hydrogenated to an iodine value of 0.3 or less can be produced while maintaining the composition of various phospholipids in natural egg yolk lecithin. Furthermore, highly hydrogenated lecithin hydrogenated to iodine value 0.1 or less, More preferably 0.05 or less can be manufactured by adjusting said conditions suitably and optimizing.
[0064]
(Cosmetic composition)
The cosmetic composition of the present invention contains the hydrogenated lecithin of the present invention.
[0065]
The cosmetic refers to any conventionally known cosmetic, and includes cosmetics.
[0066]
Here, the cosmetic is not particularly limited, but preferably skin care cosmetics such as lotion, emulsion, cream, foundation, eye shadow, lipstick, hair cosmetic, emollient cream, emollient lotion, foundation, cream rinse, cold Creams, vanishing creams, lotions, packs, shampoos, rinses, hair creams, hair lotions, hair treatments, blushers, pound cakes, and the like.
[0067]
The hydrogenated lecithin of the present invention can be used in a cosmetic composition as a humectant, an emulsifier, a microemulsion agent, a solubilizer, a liposome-forming material, or a pigment surface treatment agent.
[0068]
When hydrogenated lecithin is added as a moisturizer, emulsifier, microemulsion agent or solubilizer, the cosmetic composition usually contains an oily substance and optionally water. This cosmetic composition is usually in the form of a viscous or gel, oil-in-water emulsion or solubilized form.
[0069]
The content of hydrogenated lecithin in the cosmetic composition is preferably 0.001 to 10% by weight, more preferably 0.01 to 5% by weight, based on the entire product.
[0070]
For example, a viscous or gel cosmetic can be obtained by adding an oily substance to hydrogenated lecithin with stirring, and optionally adding a surfactant, pigment, dye, fragrance, antioxidant, etc. For example, it can be used as a cosmetic such as eye gel or cleansing gel. The blending amount of the oily substance relative to lecithin is preferably 10 times or less on a weight basis. When there are too many oily substances, it will become easy to isolate | separate an oily substance from a composition.
[0071]
Here, the oily substance used in the cosmetic is not particularly limited. For example, hydrocarbons (eg, squalane, liquid paraffin, petrolatum, solid paraffin, microcrystalline wax, ceresin, etc.), esters (eg, IPM, Glycerin triester, pentaerythritol tetraester, cholesteryl ester, etc.), fats and oils (for example, olive oil, almond oil, cacao oil, macadamia nut oil, avocado oil, hydrogenated palm oil, castor oil, sunflower oil, evening primrose oil, synthetic triglyceride, etc.) , Waxes (eg, beeswax, lanolin, carnauba wax, candelilla wax, jojoba oil), higher fatty acids (eg, stearic acid, oleic acid, isostearic acid, myristic acid, palmitic acid, behenic acid, etc.), higher alcohols Cetanol, stearyl alcohol, behenyl alcohol, hexadecyl alcohol, octyldodecyl alcohol, cholesterol, etc.), silicone-based materials (e.g., dimethyl polysiloxane, methylphenyl polysiloxane, cyclomethicone, etc.), sterols, etc. resins and the like.
[0072]
Specific examples include the following oily substances: liquid paraffin, isoparaffin, petrolatum, squalane, isopropyl myristate, octyldodecyl myristate, cetyl isooctylate (cetyl 2-ethylhexanoate), glyceryl triisooctylate. (Glyceryl tri-2-ethylhexanoate), glyceryl tricaprylate, neopentyl glycol diisooctylate (di-2-ethylhexanoate neopentyl glycol ester), diisostearyl malate, isononyl isononanoate (3, 5, 5 -Trimethylhexanoic acid 3,5,5-trimethylhexyl alcohol ester), cholesteryl 12-hydroxystearate, mono-hexaisostearic acid dipentaerythritol ester, o-, m- p-methoxycinnamate isooctyl, eucalyptus oil, soybean oil, cottonseed oil, sesame oil, rice germ oil, rice bran oil, safflower oil, sunflower oil, palm oil, olive oil, jojoba oil, macadamia nut oil, avocado oil, castor Oil, evening primrose oil, turtle oil, mink oil, orange luffy oil, lanolin, myristic acid, palmitic acid, stearic acid, oleic acid, 12-hydroxystearic acid, behenic acid, stearyl alcohol, oleyl alcohol, cetanol, lanolin alcohol, paraffin Wax, microcrystalline wax, ceresin wax, beeswax, carnauba wax, candelilla wax, shellac wax, hydrogenated soybean oil, rapeseed oil, glyceryl tristearate, rosin, cholesterol, phytosterol, dimethylpoly Rokisan, methylphenyl polysiloxane, etc. essential oil component of the flora and fauna origin.
[0073]
These oily substances may be used alone or in combination.
[0074]
As another example, an oily substance and water are mixed with hydrogenated lecithin under stirring, and a surfactant, pigment, dye, fragrance, antioxidant, preservative, moisturizing agent, or dispersing agent as necessary. Thus, an oil-in-water emulsified cosmetic can be obtained, and can be used as cosmetics such as creams, emulsions, and emulsified skin lotions. Here, the blending amount of water is preferably 0.1 to 100 times, more preferably 0.2 to 20 times on a weight basis with respect to hydrogenated lecithin.
[0075]
As yet another example, the above oil-in-water emulsified cosmetic is added with water under stirring, and optionally a surfactant, pigment, fragrance, antioxidant, preservative, moisturizer, or dispersant. When further added, the viscosity decreases, and for example, a solubilized aqueous cosmetic containing 50% by weight or more of water can be prepared. Such a water-based cosmetic can be used as, for example, a skin lotion or a cosmetic liquid. Here, the amount of water is preferably 1 to 1000 times, more preferably 10 to 100 times, based on weight with respect to hydrogenated lecithin.
[0076]
In this way, skin care cosmetics such as creams, emulsions, lotions, cosmetics, cleansing gels, moisture gels, packs, etc. that contain hydrogenated lecithin as a moisturizer, emulsifier, microemulsion, or solubilizer. Preparations such as cosmetics, emulsified foundations, emulsified eye shadows, and nail treatments can be prepared.
[0077]
A humectant refers to a cosmetic that moisturizes the skin.
[0078]
When hydrogenated lecithin is used as a humectant, the cosmetic composition can contain a conventionally known component as a humectant in a conventionally known blending amount. In this case, the hydrogenated lecithin is preferably contained in an amount of 0.01 to 20% by weight, more preferably 0.1 to 10% by weight.
[0079]
The emulsifier in the cosmetic composition refers to a component having an action of emulsifying the components in the cosmetic composition. The cosmetic composition in which the components are emulsified may be an oil-in-water emulsion or a water-in-oil emulsion.
[0080]
When hydrogenated lecithin is used to form an oil-in-water emulsion, the fat or fat-soluble drug is retained in water by the action of hydrogenated lecithin. When used as an oil-in-water emulsifier, for example, any conventionally known oil-in-water cosmetic component is used in a conventionally known blending amount. In this case, the hydrogenated lecithin is preferably contained in an amount of 0.01 to 20% by weight, more preferably 0.1 to 10% by weight.
[0081]
When hydrogenated lecithin is used to form a water-in-oil emulsion, hydrophilic components such as humectants other than lecithin and humectants other than lecithin are retained in the oil by the action of hydrogenated lecithin. Is done. When used as a water-in-oil emulsifier, for example, any conventionally known water-in-oil cosmetic component is used in a conventionally known blending amount. In this case, hydrogenated lecithin is preferably contained in an amount of 0.1 to 20% by weight, more preferably 0.2 to 10% by weight.
[0082]
Examples of humectants that can be used in the water-in-oil emulsion include polyhydric alcohols such as glycerin, 1,3-butylene glycol, and sorbitol, pyrrolidone carboxylate that is a main component of NMF (natural moisturizing factor), and Examples include lactate and sodium hyaluronate.
[0083]
Here, as the wetting agent that can be used in the water-in-oil emulsion, conventionally known wetting agents for water-in-oil emulsions can be used.
[0084]
The microemulsion agent refers to an emulsifier that microemulsifies cosmetics. Here, the microemulsion is a transparent or translucent one-liquid phase composed of an oil-water-amphiphile and is a thermodynamically stable system in which large swollen micelles are dispersed.
[0085]
Thus, hydrogenated lecithin can be preferably used mainly as an emulsifier for cosmetic compositions. However, it can also be used as an emulsifier for compositions other than cosmetic compositions.
[0086]
When hydrogenated lecithin is used as a microemulsion agent of a cosmetic composition, the cosmetic composition is composed of, for example, known components that are commonly used for microemulsified cosmetics in known amounts. Can be used.
[0087]
The solubilizer refers to a surfactant that solubilizes cosmetics and the like.
[0088]
(Other additives)
If necessary, sterols may be added to the cosmetic composition of the present invention. If sterol is added, the water vapor permeability of the composition can be suppressed.
[0089]
The sterol may be derived from an animal or a plant.
[0090]
A typical example of animal-derived sterols is cholesterol.
[0091]
Examples of plant-derived sterols include sitosterol, campesterol, stigmasterol, and brassicasterol, and these are collectively referred to as phytosterols (plant sterols).
[0092]
When cholesterol is added, the addition amount is preferably 1: 1 to 20: 1 as a ratio of hydrogenated lecithin to cholesterol, more preferably 2: 1 to 10: 1.
[0093]
When phytosterol is added, the amount added is preferably 1: 1 to 20: 1 as a ratio of hydrogenated lecithin to phytosterol, more preferably 2: 1 to 10: 1.
[0094]
You may mix | blend a ultraviolet absorber with the composition for cosmetics of this invention as needed.
[0095]
Examples of the ultraviolet absorber used include one or more of benzophenone, salicylic acid, PABA, dibenzoylmethane, cinnamate, and the like. The blending amount of the ultraviolet absorber is preferably 0.1 to 30% in the total amount of the cosmetic.
[0096]
Furthermore, the cosmetics of the present invention include components usually used in cosmetics, such as inorganic pigments, organic pigments, inorganic powders, organic powders, hydrocarbons, silicones, esters, triglycerides, lanolins, Waxes, waxes, animal and vegetable oils, alcohols, polyhydric alcohols, sugars, vitamins, amino acids, antioxidants, thickeners, pH adjusters, water, surfactants (eg, nonionic surfactants) Agent), oil agent, gelling agent, polymer, beauty ingredient, moisturizer, pigment, antioxidant, antiseptic, for example, perfume, pigment, antiseptic, antioxidant, anti-inflammatory agent, ultraviolet reflector, medicinal component (For example, hyaluronic acid, allantoin, vitamins, amino acids, and placenta extract), and flavors can be used as long as the effects of the present invention are not impaired.
[0097]
In the production, these additives are preferably added as a water phase component as a water-soluble component and as an oil phase component as a fat-soluble component.
[0098]
Solutions, emulsions, microemulsions, solubilized solutions, liposomes, and the like using the hydrogenated lecithin of the present invention are effective for cosmetics and can also be used for pharmaceuticals and functional foods.
[0099]
To explain a specific example of cosmetic use, for example, if it is a combination of packs,
Polyvinyl alcohol: 10-20%
Ethyl alcohol: 8-15%
Polyoxyethylene cetyl ether 20E. O. : 0.5-2%
Hydrogenated egg yolk lecithin: 0.2-1%
Fragrance: appropriate amount
Purified water: 100% remaining
Can be blended.
[0100]
More specifically, for example,
Polyvinyl alcohol: 15%
Ethyl alcohol: 10%
Polyoxyethylene cetyl ether 20E. O. : 1%
Hydrogenated egg yolk lecithin: 0.5%
Fragrance: appropriate amount
Purified water: 100% remaining
Can be blended.
[0101]
For example, in the case of hydrophilic ointment (neutral cream),
White petrolatum: 20-30%
Stearyl alcohol: 15-25%
Squalene: 1-5%
Cholesterol: 0.1-0.5%
Propylene glycol: 5-15%
Sodium lauryl sulfate: 1-2%
Hydrogenated lecithin: 0.2-3%
Preservative: 0.02-0.1%
Purified water: 100% remaining
Can be blended.
[0102]
More specifically, for example,
White petrolatum: 25%
Stearyl alcohol: 18%
Squalene: 3%
Cholesterol: 0.3%
Propylene glycol: 10%
Sodium lauryl sulfate: 1.5%
Hydrogenated lecithin: 2%
Preservative: 0.04%
Purified water: 100% remaining
Can be blended.
[0103]
For example, if it is a blend of a weak oily cream,
Stearic acid: 10-20%
2-octyldodecanol: 2-5%
Hydrogenated egg yolk lecithin: 0.5-2%
Cetanol: 0.2-1%
Potassium hydroxide: 0.2-1%
Sodium hydroxide: 0.1-0.5%
Propylene glycol: 4-15%
Fragrance: appropriate amount
Preservative: appropriate amount
Purified water: 100% remaining
Can be blended.
[0104]
More specifically, for example,
Stearic acid: 15%
2-octyldodecanol: 3.2%
Hydrogenated egg yolk lecithin: 1%
Cetanol: 0.5%
Potassium hydroxide: 0.5%
Sodium hydroxide: 0.2%
Propylene glycol: 8%
Fragrance: appropriate amount
Preservative: appropriate amount
Purified water: 100% remaining
Can be blended.
[0105]
For example, if it is a blend of emulsion,
Stearic acid: 1-5%
Lanolin: 1-5%
2-octyldodecanol: 10-15%
Sorbitan monostearate: 0.2-1%
Polyoxyethylene monostearate
Sorbitan 20E. O. : 1-4%
Hydrogenated egg yolk lecithin: 0.05-0.5%
Triethanolamine: 0.5-2%
Carboxyvinyl polymer: 0.1-0.5%
Propylene glycol: 2-10%
Fragrance: appropriate amount
Preservative: appropriate amount
Antioxidant: appropriate amount
Purified water: 100% remaining
Can be blended.
[0106]
More specifically, for example,
Stearic acid: 2%
Lanolin: 2%
2-octyldodecanol: 13%
Sorbitan monostearate: 0.5%
Polyoxyethylene monostearate
Sorbitan 20E. O. : 2%
Hydrogenated egg yolk lecithin: 0.1%
Triethanolamine: 1%
Carboxyvinyl polymer: 0.2%
Propylene glycol: 4%
Fragrance: appropriate amount
Preservative: appropriate amount
Antioxidant: appropriate amount
Purified water: 100% remaining
Can be blended.
[0107]
(Emulsion)
The hydrogenated lecithin of the present invention can be used to form various emulsions by stabilizing water-insoluble or poorly water-soluble substances in water. Such an emulsion can be widely used for various cosmetic applications described in the present specification.
[0108]
(Solubilized solution)
In the present specification, the solubilized solution refers to a solution obtained by dissolving a water-insoluble or slightly water-insoluble substance in water with hydrogenated lecithin to form a transparent solution. Such a solubilizing solution can be widely used for various cosmetic applications described in the present specification.
[0109]
(Liposome)
The liposome of the present invention is a closed vesicle composed of a lipid bilayer membrane containing the above-described hydrogenated lecithin of the present invention as a constituent component of the membrane.
[0110]
The liposome of the present invention can encapsulate a water-soluble active ingredient having a low affinity for the skin. As a result, a water-soluble active ingredient having a low affinity for the skin can be easily penetrated into the skin. Moreover, the release of the active ingredient can be controlled, and the effect can be maintained for a long time.
[0111]
Specific examples of the water-soluble active ingredient having low affinity for the skin include, for example, water-soluble polymers such as collagen, elastin, and hyaluronic acid, and moisturizers, whitening agents, and cell activation agents derived from plant extracts. Ingredients and the like.
[0112]
Liposomes may contain lipid-soluble or sparingly soluble drugs.
[0113]
In addition, sugars or charged substances may be encapsulated in the liposome.
[0114]
Liposomes are produced by a conventionally known method. For example, it can be prepared by dispersing a suspension of hydrogenated lecithin by vigorous stirring and then sonicating.
[0115]
The liposome of the present invention can retain a fat-soluble or sparingly soluble drug in the constituent bilayer membrane or on the membrane surface. The liposome of the present invention can also contain a water-soluble active ingredient or a humectant having a low absorbability and affinity for the skin.
[0116]
As a component of the liposome membrane of the present invention, cholesterol may be added in addition to the hydrogenated lecithin of the present invention.
[0117]
The liposome of the present invention can be preferably used mainly for a cosmetic composition having excellent temporal stability. However, it can also be used in compositions other than cosmetic compositions. For example, functional drugs and functional foods can be made into liposomes and used as medicines and functional foods.
[0118]
(Pigment)
The pigment of the present invention is surface-treated with the above-described hydrogenated lecithin of the present invention.
[0119]
In this specification, a pigment means a broadly defined pigment, and includes not only colored pigments but also so-called extender pigments having no coloring power and special pigments such as pearlescent pigments.
[0120]
Specific examples of the pigment include, for example, titanium oxide, zinc oxide, zirconium oxide, dial, yellow iron oxide, black iron oxide, ultramarine, bitumen, chromium oxide, chromium hydroxide, mango violet, and other inorganic color pigments, mica titanium, Pearlescent pigments such as bismuth oxychloride, talc, kaolin, mica (muscovite, sericite, etc.), magnesium carbonate, calcium carbonate, aluminum silicate, magnesium silicate, calcium silicate, clay, barium sulfate, barium carbonate, Examples thereof include inorganic extender pigments such as kieselguhr, other various metal powders, magnetic iron oxide, and ceramic powders. Organic pigments such as organic powders such as plastic powders and tar dyes can also be used. Further, a combination of an inorganic pigment and an organic pigment may be used.
The surface treatment of the pigment can be performed by a conventionally known method.
[0121]
For example, after the pigment is dispersed in a dispersion medium such as water or alcohol, hydrogenated lecithin is added and heated as necessary.
[0122]
Furthermore, in order to strengthen the binding of hydrogenated lecithin to the pigment, for example, after adding hydrogenated lecithin to the pigment dispersion, soluble salts such as aluminum, magnesium, calcium, zinc, zircon, titanium (for example, sulfuric acid) Aluminum, aluminum chloride, aluminum nitrate, potassium aluminum sulfate, magnesium chloride, magnesium sulfate, magnesium nitrate, magnesium sulfate, magnesium nitrate, potassium magnesium sulfate, calcium chloride, calcium nitrate, calcium acetate, zinc chloride, zinc nitrate, zinc acetate, sulfuric acid An aqueous solution (for example, 1 to 30% aqueous solution) of zirconium, zirconium chloride, titanium chloride, or the like) may be added dropwise so as to be, for example, 0.1 to 2 equivalents relative to hydrogenated lecithin. Thereby, hydrogenated lecithin turns into a water-insoluble metal salt, and adsorb | sucks to the pigment surface firmly. It is also possible to adsorb neutral fatty oil such as egg yolk oil at the same time.
[0123]
Thereafter, if the dispersion medium is removed by centrifugation or drying using heating or reduced pressure, a pigment surface-treated with hydrogenated lecithin can be obtained.
[0124]
Cosmetics using the surface-treated pigment as described above are smooth, have good elongation, have a moisturizing effect, have little skin irritation, and have high water repellency.
[0125]
The pigment of the present invention can be preferably used mainly for a cosmetic composition having excellent temporal stability. However, it can also be used in compositions other than cosmetic compositions, for example, compositions for electronic materials, or various chromatographic carriers.
[0126]
Examples and preparation examples are given below, but the present invention is not limited thereto.
[0127]
【Example】
In the following Examples and Preparation Examples, iodine value and lecithin content were measured as follows.
[0128]
Iodine number measurement method:
The iodine value was determined according to the cosmetic raw material standard general test method “45.
[0129]
As described above, lecithin has a liposome-forming ability, iodine is taken into the liposome, the reactivity is lowered, and the iodine-starch reaction is also inhibited. The measurement of iodine value is very inaccurate. Therefore, the present inventors adopted the following modified method in which the iodine value is measured after lecithin is hydrolyzed to lose the liposome-forming ability. Take 1 g of lecithin, add 30 mL of ethanol and 3 mL of 3N aqueous sodium hydroxide solution, and stir in warm water at 50 ° C. for 5 minutes. After cooling to room temperature, 4 mL acetic acid and 30 mL n-hexane are added. Add 25 ml of iodine monochloride test solution and shake. If the liquid does not become transparent, add more carbon tetrachloride, shield it from light, shield it from light, and shake it for 30 minutes at 20-30 ° C. Next, 20 ml of potassium iodide solution (1 → 10) and 100 ml of water are added and shaken, and the free iodine is titrated with a 0.01 mol / L sodium thiosulfate aqueous solution.

[0130]
(Preparation Example 1)
Purified lecithin derived from egg yolk (composition, PC: 79.8%; PE: 13.5%; LPC: 1.6%; SM: 2.0%; LPE: 0.8%) 20 g, n-hexane, ethanol And 10/2/4 (v / v / v) mixed solvent of water and 1 g of 5% platinum-activated carbon catalyst was added. This mixture was stirred for 52 hours at 30 to 35 ° C. in a hydrogen atmosphere of 1.5 to 2.0 atm. The catalyst was filtered off from the reaction mixture using celite.
[0131]
The filtrate was concentrated to about 140 mL under reduced pressure, 140 mL of warm acetone was added and stirred, and then cooled to −10 ° C. over about 5 hours. The precipitated hydrogenated lecithin was collected by filtration and dried under reduced pressure. Yield was 18.0 g.
[0132]
If necessary, after dissolving in ethanol by heating, it is concentrated and dried to replace the residual solvent with ethanol. The hydrogenated lecithin thus obtained was 0.03 when the iodine value was precisely measured by the above method. The lecithin composition was as follows: PC: 79.0%; PE: 12.8%; LPC: 3.1%; SM: 1.7%; LPE: 1.8%.
[0133]
(Preparation Example 2)
Purified lecithin derived from egg yolk (composition, PC: 79.8%; PE: 13.5%; LPC: 1.6%; SM: 2.0%; LPE: 0.8%) 20 g, n-hexane, ethanol , And 10/2/4 (v / v / v) mixed solvent of water, and 0.4 g of citric acid and 2 g of 5% palladium-activated carbon catalyst were added. This mixture was stirred for 60 hours at 30 to 35 ° C. in a hydrogen atmosphere of 1.5 to 2.0 atm. To the reaction mixture, 0.8% of 14% aqueous ammonia was added to neutralize citric acid to precipitate as an ammonium salt, and the iodine value was measured in the same manner as in Preparation Example 1 below. As a result, hydrogenated egg yolk with iodine value of 0.01, lecithin composition: PC: 79.5%; PE: 12.5%; LPC: 3.2%; SM: 1.5%; LPE: 1.9% 17.8 g of lecithin was obtained.
[0134]
(Preparation Example 3)
Hydrogenated egg yolk lecithin having an iodine value of 0.18 was obtained in the same manner as in Preparation Example 1 except that egg yolk-derived purified lecithin having a PC content of 60.5% was used as a raw material and the reaction time was 55 hours.
[0135]
(Preparation Example 4)
Hydrogenated egg yolk lecithin having an iodine value of 0.25 was obtained in the same manner as in Preparation Example 1 except that egg yolk-derived purified lecithin having a PC content of 31.3% was used as a raw material and the reaction time was 60 hours.
[0136]
(Preparation Example 5)
Hydrogenated soybean lecithin having an iodine value of 0.09 was obtained in the same manner as in Preparation Example 1 except that soybean lecithin having a PC content of 85.6% was used as the raw material lecithin.
[0137]
(Preparation Example 6)
Hydrogenated soybean lecithin having an iodine value of 0.21 was obtained in the same manner as in Preparation Example 1, except that soybean lecithin having a PC content of 70.4% was used as the raw material lecithin.
[0138]
(Preparation Example 7)
Hydrogenated egg yolk lecithin having an iodine value of 0.16 was obtained in the same manner as in Preparation Example 1 except that soybean lecithin having a PC content of 30.6% was used as the raw material lecithin.
[0139]
(Preparation Comparative Example 1)
Hydrogenated egg yolk lecithin having an iodine value of 0.50 was obtained in the same manner as in Preparation Example 1 except that the solvent used in the hydrogenation reaction was a solvent consisting only of n-hexane.
[0140]
(Preparation Comparative Example 2)
A hydrogenated egg yolk lecithin having an iodine value of 1.85 was prepared in the same manner as in Preparation Example 1 except that the solvent used in the hydrogenation reaction was a solvent consisting only of n-hexane and the reaction time was 24 hours. Obtained.
[0141]
(Preparation Comparative Example 3)
A hydrogenated soybean lecithin having an iodine value of 0.62 was prepared in the same manner as in Preparation Example 6 except that the solvent used in the hydrogenation reaction was a solvent consisting only of n-hexane and the reaction time was 60 hours. Obtained.
[0142]
(Preparation Comparative Example 4)
A hydrogenated soybean lecithin having an iodine value of 2.31 was prepared in the same manner as in Preparation Example 6 except that the solvent used in the hydrogenation reaction was a solvent consisting only of n-hexane and the reaction time was 24 hours. Obtained.
[0143]
Example 1
Hydrogenated egg yolk lecithin (iodine value 0.03) obtained in Preparation Example 1, hydrogenated egg yolk lecithin obtained in Preparation Example 4 (iodine value 0.25), and hydrogenated egg yolk lecithin prepared in Preparation Comparative Example 1 ( Iodine number 0.50) and hydrogenated egg yolk lecithin (iodine number 1.85) prepared in Preparation Comparative Example 2 were sealed in a glass bottle and compared in an accelerated test at 50 ° C.
[0144]
The above-mentioned various hydrogenated lecithin powders were sealed in a glass bottle and allowed to stand at 50 ° C., and changes in powder color and odor were observed. The results obtained are shown in Table 1 below. In the table, “OK” indicates that no bad odor was generated.
[0145]
[Table 1]

[0146]
(Example 2)
The hydrogenated lecithin powders obtained in Preparation Examples 5 and 6 and Preparation Comparative Examples 3 and 4 were sealed in a glass bottle and allowed to stand at 50 ° C., and changes in powder color and odor were observed. The results obtained are shown in Table 2 below. In the table, “OK” indicates that no bad odor was generated.
[0147]
[Table 2]

[0148]
(Example 3)
The hydrogenated lecithin powders obtained in Preparation Example 5 and Preparation Comparative Examples 3 and 4 were blended according to a conventional method to obtain neutral creams (hydrophilic ointments). The resulting neutral cream formulation is as follows:
25% white petrolatum
Stearyl alcohol 18%
Squalene 3%
Cholesterol 0.3%
Propylene glycol 10%
Sodium lauryl sulfate 1.5%
Hydrogenated lecithin 2%
Preservative 0.04%
(The balance of 100% is purified water).
[0149]
The obtained neutral cream was sealed in a container and allowed to stand at 50 ° C., and changes in powder color and odor were observed. The results obtained are shown in Table 3 below. In the table, “OK” indicates that no bad odor was generated.
[0150]
[Table 3]

[0151]
【Effect of the invention】
According to the present invention, there are provided hydrogenated lecithin useful as a cosmetic compounding material and other additives, which has an extremely low iodine value, can be stored for a long period of time, and is extremely stable, and a method for producing the same.

Claims (11)

Hydrogenated lecithin obtained by hydrogenating natural plant lecithin or animal lecithin, measured by a method of measuring iodine value after hydrolyzing hydrogenated lecithin to lose its ability to form liposomes Hydrogenated lecithin having an iodine value of 0.3 or less. Hydrogenated lecithin obtained by hydrogenating natural plant lecithin or animal lecithin, measured by a method of measuring iodine value after hydrolyzing hydrogenated lecithin to lose its ability to form liposomes The hydrogenated lecithin according to claim 1, which has an iodine value of 0.1 or less. The hydrogenated lecithin according to any one of claims 1 to 2, obtained by hydrogenating soybean lecithin or egg yolk lecithin. The iodine value measured by the method of measuring the iodine value after hydrolyzing hydrogenated lecithin and losing the ability to form liposomes is 0.3 or less, and the composition of phospholipids in natural lecithin is maintained. Hydrogenated egg yolk lecithin derived from natural egg yolk. The hydrogenated egg yolk lecithin according to claim 4 , wherein the iodine value measured by a method of measuring the iodine value after hydrolyzing the hydrogenated lecithin and losing the ability to form liposomes is 0.1 or less. Hydrogenated lecithin obtained by hydrogenating natural plant lecithin or animal lecithin, measured by a method of measuring iodine value after hydrolyzing hydrogenated lecithin to lose its ability to form liposomes A cosmetic composition comprising hydrogenated lecithin having an iodine value of 0.3 or less. The composition of claim 6 , wherein the hydrogenated lecithin is hydrogenated egg yolk lecithin. A method for producing hydrogenated lecithin, comprising a reaction at 10 to 40 ° C. in a reaction solution containing a mixed solvent of an aliphatic saturated hydrocarbon, an aliphatic alcohol and water in a hydrogen atmosphere in the presence of a hydrogenation catalyst. Hydrogenating natural lecithin at a temperature to bring the iodine number to 0.3 or less, wherein
The mixing ratio of the mixed solvent is 100: (20-300) :( 10-300) as a volume ratio of aliphatic saturated hydrocarbon: aliphatic alcohol: water.
And
The aliphatic saturated hydrocarbon is n-hexane or n-heptane, and the aliphatic alcohol is ethanol, isopropyl alcohol or methanol;
Method. 9. The method according to claim 8 , wherein the aliphatic saturated hydrocarbon is n-hexane and the aliphatic alcohol is ethanol. The mixing ratio of the mixed solvent is 100: 20: 40 as an aliphatic saturated hydrocarbon: aliphatic alcohol: water volume ratio.
10. The method according to claim 8 or 9 , wherein 9. The method of claim 8 , further comprising the step of precipitating hydrogenated lecithin from acetone.