JP2000247987A - Highly hydrogenated lecithin - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject lecithin which can be preserved for a long term, is extremely stable and useful as a cosmetic compounding material or another additive by bringing the iodine number of a hydrogenated lecithin to a specific level or lower. SOLUTION: This lecithin is obtained by hydrogenating natural lecithin (preferably natural yolk lecithin) preferably at 20-40 deg.C for 48-72 h in a reaction solution containing a mixed solvent comprising an aliphatic saturated hydrocarbon (preferably n-hexane), an aliphatic alcohol (preferably ethanol) and water at a volume ratio of preferably 100:(20-30):(10-300) in the presence of a hydrogenation catalyst such as platinum-activated carbon catalyst in a hydrogen atmosphere to bring the iodine number of the final product to <=0.3, preferably <=0.1. This lecithin is useful as a compounding ingredient of medicines, functional foods or the like.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to highly hydrogenated lecithin and a method for producing the same.

[0002]

2. Description of the Related Art Lecithin is widely used in a wide variety of 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 good touch, but it has disadvantages such as coloring and giving off odor during long-term storage. Have. The disadvantage of this storage stability is that unsaturated fatty acids are present in the fatty acids constituting the phospholipid, and the unsaturated double bonds are easily oxidized during storage.

As a method for overcoming this drawback, a method has been known in which unsaturated double bonds in lecithin are catalytically hydrogenated in the presence of hydrogen and a hydrogenation catalyst to obtain hydrogenated lecithin. ing.

At this time, the degree of hydrogenation can be known from the extent to which the iodine value, which is an indicator of the presence of an unsaturated double bond, decreases. The iodine value is closely related to the stability of hydrogenated lecithin during long-term storage, and hydrogenated lecithin having an iodine value as close to zero as possible has a very 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, the iodine value is 1
It is not easy to highly hydrogenate to less than, especially less than 0.3, and even near zero.

[0006] For example, in the prior art of hydrogenating egg yolk lecithin, various phospholipids present in lecithin are isolated from each other, and, for example, 95 of phosphatidylcholine (hereinafter, also referred to as “PC”) which is present in the largest amount is isolated. %
Alternatively, there is known an example in which the catalyst is further purified and then subjected to a catalytic hydrogenation reaction to hydrogenate to an iodine value of less than 1.

However, when various types of phospholipids present in egg yolk lecithin are not separated, that is, when lecithin having a natural phospholipid composition ratio is subjected to a catalytic hydrogenation reaction, depending on the reaction conditions, The iodine value can only be reduced to 2-3 under normal conditions, and has been reduced to only about 1 at best in the past.

[0008] Similarly, in the case of soybean lecithin, there is a soybean lecithin with an iodine value of 1 to 0.5, but it has been difficult to reduce the iodine value to less.

For this reason, conventionally, an iodine value of 1
Lecithin less than or less than 0.5 with an iodine value was difficult to obtain.

[0010] In particular, there has not yet been reported any technology capable of highly hydrogenating an iodine value of 0.3 or less, and the existence of such highly hydrogenated lecithin was not known. Furthermore, in the case of egg yolk lecithin, there has not yet been reported any technology capable of highly hydrogenating an iodine value to 0.3 or less while maintaining the composition of various phospholipids of natural lecithin.
And the existence of such highly hydrogenated egg yolk lecithin was not known.

[0011]

Accordingly, an object of the present invention is to provide a lecithin which can be stored for a long period of time, and a method for producing the same. Specifically, an object is to provide a hydrogenated lecithin having an iodine value of 0.3 or less, preferably 0.1 or less. It is still another object of the present invention to provide a compounding agent using such a lecithin, and to provide cosmetics, pharmaceuticals, functional foods, and the like using the compounding agent.

[0012]

Means for Solving the Problems The present inventors have conducted 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 invention described below has been completed.

[0013] The hydrogenated lecithin of the present invention is a hydrogenated lecithin having an iodine value of 0.3 or less.

In a preferred embodiment, the iodine value is 0.1
It is as follows.

Further, according to the present invention, the iodine value is 0.3
A hydrogenated egg yolk lecithin derived from natural egg yolk is provided, wherein the composition is as follows, and the composition of phospholipids in the natural lecithin is maintained.

In a preferred embodiment, the hydrogenated egg yolk lecithin has an iodine value of 0.1 or less.

The cosmetic composition of the present invention contains hydrogenated lecithin having an iodine value of 0.3 or less.

In one embodiment, the hydrogenated lecithin is 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 soy lecithin.

The process of the present invention is a process for producing hydrogenated lecithin, which comprises a reaction mixture 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. In which natural lecithin is hydrogenated to reduce the iodine value to 0.3 or less. Preferably, the reaction is performed in a reaction solution containing 0.01 to 5% by weight of an organic acid.

In one embodiment, the aliphatic saturated hydrocarbon is n-hexane and the aliphatic alcohol is ethanol.

In a preferred embodiment, the mixing ratio of the mixed solvent is 100: (20-300) :( 10-300) as a volume ratio of aliphatic saturated hydrocarbon: aliphatic alcohol: water.

In one embodiment of the production method of the present invention,
The method further includes a step of precipitating the hydrogenated lecithin from acetone.

[0025] In another aspect, there is provided a solution, emulsion or lysate comprising the hydrogenated lecithin of the present invention.

In another aspect, there is provided a liposome containing the hydrogenated lecithin of the present invention.

In another aspect, there is provided a pigment surface-treated with the hydrogenated lecithin of the present invention.

[0028]

BEST MODE FOR CARRYING OUT THE INVENTION (Hydrogenated lecithin) Lecithin is a general term for various phospholipids. In natural lecithin, phosphatidylcholine (PC), phosphatidylethanolamine (PE), lysophosphatidylcholine (L
PC), lysophosphatidylethanolamine (LP
E), sphingomyelin (SM), phosphatidic acid and the like are present in a predetermined ratio.

Lecithin includes both vegetable lecithin and animal lecithin.

Examples of vegetable lecithin include soybean lecithin, rapeseed lecithin, sunflower lecithin, safflower lecithin, cottonseed lecithin, corn lecithin, amani lecithin, sesame lecithin, olive lecithin, rice lecithin, kiri lecithin, grape precitin, Avocadolecithin, palm lecithin, palm lecithin and the like. These are each obtained from the plant seed. Soy lecithin is preferred.

Vegetable lecithin is usually separated as gum when extracting and purifying oils and fats from plant seeds.

Soy lecithin is lecithin obtained from soybeans, and is a mixture of the above-mentioned phospholipids, and although there are some fluctuations due to environmental factors and the like, phosphatidylcholine (PC) is generally 24 to 32%, There is 20-28% phosphatidylethanolamine (PE), 12-20% phosphatidylinositol (PI), and 3-15% phosphatidic acid (PA).

Any known soybean lecithin can be used. Soy lecithin may be used as it is in its natural composition. However, if necessary, a phosphatidylcholine (PC) -treated one may be used.

Examples of animal lecithin include egg yolk lecithin and lecithin extracted from fish and shellfish. Lecithins other than egg yolk lecithin can be used, but egg yolk lecithin is preferred.

"Egg yolk lecithin" is lecithin derived from egg yolk and is a mixture of the above phospholipids, and although there are some fluctuations due to chicken feed and other environmental factors, phosphatidylcholine (PC) is generally used. 75-85%, 10-20% phosphatidylethanolamine (PE), and
Lysophosphatidylcholine (LPC), lysophosphatidylethanolamine (LPE), and sphingomyelin (SM) are each present at a few percent.

Any known natural egg yolk lecithin can be used. For example, it can be separated and purified from natural egg yolk.

Natural egg yolk lecithin is lecithin extracted from natural egg yolk and is not hydrogenated.
Lecithin that has not undergone any of the other artificial manipulations that can vary the amount of unsaturated double bonds.

In the yolk lecithin, "the phospholipid composition is maintained" means that the phospholipid composition has not substantially changed except that the unsaturated double bond has been hydrogenated. The maximum value of the variation of the composition ratio of each component is preferably 10% or less, more preferably 5% or less.

The iodine value is a value obtained by converting the amount of halogen absorbed when a halogen acts on lecithin into iodine and expressing the amount in grams per 100 g of the sample. As a specific method for measuring the iodine value, a conventionally known method can be used. However, in the case of lecithin having an iodine value of 1 or less, iodine is taken into the liposome formed by lecithin, whereby the reactivity decreases, and the iodine-starch reaction is inhibited, so that the measurement accuracy of the iodine value decreases. Therefore, in such a case, the iodine value is measured with good precision by previously hydrolyzing lecithin to lose the liposome-forming ability of lecithin and then measuring the iodine value.
Therefore, the “iodine value” in the present invention refers to a value measured after hydrolyzing lecithin.

In the case of natural non-hydrogenated lecithin,
Its iodine value is usually from 60 to 90. The iodine value of hydrogenated lecithin conventionally obtained is usually 2 to 10. In contrast, the highly hydrogenated lecithin of the present invention
Has an iodine value of 0.3 or less, preferably 0.1 or less;
Thereby, the long-term storage stability is remarkably improved, and the usefulness as a cosmetic compounding material is particularly enhanced.

(Method for Producing Hydrogenated Lecithin) Next, the method for producing hydrogenated lecithin of the present invention will be described.

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.

The hydrogen atmosphere is usually formed of high-purity hydrogen gas, but any other gas can be used as long as the catalytic hydrogenation reaction is not hindered.

The organic acid added to the reaction solution as a weakly acidic substance is preferably an organic carboxylic acid, more preferably an organic polycarboxylic acid, for example, citric acid, malic acid,
Tartaric acid and the like can be suitably used.

By slightly adding a slightly acidic substance and slightly tilting the reaction solution to the acidic side, deactivation of the catalyst can be suppressed,
It is believed that low iodine values are achieved as a result.

As the catalyst used in the hydrogenation reaction of the present invention, any hydrogenation catalyst conventionally used for hydrogenating unsaturated fats and oils can be used. Specifically, a palladium-containing catalyst, a platinum-containing catalyst, for example, a palladium-activated carbon catalyst, a platinum-activated carbon catalyst, or the like can be used. Most preferred is a platinum / activated carbon catalyst.

The larger the amount of the catalyst is, the more advantageous it is. However, it is necessary to determine the amount of the catalyst in consideration of economy. Usually, the amount of the active metal is 0.1 to 0.1 parts by weight per 100 parts by weight of lecithin.
It is preferably 20 parts by weight, more preferably 0.2 to 15 parts by weight, and still more preferably 0.2 to 5 parts by weight. If the amount of the catalyst is too large, it becomes easy to remove the catalyst after the reaction. However, in order for the reaction to proceed efficiently,
Preferably, the amount of catalyst is high. For example, when it is desired to promote the reaction particularly efficiently, the active metal 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.

Usually, in the catalytic hydrogenation reaction, in addition to the type and amount of the catalyst, the type of the reaction solvent, the concentration and temperature of the reaction solution, the reaction time, the stirring efficiency, the hydrogen pressure, etc., affect the efficiency of the hydrogenation. Affect.

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 particular influence.

In the method of the present invention, selection of a reaction solvent is particularly important. Conventionally, the hydrogenation reaction of lecithin is n-
It is carried out in an aliphatic saturated hydrocarbon solvent such as hexane and n-heptane. In addition, an aliphatic alcohol such as methanol, ethanol, or isopropyl alcohol may be 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.

According to the method of the present invention, hydrogenated lecithin having an extremely 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.

Aliphatic saturated hydrocarbons, aliphatic alcohols,
When three types of solvents are mixed, water and water do not usually form a uniform and stable solvent system. Therefore, usually, a mixed solvent in which three kinds of solvents are mixed with an aliphatic saturated hydrocarbon, an aliphatic alcohol, and water is not used as a solvent for a chemical reaction system. However, it is surprising that, according to the present invention, a homogeneous and stable reaction system consisting of a mixed solvent system containing these three types of solvents can be obtained to a degree sufficient to carry out the hydrogenation reaction. That is, it has been found that lecithin can be hydrogenated 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, lecithin is considered to act as a surfactant, and as a result, lecithin, aliphatic saturated hydrocarbons, aliphatic alcohols, and water as a whole are sufficiently uniform and sufficient to carry out the hydrogenation reaction. It is considered that a stable reaction system is obtained.

The mixing ratio of the above three solvents is such that the ratio of aliphatic saturated hydrocarbon to aliphatic alcohol to water is 100: (10-600) :( 5-600) by volume. Is preferred. 100 pairs (20-300)
More preferably, the ratio is in the range of (10 to 300).
More preferably, the ratio is 100: (50-200) :( 50-200).

Here, as the aliphatic hydrocarbon, any aliphatic hydrocarbon solvent can be used. Typically, pentane, n-hexane, n-heptane and the like can be mentioned. Preferably, it is n-hexane. The aliphatic hydrocarbon may be a single aliphatic hydrocarbon or a mixture of a plurality of aliphatic hydrocarbons.

As the aliphatic alcohol, any aliphatic alcohol solvent can be used. Typically, for example, methanol, ethanol, isopropyl alcohol and the like can be mentioned. The aliphatic alcohol may be a single aliphatic alcohol or a mixture of a plurality of aliphatic alcohols.

Regarding the reaction temperature, it is said that heating is more advantageous in the usual catalytic hydrogenation of fats and oils. However, it has been found that in the lecithin hydrogenation reaction, rather conversely, higher temperatures can cause the catalyst to deactivate faster and prevent low iodine values from being achieved. If the reaction temperature is too high, unhydrogenated lecithin tends to be denatured.

Therefore, the reaction temperature in the method of the present invention is preferably from 0 to 80 ° C, more preferably from 10 to 40 ° C, and still more preferably from 20 to 40 ° C.

The concentration of the reaction solution has a relatively large effect 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 production cost increases. Therefore, it is necessary to select an appropriate concentration in consideration of the iodine value to be obtained and economy. Therefore,
The concentration of egg yolk lecithin in the reaction solution is preferably 0.01 to 2 g / ml, and preferably 0.02 to 0.
5 g / ml is more preferable, and still more preferably, 0.0 g / ml.
5 to 0.2 g / ml.

Although the reaction time depends on the catalyst concentration, it is preferable to make the reaction time longer as compared with the usual hydrogenation of unsaturated compounds. The reaction time is preferably 4 to 100 hours, and 6 to
72 hours is more preferred. More preferably, 30 to 7
It is 2 hours, particularly preferably 48 to 72 hours.

The hydrogen pressure does not significantly affect the final iodine value. Thus, any hydrogen pressure can be used. High pressure conditions, which are said to be appropriate in ordinary catalytic hydrogenation of fats and oils, are not always advantageous. Therefore,
In consideration of operability and economy, the hydrogen pressure is 1 to 50.
Atmospheric pressure is preferred, and 1 to 20 atm is more preferred.

In one embodiment, the hydrogenated lecithin of the present invention is obtained by adding natural lecithin in a hydrogen atmosphere to an organic acid in an amount of 0.01 to 5% by weight, preferably 0.02% by weight, based on the total weight of the reaction solution. ~ 3% by weight, more preferably 0.05 ~
It can be produced by hydrogenation in a reaction solution containing 2% by weight in the presence of a hydrogenation catalyst.

In one embodiment, after the hydrogenation reaction, the lecithin is purified by a method of precipitating from an organic solvent having a property of not substantially dissolving at room temperature, preferably acetone. As a result, it is possible to remove the color and odor that slightly remain in lecithin after hydrogenation, and to further reduce the iodine value.

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 that has been 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. Further, by appropriately adjusting and adjusting the above conditions, an iodine value of 0.1 is obtained.
Highly hydrogenated lecithin hydrogenated to 1 or less, more preferably 0.05 or less can be produced.

(Cosmetic Composition) The cosmetic composition of the present invention contains the hydrogenated lecithin of the present invention.

[0065] Cosmetics refer to any conventionally known cosmetics, including cosmetics.

The cosmetic is not particularly limited, but is preferably a skin care cosmetic such as a lotion, an emulsion or a cream, a foundation, an eye shadow, a lipstick, a hair cosmetic, an emollient cream, an emollient lotion,
Foundations, cream rinses, cold creams, burnishing creams, lotions, packs, shampoos, rinses, hair creams, hair lotions, hair treatments, blushers, pound cakes, and the like.

The hydrogenated lecithin of the present invention is used in a cosmetic composition in a humectant, an emulsifier, a microemulsion,
It can be used as a solubilizing agent, a liposome-forming material or a surface treating agent for pigments.

When hydrogenated lecithin is added as a humectant, emulsifier, microemulsion or solubilizer, the cosmetic composition usually contains an oily substance and, if necessary, water. This cosmetic composition is usually in the form of a viscous or gel-like, oil-in-water emulsion or solubilized form.

The content of hydrogenated lecithin in the cosmetic composition is preferably from 0.001 to
The content is 10% by weight, more preferably 0.01 to 5% by weight.

For example, a viscous or gel-like cosmetic can be obtained by mixing an oily substance and, if desired, a surfactant, a pigment, a dye, a fragrance, an antioxidant, etc., with hydrogenated lecithin under stirring. And can be used, for example, as a cosmetic such as an eye gel or a cleansing gel. The amount of the oily substance to lecithin is preferably 10 times or less on a weight basis. If the amount of the oily substance is too large, the oily substance is easily separated from the composition.

Here, the oily substance used in the cosmetic is not particularly limited, and examples thereof include hydrocarbons (for example, squalane, liquid paraffin, vaseline, solid paraffin, microcrystalline wax, ceresin, etc.), esters (for example, , IPM, glycerin triester, pentaerythritol tetraester, cholesteryl ester, etc.), fats and oils (for example, olive oil, almond oil,
Cocoa oil, macadamia nut oil, avocado oil, hardened palm oil, castor oil, sunflower oil, evening primrose oil, synthetic triglyceride, etc., waxes (eg, beeswax, lanolin, carnauba wax, candelilla wax, jojoba oil, etc.), higher fatty acids ( For example, 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 substances (eg, dimethylpolysiloxane, methylphenylpolysiloxane, cyclomethicone, etc.), sterols, Resins.

Specific examples include the following oily substances: liquid paraffin, isoparaffin, petrolatum, squalane, isopropyl myristate, octyldodecyl myristate, cetyl isooctylate (cetyl 2-ethylhexanoate), triisobutylene Glyceryl octylate (glyceryl tri-2-ethylhexanoate), glyceryl tricaprylate, neopentyl glycol diisooctylate (neopentyl glycol di-2-ethylhexanoate), diisostearyl malate, isononyl isononanoate (3, 5,5-trimethylhexanoic acid 3,5,5-trimethylhexyl alcohol ester), cholesteryl 12-hydroxystearate, dipentaerythritol mono- or hexaisostearate, o , M- or p- methoxy cinnamic acid 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, macadamian nut oil, avocado oil, castor oil, evening primrose oil, turtle oil, mink oil, orange roughy 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, soybean hardened oil, rapeseed hardened oil, tristearin Glyceryl acid, rosin, cholesterol, phytosterol, dimethylpolysiloxane, methylphenylpolysiloxane, essential oil components of animal and plant origin.

These oily substances may be used alone,
Alternatively, they may be used as a mixture.

As another example, an oily substance and water are added to hydrogenated lecithin under stirring, and if necessary, a surfactant, a pigment, a dye, a fragrance, an antioxidant, a preservative, a humectant,
Or by blending a dispersant or the like, an oil-in-water emulsified cosmetic can be obtained, for example, a cream, an emulsion,
It can be used as a cosmetic such as emulsified lotion. Here, the mixing amount of water is 0.1% by weight with respect to the hydrogenated lecithin.
It is preferably from 1 to 100 times, more preferably from 0.2 to 20 times.

As still another example, the above oil-in-water emulsified cosmetic is mixed with water under stirring and, if necessary, a surfactant, a dye, a fragrance, an antioxidant, a preservative, a humectant, or a dispersion. When an agent or the like is further added, the viscosity decreases, and for example, a solubilized aqueous cosmetic containing 50% by weight or more of water can be prepared. Such an aqueous cosmetic can be used, for example, as a lotion or a serum. Here, the blending amount of water is 1-fold on a weight basis with respect to hydrogenated lecithin.
It is preferably 1000 times, more preferably 10 times.
Times to 100 times.

As described above, hydrogenated lecithin is used as a humectant,
Emulsifiers, microemulsions, or cosmetics such as creams, emulsions, lotions, essences, cleansing gels, moisturizing gels, skin care cosmetics such as packs, emulsified foundations formulated as solubilizers,
Makeup cosmetics such as emulsified eye shadows and nail treatments can be prepared.

The moisturizer refers to a cosmetic for moisturizing the skin.

When hydrogenated lecithin is used as a humectant, the cosmetic composition may contain a conventionally known component as a humectant in a conventionally known amount. in this case,
The content of hydrogenated lecithin is preferably 0.01 to 20% by weight, more preferably 0.1 to 10% by weight.

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.

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 type emulsifier, for example, any conventionally known oil-in-water type cosmetic component is used in a conventionally known compounding amount. In this case, the hydrogenated lecithin is preferably 0.01 to 20% by weight,
More preferably, the content is 0.1 to 10% by weight.

When hydrogenated lecithin is used to form a water-in-oil emulsion, a hydrophilic component such as a humectant other than lecithin and a humectant other than lecithin is added to the oil by the action of hydrogenated lecithin. Will be kept inside.
When used as a water-in-oil type emulsifier, for example, any conventionally known water-in-oil type cosmetic ingredient is used in a conventionally known amount. In this case, the content of hydrogenated lecithin is preferably 0.1 to 20% by weight, more preferably 0.2 to 10% by weight.

Examples of the humectant that can be used in the water-in-oil emulsion include polyhydric alcohols such as glycerin, 1,3-butylene glycol and sorbitol;
Examples include pyrrolidone carboxylate and lactate, which are main components of NMF (natural moisturizing factor), and sodium hyaluronate.

Here, as the wetting agent that can be used for the water-in-oil emulsion, a conventionally known wetting agent for a water-in-oil emulsion can be used.

The microemulsion means an emulsifier for microemulsifying a cosmetic. Here, the microemulsion is a transparent or translucent one-liquid phase composed of an oil-water-amphiphile, which is thermodynamically stable and in which large swollen micelles are dispersed.

As described above, 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.

When hydrogenated lecithin is used as a microemulsion in a cosmetic composition, the cosmetic composition may include, for example, any known ingredients commonly used in microemulsified cosmetics. Can be used.

[0087] The solubilizing agent refers to a surfactant that solubilizes cosmetics and the like.

(Other Additives) A sterol may be added to the cosmetic composition of the present invention, if necessary.
Addition of a sterol can suppress the water vapor permeability of the composition.

The sterol may be of animal origin or plant origin.

[0099] Representative sterols derived from animals include cholesterol.

Examples of plant-derived sterols include:
Examples include sitosterol, campesterol, stigmasterol, and brassicasterol, which are collectively referred to as phytosterols (plant sterols).

When cholesterol is added, the amount thereof is preferably 1: 1 to 20: 1, more preferably 2: 1 to 10: 1 as a ratio of hydrogenated lecithin to cholesterol.

When phytosterol is added, the amount added is preferably from 1: 1 to 20: 1, more preferably from 2: 1 to 10: 1, as a ratio of hydrogenated lecithin to phytosterol.

The cosmetic composition of the present invention may optionally contain an ultraviolet absorbent.

The UV absorber used may be one or more of benzophenone, salicylic acid, PABA, dibenzoylmethane, cinnamate and the like. The compounding amount of the ultraviolet absorber is 0.1% of the total amount of the cosmetic.
1 to 30% is desirable.

Further, 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, p
H adjuster, water, surfactant (for example, nonionic surfactant), oil, gelling agent, polymer, cosmetic ingredient, humectant,
Pigments, antioxidants, preservatives, such as fragrances, pigments, preservatives, antioxidants, anti-inflammatory agents, UV reflectors, medicinal ingredients (eg, hyaluronic acid, allantoin, vitamins, amino acids, and placenta extract); And a fragrance | flavor etc. can be used in the range which does not impair the effect of this invention.

In the production, these additives are preferably prepared such that the water-soluble component is an aqueous phase component and the fat-soluble component is
It is added as an oil phase component.

A solution using the hydrogenated lecithin of the present invention,
Emulsions, microemulsions, solubilizing solutions, liposomes and the like are effective for cosmetics and can also be used for pharmaceuticals and functional foods.

A specific example of the cosmetic use will be described. For example, in the case of a pack formulation, polyvinyl alcohol: 10 to 20% ethyl alcohol: 8 to 15% polyoxyethylene cetyl ether 20E. O. : 0.5 to 2% hydrogenated egg yolk lecithin: 0.2 to 1% Fragrance: appropriate amount Purified water: 100% of the rest can be blended.

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 combined.

For example, in the case of a hydrophilic ointment (neutral cream), white petrolatum: 20 to 30% stearyl alcohol: 15 to 25% squalene: 1 to 5% cholesterol: 0.1 to 0.5% propylene Glycol: 5 to 15% Sodium lauryl sulfate: 1 to 2% Hydrogenated lecithin: 0.2 to 3% Preservative: 0.02 to 0.1% Purified water: 100% remaining can be blended.

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% Agent: 0.04% Purified water: 100% remaining can be blended.

For example, in the case of blending a weak oil cream, stearic acid: 10 to 20% 2-octyldodecanol: 2 to 5% Hydrogenated egg yolk lecithin: 0.5 to 2% Cetanol: 0.2 to 1 % Potassium hydroxide: 0.2 to 1% Sodium hydroxide: 0.1 to 0.5% Propylene glycol: 4 to 15% Fragrance: Appropriate amount Preservative: Appropriate amount Purified water: The remaining 100% can be blended .

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.

For example, in the case of an emulsion, stearic acid: 1 to 5% Lanolin: 1 to 5% 2-octyldodecanol: 10 to 15% Sorbitan monostearate: 0.2 to 1% monostearic acid Polyoxyethylene 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% of the remaining formulation is possible.

More specifically, for example, stearic acid: 2% lanolin: 2% 2-octyldodecanol: 13% sorbitan monostearate: 0.5% polyoxyethylene sorbitan monostearate 20E. O. : 2% Hydrogenated egg yolk lecithin: 0.1% Triethanolamine: 1% Carboxyvinyl polymer: 0.2% Propylene glycol: 4% Fragrance: proper amount Preservative: proper amount Antioxidant: proper amount Purified water: 100% remaining Is possible.

(Emulsion) The hydrogenated lecithin of the present invention can be used to stabilize a water-insoluble or poorly water-soluble substance in water to form various emulsions. Such an emulsion can be widely used for various cosmetic uses described in this specification.

(Solubilizing Solution) In the present specification, the solubilizing solution is
A substance in which a water-insoluble or poorly water-soluble substance is dissolved in water to form a transparent solution by hydrogenated lecithin. Such a solubilized liquid can be widely used for various cosmetic uses described in this specification.

(Liposome) The liposome of the present invention is a closed vesicle comprising a lipid bilayer membrane containing the above-mentioned hydrogenated lecithin of the present invention as a component of the membrane.

The liposome of the present invention can enclose a water-soluble active ingredient having low affinity for the skin.
This allows the water-soluble active ingredient having low affinity for the skin to easily penetrate the skin. Also,
The release of the active ingredient can be controlled, and the effect can be maintained for a long time.

Specific examples of the water-soluble active ingredient having low affinity for skin include water-soluble polymers such as collagen, elastin, and hyaluronic acid, and moisturizers and whitening agents derived from plant extracts. And cell activating components.

A liposome may contain a fat-soluble or poorly-soluble drug.

A liposome may contain a sugar or a charged substance.

The liposome is prepared by a conventionally known method. For example, it can be produced by dispersing a suspension of hydrogenated lecithin with vigorous stirring, followed by sonication.

The liposome of the present invention can hold a lipid-soluble or poorly-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 humectant having low absorption and affinity for the skin.

[0116] As a constituent of the membrane of the liposome of the present invention, cholesterol may be added in addition to the hydrogenated lecithin of the present invention.

The liposome of the present invention can be preferably used mainly for a cosmetic composition having excellent stability over time. However, it can also be used in compositions other than cosmetic compositions. For example, liposomes are used for functional drugs and functional foods,
It can also be used as medicines and functional foods.

(Pigment) The pigment of the present invention is surface-treated with the above-mentioned hydrogenated lecithin of the present invention.

In the present specification, the pigment means a pigment in a broad sense, and includes not only a coloring pigment but also a special pigment such as a so-called extender having no coloring power and a pearlescent pigment.

Specific examples of pigments include, for example, titanium oxide, zinc oxide, zirconium oxide, red iron oxide, yellow iron oxide,
Black iron oxide, ultramarine, navy blue, chromium oxide, chromium hydroxide,
Inorganic coloring pigments such as mango violet, titanium mica,
Pearlescent pigments such as bismuth oxychloride, talc, kaolin, mica (muscous mica, sericite, etc.), magnesium carbonate, calcium carbonate, aluminum silicate, magnesium silicate, calcium silicate, clay, barium sulfate,
Examples include inorganic extender pigments such as barium carbonate and diatomaceous earth, other various metal powders, magnetic iron oxides, and ceramic powders. Further, organic powders such as plastic powders and organic pigments such as tar pigments can also be used. Further, the surface treatment of the pigment which may be used in combination of the inorganic pigment and the organic pigment can be performed by a conventionally known method.

For example, after the pigment is dispersed in a dispersion medium such as water or alcohol, hydrogenated lecithin is added, and the mixture is heated if necessary.

In order to further strengthen the binding of hydrogenated lecithin to the pigment, for example, after adding hydrogenated lecithin to the pigment dispersion, soluble salts of aluminum, magnesium, calcium, zinc, zircon, titanium and the like ( For example, aluminum sulfate, aluminum chloride, aluminum nitrate, aluminum potassium sulfate, magnesium chloride, magnesium sulfate, magnesium nitrate, magnesium sulfate, magnesium nitrate, magnesium potassium sulfate, calcium chloride, calcium nitrate, calcium acetate, zinc chloride, zinc nitrate, acetic acid An aqueous solution (for example, a 1 to 30% aqueous solution) of zinc, zirconium sulfate, zirconium chloride, titanium chloride, or the like may be dropped so as to be, for example, 0.1 to 2 equivalents to hydrogenated lecithin. Thereby, the hydrogenated lecithin becomes a water-insoluble metal salt and is strongly adsorbed on the pigment surface. It is also possible to simultaneously adsorb neutral fatty oil such as egg yolk oil.

Thereafter, if the dispersion medium is removed by centrifugation or drying using heating or reduced pressure, a pigment surface-treated with hydrogenated lecithin is obtained.

Cosmetics using the surface-treated pigments are smooth and have good elongation, have a moisturizing effect,
It is a cosmetic with less skin irritation and strong water repellency.

The pigment of the present invention can be preferably used mainly for cosmetic compositions having excellent stability over time. However, it can also be used in compositions other than cosmetic compositions, for example, compositions for electronic materials, or various chromatographic carriers.

Examples and preparation examples are shown below, but the present invention is not limited to these.

[0127]

EXAMPLES In the following Examples and Preparation Examples, the iodine value and the lecithin content were measured as follows.

Method for measuring iodine value: The iodine value was measured in accordance with “45. Method for measuring iodine value” based on the standard test method for raw materials for cosmetics.

As described above, lecithin has a liposome-forming ability, iodine is taken into liposomes, the reactivity is reduced, and the iodine-starch reaction is also inhibited. Measurements of low iodine values below are very inaccurate. Therefore, the present inventors adopted the following modified method of measuring the iodine value after hydrolyzing lecithin to lose the ability to form liposomes. Lecithin 1
g, 30 mL of ethanol and 3 mL of a 3N aqueous solution of sodium hydroxide are added, and the mixture is stirred in warm water at 50 ° C for 5 minutes. After cooling to room temperature, 4 mL of acetic acid and n-
Add 30 mL of hexane. Iodine monochloride TS 25ml
Add and shake. If the solution does not become clear, add more carbon tetrachloride, then close it tightly and shield from light.
Shake occasionally at ３０30 ° C. for 30 minutes and leave. Next, 20 ml of potassium iodide solution (1 → 10) and 100 ml of water
After adding and shaking, release iodine by 0.01
Titrate with mol / L sodium thiosulfate aqueous solution. Lecithin composition measuring method: High performance liquid chromatography, measuring conditions: Apparatus: HPLC 6A, 10A (Shimadzu Corporation) Column: Lichrosorb Si-60 (Mer
ck) Radial-Pak cartridge sili
ca (Waters) mobile phase: A, n-hexane / 2-propanol (3 /
4, v / v) B, n-hexane / 2-propanol / water (3/4 /
0.75, v / v / v) 60% B (0-10 minutes), 100% B (10-25)
Min), 60% B (25-30 min) Flow rate: 1.5 mL / min Detector: Evaporative light scattering detector (ELSD) (Varex)
MK III, ALTECH), drift tube temperature:
100 ° C., gas flow rate: 1.75 SLPM.

(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
With 10/2 / n-hexane, ethanol and water
4 (v / v / v) was dissolved in 200 mL of a mixed solvent, and 1 g of a 5% platinum-activated carbon catalyst was added. This mixture is added
The mixture was stirred in a hydrogen atmosphere at 2.0 atm at 30 to 35 ° C for 52 hours. The catalyst was filtered off from the reaction mixture using celite.

The filtrate was concentrated under reduced pressure to about 140 mL, added with 140 mL of warm acetone, stirred, cooled over about 5 hours to -10 ° C, and the precipitated hydrogenated lecithin was collected by filtration and dried under reduced pressure. The yield was 18.0 g.

After dissolving in ethanol as needed, the mixture is concentrated and dried to replace the residual solvent with ethanol.
The iodine value of the hydrogenated lecithin thus obtained was 0.03 when measured accurately by the method described above. The lecithin composition was as follows: PC: 79.0%; PE: 12.8%;
LPC: 3.1%; SM: 1.7%; LPE: 1.8%
Met.

(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
With 10/2 / n-hexane, ethanol and water
4 (v / v / v) was dissolved in 200 mL of a mixed solvent, and 0.4 g of citric acid and 2 g of a 5% palladium-activated carbon catalyst were added. The mixture was stirred at 30-35 ° C. for 60 hours in a 1.5-2.0 atm hydrogen atmosphere. 1 in the reaction mixture
0.8 mL of 4% aqueous ammonia was added to neutralize the citric acid to precipitate as an ammonium salt, and then treated in the same manner as in Preparation Example 1 to measure the iodine value. As a result, iodine value 0.01, lecithin composition: PC: 79.5%; PE: 1
2.5%; LPC: 3.2%; SM: 1.5%; LP
E: 17.8 g of 1.9% hydrogenated egg yolk lecithin was obtained.

(Preparation Example 3) Hydrogen having an iodine value of 0.18 was prepared in the same manner as in Preparation Example 1, except that purified yolk-derived lecithin having a PC content of 60.5% was used as a raw material, and the reaction time was 55 hours. Added egg yolk lecithin was obtained.

(Preparation Example 4) Hydrogen having an iodine value of 0.25 was prepared in the same manner as in Preparation Example 1, except that purified lecithin derived from egg yolk having a PC content of 31.3% was used as a raw material, and the reaction time was changed to 60 hours. Added egg yolk lecithin was obtained.

(Preparation Example 5) As a raw material lecithin, PC
A 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 content of 85.6% was used.

(Preparation Example 6) As a raw material lecithin, PC
A 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 content of 70.4% was used.

(Preparation Example 7) As a raw material lecithin, PC
A 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 content of 30.6% was used.

(Comparative Preparation Example 1) A 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 for the hydrogenation reaction was a solvent consisting of only n-hexane. Was.

(Comparative Preparation Example 2) An iodine value was prepared in the same manner as in Preparation Example 1, except that the solvent used for the hydrogenation reaction was a solvent consisting of only n-hexane, and the reaction time was set to 24 hours. 1.85 hydrogenated egg yolk lecithin was obtained.

(Comparative Preparation Example 3) An iodine value was prepared in the same manner as in Preparation Example 6, except that the solvent used in the hydrogenation reaction was a solvent consisting of only n-hexane, and the reaction time was 60 hours. A hydrogenated soy lecithin of 0.62 was obtained.

(Comparative Preparation Example 4) An iodine value was prepared in the same manner as in Preparation Example 6, except that the solvent used for the hydrogenation reaction was a solvent consisting only of n-hexane, and the reaction time was set to 24 hours. 2.31 hydrogenated soy lecithin was obtained.

(Example 1) Hydrogenated egg yolk lecithin (iodine value 0.03) obtained in Preparation Example 1, hydrogenated egg yolk lecithin (iodine value 0.25) obtained in Preparation Example 4, and Preparation Comparative Example 1 Hydrogenated egg yolk lecithin (Iodine value 0.5
0) and hydrogenated egg yolk lecithin (iodine value 1.85) prepared in Preparation Comparative Example 2 were sealed in a glass bottle and compared in an accelerated test at 50 ° C.

The above-mentioned various hydrogenated lecithin powders were sealed in a glass bottle and allowed to stand at 50 ° C., and changes in the color and odor of the powder 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]

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

[0147]

[Table 2]

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 composition of the resulting neutral cream is as follows: 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% (100% balance is purified water).

The resulting neutral cream is sealed in a container,
The mixture was allowed to stand at 50 ° C., and changes in the color and odor of the powder 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]

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

 ──────────────────────────────────────────────────続 き Continuing from the front page (72) Inventor Takatomo Takai 5-28 Kokudaidai, Komatsu City, Ishikawa Prefecture Inside of YMC Komatsu Office (72) Inventor Isao Togo 7-2-9 Migatadai, Nishi-ku, Kobe City, Hyogo Prefecture

Claims (13)

[Claims] 1. A hydrogenated lecithin having an iodine value of 0.3 or less. 2. The method according to claim 1, wherein the iodine value is 0.1 or less.
2. The hydrogenated lecithin according to 1. 3. The hydrogenated egg yolk lecithin derived from natural egg yolk, wherein the iodine value is 0.3 or less and the composition of phospholipids in natural lecithin is maintained. 4. The method according to claim 3, wherein the iodine value is 0.1 or less.
2. The hydrogenated egg yolk lecithin according to claim 1. 5. A cosmetic composition comprising hydrogenated lecithin having an iodine value of 0.3 or less. 6. The composition according to claim 5, wherein said hydrogenated lecithin is hydrogenated egg yolk lecithin. 7. A method for producing hydrogenated lecithin, comprising:
In a hydrogen atmosphere, in the presence of a hydrogenation catalyst, a natural lecithin is hydrogenated in a reaction solution containing a mixed solvent of an aliphatic saturated hydrocarbon, an aliphatic alcohol, and water to have an iodine value of 0.3.
A method comprising the steps of: 8. The method according to claim 7, wherein said aliphatic saturated hydrocarbon is n-hexane and said aliphatic alcohol is ethanol. 9. The method according to claim 7, 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. The described method. 10. The method according to claim 7, further comprising the step of precipitating the hydrogenated lecithin from acetone. 11. A solution, emulsion or lysate comprising the hydrogenated lecithin according to claim 1 or 2. 12. A liposome comprising the hydrogenated lecithin according to claim 1 or 2. 13. A pigment surface-treated with the hydrogenated lecithin according to claim 1 or 2.