JPH0366604A - Dermal cosmetic - Google Patents

Abstract

PURPOSE:To obtain a dermal cosmetic enhancing water-retentive function of skin, keeping skin in healthy state and exhibiting beauty skin action containing monoacyl-type phospholipid and a compound selected from ceramide, glucosyl ceramide and galactosyl ceramide. CONSTITUTION:The aimed dermal cosmetic contains respectively 0.01-5wt.% a compound expressed by formula I or formula II (R is -CO-C17H35 or -CO-C15H31; X is group expressed by formula III or formula IV, etc.) and at least a species selected from ceramide, glucosyl ceramide and galactosyl ceramide. 1-palmitoyl-3-glyceryl phosphorylcholine and 2-palmitoyl-3-glyceryl phosphorylcholine, etc., are exemplified as the compounds expressed by formula I and formula II. Said dermal cosmetic densifies structure of horny layer in exhibiting strong affinity with said layer and exhibits excellent improving effect of rough skin by enhancing humidity-retentive function with controlling water- retentive property inside of skin.

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to skin cosmetics, particularly monoacyl phospholipids, ceramides, and glucosylceramides.

The present invention relates to a skin cosmetic containing a combination of at least one selected from galactosylceramide.

[Problems to be solved by conventional technology and invention]

BACKGROUND ART Conventionally, in order to maintain healthy skin, a hydrophilic skin moisturizer and an oily skin softener that provide appropriate moisture and oil content to the skin have been blended into skin cosmetics.

Skin moisturizers include glycerin, propylene glycol,
Polyethylene glycol, pyrrolidone carboxylate, etc. are used, but these may absorb water from the stratum corneum, the outermost layer of the skin, causing moisture loss in the skin, and they may also cause large amounts of water to be lost. However, skin cosmetics containing such substances have not always been satisfactory, as they give an uncomfortable feeling such as stickiness.

In addition, liquid paraffin, petrolatum, olive oil, squalane, lanolin, synthetic ester oil, etc. are used as skin softeners, but these are also included in skin cosmetics to the extent that they sufficiently prevent water evaporation from the epidermis. In some cases, they have the disadvantage of interfering with the normal metabolism of the skin.

Regarding the application of ceramides, which are known to exist in living bodies and textiles including the skin, to cosmetics, please refer to JP-A-61-260008 and JP-A-61-271205.
Although there are skin cosmetics disclosed in Japanese Patent Publication No. 2003-120003, even if these components are applied alone to the skin as a cosmetic composition, they are still not sufficient to enhance the moisture retention function of the skin.

Furthermore, monoacyl phospholipids are known to be amphipathic substances with a high affinity for biomembranes, and recently they have been published in Japanese Patent Application Laid-Open Nos. 61-171407 and 61-186305.
As shown in Japanese Patent Application Laid-Open No. 61210016, it is used as an emulsifier and a base for skin cosmetics.

[Means to solve the problem]

In view of the above-mentioned drawbacks of skin moisturizers and emollients, the present inventors do not rely solely on the physical action of these ingredients to replenish moisture to the epidermis or prevent water evaporation from the epidermis. We conducted extensive research with the aim of providing skin cosmetics that maintain or repair the skin in a healthy state by enhancing the skin's inherent moisture retention function.

In other words, water in the skin constantly moves from the inside of the skin to the outer layer along a gradient of water content that decreases as it goes from the dermis to the basal cell layer of the epidermis and then to the stratum corneum, and evaporates to the outside through the stratum corneum. However, this water evaporation mainly occurs from the lamellar granules at the top of the granular layer to the stratum corneum, and from the dense cells &llI
It is controlled by the protective function (barrier function) consisting of the skin, and the amount of transpiration in healthy skin is 0.2 to 0.3 mg/cm''/cm on the skin surface of the forearm under normal conditions.
h r range, typically 0, 25 m g/cm
”/hr.On the other hand, in the case of normal dry skin (dry skin) or dry skin seen in aging skin, T W L (i is the above) depending on the degree of dry skin. The value is at or above the upper limit of the range, indicating a decline in the skin's ability to retain moisture. This may be due to the fact that the defense function is weakened.

Therefore, if the structure of the stratum corneum and lamellar granules can be densified, the moisture retention function of the skin will be enhanced, the skin will be maintained in a healthy state, and dry skin can be improved or repaired. Become.

Therefore, the present inventors conducted extensive research on the effects on human skin of ceramide, glucosylceramide, and galactosylceramide, which have the effect of enhancing the moisture retention function of the skin, and of monoacyl-type phospholipids, which are rich in biomembrane affinity. When ceramides, glucosylceramides, galactosylceracides, and monoacyl phospholipids are combined together in cosmetics and applied to the skin, the results are higher than when ceramides, glucosylceramides, and galactosylceracides are used alone. It has a strong affinity for the surface of the skin and the stratum corneum, the outermost layer of the skin, making their structure denser and reducing moisture 81 inside the skin.
It has been found that it is highly effective in regulating the skin's skin temperature, enhancing the skin's heat-retaining function, and improving rough skin.

Due to these mechanisms of action, the skin cosmetic of the present invention, which is formulated with ceramide, glucosylcerargonide, galactosylceragode, and monoacyl-type phospholipid, improves dry skin by enhancing the moisture retention function. The present invention has been completed by discovering that it has a skin beautifying effect that maintains the skin in a healthy state and prevents its aging, giving the skin iW K8 properties (moist feeling), flexibility (smooth feeling), elasticity, and luster. I ended up doing it.

That is, the present invention is based on the following general formula (1)% formula% Or the following general formula (2) CI(, -O1+ CI+-0-R・・・・・・・・・(2) CI(,-X (In the above formula, R is -CC+Jss, or I -CC15H3+ 1 X is Hz CH.

Contains at least one compound represented by N.(CHi)3e10-P-0-c++, -co, -NeH, or 0θ and at least one selected from ceramide, glucosylceramide, and galactosylceramide. It is a skin cosmetic product.

In the case of the skin cosmetics of the present invention, there is no need to incorporate large amounts of the above-mentioned skin moisturizers and skin softeners as in conventional skin preparations, and there is no risk of interfering with the normal physiological functions of the skin.

The compounds represented by the general formulas fi+ and (2) in the present invention, ie, mono-0-acyl-3-glycerylphosphorylcholine, mono-0-acyl-3-glycerylphosphorylethanolamine, and mono-O-acyl-3-glycerylphosphorylinositol are themselves known. Compounds represented by the general formula fil include 1-valmitoyl-3-glycerylphosphorylcholine, 1-stearoyl-3-glycerylphosphorylcholine, 1-valmitoyl-3-glycerylphosphorylethanolamine 1-stearoyl-3-glycerylphosphorylethanolamine 1
Examples include 1-valmitoyl-3-glycerylphosphorylinositol and 1-stearoyl 3-glycerylphosphorylinositol. Examples of the compound represented by the general formula (2) include 2-valmitoyl-3-glycerylphosphorylconone, 2-stearoyl-3-glycerylphosphorylcholine, 2-valmitoyl-3-glycerylphosphorylethanolan, 2-stearoyl 3- Glycerylphosphorylethanolamine.

Examples include 2-valmitoyl-3-glycerylphosphorylinositol and 2-stearoyl-3-glycerylphosphorylinositol.

Examples of the compounds represented by the above general formulas 10 and (2) include phosphatidylcholine obtained from egg yolk.

It is obtained by using phosphatidylethanolane or phosphatidylinositol as a raw material, treating it with snake venom phospholipase or vancreatin, an intoxicant extracted from pig pancreas, and fractionating it by high performance liquid chromatography. Or, JP-A-61171407, JP-A-61-180
It can also be obtained by the chemical synthesis method described in JP-A No. 305-5 and JP-A-61-210016.

The compounds represented by the above general formulas (1) and (2) in the present invention may be used alone or in combination of two or more.

Ceramide and glucosylceramide used in the present invention.

Galactosylceramide is a compound that exists in trace amounts in the epidermis of mammals such as humans, pigs, cows, horses, and sheep [Biochemistry and Physiology of the Skin, pp. 363-381 ( Biochemistry
and I'hysioligy of the 5
kinOxford [In1versity Pre
ss, Inc., 1983 Ne1i York)
Journal of, Lipifed, Research No. 24S198
3rd year, pages 181-140 (Journal of↓ Lipid Re5erch Volume 24
, 1983), etc.], and can be obtained from the epidermis of these animals by a conventional extraction method. Biochemistry Experiment Course, Volume 3, 20-21
It is possible to use ceraξ-d, glucosylceramide, and galactosylceramide obtained by the production method described in 1974, Nippon Biochemical Complete Edition, Tokyo Kagaku Dojin.

The amount of the compound represented by the above formulas (1) and (2), and the above-mentioned ceramide and glucosylceramide.

The blending amount of galactosylceramide is preferably approximately 0.01 to 5 wt%, respectively, based on the total amount of the cosmetic.
If the amount of any of the compounds of 1) and (2) or cera ξ-do, glucosylceramide, or galactosylceramide is less than the above amount, the effect will not be fully achieved, and even if these amounts exceed the above amount, the effect will be commensurate with the increased amount. cannot be expected to improve.

The skin cosmetics of the present invention may optionally contain pigments.

Flavors, preservatives, surfactants, pigments, antioxidants, and the like may be added as appropriate within the scope of achieving the object of the present invention.

The skin cosmetics of the present invention can be applied to, for example, creams, emulsions, lotions, blowouts, beauty serums, and the like.

〔Example〕

Examples will be described below.

The ceramide, glucosylceramide, and galactosylceramide used in the examples were obtained by the following method.

(Manufacture of galactosylceramide) After cutting the bovine brain into small pieces, acetone was added, and a homogenate was prepared using polyIron. After filtering off insoluble matter, chloroform-methanol (2:1) was added, and after standing overnight, the extract was dried under reduced pressure. Then, the extract was suspended in cold acetone and left to stand at 4°C overnight, and then the precipitate was separated. Further, the same operation was performed using cold ether to obtain a precipitate. Galactosylceramide was separated from the precipitate by silicic acid column chromatography (solvent-chloroform:methanol=2:1).

(Manufacture of glucosylceramide) Glucosylceramide was separated and obtained in exactly the same manner as described above (manufacture of galactosylceramide) except that bovine spleen was used instead of bovine brain.

(Manufacture of ceramide) In the above (manufacture of galactosylceramide), sphingomyelin was separated by using the same silicic acid column chromatography after separating galactosylceramide by changing the solvent to chloroform:Nuknol-1:1. After dissolving this in ether-ethanol (98:2), 100 m
M) Lis-HCl buffer (containing 20mM calcium chloride)
and phospholipase C (derived from Clostridium perfringens, Sigma
(manufactured by Co., Ltd.) was added thereto, and the mixture was shaken at 30°C for 3 hours. Thereafter, chloroform-methanol (2:1) was added, stirred and centrifuged, and the lower layer was separated and dried under reduced pressure. Ceramide was separated from the dried product by silicic acid column chromatography (solvent: chloroform:methanol=1I).

In addition, rough skin improvement effect test, keratin improvement effect test, used to evaluate the skin aging prevention effect of the skin cosmetics of the present invention,
The moisturizing effect test (T W L, (a reduction rate)) skin beautifying effect test (practical test) is as follows.

+1+ Skin Improving Effect Test The effect of applying yE for 4 weeks was investigated on 20 middle-aged and elderly subjects who had rough skin on their lower legs. Approximately 1 g of the sample was applied to the test site of the left lower leg of the subject once a day, and the condition of the skin before and after the test was visually judged according to the following criteria. No sample was applied to the right lower leg, which served as a control.

Judgment criteria for skin dryness: Normal±: Slight dryness, no flaking+: Mild dryness, flaking++: Moderate dryness, flaking+++: Significant dryness, flaking Comparing the judgment results of the test site and control site before and after the test, skin If the dryness has improved by two or more levels (for example, 10--
1,000-±) was considered effective, one level improvement was considered somewhat effective, and no change was considered invalid. Test results are valid;
It is shown by the number of subjects who were somewhat effective.

(2) Stratum corneum improvement effect test Before and after the start and end of the rough skin improvement effect test described above, Scosochi tape and Tiban mending tape) were adhered to the subject's skin, and #JJ was removed to determine the state of the corneocytes attached to the tape. was examined in detail using a scanning electron microscope, and the skin corneocyte anti-exfoliation property was analyzed according to the following criteria to determine the stratum corneum improving effect (keratin cell anti-2II desquamation increasing effect).

Judgment criteria for the effect of improving the stratum corneum Evaluation points 1: No scales observed 2: Small scales dotted 3: Small to medium scales noticeable 4: Large scales noticeable The evaluation is based on the evaluation points of the test site after 4 weeks of Vt application and the control site. It was considered valid if the difference was 2 or more points, slightly valid if it was 1 point, and valid if it was 0 points.

The test results are shown in terms of the number of subjects out of 20 who found the drug to be effective or somewhat effective.

(3) Heat retention effect test (TWL value reduction rate) TWL value and T before and after application of 5Fjt for 4 weeks consecutively on the subject's skin before and after the start and end of the rough skin improvement effect test described above
The reduction rate of WL value (moisture retention function enhancement effect) was calculated as follows to examine the moisturizing effect.

■TWL value A method was used to measure the temperature change of the air above the sealed skin surface over a certain period of time using electrical resistance.

That is, the test subject's skin surface is sealed in a measurement cell, forced dry air is vented into the cell to sufficiently replace the inside of the cell with dry air, and then the ventilation of dry air is stopped and the cell is closed at that point. The relative humidity RH5 (%) in the cell is determined, and then the relative humidity RHIO (%) in the cell is measured again after being left for 10 minutes. From the temperature change at this time, the TWL value (mg/cm
”/hr) was calculated.

However, Dt: Density of saturated water vapor in the air at measurement temperature (t'c) (mg/i') ■ = Volume of cell (1) S: Measurement area (cm'') ■ Low range rate of TWL value The reduction rate of T W L value is the TWL value before and after sample application, T
It was calculated by substituting WLA and TWLB into the following formula.

TWL value reduction rate = (1,-TWLB /TWLA) x 100 (%
) TWLA: TWL value before sample application TWLB: TWL value after sample application Test results where the reduction rate of TWL value is 20% or more as “valid”, and the case where the reduction rate is less than 20% as “invalid” teeth,
The number of subjects who were "effective" out of 20 was displayed.

(4) Beautiful skin effect test (practical test) rough skin, small country,
Samples were given to 20 female subjects (35 to 55 years old) who complained of dry skin etc. twice a day (morning and morning) and the effects were evaluated after 3 consecutive months.The test results were as follows: skin moisture, smoothness, elasticity, For each gender item, the number of respondents who answered ``My skin became moist,'' ``My skin became smooth,'' and ``My skin became taut.''

Examples 1-4. Comparative Example 1 Skin cream below &ll
A skin cream was prepared at Kai, and the ingredients dissolved in the previous step (1) were mixed and dispersed using a homomixer.

Next, each skin cream was prepared by cooling to 30° C. while stirring.

(3) Properties As shown in Table 1, Example 1 is a skin cosmetic of the present invention.
The skin creams No. 4 to 4 were superior to Comparative Example 1 in all of the skin properties, and no abnormality was observed in the blending properties.

Examples 5 to 8, Comparative Example 2 Skin milk Skin milk with the following composition! I! Made and said +21! Ceramide and glucosylceramide in the II production method (C) component.

After preliminarily dissolving galactosylceramide in component (A) by heating at 80°C, add monoacyl phospholipid in component (B) and component (C) to this by heating at 80°C. The mixture was mixed and dispersed in a homomixer, and then cooled to 30° C. with stirring to prepare each skin milk.

(3) Characteristics The results of various tests conducted on each skin milk are listed in the right column of Table 1.

Compared to the cosmetic containing no 1-valmitoyl-3-glycerylphosphorylcholine of Comparative Example 2, 1-valmitoyl-3-glycerylphosphorylcholine was
Example 5 containing 3-glycerylphosphorylcholine
The skin cosmetic of the present invention of No. 8 is prepared by dissolving +21 11 shell method ceramide, glucosylceramide, and galactosylceramide in component (A) at 80°C, and then adding
Component (B) was dissolved by heating at 80° C. [Effects of the Invention] As described above, the skin cosmetic of the present invention enhances the moisture retention function of the skin, maintains the skin in a healthy state, It is clear that it is possible to provide an excellent skin cosmetic product that can repair or repair the skin and have beautifying effects.

Claims (1)

[Claims] The following general formula (1) ▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・・・・・・・
(1) Or the following general formula (2) ▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・・・・・・・
(2) (In the above formula, R is ▲ has a mathematical formula, chemical formula, table, etc. ▼, or ▲ has a mathematical formula, chemical formula, table, etc. ▼ X is ▲ has a mathematical formula, chemical formula, table, etc. ▼ ▲ mathematical formula, chemical formula , tables, etc. ▼ or ▲ mathematical formulas, chemical formulas, tables, etc. ▼) and at least one compound selected from ceramide, glucosylceramide, and galactosylceramide. fee.