JPS60202813A - Treatment of skin - Google Patents

Abstract

PURPOSE:A treatment of the skin for preventing, remedying, and treating effectively acne, preventing effectively dandruff when it is applied to the scalp, comprising a reaction product of an unsaturated aliphatic alcohol and sulfur as an active ingredient. CONSTITUTION:100pts.wt. aliphatic alcohol (preferably 6-36C straight-chain or branched chain alcohol) containing one or more unsaturated bonds in the molecule is reacted with 0.1-150pts.wt., preferably 0.5-50pts.wt. sulfur at 130-220 deg.C. 100pts.wt. total amount of treatment components is blended with 0.01-20pts.wt., preferably 0.1-10pts.wt. of the prepared reaction product. The reaction product has higher viscosity with rise in amount of sulfur, and the reaction product which is liquid at room temperature, viscous state, waxy state, or solid state is obtainable.

Description

[Detailed description of the invention] The present invention relates to a skin application containing a reaction product of as an active ingredient.

This skin application is particularly effective in the prevention, treatment, and treatment of acne (so-called acne), and can also be used on the scalp to effectively prevent dandruff.

Conventionally, sulfur has been used in skin ointments or skin cosmetics, but in this case the sulfur was in the form of powder or dispersion. Therefore, when conventional products were applied to the skin, most of the sulfur merely served to cover the skin surface, and only a small portion of the sulfur was involved in producing medicinal or cosmetic effects. Therefore, it is not possible to expect a satisfactory effect from conventional products, and in order to obtain a strong effect, it is necessary to increase the amount of use, and as a result, there is a risk of inflammation due to skin irritation. Further, powdered sulfur has the disadvantage that it causes so-called dullness on the skin surface, making it difficult to use.

As a result of research conducted by the present inventors in order to eliminate these drawbacks, the present inventors found that when a reaction product of unsaturated aliphatic alcohol and sulfur is used as an active ingredient, an effective skin preparation free of the above drawbacks can be obtained. They discovered this and completed the present invention.

That is, the present invention is a skin preparation containing as an active ingredient a reaction product of an aliphatic alcohol having one or more unsaturated bonds in the molecule and sulfur.

The skin application composition of the present invention is an external skin preparation such as an ointment, or a skin cosmetic such as a cream.

Applied to the skin as a scalp preparation. In particular, this product is effective for preventing, treating, and treating acne when applied to the skin.
It is also effective in preventing dandruff when applied to the scalp.
It is extremely useful as a skin application material.

In the present invention, the aliphatic alcohol having one or more unsaturated bonds in the molecule preferably has 6 to 3 carbon atoms.
A straight or branched chain having 6 double bonds,
Typical examples include 2-hexenol, 2-octenol, 2-totisenol, 2-tetrazocenol, 2-
Hexadecenol, 2-octadecenol, palmitole alcohol, oleyl alcohol.

Elysil alcohol, rilyl alcohol.

eleostearyl alcohol, lysyl alcohol,
erucil alcohol, craniol.

Linalool, bisabolol, etc. can be mentioned.

The active ingredient of the present invention is a reaction product of such unsaturated aliphatic alcohol and Seihuang.

The reaction is usually carried out between an unsaturated aliphatic alcohol and sulfur at a temperature of 130~
The reaction is carried out at 220°C, preferably from 15 to 150°C, in the presence or absence of a catalyst. Sulfur is usually used in an amount of 0.1 to 150 parts by weight, preferably 05 to 50 parts by weight, per 100 parts by weight of unsaturated aliphatic alcohol.

The resulting reactant becomes viscous as the amount of sulfur increases. Therefore, depending on the amount of sulfur, the reactants range from liquid to viscous, waxy, and solid at room temperature.

The reactants are mainly those produced by the crosslinking reaction with sulfur at the unsaturated bond sites of the unsaturated aliphatic alcohol, but may also contain other sulfur reactants such as merkanotides, and even unreacted products. .

For example, the reaction product obtained by reacting 80 M parts of oleyl alcohol with 20 parts by weight of sulfur is a brown liquid (room temperature),
This is subjected to GPC (glue filtration chromatography), N
As a result of examination using MR (nuclear magnetic resonance), mass spectrometry, infrared spectroscopy, etc., it was found that a cross-linked reaction product had two molecules of oleyl alcohol bonded to each other by sulfur at the double bond site, and a cross-linked reaction product had three molecules of oleyl alcohol bonded to each other at the double bond site. It was confirmed that the crosslinking reaction product, in which four molecules of oleyl alcohol were bonded, and an unreacted product were also included.

Unlike powdered sulfur, the reactant in the present invention has the property of being dissolved in ethanol, solubilized or emulsified by various surfactants, and has antioxidant ability against oily components such as olive oil. Ru.

The skin preparation of the present invention contains the above-mentioned reactant as an active ingredient, and contains other usual ingredients. Typical ingredients include oil, water, emulsifiers, humectants, powders, thickeners, antioxidants, preservatives, fragrances, and the like.

Regarding the amount relationship, the total amount of reactants of active ingredients is 10
0.01 to 20, preferably 0.1 to 1 per part of 0N
It is 0 parts by weight.

In the skin application material of the present invention, unlike powdered sulfur, most of the sulfur is involved in the expression of medicinal or cosmetic effects, and therefore the amount of sulfur is small and does not cause side effects such as skin irritation. In addition, it does not feel rough on the skin and has a good feel when used. Surprisingly, the skin preparation of the present invention can be used on the scalp to significantly prevent dandruff, acne, etc. The skin application material of the present invention is
When an oily component is blended, quality deterioration due to oxidative denaturation of the oil does not occur.

Next, we will discuss the dandruff prevention effect.

The preventive effect on dandruff was determined based on the results of use tests on rabbits and humans.

(1) Use on rabbits A rabbit was used as the test animal, and a 20% methanol solution of oleic acid was applied to the outside of the ear wings on both sides of the rabbit. After applying oleic acid, a methanol solution of oleyl alcohol and a sulfur reactant at a predetermined concentration was applied to the outside of one ear wing.

This operation was performed once a day for a total of 4 days.

Dandruff-like substances were formed in the ear wings to which only oleic acid was applied, whereas dandruff-like substances were formed in the ear wings to which oleic acid and the oleyl alcohol sulfur reactant were applied, in proportion to the concentration of the oleyl alcohol sulfur reactant. formation is no longer recognized.

The results are shown in Table (1).

Table (1) [Formation of dandruff-like substance] (Note) +: Formation of dandruff-like substance is observed.

±: Formation of a crack-like substance is hardly observed.

−: Formation of dandruff-like substance is not observed.

(Note) ■; Comparative Example (2) Human use test As shown in the table (2) below, channeau and hair tonic containing oleyl alcohol sulfur reactant and 2-octenol sulfur reactant were prepared, and the anti-dandruff effect was tested. investigated.

Forty men between the ages of 22 and 39 with dandruff were selected as subjects, and a total of 40 men (10 for each sample) were tested.

The shampoo sample is used when washing hair, and the hair tonic sample is used when washing hair.
The amount of dandruff before the start of the test was compared with the amount of dandruff on the second day of hair washing at the end of the one-month test, and if the amount of dandruff at the end of the test was small, it was considered to be effective in preventing dandruff. If the amount of dandruff did not change or if it increased, it was determined that there was no dandruff suppressing effect.

Got the results.

Table (2) It is said that keratinization occurs in the pores and the pores become clogged. Furthermore, it is said that the cause of inflammation is the stimulation of free fatty acids produced when sebum is decomposed by P. acnes. Therefore, currently, in the treatment of acne, disinfectants that have a bactericidal effect against acne bacteria and exfoliants that open pores are often used.

Therefore, in order to confirm the effectiveness of the product of the present invention against acne, the keratin exfoliating effect was investigated.

(1) Bactericidal test against Propionibacterium acnes
ne8. Our laboratory isolate, approximately 5 X 1 '0' ce
lllll/mi) with the sample and phosphate buffer (pH 7,0)
mixed inside. At this time, since the unsaturated alcohol sulfur compound and oleyl alcohol in the sample are insoluble in water, 2%
Tween 80 was added and the test was conducted in a dispersed state.

After 60 minutes, sample 1 ml of Q, 1/10
Diluted 0 times. Thereafter, 0.1 ml of the bacterial cells was inoculated into a CAM large plate culture medium (Mizu Seiyaku Co., Ltd.) and incubated at 37°C.
The cells were cultured anaerobically for 4 days.

The number of viable bacteria in the resulting colonies was measured, the ratio to the number of viable bacteria when the sample concentration was 0% was calculated, and the killing rate was calculated from that value to compare the bactericidal effects of each sample. The results were as shown in Table (3) below.

Table (3) (Note) ■, ■: Comparative example (2) Keratin exfoliation test Does dansyl specifically bind to stratum corneum?
A test was conducted using Fuku5-=a id as a marker.

5% Danzyl chloride (base, white petrolatum) 100
Apply a thin layer of μl to a Tsuchi test bandage (1 cm in diameter), and apply this to a hairless mouse (♀ body weight 10-2 cm).
Or) L- was occluded and applied to the backs of 25 animals for 24 hours.The stratum corneum was then fluorescently stained. Next, 50 μl of each sample at various concentrations was applied to the fluorescent area once a day. The end point for judgment is the day when the fluorescence of the existing stratum corneum disappears under long wavelength ultraviolet rays in a dark room.
The exfoliating effect of the sample was measured by the number of days required for the fluorescence to disappear (average of 25 mice). The results were as shown in Table (4) below.

Table (4) (Note) ■, ■, ■: Comparative example From the results of the above table (4), the inventive example requires fewer days for fluorescence disappearance than the comparative example, and exfoliation to open acne-affected areas. It can be seen that it causes acne to appear quickly and therefore has an excellent therapeutic effect on acne.

As is clear from the above, the skin preparation of the present invention has excellent anti-dandruff and acne treatment effects.

Examples and synthesis examples of the present invention are shown below.

Example 1 (Production of emulsion) (Ingredients of Al Amount (wt%)) Setanol 1.5 Stearic acid 1.0 Lumitic acid 05 Liquid lanolin 1.0 Squalane 20 Isopropyl myristic silicate 1.0 Monostearic acid Glyceryl 1.5 Tween 20 0.5 Oleyl alcohol/10% sulfur reactant 0.5 Preservatives and fragrances Appropriate amount (Component of Bi Propylene glycol 3.0 I-lyethylene glycol 400 2.0 Triethanolamine 10 Purified water 845 Above ( A mixture was obtained by mixing each component of Al. Separately, a mixture of (Bl) was obtained in the same manner. (A mixture of Al and (
Each mixture of Bl was heated and dissolved at 70° C., and the mixture of (N) was added to the mixture of (Bl) and emulsified using an emulsifier, followed by heat exchange and cooling to produce an emulsion.

This emulsion was shown to be highly effective in treating acne and preventing dandruff.

Example 2 (manufacture of cream) (Al component blending amount (wt%) Setanol 4.0 Stearic acid 2.0 Waseri 74.0 Liquid paraffin 10.0 So I1-propyl millimethi4ate 50 Monostear food Guri A 3. Q Oleyl Alcohol 20% 4 & Yellow Reactant 1. .

(Component of Bl Glycerin 5.0 Zoropylene glycol 5.0 Potassium hydroxide 0.2 Purified water 60.8 A cream was produced in the same manner as in Example 1.

This product has also been shown to be highly effective in treating acne and preventing dandruff.

Example 3 (manufacture of cream) (Original ingredients blended amount (wt%) Setanol 4.0 Stearic acid 2.0 Vaseline 4゛0 Ryu no Ya Rough-in 10.0 Miristi 4 isozolovir 5.0 Monosteari m glyceryl 3.0 Hexenol 20% sulfur reactant 1.5 (Component of Bl Glycerin 5.0 Propylene glycol 5.0 Potassium hydroxide 0.2 Purified water 603 A cream was produced in the same manner as in Example 1.

This product also showed remarkable efficacy in treating acne and preventing dandruff.

Example 4 (Cream detergent) (Components of N Amount (% by weight) Stearic acid 60 Noglumitic acid 10.0 Myristic acid 10.0 Lauric acid 80 Glyceryl monostearate 2.0 Glycerin 20.0 Propylene glycol 10.0 Oleyl Alcohol/2094 Yellow Reactant 0.5 Flavor
Appropriate amount (components of Bl Potassium hydroxide 7.0 Purified water 26.5 Cream cleanser (scalp application) in the same manner as in Example 1
was manufactured. This product was highly effective in preventing dandruff.

Example 5 (soft plaster) Ingredients Amount (wt%) Solid paraffin 10.0 Peace wax 100 Squalane 10.0 Oleyl alcohol/10% sulfur compound 1. .

Perfume Appropriate amount of petrolatum 69 The above components were mixed and the mixture was heated and dissolved at 80'C, followed by stirring and cooling to obtain an ointment. This product was highly effective in treating acne.

Example 6 (Shampoo) Ingredients Amount (wt%) Coconut oil fatty acid ethanolamide 50 Oleyl alcohol, 20% fif + yellow reactant 0.5 Preservatives, fragrance Appropriate amount Purified water 695 Shampoo was obtained in the same manner as in Example 6. Ta. This product was applied to the scalp and showed remarkable effectiveness in preventing dandruff.

Example 7 (Rinse) (Ingredients of Al Amount (wt%)) Setanol 2.0 Glyceryl monostearate 3.0 Oleyl alcohol 20% 4 Yellow reactant 10 Preservative
Perfume Appropriate amount (components of 81) Stearyltrimethylammonium chloride 2j Propylene glycol 7.0 Purified water 845 A rinse was obtained in the same manner as in Example 1. This rinse was also applied to the scalp and showed remarkable effectiveness in preventing dandruff.

Implementation 1 Tali 8 (hair tonic) Ethyl alcohol 55fK oleyl alcohol 20%
'tb yellow 15 thing 0.5 fi', Niracol H
An alcoholic phase was obtained by dissolving CO-60,1,Of and fragrance under a suitable lid at room temperature. Purified water 42. ! Glycerin 10 for l'? and a suitable amount of the color chart were dissolved under heating and cooled. The alcohol phase was added to the obtained aqueous phase to solubilize it to obtain a hair tonic.

This product was applied to the scalp and showed remarkable effectiveness in preventing dandruff.

Synthesis 4 evenings lj 1. (Synthesis of oleyl alcohol/20% sulfur reactant) 20 f/JT powder was added to oleyl alcohol 802, and the reaction was carried out at 150 to 160°C for about 2 hours under nitrogen gas to obtain a brown oil.

Synthesis Example 2 (Synthesis of oleyl alcohol/10% sulfur reactant) Sulfur powder 10& was added to oleyl alcohol 902, and a brown oil was obtained in the same manner as in Synthesis Example 1.

Synthesis Example 3 (Synthesis of hexenol/5% sulfur reactant) hL yellow powder 5y was added to 3-hexen-1-ol 95P, and a brown oil was obtained in the same manner as in Synthesis Example 1.

Synthesis Example 4 (Synthesis of hexenol/20% sulfur reactant) 3-hexen-1-ol 802 and sulfur powder 201? was added to obtain a brown oil in the same manner as in Synthesis Example 1.

Synthesis Example 5 (Synthesis of octenol/20% sulfur reactant) Sulfur powder 207 was added to 80y of 1-octen-3-ol, and a brown oil was obtained in the same manner as in Synthesis Example 1.

Synthesis Example 6 (Synthesis of butynol/20% sulfur reactant) Sulfur powder 2Of' was added to 2-buten-I-ol 802, and a brown oil was obtained in the same manner as in Synthesis Example 1.

Synthesis Example 7 (Synthesis of Erucil Alcohol/15% Sulfur Reactant) Erucil Alcohol 85.29 K Ken Huang Powder 14-92
was added, and the reaction was carried out at 150 to 160° C. for about 2 hours under an air stream. A brown solid was obtained at room temperature.

Synthesis Example 8 (Synthesis of geraniol, 10% is a yellow reactant) Sulfur powder 107 was added to geraniol 90fi', @
A brown oil was obtained in the same manner as bottom side 7.

Synthesis Example 9 (Synthesis of linalool/sulfur reactant) Sulfur powder 107 was added to linalool 905' and a brown oil was obtained in the same manner as in Synthesis Example 7.

Synthesis Example 10 (Bisabolol 10% Synthesis of Yellow Reactant) Sulfur powder 10f was added to 90fi' of bisabolol, and a brown oily substance was obtained in the same manner as in Synthesis Example 7.

Patent applicant Shiseido Co., Ltd.

Claims (2)

[Claims] (1) A skin application material containing as an active ingredient a reaction product of sulfur and an aliphatic alcohol having one or more unsaturated bonds in the molecule. (2) The skin preparation according to claim (1), which contains a reaction product of oleyl alcohol and sulfur as an active ingredient.