JPS61197508A - Hair cosmetic for preventing dandruff - Google Patents

Abstract

PURPOSE:A hair cosmetic for preventing dandruff that contains a hydroquinone glycoside, thus showing high safety and stability, preventing dandruff by its sole use and enhancing the action of zinc pyrithione as an antiseborrheic. CONSTITUTION:(A) 0.1-30wt%, based on the total amount of the cosmetic, of a compound of the formula (R is pentose, hexose, aminosaccharide residue, uronic acid residue, methylated derivative thereof), preferably hydroquinone-beta-D- glucose and, when needed, (B) 0.01-5wt% of at least one selected from zinc pyrithione, 3,4,4'-trichlorocarbanide and vitamin E acetate are used to give the objective hair cosmetic with no irritation and no sensitization, thus permitting long-term application in high dose.

Description

DETAILED DESCRIPTION OF THE INVENTION Field of Industrial Application The present invention relates to a hair cosmetic for preventing dandruff, and more particularly to a hair cosmetic for preventing dandruff having an excellent anti-dandruff effect.

Conventional technology In general, dandruff consists of secretions from sebaceous glands, secretions from sweat glands, peelings from the epidermal layer, etc., and is usually caused by hypersecretion of sebaceous glands, etc., but when the skin is infected with bacteria or yeast, dandruff The outbreak is said to be facilitated pathologically. For this reason, hair cosmetics containing antibacterial agents have traditionally been used to prevent dandruff.

For example, zinc pyrithione (hereinafter referred to as rZP) has been the most effective drug for preventing dandruff.
'rJ) is well known. However, some of these disinfectants have safety problems, and it is preferable to avoid using them in large quantities as much as possible.

Furthermore, the present inventors previously developed trichlorocarbanilide (hereinafter referred to as rTccJ) and vitamin E acetate (
It has been found that VEΔ (hereinafter referred to as 1-VEAJ) or VEΔ alone is superior to ZPT in terms of skin safety and has an anti-dandruff effect. However, TCC has ZPT
Similarly, if used in large amounts, there is a risk of safety problems, and VEA also has the problem that its anti-dandruff effect is not necessarily satisfactory unless it is used for a considerable amount of time.

Problems to be Solved by the Invention In view of the above-mentioned circumstances, the present inventors have developed a hair cosmetic for preventing dandruff that is excellent in safety and stability and further improves the anti-dandruff effects of ZPT, TCC and VEA. As a result of extensive research with the aim of developing a hydroquinone glycoside, we found that hydroquinone glycosides are extremely safe and stable, have anti-dandruff effects on their own, and have Z P T, -r'
Recognizing that the anti-dandruff action of these compounds can be significantly enhanced when used in combination with c c and VEA;
The present invention has now been completed.

Means for solving the problems, the present invention provides (I) an anti-dandruff hair cosmetic comprising a glycoside of hydroquinone represented by the following general formula (+); and (2) (i) ) zinc pyrithione, 3.4
．． At least one compound selected from 4'-trichlorocarbanilide and vitamin E# acid ester;
II) To provide an anti-dandruff hair cosmetic containing a hydroquinone glycoside represented by the following general formula ([) [wherein R is a bean sugar residue, a hexose residue, or a heptose sugar residue] residue,
Indicates uronic acid residues or methylated products of these residues. ] The hair cosmetic for preventing dandruff according to the present invention is non-irritating and has almost no sensitizing properties, and therefore can be used continuously for a long period of time and in high concentrations. Furthermore, when used in combination with ZPT, TCC and/or VEA, ZPT, TCC and/or VE used in combination
The anti-dandruff effect of A can be further enhanced.

Hereinafter, the configuration of the present invention will be explained in more detail.

The hydroquinone glycoside used in the present invention has the general formula (
I), in formula (I), R is L-arabinose, D
-Arabinose, D-xylose, D-ribose, Shi-
Pentose residues such as xylose, L-lyxose, D-ribulose; D-glucose, D-galactose, L-galactose, D-mannose, D-grose, D-fructose, L-sorbose, D-tagatose, D - Hexose residues such as psicose; amino sugar residues such as D-glucosamine, D-galactosamine, sialic acid, aminouronic acid, muramic acid; D-glucuronic acid, D-galacturonic acid, D-mannuronic acid, L- It refers to uronic acid residues such as iduronic acid and L-guluronic acid, or methylated products of these residues, but from the viewpoint of effectiveness in preventing dandruff, ease of availability, stability, and safety, R is In the case of a D-glucose residue, in particular, D-glucose is β-bonded to hydroquinone, that is, hydroquinone β-D-glucose (-ship name:
The use of arbutin (hereinafter simply referred to as arbutin) is most preferred.

Among such glycosides of hydroquinone, arbutin can be used as a commercially available product, but other glycosides, including arbutin, can be prepared by, for example, combining hydroquinone and acetylated sugar with phosphorus oxychloride, sulfuric acid, or thionyl chloride as a catalyst. It can be easily produced by boiling and refluxing for several hours in a suitable solvent and deacetylating the resulting reaction product. Note that these hydroquinone glycosides can be incorporated into the hair cosmetic for preventing dandruff according to the present invention, either alone or as an arbitrary mixture.

There is no particular limitation on the amount of the hydroquinone glycoside of the general formula ([) that is blended into the hair cosmetic for preventing dandruff according to the present invention, but in general, it is based on the total amount of the hair cosmetic for preventing dandruff. 0.1 to 30% by weight, preferably 1 to 20% by weight
Blend. If the amount is less than 0.1% by weight and 9% by weight, the anti-dandruff effect tends to be poor, and conversely, if the amount is more than 30% by weight, no substantial increase in the effect can be expected.

The second embodiment of the hair cosmetic for preventing dandruff of the present invention contains at least one compound of ZPT, TCC and VEA as other essential ingredients.

ZPT has the chemical name zinc bis(2-pyridylthio)-1,
It is a compound known as 1'-dioxide,
For example, Tomicide (manufactured by Yoshitomi Pharmaceutical), Microcide (manufactured by Diachemco), Zinc Omargin (Olin Company, UK 11a)
) and other names.

TCC used in the present invention is a known substance commercially available from, for example, Monsanto. It is in the form of a white powder, and is generally soluble in organic solvents such as acetone and some polyhydric ols, but insoluble or sparingly soluble in water or alcohol. TCC can be blended into cosmetics in accordance with the method for blending general oily substances.

VEA used in the present invention is also a known substance, and is a viscous amorphous oily substance commercially available from Eisai, Riken Vitamin, etc., and is generally soluble in oils and fats, paraffin, organic solvents, etc. However, it is insoluble or poorly soluble in water or aqueous organic solvents. VEA can be blended into cosmetics in accordance with the method for blending general oily substances.

ZPT and TC blended into the hair cosmetic for preventing dandruff of the present invention
Although there are no particular limitations on the amount of C and/or VEA to be blended, generally one or more of these compounds is blended in cosmetics in an amount of 0.01 to 5% by weight.

When these compounds are used alone, the desired effect may not be achieved unless they are blended in a large amount, and if they are blended in a large amount, they may cause skin irritation, which is undesirable. However, according to the present invention, By using the hydroquinone glycoside of general formula (I) in combination, the skin irritation of these compounds is significantly suppressed, and the anti-dandruff effect is also effectively improved. As mentioned above, ZPT, TCC and VEA can be used as a mixture, but in particular ZPT
When PT or TCC is used in combination with VEA, the anti-dandruff effect becomes even better, so it is preferable.
It is preferable to incorporate 05 to 4% by weight of A O, as this provides an excellent anti-dandruff effect.

In addition to the above-mentioned essential ingredients, the anti-dandruff hair cosmetic of the present invention contains other ingredients normally used in flJl hair cosmetics, such as oil, ultraviolet absorbers, antioxidants, surfactants, humectants, fragrances, Water, alcohol, thickeners, preservatives, coloring agents, chemicals, etc. can be added as appropriate.

The hair cosmetics of the present invention broadly refer to those applied to the scalp or hair, such as hair tonics, hair liquids (
/& body conditioning products), scalp emulsions, hair creams, hair shampoos, hair rinses, hair sprays, etc.

Effects of the Invention Next, various evaluation tests were conducted using arbutin in order to clarify the effect of blending the hydroquinone glycoside used in the present invention in hair cosmetics.

(I) Cumulative skin irritation After clipping and shaving the backs of white guinea pigs (5 animals in each group), arbutin concentration of 1%, 5%, 10% and 2
0% ethanol-water (I:l)/8 liquid 50μ7! (l guest or suspension l#i,) was applied once every - day for four days, and the presence or absence of irritation was visually determined every day. The results are shown in Table 1. The numbers in Table 1 represent the number of guinea pigs exposed to stimulation.

As is clear from the results in Table 1, arbutin is a compound that does not cause cumulative skin irritation.

Fujin 1. White Table 1 11 Human Fees and Degree 102 Days 3 Days 4 Days % (MV) After After After (Target After) Rubtin 200,000 (2) Contact Sensitization Test Method 2 Healthy subjects weighing 370-420 g Using guinea pigs, the method of Sato et al.
uraY, Ichikawa 11. Kobayash
i T,eLa BiA ModifiedTechni
Que of Guinea Pig Testing
to IdentityDelayed 1lype
rsensitiviLy Allergens”C
contactDermaLiLis 7.225-2
37.1981).

Judgment criteria: (a) Fields with erythema and fine formations Rating: No erythema at all 01K: Slight erythema 1: Obvious erythema 2: Moderate erythema 3: Strong erythema Items with slight fineness recognized
4 (b) R-tumor formation status Rating: No edema at all 0 Slight edema 1 Moderate R-tumor 2 Strong edema
Three samples were tested: arbutin.

The test results were as shown in Table 2. As is clear from the results in Table 2, it is clear that the sensitizing effect of arbutin is extremely low.

1゛1 All White Table 2 Implant Challenge Sample Noyon % Di% Result Arbutin 5 50/100 (3) Stability over time In order to confirm the stability in the formulation system, the shampoo of Example 1 described below was used. A stability test was conducted. When the degree of coloration was tested after the samples had been stored at 37°C for 1 month, 2 months, and 3 months, almost no coloration was observed in any case. From this result, it is clear that arbutin has extremely good oral stability.

(4) Anti-dandruff effect A test was conducted to evaluate the anti-dandruff effect of arbutin alone or a shampoo containing arbutin and TCC, and a shampoo containing only TCC.

Experiment (I) Add 15 g of triethanolamine lauryl sulfate, 5 g of coconut oil fatty acid jetanolamide, 5 g of arbutin, and appropriate amounts of pigments and fragrances to purified water (total amount of 100 g).
The hair shampoo sample A (sample of the present invention) was obtained by sequentially adding, heating, and cooling.

On the other hand, a sample B (control) was prepared in the same manner as the shampoo with the above composition but without arbutin.

The test was conducted on six men between the ages of 22 and 36 who had a relatively large amount of dandruff.

Wash your hair every 3 days with shampoo sample B for 1 month.
Dandruff accumulated during the day was collected, and the average weight of the collected dandruff (dandruff amount in the control period) was calculated based on the average weight of the collected dandruff (the amount of dandruff in the control period), and the hair was washed every 3 days with the above shampoo sample A for 1 month, and 3 days after the last hair washing at the end of the test period. Weight of accumulated dandruff (test period of the present invention)
compared with.

Accumulated dandruff was collected by suctioning the head using a suction device with a filter cloth.

The results were as shown in Table 3.

The reduction rate of dandruff due to shampoo use was calculated using the following formula.

Reduction rate = [[(Weight of dandruff before the start of the test) - (Weight of dandruff W after 1 month from the start of the test)] / (Weight of dandruff before the start of the test)
) XiOO (%) Table 3 Subject Dandruff amount (mg) Reduction rate Average reduction rate control Invention roll Sample (%) (%) Experiment (If) Add 1 g of arbutin and ZPTSTCC or V to the above sample
Shampoo sample C1D was prepared by blending E A O, 05g.
Or E (product of the present invention) was prepared.

On the other hand, samples F, G, or H (comparative example) were prepared in the same manner as shampoos with the above composition that do not contain arbutin.
was prepared.

For each sample, three men between the ages of 22 and 36 with relatively heavy dandruff were selected for testing.

Before the start of the test, hair was washed every 3 days with Shampoo Sample B for 1 month, and the average weight of dandruff accumulated during the 3 days after hair washing (control period weight) was collected, and the average weight of the collected dandruff and 1
Wash your hair with the above shampoo samples C, D, E, F, G, or H for 3 months, and compare the weight of dandruff accumulated in the 3 days after the last hair wash at the end of the test period (test period for the inventive product and comparative product). compared. Accumulated baldness was collected by suctioning the head using a suction device equipped with a filter cloth.

The results were as shown in Table 4.

12 no, do? ; White Table 4 (I) Sample Subject Dandruff amount (mg) Reduction rate Average reduction rate control Test product roll (%) (%) Table 4 (2) Sample Subject Dandruff amount (mg) Reduction rate Average reduction rate control Test Product roll (%) (%) Table 4 (3) Sample Subject Dandruff amount (mg) '4. Small percentage Average reduction rate control Inventive product roll (%) (%) Examples The present invention will be explained in more detail with reference to Examples, but the technical scope of the present invention is not limited to these Examples. Needless to say. In addition, in the following examples, the compounding amount is weight %.

Example 1 A shampoo consisting of the following formulation was prepared.

The manufacturing method was based on the method of experiment (I) above.

Lauryl sulfate-Na 5 Lauryl sulfate-tri 5 Ethanolamine lauryl dimethylaminoacetic acid 6 Hetain ethylene glycol fatty acid ester 2 Polyethylene glycol 5 Arbutin
1 fragrance
0.3 water
Residue When this shampoo was subjected to a comparative hair washing test with a shampoo without arbutin added to 5 people in the same manner as in the above experimental example, all 5 people judged that it had a dandruff suppressing effect.

Example 2 A shampoo consisting of the following formulation was prepared.

The manufacturing method was the same as in Example 1.

Polyoxyethylene (E, 0.3 mol on average) lauryl ether sulfate-Na 10 (fiff1%
) Polyoxyethylene (E, 0.3 moles on average) Lauryl ether sulfate 7-Triethanolamine Lauric acid jetanolamide 4 Dipropylene glycol 5T CC0.3 Arbutin 0.2 Fragrance
0.3 water
Residue: Similar to Example 1, this shampoo was tested on 5 people in a comparative hair washing test with a shampoo without TCC and arbutin.
The results showed that the product was effective in suppressing dandruff.

Example 3 A shampoo consisting of the following formulation was prepared.

The manufacturing method was the same as in Example 1.

Lauroylmethyltaurine-Na 10 Lauryldimethylaminoacetic acid 8 Betaine lauric acid jetanolamide 4 Ethylene glycol fatty acid ester 1.5 Polyethylene glycol 5V E A
O,5 arbutin
3 fragrances
0.3 water remaining This shampoo was subjected to a comparative hair washing test with a VEA and arbutin-free shampoo on 5 people in the same way as in Example 1, and all 5 people judged it to have a dandruff suppressing effect. Obtained.

Example 4 A shampoo consisting of the following formulation was prepared.

The manufacturing method is the same as in Example 1.

Cocoyl methyl taurine-Na 10 (heavy ff1%) alkyl (Ct□) imidazolinium
6 Bequin type zwitterionic activator Coconut fatty acid jetanolamide 4 Polyoxyethylene polyoxypro 3 Birene brosoc polymer Z P T 0
1IV E A
O-1 Arbutin 0
．． 1 fragrance 0.3
Water The remainder of this nyanpu was prepared by administering ZPT and VE to 5 people in the same way as in Example 1.
When a comparative hair washing test was conducted with shampoo A and arbutin-free shampoo, all five people judged that it had a dandruff suppressing effect.

Example 5 A shampoo consisting of the following formulation was prepared.

The manufacturing method was based on Example 1.

Lauroylsarcosine-Na 10 (1% by weight) Lauryldimethylaminoacetic acid 8 Betaine lauric acid jetanolamide 4 Polyoxypropylene diglycere 5 Lylether TCCO・3 VEA 0・
1 Arbutin 0.1 Fragrance 0.3 Water
Residue Similar to Example 1, this shampoo was subjected to a comparative hair washing test on 5 people with a shampoo without the addition of TCC, VEA, or arbutin, and all 5 people judged that it had a dandruff suppressing effect. .

Examples 6 to 9 and Comparative Examples 1 to 3 Hair rinses having the formulations shown in Table 5 were manufactured by fI, and their dandruff suppressing effects were examined. The manufacturing method was a conventional method.

The Jυ, -Turkish ζ white test was conducted using the above hair rinse after washing the hair with a shampoo containing no anti-dandruff agent, and the dandruff suppressing effect was examined in the same manner as in the case of the shampoo in Examples. As shown in Table 5, the examples of the present invention exhibited excellent dandruff suppressing effects.

Example 10 A hair tonic having the following composition was prepared.

The manufacturing method was to mix and stir ingredients outside the water, and then add this to water.

95% ethyl alcohol (proprietary grade) 50 polyoxyethylene (40 mol) hardened 0.5 castor oil V E A O,
3 Arbutin 1.0 Fragrance 0.5 Water
Residual This hair tonic showed excellent dandruff control effect.

Example 11 A hair liquid (liquid hair styling product) having the following composition was prepared. The manufacturing method is based on Example 1o.

95% ethyl alcohol (proprietary grade) 5° polyoxypropylene (40 mol) 15 Butyl ether V E A 1.0
Arbutin 0.5 fragrance
0.5 water
The residue of this hair liquid is
It showed excellent dandruff control effect.

Example 12 A hair cream having the following composition was prepared.

Part (A) was heated and stirred, added to part (B) which was also heated, emulsified, and then cooled to produce the product.

(A) Liquid paraffin 15 Cetyl alcohol 5 Vaseline
4 Glycerin stearate 3 Polyoxyethylene (20 mol)
1 oleyl alcohol VEA
2T CC0.2 Arbutin 0.5 Fragrance
015(B) Dipropylene glycol lO water
Residual This O/W type hair cream showed excellent dandruff suppressing effect.

Example 13 A hair lotion having the following composition was prepared. (A
) were mixed and stirred and added to part (B) to produce the product.

(A) 95% ethyl alcohol (proprietary grade) 40
Dimethylpolysiloxane 0.5 Liquid paraffin 0.5 Polyoxyethylene (40 mol) 0.5 Hardened castor oil Acrylic resin Alkanolamine liquid 0.5 VEA
0.5 Hydroquinone-β-L -1,0 Arabinocyte fragrance 0.2(B)
dipropylene glycol 3 water
Residual This hair lotion showed excellent dandruff control effect.

Example 14 A hair lotion having the following composition was prepared. The manufacturing method was based on Example 13.

(A) 95% ethyl alcohol (proprietary grade) 50 dimethylpolysiloxane 2 liquid paraffin 2 stearyltrimethylammonium 0.3 um chloride VEA O,1 arbutin 0.1 fragrance
0.2(B) 1.3-butylene glycol 5 water
Residual This hair lotion showed excellent dandruff control effect.

All of the anti-dandruff hair cosmetics of Examples 1 to 14 produced above had excellent anti-dandruff effects, low skin irritation and sensitization, and excellent stability over time.

Claims (1)

[Claims] 1. A hair cosmetic for preventing dandruff, which contains a hydroquinone glycoside represented by the following general formula (I). ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I) [In the formula, R is a pentose residue, a hexose residue, an amino sugar residue,
Indicates uronic acid residues or methylated products of these residues. 2. (i) at least one compound selected from zinc pyrithione, 3,4,4'-trichlorocarbanilide and vitamin E acetate, and (ii) hydroquinone represented by the following general formula (I). A hair cosmetic for preventing dandruff containing glycosides. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I) [In the formula, R is a pentose residue, a hexose residue, an amino sugar residue,
Indicates uronic acid residues or methylated products of these residues. ] 3. The content of component (i) in the hair cosmetic for preventing dandruff is 0.
．． The skin external preparation according to claim 1, wherein the amount is 01 to 5% by weight.