JPS6026086B2 - cosmetics - Google Patents

Description

[Detailed description of the invention] The present invention is non-irritating to the skin, has high safety and affinity, is key to stability over time, emulsion stability, feeling of use, etc., and has good appearance (texture, gloss). The present invention relates to cream-like, emulsion-like, lotion-like, oil-like skin cosmetics and hair cosmetics such as hair styling products, hair conditioners, shampoos, and conditioners.

Conventionally, the conditions that many cosmetics should meet are: [1]
Highly safe without irritating the skin, etc.

'21 Character L Ihi stability and stability over time. '3}
Good affinity for skin, etc. ■It must be easy to use. ■ Good appearance, such as texture and gloss, etc. are mentioned. However, these conditions can only be met by using appropriate cosmetic raw materials, and the selection of raw materials is the most important issue.

Cosmetics generally consist of ingredients other than water, such as oily bases (fats, oils, waxes, higher alcohols, hydrocarbons, ester oils, etc.), wetting agents, surfactants, ethanol, fragrances, etc. Surfactants are not used because they have a great influence on the factors mentioned above, such as emulsion stability, stability over time, resistance to freezing of the skin layer, physiological safety, affinity for the skin, feel of use, appearance, etc. Care must be taken when doing so. It is especially widely used as a nonionic surfactant and solubilizer. Among them, those that are relatively good in terms of skin irritation, toxicity, emulsifying power, etc. are currently being used as cosmetic raw materials, but it has not yet been possible to find one that satisfies all of the above conditions. for example,
Polyoxyethylene higher alcohol ethers such as polyoxyethylene oleyl ether and polyoxyethylene cetyl ether are highly irritating to the skin and have poor emulsion stability.

In addition, glyceryl stearyl ether, glyceryl cetyl ether, glyceryl lauryl ether (monoester, ether) and the like have poor emulsifying properties, and the resulting creams, for example, have poor texture, gloss, and stability over time. In addition, polyol higher fatty acid esters such as glycerin higher fatty acid ester, sorbitan higher fatty acid ester, and polyethylene glycol higher fatty acid ester have poor emulsion stability.
It is prone to gelation and has poor stability over time. Furthermore, with regard to higher fatty acid esters and amides such as jetanolamine, the former does not have sufficient emulsifying power, and the latter has some skin irritation, although it is slight, and therefore its use is limited. was. In view of the current situation, the present inventors conducted extensive research and found that the compound represented by the general formula below does not irritate the skin, is physiologically safe, and is suitable for inclusion in cosmetics. The present invention has been completed based on the discovery that not only the stability is significantly increased, but also the usability, appearance, etc. are extremely excellent, and all the drawbacks of conventional nonionic surfactants are overcome.

The purpose of the present invention is to provide cream-like, emulsion-like, lotion-like, and oil-like products that are non-irritating to the skin, have physiological safety, high affinity, excellent emulsion stability, and long-term stability, and have a good appearance. The purpose of the present invention is to provide skin cosmetics and hair cosmetics such as hair styling products, hair conditioners, shampoos, and conditioners.

That is, the present invention provides a general formula (wherein R is n-decyl group, n-dodecyl group, n-tetradecyl group, n-hexadecyl group, 2-hexadecyl group, 2-hexyldecyl group, n-octadecyl group, 2
-heptylundecyl group, 2-(1,3,3-trimethyl)-butyl-5,7,7-trimethyloctyl group, n
-9-octadecenyl group, 12-hydroxy-n-octadecyl group, 12-hydroxy-n-9-octadecenyl group, 2-octyldodecyl group, n-docosyl group, R2
It is or.

) Hereinafter, embodiments of the present invention will be explained in detail.

Furthermore, among the compounds represented by the above general formula used in the present invention, for example, y-(N-1,1-dimethylolethyl)
Aminopropylene glycol Q-decyl ether, y-(N-1,1-dimethylolethyl)aminopropylene glycol Q-dodecyl ether, y-(N-1,1-dimethylolethyl)aminopropylene glycol-tetradodecyl ether , y-(N-1,1-dimethylolethyl)aminopropylene glycol Q-octadecyl ether, y-(N-1,1-dimethylolethyl)aminopropylene glycol Q-2-heptyl undecyl ether, y- (N-1,1-dimethylolethyl)aminopropylene glycol Q-n-9-octadecenyl ether, so(N-1,1-dimethylolethyl)aminopropylene glycol Q-12-hydroxyoctadecyl Ether, y-(N-trimethylolmethyl)aminopropylene glycol Q-tetradecyl ether, y-(N-trimethylolmethyl)aminopropylene glycol Q-2-heptyl undecyl ether, y
-(N-trimethylolmethyl)aminopropylene glycol Q-12-hydroxyn-octadicenyl ether, y-(N-trimethylolmethyl)aminopropylene glycol Q-2-octyldodecyl ether, y-(N-trimethylolmethyl ) Aminopropylene glycol cosyl ether, y-(N-2,3,4,5,6-
Pentahydroxyl) aminopropylene glycol Q-
2-(1,3,3-trimethyl)butyl-5,7,7-
Trimethyloctyl ether, y-(N-2,3,4,
5,6-pentahydroxyhexyl)aminopropylene glycol Q-dodecyl ether, y-(N-trimethylolmethyl)-aminopropylene glycol Q-9-octadecenyl ether, y-(N-2,3,4 ，
5,6-pentahydrohexyl)aminopropylene glycol Qn-9 octadecenyl ether, N-2-hydroxy-3-desyloxypropylglucosamine, N-
2-hydroxy-3-(2-heptylundecyloxy)propylglucosamine, N-2-hydroxy-3-(12
Preferred examples include -hydroxy-9-octadeceloxy)propylglucosamine and N-2-hydroxy-3-dodecyloxypropylgalactosamine.

The compound represented by the general formula of the present invention can be obtained by mixing at least one of them with the base of the cosmetic by a known method.
It is contained in the cosmetic.

The amount used (content) is usually 0.1 to 3 fish% by weight (preferably 1 to 20% by weight) based on the weight of the Ikeboko material.
) is within the range. For example, in the case of skin cosmetics, it is usually blended in an amount of 1 to 1% by weight, and in the case of hair preparations, it is often used in a range of 5 to 2% by weight.

The compound represented by the general formula used in the present invention is a higher alcohol (the number of carbon atoms in the alkyl group or alkenyl group is 1
0 to pine) glycidyl ether and 1 mole thereof
．． It can be obtained in high yield by heating and carrying out an addition reaction with 2 to 3 times the mole of the alkanolamine.

The compounds represented by the above general formula are generally colorless, pale yellow crystals, paste-like, or liquid, and many of them are easily soluble or eluent-soluble in water, and readily compatible with alcohol, petroleum ether, IJ gloin, and the like.

An example of its synthesis is shown below.

Synthesis Example 1 Synthesis of y-(N-trimethylolmethyl)aminopropylene glycol and Q-hebutyl undecyl ether In a 2,000-inch flask equipped with a reflux condenser, 200 g of trimethylol aminomethane was added. Glycidyl 2-
Add 400 heptyl undecyl ether, 11 pi 0
The mixture was allowed to react for 3 hours.

After the reaction, 1,000 ml of petroleum ether was added to the contents, and the mixture was stirred thoroughly and then allowed to stand at room temperature for 2 hours. Precipitated unreacted trimethylol aminomethane is removed by decantation, and the supernatant is concentrated. The residue was then distilled under high vacuum (0.05 Torr) to 160
By removing the crab matter up to 510°C, the target compound was obtained at 510° C., yield was uneven, pale yellow, paste. It was confirmed through various analyzes (m, NR, MS, etc.) that this product was the above-mentioned target compound. Synthesis Example 2 Synthesis of y-(N-1,1-dimethylolethyl)aminopropylene glycol Q1n-9-octadecenyl ether In a reactor similar to Synthesis Example 1, 2-amino-2-methyl-1 , 3-propanediol 2009, glycidyl oleyl ether 410, and while vigorously worshiping, 1
The reaction was carried out for 3.5 hours at 10:00 am.

After completion of the reaction, the same post-treatment as in Synthesis Example 1 was carried out to obtain 516 mm of the target compound. Yield 95%. pale yellow paste. The product thus obtained was also analyzed in the same manner as in Synthesis Example 1, and was confirmed to be the target compound.

Synthesis Example 3: y-(N-2,3,4,5,6-penta.
Synthesis of (hydroxyl) aminopropylene glycol Q-docosyl ether 1.3 mol of glucanin is used instead of 200 mol of trimethylol aminomethane, and 1.0 mol of glycidyl docosyl ether is used instead of 400 mol of glycidyl'2-heptyl undecyl ether. Other procedures were carried out in the same manner as in Synthesis Example 1 to obtain the target compound.

Yield 91%. Pale yellow semisolid. Synthesis Example 4: Synthesis of N-2-hydroxy-3-decyloxypropylglucosamine 1.2 mol of glucosamine instead of 200 mol of trimethylol aminomethane, glycidyl decyl ether instead of 400 mol of glycidyl 2-heptyl undecyl ether The same procedure as in Synthesis Example 1 was carried out except that 1.0 mol was used to obtain the target compound.

Yield 92%. Pale yellow semi-field. Synthesis Example 5: Synthesis of N-2-hydroxy-3-dodecyloxypropylgalactosamine 1.2 mol of galactosamine instead of 200 mol of trimethylol aminomethane, and glycidyl 2- instead of 400 mol of glycidine 2-heptyl undecyl ether The same procedure as in Synthesis Example 1 was repeated except that 1.0 mol of butyl undecyl ether was used to obtain the target compound.

Yield 90%. Pale yellow semisolid. The compound represented by the general formula of the present invention has little irritation to the skin, similar to the compounds shown in Table 1 below. The coated batch piece is pasted on the skin of white domestic rabbits (three rabbits were used) whose back hair has been shaved.

Cover the rabbit with a rubber garment and secure it in the animal holder to prevent it from moving. After 2 hours, remove the batch pieces and record the degree of reaction according to the criteria below.

The determination is also made after 72 hours, and the average value of the scores after 2 hours and after 7 hours is calculated, and the stimulation score is set as 1. Judgment: [1' No erythema or skin-forming erythema -0 Very slight erythema 11 Confirmed erythema
-2 Moderate to severe erythema -
3 Severe erythema and slight skin formation -4'2} Edema formation No edema 10 Very slight edema 11 Slight edema
-2 Moderate edema -
3 Severe edema - 4 Evaluation: Based on the calculated score-value, the degree of irritation is evaluated as follows.

0-2 Slight irritation or almost no irritation 5 or less in 22 Moderate irritation 5 or more Strong irritation Next, a primary skin irritation test was conducted on the human body and it was found to be non-irritating.

(Table 1) B Human skin joint longitudinal test method: Using the closed patch test method, a flannel cloth (1.5 skin square) coated with the material to be tested is applied to the upper or front inner side, and a bandage is placed over it. Cover with.

After 2 hours, remove the flannel cloth and sample, and judge the degree of reaction according to the criteria below, and also after 4 hours.

Judgment: No change at all... - Faint erythema... 10 Obvious erythema... 10 In addition to erythema, edema, vesicles, etc. are observed" 10 Rating: (10) (10) was considered positive, and evaluation was performed based on the positive rate.

However, the subjects were 50 randomly selected males and 50 females. Preparation of test samples: Olive ponds containing 1% by weight of each of the test substances listed in Table 1 were prepared.

This was used as the test sample. Table 1 Bamboo 0: The above M. 9~M
．． Compound 14 is a conventional nonionic surfactant.

As is clear from the above, the compounds represented by the general formulas '1} and '21 used in the present invention cause much less irritation to the skin than conventional nonionic surfactants.

Further, as a result of an oral toxicity test using mice, it was confirmed that all the compounds in Table 1 had an LD5.20/k9 or higher.

The compounds represented by the general formulas 01 and '2} according to the present invention are not only hypoallergenic and non-soil as described above, but also all of them are based on ordinary oily bases (e.g. liquid paraffin,
It is completely dissolved or miscible in oils and fats, ester oil, wax, higher alcohols, etc.) and is also well dispersed or dissolved in water.

Therefore, in the case of an emulsified type of material, the compound and the oil-based base are mixed by heating, and then water is added and mixed to emulsify the mixture. In the case of lotion-type cosmetics, water is added to an alcoholic solution of the compound and an oily base while stirring, or in the case of cosmetics such as shampoo, the compound is The IQ-so materials of the present invention can be easily produced by applying known techniques such as heating and uniformly dispersing the ingredients and other raw materials. Examples will be described below.
Parts shown in the examples mean parts by weight, and % means % by weight. Example 1 (Oily skin cream) y-(N-1,1-dimethylolethyl)amino. Mix 3 parts of propylene glycol Q1n-9-octadecenyl ether, 1.5 parts of paraffin, 4 parts of vaseline, 1.5 parts of Millo, and 15 parts of liquid paraffin and heat at 760 for 5 minutes. to ensure uniform dissolution.

Next, 7 parts of purified water overflowing with 75 qo was added thereto while stirring, and after the addition, the mixture was cooled to room temperature while continuing to stir, to obtain an oil-based skin cream (nutritional cream). The cream obtained here has an extremely good texture and a gloss level of 83.
(according to JIS Z8741-1962 Fertility Measurement Method 2), and the daily stability at 45oo is also 6.
It remained stable for over several months. Example 2 (hydrophilic skin milk) (oil phase) y-(N-1,1-dimethylolethyl)aminopropyresoglycol Q-octadecyl ether 1 part N-2-hydroxy-3-(2-octyldode Siloxy) propylglucosamine 1 part liquid paraffin 8 parts palmityl palmitate 5 parts olive oil
8 parts stearic acid
2 parts cholesterin 2 parts fragrance Appropriate amount (water phase)
Pure water 73.5 parts Potassium hydroxide 0.05 parts The oil phase components in the above proportions were mixed uniformly at 80°C, and then added to the mixture at 80°C.
Gradually add the aqueous phase and emulsify.

Thereafter, the mixture was cooled to room temperature while continuing to stir, and hydrophilic skin milk was obtained. The milk thus obtained is 10 qo
, the viscosity at 20°C and 40°C is 650 pS and 60, respectively.
The viscosity change due to temperature was very small at 0 specific ps and 550 specific ps, and the usability was also excellent. Moreover, this product was extremely stable even after 6 months at 45°C. Example 3 (oily foundation cream) r-(N-trimethylolmethyl)aminopropylene glycol on-9 3-part-octadecenyl ether y-(N-1,1-dimethy.

aminopropylene glycol Q- docosyl ether 2 parts solid paraffin 2 parts vaseline
3 parts liquid paraffin
15 parts fragrance
Appropriate amount (water phase) 4 parts glycerol titanium oxide 1.5 parts kaolin 1.5 parts pengara 0.02 parts yellow iron oxide 0.02 parts water
65 parts The oil phase components having the above composition are uniformly dispersed in 8 parts.

Meanwhile, the aqueous phase components were similarly dispersed uniformly at 80 pm. Next, the aqueous phase was added to the oil phase and emulsified, and then gradually cooled to room temperature to obtain a foundation cream. Is this one also 4? In saving in C, 6
It was found that the foundation was extremely stable even after several months, and was also confirmed to be a foundation that is extremely unlikely to cause a change in name change. Example 4 (Skin lotion) (Base 1) Glycerin 3 parts Propylene glycol 1 part Sorbitol 1 part Pure water 8 side pigment
Appropriate amount (base 2) ethanol (95%) 15 parts y-(N-
2,3,4,5,6-pentahydroxy)aminopropylene glycol n-9-octadecenyloxy ester 0. Sakube Kaori
Ingredients Appropriate amounts of Base 1 and Base 2 having the above composition were thoroughly mixed at room temperature to obtain a skin lotion.

The lotion obtained here exhibits a remarkable moisturizing effect on dry skin, and the y-(N-2,3,4,5,
It has been found that 6-bentahydroxyhexyl)aminopropylene glycol Q-n-9-octadecenyloxy ether is also effective as a wetting agent. Example 5 (Nutritional oil) (Base 1) Lanolin 8 parts Olive oil 12 parts Vaseline 5 parts Liquid paraffin
4.5 parts oil-soluble vitamins
1.5 parts diisopropyl adibate
15 parts (base 2)? -(N-trimethylolmethyl)aminopropylene glycol o-2-octyl 2 parts Rudecyl ether r-(N-1,1-dimethylolethyl)aminopropylene glycol o-decyl 1.5 parts Ether Water-soluble vitamins 1 1 part propylene glycol 2.5 parts fragrance
Appropriate amount of base 2 ingredients 50
00 is enough to dissolve it.

Also, the components of Base 1 are melted at room temperature. Next, Base 1 was gradually added to Base 2 while stirring at a temperature of 3 mm or less, and thoroughly mixed to obtain a nutritive oil. As described above, by using the surfactant of the present invention, the main pot is a component that is a water-based substance and hardly dissolves in oils. It has been found that it is an extremely useful surfactant that can also solubilize water-soluble vitamins and propylene glycol in oils. In addition, the nutritive oil obtained here was highly penetrating and remained extremely stable even after 6 months at 45°C without separating water-soluble vitamins and propylene glycol.

Example 6 (Oily hair cream) (Oil phase) N-2-Hydroxy-3-n-octadecyloxypropylglucosaminiso 1 part y1 (N-
1,1-dimethylolethyl)aminopropylene glycol Q-n-9 octadecenyl ether 3 parts liquid paraffin 15 parts Millow
2.5 parts solid paraffin
2.5 parts Vaseline
35 parts fragrance
Appropriate amount (aqueous phase) glycerin
3 parts thickener 1.5 parts pure
65 parts of water The oil phase and aqueous phase having the above composition were heated separately to 70 qo,
Dissolve uniformly.

Next, the aqueous phase was gradually added into the oil phase while stirring vigorously, and after the addition, the mixture was cooled to overflowing the room while continuing to stir, to obtain an oil-based hair cream. When the cream thus obtained was applied to the hair, it did not give any unpleasant or strange feeling such as stickiness, and its setting power lasted for 3 to 4 days. Example 7 (Liquid hair styling agent) y-(N-trimethylolmethyl)aminopropylene glycol Q-12-hydroxy-n-9-octadecenyl ether 2 parts Polyoxyethylene polyoxypropylene copolymer 13 parts Ethanol (95 %) 5 Soto Jun Water
35 parts fragrance
Appropriate amounts of each component of the above composition were thoroughly mixed and dissolved at room temperature to obtain a liquid hair styling agent.

This product had less stickiness and good setting power. Example 8 (Shampoo) Potassium laurate 15 parts Sodium lauryl P. 0. E sulfate 2 parts Jetyl Sepacate 1 part y-(N-2,3,4,
5,6-pentahydroxy)amino/propylene glycol Q dodecyl ether 5 parts y-(N-trimethylolmethyl) aminopropylene glycol q-octadecyl ether 5. $be Jun
Water 65 parts Flavoring
Heat appropriate amounts of each component of the above composition to 5 pico C to dissolve it uniformly, and then cool it to room temperature under a rope to create a shampoo with excellent detergency and ultra-foaming power.
Furthermore, after washing the hair, it gave good shine and suppleness without giving a squeaky feeling to the hair.

Example 9 (Milk hair rinse) y-(N-methylolmethyl)aminopropylene glycol is dodecyl ether 0.5 part N-
2-hydroxy-3-hexadecyloxypropylgalactosamine 0.4 parts laurylbenzyltrimethylammonium chloride 4 parts propylene glycol 3 parts cetanol
3 parts pure water 87 parts fragrance
Appropriate amounts of each component of the above composition are heated at 50 qo and uniformly dispersed.

Thereafter, the mixture was cooled to room temperature while being further stirred in a candle, and a milky lotion-like rinse was obtained. It has been found that this product provides good moisture, shine, and suppleness to hair, and has various properties that could not be expected from conventional surfactants. Example 1
0 (Daily emulsion stability of oil-based cream) In the above Example 1, y-(N,-1,1-dimethylolethyl)aminopropylene glycol Q-n-9
- Instead of ocdadecenyl ether, another compound of the invention, y-(N-trimethylolmethyl)aminopropylene glycol Q-tetradecyl ether (M.1(
, y-(N-1,1-dimethylolethyl)aminopropylene glycol Q-docosyl ether (M.2), y
-(N-1,1-dimethylolethyl)aminopropylene glycol Q-decyl ether (M.3), y-(N
(monotrimethylolmethyl) aminopropylene glycol Q12-octyldodecyl ester
N-trimethylolmethyl)aminopropylene glycol Q-2-(1,3,3,trimethyl)butyl-5,7
, 7-trimethyloctyl ether (LOL.5), and the known y-(N-2-hydroxyethyl)aminopropylene glycol Q-decyl ether (M.6), polyoxyethylene stearyl ether (3.E.D.) (modified 7)
Creams were prepared using stearic acid jetanolamide (M.8), respectively, and the emulsion stability over time was investigated in an Enoki greenhouse maintained at 45 qo.

The results are shown in Table 2. As is clear from the results in Table 2 and above, the IQ salmon material of the present invention (1-
5) was significantly superior to conventional products in terms of emulsion stability over time, and also had good appearance, gloss, and feel.

Example 11 (Shampoo foaming power, hair dynamic friction force, eye mucous membrane irritation) As a nonionic surfactant, the y-
(N-1,1-dimethylolmethyl)aminopropylene glycol Q-decyl ether (Snake.1), y-(N-
trimethylolmethyl)aminopropylene glycol Q
Dodecyl ether (Snake.2), N-2-hydroxy-3-docosyloxypropylglucosamine (Snake.3), y
-(N-2,3,4,5,6-bentahydroxyhexyl)aminopropylene glycol Q-2-octyldodecyl ether (M.4), N-2-hydroxy-3-(
12-Hydroxy-N-9-octadecelonyloxy)propylgalactosamine (Length 5) and commercially available lauric acid jetanolamide (M.6), stearic acid monoethanolamide (Length 7), y-(N- 2-Hydroxyethyl) aminopropylene glycol Q-decyl
M. A shampoo having the following composition was prepared according to Example 8 using each of the above shampoos and was used as a test sample.

(Composition) Nonionic surfactant...5 parts Potassium laurate...2 parts cetylpyridinium bromide...0.5 part cetanol
...0.8 part ethanol (95%
) …6 parts pure water
…65 parts fragrance
...Appropriate amount (test method) 1 Prepare a solution by diluting 100% of the super foaming force sample with water,
Using a Ross Miles super foam strength tester, the foam was poured at 40 qo, and the height of the foam after one rat sand was measured.

2. Hair friction coefficient Soak human hair in a 0.1% aqueous solution of each sample for 3 minutes, then wash under running water and dry.

After leaving this hair at 20°C and 65% relative humidity for 2 hours, it was measured using the radar method at a friction speed of 2 M/min and a load of 500.
Measurements were made under 9 conditions. 3. Animal eye mucosal irritation test was conducted using albino cats.

0.1 instillation of the sample into one eye, and the other eye serves as a control.

Observations will be made for 1, 2, 3, 4, and 7 days after treatment, and if the disorder continues, the treatment will be continued. The degree of disability is multiplied by a factor depending on the magnitude of the effect on visual impairment. The judgment criteria are as follows. 'i} Degree of corneal clouding Score - Transparent 0 Details of the iris cannot be seen through the opaque area, but the pupil can be distinguished 3 Neither the iris nor the pupil can be distinguished 4'.

'Area of cloudy area Score - No cloudy area 01/bottom of Buddha
11/4-1/2
21/2-3/4
33/French

(Judgment criteria) 0-0.5 Non-irritating 1.5-2.5 Almost no stimulation 2.5-15 Very mild irritation The above results are shown in Table 3.

Table 3 Also, human hair was added to 0.1% aqueous solution of samples '1} to '7}.
After soaking for a minute, rinse under running water, then immerse in 0.1% penzalkonium chloride solution, rinse, and then rinse under running water.
After being left for 2 hours under conditions of 0qC and 65% relative humidity, the hair bed friction coefficient was measured by the radar method under the conditions of a friction rate of 2 units/min and a load of 500 o.

The results are shown in Table 4. From the results in Table 4 and above, the compounds of the present invention (No. 1 to No. 4)
) is a shampoo base with superior foaming properties (foaming) compared to commercially available surfactants (Fune.5 to Fune.7), and also has a small hair dynamic friction coefficient even before use as a rinse, and also has a rinsing effect. It is an ideal shampoo and conditioner base.

As described above, the shampoo of the present invention has excellent foaming power compared to shampoos using other related surfactants.
It is also found that the hair dynamic friction coefficient is small, has a rinsing effect, and causes less irritation to the eye mucous membranes.

Example 12 (Pigment dispersibility in liquid makeup) Y-(N-1 of the present invention) as a surfactant (emulsifying dispersant)
, 1-dimethylolethyl) aminop.

Pyrene glycol Q-2-(1,3,3-trimethyl)
Butyl-5,7,7-trimethyloctyl ether (No. 1), y-(N-1,1-dimethylolethyl) aminopropylene glycol Q-n-9-octadecenyl ether (No. 2), y -(N-trimethylolmethyl)aminopropylene glycol Q-2-octyl dodecyl ether (M.3), y-(N-trimethylolmethyl)aminopropylene glycol Q docosyl ether (M.4) and commercially available sorbitan Monostearate (rudder.5), y-(N-2-hydroxyethyl)aminopropylene glycol Q-octadecyl-7yl (shame.6)
Each liquid make-up composition was prepared as described below, and its dispersibility with respect to titanium oxide was examined. (Oil phase) Surfactant 3 parts liquid paraffin 35 parts cetanol
5 parts castor oil
5 parts isopropyl palmitate 2 parts fragrance
Appropriate amount (aqueous phase) titanium oxide
2 parts pure water
5. The details of the iris can be seen through the opaque side. 1. The details of the iris are slightly unclear through the opaque part. 2. Add the above oil phase component to 8 to 0, and dissolve it uniformly while stirring vigorously.

Similarly, the aqueous phase components are uniformly dispersed. Next, the aqueous phase is added to the oil phase at the same temperature and dispersed uniformly, and then cooled to room temperature while being held in a candle. 6) was obtained. Next, 10 of each sample was placed in 20 centrifuge tubes and subjected to thermal centrifugation (45℃, 150℃).
After carrying out the ratio (pml and min.), accurately weigh out approximately 1.0 μm of the upper layer liquid and place it in a Lupo tube. The crucible was heated on a burner until it reached a constant weight (approximately 1 hour) to completely incinerate the contents, and the titanium oxide content was quantified in this range (Cosmetic Raw Materials Standard Commentary, 1st Edition). The dispersion power (based on the volumetric quantitative method) of titanium oxide was compared. The results are shown in Table 5.
In addition, in the table, sorbitan monostearate (Beverage M.5
) is expressed as a converted value when the value is set as 100. As shown in Table 5, it can be seen that the surfactant of the present invention is significantly superior in pigment dispersibility compared to existing similar compounds.

Also, almost similar results were obtained in tests using other pigments such as kaolin, talc, ultramarine blue, and carbon black. Example 13 (Hiding power of oil-based foundation cream) As a surfactant, y-(N-2,3,4,5,6-pentahydroxyaminopropylene glycol Q-decyl ether (M.1), N- 2-hydroxy-3-(12-hydroxy-9-octadecenyloxy)propylgalactosamine (shame.2), y-(N-1,1-dimethylolethyl)aminopropylene glycol Q-n-9-octadecenyl ether .3), y-(N-trimethylolmethyl)aminopropylene glycol'Q-docosyl ether (M.4), and commercially available sorbitan sesquistearate (M.5), oleic acid diisopropanolamide (M.6), y-(N-2-hydroxyethyl)aminopropylene glycol Q docosyl ether (M.
A foundation cream having the following composition was prepared according to Example 3 using each of 7).

(Oil phase) Surfactant 5 parts Vaseline
2.5 Part Karnaparou
1.5 parts lanolin
1.5 parts liquid paraffin 1
5 parts Flavor Appropriate amount (aqueous phase) 1,3-butanediol 3 parts titanium oxide 2 parts kaolin
1.5 part pengara
0.02 part yellow iron oxide
0.02 Miyako Jun Water
65 parts (Measurement method) Thickness 0.5
It was measured by the Ando force measurement method (JISK5101-19 ridge) using a cryptometer equipped with a thin steel plate for the fence.

The results are shown in Table 6. The values shown in the table are converted values based on the value obtained when sorbitan sesquibehenate is used (sample ship .5) as 100. Table 6 Example 14 (Shampoo) Example 1 except that in place of the compound of the present invention used in Example 8, the following compounds of the present invention (M.1 to No. 5) were used in each base part. A shampoo was produced in the same manner as in Example 8.

All of the shampoos obtained had excellent detergency and foaming power, and gave good shine and suppleness to the hair after washing without giving the hair a squeaky feel. M. Compound of the present invention [1'. y-(N-1,1-dimethylolethyl)aminopropylene glycol Q-dodecyl ether/Sh[2] y-(N-trimethylolmethyl)aminopropylene glycol Q-dodecyl ether/Sh{3, y-(N-2) ,3,4,5,6-pentahydroxyl)aminopropylene glycol Q-dodecyl ether

Claims (1)

[Claims] 1 General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, R_1 is n-decyl group, n-dodecyl group,
n-tetradecyl group, n-hexadecyl group, 2-hexadecyl group, 2-hexyldecyl group, n-octadecyl group, 2-heptylundecyl group, 2-(1,3,3-trimethyl)-butyl-5,7 , 7-trimethyloctyl group, n-9-octadecenyl group, 12-hydroxy-n-
Octadecyl group, 12-hydroxy-n-9-octadecenyl group, 2-octyldodecyl group, n-docosyl group,
R_2 is ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or ▲There are mathematical formulas, chemical formulas, tables, etc.▼. ) A cosmetic containing at least one of the compounds represented by: