JP2001039937A - Composition for external preparation - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject composition having excellently preventing and improving effect on chapped skin, bettering effect on hair touch, etc. by making the composition include a specific amide derivative. SOLUTION: This composition comprises an amide derivative of the formula (R1 is a 1-39C hydrocarbon; R2 is a 1-12C bifunctional hydrocarbon; R3 is a 2-12C bifunctional hydrocarbon; and R4 is a 2-6C hydroxyalkyl). The composition is obtained by reacting a compound containing two eliminable groups with preferably >=2 equivalent amine by heating preferably at 40-100 deg.C to give an intermediate and reacting the intermediate with a carboxylic acid halide (e.g. a carboxylic acid chloride, etc.), preferably in the presence of a base except the intermediate in a mixed solvent of water and an organic solvent at pH 9-14 to give the amide derivative. The amount of the amide derivative formulated in the composition is preferably 0.001-50 wt.% based on the total composition in the case of an emulsion type external preparation for skin and a skin cosmetic.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an external preparation composition which enhances the moisture retention of the stratum corneum, and has an excellent effect of improving rough skin and protecting hair, and a novel amide derivative having such an effect.

[0002]

2. Description of the Related Art Conventionally, to improve or prevent rough skin, free amino acids, organic acids,
Cosmetics containing a water-soluble component contained in the stratum corneum, such as urea or inorganic ions, or a highly hydrophilic moisturizing substance have been used. However, such water-soluble components and moisturizing substances cannot be said to essentially prevent and treat rough skin, and their moisturizing effects are also temporary. On the other hand, application of natural ceramide, which is an intercellular lipid of the stratum corneum, to the skin has been studied for the purpose of improving the water retention ability, but it is expensive, and also has a low compoundability and formulation stability in external preparations. There was a problem that it was not desirable.

In view of such circumstances, the present inventors have found that some amide derivatives have an effect of fundamentally improving the water retention ability of the stratum corneum, and an effect of penetrating hair to enhance its protective effect. Found that there is
No. 34, JP-A-64-29347, JP-A-Hei-8
JP-A-319263 and JP-A-64-9913).

[0004] However, it has been difficult to keep the compoundability and compounding stability of such an amide derivative in the case of compounding it as an external preparation. In addition, in terms of production, there is also a problem that a multi-stage reaction is required, which is not economically preferable.

[0005]

Accordingly, the present invention has the effect of essentially improving (maintaining / reinforcing) the water retention ability of the stratum corneum by applying it to the skin, and also has the compoundability and compounding stability. Amide derivatives that can be produced more efficiently and inexpensively and contain them to prevent rough skin and inflammation.
It is an object of the present invention to provide an external preparation composition that has an improving effect, further penetrates into hair, enhances its protective effect, improves the feel of hair, and has the effect of preventing and improving roughening of the scalp.

[0006]

The inventor of the present invention has found that the amide derivative represented by the following general formula (1) can unexpectedly substantially improve the water retention ability of the stratum corneum, It has been found that the composition is excellent in manufacturability, and that when it is added, an external preparation composition excellent in the effect of preventing and improving the rough skin, the effect of improving the hair feel, and the like can be obtained.

The present invention provides the following general formula (1)

[0008]

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[0009] (wherein, two R ¹ are the same or hydroxy group may be substituted or different, represents a linear or branched hydrocarbon group having 1 to 39 carbon atoms, R ² is A hydroxy group may be substituted, and represents a linear or branched divalent hydrocarbon group having 1 to 12 carbon atoms, and R ³ has 2 to 2 carbon atoms.
It represents a linear or branched divalent hydrocarbon group having 12, R ⁴
Represents a linear or branched hydroxyalkyl group having 2 to 6 carbon atoms. The present invention provides an external preparation composition containing the amide derivative represented by the formula (1).

The present invention also provides the following general formula (2)

[0011]

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Wherein two R ^1-a are the same or different and each represents a straight-chain or branched-chain alkyl group having 13 to 17 carbon atoms.

[0013]

BEST MODE FOR CARRYING OUT THE INVENTION In the amide derivative (1), 2
R ¹ may be the same or different and may be a straight-chain or branched-chain saturated or unsaturated hydrocarbon group having 9 to 21 carbon atoms, particularly a straight-chain or branched-chain alkyl or alkenyl group having 9 to 21 carbon atoms. Is preferred. Of these, nonyl group, tridecyl group,
A pentadecyl group, a heptadecyl group, a nonadecyl group, a heneicosyl group, a 1-heptyldecyl group, an isoheptadecyl group, a methyl-branched isoheptadecyl group, an 8-heptadecenyl group, a 8,11-heptadecadienyl group are more preferable, and a tridecyl group, a pentadecyl group, a heptadecyl group are preferable. Group,
Nonadecyl group, 1-heptyldecyl group and methyl-branched isoheptadecyl group are particularly preferred, tridecyl group, pentadecyl group, heptadecyl group and methyl-branched isoheptadecyl group are more preferred, and pentadecyl group and heptadecyl group are most preferred. R ² is preferably a linear or branched alkylene group having 1 to 6 carbon atoms or a 2-hydroxytrimethylene group. Among them, methylene group, ethylene group, trimethylene group, tetramethylene group, pentamethylene group, hexamethylene group, 1-methylethylene group, 1-methylethylene group,
Methyltrimethylene group, 2-methyltrimethylene group, 1
-Ethylethylene group and 2-hydroxytrimethylene group are more preferable, ethylene group, trimethylene group and 1-methylethylene group are particularly preferable, and ethylene group is most preferable.

R ³ is preferably a linear or branched alkylene group having 2 to 6 carbon atoms. Among them, ethylene group, trimethylene group, tetramethylene group, pentamethylene group, hexamethylene group, 1-methylethylene group, 2-methylethylene group, 1-methyltrimethylene group, 2-methyltrimethylene group, 1,1 -Dimethylethylene group and 2-ethyltrimethylene group are more preferred, ethylene group, trimethylene group, 1-methylethylene group and 2-methylethylene group are particularly preferred, and ethylene group is most preferred. R ⁴ is
A linear or branched hydroxyalkyl group having 2 to 3 carbon atoms is preferred. Among them, 2-hydroxyethyl group, 1-
A methyl-2-hydroxyethyl group, a 2-methyl-2-hydroxyethyl group, a 2-hydroxypropyl group, and a 3-hydroxypropyl group are more preferable, and a 2-hydroxyethyl group, a 1-methyl-2-hydroxyethyl group, A -methyl-2-hydroxyethyl group is particularly preferred, and a 2-hydroxyethyl group is most preferred.

In the amide derivative (1) of the present invention, a particularly preferred compound is a compound obtained by combining the above-mentioned particularly preferred groups for R ^{1 to} R ^{4 in} the general formula (1), and the most preferred compound is Compounds (1a), (1b) and (1c) combining the most preferred groups of R ^{1 to} R ⁴
It is.

[0016]

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The compounds (1a), (1b) and (1c)
Is extremely excellent in the water retention ability of the stratum corneum, the effect of improving skin roughness, the effect of protecting hair, and the like, and is also extremely excellent in mixability, manufacturability, and the like.

In the amide derivative (2), two R
^1-a may be the same or different and is preferably a tridecyl group, a pentadecyl group, a heptadecyl group or a methyl-branched isoheptadecyl group, and particularly preferably a pentadecyl group or a heptadecyl group.

The amide derivative (1) of the present invention can be obtained, for example, by the following production method.

[0020]

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(Wherein, R ¹ , R ² , R ³ and R ⁴ have the same meanings as described above, and X represents a leaving group such as a halogen atom, a mesylate group or a tosylate group, and preferably a chlorine atom Or a bromine atom, and Y represents a halogen atom,
Preferably it is a chlorine atom. )

That is, the intermediate (5) is obtained by reacting the compound (3) having two leaving groups with the amine (4). In this reaction, the amine (4) is preferably used in excess relative to the compound (3), that is, at least 2 equivalents, in order to secure a yield and suppress the generation of by-products. It is preferable to carry out the reaction by heating to a lower temperature in view of the reaction time and the yield. The obtained intermediate (5) can be purified by a known method such as distillation or powder treatment, but can be used in the next reaction step without purification.

The amide derivative (1) can be obtained by reacting the intermediate (5) obtained as described above with the carboxylic acid halide (6). This reaction is preferably performed in the presence of a base other than the intermediate (5).
In this reaction, hydrogen halide is by-produced, and unless a base other than the intermediate (5) is added, the by-produced hydrogen halide is converted to the intermediate (5) or a monoamidated compound which is an intermediate of the present reaction with a salt. Is formed, and it is difficult to react with the carboxylic acid halide. As a result, the amide derivative (1) cannot be obtained sufficiently efficiently. Further, the reaction is preferably performed in a mixed solvent of water and an organic solvent within a pH range of 9 to 14. When only an organic solvent is used as a reaction solvent,
The reaction (esterification) of the carboxylic acid halide with the hydroxyl group proceeds more than when a mixed solvent of water and an organic solvent is used, and the selectivity and the yield of the amide derivative (1) are apt to be reduced. On the other hand, if only water is used as the reaction solvent, the product is difficult to dissolve in water.Therefore, there is a problem that a large amount of water must be used. Of by-products tends to increase. The pH of the reaction solution also has a significant effect on the by-product of carboxylic acid, and even when a mixed solvent of water and an organic solvent is used, if the reaction is performed at a pH lower than 9, carboxylic acid and esterified products are increased, so that the pH is lowered. It is preferable to control in the range of 9 to 14.
For the above reasons, the most preferable reaction condition is that the intermediate (5) is dissolved in a mixed solvent of water and an organic solvent, and the pH is adjusted by adding a base other than the intermediate (5) as needed.
Is a condition in which the carboxylic acid halide (6) is added while maintaining the range of 9 to 14.

The organic solvent has good compatibility with water,
In addition, a polar solvent in which a mixed solvent with water dissolves the intermediate (5) and a monoamidated compound which is an intermediate of the present reaction is preferable, and specifically, methanol, ethanol, propanol, 2-propanol, butanol, tert-butyl alcohol Alcohols such as (2-methyl-2-propanol), polyhydric alcohols such as propylene glycol, alkoxy alcohols such as methyl cellosolve, acetone,
Ketones such as methyl ethyl ketone, tetrahydrofuran,
Furfuryl alcohol and dioxane are preferred examples. Examples of the base include alkali metal hydroxides such as potassium hydroxide and sodium hydroxide, alkaline earth metal hydroxides such as calcium hydroxide, alkali metal carbonates such as potassium carbonate, and alkaline earth metal carbonates such as calcium carbonate. Salts, alkali metal alcoholates such as sodium methoxide, sodium ethoxide, potassium tert-butoxide and the like, and amines such as triethylamine and pyridine are preferable, and potassium hydroxide, sodium hydroxide and triethylamine are preferable. It is most preferable to use these aqueous solutions. As the carboxylic acid halide (6), in addition to a carboxylic acid halide having a single composition, a mixed fatty acid halide such as a coconut oil fatty acid halide and a tallow fatty acid halide can be used, and a carboxylic acid chloride is preferable. The carboxylic acid halide (6) can be used either undistilled or distilled.

The amide derivative (1) thus obtained can be purified by a known method such as washing with water, column chromatography, distillation, crystallization, recrystallization and powder treatment. In addition, treatment under basic conditions can be performed for the purpose of removing by-product esterified products or carboxylic acids.

The amide derivative (1) of the present invention thus obtained penetrates into the lipid membrane between keratinocytes and improves (maintains / reinforces) the water retention ability of the horny layer.
Exhibits the effect of improving skin roughness. It also penetrates the hair and enhances its protective effect.

The external preparation composition of the present invention comprises an amide derivative (1) in a base (carrier) usually used for external preparations, and can be produced according to a conventional method by mixing the respective raw materials.

The external preparation composition of the present invention is roughly classified into a medicated skin external preparation and a cosmetic in its use form. Examples of the medicated skin external preparation include various ointments containing a pharmaceutically active ingredient. The ointment may be any of those based on an oily base and those based on an oil-in-water or water-in-oil emulsion base. The oil base is not particularly limited, and includes, for example, vegetable oil, animal oil, synthetic oil, fatty acid, and natural or synthetic glyceride. The medicinal component is not particularly limited, and includes, for example, an analgesic anti-inflammatory, an antipruritic, a bactericidal disinfectant, an astringent, an emollient,
Hormones and the like can be used as needed.

When used as a cosmetic, in addition to the amide derivative (1), which is an essential component, oils, surfactants, humectants, ultraviolet absorbers, and whitening agents generally used as cosmetic components And wrinkle improvers, alcohols, chelating agents, pH adjusters, preservatives, antioxidants, thickeners, pigments, fragrances and the like can be arbitrarily combined.

As cosmetics, there are various forms, for example, water-in-oil type or oil-in-water type emulsified cosmetics, creams, cosmetic emulsions, lotions, oily cosmetics, lipsticks, foundations, bath agents, skin cleansers, and the like. Skin cosmetics, and hair cosmetics such as hair tonic, hair styling, hair rinse, hair treatment, hair conditioner, hair styling agent, shampoo, hair restorer and hair restorer.

The compounding amount of the amide derivative (1) in the external preparation composition of the present invention is not particularly limited, but usually, in the case of emulsified skin external preparations and skin cosmetics, 0.001 to 0.001 of the total composition. It is preferably 50% by weight (hereinafter simply referred to as%). In the case of an oily skin external preparation or skin cosmetic based on a liquid hydrocarbon such as squalane, 0.0% of the total composition is used.
The content is preferably 1 to 50%, and particularly preferably 0.01 to 20% in each case. In particular, it is preferable to add 0.1 to 20% for prevention and improvement of rough skin and inflammation.

The amount of the amide derivative (1) to be added to hair cosmetics is not particularly limited, but is 0.001 to 5% for shampoos, etc.,
0.1 for conditioners, styling agents, etc.
-20%, and in hair liquids, hair tonics, etc., it is preferable to add about 0.01-5%.

In the composition for external use of the present invention, a surfactant such as a nonionic surfactant, an anionic surfactant, a cationic surfactant, an amphoteric surfactant and the like are blended with the medicated skin external preparation and skin cosmetics. it can. Of these, nonionic surfactants such as fatty acid monoglyceride, polyoxyethylene alkyl ether, and polyoxyethylene alkyl phenyl ether are particularly preferred. The compounding amount is 0.1% in the composition.
It is preferably from 01 to 20%, particularly preferably from 0.1 to 5%.

In the external preparation composition of the present invention, hair cosmetics include surfactants such as anionic surfactants, cationic surfactants, nonionic surfactants and amphoteric surfactants, and other hair cosmetics. The components used can be blended. When the hair cosmetic of the present invention is a shampoo, an anionic surfactant such as an alkyl ether sulfate, an alkyl sulfate, or an olefin sulfonate can be blended as a main activator.
The compounding amount is 5 to 30%, particularly 10 to 20% in the composition.
Is preferred.

When the cosmetic of the present invention is a hair rinse, conditioner, hair treatment, or hair styling agent, a cationic surfactant such as a mono- or di-long-chain alkyl quaternary ammonium salt is used to impart a good feel to the hair. , A nonionic surfactant such as polyoxyethylene alkyl or alkenyl ether, and an oil or fat such as liquid paraffin. The compounding amount of the cationic and nonionic surfactant is 0.1 to 50% in the composition, particularly 0.5 to 2%.
0% is preferred.

Further, when the hair cosmetic is a hair liquid, a hair tonic or the like, a nonionic surfactant such as polyoxyethylene can be used in combination. Nonionic surfactants are
It is preferable to add 0.01 to 20%, particularly 0.1 to 5% of the total composition.

The skin cosmetic and hair cosmetic containing the amide derivative (1) can be in the form of an aqueous solution, ethanol solution, emulsion, suspension, gel, solid, aerosol, powder or the like. Absent.

[0038]

EFFECT OF THE INVENTION The amide derivative (1) penetrates into the lipid membrane between keratinocytes and improves (maintains / reinforces) the water retention capacity of the horny layer, thereby preventing and treating rough skin and inflammation, Prevent aging. In addition, it can penetrate into the hair to enhance its protective effect, improve the feel of the hair, and prevent and improve roughening of the scalp. In addition, the composition for external use can be produced efficiently and inexpensively with good solubility in the base, excellent blending stability and the like.

[0039]

EXAMPLES The melting point was measured in accordance with the first method of measuring the melting point of the general test method for cosmetic raw material standards (second edition), and the temperature at which the sample was liquefied and no solid was observed at all was taken as the melting point.

Example 1 (1) Production of Intermediate (5a)

[0041]

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In the flask, diglycolamine (2-
(2-Aminoethoxy) ethanol) was charged with 2550 g, heated to 60 ° C., and then 302 g of 1,2-dichloroethane.
Was added dropwise at 60 ° C. over 3 hours. 6 at 60 ° C
After stirring for an hour, the mixture was cooled to 40 ° C., and 360 g of 96% potassium hydroxide was added. Then, after stirring at 40 ° C. for 2 hours, the resulting solid was separated by filtration. Ethanol and unreacted diglycolamine were distilled off from the filtrate under reduced pressure to obtain a yellow liquid. The liquid was subjected to molecular distillation (10 Pa, 140 ° C.) to obtain 495 g (yield: 69%) of the intermediate (5a). Properties: pale yellow liquid ¹ H-NMR (CDCl ₃ , δ); 2.77 (s, 4H), 2.81 (t, J = 5.1 Hz, 4H),
3.51 (br s, 4H), 3.53-3.75 (m, 12H).

(2) Production of amide derivative (1a) 18.9 of the intermediate (5a) produced in (1) was placed in a flask.
g, toluene 285 g and triethylamine 24.3 g were charged and mixed with stirring. Here, 44.0 g of palmitic acid chloride was added dropwise at 30 ° C. over 1 hour. After further stirring at 30 ° C. for 1 hour, the solvent was distilled off under reduced pressure. The resulting reaction mixture was purified by silica gel chromatography (chloroform: methanol = 50: 1) to purify the amide derivative (1a) (36.8 g, yield 65%) and further monoesterified compound (7a) (4.2 g). Yield 5.5%), bis-esterified compound (8a) 3.8
g (yield 4.0%) was obtained. The yield and yield are shown in Table 1.

[0044]

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[0045]

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Amide derivative (1a) Property: white crystal Melting point: 86.3 ° C. ¹ H-NMR (CDCl ₃ , δ); 0.88 (t, J = 6.7 Hz, 6H), 1.25 (s, 48H),
1.51-1.82 (br s, 4H), 2.31 (t, J = 8.0Hz, 4H), 3.50-3.80
○ Monoesterified compound (7a) Property: White crystal Melting point: 63.8 ° C. ¹ H-NMR (CDCl ₃ , δ); 0.88 (t, J = 6.8 Hz, 9H), 1.25 (s) , 72H),
1.49-1.71 (br s, 6H), 2.24-2.42 (m, 6H), 3.43-3.79 (m, 1
8H), 4.15-4.25 (m, 2H). Bisesterified compound (8a) Property: White crystal Melting point: 67.5 ° C. ¹ H-NMR (CDCl ₃ , δ); 0.88 (t, J = 6.7 Hz, 12H), 1.25 (s, 96
H), 1.51-1.70 (br s, 8H), 2.24-2.43 (m, 8H), 3.40-3.67
(m, 16H), 4.18 (t, J = 4.8Hz, 4H).

Example 2 Production of amide derivative (1a) The same operation as in Example 1 was carried out except that 171 g of THF was used instead of toluene. The yield and yield are shown in Table 1.

Example 3 Preparation of Amide Derivative (1a) The same operation as in Example 1 was carried out except that 171 g of tert-butyl alcohol (2-methyl-2-propanol) was used instead of toluene. The yield and yield are shown in Table 1.

Example 4 Preparation of amide derivative (1a) In Example 1, 114 g of triethylamine was used instead of toluene.
(A total of 138 g of triethylamine) was used. The yield and yield are shown in Table 1.

Example 5 Preparation of Amide Derivative (1a) The intermediate (5) prepared in Example 1 (1) was placed in a flask.
a) 18.9 g, 57.1 g of isopropanol and 5 parts of water
7.1 g was charged and mixed by stirring. Here, 44.0 g of palmitic acid chloride and 13.3 g of a 48% aqueous sodium hydroxide solution were added at 30 ° C. to adjust the pH of the reaction solution from 9.5 to 1
It dripped over 1 hour, adjusting so that it might be maintained at 2.5. After further stirring at 30 ° C. for 1 hour, the solvent was distilled off under reduced pressure. The obtained reaction mixture was purified by silica gel chromatography (chloroform: methanol = 50: 1). Table 1 shows the yields and yields of Examples 1 to 5. From Table 1, it can be seen that Examples 1 to 5 show that each of the compounds (1a) is efficiently used.
It is clear that the method of Example 5 is particularly preferable.

[0051]

[Table 1]

Example 6 Preparation of Amide Derivative (1a) The intermediate (5) prepared in (1) of Example 1 was placed in a flask.
a) 18.9 g, 57.1 g of isopropanol and 5 parts of water
7.1 g was charged and mixed by stirring. Here, 44.0 g of palmitic acid chloride and 13.3 g of a 48% aqueous sodium hydroxide solution were added at 30 ° C. to adjust the pH of the reaction solution from 9.5 to 1
It dripped over 1 hour, adjusting so that it might be maintained at 2.5. After further stirring at 30 ° C. for 1 hour, the temperature was raised to 60 ° C., 2.7 g of a 48% aqueous sodium hydroxide solution was added, and the mixture was stirred at 60 ° C. for 1.5 hours. To the obtained reaction mixture, 286 g of toluene was added and extracted. After washing the toluene solution with water, it was recrystallized from a mixed solution of toluene and isopropanol to give 46.3 g of the amide derivative (1a) (81% yield).
I got

Example 7 Preparation of Amide Derivative (1b) The same operation as in Example 6 was repeated except that 48.5 g of stearic acid chloride was used instead of palmitic acid chloride. 83%)
I got Properties: White crystal Melting point: 91.5 ° C ¹ H-NMR (CDCl ₃ , δ); 0.88 (t, J = 6.7 Hz, 6H), 1.25 (s, 56H),
1.50-1.80 (br s, 4H), 2.31 (t, J = 8.0Hz, 4H), 3.45-3.75
(m, 20H).

Example 8 Preparation of amide derivative (1d)

[0055]

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The same operation as in Example 6 was carried out except that 39.5 g of myristic acid chloride was used instead of palmitic acid chloride, and 40.8 g of the amide derivative (1d) was obtained.
(78% yield). Properties: White crystals Melting point: 85.0 ° C ¹ H-NMR (CDCl ₃ , δ); 0.88 (t, J = 6.7 Hz, 12H), 1.25 (s, 96)
H), 1.51-1.70 (br s, 8H), 2.24-2.43 (m, 8H), 3.40-3.67
(m, 16H), 4.18 (t, J = 4.8Hz, 4H).

Example 9 Preparation of amide derivative mixture (1e)

[0058]

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In Example 6, mixed fatty acid chloride 45.7 in a weight ratio of stearic acid chloride and palmitic acid chloride of 3: 2 instead of palmitic acid chloride.
The same operation was carried out except that g was used, and the amide derivative mixture (1e) (in which R ¹ was both C ₁₇ H ₃₅ and one in which R ¹ was C ₁₇ H ₃₅ and the other was C ₁₅ H ₃₁ ) The main component,
Other mixtures including those in which both R ¹ are C ₁₅ H ₃₁ ) 45.
2 g (77% yield) were obtained. Property: White crystal Melting point: 81.5 ° C

Example 10 Production of Amide Derivative (1a) 18.9 of the intermediate (5a) produced in (1) was placed in a flask.
g and 114.2 g of tetrahydrofuran were charged and mixed by stirring. Here, 44.0 g of palmitic acid chloride
Was added dropwise at 30 ° C. over 1 hour. The mixture was further stirred at 30 ° C. for 1 hour. After evaporating the solvent under reduced pressure, silica gel chromatography (chloroform: methanol = 50: 50).
Purification in 1) gave 13.1 g (23% yield) of the amide derivative (1a).

Test Example 1 Amide derivative (1a) prepared in Example 6 or Example 9
External preparation composition comprising 33% of the amide derivative mixture (1e) prepared in the above and 67% of petrolatum (Products 1 and 2 of the present invention)
Was prepared and evaluated for skin conductance and skin roughness by the following methods. In addition, the same test and evaluation were also performed for an external preparation comprising only petrolatum as a control (Comparative Product 1). Table 2 shows the results. (Test Method) Ten women aged 20 to 50 who had rough skin on their cheeks were subjected to different test preparations on the left and right cheeks for two weeks. The following items were tested on the day after the two-week application was completed. (1) Skin conductance After washing the face with warm water of 37 ° C. and resting in a room at a temperature of 20 ° C. and a humidity of 40% for 20 minutes, the water content of the stratum corneum was measured with a skin conductance meter (manufactured by IBS). . The skin becomes rougher as the conductance value becomes smaller, and the skin becomes heavier when the conductance value is 5 or less. On the other hand, if this value is 20
Above this, skin roughness is hardly recognized. (2) Rough skin score Rough skin was observed with the naked eye and judged according to the following criteria. The score was shown as an average value. 0: No rough skin is recognized 1: Slight rough skin is recognized 2: Skin is roughened 3: Severe rough skin is recognized 4: Severe rough skin is recognized

[0062]

[Table 2]

Test Example 2 The amide derivative (1a) prepared in Example 6 and Example 9
Using the amide derivative mixture (1e) produced in the above, hair rinses (products of the present invention 3, 4) having the compositions shown in Table 3 below were prepared, and the feel of the hair after the treatment with the hair rinses was measured by five expert panelists as follows. Evaluation was based on criteria. As a control, the amide derivative (1a) and the amide derivative mixture (1e)
A hair rinse having the composition shown in Table 3 containing no was prepared and evaluated in the same manner. Table 3 shows the results. -2: Bad -1: Somewhat bad 0: Neither can be said +1: Somewhat good +2: Good

[0064]

[Table 3]

As is evident from the results shown in Table 2, the present invention products 1 and 2 containing the amide derivative (1) have an effect of increasing the water content of the stratum corneum and improve the rough skin as compared with the comparative product 1. The effect is excellent. Table 3 above
As is clear from the results shown in the above, the products 3 and 4 of the present invention are excellent in the effect of improving the roughness of hair and improving the feel.

Example 11 A skin lotion was prepared according to a conventional method using the composition shown in Table 4. The obtained skin lotion exhibited excellent moisturizing effects, skin roughness prevention / improvement effects, and the like. The amide derivative mixture (1e) produced in Example 9 was excellent in compoundability and compounding stability.

[0067]

[Table 4]

Example 12 An O / W cream having the composition shown in Table 5 was produced according to a conventional method. The obtained O / W cream exhibited an excellent moisturizing effect, an effect of preventing and improving rough skin, and the like. The amide derivative mixture (1e) produced in Example 9 was excellent in compoundability and compounding stability.

[0069]

[Table 5]

Example 13 A shampoo having the composition shown in Table 6 was produced according to a conventional method. This shampoo improved the feel of the hair and prevented and improved the roughness of the scalp. The amide derivative mixture (1e) produced in Example 9 was excellent in compoundability and compounding stability.

[0071]

[Table 6]

Example 14 A hair liquid composition having the composition shown in Table 7 was produced according to a conventional method. The resulting hair liquid composition imparted excellent style retention and formability and good feel to the hair. Further, the amide derivative mixture (1e) produced in Example 9
Had excellent compoundability and compounding stability.

[0073]

[Table 7]

Continuing on the front page (72) Inventor Mitsuru Sugiyama 2606 Akabane, Kaigamachi, Haga-gun, Tochigi Pref. CC05 CC32 CC38 CC39 DD23 DD33 EE01 EE06 EE10 EE12 EE13 EE28 EE29 4H006 AA01 AA03 AB12 BN10 BV22

Claims (2)

[Claims] 1. The following general formula (1): (Wherein two R ¹ may be the same or hydroxy group may be substituted or different, represents a linear or branched hydrocarbon group having 1 to 39 carbon atoms, R ² is a hydroxy group Represents a linear or branched divalent hydrocarbon group having 1 to 12 carbon atoms which may be substituted, and R ³ represents a linear or branched divalent hydrocarbon group having 2 to 12 carbon atoms. And R ⁴ represents 2 carbon atoms
And 6 represents a straight-chain or branched-chain hydroxyalkyl group. An external preparation composition containing the amide derivative represented by the formula (1). 2. The following general formula (2): (Wherein two R ^1-a are the same or different and have 13 to
And 17 linear or branched alkyl groups. An amide derivative represented by the formula: