JPH08337563A - N-acyl amino acid and its salt - Google Patents

Abstract

(57) [Abstract] [Problem] Hair growth agent, hair nourishing agent, detergent, dispersant having excellent surface activity, bactericidal action, metal corrosion inhibitory action, hair nourishing action, moisturizing action, subcutaneous blood flow increasing action, etc. Provided is an N-acyl amino acid composition suitable as an emulsifier, an antibacterial agent, a preservative, an ultraviolet absorber, and the like. An N-acyl amino acid or a salt thereof having an acyl group consisting of 13 to 17 odd carbons.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to N-acyl amino acids and salts thereof having a surface active action, bactericidal action, metal corrosion inhibiting action, hair growth promoting action, moisturizing action, subcutaneous blood flow increasing action, etc. The present invention relates to N-acyl amino acids and salts thereof which are useful as the main components of hair nourishing agents, detergents, dispersants, emulsifiers, antibacterial agents, preservatives, ultraviolet absorbers and the like.

[0002]

2. Description of the Related Art A typical amino acid surfactant is a group of N-acyl amino acids obtained by condensing amino acids and fatty acids. Such N-acyl amino acids have various functions such as high safety for environment and ecology, affinity for skin and hair, special association formation derived from amide group, chelating ability and antioxidant ability. It is expected to have a wide range of applications by taking advantage of its characteristics. Heretofore, as such N-acyl amino acids, those obtained by condensing natural fatty acids with amino acids have been reported, but such natural fatty acids, that is, fatty acids constituting various naturally occurring lipids such as vegetable oil and animal oil. It is known that saturated fatty acids such as stearic acid and palmitic acid and unsaturated fatty acids such as oleic acid and linoleic acid are almost all fatty acids having an even number of carbon chains. On the other hand, as an example in which a fatty acid derivative having an even number of carbon atoms such as N-acylglutamate is blended in a detergent, for example, there is a compound described in JP-A-47-42809.

[0003]

However, although the above-mentioned conventional N-acyl amino acids have been proposed to be applied to various uses such as detergents, they are still insufficient in the surfactant activity and should be satisfied. The actual situation is that none of them are effective. The present invention has been made under such circumstances, and has an excellent surface active action, bactericidal action, metal corrosion inhibition action, hair growth promoting action, moisturizing action, subcutaneous blood flow increasing action, etc. An object of the present invention is to provide N-acyl amino acids and salts thereof suitable for agents, dispersants, emulsifiers, antibacterial agents, preservatives, ultraviolet absorbers and the like.

[0004]

Means for Solving the Problems As a result of intensive studies to achieve the above object, the present inventors have found that an N-acyl amino acid having an acyl group having a specific carbon number or its derivative, or these It has been discovered that salts exhibit excellent surface-active action, bactericidal action, metal corrosion inhibiting action, hair growth promoting action, moisturizing action, subcutaneous blood flow increasing action and the like. The present invention has been completed based on such findings. That is, the present invention provides an N-acyl amino acid having an acyl group composed of 13 to 17 odd carbons or a salt thereof.

[0005]

BEST MODE FOR CARRYING OUT THE INVENTION The present invention will be described in more detail below. The present invention relates to an N-acyl amino acid having an acyl group composed of 13 to 17 odd carbons (hereinafter referred to as the acyl amino acid of the present invention) or a salt thereof,
The acylamino acid of the present invention is one in which at least one amino group in the amino acid is acylated with an acyl group having 13 to 17 odd carbons. As the amino acid used in the production of the acyl amino acid or the salt thereof of the present invention, any of naturally occurring amino acids, non-proteinogenic amino acids or amino acids produced by chemical synthesis can be used, and examples thereof include α-amino acids and β-amino acids. Amino acid, γ-
Amino acids, δ-amino acids, aliphatic amino acids, aromatic amino acids, heterocyclic amino acids, neutral amino acids, basic amino acids, acidic amino acids, alanine, valine, leucine, isoleucine, methionine, tryptophan, phenylalanine, glycine, serine, threonine, cysteine , Tyrosine, asparagine, glutamine, lysine, arginine, aspartic acid, β-alanine, hydroxylysine, ornithine, citrulline, 5-aminolevulinic acid,
γ-aminobutyric acid or the like is used.

In the present invention, as the acylamino acid of the present invention, for example, a compound represented by the following general formula (I) can be used.

[0007]

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In the formula, R represents a straight-chain aliphatic hydrocarbon group having an even number of carbon atoms of 12 to 16 which may have a substituent, and R ¹ and R ² are hydrogen, an alkyl group, and hydroxyalkyl group, an aryl group, a hydroxyaryl group, - (CH _{2) y} COOH or represents - (CH _{2) z} NH _2, these groups each carboxyl group (-COOH)
Alternatively, it may be substituted with an amino group (—NH ₂ ). Further, x, y and z each represent an integer of 0-4. In the general formula (I), the carbon number represented by R is 12 to 1.
The even-numbered straight-chain aliphatic hydrocarbon group having 6 carbon atoms may be either saturated or unsaturated. For example, CH ₃ (CH ₂ )
Examples include groups represented by _n − (where n is an odd integer of 11 to 15). In the present invention, when the N-acyl amino acid represented by the general formula (I) is used as a cosmetic such as a hair restorer or a hair nourishing agent, the following general formula (II)
The compound represented by can be preferably used.

[0009]

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In the formula, R ³ is — (CH ₂ ) _y COOH (where y is the same as in the general formula (I) above), and n is the same as above. In this case, the above y is preferably 1 or 2. From the amino acid point of view, the N-acyl amino acid is preferably an acidic amino acid, and particularly preferably N-acyl aspartic acid. From the viewpoint of acyl group, N-tridecanoyl amino acid or N-pentadecanoyl amino acid is preferably used as the N-acyl amino acid. Examples of the salt of the acylamino acid of the present invention include alkali metal salts such as sodium and potassium, alkaline earth metal salts such as calcium, and ethanolamine salts such as monoethanolamine, diethanolamine and triethanolamine. Among these, monosalts are preferred, and monosodium salts, mono-triethanolamine salts and the like are particularly preferably used.

The acylamino acid of the present invention is a condensation reaction of a higher fatty acid chloride and an amino acid, for example, a so-called Schotten-Baumann reaction, or "Biochemistry", Vol. 35, No. 2, 67. ˜74 (1963), “Study of lipoamino acids (I)”, according to the method. Further, the higher fatty acid having an odd number of carbon atoms can be produced by a conventionally known method. That is, for example, α with an even carbon number
-It can be synthesized from an olefin by a so-called oxo method, or can be produced by a method using a microorganism described in JP-A-6-253866.

The acylamino acid and its salt of the present invention have excellent surface-active action, bactericidal action, metal corrosion inhibiting action, hair growth promoting action, moisturizing action, subcutaneous blood flow increasing action, etc. It can be used as an agent, a dispersant, an emulsifier, an antibacterial agent, an antiseptic, an ultraviolet absorber, and the like. More specifically, it is commercialized into hair nourishing agents, hair liquids, hair creams, facial cleansers, shampoos, synthetic soaps, toilet soaps, body lotions, skin creams, rinses, lotions, antiperspirants, bath salts and the like. . In addition, the acylamino acid and the salt thereof of the present invention can be applied to physiologically active surfaces such as anticancer agents and antiviral agents due to their properties. The acylamino acid and the salt thereof of the present invention can be provided for the above-mentioned applications as a composition containing various components as necessary. Such a component is appropriately selected according to its use, type, dosage form, etc., for example, distilled water, alcohols, polyhydric alcohols, fats and oils, polysaccharides, surfactants and other base materials and foaming agents. An enhancer, a thickener, a fragrance, a pigment, a dye, a water-solubility enhancer, vitamins, amino acids, hormones, a vasodilator, an anti-inflammatory agent, a keratolytic agent, a bactericidal agent and the like can be appropriately added.

The composition can be used in various forms such as liquid, powder, cream, mousse, and paste depending on the intended use. The acylamino acid or salt thereof of the present invention can also be prepared by applying a solvent together with various components to be blended if necessary. As such a solvent, any solvent can be used as long as it can dissolve the above compound. Therefore, although water can be used, hydrophilic or lipophilic ones can be used when an organic solvent is used. For example, alcohols such as methanol, ethanol, propyl alcohol, isopropyl alcohol, glycerin, propylene glycol,
Examples thereof include polyethylene glycol and n-paraffin. When the acylamino acid of the present invention and a salt thereof are used as a composition, the amount thereof can be appropriately determined depending on the use, purpose of use, formulation form, etc., but usually 0.01 to 90 based on the entire composition. It can be used in the range of% by weight.

[0014]

The present invention will be described in more detail with reference to the following examples, but the present invention is not limited to these examples. Example 1 Synthesis of N-tridecanoyl-L-aspartic acid (1) Synthesis of tridecanoyl chloride In a 1-liter two-necked flask, 158.7 g of tridecanoic acid was added.
(0.74 mol) and cyclohexane (200 ml) were added, and thionyl chloride (83.3 g, 0.7 mol) was added.
A 0 ml dropping funnel and a reflux tube were set. While stirring and heating the flask at 80 ° C. in an oil bath,
Tridecanoic acid was completely dissolved. Then, thionyl chloride was added dropwise over 2 hours. Furthermore, the oil bath temperature was kept at 80 ° C. for 1 hour. Cyclohexane and thionyl chloride were removed from this reaction solution under reduced pressure by an aspirator,
The resulting reaction mixture was distilled under reduced pressure to obtain 166.0 g (0.71 mol) of tridecanoyl chloride. The yield based on the charged tridecanoic acid was 95.9%.

(2) Synthesis of N-tridecanoyl-L-aspartic acid L-aspartic acid 15.8 was added to a 1-liter three-necked flask.
g (0.12 mol) and sodium hydroxide 9.6g (0.24 mol)
(Mol) was added and stirred with an aqueous solution of 150 ml of water. Acetone 12 after dissolution of aspartic acid
0 ml was added. The reaction solution was cooled to 0 ° C., and 23.3 g (0.1 mol) of tridecanoyl chloride and an aqueous solution of 4 g of sodium hydroxide dissolved in 30 ml of water were simultaneously added dropwise over 30 minutes. Meanwhile, the reaction temperature is 0 to 5
The temperature and pH were kept at 11-12. Then, the mixture was stirred for 2 hours while slowly raising the temperature to room temperature (25 ° C.), and N-
A disodium tridecanoyl-L-aspartate solution was obtained. To the solution, 65 ml of 5N hydrochloric acid was added to adjust the pH of the solution to 1, the precipitated crystals were separated by vacuum filtration, washed with water, and dried under reduced pressure. The obtained crystals were washed with 500 ml of hexane, dried and then recrystallized from a solvent of ethanol: water = 3: 7 to obtain 14.4 g (0.044 mol) of N-tridecanoyl-L-aspartic acid. The yield based on the charged tridecanoyl chloride is 36.8.
%Met. The physical properties of the obtained N-tridecanoyl-L-aspartic acid were as follows.

¹ H-NMR (CD ₃ OD); δ (ppm) 0.89 (t, 3H) 1.29 (s, 22H) 1.55-1.65 (m, 2H) 2.23 (t , 2H) 2.72-2.92 (m, 1H) 4.74 (dd, 1H) IR (cm ^-1 ); 3353, 3310, 2926, 17
25,1296,1196,928 Elemental analysis (C ₁₇ H ₃₁ NO ₅ ); Measured values: carbon 62.15%, hydrogen 9.54%, nitrogen 4.22
% Theoretical value: Carbon 61.98%, hydrogen 9.48%, nitrogen 4.25
% Melting point: 117.5-119.7 ° C

Example 2 Synthesis of N-tridecanoyl-L-aspartic acid monosodium salt 10.0 g (0.03 mol) of N-tridecanoyl-L-aspartic acid obtained by the above method was added to 500 ml 2
Place in a necked flask, add 300 ml of water and stir, then add an aqueous solution of 1.2 g (0.03 mol) of sodium hydroxide in 50 ml of water, heat to 50 ° C. in a water bath, and add N 2. An aqueous solution of tridecanoyl-L-aspartate monosodium was obtained. This was cooled to room temperature, the precipitated crystals were filtered, dried under reduced pressure, and
8.53 g (0.024 mol) of tridecanoyl-L-aspartic acid monosodium salt was obtained. The yield based on the charged N-tridecanoyl-L-aspartic acid was 80.0%.
Met.

Example 3 Synthesis of N-tridecanoyl-L-aspartic acid disodium salt 2.1 g (6.0 mmol) of 30 g of N-tridecanoyl-L-aspartic acid monosodium salt obtained by the above method was added.
Place in a 0 ml flask, add 100 ml of water, stir, and add sodium hydroxide 0.24.
An aqueous solution prepared by dissolving g (6.0 mmol) in 20 ml of water was added to obtain an aqueous disodium N-tridecanoyl-L-aspartate solution. This is freeze-dried and N
-Tridecanoyl-L-aspartic acid disodium salt
2.12 g (5.7 mmol) were obtained. The yield based on the charged monosodium N-tridecanoyl-L-aspartic acid salt was 95.0%.

Example 4 Synthesis of N-pentadecanoyl-L-aspartic acid (1) Synthesis of pentadecanoyl chloride 160.0 g of pentadecanoic acid was placed in a 1 liter 2-necked flask.
(0.66 mol) and cyclohexane (200 ml) were added, and thionyl chloride (83.3 g, 0.7 mol) was added.
A 0 ml dropping funnel and a reflux tube were set. While stirring and heating the flask at 80 ° C. in an oil bath,
After completely dissolving pentadecanoic acid, thionyl chloride was added dropwise over 2 hours. In addition, set the oil bath temperature to 80
Hold at ℃ for 1 hour. Cyclohexane and thionyl chloride were removed from this reaction mixture under reduced pressure of an aspirator, and the resulting crude reaction product was distilled under reduced pressure to obtain 110.0 g (0.42 mol) of pentadecanoyl chloride. The yield based on the charged pentadecanoic acid was 63.9%.

(2) Synthesis of N-pentadecanoyl-L-aspartic acid L-aspartic acid 31.9 was added to a 1-liter three-necked flask.
g (0.24 mol) and sodium hydroxide 19.2 g (0.4
8 mol) and an aqueous solution of 150 ml of water were added and stirred. Acetone 1 after aspartic acid is dissolved
20 ml was added. The reaction solution was cooled to 0 ° C., and 52.2 g (0.2 mol) of pentadecanoyl chloride and 30 ml of 0.2N aqueous sodium hydroxide solution were simultaneously added dropwise over 30 minutes. During that time, the reaction temperature was maintained at 0 to 5 ° C and the pH was maintained at 11 to 12. Then, the mixture was stirred for 2 hours while slowly raising the temperature to room temperature (25 ° C.) to obtain a disodium N-pentadecanoyl-L-aspartate solution. To the solution, 140 ml of 5N hydrochloric acid was added to adjust the pH of the solution to 1, and the precipitated crystals were separated by vacuum filtration.
After washing with water, it was dried under reduced pressure. The obtained crystals were washed with 500 ml of hexane, dried, and recrystallized with a solvent of ethanol: water = 1: 1 to give N-pentadecanoyl-L.
39.8 g (0.11 mol) of aspartic acid were obtained. The yield based on pentadecanoyl chloride charged was 55.6%. The physical properties of the obtained N-pentadecanoyl-L-aspartic acid were as follows.

¹ H-NMR (CD ₃ OD); δ (ppm) 0.89 (t, 3H) 1.28 (s, 26H) 1.55-1.65 (m, 2H) 2.23 (t , 2H) 2.72-2.92 (m, 1H) 4.74 (dd, 1H) IR (cm ^-1 ); 3353, 3310, 2926, 17
25,1296,1196,928 Elemental analysis (C ₁₉ H ₃₅ NO ₅ ); Measured value: Carbon 63.10%, Hydrogen 9.53%, Nitrogen 4.08
% Theoretical value: Carbon 63.84%, hydrogen 9.87%, nitrogen 3.92
% Melting point: 122.8-124.0 ° C

Example 5 Synthesis of N-pentadecanoylaspartic acid monosodium salt 20.0 g (0.056 mol) of N-pentadecanoyl-L-aspartic acid obtained by the above method was put in a 500 ml two-necked flask. Add water, add 300 ml of water, stir, and then add 2.3 g of sodium hydroxide (0.057
An aqueous solution prepared by dissolving 50 mol of water in 50 ml of water,
Heat to 50 ° C. in a water bath to remove N-pentadecanoyl-L-
An aqueous solution of monosodium aspartate was obtained. This was cooled to room temperature and the precipitated crystals were filtered and dried under reduced pressure to give N-pentadecanoyl-L-aspartic acid monosodium salt (19.85 g, 0.052 mol). The yield based on the charged N-pentadecanoyl-L-aspartic acid was 93.5%.

Example 6 Synthesis of N-pentadecanoyl-aspartic acid disodium salt 2.1 g (5.5 mmol) of 3 g of N-pentadecanoyl-L-aspartic acid monosodium salt obtained by the above method was added.
Put in a 00 ml flask, add 100 ml of water, stir, and then add sodium hydroxide 0.2
An aqueous solution prepared by dissolving 2 g (5.5 mmol) in 20 ml of water was added to obtain an aqueous disodium N-pentadecanoyl-L-aspartate solution. This was freeze-dried to obtain 2.19 g (5.5 mmol) of N-pentadecanoyl-L-aspartic acid disodium salt. Charged N
The yield based on pentadecanoyl-L-aspartic acid monosodium salt was 98.6%.

Example 7 Synthesis of N-heptadecanoyl-L-aspartic acid (1) Synthesis of heptadecanoyl chloride 102.1 g of heptadecanoic acid was placed in a 1-liter two-necked flask.
(0.38 mol) and cyclohexane (200 ml) were added, and thionyl chloride (67.3 g, 0.57 mol) was added.
A 00 ml dropping funnel and a reflux tube were set.
While the flask was heated and stirred at 80 ° C. in an oil bath, heptadecanoic acid was completely dissolved, and thionyl chloride was added dropwise over 2 hours. Furthermore, the oil bath temperature was kept at 80 ° C. for 1 hour. Cyclohexane and thionyl chloride were removed from this reaction mixture under reduced pressure of an aspirator, and the obtained reaction mixture was distilled under reduced pressure to obtain 88.5 g (0.31 mol) of heptadecanoyl chloride. The yield based on the charged heptadecanoic acid was 81.2%.

(2) Synthesis of N-heptadecanoyl-L-aspartic acid L-aspartic acid 16.0 was added to a 1-liter three-necked flask.
g (0.12 mol) and sodium hydroxide 9.6g (0.24 mol)
(Mol) was added and stirred with an aqueous solution of 150 ml of water. Acetone 12 after dissolution of aspartic acid
0 ml was added. The reaction solution was cooled to 0 ° C., and 29.0 g (0.1 mol) of heptadecanoyl chloride and an aqueous solution of 4 g of sodium hydroxide dissolved in 30 ml of water were simultaneously added dropwise over 30 minutes. Meanwhile, the reaction temperature is 0 to 5
The temperature and pH were kept at 11-12. Then, the mixture was stirred for 2 hours while slowly raising the temperature to room temperature (25 ° C.), and N-
A heptadecanoyl-L-aspartate disodium solution was obtained. To the solution, 65 ml of 5N hydrochloric acid was added to adjust the pH of the solution to 1, the precipitated crystals were separated by vacuum filtration, washed with water, and dried under reduced pressure. The obtained crystals were washed with 500 ml of hexane, dried, and then recrystallized with a solvent of ethanol: methanol = 8: 1 to give N-heptadecanoyl-L-aspartic acid 21.0 g (0.05).
4 mol) was obtained. The yield based on the charged heptadecanoyl chloride was 54.3%. The physical properties of the obtained N-heptadecanoyl-L-aspartic acid were as follows.

¹ H-NMR (CD ₃ OD); δ (ppm) 0.89 (t, 3H) 1.28 (s, 30H) 1.55-1.65 (m, 2H) 2.23 (t , 2H) 2.72-2.92 (m, 1H) 4.74 (dd, 1H) IR (cm ^-1 ); 3353, 3310, 2926, 17
25,1296,1196,928 Elemental analysis (C ₂₁ H ₃₉ NO ₅ ); Measured value: Carbon 65.34%, Hydrogen 10.07%, Nitrogen 3.8
5% Theoretical value: Carbon 65.42%, Hydrogen 10.20%, Nitrogen 3.6
3% melting point: 126.4-128.5 ° C

Examples 8 to 11 and Comparative Examples 1 to 6 For each of the N-acyl amino acid salts shown in Table 1 synthesized according to Production Examples 1 to 7 or according to these, the surface tension and The foaming degree was examined. The result is N-
Table 1 shows each of the acylleucine monosodium salt, the N-acyl aspartic acid monosodium salt and the N-acyl aspartic acid disodium salt. Surface tension test A 0.3 wt% aqueous solution of N-acyl amino acid salt was prepared, and the surface tension was measured by the ring method at 40 ° C (60 ° C in the case of N-acyl aspartic acid monosodium salt). Foaming test 20 ml of a 0.1% by weight aqueous solution of N-acyl amino acid salt was placed in a 100 ml measuring cylinder equipped with a stopper, shaken vigorously up and down 20 times, and immediately placed on a horizontal surface. It was left to stand, the volume of the foam was read from the scale, and this was evaluated as the foaming power. The measurement is 40 ° C.
Was carried out under the following temperature conditions.

[0028]

[Table 1]

[0029]

[Table 2]

[0030]

[Table 3]

Examples 12 and 13 and Comparative Examples 7 and 8 Male 8 week-old C3H mice (body weight 18 to 24 g) were used.
About 2 × 3.5 cm of the back of each group of animals was shaved, and a 1% by weight ethanol solution of the N-acyl amino acid compound shown in Table 2 was used as a test sample on the shaved back of the animal, once a day for 0. 1
The state of hair growth was observed by applying milliliters for 3 weeks. To evaluate the hair-growth effect, a photograph was taken of the test area on the back of the mouse, the area was measured using a planimeter from the photograph, and the ratio of the area of the hair regeneration site to the area of the entire test area was determined as the recurrence rate. The results are shown in Table 2.
According to these results, particularly good hair-growth effect was observed in the N-acyl amino acid having an odd number carbon atom acyl group of the present invention. The application of the test sample had no effect on general symptoms, skin conditions and body weight changes during the test period. The N-acyl amino acid compound used here is the one synthesized according to the above Production Examples 1 to 7 or these.

[0032]

[Table 4]

Further, as examples of the present invention, various forms of the composition containing the acylamino acid of the present invention will be shown below together with the composition thereof. Example 14 Toilet soap Wt% pentadecanoyl aspartic acid mono Na salt 83.0 Cetanol 8.0 Purified water 8.5 Perfume 0.5

Example 15 Cleansing Foam Weight% Tridecanoyl Aspartic Acid Mono-Triethanol Amine Salt 25.0 Myristic Acid 10.0 Cetanol 2.0 Glycerin 10.0 Potassium Hydroxide 3.0 Polyethylene Glycol 10.0 Perfume 0 .5 Purified water 39.5

Example 16 Shampoo wt% pentadecanoyl aspartic acid mono-triethanol amine salt 15.0 lauric acid diethanolamide 5.0 propylene glycol 2.0 perfume 0.1 purified water 77.9

Example 17 Shampoo wt% Tridecanoyl aspartic acid mono Na salt 5.0 Polyoxyethylene sorbitan fatty acid ester 5.0 Sodium lauryl sulfate 5.0 Glycerin 2.0 Purified water 83.0

Example 18 Lotion wt% pentadecanoyl aspartic acid mono Na salt 2.0 Glycerin 5.0 Propylene glycol 5.0 Polyethylene glycol 2.0 Ethanol 8.0 Perfume 0.1 Purified water 77.9

Example 19 Emollient Lotion Wt% Tridecanoyl Aspartic Acid Mono Na Salt 2.0 Tridecanoyl Leucine Mono Na Salt 1.0 Beeswax 0.5 Vaseline 2.0 Squalane 5.0 Propylene Glycol 5.0 Ethanol 5.0 1% CMC aqueous solution 20.0 Potassium hydroxide 0.1 Perfume 0.1 Purified water 59.3

Example 20 Lipstick wt% Solid paraffin 10.0 Titanium oxide 1.0 Lanolin 5.0 Beeswax 2.0 Carbana wax 2.0 Heptadecanoyl aspartic acid 2.0 Octadecanol 15.0 Castor oil 49. 9 Dye 5.0 Perfume 0.1

Example 21 Foundation wt.% Titanium oxide 15.0 Kaolin 20.0 Talc 10.0 Bengalala 2.0 Tridecanoyllysine 2.0 Ceresin 10.0 Carbanalow 2.0 Liquid paraffin 17.0 Isopropyl myristate 15 0.0 Sorbitan monooleate 2.0 Fragrance 0.5

Example 22 Hair nourishment wt% Ethanol 78.0 N-pentadecanoyl aspartic acid 0.5 Olive oil 1.0 α-Tocopherol 0.5 Perfume 0.5 Purified water 19.5 Preservative (appropriate amount)

Example 23 Hair Liquid Weight% Ethanol 40.0 N-pentadecanoyl aspartic acid 2.0 Glycerin 1.0 Polyoxyethylene glycol monoether 10.0 Perfume 0.5 Purified water 46.5 Preservative (appropriate amount )

Example 24 Hair Cream Weight% N-pentadecanoyl aspartic acid 10.0 Liquid paraffin 30.0 Sorbitan monooleate 2.0 Perfume 0.5 Purified water 57.5 Preservative (appropriate amount)

[0044]

EFFECTS OF THE INVENTION By using the acylamino acid or its salt of the present invention, a hair-growing agent having excellent surface-active action, bactericidal action, metal corrosion inhibitory action, hair growth promoting action, moisturizing action, subcutaneous blood flow increasing action, etc. Hair nourishing agent, cleaning agent, dispersant,
It is possible to obtain an N-acyl amino acid composition such as an emulsifier, an antibacterial agent, a preservative, and an ultraviolet absorber.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification number Internal reference number FI Technical display location C07D 209/20 C07D 209/20 C11D 1/10 C11D 1/10 (72) Inventor Yoshihiro Takayama Ibaraki Prefecture 4 Towada, Kamisu-cho, Kashima-gun Kashima Oil Co., Ltd. Kashima Refinery

Claims (5)

[Claims] 1. An N-acyl amino acid having an acyl group consisting of 13 to 17 odd carbons or a salt thereof. 2. The N-acyl amino acid according to claim 1, wherein the N-acyl amino acid having an acyl group consisting of 13 to 17 odd carbons is obtained by using an acidic amino acid. salt. 3. The N-acyl amino acid according to claim 1, wherein the N-acyl amino acid having an acyl group consisting of 13 to 17 odd carbons is obtained by using a basic amino acid. Its salt. 4. The N-acyl amino acid according to claim 1, wherein the N-acyl amino acid having an acyl group composed of 13 to 17 odd carbons is obtained by using a neutral amino acid. Its salt. 5. An N-acyl amino acid having an acyl group consisting of 13 to 17 odd carbons is alanine, valine,
Leucine, isoleucine, methionine, tryptophan, phenylalanine, glycine, serine, threonine, cysteine, tyrosine, asparagine, glutamine, lysine, arginine, aspartic acid, β-alanine, hydroxylysine, ornithine, citrulline, 5-
The N-acyl amino acid or a salt thereof according to claim 1, which is obtained by using an amino acid selected from aminolevulinic acid and γ-aminobutyric acid.