JPH11240828A - Oily raw material for cosmetic material - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject raw material improving an oily feeling and a sticky feeling, making a use feeling of a cosmetic composition as excellent and further excellent in conditioning effect on hair by containing a specific long chain acyl neutral amino acid ester. SOLUTION: This oily raw material for a cosmetic material is obtained by containing an N-long chain acyl neutral amino acid ester having a linear or non-linear and saturated or unsaturated chain 6-22C acyl group, in which a hydrocarbon group constituting the ester part is a linear or branched and saturated or unsaturated chain 1-10C hydrocarbon (e.g.: N-octanoylglycine isopropyl ester). The raw material can be used as an oily raw material for various cosmetic composition such as a skin cosmetic material and a hair cosmetic material, and the preferable blending amount of the above ester in the above cases, is 0.1-60 wt.% in the case of the skin cosmetic composition, and 0.1-30 wt.% in the case of the hair cosmetic composition.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to an oily raw material for cosmetics comprising a specific N-long-chain acyl neutral amino acid ester,
And a cosmetic composition containing the same. More specifically, an oily composition for cosmetics comprising an N-long-chain acyl-neutral amino acid ester in which the hydrocarbon group in the ester portion is a branched or straight-chain saturated or unsaturated hydrocarbon group having 1 to 10 carbon atoms. The present invention relates to a raw material and a cosmetic composition containing the same.

[0002]

2. Description of the Related Art In cosmetic compositions, oily raw materials are widely used as binders for ingredients, emollients, etc., and for the purpose of imparting conditioning properties to hair. Conventionally, as oily raw materials used for cosmetic compositions, mineral oils such as liquid paraffin and esterified products of fatty acids such as IPM (isopropyl myristate) and IPP (isopropyl palmitate) have been widely used.

[0003] There is also known an example using an amino acid derivative as an oily raw material. For example, Japanese Patent Publication No. 54-1290
No. 8 discloses N-long-chain acyl neutral amino acids and C12 to C3 as oil-soluble surfactants suitable for the cosmetic field.
Esters with 0 higher alcohols are disclosed.

[0004] However, these oily raw materials for cosmetics have a problem that the unpleasant oily feeling and sticky feeling peculiar to the oily raw materials impair the feeling of use of the cosmetic composition.
In addition, the conditioning effect on hair was not sufficient. Therefore, an oily raw material for cosmetics which is more excellent in these points has been desired.

As esters of N-long-chain acyl-neutral amino acids, esters with long-chain alcohols are known as described in JP-B-54-12908, but alcohols having shorter chain lengths are known. There are few known examples of the esters with which they were actually synthesized and studied for use in cosmetics. As a specific example, N-2-ethylhexanoyl-N-methyl-β-alanine methyl ester was tested from the lower column on page 167 to the upper column on the left column on page 168 of JP-B-54-1229078, and the It is only disclosed as having poor compatibility with the solvent. As described above, esters of N-long-chain acyl-neutral amino acids with short-chain alcohols have never been used as oily raw materials for cosmetics.

[0006] However, in recent years, due to advances in compounding techniques, emulsifying equipment, and the like, these compatibility problems are rarely regarded as important, and it is important to respond to the diversification and sophistication of consumer needs. Has become.

[0007]

SUMMARY OF THE INVENTION It is an object of the present invention to provide a cosmetic composition having an improved oily feeling and a sticky feeling, an improved feeling of use of the cosmetic composition, and an excellent conditioning effect on hair. An object of the present invention is to provide an oily raw material, and further to provide a cosmetic composition containing the same.

[0008]

Means for Solving the Problems The inventors of the present invention have conducted intensive studies in view of the above circumstances, and as a result, have found that the hydrocarbon group constituting the ester site is an N-C 1-10 hydrocarbon group.
The long-chain acyl neutral amino acid ester has a smooth or refreshing feel even though it is an oily raw material, and when used in a cosmetic composition, in addition to the refreshing feeling, gives a feeling of use to the skin such as stretching, familiarity, and smoothness. The present invention was also found to be excellent, and was also found to have an excellent conditioning effect on hair, and completed the present invention.

That is, the present invention relates to an ester of an N-long-chain acyl-neutral amino acid having an acyl group having 6 to 22 carbon atoms, wherein the ester site is an N-ester having a hydrocarbon group having 1 to 10 carbon atoms. It is an oily raw material for cosmetics consisting of a long-chain acyl neutral amino acid ester. The present invention is also a cosmetic composition comprising the oily raw material for cosmetics.

[0010]

DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention will be described below in detail.

In the present invention, the long-chain acyl group of the N-long-chain acyl neutral amino acid ester has 6 to 2 carbon atoms.
2, straight or branched saturated or unsaturated, for example, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, linoleic acid, linoleic acid, oleic acid, isostearic acid, -Acyl groups which can be derived from ethylhexanoic acid, coconut oil fatty acid, tallow fatty acid, hardened tallow oil fatty acid, palm kernel oil fatty acid and the like. Preferred acyl groups include a caproyl group, a lauroyl group, a myristyl group, a palmitoyl group, a stearoyl group, a behenoyl group, a coconut oil fatty acid acyl group, and a hydrogenated tallow oil fatty acid acyl group.

The neutral amino acids constituting the neutral amino acid site include, for example, glycine, alanine, valine, leucine, isoleucine, serine, threonine, proline, β
-Alanine, aminobutyric acid, sarcosine, N-methyl-β
-Neutral amino acids such as alanine. Preferred are glycine, alanine, valine, leucine, isoleucine, β-alanine, aminobutyric acid, γ-aminobutyric acid, sarcosine, N-methyl-β-alanine, and more preferred are glycine, alanine, β-
Alanine, aminobutyric acid, γ-aminobutyric acid, sarcosine and N-methyl-β-alanine. More preferred are sarcosine, alanine, glycine and N-methyl-β-alanine, particularly preferred are N-alkyl neutral amino acids, and most preferred are sarcosine and N-methyl-β-alanine. These amino acids may be either optically active or racemic.

The hydrocarbon group constituting the ester moiety is a branched or straight-chain alkyl or alkenyl group having 1 to 10 carbon atoms, preferably an alkyl group, for example, ethanol, propanol, isopropanol. , Butanol, t-butanol, isobutanol,
Examples include hydrocarbon groups that can be derived from 3-methyl-1-butanol, 2-methyl-1-butanol, fusel oil, pentanol, hexanol, cyclohexanol, octanol, 2-ethylhexanol, decanol. Methyl ester having 1 carbon atom is not preferable because methanol is used as a raw material.

Further, from the viewpoint of feeling of use, the number of carbon atoms is 2 to 8
Is preferably a branched or linear alkyl group. In particular, a branched or straight-chain alkyl group having 2 to 5 carbon atoms is more preferable because it is excellent in smooth or refreshing feel and the effect of the present invention is more sufficiently exhibited. From the viewpoint of stability in use as well as hydrolysis stability, a branched alkyl group having 3 to 5 carbon atoms is preferable, and examples thereof include an isopropyl group, a t-butyl group, and an isobutyl group. Most preferred is the isopropyl group.

A preferred example of the N-long-chain acyl-neutral amino acid ester in the present invention is represented by the following general formula, and examples thereof include those represented by the following general formula (1).

[0016]

Embedded image

In the formula, R ¹ represents a branched or linear alkyl or alkenyl group having 5 to 21 carbon atoms, and R ² represents a hydrogen atom or a linear or branched alkyl group having 1 to 3 carbon atoms. R ³ represents a hydrogen atom or a linear or branched alkyl group having 1 to ⁴ carbon atoms, and R ⁴ represents a branched or linear alkyl group or alkenyl group having 1 to 10 carbon atoms. And n represents an integer of 0 to 2. )

In the general formula (1), an acyl group (R ¹ -CO
More preferred as R ⁴ of the hydrocarbon group constituting-) and the ester moiety are as described above. More preferred neutral amino acid sites are also as described above,
R ² is more preferably a hydrogen atom or a methyl group, particularly preferably a methyl group, R ³ is more preferably a hydrogen atom or a methyl group, particularly preferably a hydrogen atom, and n is 0 or 1 Is more preferable.

The N-long-chain acyl-neutral amino acid ester in the present invention can be obtained, for example, by subjecting an N-long-chain acyl-neutral amino acid and an alcohol to dehydration condensation esterification by heating under normal pressure or reduced pressure. Further, an azeotropic dehydration / condensation reaction using a solvent such as toluene (the following Production Examples 5 and 6)
Etc.) or a transesterification reaction. The N-long-chain acyl-neutral amino acid and the alcohol used for the synthesis of such N-long-chain acyl-neutral amino acid ester do not necessarily need to be a single compound. -It may be a mixture of long-chain acyl neutral amino acids or a mixture of alcohols having different chain lengths.

The obtained N-long-chain acyl neutral amino acid ester can be purified and used by a known method usually used by those skilled in the art, such as distillation, extraction, chromatography and the like. In addition, N-long-chain acyl neutral amino acids and salts thereof as production raw materials, alcohols and the like permitted in cosmetic compositions, and further, raw materials that may be contained in N-long-chain acyl neutral amino acids and salts thereof The neutral amino acids and the like and fatty acids and the like as by-products are commonly used in cosmetic compositions, and may be contained within a range that does not impair the effects of the present invention.

Incidentally, the N-long-chain acyl neutral amino acid is
For example, it can be produced by a known method such as a so-called Schotten-Baumann reaction in which a long-chain fatty acid halide is reacted with an amino acid under a basic catalyst (see Japanese Patent Publication No. 51-38681).

The oily raw material for cosmetics of the present invention can be used as an oily raw material for various cosmetic compositions such as skin cosmetics and hair cosmetics, and can be used as the cosmetic composition of the present invention. As such a cosmetic composition, for example,
Facial cleansing cream, facial cleansing foam, cleansing cream,
Massage cream, cold cream, moisture cream, milky lotion, lotion, hand cream, pack, men's skin cosmetics, foundation, lipstick, press powder, eye shadow, tic, hair liquid, set lotion, permanent wave liquid, hair cream, hair Lotion, hair mousse, shampoo, hair rinse,
Hair conditioner, body shampoo, solid detergent,
Various cosmetic compositions such as a liquid detergent, an antiperspirant, an after shaving cream, a sunscreen cream, a sunscreen oil, a bath agent, and a hair dye can be exemplified. There is no particular limitation on the form of the cosmetic composition, and any agent such as an emulsion system, a solution system, a solubilizing system, a powder dispersion system, a water-oil two-layer system, a water-oil-powder three-layer system, etc. It can be a type.

In the cosmetic composition of the present invention, other oily raw materials that can be used in cosmetics can be arbitrarily added as long as the effects of the present invention are not impaired. Such include, for example, saturated or unsaturated fatty acids and higher alcohols obtained therefrom, squalane, castor oil and derivatives thereof, beeswax, lanolins and derivatives thereof including liquid and purified lanolin, cholesterol and derivatives thereof, macadamia nuts Oil, jojoba oil, carnauba wax, sesame oil, cocoa oil, palm oil, mink oil, wood wax, candelilla wax, oily raw materials derived from animals and plants such as whale wax, paraffin, microcrystalline wax, liquid paraffin, petrolatum, vaseline, ceresin, etc. In addition to oil-based raw materials derived from minerals, methylpolysiloxane, polyoxyethylene / methylpolysiloxane, polyoxypropylene / methylpolyoxysiloxane, poly (oxyethylene, oxypropylene) / methylpolysiloxane, methylphenylpoly Rokisan, fatty acid-modified polysiloxanes, silicones such as silicone polymers, such as aliphatic alcohol-modified polysiloxane, amino-modified polysiloxane, resin acids, fatty esters, and ketones. Since the N-acyl neutral amino acid ester in the present invention also has an effect of improving the sticky feeling of other oily raw materials, the N-acyl neutral amino acid ester can be sufficiently used in a cosmetic composition containing the conventional oily raw materials as described above. It is possible to exhibit the effect.

Further, the cosmetic composition of the present invention may contain, as a surfactant, an N-long-chain acyl acidic amino acid salt or an N-long-chain acyl neutral amino acid salt as long as the effects of the present invention are not impaired. N-long chain acyl amino acid salt, N-long chain fatty acyl-N-methyltaurine salt, alkyl sulfate and its alkylene oxide adduct, fatty acid amide ether sulfate, metal salt and weak base salt of fatty acid, sulfosuccinic surfactant , Anionic surfactants such as alkyl phosphates and their alkylene oxide adducts, alkyl ether carboxylic acids; ether type surfactants such as glycerin ether and its alkylene oxide adducts; esters such as glycerin esters and their alkylene oxide adducts -Type surfactant, sorbitan ester and its alcohol Ether ester surfactants such as lenoxide adducts, polyoxyalkylene fatty acid esters, glycerin esters, fatty acid polyglycerin esters, sorbitan esters, sucrose fatty acid esters, and other ester surfactants, alkyl glucosides, hydrogenated castor oil pyroglutamic acid Nonionic surfactants such as diesters and their ethylene oxide adducts and nitrogen-containing nonionic surfactants such as fatty acid alkanolamides; aliphatic ammonium salts such as alkylammonium chloride and dialkylammonium chloride;
Cationic surfactants such as aromatic quaternary ammonium salts such as quaternary ammonium salts and benzalkonium salts; fatty acyl arginine esters; betaine surfactants such as carboxybetaine; aminocarboxylic acid surfactants And various surfactants such as amphoteric surfactants such as imidazoline surfactants.

Further, the cosmetic composition of the present invention includes:
In addition to the above surfactants, various additives commonly used in cosmetic compositions can be added as long as the effects of the present invention are not impaired. For example, amino acids such as glycine, alanine, serine, threonine, arginine, glutamic acid, aspartic acid, leucine and valine; polyhydric alcohols such as glycerin, ethylene glycol, 1,3-butylene glycol, propylene glycol and isoprene glycol; polyglutamic acid , Polyamino acids including polyaspartic acid and salts thereof, polyethylene glycol, gum arabic, alginate, xanthan gum, hyaluronic acid, hyaluronic acid, chitin, chitosan, water-soluble chitin, carboxyvinyl polymer, carboxymethylcellulose, hydroxyethylcellulose,
Water-soluble polymers such as hydroxypropyltrimethylammonium chloride, polydimethylmethylenepiperidium chloride, polyvinylpyrrolidone derivatives, quaternary ammonium, cationized proteins, collagen degradation products and derivatives thereof, acylated proteins, polyglycerin, etc .; sugar alcohols such as mannitol And its alkylene oxide adducts; lower alcohols such as ethanol and propanol; animal and plant extracts; nucleic acids, vitamins, enzymes, anti-inflammatory agents, bactericides, preservatives, antioxidants, ultraviolet absorbers, chelating agents, Sweats, pigments, dyes, oxidation dyes, organic and inorganic powders, pH adjusters, pearlizing agents, wetting agents and the like can be incorporated.

The amount of the N-long-chain acyl neutral amino acid ester in the present invention varies depending on the product form and is not particularly limited, but is usually used in a range of 0.01% by weight or more. The preferred range is 0.1 to 50% by weight for the skin cosmetic composition, and preferably 0.1 to 30% by weight for the hair cosmetic composition.

[0027]

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.

Production Example 1 Synthesis of N-octanoylglycine isopropyl ester 50 g of N-octanoylglycine and 5 g of isopropanol
00 mL was placed in a 1000 mL flask, 1 mL of concentrated sulfuric acid was further added as a catalyst, and the mixture was reacted under heating and refluxing for 8 hours.
After completion of the reaction, the system was left to room temperature. After cooling, excess isopropanol was distilled off under reduced pressure. The concentrate was placed in an oil separator and maintained at 50 ° C., and about 300 mL of a saturated aqueous sodium hydrogen carbonate solution was added to neutralize the oil, and the oil phase was extracted. The oil phase was further washed with water and dried under reduced pressure to obtain 39 g (yield: 64%) of the title compound as a white solid. ESI (Electrospray Ionization) -MS: 244 (M + H) ⁺ IR (KBr): 2900 cm ^-1 (CH), 1710 cm ^-1 (ester), 1640 cm ^-1 (amito)

Production Example 2 Synthesis of N-octanol-N-methyl-β-alanine isopropyl ester 57 g of N-octanol-N-methyl-β-alanine and 500 mL of isopropanol were placed in a 1000 mL flask, and 1 mL of concentrated sulfuric acid was further used as a catalyst. In addition, 8
Allowed to react for hours. After completion of the reaction, the system was left to room temperature.
Excess isopropanol was distilled off under reduced pressure. About 300 mL of saturated aqueous sodium hydrogen carbonate solution was added to the concentrate to neutralize it,
The oil phase was extracted. The obtained oil phase was washed with water and further dried under reduced pressure to obtain 57 g of the title compound as a transparent liquid.
(84% yield). IR (neat): 2950 cm ^-1 (CH), 1710 cm ^-1 (ester), 1640 cm ^-1 (amito)

Production Example 3 Synthesis of N-octanoyl-β-alanine octyl ester 57 g of N-octanoyl-β-alanine and 36 g of octanol, 500 mL of toluene as a solvent, and 1000 mL of toluene
The mixture was placed in a flask, 2 g of paratoluenesulfonic acid monohydrate was further added as a catalyst, and the mixture was reacted under heating and refluxing for 8 hours.
After completion of the reaction, the system was left to room temperature. After allowing to cool, about 500 mL of a saturated aqueous sodium hydrogen carbonate solution was added to neutralize, and the organic phase was extracted. The obtained organic phase was washed with water, and excess toluene was distilled off under reduced pressure. The residue was further recrystallized from hexane and dried under reduced pressure to obtain 50 g (yield 57%) of the title compound as a solid. IR (KBr): 2900cm ^-1 (CH), 1730cm ^-1 (ester), 1640cm ^-1 (amito)

Production Example 4 Synthesis of N-lauroyl-γ-aminobutyric acid octyl ester 47 g of N-lauroyl-γ-aminobutyric acid, 24 g of octanol and 500 mL of toluene were placed in a 1000 mL flask, and paratoluenesulfonic acid monohydrate was further used as a catalyst. 2 g of the product was added, and the mixture was reacted for 8 hours under reflux with heating. After completion of the reaction, the system was left to room temperature. After allowing to cool, about 500 mL of a saturated aqueous sodium hydrogen carbonate solution was added to neutralize, and the oil phase was extracted. The obtained oil phase was washed with water, and excess toluene was distilled off under reduced pressure. The residue was further recrystallized from hexane and dried under reduced pressure to obtain 42 g (yield 63%) of the title compound as a solid. IR (KBr): 2900cm-1 (CH), 1730cm-1 (ester), 1640cm-1 (Amit ゛)

Production Example 5 Synthesis of N-coconut fatty acid acylalanine isopropyl ester N-coconut fatty acid acylalanine (acyl group composition (weight ratio): capryl group 11.3%, caproyl group 9.4)
%, Lauroyl group 58.7%, myristoyl group 18.5
%, Palmitoyl group 2.1%) and 750 mL of isopropanol were placed in a 1000 mL flask, 2 mL of concentrated sulfuric acid was further added as a catalyst, and the mixture was reacted under heating and reflux for 20 hours. After completion of the reaction, the system was left to room temperature. After cooling down,
Excess isopropanol was distilled off under reduced pressure. The concentrate was neutralized with about 500 mL of a saturated aqueous sodium hydrogen carbonate solution, and the obtained oil phase was further washed with water and dried under reduced pressure to obtain 82 g (yield 71%) of the title compound as a transparent liquid. ^{ESI-MS: 286,314,342 (M +} H) + IR (neat): 2950cm -1 (C-H), 1725cm -1 ( ester), 1600 cm ^-1 (Amito Bu)

Production Example 6 Synthesis of isopropyl N-myristoyl-γ-aminobutyrate 40 g of N-myristoyl-γ-aminobutyric acid and 500 mL of isopropanol were placed in a 1000 mL flask, 2 mL of concentrated sulfuric acid was further added as a catalyst, and the mixture was heated to reflux 8 Allowed to react for hours. After completion of the reaction, the system was left to room temperature. Excess isopropanol was distilled off under reduced pressure. The residue was dissolved in 300 mL of diethyl ether, neutralized with about 300 mL of a saturated aqueous sodium hydrogen carbonate solution, and the obtained organic phase was further washed with water. About 5 g of the extracted organic phase is anhydrous magnesium sulfate
And dried over anhydrous magnesium sulfate. The ether of the mother liquor was distilled off, and the residue was recrystallized from ethanol and dried under reduced pressure to give the title compound 25 as a solid.
g (yield 56%) was obtained. I got IR (KBr): 2940 cm ^-1 (CH), 1730 cm ^-1 (ester), 1610 cm ^-1 (amito)

Production Example 7 Synthesis of N-myristoyl glycine octyl ester 36 g of N-myristoyl glycine and octanol 16
g, 300 mL of toluene into a 500 mL flask,
Further, 1 g of paratoluenesulfonic acid monohydrate is used as a catalyst.
In addition, the mixture was reacted for 10 hours while heating under reflux. After completion of the reaction, the system was left to room temperature. After cooling, about 300 mL of a saturated aqueous sodium hydrogen carbonate solution was added for neutralization, and the organic phase was extracted. The obtained organic phase was washed with water, and excess toluene was distilled off under reduced pressure. The residue was further recrystallized from hexane and dried under reduced pressure to give the title compound 27 as a solid.
g (66% yield). ^{IR (KBr): 2950cm -1 (} CH), 1725cm -1 ( ester), 1600 cm ^-1 (Amito Bu)

Production Example 8 Synthesis of N-stearoylalanine octyl ester N-stearoylalanine 40 g, octanol 16
g, 400 mL of toluene into a 500 mL flask,
Further, 1 g of paratoluenesulfonic acid monohydrate is used as a catalyst.
In addition, the mixture was reacted for 6 hours under heating and reflux. After completion of the reaction, the system was left to room temperature. After cooling, about 500 mL of a saturated aqueous solution of sodium hydrogen carbonate was added to neutralize, and the organic phase was extracted. The obtained organic phase was washed with water, and excess toluene was distilled off under reduced pressure. The residue was further recrystallized from hexane and dried under reduced pressure to obtain 34 g (yield: 65%) of the title compound as a solid. IR (KBr): 2930 cm ^-1 (CH), 1730 cm ^-1 (ester), 1630 cm ^-1 (amito)

Production Example 9 Synthesis of N-lauroylalanine ethyl ester 100 g of N-lauroylalanine and 750 m of ethanol
L was placed in a 1000 mL flask, 2 mL of concentrated sulfuric acid was further added as a catalyst, and the mixture was reacted under heating and refluxing for 8 hours. After completion of the reaction, the system was left to room temperature. Excess ethanol was distilled off under reduced pressure. The concentrate is placed in an oil separator and kept at 50 ° C.
About 300 mL of a saturated aqueous sodium hydrogen carbonate solution was added to neutralize the mixture, and the oil phase was extracted. The obtained oil phase was further washed with water, allowed to cool, and then recrystallized from ethanol. By drying under reduced pressure, 81 g of the title compound as a solid (yield 73%)
I got ESI-MS: 300 (M + H) + IR (KBr): 2930 cm ^-1 (CH), 1730 cm ^-1 (ester), 1630 cm ^-1 (amito)

Preparation Example 10 Synthesis of N-lauroylalanine-t-butyl ester 100 g of N-lauroylalanine and t-butanol 75
0 mL was placed in a 1000 mL flask, 2 mL of concentrated sulfuric acid was further added as a catalyst, and the mixture was reacted under heating and refluxing for 8 hours. After completion of the reaction, the system was left to room temperature. Excess t-butanol was distilled off under reduced pressure. Put the concentrate in the oil separator at 50 ° C
, And neutralized by adding about 300 mL of a saturated aqueous solution of sodium hydrogen carbonate, and an oil phase was extracted. The obtained oil phase was further washed with water, allowed to cool, and then recrystallized from ethanol. By drying under reduced pressure, 80 g (yield 70%) of the title compound was obtained as a solid. ESI-MS: 328 (M + H) ⁺ IR (KBr): 2910 cm ^-1 (CH), 1720 cm ^-1 (ester), 1620 cm ^-1 (amito)

Preparation Example 11 Synthesis of N-lauroylalanine propyl ester 100 g of N-lauroylalanine and propanol 750
Then, 2 mL of concentrated sulfuric acid was added as a catalyst, and the mixture was reacted for 8 hours under reflux with heating. After completion of the reaction, the system was left to room temperature. Excess propanol was distilled off under reduced pressure. The concentrate was placed in an oil separator and maintained at 50 ° C., and about 300 mL of a saturated aqueous sodium hydrogen carbonate solution was added to neutralize the oil, and the oil phase was extracted. The obtained oil phase was further washed with water, allowed to cool, and then recrystallized from ethanol. The solid was dried under reduced pressure to obtain 84 g (yield 73%) of the title compound as a solid. ESI-MS: 314 (M + H) ⁺ IR (KBr): 2910 cm ^-1 (CH), 1710 cm ^-1 (ester), 1630 cm ^-1 (amito)

Production Example 12 Synthesis of N-coconut oil fatty acyl sarcosine isopropyl ester 100 g of N-coconut fatty acid acylsarcosine and 750 mL of isopropanol were placed in a 1000 mL flask, 2 mL of concentrated sulfuric acid was further added as a catalyst, and the mixture was heated and refluxed for 8 hours. I let it. After completion of the reaction, the system was left to room temperature. Excess isopropanol was distilled off under reduced pressure. The concentrate was neutralized with 500 mL of a saturated aqueous sodium hydrogen carbonate solution, and the obtained oil phase was further washed with water and dried to obtain 90 g (yield: 78%) of a liquid title compound. IR (neat): 2950 cm ^-1 (CH), 1720 cm ^-1 (ester), 1630 cm ^-1 (amito)

Production Example 13 Synthesis of N-coconut fatty acid acyl-N-methyl-β-alanine isopropyl ester N-coconut fatty acid acyl-N-methyl-β-alanine 8
0 g and 750 mL of isopropanol were put in a 1000 mL flask, 2 mL of concentrated sulfuric acid was further added as a catalyst, and the mixture was reacted under heating and refluxing for 8 hours. After completion of the reaction, the system was left to room temperature. Excess isopropanol was distilled off under reduced pressure. The concentrate was neutralized with about 500 mL of a saturated aqueous sodium hydrogen carbonate solution, and the obtained oil phase was further washed with water. 67 g (yield 73%) of the title compound in a liquid form by drying under reduced pressure
I got IR (neat): 2950 cm ^-1 (CH), 1720 cm ^-1 (ester), 1640 cm ^-1 (Amit II)

Production Example 14 Synthesis of N-lauroyl sarcosine isopropyl ester 100 g of N-lauroyl sarcosine and 750 mL of isopropanol were placed in a 1000 mL flask, 2 mL of concentrated sulfuric acid was further added as a catalyst, and the mixture was heated and refluxed for 8 hours. After completion of the reaction, the system was left to room temperature. After cooling, excess isopropanol was distilled off under reduced pressure. The concentrate was neutralized with about 500 mL of a saturated aqueous sodium hydrogen carbonate solution, and the obtained oil phase was further washed with water and dried under reduced pressure to obtain 98 g (yield: 85%) of the title compound as a colorless transparent liquid. ESI-MS: 314 (M + H) + IR (neat): 2940cm -1 (CH), 1730cm -1 ( ester), 1650 cm ^-1 (Amito Bu)

Production Example 15 Synthesis of N-lauroyl-N-methyl-β-alanine isopropyl ester 100 g of N-lauroyl-N-methyl-β-alanine and 750 mL of isopropanol were placed in a 1000 mL flask, and 2 mL of concentrated sulfuric acid was further used as a catalyst. In addition, the mixture was reacted for 8 hours under heating and reflux. After completion of the reaction, the system was left to room temperature. After cooling, excess isopropanol was distilled off under reduced pressure.
The concentrate is neutralized with 500 mL of a saturated aqueous solution of sodium hydrogen carbonate, and the obtained oil phase is further washed with water and dried to obtain 80 g of the title compound as a transparent liquid (yield 70%).
I got ESI-MS: 328 (M + H) ⁺ IR (neat): 2950 cm ^-1 (CH), 1720 cm ^-1 (ester), 1640 cm ^-1 (Amit II)

Production Example 16 Synthesis of N-lauroylglycine isopropyl ester 60 g of N-lauroylglycine and 75 of isopropanol
0 mL was placed in a 1000 mL flask, 2 mL of concentrated sulfuric acid was further added as a catalyst, and the mixture was reacted under heating and refluxing for 8 hours. After completion of the reaction, the system was left to room temperature. Excess isopropanol was distilled off under reduced pressure. The residue is treated with diethyl ether 300
Dissolve in mL and add saturated sodium bicarbonate aqueous solution 300m
The mixture was neutralized with L, and the obtained organic phase was further washed with water. The extracted organic phase is dried with about 20 g of anhydrous magnesium sulfate,
The anhydrous magnesium sulfate was filtered off. The ether of the obtained mother liquor was distilled off, and the residue was recrystallized with ethanol.
Dry under reduced pressure to obtain 45 g of the title compound as a solid.
(64% yield). ESI-MS: 300 (M + H) ⁺ IR (KBr): 2920 cm ^-1 (CH), 1720 cm ^-1 (ester), 1620 cm ^-1 (amito)

Production Example 17 Synthesis of N-lauroylalanine isopropyl ester 100 g of N-lauroylalanine and isopropanol 7
50 mL was placed in a 1000 mL flask, 2 mL of concentrated sulfuric acid was further added as a catalyst, and the mixture was reacted under heating and refluxing for 8 hours.
After completion of the reaction, the system was left to room temperature. Excess isopropanol was distilled off under reduced pressure. Put the concentrate in the oil separator 5
Keep at 0 ° C, saturated aqueous sodium bicarbonate solution about 300m
L was added to neutralize and the oil phase was extracted. The obtained oil phase was further washed with water and dried under reduced pressure to obtain 83 g (yield 73%) of the title compound as a solid. ESI-MS: 314 (M + H) ⁺ IR (KBr): 2910 cm ^-1 (CH), 1715 cm ^-1 (ester), 1630 cm ^-1 (amito)

Production Example 18 Synthesis of N-lauroyl sarcosine propyl ester 61 g of N-lauroyl sarcosine (manufactured by Kawaken Fine Chemical Co., Ltd.) and 200 mL of 1-propanol were added to 50 parts.
0 mL flask and concentrated sulfuric acid as a catalyst at 1.4
5 g was added, and the mixture was reacted for 7 hours under heating and reflux. After the reaction,
The system was left to room temperature. After cooling, excess 1-propanol was distilled off under reduced pressure. The concentrate was neutralized with 76 g of a 3% aqueous sodium hydroxide solution, and the obtained oil phase was further washed with water,
Drying under reduced pressure gave 48 g (68% yield) of the title compound as a colorless transparent liquid. ESI-MS: 314 (M + H) + IR (neat): 2925cm -1 (CH), 1750cm -1 ( ester), 1650 cm ^-1 (Amito Bu)

Production Example 19 Synthesis of N-lauroyl sarcosine butyl ester 135.5 g of N-lauroyl sarcosine (manufactured by Kawaken Fine Chemical Co., Ltd.) and 200 mL of 1-butanol were placed in a 500 mL flask, and concentrated sulfuric acid was further used as a catalyst. 4.99 g was added and reacted under heating and reflux for 6 hours. After completion of the reaction, the system was left to room temperature. After cooling, excess 1-propanol was distilled off under reduced pressure. The concentrate was neutralized with 162 g of a 3% aqueous sodium hydroxide solution, and the obtained oil phase was further washed with water and dried under reduced pressure to obtain 114 g (70% yield) of the title compound as a colorless transparent liquid. The acid value of the product was 0.6.

Production Example 20 Synthesis of N-lauroylleucine isopropyl ester 49 g of N-lauroylleucine and isopropanol 94
g in a 500 mL flask, 1.61 g of concentrated sulfuric acid was further added as a catalyst, and the mixture was reacted under heating and reflux for 2 hours. After completion of the reaction, excess isopropanol was distilled off under reduced pressure. Further, 94 g of isopropanol was added to the concentrate, and the mixture was reacted under heating and reflux for 5 hours. After completion of the reaction, excess isopropanol was distilled off under reduced pressure. The system was left to room temperature. After cooling down,
The concentrate was neutralized with 87 g of a 3% aqueous sodium hydroxide solution, and the obtained oil phase was further washed with water and dried under reduced pressure to obtain 44 g (yield 79%) of the title compound as a pale yellow transparent liquid. . ^{ESI-MS: 356 (M +} H) + IR (neat): 2925cm -1 (C-H), 1740cm -1 ( ester), 1650 cm ^-1 (Amito Bu)

Preparation Example 21 Synthesis of N-lauroylvaline isopropyl ester 49 g of N-lauroylvaline and 197 of isopropanol
g in a 500 mL flask, 1.61 g of concentrated sulfuric acid was further added as a catalyst, and the mixture was reacted under heating and reflux for 6 hours. After completion of the reaction, excess isopropanol was distilled off under reduced pressure. After standing to cool, the concentrate was neutralized with 77 g of a 3% aqueous sodium hydroxide solution, and the obtained oil phase was further washed with water and dried under reduced pressure to give 41 g of the title compound as a paste to a solid (yield 73%). I got The acid value was 1.5. ESI-MS: 342 (M + H) ⁺ IR (neat): 2925 cm ^-1 (CH), 1720 cm ^-1 (ester), 1640 cm ^-1 (amito II)

Production Example 22 Synthesis of N-coconut oil fatty acid acylleucine isopropyl ester 45 g of N-coconut oil fatty acid leucine and 140 g of isopropanol were placed in a 500 mL flask, and 2.86 g of concentrated sulfuric acid was further added as a catalyst. Allowed to react for hours. After completion of the reaction, excess isopropanol was distilled off under reduced pressure. Further, 90 g of isopropanol was added to the concentrate, and the mixture was reacted under heating and reflux for 1 hour. After completion of the reaction, excess isopropanol was distilled off under reduced pressure. The system was left to room temperature. After allowing to cool, the concentrate was added with 3% aqueous sodium hydroxide solution in 1
The oily phase was neutralized with 48 g, and the obtained oil phase was further washed with water and dried under reduced pressure to obtain 38 g (yield 74%) of the title compound as a pale yellow transparent liquid. The acid value was 1.8. ESI-MS: 356 (M + H) + IR (neat): 2930cm -1 (CH), 1740cm -1 ( ester), 1645 cm ^-1 (Amito Bu)

Reference Example 1 Synthesis of N-lauroylsarcosine isostearyl ester 10 g of N-lauroylsarcosine and 8.6 g of isostearyl alcohol were placed in a 200 mL flask, and 0.5 g of paratoluenesulfonic acid monohydrate was further added as a catalyst. In addition, the reaction was performed at 130 ° C. for 3 hours. After completion of the reaction, the system was left to room temperature. After cooling, about 200 mL of a saturated aqueous sodium hydrogen carbonate solution was added to the system, and the obtained oil phase was further washed with water. The extracted oil phase was added with anhydrous magnesium sulfate,
After sufficiently drying, the solid was filtered off to obtain 16 g (yield: 86%) of the title compound in a liquid form. ^{IR (neat) 2920cm -1 (CH} ), 1720cm -1 ( ester), 1650 cm ^-1 (Amito Bu)

Reference Example 2 Synthesis of N-lauroylsarcosine octyldodecyl ester 10 g of N-lauroylsarcosine and 9.5 g of octyldodecanol were placed in a 200 mL flask, and 0.5 g of paratoluenesulfonic acid was further added as a catalyst at 130 ° C. For 3 hours. After completion of the reaction, the system was left to room temperature. After allowing to cool, the system was saturated with about 20
0 mL was added, and the obtained oil phase was further washed with water. The extracted oil phase was added with anhydrous magnesium sulfate (5 g), dried well, and filtered to obtain 17 g of the liquid title compound.
(87% yield). IR (neat): 2930 cm ^-1 (CH), 1720 cm ^-1 (ester), 1640 cm ^-1 (Amit II)

Reference Example 3 Synthesis of N-lauroylalanine octyldodecyl ester 10 g of N-lauroylalanine and 9.5 g of octyldodecanol were placed in a 200 mL flask, and 0.5 g of paratoluenesulfonic acid was further added as a catalyst.
Allowed to react for hours. After completion of the reaction, the system was left to room temperature.
After allowing to cool, the system is saturated with aqueous sodium bicarbonate solution about 200m
L was added, and the obtained oil phase was further washed with water. The extracted oil phase was added with anhydrous magnesium sulfate (5 g), dried well, and filtered to obtain 16 g (yield: 82%) of a liquid title compound. ^{IR (neat): 2940cm -1 (} CH), 1730cm -1 ( ester), 1650 cm ^-1 (Amito Bu)

Test Example 1 Sensory evaluation of the feel of the N-long-chain acyl neutral amino acid ester obtained in Production Examples and Reference Examples was carried out by five panelists. Each person applied an appropriate amount of each oil-based raw material to the back of the hand and performed a sensory evaluation according to the following evaluation criteria. The properties of each oil agent were liquid as it was, and those of solid agents were once melted by applying heat of about 45 ° C., then the temperature was lowered, and the liquid agent was used for evaluation. The evaluation was made to determine which of the feels of the respective oil agents had a light-feeling sensation such as smooth and refreshing and a heavy-feeling feeling such as moist and sticky. Table 1 shows the evaluation results.

[0054]

[Table 1]

From Table 1, it can be seen that the oily raw materials of the examples have a function that is excellent in refreshing or dry feeling.

Test Example 2 An emulsion containing each oily raw material was prepared according to the formulation shown in Table 2. Five panelists applied an appropriate amount of these emulsions to the back of their hands, and performed a sensory evaluation on freshness, elongation, smoothness, and familiarity based on the following evaluation criteria. The average value of the evaluations of each panel was calculated according to the following evaluation criteria, and a case where the average value was 1.0 to 2.0 was very good (◎), 0.5
The case of less than 1.0 was determined as good (（), and the case of less than -1.0 to 0.5 was determined as poor (△). Table 3 shows the results.

<Evaluation Criteria> 2: Very good, 1: Good, 0: Normal (blank), -1: Bad However, when liquid paraffin was used as the oily raw material, the evaluation score was 0 (Blank).

[0058]

[Table 2]

[0059]

[Table 3]

From Table 3, it can be seen that all of the examples are excellent in refreshing feeling, elongation, smoothness and adaptability as compared with the comparative examples.

Test Example 3 Evaluation of the hair was performed by five panelists. A 0.05% by weight ethanol solution of each oily raw material was prepared. The hair bundle uses the same person's hair, size and weight (2.5g)
Was prepared. Before the evaluation, the sample was washed with about 1000 mL of a 1% by weight aqueous solution of sodium lauryl sulfate (40 ° C.), rinsed with warm water of 40 ° C., and thoroughly dried. The hair bundle was immersed in the above solution for 2 minutes, dried well again, and evaluated for hair conditioning property (good touch). The average value of the evaluation of each panelist according to the following evaluation criteria was calculated, and the average value of 1.0 to 2.0 was very good (◎), and the average value of 0.5 to less than 1.0 was good (○). , -1.0 to less than 0.5 was determined to be defective (△). Table 4 shows the results.

[0062]

[Table 4]

From Table 4, it can be seen that all of the examples are more excellent in hair conditioning property than the comparative examples.

Example 16 (Lotion) A lotion having the composition shown in Table 5 below was prepared by a conventional method.
That is, the components 1 and 2 were respectively dissolved, and the component 2 was mixed with the component 1.

[0065]

[Table 5]

Example 17: (Emollient lotion) An emollient lotion having the composition shown in Table 6 below was prepared as follows. That is, components 1 and 3 were respectively dissolved, and component 3 was added to component 1 and mixed and emulsified. Component 2 was added thereto and emulsified with a homomixer to obtain a product.

[0067]

[Table 6]

Example 18: (W / 0 type emulsion) A W / 0 type emulsion having the composition shown in Table 7 below was prepared by a conventional method.

[0069]

[Table 7]

Example 19: (O / W type cream) An O / W type cream having the composition shown in Table 8 below was prepared as follows. That is, the oil phase was heated to 80 ° C and the aqueous phase was heated to 50 ° C, and the aqueous phase was gradually added to the oil phase while stirring to emulsify.

[0071]

[Table 8]

Example 20: (Emulsion) An emulsion having the composition shown in Table 9 below was prepared as follows. That is, first, components 1, 2 and 3 were each added to 60
The mixture was heated to 0 ° C, and while stirring the component 1, the component 2 was gradually added thereto. Next, the component 3 was gradually added and cooled to 30 ° C.

[0073]

[Table 9]

Example 21: (Emollient cream) An emollient cream having the composition shown in Table 10 below was prepared as follows. First, components 2 and 3 were each added to 50
C. and slowly add component 3 to component 2 to obtain a mixture. The above mixture was uniformly dispersed in a 70 ° C. heated melt of the component 1. Further, the component 4 heated to 70 ° C. was added to the above dispersion with sufficient stirring, and the mixture was emulsified with a homomixer to obtain a product.

[0075]

[Table 10]

Example 22: (Ultraviolet protection essence) An ultraviolet protection essence having the composition shown in Table 11 below was prepared as follows. That is, a humectant, triethanolamine, was dissolved in purified water by heating at 70 ° C. 7 oil
After heating and dissolving at 0 ° C, a surfactant, an ultraviolet absorber, a preservative, and a fragrance were sequentially dissolved, and the mixture was uniformly dissolved at 70 ° C with a homomixer.

[0077]

[Table 11]

Example 23: (Suntan oil) Suntan oil having the composition shown in Table 12 below was prepared by a conventional method.

[0079]

[Table 12]

Example 24: (W / O type foundation cream) A W / O type foundation cream having the composition shown in Table 13 below was prepared as follows. That is, after stirring the component 3, the component 1 sufficiently mixed and pulverized was added, and a homomixer treatment was performed. After dissolving the component 2, the mixture was added to the above mixture and subjected to a homomixer treatment to obtain a product.

[0081]

[Table 13]

Example 25: (Powderary foundation) A powdery foundation having the composition shown in Table 14 below was prepared as follows. That is, first, component 1
(Pigment component) were mixed and pulverized with a pulverizer. Next, this was transferred to a high-speed blender, and the components 2 and 3 were premixed and added to the pigment component, followed by uniform mixing. The grain size was adjusted through a sieve, and the product was obtained by compression molding.

[0083]

[Table 14]

Example 26: (Dual-use foundation) A dual-use foundation having the composition shown in Table 15 below was prepared as follows. That is, component 1 was mixed and pulverized with a pulverizer. Transfer this to a high-speed blender and add ingredient 2
And 3 were added to Component 1 and mixed uniformly. The grain size was adjusted through a sieve, and the product was obtained by compression molding.

[0085]

[Table 15]

Example 27 (blusher) A blusher having the composition shown in Table 16 below was prepared as follows. That is, titanium dioxide, kaolin, iron oxide (red), and red No. 202 were added to a part of the liquid paraffin and dispersed by a roller. After other components were previously mixed and dissolved by heating, all components were uniformly dispersed with a homomixer. After dispersion, the mixture was cooled with stirring to obtain a product.

[0087]

[Table 16]

Example 28: (Emulsion type lipstick) Emulsion type lipstick having the composition shown in the following Table 17 was prepared as follows. That is, titanium dioxide, Red No. 201 and Red No. 202 in Component 1 were added to a part of castor oil and dispersed by a roller. Red No. 223 was dissolved in castor oil. The other components of Component 1 were heated and melted and uniformly dispersed with a pigment and a dye using a homomixer. Component 2 was dissolved by heating, emulsified and dispersed in the above mixture with a homomixer, poured into a mold and quenched to form a stick.

[0089]

[Table 17]

Example 29: (Lipstick) A lipstick having the composition shown in Table 18 below was prepared as follows. That is, component 2 is heated and dissolved, component 1 is added thereto, kneaded with a roll mill, uniformly dispersed, and defoamed.
The mixture was poured into a mold and quenched to form a stick.

[0091]

[Table 18]

Example 30: (Eyebrow) An eyebrow having the composition shown in Table 19 below was prepared as follows. That is, the powder component of the component 1 was mixed well with a blender, dispersed with a heat-melted other component using a pulverizer, and then compression-molded to obtain a product.

[0093]

[Table 19]

Example 31: (O / W type foundation cream) An O / W type foundation cream as shown in Table 20 below was prepared as follows. That is, propylene glycol in which bentonite in Component 2 was dispersed was added to purified water, and the mixture was homomixed at 70 ° C., and then the remaining Component 2 was added and sufficiently stirred. The mixed and pulverized component 1 was added thereto with stirring, and homogenized at 70 ° C. Next, the component 3 heated at 70 to 80 ° C. was gradually added, and the mixture was homogenized at 70 ° C. and cooled to room temperature to obtain a product.

[0095]

[Table 20]

Example 32: (Conditioning shampoo) A conditioning shampoo having the composition shown in Table 21 below was prepared as follows. That is, cationized cellulose was added to purified water, heated and stirred to raise the temperature to 70 ° C. Other components were added to the mixture, stirred and dissolved, and cooled to obtain a product.

[0097]

[Table 21]

Example 33: (Rinse-in shampoo) A rinse-in shampoo having the composition shown in Table 22 below was prepared as follows. That is, stearyltrimethylammonium chloride and an amphoteric surfactant were added to purified water, dissolved by heating, kept at 70 ° C., the remaining components were added, dissolved, and cooled to obtain a product.

[0099]

[Table 22]

Example 34: (Heart treatment cream) A hair treatment cream having the composition shown in Table 23 below was prepared as follows. That is, components 1 and 2
Was heated to 80 ° C., and component 1 was gradually added while stirring component 2, followed by cooling to obtain a product.

[0101]

[Table 23]

Example 35: (Hair lotion) A hair lotion having the composition shown in Table 24 below was prepared as follows. That is, each of components 1 and 2 is 8
The mixture was heated to 0 ° C., and component 1 was gradually added while stirring component 2, followed by cooling to obtain a product.

[0103]

[Table 24]

Example 36: (Cleansing foam) A cleansing foam having the composition shown in Table 25 below was prepared as follows. That is, the components 1 and 2 were each heated to 80 ° C., and the component 1 was gradually added while stirring the component 2, followed by cooling to obtain a product.

[0105]

[Table 25]

Example 37: (Cleansing oil) A cleansing oil having the composition shown in Table 26 below was prepared by a conventional method.

[0107]

[Table 26]

Example 38: (Make Remover) Makeup removers as shown in Table 27 below were prepared as follows. That is, each of components 1 and 2 was heated to 80 ° C.
The mixture was heated until the mixture was stirred, and the mixture was gradually added to the mixture while stirring the mixture, followed by cooling to obtain a product.

[0109]

[Table 27]

Example 39: (Shaving foam) Glycerin, triethanolamine and the compound of Production Example 12 were added to purified water and heated to 70 ° C. to obtain an aqueous phase. The other components were dissolved by heating to obtain an oil phase. The oil phase was added to the aqueous phase to perform a neutralization reaction. For filling, a stock solution was added to the can, and after mounting the valve, gas was filled.

[0111]

[Table 28]

Example 40: (Liquid detergent) A liquid detergent having the composition shown in Table 29 below was prepared by a conventional method.

[0113]

[Table 29]

Example 41: (bath oil) A bath oil having the composition shown in Table 30 below was prepared by a conventional method.

[0115]

[Table 30]

Example 42: (Soap) A soap having the composition shown in Table 31 below was prepared by a conventional method.

[0117]

[Table 31]

Example 43: (Setting agent) A setting agent having the composition shown in Table 32 below was prepared. That is, other components were dissolved in ethyl alcohol and filtered.
After filtration, the can was filled with the undiluted solution, and a gas was filled after the valve was attached.

[0119]

[Table 32]

Example 44: (Perm solution) A perm solution having the composition shown in Table 33 below was prepared by a conventional method.

[0121]

[Table 33]

Example 45: (Facial cleanser) A facial cleanser having the composition shown in Table 34 below was prepared by a conventional method. That is, the components 1 and 2 were each heated to 80 ° C., and the component 1 was gradually added while stirring the component 2, followed by cooling to obtain a product.

[0123]

[Table 34]

Example 46: (Hair dye) A hair dye having the composition shown in Table 35 below was prepared by a conventional method.

[0125]

[Table 35]

As described above, the cosmetics of Examples 16 to 46 were excellent in the conditioning effect on the hair and the feeling on use on the skin.

The cosmetic composition comprising the N-long-chain acyl-neutral amino acid ester of the present invention is excellent in feeling of refreshing, spreading, conforming, smoothness and the like on the skin,
It also has an excellent conditioning effect on hair.

──────────────────────────────────────────────────の Continued on the front page (51) Int.Cl. ⁶ Identification code FI A61K 7/025 A61K 7/025 7/031 7/031 7/032 7/032 7/035 7/035 7/06 7/06 7/42 7/42 7/50 7/50

Claims (4)

[Claims] 1. An ester of an N-long-chain acyl-neutral amino acid having a straight-chain or branched-chain saturated or unsaturated acyl group having 6 to 22 carbon atoms, wherein the ester group is a hydrocarbon group. Is a linear or branched saturated or unsaturated hydrocarbon group having 1 to 10 carbon atoms, N-long-chain acyl neutral amino acid ester. 2. The oily raw material for cosmetics according to claim 1, wherein the N-long-chain acyl neutral amino acid ester is represented by the following general formula (1). Embedded image (Wherein, R ¹ represents a branched or straight-chain alkyl group or alkenyl group having 5 to 21 carbon atoms, and R ² represents a hydrogen atom or a straight-chain or branched alkyl group having 1 to 3 carbon atoms. R ³ represents a hydrogen atom or a linear or branched alkyl group having 1 to ⁴ carbon atoms, R ⁴ represents a branched or linear alkyl or alkenyl group having 1 to 10 carbon atoms,
n shows the integer of 0-2. ) 3. A cosmetic composition comprising at least one of the oily raw materials for cosmetics according to claim 1. 4. An N-long-chain acyl neutral amino acid ester represented by the following general formula (1). Embedded image (Wherein, R ¹ represents a branched or straight-chain alkyl group or alkenyl group having 5 to 21 carbon atoms, R ² represents a straight-chain or branched alkyl group having 1 to 3 carbon atoms, ³ represents a hydrogen atom or a linear or branched alkyl group having 1 to ⁴ carbon atoms; R ⁴ represents a branched or linear alkyl or alkenyl group having 2 to 10 carbon atoms; Represents an integer of 2 to 2)