JP2002316971A - Gelatinizing agent of oily base - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a gelatinizing agent having excellent gelatinizing performance to an oily base, and capable of producing a gel-shaped composition having excellent gel strength and transparency. SOLUTION: This compound is represented by the formula (I) (R<1> and R<2> are each a 1-26C hydrocarbon group, preferably a linear or branched alkyl group; R<3> is a 7-10C hydrocarbon group, preferably a linear or branched alkyl group; n is 1 or 2; and the acidic amino acid residue in the molecule is an L-aspartic acid residue when n is 1, or an L-glutamic acid residue when n is 2). The gelatinizing agent of the oily base contains the compound.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a gelling agent for an oily base. More specifically, the present invention relates to an oil-based gelling agent containing a specific amino acid derivative. The gelling agent of the present invention is useful for diversifying the form by gelling an oily base that is liquid at room temperature.

[0002]

2. Description of the Related Art Conventionally, gelling agents for oil-based bases that are not soluble in water include polyamide resins, aromatic aldehydes typified by 12-hydroxystearic acid and dibenzylidene-D-sorbitol, and polyhydric aldehydes. Condensates with alcohols are known. However, these gelling agents have a problem of low solubility in an oily base. For example, a gel composition prepared using these gelling agents has a poorly dissolved state, and the gel composition becomes non-uniform, or the gelled oily base oozes out of the surface of the gel due to a change over time, the so-called “gel composition”. There is a problem that a "sweating phenomenon" occurs.

[0003] Other gelling agents for oily bases include N-lauroyl-glycol disclosed in Japanese Patent Application Laid-Open No. 51-19139.
L-glutamic acid dibutylamide is known, and cosmetics containing this substance as a gelling agent have been reported. This gelling agent is known to be capable of gelling various oily bases, but the resulting gel composition does not always have sufficient gel strength, and is used as a cosmetic for application to the skin. When the gel composition was prepared, the dosage form was brittle, and a problem sometimes occurred in terms of strength.

Further, US Pat. No. 5,591,424 and Japanese Patent Publication No. 7-506833 report an antiperspirant gel stick containing 12-hydroxystearic acid and N-lauroylglutamic acid dibutylamide. However, this gel stick also has insufficient gel strength,
In some cases, application to the skin became difficult. Further, the appearance of each of the gel compositions obtained by using these gelling agents and the oily bases is white and lacks transparency, which is not preferable from an aesthetic viewpoint.

[0005]

SUMMARY OF THE INVENTION An object of the present invention is to provide a gelling agent for an oily base. More specifically, it is an object of the present invention to provide a gelling agent having an excellent gelling ability for an oily base. It is another object of the present invention to provide a gelling agent capable of producing a gel composition having excellent gel strength and transparency. Still another object of the present invention is to provide a gel composition containing a gelling agent having the above characteristics and an oily base, and having excellent gel strength and transparency.

[0006]

The present inventors have conducted intensive studies to solve the above-mentioned problems, and as a result, it has been found that a specific acidic amino acid derivative has extremely excellent properties as a gelling agent for an oily base. The present inventors have found that a gel composition prepared from this acidic amino acid derivative and an oily base has excellent gel strength and high transparency. In addition, they have found that the obtained gel composition has sufficient strength to be used as a cosmetic, and can be easily applied to the skin even when molded into a stick shape or the like. The present invention has been completed based on the above findings.

That is, the present invention provides the following general formula (I):

Embedded image (Wherein, R ¹ and R ² each independently have 1 to 2 carbon atoms)
6 represents a hydrocarbon group, R ³ represents a hydrocarbon group having 7 to 10 carbon atoms, n represents 1 or 2, and the acidic amino acid residue in the molecule is L-asparagine when n is 1. An acid residue, and when n is 2, it represents an L-glutamic acid residue).

According to a preferred embodiment of the present invention, R ¹ and R ² are each independently a straight-chain or branched-chain alkyl group having 1 to 26 carbon atoms, and R ³ is a group having 7 to 10 carbon atoms.
Is a linear or branched alkyl group, wherein n is 2;
¹ and R ² are each independently a linear or branched alkyl group having 3 to 5 carbon atoms, R ³ is a linear or branched alkyl group having 7 to 9 carbon atoms, n Is provided. According to a particularly preferred embodiment of the present invention, the compound included in the above general formula (I) is N-2
-Ethylhexanoyl-L-glutamic acid dibutylamide, N-octanoyl-L-glutamic acid dibutylamide, or N-decanoyl-L-glutamic acid dibutylamide is provided.

From another viewpoint, according to the present invention, a gelling agent for an oily base containing at least one of the compounds represented by the general formula (I); and a compound represented by the general formula (I) An oil-based gelling agent comprising at least one compound and N-lauroyl-L-glutamic acid dibutylamide is provided. As a preferred example of the latter, the total weight of the compound represented by the general formula (I) and N-lauroyl-L
-The ratio to the weight of glutamic acid dibutylamide is 35: 5.
~ 5: 35 is provided by the present invention.

In another aspect, the present invention provides a gel composition containing (a) the above-mentioned gelling agent, and (b) at least one oleaginous base. In a preferred embodiment of the gel composition, the gel composition which is a translucent composition and the gel composition further comprising (c) at least one antiperspirant active ingredient are provided. Further, according to the present invention, there is provided a cosmetic containing the gel composition. This cosmetic may be preferably formed into a stick shape.

Further, according to the present invention, there is provided a method for gelling an oily base, comprising at least one compound represented by the above general formula (I) and, if necessary, N-lauroyl-L.
A method comprising the step of mixing glutamic acid dibutylamide with an oily base; a method for producing a gel composition containing an oily base, wherein at least one of the compounds represented by the above general formula (I) is required A process of mixing N-lauroyl-L-glutamic acid dibutylamide with an oily base according to the method of the present invention for the production of a gel composition containing an oily base. Use provided.

[0012]

BEST MODE FOR CARRYING OUT THE INVENTION In the general formula (I), R ¹ and R ² each independently represent a hydrocarbon group having 1 to 26 carbon atoms. The hydrocarbon group represented by R ¹ and R ² may be linear, branched, cyclic, or a combination thereof. Although a hydrocarbon group containing an unsaturated bond can be used as the hydrocarbon group, it is more preferable to use an alkyl group. Preferably, a linear or branched alkyl group having 1 to 10 carbon atoms, more preferably 2 to 6 carbon atoms can be used, and still more preferably a linear alkyl group having 3 to 5 carbon atoms. Or a branched alkyl group.
Most preferably, an n-butyl group can be used.

R ³ represents a hydrocarbon group having 7 to 10 carbon atoms. Hydrocarbon group R ³ represents straight-chain, branched, may be cyclic, or a combination thereof.
Although a hydrocarbon group containing an unsaturated bond can be used as the hydrocarbon group, it is more preferable to use an alkyl group. As the alkyl group, a linear or branched alkyl group is preferable. More preferably, R ³ has 7 to 7 carbon atoms.
9 represents a linear or branched alkyl group. R ³ -C
Examples of the group represented by O- include, for example, an n-octanoyl group, an n-nonanoyl group, an n-decanoyl group, an n-undecanoyl group, a 2-ethylhexanoyl group, and the like. Octanoyl, decanoyl and 2-ethylhexanoyl are preferred, and 2-ethylhexanoyl is most preferred from the viewpoint of exhibiting high gelling ability on various oil-based substrates. R ³ -CO-
When the group represented by is a 2-ethylhexanoyl group, a 2- (R, S) -ethylhexanoyl group may be used from the viewpoint of easy availability of the raw material 2-ethylhexanoyl chloride. preferable. In the general formula (I), n is 2
It is preferable that

In the compound represented by the general formula (I),
The acidic amino acid residue in the molecule indicates L-aspartic acid residue when n is 1, and L-glutamic acid residue when n is 2. The compound represented by the general formula (I) includes R ¹ ,
Depending on the type of R ² and / or R ³ , the compound may have one or more asymmetric carbons, and stereoisomers such as optical isomers or diastereomers based on such asymmetric carbons, arbitrary stereoisomers And racemates are included in the scope of the present invention. When R ¹ , R ² , and / or R ³ has an olefinic double bond, the configuration is Z or E
And geometric isomers or mixtures of any geometric isomers are included in the scope of the present invention. Further, the scope of the present invention includes any hydrate and any form of crystals of the compound represented by the above general formula (I). As the gelling agent of the present invention, any of the above-mentioned isomers, mixtures thereof, or hydrates can be used.

The compound represented by the general formula (I) can be obtained, for example, by reacting a long-chain fatty acid halide with L-glutamic acid or L-aspartic acid by a Schotten-Baumann reaction in the presence of a basic catalyst to give N-acylated glutamic acid. Alternatively, it can be produced by producing an N-acylated aspartic acid and further heating and reacting an amine derivative such as an alkylamine in the presence or absence of an acid catalyst. Alternatively, glutamic acid amide or aspartic acid amide obtained by reacting glutamic acid or aspartic acid with an amine derivative such as an alkylamine in the presence or absence of an acid catalyst is reacted with an acylating agent such as a fatty acid halide to give N-
It can be produced by acylation.

The preparation examples of the compound represented by the general formula (I) are specifically and specifically described in the working examples of the present specification, and the starting materials, the reagents, and the reaction conditions will be described with reference to the preparation examples. A person skilled in the art can produce any of the compounds represented by the general formula (I) by appropriately selecting and the like, and adding appropriate modifications and alterations to those methods as necessary.

The gelling agent of the present invention has the general formula (I)
One compound selected from the compounds represented by formula (I) may be used, or two or more compounds selected from the compounds represented by formula (I) may be used in combination. The use amount of the gelling agent of the present invention is not particularly limited as long as the oily base is gelled, but usually the oily base 1 to be gelled is used.
0.1 to 15 parts by weight, preferably 1 to 100 parts by weight
About 10 to 10 parts by weight. If the amount is less than 0.1 part by weight, sufficient gel strength may not be obtained,
If the amount is more than 5 parts by weight, the gelled oily base cannot be dissolved in the oily base and the appearance of the obtained gelled oily base may be impaired.

The gelling agent of the present invention may contain N-lauroyl-L-glutamic acid dibutylamide in addition to one or more compounds selected from the compounds represented by formula (I). Good. When this gelling agent is used, a gel composition having high gel strength and relatively high transparency (translucent) can be obtained. In this case, the general formula (I)
(In the present specification, the “total weight” refers to the weight of a compound when one kind of compound is used, and the total weight thereof when two or more kinds of compounds are contained. ) And N-lauroyl-L-glutamic acid dibutylamide can be appropriately selected according to the desired performance, but is generally preferably 35: 5 to 5:35. The amount of the gelling agent containing N-lauroyl-L-glutamic acid dibutylamide is the same as that described above, and the amount of the oily base 100 to be gelled is 100%.
0.1 to 15 parts by weight, preferably 1 to 1 part by weight
0 parts by weight. In addition, N-lauroyl-L-glutamic acid dibutylamide used in the present invention can be produced by the same method as the compound represented by the above general formula (I), and a commercially available product from Ajinomoto Co., Inc. (Product name "GP-1").

The oily base used in the gel composition of the present invention is not particularly limited as long as it dissolves the above gelling agent sufficiently by heating and forms a gel when cooled to room temperature. Specific examples include silicone oils; higher alcohols such as cetyl alcohol, isostearyl alcohol, lauryl alcohol, hexadecyl alcohol, and octyl dodecanol; fatty acids such as isostearic acid, undecylenic acid, and oleic acid; glycerin, sorbitol, ethylene glycol, Propylene glycol,
Polyhydric alcohols such as polyethylene glycol; myristyl myristate, hexyl laurate, decyl oleate, isopropyl myristate, hexyl decyl dimethyloctanoate, glyceryl monostearate, diethyl phthalate, ethylene glycol monostearate, octyl oxystearate, etc. Esters of liquid; hydrocarbons such as liquid paraffin, vaseline, and squalane; waxes such as lanolin, reduced lanolin, and carnauba wax; oils and fats such as mink oil, cocoa oil, coconut oil, palm kernel oil, camellia oil, sesame oil, castor oil, and olive oil. ; Ethylene, α-olefin,
Cooligomers and the like.

Examples of the silicone oil include methylpolysiloxane, highly polymerized methylpolysiloxane, polyoxyethylene / methylpolysiloxane copolymer, polyoxypropylene / methylpolysiloxane copolymer and poly (oxyethylene, oxypropylene). Ether modified silicone such as methylpolysiloxane copolymer, stearoxymethylpolysiloxane, stearoxytrimethylsilane, methylhydrogenpolysiloxane, octamethylpolysiloxane, decamethylpolysiloxane, decamethylcyclopentasiloxane, octamethylcyclotetra Cyclic silicones such as siloxane, tetrahydrotetramethylcyclotetrasiloxane, methylcyclopolysiloxane, cyclopentasiloxane and dodecamethylcyclohexasiloxane ; Methylphenyl polysiloxane,
Amino-modified silicone such as trimethylsiloxysilicic acid, aminoethylaminopropylsiloxane / dimethylsiloxane copolymer, silanol-modified polysiloxane, alkoxy-modified polysiloxane, fatty acid-modified polysiloxane, fluorine-modified polysiloxane, epoxy-modified polysiloxane, alkoxy-modified polysiloxane Siloxane perfluoropolyether, polyvinyl acetate dimethylpolysiloxane,
And mixtures thereof.

The oil base is preferably used in a proportion of about 10 to 99.9% by weight based on the total weight of the gel composition. When the amount of the oily base is less than 10% by weight,
Or, when it is more than 99.9% by weight, sufficient gel strength may not be obtained.

The gel composition of the present invention may further contain an antiperspirant active ingredient. As used herein, the term “antiperspirant active ingredient” refers to an ingredient that suppresses the generation of sweat by converging the skin, but this term should be interpreted in the broadest sense, and is limited in any sense. Do not interpret. The type of antiperspirant active ingredient is not particularly limited, and two or more antiperspirant active ingredients may be used in combination. As the antiperspirant active ingredient, for example, manufactured by reacting chlorohydroxyaluminum, aluminum chloride, allantoinchlorohydroxyaluminum, aluminum sulfate, zinc oxide, zinc paraphenolsulfonate, zirconyl chloride with aluminum hydroxide and aluminum chloride hydroxide. Zirconium-aluminum composite. The antiperspirant active ingredient can be blended in an amount of 1 to 60% by weight, preferably 5 to 35% by weight based on the total weight of the gel composition.
Further, the antiperspirant active ingredient may be incorporated in any form of a solution or a powder. When used in powders, generally the particle size of the substance that is the antiperspirant active is 1-100 microns,
It is preferably about 1 to 50 microns and preferably has a high bulk density.

The method for producing the gel composition of the present invention is not particularly limited. For example, the above-mentioned gelling agent and oily base are stirred for about 50 hours until the mixture forms a uniform solution.
The desired gel composition can be obtained by heating to about 180 ° C. and then cooling.

The gel composition of the present invention can be used as a cosmetic. When the gel composition of the present invention is used as a cosmetic, the gel composition may be used as it is, but it is generally possible to mix and use various components usually used in the production of cosmetics. preferable.

Examples of the components to be added to the cosmetic include various chelating agents for maintaining the efficacy of the above-mentioned antiperspirant active component and suppressing discoloration and generation of odor. The type of chelating agent is not particularly limited, but is preferably triethylenetetramine, 1,1,1-trifluoro-3,
2'-thenoyl acetone, thioglycolic acid, tartaric acid,
Succinic acid, 8-quinolinol, pyridine-2,6-dicarboxylic acid, pyridine, 1,10-tenanthroline, lactic acid, 8-hydroxyquinoline-5-sulfonic acid, glycine, 2,2′-pyridylethylenediamine, xylenol orange, 5-sulfosalicylic acid, salicylic acid, pyrocatechol-3,5-disulfonate, 4,5-dihydroxybenzene-1,3-disulfonic acid, 1,2-diaminocyclohexane-N, N, N ', N'-tetraacetic acid , Citric acid, oxalate, nitrilotriacetic acid, ethylenediamine-N, N, N ', N'-tetraacetic acid, chelating agents selected from the group consisting of acetylacetone and salts thereof, and mixtures thereof.

As other compounding ingredients which can be compounded in cosmetics,
In addition to the gelling agent of the present invention, one or more oil-based gelling agents can be used in combination. For example, polyamide resin, 1
2-hydroxystearic acid, sodium stearate, dibenzylidene-D-sorbitol, N-lauroyl-L-glutamic acid dibutylamide and the like.

The cosmetic of the present invention may further comprise a surfactant as another component as long as the effect of the present invention is not impaired.
Various additives and various powders can be blended. As the surfactant, any of an anionic surfactant, a nonionic surfactant, a cationic surfactant, and an amphoteric surfactant may be used. Examples of the anionic surfactant include N-long-chain acyl amino acid salts such as N-long-chain acyl acidic amino acid salts and N-long-chain acyl neutral amino acid salts, N-long-chain fatty acyl-N-methyltaurine salts, Alkyl sulfate and its alkylene oxide adducts, fatty acid amide ether sulfates, metal salts and weak base salts of fatty acids, sulfosuccinic surfactants, alkyl phosphates and their alkylene oxide adducts, alkyl ether carboxylic acids and the like can be mentioned. . Nonionic surfactants include, for example, ether surfactants such as glycerin ether and its alkylene oxide adduct, ester surfactants such as glycerin ester and its alkylene oxide adduct, sorbitan ester and its alkylene oxide addition Ester type surfactants such as ether ester type surfactants, polyoxyalkylene fatty acid ester, glycerin ester, fatty acid polyglycerin ester, sorbitan ester, sucrose fatty acid ester, alkyl glucosides, hydrogenated castor oil pyroglutamic acid diester and the like. Examples thereof include nitrogen-containing nonionic surfactants such as ethylene oxide adducts and fatty acid alkanolamides. Examples of the cationic surfactant include aliphatic amine salts such as alkyl ammonium chloride and dialkyl ammonium chloride;
Aromatics such as quaternary ammonium salts and benzalkonium salts
Quaternary ammonium salts, fatty acyl arginine esters and the like.Examples of the amphoteric surfactant include betaine-type surfactants such as carboxybetaine,
Examples thereof include aminocarboxylic acid type surfactants and imidazoline type surfactants.

As various additives, for example, glycine,
Amino acids such as 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 and polyaspartic acid Including polyamino acids and salts thereof, polyethylene glycol, gum arabic, alginates, xanthan gum, hyaluronic acid, hyaluronate,
Chitin, chitosan, water-soluble chitin, carboxyvinyl polymer, carboxymethylcellulose, hydroxyethylcellulose, hydroxypropyltrimethylammonium chloride, poly (dimethylmethylenepiperidium chloride), quaternary ammonium polyvinylpyrrolidone derivative, cationized protein, collagen degradation products and derivatives, acyl Water-soluble polymers such as protein and polyglycerin; sugar alcohols such as mannitol and alkylene oxide adducts thereof; lower alcohols such as ethanol and propanol; animal and plant extracts; nucleic acids; vitamins; enzymes; Agents, preservatives, antioxidants, ultraviolet absorbers, chelating agents, antiperspirants, pigments, pigments, oxidation dyes, organic and inorganic powders, pH adjusters, pearling agents, wetting agents, and the like. Kill.

Examples of various powders include resin powders such as nylon beads and silicone beads, nylon powder, metal fatty acid soap, yellow iron oxide, red iron oxide, black iron oxide, chromium oxide, cobalt oxide, carbon black, and the like. Ultramarine, navy blue, zinc oxide, titanium oxide, zirconium oxide,
Silicon oxide, aluminum oxide, cerium oxide, mica titanium, boron nitride, barium sulfate, calcium carbonate, magnesium carbonate, aluminum silicate, magnesium silicate,
Silicon carbide, pigment, lake, sericite, mica, talc, kaolin, barium sulfate plate, barium sulfate butterfly, fine particle titanium oxide, fine particle zinc oxide, fine particle iron oxide, acyl lysine, acyl glutamic acid, acyl arginine, acyl glycine, etc. Acyl amino acids and the like. These powders are further treated with a silicone, a fluorine compound, a silane coupling agent, a silane-treated organic titanate, an acylated lysine, a fatty acid,
Powders that have been subjected to a surface treatment such as a metal soap treatment, an oil treatment, and an amino acid treatment may be used.

The use of the cosmetic of the present invention is not particularly limited. For example, it can be used as a cosmetic in the form of a gel cosmetic, a pack cosmetic, a granular cosmetic or the like. The cosmetic composition of the present invention may be prepared as a uniform composition by preparing the above gel composition and then adding and mixing one or more of the additives described above as necessary. it can. The production process is not particularly limited, and general-purpose means such as mixing, stirring, and kneading available to those skilled in the art can be appropriately used.

[0031]

EXAMPLES Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited to the following examples.

Example 1 Preparation of N-2- (R, S) -ethylhexanoyl-L-glutamic acid dibutylamide 110 g of sodium glutamate monohydrate was added to water 140
g and 27% aqueous sodium hydroxide solution 78 g, and cooled to 10 ° C. After adding 110 g of acetone,
87 g of 2-ethylhexanoyl chloride and 78 g of a 27% aqueous sodium hydroxide solution were added dropwise. The acylation reaction solution was diluted with 100 g of water, and neutralized with 63 g of 95% sulfuric acid.
An oil separated. The aqueous layer was removed, and the oil layer was concentrated under reduced pressure to obtain an oily substance. This oily substance was dissolved in 742 g of methanol, 6.2 g of 95% sulfuric acid was added, and the mixture was refluxed for 9 hours. The reaction solution was allowed to cool to 35 ° C., neutralized with 8.8 g of n-butylamine, and methanol was distilled off to obtain an oily substance. To this oily substance, 643 g of toluene and 271 g of n-butylamine were added, and the mixture was heated with stirring at 90 ° C. for 10 hours. Hot water 5
06 g and 130 g of 95% sulfuric acid were added to separate oil,
The aqueous layer was removed. 1200 g of warm water was added to the oil layer, and the solvent was removed at normal pressure to obtain a white solid slurry. The solid was filtered and dried in vacuo at 50 ° C. to obtain 2-ethylhexanoylglutamic acid dibutylamide. (A) ¹³ C-NMR peak (solvent CDCl ₃ ): 12.
04, 12.07, 13.74, 13.96, 13.9
9, 20.08, 20.11, 22.70, 22.7
4, 26.01, 29.83, 31.56, 31.6
0, 32.37, 33.05, 39.29, 39.5
3, 49.37, 52.53, 52.56, 171.2
^{9,173.03,176.66 (ppm) (b) 1} H-NMR peaks (CDCl ₃₎ δ: 3.24
8 (m, 4H), 4.373 (m, 1H), 6.199
(Brs, 1H), 7.079 (brs, 1H), 7.
169 (brs, 1H) (c) Wave number of infrared absorption spectrum: 3291.7, 2
961.0, 2932.5, 1638.2, 1551.
2,1452.6 (cm ^-1 ) (d) MS spectrum: 382.3 (MH) ^-

Example 2 Preparation of N-octanoyl-L-glutamic acid dibutylamide 110 g of sodium glutamate monohydrate was added to water 140
g and 27% aqueous sodium hydroxide solution 78 g, and cooled to 10 ° C. After adding 110 g of acetone,
87 g of octanoyl chloride and 90 g of a 27% aqueous sodium hydroxide solution were added dropwise. 100 g of acylation reaction solution
Of water, neutralized with 64 g of 95% sulfuric acid, and separated into oil. The aqueous layer was removed, and the oil layer was concentrated under reduced pressure to obtain an oily substance. This oily substance was dissolved in 742 g of methanol,
6.2 g of sulfuric acid was added, and the mixture was refluxed for 9 hours. Reaction solution was 35
The mixture was allowed to cool to 中 和 C, neutralized with 10.5 g of n-butylamine, and methanol was distilled off to obtain an oily substance. The oily substance was added with 630 g of toluene and 191 g of n-butylamine, and heated and stirred at 90 ° C. for 10 hours. 500 hot water
g and 178 g of 95% sulfuric acid were added to separate oil, and the aqueous layer was removed. 645 g of warm water was added to the oil layer, and the solvent was removed at normal pressure to obtain a white solid slurry. This solid was filtered and dried under vacuum at 50 ° C. to obtain octanoylglutamic acid dibutylamide. (A) ¹³ C-NMR peaks: 14.10, 14.43,
20.44, 22.98, 26.07, 29.38, 2
9.61, 29.86, 31.92, 31.97, 3
2.06, 33.44, 37.07, 39.69, 3
9.88, 52.91, 171.61, 173.33,
174.17 (ppm) (b) ¹ H-NMR peak (CDCl ₃ ) δ: 3.24
7 (m, 4H), 4.360 (m, 1H), 6.201
(Brs, 1H), 6.987 (brs, 1H), 7.
039 (brs, 1H) (c) Wave number of infrared absorption spectrum: 3292.8, 2
958.3, 2930.4, 1640.1, 1543.
0, 1450.3 (cm ^-1 ) (d) MS spectrum: 382.3 (M-H) ^-

Example 3: Method for producing N-decanoyl-L-glutamic acid dibutylamide According to the method of Example 1 described above, decanoylglutamic acid dibutylamide was produced. (A) ¹³ C-NMR peaks: 14.10, 14.47,
20.44, 20.48, 23.04, 26.07, 2
9.65, 29.67, 29.73, 29.83, 2
9.88, 31.92, 31.97, 32.24, 3
7.08, 39.70, 39.88, 52.90, 17
1.60, 173.33, 174.17 (ppm) (b) ¹ H-NMR peak (CDCl ₃ ) δ: 3.25
0 (m, 4H), 4.360 (m, 1H), 6.190
(Brs, 1H), 6.980 (brs, 1H), 7.
030 (brs, 1H) (c) Wave number of infrared absorption spectrum: 3294.8, 2
959.0, 2927.5, 1637.9, 1556.
0,1466.6 (cm ^-1 ) (d) MS spectrum: 410.5 (M-H) ^-

Incidentally, ethyloyl glutamic acid dibutyl amide, hexanoyl glutamic acid dibutyl amide, myristoyl glutamic acid dibutyl amide and palmitoyl glutamic acid dibutyl amide used in the following comparative examples were produced in the same manner.

Examples 4 to 6: Preparation of Gel Composition 0.2 g of various N-acylglutamic acid dibutylamides shown in Table 1 were put in 20 g of various oily bases, and dissolved by heating in an oil bath at 150 ° C. for 15 hours. The mixture was allowed to cool at 23 ° C. to obtain a gel composition. The gel strength of the obtained gel composition was measured with a rheometer (FUDOH RHEO METER NRM).
-2010-J-CW). Adapter is cylindrical type, 10φ, sample stage speed is 6cm / min
And The results are shown in Table 1. As is clear from Table 1, N-2- (R, S) -ethylhexanoyl-L-
Glutamic acid dibutylamide, N-octanoyl-L-
Glutamic acid dibutylamide and N-decanoyl-L
-Glutamic acid dibutylamide has a higher gelling ability than other gelling agents, and can exhibit excellent gelling ability irrespective of the type of oil base.

[0037]

[Table 1]

Examples 7 to 10: Production of gel compositions 0.4 g of various gelling agents shown in Table 2 were placed in 20 g of an oily base, and dissolved by heating in an oil bath at 150 ° C for 15 hours.
The mixture was allowed to cool at 3 ° C. to obtain a gel composition. The gel strength of the obtained gel composition was measured with a rheometer (FUDOH RHEO).
METER NRM-2010-J-CW). The adapter used was a cylindrical type, 10φ, and the sample stage speed was 6 cm / min. Further, the transparency of the obtained gel composition was visually determined. The results are shown in Table 2.
It can be seen that Examples 7 to 9 have higher gel strength than Comparative Examples 6 to 8. In addition, it can be seen that Examples 8 to 10 have higher transparency than Comparative Examples.

[0039]

[Table 2]

Examples 11 to 12: Production of antiperspirant gel sticks Various gelling agents shown in Table 3 were dissolved in an oily base by heating.
Aluminum zirconium trichlorohydrex glycine was added, and the mixture was allowed to cool with stirring to obtain a publication-suppressing gel stick. The gel strength of the obtained publication suppressing gel stick was measured using a rheometer (FUDOH RHEO MET).
ERNRM-2010-J-CW). Adapter is cylindrical type, using 10φ, sample stage speed is 6cm
/ Min. The results are shown in Table 3. It was found that the gel sticks of Examples 11 and 12 had higher gel strength than the comparative example, and that an excellent antiperspirant could be obtained.

[0041]

[Table 3]

Example 13: Preparation of lipstick A lipstick was prepared according to the recipe shown in Table 4 by a conventional method. The prepared lipstick was excellent in strength and free of perspiration.

[0043]

[Table 4]

Example 14: Production of transparent lipstick A transparent lipstick was prepared according to the formulation shown in Table 5 by a conventional method. The prepared transparent lipstick was excellent in strength, had high transparency in appearance, and was stable.

[0045]

[Table 5]

Example 15: Production of candle A candle was prepared according to the recipe shown in Table 6 by a conventional method. The prepared candle was excellent in strength and highly transparent in appearance.

[0047]

[Table 6]

[0048]

By using the gelling agent of the present invention to gel an oily base, a gel composition having high gel strength and excellent transparency can be produced.

──────────────────────────────────────────────────の Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat ゛ (Reference) A61K 7/00 A61K 7/00 R 7/027 7/027 7/32 7/32 F-term (Reference) 4C083 AA082 AA122 AB212 AB222 AC012 AC072 AC302 AC352 AC372 AC392 AC442 AC482 AC642 AC661 AC662 AC842 AD112 AD172 AD492 AD512 AD572 AD662 BB13 CC13 CC17 DD11 DD41 EE01 4H006 AA01 AA03 AB12 AC53 BV22

Claims (11)

[Claims] 1. The following general formula (I): (Wherein, R ¹ and R ² each independently have 1 to 2 carbon atoms)
6 represents a hydrocarbon group, R ³ represents a hydrocarbon group having 7 to 10 carbon atoms, n represents 1 or 2, and the acidic amino acid residue in the molecule is L-asparagine when n is 1. An acid residue, and when n is 2, L-glutamic acid residue). 2. R ¹ and R ² are each independently a linear or branched alkyl group having 1 to 26 carbon atoms, and R ³ is a linear or branched alkyl group having 7 to 10 carbon atoms. The compound according to claim 1, which is an alkyl group and n is 2. 3. The compound according to claim 1, which is N-2-ethylhexanoyl-L-glutamic acid dibutylamide, N-octanoyl-L-glutamic acid dibutylamide, or N-decanoyl-L-glutamic acid dibutylamide. 4. The compound according to claim 1, which is N-2-ethylhexanoyl-L-glutamic acid dibutylamide. 5. An oil-based gelling agent containing at least one of the compounds according to claim 1. Description: 6. An oil-based gelling agent comprising at least one compound according to any one of claims 1 to 4 and N-lauroyl-L-glutamic acid dibutylamide. 7. The ratio of the total weight of the compound according to any one of claims 1 to 4 to the weight of N-lauroyl-L-glutamic acid dibutylamide is 35: 5 to 5:35. The gelling agent according to item 1. 8. A gel composition comprising (a) the gelling agent according to any one of claims 5 to 7, and (b) at least one oily base. 9. The gel composition according to claim 8, which is a translucent composition. 10. The gel composition according to claim 8, further comprising (c) at least one antiperspirant active ingredient. 11. A cosmetic comprising the gel composition according to any one of claims 8 to 10.