JPH11106315A - Cosmetic composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a cosmetic composition which shows excellent hair- conditioning effect, gives excellent moistness but no tenseness to the skin by using a specific basic amino acid derivative and an anionic surfactant. SOLUTION: This cosmetic contains (A) one or more kinds of basic amino acid derivative represented by formula I [R<1> is a 8-22C alkyl or alkenyl; j is 0 or 1; X is H or a substituent of formula II (R<2> is same as R<1> ; n is 0 or 1); k is 0-5 and, when k is 0, Y is a substituent represented by the formula: -(CH2 )m -Z (m is 1-5; Z is -NH2 or the like); when k is 1, Y is an amino group] and salts thereof, and (B) at least one selected from anionic surfactants. The compound of formula I is prepared by reaction of a basic amino acid with a glycidyl ether or an epoxy alkane.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a cosmetic composition, more specifically, one or more selected from specific derivatives of basic amino acids and salts thereof (component (A)) and one or more anionic surfactants (component (A)). Component (B)) as an active ingredient.

[0002]

2. Description of the Related Art In cosmetic compositions such as shampoos and rinse-in shampoos, anionic surfactants are widely used to provide detergency. Later, the smoothness of the hair is lost, the hair becomes stiff and hard, and problems such as poor combing and easy generation of split hairs and split ends may occur.

In order to solve such inconveniences, components having a conditioning action are often blended into cosmetic compositions.

[0004] Alkyl quaternary ammonium salts such as alkyltrimethylammonium chloride are most commonly used in hair cosmetic compositions for the purpose of imparting a conditioning effect.

[0005] However, when an alkyl quaternary ammonium salt is used in combination with an anionic surfactant, a salt insoluble in water is formed, so that the solubility and feeling in use are reduced. For this reason,
There are problems that it is necessary to add other components for dispersing and dissolving the insoluble salt and that the amount of the salt is limited.

Further, an alkyl quaternary ammonium salt is
It is also a problem that it is highly irritating to the skin and the mucous membrane of the eye and has poor biodegradability. Therefore, development of a conditioning agent that replaces the alkyl quaternary ammonium salt is required.

[0007] As conditioning agents other than the alkyl quaternary ammonium salts, alkylamidoamine salts such as diethylaminoethylamide stearate and cocoylarginine ethyl ester / pyrrolidonecarboxylate are known. However, although these components are superior in terms of hypoallergenicity and biodegradability as compared with the alkyl quaternary ammonium salts, they did not exert a conditioning effect.

[0008] O- [2-hydroxy-3-chloride is used as a conditioning component of the cosmetic composition for hair.
A cationized cellulose such as (trimethylammonio) propyl] hydroxyethylcellulose is often used.

However, since cationized cellulose forms a film between the hairs, there is a problem in that if the cationized cellulose is added in a large amount in order to sufficiently exert the conditioning effect, the hair will feel stiff.

[0010] Acrylamide-based cationized polymers such as dimethyldiallylammonium chloride-acrylamide copolymer are also commonly used, but the conditioning effect is inferior to that of cationized cellulose. There is a problem that finger passing during washing and rinsing is poor.

[0011] Anionic surfactants are also commonly used in skin cosmetics, but there is a problem that the skin feels tight.

[0012]

SUMMARY OF THE INVENTION An object of the present invention is to provide a cosmetic composition which has an excellent conditioning effect on the hair, and which has an excellent non-tactile and moist feeling on the skin.

[0013]

Means for Solving the Problems The present inventors have conducted intensive studies in view of the above situation, and as a result, reacted an anionic surfactant with glycidyl ether, an epoxy compound, and a basic amino acid such as arginine or lysine. It has been found that the above object can be achieved by using the obtained basic amino acid derivative in combination, and the present invention has been completed based on such findings.

That is, the present invention relates to a basic amino acid derivative represented by the following general formula (1) and a salt thereof.
The present invention relates to a cosmetic composition comprising, as active ingredients, at least one kind (A) and at least one kind (B) selected from anionic surfactants.

[0015]

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[In the general formula (1), R ¹ represents a linear or branched alkyl or alkenyl group having 8 to 22 carbon atoms, and X represents a hydrogen atom or a general formula (2) below. And k represents an integer of 0 to 5, and k =
When 0, Y represents a substituent represented by the following general formula (3), and when k = 1 to 5, Y represents an amino group. ]

[0017]

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[In the above formula (2), R ² is the same or different from R ¹ and represents a linear or branched alkyl or alkenyl group having 8 to 22 carbon atoms. ]

[0019]

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[In the general formula (3), m represents an integer of 1 to 5, and Z represents any of the following substituents (I) to (IV). ]

[0021]

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[0022]

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

The basic amino acid derivative represented by the general formula (1), which is the first essential component (A) of the cosmetic composition of the present invention, is represented by a basic amino acid and the following general formula (4) Can be easily produced by reacting the glycidyl ether with a glycidyl ether under an alkaline condition in an organic solvent such as a lower alcohol or a polyhydric alcohol, or a mixed solvent of these organic solvents and water.

[0024]

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[In the above formula, R ³ represents a linear or branched alkyl or alkenyl group having 8 to 22 carbon atoms. ]

The glycidyl ether represented by the general formula (4) can be obtained, for example, by reacting a saturated or unsaturated higher natural or synthetic alcohol with epichlorohydrin. Specific examples thereof include decyl glycidyl ether, dodecyl glycidyl ether,
Examples thereof include tetradecyl glycidyl ether and stearyl glycidyl ether, each of which may be a single composition or a mixture of two or more of them at an arbitrary ratio. Industrially available glycidyl ethers include NOF Corporation
"Epiol L-41" (decyl glycidyl ether), "Epiol SK" (stearyl diglycyl ether), and "Heroxy 8" (dodecyl glycidyl ether and tetradecyl glycidyl ether of AC I Japan Limited) Mixture), "Denacol EX-192" (a mixture of dodecyl glycidyl ether and tetradecyl glycidyl ether) manufactured by Nagase Kasei Kogyo Co., Ltd., and "SY-25L" manufactured by Sakamoto Pharmaceutical Co., Ltd.
(A mixture of decyl glycidyl ether and dodecyl glycidyl ether).

As the basic amino acid, any of natural and synthetic amino acids can be used. For example, arginine, lysine, ornithine, histidine, hydroxylysine, α,
Among them, γ-diaminobutyric acid and the like are preferable, and arginine and lysine are preferable, and arginine is particularly preferable. Further, any of D-form, L-form and DL-form can be used.

The amino acid derivative obtained by reacting an acidic or neutral amino acid with glycidyl ether does not have the conditioning effect as in the present invention.

Among the basic amino acids, for example, in the case of lysine and ornithine, the binding sites for glycidyl ether are considered to be preferentially ε-amino and δ-amino, respectively. It may be a reacted one. Further, ε-amino group, δ-amino group or α
-Two molecules of glycidyl ether may react with any of the amino groups. In addition, each of ε-amino group (δ-amino group in ornithine) and α-amino group
It may be a compound obtained by reacting each molecule (two molecules in total) or a compound in which three or four glycidyl ethers are added to one basic amino acid molecule. For example, the following eight kinds of compounds (5) to (12) are exemplified as the basic amino acid derivative of the present invention generated in the reaction between glycidyl ether and lysine.

[0030]

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[0031]

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[0032]

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[0033]

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[0034]

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[0035]

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[0036]

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[0037]

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[In the above formulas (5) to (12), R ³ has the same meaning as described above. However, as described later, (7) to (1)
In the compound of 2), a plurality of R ³ in the same molecule may be different chains, or may be the same chain. ]

However, particularly preferred are compounds in which one molecule of glycidyl ether is added to one molecule of a basic amino acid.

In the reaction between glycidyl ether and an amino acid, it is preferable to use the amino acid as an alkali metal salt or to react it under alkaline conditions in order to increase the reactivity and prevent side reactions. However, arginine may be reacted without using these conditions.

As the reaction solvent, one or more organic solvents such as lower alcohols or polyhydric alcohols are usually used. Examples of lower alcohols are methyl alcohol, ethyl alcohol, n-propyl alcohol,
Isopropyl alcohol, n-butyl alcohol, and the like. Examples of the polyhydric alcohol include glycerin, 1,
Examples thereof include 3-butylene glycol, propylene glycol, dipropylene glycol, and isoprene glycol. These organic solvents may be used in a single composition or in a mixture of two or more kinds at an arbitrary ratio. Of course, a mixture of different kinds of organic solvents such as a higher alcohol and a polyhydric alcohol may be used. Also, to increase the solubility of basic amino acids,
It is more preferable to use these organic solvents and water in combination.
The mixing ratio between the organic solvent and water varies depending on the type of amino acid and the type of glycidyl ether, but usually, organic solvent: water = 100: 0 to 10:90, preferably 1: 1 to 1: 1.
The range is 9: 1. When the proportion of the organic solvent is low, the solubility of glycidyl ether is low, and the reaction rate is significantly reduced.

The reaction temperature varies depending on the type and composition of the reaction solvent. For example, in the case of isopropyl alcohol, it is usually in the range of 70 to 100 ° C., preferably 80 to 95 ° C., and in the case of ethyl alcohol, it is usually 60 to 78 ° C. C, preferably in the range of 70 to 78C, and it is preferable to carry out the reaction under reflux. The method of adding glycidyl ether may be batch addition before heating or divided addition or continuous addition (continuous dropping) after heating is started. However, in order to suppress generation of by-products, continuous addition is performed after heating is started. It is preferable to drop it.

The product obtained by the reaction between glycidyl ether and a basic amino acid is not usually a single compound, but a mixture of one basic amino acid molecule and one or more glycidyl ether molecules. Becomes These mixtures may be isolated and purified into single compounds by, for example, chromatography, and then one or more of them may be used as a raw material of the cosmetic composition of the present invention,
The mixture may be used as it is. Furthermore, unreacted basic amino acids may be present in the mixture.

In the basic amino acid derivative of the present invention in which a plurality of glycidyl ethers are added to one basic amino acid molecule, the chain lengths of the plurality of added glycidyl ethers may be the same or different. When the reaction was performed using a mixture of glycidyl ethers having different chain lengths,
The resulting composition is usually a mixture of those having the same chain length and those having a different chain length. For example, "Heroxy 8" manufactured by AC I Japan Limited
When a reaction is carried out using (mixture of dodecyl glycidyl ether and tetradecyl glycidyl ether) and arginine, the resulting basic amino acid derivatives of the present invention are the following five compounds (13) to (17). These may be isolated and purified for each single compound as described above, or may be used as a mixture.

[0045]

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[0046]

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[0047]

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[0048]

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[0049]

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The reaction mixture obtained by reacting the glycidyl ether with a basic amino acid may be used without any purification treatment if it is acceptable, or may be purified to such an extent that the reaction solvent is distilled off if necessary. Can be used as a raw material of the cosmetic composition of the present invention. For example, when ethyl alcohol, 1,3-butylene glycol, propylene glycol, etc., which are often used in cosmetics and the like, are used as the reaction solvent, these are contained in the reaction mixture within a range that does not impair the effects of the present invention. You may.

As the salt of the basic amino acid derivative represented by the general formula (1), for example, hydrochloride, hydrobromide,
Inorganic acid salts such as sulfate, phosphate, nitrate, carbonate, etc., acetate, citrate, lactate, glycolate, malate, p-toluenesulfonate, tartrate, glutamate and derivatives thereof , Aspartate and its derivatives, organic acid salts such as pyrrolidone carboxylate, and the like. These can use any optical isomer. Particularly preferred salts include hydrochloride, hydrobromide, pyrrolidone carboxylate, citrate, lactate, glycolate, glutamate, aspartate and the like.

Next, the anionic surfactant which is the second essential component (B) of the cosmetic composition of the present invention will be described.

Examples of the anionic surfactant include, for example,
Carboxylate type, sulfonate type, sulfate ester type,
Anionic surfactants such as higher fatty acid salt type are exemplified.

Examples of the carboxylate type anionic surfactant include N-acylaminocarboxylic acid type and ether carboxylic acid type surfactants.

In the N-acylaminocarboxylate type anionic surfactant, the acyl group has 8 carbon atoms.
And 22 acyl residues of saturated or unsaturated fatty acids, for example, acyl residues of fatty acids having a single composition such as lauric acid, myristic acid, palmitic acid, stearic acid, and oleic acid. Oil fatty acids, tallow fatty acids,
Hardened tallow fatty acid, castor oil fatty acid, olive oil fatty acid,
The acyl residue may be a mixed fatty acid obtained from nature such as palm oil fatty acid or a fatty acid (including branched fatty acid) obtained by synthesis. And the aminocarboxylic acid binding thereto is, for example, glutamic acid, aspartic acid, cysteic acid, acidic amino acids such as homocysteic acid, glycine, alanine, valine, leucine, isoleucine, phenylalanine, tryptophan, sarcosine, β-alanine, γ -Aminobutyric acid, ε-aminocaproic acid, serine, homoserine, tyrosine, proline,
Neutral amino acids such as hydroxyproline, cystine, cysteine and methionine; and basic amino acids such as lysine, ornithine and arginine. These acylaminocarboxylic acids can be used both in the optically active form and in the racemic form.

Examples of the ether carboxylate type anionic surfactant include polyoxyethylene alkyl ether acetate, polyglyceryl alkyl ether acetate, and the like. Specifically, for example, polyoxyethylene lauryl ether acetate, And polyoxyethylene tridecyl ether acetate.

Examples of the sulfonate-type anionic surfactant include a sulfosuccinate-type anionic surfactant, an alkyl sulfonate-type, an ester sulfonate-type, and an N-acyl sulfonate-type monobasic. An acid type organic sulfonate type anionic surfactant is exemplified.

The sulfosuccinate type anionic surfactant is a sulfosuccinate of a higher alcohol or an ethoxylate thereof or a sulfosuccinate derived from a higher fatty acid amide represented by the following general formula (18) or (19). Alternatively, these salts may be mentioned.

[0059]

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[Wherein R ⁴ is R ⁵ —O— or R ⁶ —
CONH- are shown (wherein, R ⁵ is 8-22 carbon atoms
A linear or branched alkyl or alkenyl group, and R ⁶ represents a linear or branched alkyl or alkenyl group having 7 to 21 carbon atoms), M ¹ and M ² each independently represent hydrogen Represents an atom or a cation selected from alkali metals, alkaline earth metals, ammonium and organic ammonium, and a represents an integer of 0 to 20. ]

More specifically, for example, undecylenoylamidoethylsulfosuccinate, polyoxyethylene lauroylethanolamide sulfosuccinate, lauryl sulfosuccinate, lauryl polyoxyethylene sulfosuccinate, amide oleosulfosuccinate, etc. Is mentioned.

The monobasic acid-type organic sulfonate-type anionic surfactants include those having 8 to 8 carbon atoms.
22 linear or branched alkyl or alkenyl sulfonates, an alkylbenzene sulfonate having a linear or branched alkyl group having 10 to 16 carbon atoms,
And N-acyl sulfonates or O-acyl sulfonates in which the acyl group is a linear or branched saturated or unsaturated fatty acid residue having 8 to 22 carbon atoms.

Specific examples include alkanesulfonic acid salts, α-olefinsulfonic acid salts, alkylbenzenesulfonic acid salts, acylmethyltaurine salts, isethionic acid fatty acid ester salts, and α-sulfonated fatty acid ester salts.

Examples of the sulfate type anionic surfactant include surfactants such as alkyl sulfate and ether sulfate.

The alkyl sulfate type anionic surfactant is a salt of an ester of sulfuric acid with a straight or branched chain saturated or unsaturated higher alcohol having 8 to 22 carbon atoms, for example, lauryl sulfate , Myristyl sulfate, oleyl sulfate and the like.

The above-mentioned ether sulfate type anionic surfactant is an alkylene oxide addition type of the above-mentioned alkyl sulfate, for example, polyoxyethylene lauryl ether sulfate, polyoxyethylene myristyl ether sulfate, polyoxyethylene oleate. Oil ether sulfate and the like.

Examples of higher fatty acid salt type anionic surfactants include coconut oil fatty acid salt, palm kernel oil fatty acid salt, palm fatty acid salt, laurate, myristate, palmitate, stearate, behenate, and olein. Acid salts and the like.

The base components of these various anionic surfactants include alkali metals such as sodium and potassium, alkaline earth metals such as magnesium and calcium, monoethanolamine, diethanolamine, triethanolamine and 2-amino-2. Organic amines such as -methyl-1-propanol and 2-amino-2-methyl-1,3-propanediol; basic amino acids such as lysine, ornithine and arginine; and ammonia. These base components can be used alone or in combination of two or more.

These anionic surfactants may be used alone or in combination of two or more.

The amount of the component (B) in the cosmetic composition of the present invention can be appropriately determined according to the intended product.
It is usually 0.1 to 99% by weight, preferably 1 to 95% by weight, more preferably 5 to 90% by weight. If the amount is less than 0.1% by weight, the provided cleaning effect may not be sufficient.

The cosmetic composition of the present invention comprises a shampoo, a rinse, a rinse-in shampoo, a conditioning shampoo, a hair lotion, a hair conditioner, a hair treatment, a hair cream, a hair spray, a hair liquid, a hair wax, a hair water, a hair styling gel, Various hair cosmetics such as perm solution, hair color, hair manicure, and lotion, emulsion, face wash, makeup remover, cleansing lotion, emollient lotion, nourishing cream, emollient cream, massage cream, cleansing cream, body shampoo, hand Soap, shaving cream,
Tanning cosmetics, deodorant powder, deodorant lotion, deodorant spray, makeup remover gel, moisture gel, moisturizing essence, UV protection essence, shaving foam, white powder, foundation, lipstick, blusher, eyeliner, eye shadow, eyebrows, bath powder, etc. It can be used as various skin cosmetics.

In the cosmetic composition of the present invention, other surfactants can be used in combination as long as the effects of the present invention are not impaired.

Examples of the amphoteric surfactant include a carbobetaine-type amphoteric surfactant, an amidobetaine-type amphoteric surfactant,
Sulfobetaine-type amphoteric surfactants, hydroxysulfobetaine-type amphoteric surfactants, amide sulfobetaine-type amphoteric surfactants, phosphobetaine-type amphoteric surfactants, amphoteric surfactants such as imidazoline-type amphoteric surfactants, and the like, More specifically, for example, lauryl dimethyl amino acetate betaine, coconut oil alkyl betaine, stearyl dimethylamino acetate betaine, stearyl dihydroxyethyl betaine, lauric amide propyl betaine, coconut oil fatty acid amide propyl betaine solution, palm kernel oil fatty acid amide propyl Betaine solution, amide ricinoleate betaine solution, N-coconut fatty acid acyl-N-carboxyethyl-N-hydroxyethylethylenediamine sodium, palm kernel oil fatty acid acyl-N-carboxyethyl-N-hydro Phenoxyethyl sodium ethylenediamine, 2-alkyl -N- carboxymethyl -N- hydroxyethyl imidazolium betaine, undecyl -N
Carboxymethylimidarinium betaine, alkyldiaminoethylglycine hydrochloride solution, bis (stearyl-N
-Hydroxyethylimidazoline) chloroacetic acid complex.

Examples of nonionic surfactants include polyoxyethylene lauryl ether, polyoxyethylene myristyl ether, polyoxyethylene cetyl ether, polyoxyethylene isocetyl ether, polyoxyethylene setosteryl ether, and polyoxyethylene isostearyl ether. , Polyoxyethylene oleyl cetyl ether, polyoxyethylene oleyl ether, polyoxyethylene behenyl ether, polyoxyethylene tridecyl ether, polyoxyethylene octyl dodecyl ether, polyoxyethylene butyl ether, polyoxyethylene alkyl (12-14) ether, Polyoxyethylene octyl phenyl ether,
Polyoxyethylene dinonyl phenyl ether, polyoxyethylene nonyl phenyl ether, polyoxyethylene cholesteryl ether, polyoxyethylene cholestanol ether, polyoxyethylene phytosterol, polyoxyethylene lanolin alcohol, acetate polyoxyethylene lanolin alcohol, polyoxyethylene lanolin , Polyoxyethylene liquid lanolin, polyoxyethylene reduced lanolin, polyoxyethylene polyoxypropylene liquid lanolin, polyethylene glycol octanoate / polyoxyethylene nonylphenyl ether mixture, polyoxyethylene hydrogenated castor oil, polyoxyethylene castor oil, monostearin Acid polyoxyethylene hydrogenated castor oil, polyoxypropylene glyceryl ether, polyoxy Propylene glyceryl ether, polyoxypropylene diglycer ether, polyoxypropylene sorbitol, polyoxypropylene cetyl ether, polyoxypropylene stearyl ether, polyoxypropylene lanolin alcohol ether, polyoxypropylene hard lanolin, polyoxyethylene polyoxypropylene lanolin, poly Oxyethylene polyoxypropylene glyceryl ether, polyoxyethylene polyoxypropylene lauryl ether, polyoxyethylene polyoxypropylene cetyl ether, polyoxyethylene polyoxypropylene stearyl ether, ethylenediamine tetrapolyoxyethylene propylene, sorbitan monolaurate, sorbitan monopalmitate Sorbitan monostearate Sorbitan monoisostearate, sorbitan monooleate, sorbitan coconut fatty acid, sorbitan sesquiisostearin, sorbitan sesquioleate, sorbitan distearate, sorbitan sesquistearate, sorbitan tristearate, sorbitan trioleate, polyoxyethylene sorbitan monolaurate , Polyoxyethylene sorbitan monopalmitate, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan monooleate, polyoxyethylene sorbitan tristearate, polyoxyethylene sorbitan trioleate, polyoxyethylene sorbitan tetraoleate, alkyl (8-16) glucoside, methyl glucosides sesquistearate, polyoxyethylene oleic acid Methyl glucoside, polyoxyethylene methyl glucoside sesquistearate, polyoxyethylene methyl glucoside distearate, polyoxypropylene methyl glucoside, polyoxyethylene glucoside distearate, ethylene glycol monostearate, ethylene glycol distearate, ethylene glycol dilaurate, laurin Propylene glycol, self-emulsifying propylene glycol stearate, propylene glycol isostearate, propylene glycol oleate, propylene glycol ricinoleate, propylene glycol di (caprylate / caprate), propylene glycol distearate, propylene glycol diisostearate, propylene dioleate Glycol,
Polyethylene glycol monolaurate, polyethylene glycol monopalmitate, polyethylene glycol monostearate, polyethylene glycol monoisostearate, polyethylene glycol monooleate, polyethylene glycol dilaurate, polyethylene glycol distearate, polyethylene glycol diisostearate, polyethylene glycol dioleate , Lanolin fatty acid polyethylene glycol, glyceryl laurate, glyceryl myristate, glyceryl palmitate, lipophilic monostearyl glycerin, self-emulsifying monostearyl glycerin,
Glyceryl isostearate, glyceryl oxystearate, glyceryl oleate, lipophilic glyceryl oleate, glyceryl ricinoleate, glyceryl behenate, glyceryl erucate, glyceryl coconut fatty acid, glyceryl sesquioleate, glyceryl diisostearate, triisopalmitate Glyceryl, hydrogenated soybean oil fatty acid glyceryl, glyceryl trilaurate, glyceryl monostearate, glyceryl ricinoleate acetate, polyglyceryl monostearate, polyglyceryl monooleate, polyglyceryl distearate, polyglyceryl diisostearate, polyglyceryl dioleate, polyglyceryl condensed ricinoleate ,
Polyoxyethylene glyceryl laurate, polyoxyethylene glyceryl monostearate, polyoxyethylene glyceryl oleate, polyoxyethylene glyceryl coconut oil fatty acid, polyoxyethylene glyceryl trioleate, polyoxyethylene laurate hydrogenated castor oil, poly myristate Oxyethylene myristyl ether, polyoxyethylene cetyl stearate,
Polyoxyethylene stearyl ether stearate,
Polyoxyethylene hydrogenated castor oil isostearate, polyoxyethylene hydrogenated castor oil triisostearate,
Polyoxyethylene tallow alkyl hydroxymillistyrene ether, polyoxyethylene alkyl (12-1
5) Propyl ether acetate, polyoxyethylene alkyl (12 to 15) hexadecyl ether acetate, polyoxyethylene trimethylolpropane tristearate, polyoxyethylene trimethylolpropane tristearate, polyoxyethylene polyoxypropylene trimethylolpropane, diglycerin Oleyl ether, glyceryl isostearate, batyl alcohol, palmitic acid amide, stearic acid amide, polyoxyethylene ricinoleic acid amide, lauric acid ethanolamide, palmitic acid ethanolamide, stearic acid ethanolamide, coconut oil fatty acid ethanolamide, polyoxyethylene Lauric acid monoethanolamide, polyoxyethylene coconut oil fatty acid monoethanolamide, lauric acid die Nolamide, lauric acid myristic acid diethanolamide, myristic acid diethanolamide, stearic acid diethanolamide, oleic acid diethanolamide, isostearic acid diethanolamide, linoleic acid diethanolamide, coconut oil fatty acid diethanolamide, palm kernel oil diethanolamide, hardened tallow oil Diethanolamide, polyoxyethylene coconut oil fatty acid diethanolamide, isopropanolamide laurate, isopropanolamide oleate, stearoylethanolamide stearate, lauryl dimethylamine oxide solution, lauryl dimethylamine oxide solution, myristyl dimethylamine oxide solution,
Stearyl dimethylamine oxide, coconut oil alkyldimethylamine oxide solution, polyoxyethylene coconut oil alkyldimethylamine oxide, dihydroxyethyllaurylamine oxide solution, dioctyldodecyl lauroylglutamate, dioctyldodecyl stearoylglutamate, polyoxyethyleneoctyldodecylether diester lauroylglutamate, Examples thereof include lauroylglutamic acid dipolyoxyethylene stearyl ether, polyoxyethylene hydrogenated castor oil pyroglutamic acid isostearic acid diester, and polyoxyethylene glyceryl pyroglutamic acid isostearic acid diester.

In addition to the above-mentioned surfactants, various commonly used additives can be added as long as the effects of the present invention are not impaired. Examples are silicone compounds,
Polymeric substances, fatty acids, alcohols, polyhydric alcohols,
Extracts, amino acids, nucleic acids, vitamins, enzymes, anti-inflammatory drugs,
Disinfectants, preservatives, antioxidants, ultraviolet absorbers, chelating agents, antiperspirants, pigments, dyes, oxidation dyes, organic and inorganic powders, pH adjusters, pearling agents, wetting agents and cosmetic raw material standards, cosmetics Classified ingredients, quasi-drug raw material standards,
Raw materials and the like described in the Japanese Pharmacopoeia and the compendium of food additives.

Examples of silicone compounds 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 and dodecamethylcyclohexasiloxane;
Methylphenyl polysiloxane, trimethylsiloxysilicic acid; amino-modified silicone such as aminoethylaminopropylsiloxane-dimethylsiloxane copolymer, silanol-modified polysiloxane, alkoxy-modified polysiloxane, fatty acid-modified polysiloxane, fluorine-modified polysiloxane, epoxy-modified poly Examples include siloxane, alkoxy-modified polysiloxane perfluoropolyether, polyvinyl acetate dimethylpolysiloxane, and a silicone emulsion obtained by emulsifying one or more of these.

Examples of high molecular substances include plant polysaccharide polymers such as guar gum, locust bingham, quince seed, carrageenan, galactan, arabic gum, tragacanth gum, pectin, mannan, starch and pullulan; xanthan gum, dextran, succino Polysaccharides derived from microorganisms such as glucan, curdlan, hyaluronic acid; animal proteins such as gelatin, casein, albumin, collagen; methylcellulose, ethylcellulose, hydroxyethylcellulose, hydroxypropylcellulose, carboxymethylcellulose and salts thereof, methyl Cellulose derivatives such as hydroxypropylcellulose; Starch derivatives such as soluble starch, carboxyl starch and methyl starch; Propylene glycol alginate Alginic acid derivatives such as alginates, polyvinyl alcohol, polyvinyl butyral,
Vinyl acetate / vinyl pyrrolidone copolymer, vinyl acetate
Crotonic acid copolymer, vinyl methyl ether / ethyl maleate copolymer, vinyl methyl ether / butyl maleate copolymer, crotonic acid / vinyl acetate / vinyl neodecanoate copolymer, methoxyethylene maleic anhydride copolymer, Isobutylene / sodium maleate copolymer, N-methylpyrrolidone, vinylpyrrolidone / N, N
-Dimethylaminoethyl methacrylic acid copolymer diethyl sulfate, vinyl imidazolium metochloride / vinyl pyrrolidone copolymer, polyvinyl pyrrolidone, vinyl pyrrolidone / styrene copolymer, vinyl pyrrolidone / hexadecene copolymer, styrene / vinyl pyrrolidone copolymer Copolymers, vinyl derivatives such as eicosene-vinylpyrrolidone copolymer, carboxyvinyl polymer; alkyl acrylate copolymer, polyacrylic acid and salts thereof (sodium, potassium, ammonium, triethanolamine,
Arginine, lysine, etc.), polyalkyl acrylate, alkyl acrylate copolymer, acrylamide / styrene copolymer, alkyl acrylate / styrene copolymer,
Acrylic acid octylamide / acrylic acid ester copolymers and salts thereof, octylamide acrylate / hydroxypropyl acrylate / butylaminoethyl methacrylate copolymer, acrylic resin alkanolamine, hydroxyethyl acrylate / methoxyethyl acrylate Copolymers, acrylic acid derivatives such as alkyl acrylate / alkyl methacrylate / diacetone / acetone acrylamide / methacrylic acid copolymer, dimethyldiallylammonium chloride / acrylamide copolymer;
Methacryloylethyldimethyldimethylbetaine / methacryloylethyltrimethylammonium chloride / methoxypolyethylene glycol methacrylate copolymer, methacryloylethyldimethylbetaine / methacryloylethyltrimethylammonium chloride / 2-hydroxyethyl methacrylate copolymer, carboxymethyldextran and salts thereof; chloride Cationized cellulose such as 0- [2-hydroxy-3- (trimethylammonio) propyl] hydroxyethylcellulose, hydroxyethylcellulose hydroxypropyllauryldimethylammonium chloride; O- [2-hydroxy-3- (trimethylammonio) propyl chloride Cationized guar gum such as guar gum, epoxy resin isostearate, polyamide Chlorohydrin resin, bisphenol epoxy resin fatty acid esters, polyethylene glycol-epichlorohydrin-coconut oil alkylamine-dipropylenetriamine condensate, perfluoro polyether and the like.

Examples of other components include beeswax, beeswax, candelilla wax, carnauba wax, ibis taro, mokuro, rice bran wax, sara simon tarou,
Lanolin, ceresin, squalane, pristane, turpentine oil, eucalyptus oil, terpineol, eucalyptol, olive oil, camellia oil, teaseed oil, sasanqua oil, safflower oil, sunflower oil, soybean oil, cottonseed oil, sesame oil, corn oil, peanut Oil, rapeseed oil, rice bran oil,
Rice germ oil, barley oil, grape seed nut oil, meadowfoam oil, shea butter, evening primrose oil, cacao butter, castor oil, hardened child oil, almond oil, jojoba oil, avocado oil,
Carrot oil, macadamia nut oil, boiled castor oil, linseed oil, coconut oil, palm oil, palm kernel oil, tallow, horse oil, mink oil, cod liver oil, shark liver oil, orange roughy oil, milk fat, egg yolk oil, egg yolk fatty oil, powder Fatty oil, clove oil, rosehip oil, lavender oil, Roman chamomile oil, rosemary oil, partially hydrolyzed jojoba oil, oxystearic acid castor oil, castor oil, partially hydrogenated horse oil, adsorptive purified lanolin, liquid lanolin Lanolin, reduced lanolin, hard lanolin acetate, hard lanolin acetate, liquid lanolin acetate, liquid paraffin, light paraffin, heavy paraffin, volatile paraffin, liquefied petroleum gas, petrolatum, microcrystalline wax, acetic acid (cetyl lanolyl) ester, triacetyl glyceryl, propion Eicosanyl acid, lauryl lactate, lactate Still, cetyl lactate, octyldodecyl lactate, diisostearyl malate, succinic acid polypropylene glycol oligoester, succinic acid 2-ethylhexyl, stearyl heptanoate, diisopropyl adipate, dibutyl adipate, dioctyl adipate,
Di-2-ethylhexyl adipate, di-2 heptylundecyl adipate, cetyl caprylate, cetyl 2-ethylhexanoate, cetostearyl 2-ethylhexanoate, tetra-2
Pentaerythritol ethylhexanoate, isocetyl octanoate, isostearyl octanoate, ethylene glycol dioctanoate, neopentyl glycol dioctanoate, trimethylolpropane trioctanoate, hexyldecyl dimethyloctanoate, octyldodecyl dimethyloctanoate, isononyl isononanoate, Isodecyl isononanoate, isotridecyl isononanoate, isotridecyl dinonanoate, propylene glycol dinonanoate, octyl pelargonate, octyl isoperargonate, glycerin tri (capryl / caproate), neopentyl glycol dicaprate, 2-ethylhexyl hydroxystearate, ethyl oleate , Decyl oleate, isodecyl oleate, oleyl oleate, oleyl decyl oleate, (Oleic acid) Ethylene glycol, tri (oleic acid) glyceryl, octyldodecyl ricinoleate, isodecyl pivalate, isostearyl pivalate, glyceryl tribehenate, octyldodecyl erucate, isopropyl lanolin fatty acid, octyldodecyl lanolin fatty acid, ethyl avocado oil fatty acid Oils and fats such as ethyl mink oil fatty acid, dipentaerythritol fatty acid ester and dipentaerythritol hexaoxystearate; esters such as isopropyl myristate and octyldodecyl myristate; talc, kaolin, mica, sericite, muscovite, Phlogopite, synthetic mica, phlogopite,
Lithium mica, vermiculite, magnesium carbonate, calcium carbonate, aluminum silicate, barium silicate,
Calcium silicate, magnesium silicate, strontium silicate, metal tungstate, magnesium, silica, zeolite, barium sulfate, calcined calcium sulfate,
Calcium phosphate, calcium phosphate, hydrofluoric apatite, hydroxyapatite, ceramic powder, zinc myristate, calcium palmitate, aluminum stearate, boron nitride, titanium dioxide, zinc oxide,
Bengala, iron titanate, γ-iron oxide, yellow iron oxide, black iron oxide, carbon black, mango violet, baltic violet, chromium oxide, chromium hydroxide, cobalt titanate, ultramarine, navy blue, titanium oxide coated mica, titanium oxide Coated mica, titanium oxide coated bismuth oxychloride, bismuth oxychloride, aluminum powder, copper powder,
Red 201, Red 202, Red 204, Red 20
No. 5, Red No. 220, Red No. 226, Red No. 228, Red No. 405, Orange No. 203, Orange No. 204, Yellow No. 205
No., Yellow No. 401, Blue No. 404, Red No. 3, Red No. 10
No. 4, Red No. 106, Red No. 227, Red No. 230, Red No. 401, Red No. 505, Orange No. 205, Yellow No. 4,
Powders such as Yellow No. 5, Yellow No. 202, Yellow No. 203, Green No. 3, Blue No. 1, chlorophyll, β-carotene, etc .; Arbutin, Kojic acid, Vitamin C and derivatives thereof as a whitening agent; Assembly extract as a vasodilator Cepharanthin, vitamin E and its derivatives, hydroquinone and its derivatives; γ-oryzanol; pepper tincture, ginger tincture, nicotinic acid benzyl ester as a local stimulant; vitamins A, B1, B2, B as nutrients
6, E and its derivatives; cystine, cysteine, acetylcysteine, methionine, serine, leucine, tryptophan, glycine, arginine, aspartic acid, glutamic acid, isoleucine, alanine, histidine, lysine, proline, oxyproline, phenylalanine,
Threonine, tyrosine, valine, etc. amino acids and derivatives thereof; amino acid extracts and derivatives thereof; estradiol and ethinylestradiol as female hormones; pantothenic acid and derivatives thereof as hair root activators;
Placenta extract, allantoin, photosensitizer 301, etc .; anti-inflammatory agents such as β-glycyrrhetinic acid, glycyrrhizic acid derivatives, allantoin, azulene, ε-aminocaproic acid, hydrocortisone, hinokitiol, etc .; tranexamic acid as an antiplasmin agent;
Zinc sulfate, allantoin hydroxyaluminum, aluminum chloride, aluminum sulfate, sulfonite zinc carbonate,
Tannic acid, citric acid, lactic acid and the like; natural products derived from hamamelis, odori grass, birch, rhubarb, etc .; menthol, camphor, a hormone as estradiol and its ester derivatives; estrone, ethinyl estradiol, cortisone and its ester derivatives as hormones Hydrocortisone and its ester derivatives, prednisone, prednisolone, etc .; diphenhydramine hydrochloride, chlorferamine maleate as antihistamines; sulfur, salicylic acid, resorcinol as exfoliating and dissolving agents; benzalkonium chloride, benzethonium chloride, halocarban as fungicides , 2,4,4-trichloro-2-hydroxyphenol, triclosan; natural products derived from chamomile extract and eucalyptus oil extract; promoting metabolism, promoting blood circulation, healing wounds, etc. , Ginseng extract, aloe,
Sicon, lily, luffa, marronnier, oak, safflower, etc .; as an ultraviolet absorber, benzophenone phenone derivative, paraaminobenzoic acid derivative, methoxycinnamic acid derivative, salicylic acid derivative, urocanic acid and its derivatives,
4-tert-butyl-4'-methoxydibenzoylmethane, 2- (2 '
-Hydroxy-5'-methylphenyl) benzotriazole, methyl anthranilate; naturally occurring substances such as maronier, β-carotene, etc .; humectants, pyrrolidonecarboxylic acid and its salts, hyaluronic acid and its salts, glycerin, 1,3-butylene Glycol, propylene glycol, dipropylene glycol, isoprene glycol,
Lactate, partially hydrolyzed chitin, trimethylglycine, sorbitol; hydrolyzed proteins such as collagen and hydrolyzed silk; polyamino acid salts such as polyaspartate and polyglutamate; blood-sucking insects (mosquitoes, lice, fleas) , Dimethyl phthalate, 2-ethyl-1,3-hexanediol, bisbutylenetetrahydrofurfural, N, N-diethyl-m-toluamide, etc .; paraben derivatives, benzoic acid derivatives, salicylic acid as preservatives Derivatives and the like.

[0079]

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 45.9 g (0.26 mol) of L-arginine, 29.2 g of water and 42.2 g of ethanol were added to a three-necked round bottom flask, and the mixture was heated and refluxed at 75 ° C. and dispersed. 73.6 g (0.29 mol) of "Heroxy 8" (manufactured by AC I Japan Limited) was added dropwise over 3 hours, and the mixture was further stirred for 3 hours. After confirming the disappearance of glycidyl ether by TLC and gas chromatography, the mixture was cooled to 40 ° C. or lower and cooled to 35 ° C.
% Hydrochloric acid (18.6 g, 0.18 mol) was added.
% Hydrochloric acid was added to adjust the pH to 5.2, and the solid content was about 60.
209 g of a 0% liquid composition were obtained.

Production Example 2: N- (2-hydroxy-3-dodecyloxy) propyl-L-arginine hydrochloride In a three-necked round bottom flask, 17.4 g (0.1 g) of L-arginine was added.
mol) was dissolved in 100 ml of water, and isopropanol 1
00 ml was added. 24.2 g of dodecyl glycidyl ether (manufactured by Sakamoto Yakuhin Kogyo Co., Ltd.) (0.
1 mol) is added dropwise over 30 minutes, and the mixture is directly refluxed.
Stir for 3 hours. After confirming the disappearance of dodecyl glycidyl ether by TLC and gas chromatography, the mixture was cooled to 40 ° C. or lower, and 10.1 g of 36% hydrochloric acid was added.
(0.1 mol) was added for neutralization.

The reaction mixture was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography (MERCK & Co., Inc. Kiese).
lgel 60, developing solvent chloroform / methanol / acetic acid =
3/1 / 0.5) and purified by N- (2-hydroxy-
15.0 g (yield: 36.0%) of 3-dodecyloxy) propyl-L-arginine hydrochloride was obtained.

TLC (butanol / acetic acid / water = 4/1 /
2): Rf = 0.64 ESI mass spectrum: 417.5 (MH ⁺ ) IR (NaCl, cm ⁻¹ ): 3177, 2955, 29
20, 2853, 1692, 1628, 1468, 13
97, 1377, 1215, 1116

Production Example 3 N, N-bis (2-hydroxy-3-dodecyloxy) propyl-L-arginine hydrochloride 17.4 g (0.1 g) of L-arginine was placed in a three-necked round bottom flask.
mol) was dissolved in 100 ml of water, and isopropanol 1
00 ml was added. Under heating and stirring under reflux, 48.4 g (0.2 mol) of dodecyl glycidyl ether was added dropwise over 30 minutes, and the mixture was stirred under reflux for 3 hours. After confirming the disappearance of dodecyl glycidyl ether by TLC and gas chromatography, the mixture was cooled to 40 ° C. or lower and neutralized by adding 10.1 g (0.1 mol) of 36% hydrochloric acid.

The reaction solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (Kieselgel 60, developing solvent: chloroform / methanol / acetic acid = 3/1 / 0.5) to give N, N-bis (2-hydroxy 1-1.4 g of -3-dodecyloxypropyl) -L-arginine hydrochloride
(17.2% yield).

TLC (butanol / acetic acid / water = 4/1 /
2): Rf = 0.72 ESI mass spectrum: 659.7 (MH ⁺ ) IR (NaCl, cm ⁻¹ ): 3177, 2955, 29
20, 2853, 1692, 1628, 1468, 13
97, 1377, 1215, 1120

Production Example 4: N- (2-hydroxy-3-octadecyloxy) propyl-L-arginine hydrochloride 17.4 g (0.1 mol) of L-arginine and octadecylglycidyl ether (manufactured by Sakamoto Yakuhin Kogyo Co., Ltd.) 3
By using 2.6 g (0.1 mol) and performing the same operation as in Production Example 2, 21.2 g of N- (2-hydroxy-3-octadecyloxy) propyl-L-arginine hydrochloride was obtained (yield: 42.3%). Was.

TLC (butanol / acetic acid / water = 4/1 /
2): Rf = 0.64 ESI mass spectrum: 501.5 (MH ⁺ ) IR (NaCl, cm ⁻¹ ): 3175, 2955, 29
17, 2851, 1692, 1628, 1468, 13
77, 1215, 1211

Production Example 5: Nε- (2-hydroxy-3-
Dodecyloxy) propyl-L-lysine hydrochloride 18.3 g of L-lysine hydrochloride (0.
1 mol) with 8.0 g (0.2 mol) of sodium hydroxide.
l) was dissolved in 100 ml of water, and isopropanol 100
ml was added. Under heating and stirring under reflux, 24.2 g (0.1 mol) of dodecylglycidyl ether was added dropwise over 30 minutes, and the mixture was stirred under reflux for 3 hours. After confirming the disappearance of dodecyl glycidyl ether by TLC and gas chromatography, the mixture was cooled to 40 ° C. or lower and neutralized by adding 10.1 g (0.1 mol) of 36% hydrochloric acid.

The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (Kieselgel 60, developing solvent: chloroform / methanol / acetic acid = 3/1 / 0.5) to give Nε- (2-hydroxy-3- 10.1 g of dodecyloxy) propyl-L-lysine hydrochloride (yield 2)
3.7%).

TLC (butanol / acetic acid / water = 4/1/2): Rf = 0.42 ESI mass spectrum: 389.4 (MH ⁺ ) IR (NaCl, cm ⁻¹ ): 2955, 2923, 2853, 1620 1586, 1468, 1120

Production Example 6 In a three-necked round bottom flask, 17.4 g (0.1 mol) of L-arginine was dissolved in 100 ml of water, and 100 ml of isopropanol was added. Under heating reflux and stirring, “Heroxy 8” (AC I Japan
25.6 g (0.1 mol) was added dropwise over 30 minutes, and the mixture was stirred under reflux for 3 hours. TL
After confirming the disappearance of glycidyl ether by C and gas chromatography, the mixture was cooled to 40 ° C. or lower, and 12.9 g of DL-pyrrolidonecarboxylic acid (0.1 m
ol).

After isopropanol was distilled off under reduced pressure, the reaction solution was poured into cold acetone, and the crystals were separated and dried.
(2-hydroxy-3-dodecyloxy) propyl-L
-Arginine DL-pyrrolidone carboxylate and N-
50.9 g of a mixture of (2-hydroxy-3-tetradecyloxy) propyl-L-arginine / DL-pyrrolidonecarboxylate was obtained.

ESI mass spectrum: 417.5 (MH
⁺ ), 445.5 (MH ⁺ )

Production Example 7 L-arginine (45.9 g, 0.26 mol), water (29.2 g) and ethanol (42.2 g) were added to a three-necked round bottom flask, and the mixture was heated and stirred at 75 ° C. and dispersed. 73.6 g (0.29 mol) of "Heroxy 8" (manufactured by AC I Japan Limited) was added dropwise over 3 hours, and the mixture was further stirred for 3 hours. After confirming the disappearance of glycidyl ether by TLC and gas chromatography, the mixture was cooled to 40 ° C. or lower, 30.6 g (0.18 mol) of 47% hydrobromic acid was added, and 47% hydrobromic acid was further removed. In addition, the pH was adjusted to 5.2 to obtain 221 g of a liquid composition having a solid content of about 61%.

Production Example 8: 45.9 g (0.26 mol) of L-arginine, 29.2 g of water and 42.2 g of ethanol were added to a three-necked round-bottomed flask, and the mixture was heated with stirring at 75 ° C. and dispersed. 73.6 g (0.29 mol) of "Heroxy 8" (manufactured by AC I Japan Limited) was added dropwise over 3 hours, and the mixture was further stirred for 3 hours. After confirming the disappearance of glycidyl ether by TLC and gas chromatography, the mixture was cooled to 40 ° C. or lower, and 32.0 g (0.18 mol) of 50% lactic acid was added.
Lactic acid was added to adjust the pH to 5.2 to obtain 223 g of a liquid composition having a solid content of about 61%.

Production Example 9 45.9 g (0.26 mol) of L-arginine, 12.9 g of water and 51.4 g of propylene glycol were added to a three-necked round-bottomed flask, and the mixture was heated with stirring at 75 ° C. and dispersed. 73.6 g of "Heroxy 8" (manufactured by AC I Japan Limited) (0.29 mo
l) was added dropwise over 3 hours, and the mixture was further stirred for 3 hours. TL
After confirming the disappearance of glycidyl ether by C and gas chromatography, the mixture was cooled to 40 ° C. or lower to obtain 184 g of a liquid composition having a solid content of about 65%.

Production Example 10: In a three-necked round bottom flask, 17.4 g (0.1 mol) of L-arginine, 10.6 g of water and 42.2 g of propylene glycol were added, and the mixture was heated and stirred at 75 ° C. and dispersed. 35.4 g (0.1 mol) of 2-octyldodecyl glycidyl ether was added dropwise over 3 hours, and the mixture was further stirred for 3 hours. After confirming the disappearance of glycidyl ether by TLC and gas chromatography, the mixture was cooled to 40 ° C. or lower to obtain 105 g of a liquid composition having a solid content of about 50%.

Test Example 1 Compatibility Test with Anionic Surfactant 10 ml of a 1% aqueous solution of sodium polyoxyethylene lauryl ether sulfate (LES) and sodium dodecyl sulfate (SDS), which are anionic surfactants, were prepared. To this, 10 ml of a 1% aqueous solution of each surfactant solution shown in the following table was gradually added at 25 ° C., and a blue coloring point and a cloudiness point were visually determined.

[0100]

[Table 1]

Test Example 2 The compositions shown in Tables 2 to 5 below (indicated by pure weight%, total amount 100
%) Of hair shampoos, and five specialized panelists use these hair shampoos, (a) finger passing at the time of hair washing, (b) moist feeling after drying, (c) good combing after drying, Sensory evaluation was performed on (d) smoothness after drying and (e) no stiffness after drying. The samples of Production Examples 1, 7 and 8 were freeze-dried in advance,
The preparation was performed by removing water and ethanol. The evaluation results are also shown in Tables 2 to 5.

The evaluation was a relative evaluation using Comparative Example 2 in Table 2 as a standard, and an average value was calculated based on the following criteria.
Very good when the average value is 4.5 or more (◎), 3.5
The case of ４4.4 was evaluated as good (○), the case of 2.5-3.4 was evaluated as normal (△), and the case of 2.4 or less was evaluated as poor (×).

<Evaluation Criteria> (a) Finger passing at the time of hair washing 5: Finger passing is better than the standard product 4: Finger passing is better than the standard product 3: Same as the standard product 2: Finger passing is worse than the standard product 1: Finger passing is worse than standard product

(B) Moist feeling after drying 5: Moist than standard product 4: slightly moist than standard product 3: equivalent to standard product 2: slightly moist than standard product 1: not moist than standard product

(C) Good combability after drying 5: Better combability than the standard product 4: Slightly better combability than the standard product 3: Same as the standard product 2: Slightly worse than the standard product 1: Combing is worse than standard products

(D) Smoothness after drying 5: Smooth than standard 4: Slightly smoother than standard 3: Equal to standard 2: Slightly less than standard 1: Less smooth than standard

(E) Less stiffness after drying 5: Less stiffness than standard product 4: Slightly less stiffness than standard product 3: Same as standard product 2: Slightly stiffer than standard product 1: There is more stiffness than the standard product

[0108]

[Table 2]

[0109]

[Table 3]

[0110]

[Table 4]

[0111]

[Table 5]

Test Example 3 Composition shown in Table 6 below (expressed as pure weight%, total amount 100%)
Are prepared and applied to a wick (evaluation device in which human hair is planted on the head of a mannequin). The hair wax is applied by five expert panelists (b) a moist feeling after drying, and (c) a moist feeling after drying. Sensory evaluation was performed on good combability and (d) smoothness after drying. The evaluation is Comparative Example 7 in Table 6.
Was used as a standard, and the evaluation was performed in the same evaluation standard as in Test Example 2. Table 6 also shows the evaluation results.

[0113]

[Table 6]

Test Example 4 Composition shown in Table 7 below (indicated by pure weight%, total amount 100%)
Was prepared, mixed with the same amount of 6% aqueous hydrogen peroxide, applied evenly to 5 bundles of Chinese hair, allowed to stand at room temperature for 20 minutes, and then washed with a commercially available shampoo. Sensory evaluation was performed by five expert panelists on (b) moist feeling after drying, (c) good combability after drying, and (d) smoothness after drying. Evaluation is Comparative Example 1 in Table 7.
Relative evaluation with 0 as a standard was performed according to the same evaluation criteria as in Test Example 2. Table 5 also shows the evaluation results.

[0115]

[Table 7]

Test Example 5 Composition shown in Table 8 below (expressed as pure weight%, total amount 100%)
Was prepared and used by five professional panelists, and sensory evaluation was performed for (a) lack of firmness after drying and (b) moist feeling after drying.
In the sensory evaluation, the comparative example 13 in Table 8 was used as a relative evaluation, and the average value was calculated according to the following criteria. The average value of 4.5 or more was very good (良好), 3.5 to 4.5. 4 is good (○), 2.5-3.4 is normal (△),
The case of 2.4 or less was regarded as defective (x). Table 8 shows the evaluation results.
Shown in

<Evaluation Criteria> (a) Lack of Tightness after Drying 5: Less Tough Than Standard Product 4: Not Tougher Than Standard Product 3: Equal to Standard Product 2: Tighter Than Standard Product 1: Than Than Standard Product Pull

(B) Moist feeling after drying 5: Moist than standard product 4: slightly moist than standard product 3: equivalent to standard product 2: slightly moist than standard product 1: not moist than standard product

[0119]

[Table 8]

Test Example 6 Composition shown in Table 9 below (indicated by weight of pure content, total amount 100%)
Of solid soap, prepared by five professional panelists,
Sensory evaluation was performed on (a) lack of tightness after drying and (b) moist feeling after drying. In the evaluation, a relative evaluation was made using Comparative Example 16 in Table 9 as a standard, and the evaluation was performed according to the same evaluation criteria as in Test Example 5. The sample of Production Example 1 was prepared by freeze-drying in advance to remove ethanol and water. Table 9 also shows the evaluation results.

[0121]

[Table 9]

Test Example 7 Compositions shown in Table 10 below (indicated by pure weight%, total amount 100)
%), And five professional panelists use it,
Sensory evaluation was performed on (a) lack of tightness after drying and (b) moist feeling after drying. In the evaluation, a relative evaluation was made using Comparative Example 18 in Table 10 as a standard, and the same evaluation criteria as in Test Example 5 were used. Table 10 also shows the evaluation results.

[0123]

[Table 10]

Test Example 8 Compositions shown in Table 11 below (indicated by pure weight%, total amount 100
%) Of make-up, prepared by five professional panelists, (a) lack of tightness after drying, and (b)
The sensory evaluation was performed on the moist feeling after drying. The evaluation was a relative evaluation using Comparative Example 20 in Table 11 as a standard, and was performed according to the same evaluation criteria as in Test Example 5. Table 11 also shows the evaluation results.

[0125]

[Table 11]

Example 55 The composition shown in Table 12 below (expressed as a percentage by weight of pure content, total amount of 100)
%) Of a hand soap was prepared. The sample of Production Example 1 was prepared by freeze-drying in advance to remove water and ethanol. This hand soap had little feeling of tension and was excellent in moist feeling.

[0127]

[Table 12]

Example 56 The compositions shown in Table 13 below (expressed as pure weight%, total amount 100
%) Of a liquid facial cleanser was prepared. The sample of Production Example 1 was prepared by freeze-drying in advance to remove water and ethanol. This liquid facial cleanser had a less firm feeling and an excellent moist feeling.

[0129]

[Table 13]

Example 57 The compositions shown in Table 14 below (expressed as pure weight%, total amount 100
%) Was prepared. This facial cleansing powder had little feeling of tension and was excellent in moist feeling.

[0131]

[Table 14]

Example 58 The compositions shown in Table 15 below (indicated by pure weight%, total amount 100)
%) Was prepared. The sample of Production Example 1 was prepared by freeze-drying in advance to remove water and ethanol. The shaving cream had a less firm feeling and a better moist feeling.

[0133]

[Table 15]

Reference Example 1 Primary irritation to skin and ocular mucosa was measured by the following test method.

(1) Primary skin irritation test Four New Zealand white male rabbits were patch-adhered with a patch test bandage soaked with 0.3 ml of a 1% test compound aqueous solution for 24 hours, and stimulated 24 hours after removal of the patch. The properties were evaluated according to the Draize's evaluation criteria, and were determined according to the following criteria.

[0136]

(2) Primary mucosal mucosa test The lower eyelids of four New Zealand white male rabbits were made into a bag, and 0.1 ml of a 1% aqueous solution of a surfactant was instilled. 24 hours after instillation,
The irritation was evaluated according to Draize's evaluation criteria, and judged according to the following criteria.

[0138]

[0139]

[Table 16]

Reference Example 2 Biodegradability Test OECD Chemicals Test Guideline 301C Modified MIT
The biodegradation test was performed for 28 days according to the I test (I) -1981. In this test, activated sludge from a sewage treatment plant was used as a microorganism source, and a closed system oxygen consumption automatic measuring device (B
The biochemical oxygen consumption (BOD) was continuously measured by an OD measuring device. The degree of biodegradation of the specimen is shown in Table 17 below. The biodegradability of the sample for 28 days was 60.0%. Also,
The degree of biodegradation of aniline in the reference test group was 40% or more in 7 days, confirming the establishment of this test.

[0141]

[Table 17]

[0142]

Industrial Applicability The cosmetic composition of the present invention has an excellent conditioning effect on the hair and has an improved tightness to the skin, and is used for various hair and skin cosmetics. Can be.

Claims (1)

[Claims] 1. An active ingredient comprising one or more (A) selected from a basic amino acid derivative represented by the following general formula (1) and a salt thereof and one or more (B) selected from an anionic surfactant. A cosmetic composition characterized by containing. Embedded image [In the above general formula (1), R ¹ represents a linear or branched alkyl or alkenyl group having 8 to 22 carbon atoms, X represents a hydrogen atom or a substituent represented by the following general formula (2) And k represents an integer of 0 to 5, and when k = 0, Y
Represents a substituent represented by the following general formula (3);
In the case where = 1 to 5, Y represents an amino group. ] [In the general formula (2), R ² is the same as or different from R ¹ and represents a linear or branched alkyl or alkenyl group having 8 to 22 carbon atoms. ] [In the general formula (3), m represents an integer of 1 to 5, and Z represents a substituent of any of the following (I) to (IV). ]