JPH11106316A - Cosmetic - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a cosmetic composition which gives the hair no greasy feeling and excellent combing and conditioning effect and gives the skin excellent sense of use by using a specific basic amino acid derivative and an amphoteric surfactant. SOLUTION: This cosmetic contains (A) 0.01-10 wt.% of 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 1-5, Y is an amino group] and salts thereof, and (B) 0.01-50 wt.% of one or more selected from amphoteric 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, and more particularly, to one or more of a specific derivative of a basic amino acid and a salt thereof (component (A)) and one or more amphoteric surfactants.
In addition to the cosmetic composition containing at least one species (component (B)) as an active ingredient, and components (A) and (B),
The present invention relates to a cosmetic composition containing one or more anionic surfactants (component (C)) as an active ingredient.

[0002]

2. Description of the Related Art In hair washing, the oil and fat components of the hair are removed more than necessary, and after washing, the hair loses its smoothness and becomes a stiff and hard feel, and the combing becomes poor, and splitting and split ends are likely to occur. Is often a problem.

[0003] In order to improve such a problem, a component having a conditioning action is blended into a hair cosmetic composition. Alkyl quaternary ammonium salts such as dialkyldimethylammonium chloride and monoalkyltrimethylammonium chloride are most widely used as such conditioning components.

However, alkyl quaternary ammonium salts are problematic in that they are highly irritating to the skin and mucous membranes and have poor biodegradability. Therefore, development of a conditioning agent that replaces alkyl quaternary ammonium salts has been demanded. Was.

As a conditioning agent other than the alkyl quaternary ammonium salt, an alkylamidoamine salt 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.

On the other hand, amphoteric surfactants are often used in various cosmetic compositions such as shampoo, rinse-in shampoo, hair color, hair manicure, body shampoo and the like for the purpose of improving foaming. Amphoteric surfactants are in the molecule,
It is characterized by having one or more anionic groups and cationic groups at the same time, and is generally less irritating and more safe than ionic surfactants. However, there was a problem that there was a slimy feeling on the sensory side.

[0007]

SUMMARY OF THE INVENTION An object of the present invention is to provide a less slimy feeling to hair, excellent conditioning effects such as combability, smoothness and moist feeling, and excellent moisturizing and slimy feeling to skin. To provide a cosmetic composition.

[0008]

Means for Solving the Problems The inventors of the present invention have conducted intensive studies in view of the above situation, and as a result, have found that amphoteric surfactants, glycidyl ether and / or 1,2-epoxyalkane, and basic amino acids such as arginine and lysine are available. It has been found that the above object can be achieved by using a basic amino acid derivative obtained by reacting with the above, and the present invention has been completed based on such findings.

That is, the present invention provides 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 an active ingredient at least one kind (A) and at least one kind (B) selected from amphoteric surfactants. The present invention also relates to a cosmetic composition containing, as an active ingredient, at least one kind selected from anionic surfactants (C) in addition to the components (A) and (B).

[0010]

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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, j represents an integer of 0 or 1, and X represents a hydrogen atom. Or a substituent represented by the following general formula (2),
k represents an integer of 0 to 5, when k = 0, Y represents a substituent represented by the following general formula (3), and when k = 1 to 5, Y represents an amino group. ]

[0012]

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In the general 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, and n is 0 or 1
Indicates an integer. ]

[0014]

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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). ]

[0016]

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[0017]

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) Glycidyl ether or epoxyalkane represented by the following general formula (5) under alkaline conditions using an organic solvent such as a lower alcohol or a polyhydric alcohol, or a mixed solvent of these organic solvents and water. By doing so, it can be easily manufactured. For example, the reaction of an amino acid with an epoxy alkane is disclosed in
2417.

[0019]

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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. ]

[0021]

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[In the above formula, R ⁴ represents a linear or branched alkyl or alkenyl group having 8 to 22 carbon atoms. ]

In the basic amino acid derivative represented by the general formula (1), the one obtained by reacting glycidyl ether with a basic amino acid is the one obtained by reacting an epoxy alkane with a basic amino acid. More preferred. An amino acid derivative obtained by reacting an acidic amino acid or a neutral amino acid with glycidyl ether or epoxy alkane does not exhibit a conditioning effect as in the present invention.

The glycidyl ether represented by the general formula (4) can be obtained, for example, by reacting a saturated or unsaturated natural or synthetic higher 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).

Examples of the epoxy alkane represented by the general formula (5) include “A” manufactured by Daicel Chemical Industries, Ltd.
OEX "series.

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.

Among the basic amino acids, for example, in the case of lysine and ornithine, the binding sites for glycidyl ether or epoxy alkane are presumably preferentially ε-amino and δ-amino, respectively.
It may be one that has reacted with an amino group. Further, two or more glycidyl ethers or epoxyalkanes may be reacted with any of an ε-amino group, a δ-amino group and an α-amino group. Further, one molecule (two molecules in total) reacted with an ε-amino group (δ-amino group in ornithine) and α-amino group, respectively, or three molecules of glycidyl ether or epoxy alkane per one basic amino acid molecule or A compound having four molecules added may be used.
For example, the following eight kinds of compounds (6) to (13) are exemplified as the basic amino acid derivative of the present invention generated in the reaction between glycidyl ether and lysine.

[0028]

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[0029]

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[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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[In the above formulas (6) to (13), R ³ has the same meaning as described above. However, as described later, (8) to (1)
In the compound of 3), 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 or epoxy alkane is added to one molecule of a basic amino acid.

In the reaction of a glycidyl ether or epoxy alkane with 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 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 and polyhydric alcohols are usually used. Examples of lower alcohols include methyl alcohol, ethyl alcohol, n-propyl alcohol, isopropyl alcohol, n-butyl alcohol and the like, and examples of polyhydric alcohols include glycerin, 1,3-
Butylene glycol, propylene glycol, dipropylene glycol, isoprene glycol and the like. 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. Further, in order to increase the solubility of the basic amino acid, it is more preferable to use these organic solvents and water in combination. The mixing ratio between the organic solvent such as lower alcohol and polyhydric alcohol and water differs depending on the type of amino acid and the type of glycidyl ether or epoxy alkane.
Organic solvent: water = 100: 0 to 10:90, preferably 1: 1 to 9: 1. If the proportion of the organic solvent is low, the solubility of the glycidyl ether or epoxy alkane is low, and the reaction rate is significantly reduced.

The reaction temperature varies depending on the type and composition of the reaction solvent, but is, for example, usually in the range of 70 to 100 ° C., preferably 80 to 95 ° C. in the case of isopropyl alcohol, and usually in the range of 60 to 78 in the case of ethyl alcohol. 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 or epoxy alkane may be batch addition before heating or divided addition or continuous addition (continuous dropping) after the start of heating. It is preferable to drop continuously after the start.

The product obtained by the reaction of glycidyl ether or epoxy alkane with a basic amino acid is usually not a single compound, but glycidyl ether or epoxy alkane 1 per basic amino acid molecule.
It is a mixture of a molecule added and two or more molecules added. These mixtures may be isolated and purified into single compounds by, for example, chromatography or the like, and then one or more of them may be used as a raw material of the cosmetic composition of the present invention, or may be used as a mixture. Good. 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 or epoxyalkanes are added to one basic amino acid molecule, the chain lengths of the plurality of added glycidyl ethers or epoxyalkanes may be the same or different. . When the reaction is carried out using a mixture of glycidyl ethers or epoxyalkanes having different chain lengths, the resulting composition is usually a mixture of those having the same chain length and those having different chain lengths. For example, when a reaction is performed using arginine with "Heoxy 8" (mixture of dodecyl glycidyl ether and tetradecyl glycidyl ether) manufactured by AC I Japan Limited, the basic amino acid derivative of the present invention produced is (14) to (18). These may be isolated and purified for each single compound as described above, or may be used as a mixture.

[0043]

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[0044]

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[0045]

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[0046]

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[0047]

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When the reaction is carried out using a mixture of glycidyl ether and epoxy alkane, the resulting composition usually has a type in which both glycidyl ether and epoxy alkane are added within the same basic amino acid molecule. included. Of course, these compounds may be isolated and purified for each single compound as described above, or may be used as a mixture.

The reaction mixture obtained by reacting glycidyl ether or epoxy alkane with a basic amino acid may be used without any purification treatment if it does not interfere, or the reaction solvent may be distilled off if necessary. Can be used as a raw material for 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.

The salt of the basic amino acid derivative represented by the general formula (1) includes, 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, pyrrolidonecarboxylate, citrate, lactate, glycolate, glutamate, and aspartate.

Examples of the amphoteric surfactant which is the second essential component (B) of the cosmetic composition of the present invention include a betaine-type amphoteric surfactant and an imidazoline-type amphoteric surfactant.

Examples of the betaine-type amphoteric surfactant include carbobetaine-type amphoteric surfactant, amidobetaine-type amphoteric surfactant, sulfobetaine-type amphoteric surfactant,
Examples thereof include a hydroxysulfobetaine-type amphoteric surfactant, an amidosulfobetaine-type amphoteric surfactant, and a phosphobetaine-type amphoteric surfactant.

Such betaine-type amphoteric surfactants include:
In other words, for example, it is a betaine type surfactant having an alkyl group, an alkenyl group or an acyl group having 8 to 24 carbon atoms, more specifically, coconut oil alkyldimethylaminoacetate betaine, coconut oil fatty acid amide propyl Examples include betaine dimethylaminoacetate, betaine stearyldihydroxyethylaminoacetate, laurylhydroxysulfobetaine, laurylsulfobetaine, and laurylphosphobetaine. These betaine surfactants can be used alone or in combination of two or more.

The imidazoline-type amphoteric surfactants include
For example, 2-alkyl having an alkyl group having 8 to 22 carbon atoms
Alkyl-N-carboxymethyl-N-hydroxyethylimidazolinium betaine, 2-alkyl-N-carboxyethyl-N-hydroxyethylimidazolinium betaine, 2-alkyl-N-sodium carboxymethyl-N-carboxymethyloxy Ethyl imidazolinium betaine and the like. These can also be used alone or in combination of two or more.

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

More specifically, the amphoteric surfactant which is the second essential component (B) of the cosmetic composition of the present invention is exemplified by lauryl dimethylaminoacetic acid betaine, coconut oil alkylbetaine, stearyldimethylaminoacetic acid. Betaine, stearyl dihydroxyethyl betaine, amide propyl betaine laurate, coconut oil fatty acid amide propyl betaine solution, palm kernel oil fatty acid amide propyl betaine solution, ricinoleic acid amide propyl betaine solution,
N-coconut fatty acid acyl-N-carboxyethyl-N-
Sodium hydroxyethylethylenediamine, palm kernel oil fatty acid acyl-N-carboxyethyl-N-hydroxyethylethylenediaminesodium, 2-alkyl-N-carboxymethyl-N-hydroxyethylimidazolium betaine, undecyl-N-carboxymethylimidalinium betaine , An alkyldiaminoethylglycine hydrochloride solution, a bis (stearyl-N-hydroxyethylimidazoline) chloroacetic acid complex, and the like.

Component (A) in the cosmetic composition of the present invention
Is appropriately determined depending on the intended product, and is not particularly limited, but is preferably 0.01 to 10% by weight, particularly preferably 0.1 to 5% by weight. 0.0
If the amount is less than 1% by weight, the effect of the present invention may not be sufficiently exerted. If the amount exceeds 10% by weight, a stiff feeling or a squeaky feeling may be caused to the hair.

Component (B) in the cosmetic composition of the present invention
Is appropriately determined depending on the intended product and is not particularly limited, but is usually used in the range of 0.1 to 50% by weight.

The slimy feeling can be further improved by using the anionic surfactant which is the component (C) in addition to the components (A) and (B).

The anionic surfactants used in the present invention include, for example, alkyl sulfates such as lauryl sulfate, myristyl sulfate, cetyl sulfate, stearyl sulfate and oleyl sulfate, and alkyl phosphates such as lauryl phosphate. And salts thereof, polyoxyethylene lauryl ether sulfate,
Polyoxyethylene alkyl carboxylic acid such as polyoxyethylene alkyl ether sulfate such as polyoxyethylene myristyl ether sulfate, polyoxyethylene alkyl phenyl ether sulfate, polyoxyethylene lauryl ether acetate, polyoxyethylene tridecyl ether acetate Salt, octylphenoxydiethoxyethyl sulfonate, dodecylbenzene sulfonate, tetradecene sulfonate, dioctyl sulfosuccinate, lauryl sulfosuccinate, lauryl polyoxyethylene sulfosuccinate, polyoxyethylene monooleylamide sulfosuccinate , Oleic acid amide sulfosuccinate, lauroyl sarcosine, oleyl sarcosine, coconut oil fatty acid sarcosine and the like, alkyl sarcosine and salts thereof, N-alkyl N-methyl-β-alanine and salts thereof, polyoxyethylene coconut oil fatty acid monoethanolamide sulfate, polyoxyethylene alkyl ether phosphoric acid and salts thereof, laurate, myristate, palmitate, oleate, Palm oil fatty acid salts, higher fatty acid salts such as stearates, coco oil fatty acid ethyl ester sulfonates, N-coco oil fatty acid-glutamic acid salts, N-
Lauroyl-glutamate, N-myristoyl-glutamate, N-coconut fatty acid-aspartate, N
N-acyl-amino acid salts such as coconut oil fatty acid-glycine salt and N-coconut oil fatty acid-alanine salt. Examples of the types of these salts include sodium, magnesium, potassium, ammonium, diethanolamine, triethanolamine, arginine, lysine and the like.

The amount of the component (C) relative to the component (B) is not particularly limited, but is preferably a weight ratio of the component (C).
/ (B) = 1/10 to 10/1, more preferably 1/5 to 5/1.

If the amount of the anionic surfactant is too high, a squeaky feeling on the hair and a tight feeling on the skin may occur.

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, milky lotion, 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 nonionic surfactants include polyoxyethylene lauryl ether, polyoxyethylene myristyl ether, polyoxyethylene cetyl ether, polyoxyethylene isocetyl ether, polyoxyethylene setstearyl 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, and 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 epi chlorohydrin Lung-coconut oil alkylamine-dipropylenetriamine condensate, perfluoro polyether and the like.

Examples of other components include beeswax, beeswax, candelilla wax, carnauba wax, ibis wax, mokuro, rice bran wax, sara simanta wax,
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, 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,
Amino acids and their derivatives such as threonine, tyrosine, valine, etc .; estradiol and ethinylestradiol as female hormone agents; pantothenic acid and its derivatives as hair root activators, placenta extract, allantoin,
Photosensitizer 301, etc .; β-glycyrrhetinic acid, glycyrrhizic acid derivatives, allantoin, azulene, ε-aminocaproic acid, hydrocortisone, hinokitiol, etc. as anti-inflammatory agents; tranexamic acid as antiplasmin agent; zinc oxide, zinc sulfate, allantoinhydroxy as astringent agents Aluminum, aluminum chloride, aluminum sulfate, zinc sulfocarbonate, tannic acid, citric acid, lactic acid, etc .; natural products such as hamamelis, sardines, birch, rhubarb; etc .; menthol, camphor as a refreshing agent, estradiol and its esters as hormones Derivatives; estrone, ethinyl estradiol, cortisone and its ester derivatives; hydrocortisone and its ester derivatives, prednisone, prednisolone, etc .; as antihistamines Diphenhydramine hydrochloride, chlorferamine maleate; keratin exfoliating / dissolving agents such as sulfur, salicylic acid, and resorcinol; bactericides benzalkonium chloride, benzethonium chloride, halocarban, 2,4,4-trichloro-2-hydroxyphenol, Triclosan; chamomile extract, eucalyptus oil extract as a natural product; carrot extract, aloe, sicon, lily, loofah, malonie, psyllium, safflower, etc .; , Para-aminobenzoic acid derivatives, methoxycinnamic acid derivatives, salicylic acid derivatives, urocanic acid and its derivatives, 4-tert-butyl-4′-
Methoxydibenzoylmethane, 2- (2′-hydroxy-5′-methylphenyl) benzotriazole, methyl anthranilate; malonier, β-carotene, etc. as natural products; pyrrolidone carboxylic acid and its salt as a humectant, 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, hydrolyzed silk, poly Polyamino acid salts such as aspartate and polyglutamate; dimethyl phthalate, 2-ethyl-1, 2-ethyl-1, as a repellent component for blood-sucking insects (mosquitoes, lice, fleas, mites, etc.)
3-hexanediol, bisbutylenetetrahydrofurfural, N, N-diethyl-m-toluamide and the like; preservatives include paraben derivatives, benzoic acid derivatives, salicylic acid derivatives and the like.

[0070]

【Example】

Hereinafter, the present invention will be described in more detail by way of examples, but the present invention is not limited to these examples.

Production Example 1 L-arginine (45.9 g, 0.26 mol), water (29.2 g) and ethanol (42.2 g) were added to a three-necked round-bottomed flask, and the mixture was heated, refluxed, stirred and dispersed at 75 ° C. 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 solution was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography (MERSE & 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 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. 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 KK) 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 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 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 N- (2-hydroxydodecyl) -L-arginine hydrochloride 17.4 g (0.1 mol) of L-arginine and 1,2-
Using 18.4 g (0.1 mol) of epoxide dodecane, N- (2-hydroxydodecyl) was obtained in the same manner as in Production Example 1.
13.0 g of L-arginine hydrochloride (yield 32.9)
%).

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 bottom 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, 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 9 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 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, 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 10: 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 bottom flask, and the mixture was heated with stirring at 75 ° C. and dispersed. "Heroxy 8" (manufactured by AC I Japan Limited) 73.6 g (0.29 m
ol) was added dropwise over 3 hours, and the mixture was further stirred for 3 hours. T
After confirming the disappearance of the glycidyl ether by LC 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 11: In a three-necked round bottom flask, 17.4 g (0.1 mol) of L-arginine, 4.8 g of water and 19.1 g of propylene glycol were added, and the mixture was heated with stirring at 75 ° C. and dispersed. 18.4 g of 1,2-epoxide decane
(0.1 mol) was added dropwise over 3 hours, and the mixture was further stirred for 3 hours. After confirming the disappearance of the epoxy by TLC and gas chromatography, the mixture was cooled to 40 ° C. or lower to obtain 60 g of a liquid composition having a solid content of about 60%.

Production Example 12: 29.2 g (0.1 mol) of a 50% aqueous solution of L-lysine and 4.9 water were placed in a three-necked round bottom flask.
g and 19.6 g of ethanol were added, and the mixture was heated and stirred at 75 ° C. and dispersed. 1,2-epoxyoctadecane 24.5
g (0.1 mol) was added dropwise over 3 hours, and the mixture was further stirred for 3 hours. After confirming that 1,2-epoxyoctadecane had disappeared by TLC and gas chromatography, the mixture was cooled to 40 ° C. or lower to obtain 78 g of a liquid composition having a solid content of about 50%.

Production Example 13: In a three-necked round-bottomed 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 with stirring 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%.

Production Example 14: In a three-necked round bottom flask, 17.4 g (0.1 mol) of L-arginine, 6.9 g of water and 17.6 g of ethanol were added, and the mixture was heated with stirring at 75 ° C. and dispersed. 18.4 g of 1,2-epoxide decane (0.1
mol) was added dropwise over 3 hours, and the mixture was further stirred for 3 hours.
After confirming that 1,2-epoxide dodecane had disappeared by TLC and gas chromatography, the mixture was cooled to 40 ° C. or lower, and 17.2 g of 47% hydrobromic acid (0.1 mol) was added.
1) was added, and the pH was adjusted to 6.0 by further adding 47% hydrobromic acid to obtain 77 g of a liquid composition having a solid content of about 50%.

Production Example 15: In a three-necked round-bottomed flask, 17.4 g (0.1 mol) of L-arginine, 13.4 g of water and 22.4 g of ethanol were added, and the mixture was heated with stirring at 75 ° C. and dispersed. 18.4 g of 1,2-epoxide decane (0.
1 mol) was added dropwise over 3 hours, and the mixture was further stirred for 3 hours. According to TLC and gas chromatography, 1,2-
After confirming that epoxide decane has disappeared, 40
Cooled to 18.0 g or less and cooled to 18.0 g of 50% lactic acid (0.1 mol
l) was added, and the pH was adjusted to 6.0 by further adding 50% lactic acid to obtain 89 g of a liquid composition having a solid content of about 50%.

Production Example 16: In a three-necked round-bottomed flask, 17.4 g (0.1 mol) of L-arginine, 27.5 g of water and 30.7 g of ethanol were added, and the mixture was heated with stirring at 75 ° C. and dispersed. "Heroxy 8" (manufactured by AC I Japan Limited) 25.6 g (0.1 mol) 1,2
-18.4 g (0.1 mol) of epoxide decane was added dropwise over 3 hours, and the mixture was further stirred for 3 hours. After confirming that glycidyl ether and 1,2-epoxide decane had disappeared by TLC and gas chromatography, the mixture was cooled to 40 ° C. or lower and cooled to 70% glycolic acid 10.8%.
g (0.1 mol), and 70% glycolic acid was further added to adjust the pH to 6.0 to obtain 122 g of a liquid composition having a solid content of about 50%.

Test Example 1 Compositions shown below in Tables 1 to 4 (indicated by pure weight%, total amount 100
%) Hair shampoo was prepared and used by five professional panelists as a commercial shampoo. (A) No slimy feeling when used, (b) Moist feeling after drying, (c) Combing after drying And (d) smoothness after drying were evaluated organoleptically. Production Examples 1, 8, 9, 14, 15, and 1
Sample No. 6 was prepared by freeze-drying in advance to remove ethanol and water. The evaluation results are also shown in Tables 1 and 2.

The evaluation was a relative evaluation using Comparative Example 1 in Table 1 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) No slimy feeling during use 5: Less slimy feeling than standard product 4: Slightly less slimy feeling than standard product 3: Same as standard product 2: Slightly slicker than standard product 1 : More slimy than standard products

(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: Smoother than standard 4: Slightly smoother than standard 3: Same as standard 2: Slightly less than standard 1: Less smooth than standard

[0104]

[Table 1]

[0105]

[Table 2]

[0106]

[Table 3]

[0107]

[Table 4]

Test Example 2 Composition shown in Table 5 below (indicated by weight of pure content, total amount 100%)
Was prepared, mixed with the same amount of 6% aqueous hydrogen peroxide, applied evenly to five bundles of gray 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 7 in Table 5.
Was used as a standard, and the evaluation was performed according to the same evaluation criteria as in Test Example 1. Table 5 also shows the evaluation results.

[0109]

[Table 5]

Test Example 3 Compositions shown in Table 6 below (indicated by weight of pure content, total amount 100%)
Is prepared and applied to a hair switch washed with a 1% aqueous solution of sodium lauryl ether sulfate, and then washed with running water. Five expert panelists (b) a moist feeling after drying, and (c) a good combability after drying. , (D) Sensory evaluation was performed on smoothness after drying. The evaluation was a relative evaluation using Comparative Example 10 in Table 6 as a standard, and was performed according to the same criteria as in Test Example 1. Table 6 also shows the evaluation results.

[0111]

[Table 6]

Test Example 4 Body shampoos having the compositions shown in Tables 7 and 8 below (expressed as pure weight%, total amount 100%) were prepared, and five expert panelists were allowed to use these body shampoos.
Sensory evaluation was performed on the lack of slimy feeling during use and (b) the moist feeling after drying. The evaluation is Comparative Example 13 in Table 7.
Was used as a standard, and the evaluation was performed in the same manner as in Test Example 1. Table 7 also shows the evaluation results.

[0113]

[Table 7]

[0114]

[Table 8]

<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.

[0117]

(2) Primary test of ocular mucosa Primary eyelids of four New Zealand white male rabbits were put in a bag shape, 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.

[0119]

[0120]

[Table 9]

<Reference Example 2> Biodegradability test OECD Chemical 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 10 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.

[0122]

[Table 10]

[0123]

EFFECTS OF THE INVENTION According to the present invention, a cosmetic composition having less slimy feeling to the hair, improved conditioning properties such as combability, smoothness, and moist feeling, and improved moisturizing and slimy feeling to the skin. A composition can be obtained.

Claims (2)

[Claims] 1. An active ingredient comprising one or more (A) selected from basic amino acid derivatives represented by the following general formula (1) and salts thereof and one or more (B) selected from amphoteric surfactants. A cosmetic composition characterized by containing. Embedded image [In the general formula (1), R ¹ represents a linear or branched alkyl or alkenyl group having 8 to 22 carbon atoms, j represents an integer of 0 or 1, X represents a hydrogen atom or Represents a substituent represented by the formula (2), and k is 0 to 5
And when k = 0, Y represents a substituent represented by the following general formula (3), and when k = 1 to 5, Y
Represents an amino group. ] [In the above general 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, and n represents an integer of 0 or 1. ] [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). ] 2. The cosmetic composition according to claim 1, further comprising (C) at least one selected from anionic surfactants in addition to the components (A) and (B).