JPH10114618A - Liquid cosmetic - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a liquid cosmetic containing an N-long chain acyl basic amino acid derivative and a chitosan compound, exhibiting good transparency, high moisture retainability and skin affinity, having a sufficient antimicrobial property, low in irritability and capable of having a proper viscosity. SOLUTION: This cosmetic contains one or more of compounds of formula I, formula II and formula III [RCO is a 6-20C fatty acid residue; X is NH2 , OCH3 , OC2 H5 , OCH2 C6 H5 , etc.; (n) is 3, 4] and their acid adduct salts, and chitisan, its derivative or their mixture as active ingredients. The compounds of formula I, formula II and formula III are contained in an amount of 0.001-0.5wt.%, and the chitosan is contained in an amount of 0.001-10wt.%. The compounds of formula I, formula II and formula III include N-hexanoyl-L- arginamide. The liquid cosmetic exhibits an antimirobial property against Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa, acne bacteria, Candida, Aspergillus niger, etc.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a liquid cosmetic which has a high affinity for skin, has excellent moisturizing properties and antibacterial activity, exhibits low irritation and good transparency, and can impart an appropriate viscosity. More specifically, it comprises one or more of N-long-chain acyl-basic amino acid derivatives and acid addition salts thereof, and one or more selected from chitosan, chitosan derivatives and salts thereof. Related to liquid cosmetics.

[0002]

2. Description of the Related Art Various antiseptic and antifungal agents such as isopropylmethylphenol, paraoxybenzoates, phenoxyethanol, and salicylates are used in liquid cosmetics containing a large amount of water in order to prevent deterioration in quality due to microbial contamination. Be blended. However, many of these antiseptic / antifungal agents have been reported as primary irritants, sensitizers or photosensitizers on the skin, and the amount of cosmetics is regulated in terms of cosmetics raw materials from the viewpoint of safety. In many cases, an effective antibacterial activity cannot be incorporated. further,
It is also known that even if the skin does not show an inflammatory reaction such as redness, rash, or edema, it gives discomfort such as stinging, burning, or tingling when using the cosmetic.

In consideration of the above-mentioned problems of the conventional antiseptic and fungicide, especially in the case of liquid cosmetics, "CAE"
N-Cocoil-L-arginine ethyl ester DL-pyrrolidone carboxylate, which is commercially available under the trade name of N-Length, which has long been known as a bactericidal detergent with a hydrophilic cationic surfactant. Attempts have been made to incorporate chain acyl basic amino acid derivatives and acid addition salts thereof.

[0004] However, N-long-chain acyl-basic amino acid derivatives and acid addition salts thereof have high antibacterial activity, low irritation, and are also preferable in terms of safety. If the viscosity is to be imparted, the negative charge adversely affects the antibacterial activity and the like of the N-long-chain acyl basic amino acid derivative and the like.
An anionic water-soluble polymer such as a carboxyvinyl polymer could not be used. On the other hand, when a water-soluble polymer such as amphoteric or nonionic is used, there is a problem that it is difficult to obtain good transparency.

[0005]

Therefore, in the present invention, it has high moisturizing property and antibacterial activity, is low in irritation, exhibits good transparency, and can impart appropriate viscosity.
Moreover, the present invention aims to provide a liquid cosmetic having high skin affinity.

[0006]

Means for Solving the Problems In order to solve the above problems, in the present invention, general formulas (1), (2),
And one or more of an N-long-chain acyl basic amino acid derivative represented by the general formula (3) and an acid addition salt thereof, and one or more selected from chitosan, a chitosan derivative and a salt thereof. To obtain a liquid cosmetic.

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(Wherein, in the general formulas (1) to (3), RC
O is a saturated or unsaturated fatty acid residue having 6 to 20 carbon atoms, and X is
_{-NH 2, -OCH 3, -OC 2} H 5, -OC 3 H 7, -OC 4 H 9
Or —OCH ₂ C ₆ H ₅ , and in the general formula (2), n represents 3 or 4. )

[0007]

The liquid cosmetic composition of the present invention exhibits good transparency and can have an appropriate viscosity depending on the content of one or more kinds of chitosan and the like. Furthermore, the antibacterial activity is synergistically improved, has excellent moisturizing properties and skin affinity, and has little irritation or sensitization to the skin, and there is no problem in safety.

[0008]

BEST MODE FOR CARRYING OUT THE INVENTION In the present invention, N-long-chain acyl basic amino acid derivatives include those represented by the following general formulas (1), (2) and (3).
These and their acid addition salts can be suitably used.

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(Wherein, in the general formulas (1) to (3), RC
O is a saturated or unsaturated fatty acid residue having 6 to 20 carbon atoms, and X is
_{-NH 2, -OCH 3, -OC 2} H 5, -OC 3 H 7, -OC 4 H 9
Or —OCH ₂ C ₆ H ₅ , and in the general formula (2), n represents 3 or 4. )

For example, N-hexanoyl-L-arginine amide, N-hexanoyl-L-arginine methyl ester, N-hexanoyl-L-arginine ethyl ester, N-hexanoyl-L-arginine ethyl ester
Hexanoyl-L-arginine propyl ester, N-hexanoyl-L-arginine butyl ester, N-hexanoyl-L-arginine benzyl ester, N-octanoyl-L-
Argininamide, N-octanoyl-L-arginine methyl ester, N-octanoyl-L-arginine ethyl ester, N-octanoyl-L-arginine propyl ester, N-octanoyl-L-arginine butyl ester, N-
Octanoyl-L-arginine benzyl ester, N-decanoyl-L-argininamide, N-decanoyl-L-arginine methyl ester, N-decanoyl-L-arginine ethyl ester, N-decanoyl-L-arginine propyl ester, N-decanoyl -L-arginine butyl ester, N-decanoyl-L-arginine benzyl ester, N-undecanoyl-L-arginine amide, N-undecanoyl-L-arginine methyl ester, N-undecanoyl-L-arginine ethyl ester, N-undecanoyl- L-arginine propyl ester, N-undecanoyl-L-arginine butyl ester, N-undecanoyl-L-arginine benzyl ester, N-dodecanoyl (lauroyl) -L-argininamide, N-dodecanoyl (lauroyl) -L-arginine methyl ester , N-Dodecanoyl (lauroyl) -L-
Arginine ethyl ester, N-dodecanoyl (lauroyl) -L-arginine propyl ester, N-dodecanoyl (lauroyl) -L-arginine butyl ester, N-dodecanoyl (lauroyl) -L-arginine benzyl ester, N-tetradecanoyl (myristoyl) ) -L-argininamide, N-tetradecanoyl (myristoyl) -L-arginine methyl ester, N-tetradecanoyl (myristoyl) -L-arginine ethyl ester, N-tetradecanoyl (myristoyl) -L-argininepropyl Ester, N-tetradecanoyl (myristoyl) -L-arginine butyl ester, N-tetradecanoyl (myristoyl) -L-arginine benzyl ester, N-hexadecanoyl (stearoyl) -L-argininamide, N-hexadeca Noyl (stearoyl) -L-arginine methyl e Stele, N-hexadecanoyl (stearoyl) -L-arginine ethyl ester, N-hexadecanoyl (stearoyl) -L-arginine propyl ester, N-hexadecanoyl (stearoyl) -L-arginine butyl ester, N
-Hexadecanoyl (stearoyl) -L-arginine benzyl ester, N-eicosanoyl-L-argininamide, N-eicosanoyl-L-arginine methyl ester, N
-Eicosanoyl-L-arginine ethyl ester, N-eicosanoyl-L-arginine propyl ester, N-eicosanoyl-L-arginine butyl ester, N-eicosanoyl-L-arginine benzyl ester, N-octadecenoyl (oleoyl) -L-arginine Amide, N-octadecenoyl (oleoyl) -L-arginine methyl ester, N-octadecenoyl (oleoyl) -L-arginine ethyl ester, N-octadecenoyl (oleoyl) -L
-Arginine propyl ester, N-octadecenoyl (oleoyl) -L-arginine butyl ester, N-octadecenoyl (oleoyl) -L-arginine benzyl ester, N-octadecadienoyl-L-argininamide, N-octadecadie Noyl-L-arginine methyl ester, N-octadecadienoyl-L-arginine ethyl ester, N-octadecadienoyl-L-arginine propyl ester, N-octadecadienoyl-L-arginine butyl ester, N-octa Decadienoyl-L-arginine benzyl ester, N-octadecatrienoyl-L-arginine amide, N-octadecatrienoyl-L-arginine methyl ester, N-octadecatrienoyl-L-arginine ethyl ester, N- Octadecatrienoyl-L-
Arginine propyl ester, N-octadecatrienoyl-L-arginine butyl ester, N-octadecatrienoyl-L-arginine benzyl ester, N-cocoyl-L-
Arginine amide, N-cocoyl-L-arginine methyl ester, N-cocoyl-L-arginine ethyl ester, N-
Cocoyl-L-arginine propyl ester, N-cocoyl-
L-arginine butyl ester, N-cocoyl-L-arginine benzyl ester, N-hexanoyl-L-lysine amide, N-hexanoyl-L-lysine methyl ester, N-hexanoyl-L-lysine ethyl ester, N-hexanoyl-L-
Lysine propyl ester, N-hexanoyl-L-lysine butyl ester, N-hexanoyl-L-lysine benzyl ester, N-octanoyl-L-lysine amide, N-octanoyl-L-lysine methyl ester, N-octanoyl-L-lysine ethyl Ester, N-octanoyl-L-lysine propyl ester, N-octanoyl-L-lysine butyl ester, N-
Octanoyl-L-lysine benzyl ester, N-decanoyl-L-lysine amide, N-decanoyl-L-lysine methyl ester, N-decanoyl-L-lysine ethyl ester, N-decanoyl-L-lysine propyl ester, N-decanoyl- L-lysine butyl ester, N-decanoyl-L-lysine benzyl ester, N-undecanoyl-L-lysine amide, N-undecanoyl-L-lysine methyl ester, N-undecanoyl-L-lysine ethyl ester, N-undecanoyl-L- Lysine propyl ester, N-undecanoyl-L-lysine butyl ester, N-undecanoyl-L-lysine benzyl ester, N-dodecanoyl (lauroyl) -L-lysine amide, N-dodecanoyl (lauroyl) -L-lysine methyl ester, N- Dodecanoyl (lauroyl) -L-lysine ethyl ester, N-dodecanoyl (lauroyl) -L-lysine propyl Ester, N- dodecanoyl (lauroyl) -L-
Lysine butyl ester, N-dodecanoyl (lauroyl)
-L-lysine benzyl ester, N-tetradecanoyl (myristoyl) -L-lysine amide, N-tetradecanoyl (myristoyl) -L-lysine methyl ester, N-tetradecanoyl (myristoyl) -L-lysine ethyl ester, N-tetradecanoyl (myristoyl) -L-lysine propyl ester, N-tetradecanoyl (myristoyl)
-L-lysine butyl ester, N-tetradecanoyl (myristoyl) -L-lysine benzyl ester, N-hexadecanoyl (stearoyl) -L-lysine amide, N-hexadecanoyl (stearoyl) -L-lysine methyl ester, N
-Hexadecanoyl (stearoyl) -L-lysine ethyl ester, N-hexadecanoyl (stearoyl) -L-lysinepropyl ester, N-hexadecanoyl (stearoyl) -L-lysine butyl ester, N-hexadecanoyl ( Stearoyl) -L-lysine benzyl ester, N-eicosanoyl-L-lysine amide, N-eicosanoyl-L-lysine methyl ester, N-eicosanoyl-L-lysine ethyl ester, N-eicosanoyl-L-lysine propyl ester, N-eicosanoyl -L-lysine butyl ester, N-eicosanoyl-L-lysine benzyl ester, N-octadecenoyl (oleoyl) -L-lysine amide, N-octadecenoyl (oleoyl) -L-lysine methyl ester, N-
Octadecenoyl (oleoyl) -L-lysine ethyl ester, N-octadecenoyl (oleoyl) -L-lysine propyl ester, N-octadecenoyl (oleoyl) -L
-Lysine butyl ester, N-octadecenoyl (oleoyl) -L-lysine benzyl ester, N-octadecadienoyl-L-lysine amide, N-octadecadienoyl-L-lysine methyl ester, N-octadecadienoyl- L-lysine ethyl ester, N-octadecadienoyl-L-lysine propyl ester, N-octadecadienoyl-L-lysine butyl ester, N-octadecadienoyl-L-lysine benzyl ester, N-octadecatrie Noyl-L-lysine amide, N-octadecatrienoyl-L-lysine methyl ester, N-octadecatrienoyl-L-lysine ethyl ester, N-octadecatrienoyl-L-lysine propyl ester, N-octadecatrie Noyl-L-lysine butyl ester, N-octadecatrienoyl-L-lysine benzyl ester, N-cocoyl-L-lysine amide, N-cocoyl-
L-lysine methyl ester, N-cocoyl-L-lysine ethyl ester, N-cocoyl-L-lysine propyl ester, N-
Cocoyl-L-lysine butyl ester, N-cocoyl-L-lysine benzyl ester, N-hexanoyl-L-histidine amide, N-hexanoyl-L-histidine methyl ester, N
-Hexanoyl-L-histidine ethyl ester, N-hexanoyl-L-histidine propyl ester, N-hexanoyl-L-histidine butyl ester, N-hexanoyl-L-histidine benzyl ester, N-octanoyl-L-histidine amide, N- Octanoyl-L-histidine methyl ester, N-octanoyl-L-histidine ethyl ester, N
-Octanoyl-L-histidine propyl ester, N-octanoyl-L-histidine butyl ester, N-octanoyl-L-histidine benzyl ester, N-decanoyl-L-histidine amide, N-decanoyl-L-histidine methyl ester, N- Decanoyl-L-histidine ethyl ester, N
-Decanoyl-L-histidine propyl ester, N-decanoyl-L-histidine butyl ester, N-decanoyl-L-histidine benzyl ester, N-undecanoyl-L-histidine amide, N-undecanoyl-L-histidine methyl ester, N- Undecanoyl-L-histidine ethyl ester, N-undecanoyl-L-histidine propyl ester, N-undecanoyl-L-histidine butyl ester, N
-Undecanoyl-L-histidine benzyl ester, N-dodecanoyl (lauroyl) -L-histidineamide, N-dodecanoyl (lauroyl) -L-histidine methyl ester, N-dodecanoyl (lauroyl) -L-histidine ethyl ester, N-dodecanoyl (Lauroyl) -L-histidine propyl ester, N-dodecanoyl (lauroyl)
-L-histidine butyl ester, N-dodecanoyl (lauroyl) -L-histidine benzyl ester, N-tetradecanoyl (myristoyl) -L-histidine amide, N-tetradecanoyl (myristoyl) -L-histidine methyl ester, N -Tetradecanoyl (myristoyl) -L-histidine ethyl ester, N-tetradecanoyl (myristoyl) -L-histidinepropyl ester, N-tetradecanoyl (myristoyl) -L-histidinebutyl ester, N-tetradecanoyl ( Myristoyl) -L-histidine benzyl ester, N-hexadecanoyl (stearoyl) -L-histidineamide, N-hexadecanoyl (stearoyl) -L-histidine methyl ester, N-hexadecanoyl (stearoyl) -L-histidine Ethyl ester, N-hexadecanoyl (stearoyl) -L-hist Ginpropyl ester, N-hexadecanoyl (stearoyl) -L-histidine butyl ester, N-hexadecanoyl (stearoyl) -L-histidine benzyl ester, N
-Eicosanoyl-L-histidine amide, N-eicosanoyl-L-histidine methyl ester, N-eicosanoyl-L-
Histidine ethyl ester, N-eicosanoyl-L-histidine propyl ester, N-eicosanoyl-L-histidine butyl ester, N-eicosanoyl-L-histidine benzyl ester, N-octadecenoyl (oleoyl)
-L-histidine amide, N-octadecenoyl (oleoyl) -L-histidine methyl ester, N-octadecenoyl (oleoyl) -L-histidine ethyl ester, N-octadecenoyl (oleoyl) -L-histidine propyl ester, N- Octadecenoyl (oleoyl) -L-histidine butyl ester, N-octadecenoyl (oleoyl) -L-histidine benzyl ester, N-octadecadienoyl-L-histidine amide, N-octadecadienoyl-L-histidine methyl ester N-octadecadienoyl-L-histidine ethyl ester, N-octadecadienoyl-L-histidine propyl ester, N-octadecadienoyl-L-histidine butyl ester, N-octadecadienoyl-L-histidine Benzyl ester, N-octadecatrienoyl-L-histidine amide, N-octadede Trienoyl -L- histidine methyl ester, N- octadecanoyl Triester octanoyl -L- histidine ethyl ester, N-
Octadecatrienoyl-L-histidine propyl ester, N-octadecatrienoyl-L-histidine butyl ester, N-octadecatrienoyl-L-histidine benzyl ester, N-cocoyl-L-histidine amide, N-cocoyl- L-histidine methyl ester, N-cocoyl-L-histidine ethyl ester, N-cocoyl-L-histidine propyl ester, N-cocoyl-L-histidine butyl ester, N-cocoyl-L-histidine benzyl ester, and their hydrochloric acid Salts, acetates, lactates, DL-pyrrolidone carboxylate, and the like.

In the present invention, one or more of the above-mentioned N-long-chain acyl basic amino acid derivatives and their acid addition salts are selected and used, and the content in the total amount of the liquid cosmetic is as follows: About 0.001 to 0.5% by weight is appropriate, and particularly about 0.001 to 0.2% by weight is preferable.

On the other hand, chitosan that can be used in the present invention is obtained by deacetylating chitin obtained from an skeleton of shellfish or the like as a raw material. A wide range of molecular weights can be used, including those with a low molecular weight. Also, Makromol. Chem. 178 3197-3202 (197
7), ibid., 176 1191-1195 (1975), ibid., 177 3589-3
600 (1976), the degree of deacetylation was 40
〜60% water soluble partially deacetylated chitin (water soluble chitosan) can also be used.

Also, chitosan derivatives in which a carboxymethyl group, hydroxyethyl group, hydroxypropyl group, sulfopropyl group, etc. are introduced into the 6-position hydroxyl group of the above-mentioned chitosans, monosaccharides, disaccharides and oligosaccharides in the 2-position amino group. sugar,
Derivatives into which dehydroascorbic acid, a hydroxyethyl group, a hydroxypropyl group, etc. have been introduced can also be used. These derivatives are described in Bull. Chem. Soc. Jpn. 26 143-1.
47 (1953), West German Patent 3432227, J. Chem.
Soc. Chem. Comm. 1153-1154 (1980), Nature 302 812-8.
14 (1983), Byopolymers 20 1413-1419 (1981), Carboh
ydr. Polymers 5 85-89 (1985), West German Patent 350
4095, 3541305 and the like.

In the present invention, one or more of these chitosans and chitosan derivatives are selected and used. Water-soluble chitosan and water-soluble chitosan derivatives can be dissolved in purified water and added as it is, but other chitosans are added in the form of salts of organic acids such as acetic acid, lactic acid, citric acid and pyrrolidone carboxylic acid. . The content in the total amount of the liquid cosmetic is suitably about 0.001 to 10.0% by weight, particularly preferably about 0.01 to 1.0% by weight.

The liquid cosmetic according to the present invention includes alcohols such as ethanol and isopropanol, glycerin, propylene glycol, and the like, as long as the effects of the present invention are not impaired.
Humectants such as dipropylene glycol, 1,3-butylene glycol, amino acids, etc., emollients such as vegetable oils and ester oils, 2-ethylhexyl paramethoxycinnamate, 2-hydroxy-4-methoxybenzophenone, 4-tert-butyl-4 '-
UV absorbers such as methoxydibenzoylmethane, anti-inflammatory agents such as β-glycyrrhetinic acid, glycyrrhizic acid derivatives, allantoin and azulene, astringents such as zinc oxide, zinc sulfate, allantoin hydroxyaluminum, aluminum chloride, glycolic acid, lactic acid, Cell activators such as vitamins A and nucleic acids, ascorbic acid salts, ascorbic acid derivatives, whitening agents such as arbutin, kojic acid, hamamelitannin, hair growth and hair restoration agents such as swertinogen, cepharanthin, γ-oryzanol, vitamin E Antioxidants, plant extracts, animal tissue extracts, fragrances, pigments, pigments, etc. can be blended, and moisturizing lotion, soft lotion, astringent lotion, washing lotion, multi-layer lotion , Skin aging prevention lotion, whitening lotion, hair restoration / hair restoration lotion, hair tonic, sant tan rosi Down, sunscreen lotion,
It can be provided in the form of a serum or the like.

[0015]

EXAMPLES Further, the present invention will be described in more detail with reference to examples.

First, the formulations of Examples 1 to 3 are shown in Table 1 as a moisturizing lotion according to the present invention. These are shown in Table 1.
It is prepared by sequentially adding (1) to (4) to (5).

[Table 1]

Subsequently, the formulations of Examples 4 to 6 are shown in Table 2 as moisturizing essences according to the present invention. These are shown in Table 2.
It is prepared by sequentially adding (1) to (4) to (5).

[Table 2]

Examples 1 to 3 of the present invention were evaluated for appearance, moisture retention, skin affinity, skin irritation and antibacterial properties. At this time, the comparative examples shown in Table 3 were also evaluated at the same time.

[Table 3]

(1) Observation of Appearance and Evaluation of Moisturizing Property and Skin Affinity Appearance observation was performed on the transparency of lotion. In addition, the moisturizing property and skin affinity were evaluated by sensory evaluation using 20 female panelists (20 to 50 years old) in a blind each using each sample. The results of the sensory evaluation were
"High; 5 points", "Slightly high; 4"
Points ”,“ Normal; 3 points ”,“ Slightly low; 2 points ”,“ Low;
It was scored as "1 point" and represented by the average value of 20 persons. These results are shown in Table 4.

[0020]

[Table 4] From Table 4, it can be seen that Examples of the present invention all show good transparency and are compared with Comparative Examples containing only one of N-long-chain acyl basic amino acid derivatives or salts thereof, or chitosans. It is clear that it has high moisturizing properties and skin compatibility. In Comparative Example 3 in which carboxymethyl chitosan was replaced with sodium hyaluronate, the cation of N-lauroyl-L-arginine ethyl ester acetate was
Interaction of sodium hyaluronate with the anion resulted in a decrease in transparency, and satisfactory evaluation of moisturizing property and skin affinity was not obtained.

(2) Skin irritation A group of 20 female panelists (20 to 50 years old) each used each sample in a blind, and felt irritating or unpleasant feelings such as pain, tingling or tingling during use. Pleasure was evaluated. The evaluation result is "very strong; 5
"Point", "somewhat strong; 4 points", "clearly;3"
"Point", "feel a little; 2 points", "feel subtle; 1"
The points were scored as “points” and “not felt; 0 points”, and the average value of each panel was calculated and shown in Table 5.

[0022]

[Table 5] As is clear from Table 5, Examples 1 to 3 of the present invention
In the use group, the feeling of irritation felt during use was hardly recognized. On the other hand, in Comparative Example 1b and Comparative Example 2 used groups which contain methyl paraoxybenzoate as an antibacterial agent, the evaluation points showing irritation are high, and in particular, 0.20% by weight of methyl paraoxybenzoate is contained. Comparative Example 2
A strong stimulus was recognized.

(3) Antibacterial Escherichia coli ( Escherich)
ia coli ), Staphylococcus aureu
s ), Pseudomonas aeruginosa , P. acnes ( P
ropionibacterium acnes ), fungi as Candida ( Cand)
ida albicans ) and black mold ( Aspergillus niger ) were inoculated with 10 ⁶ bacteria and 10 ⁵ fungi per gram of the sample, and cultured at 37 ° C. and 25 ° C., respectively. measured, when killed for bacteria, the fungi was determined that the antimicrobial properties when the viable count was 10 ³ or less is sufficient. The evaluation results are shown in Table 6 as ○ when sufficient antibacterial properties were observed, and × when not.

[0024]

[Table 6] In Table 6, in Examples 1 to 3 of the present invention, sufficient antibacterial properties were observed in all of the tested bacteria and fungi. On the other hand, in Comparative Example 1 in which N-hexanoyl-L-argininamide was replaced with polyoxyethylene (20E.O.) sorbitan monolaurate as a nonionic surfactant, antibacterial activity was observed for all bacteria and fungi. Is not allowed. Furthermore, methyl paraoxybenzoate was added to 0.1.
Even with the addition of 05% by weight, the antibacterial properties were not sufficient. On the other hand, in Comparative Example 3 in which carboxymethyl chitosan was replaced with hyaluronic acid, sufficient antibacterial properties were not obtained, probably because N-lauroyl-L-arginine ethyl ester acetate interacts with sodium hyaluronate.

As described above, all of the examples of the present invention show good transparency, high moisturizing property and skin affinity, little skin irritation, and antibacterial properties. Was enough. On the other hand, in Comparative Examples not containing either the N-long-chain acyl basic amino acid derivative or any of its salts and chitosans, decreased moisturizing properties and skin affinity were observed, and sufficient antibacterial properties were not obtained. . Increasing the amount of the antibacterial agent, methyl parahydroxybenzoate, provided antibacterial properties but increased skin irritation. When sodium hyaluronate having an anion was added without using chitosans, a decrease in transparency and the like were observed.

Subsequently, the appearance and the like of Examples 4 to 6 of the present invention were evaluated in the same manner as described above, and the viscosity was also evaluated. At this time, the comparative examples shown in Table 7 were also evaluated at the same time.

[Table 7]

(1) Appearance and Viscosity Regarding the viscosity, it was evaluated whether each of the examples and comparative examples had a viscosity suitable for use, and the time-dependent change in viscosity when stored at 25 ° C. for 3 months was observed. did. The results are shown in Table 8. Table 8
Regarding the medium and viscosity, the case where moderate viscosity was exhibited was represented by ○, and the case where the viscosity was too high or too low and the usability was poor was represented by x. In addition, 場合 indicates that the change in viscosity with time was hardly observed, △ indicates that a slight change in viscosity was observed, and X indicates that the change in viscosity was large.

[0028]

[Table 8] Table 8 shows that Examples 4 to 6 of the present invention all show good transparency, have an appropriate viscosity, and have little change in viscosity over time. On the other hand, in Comparative Example 6 in which chitosans were replaced with carboxyvinyl polymers, good transparency was not obtained, sufficient thickening was not observed, and the time-dependent change in viscosity was large.

(2) Moisturizing property, skin affinity and skin irritation
Table 9 shows the evaluation results. Table 9 shows that the examples of the present invention all have high moisturizing properties and skin affinity, and have little skin irritation. In contrast, N-
In Comparative Examples containing only one of an acid addition salt of a long-chain acyl-basic amino acid derivative and chitosans, high moisturizing properties and skin affinity as in Examples were not observed, and paraoxybenzoic acid was not observed. In Comparative Example 4b and Comparative Example 5 containing methyl, the skin irritation increased as the amount of methyl paraoxybenzoate increased.

[Table 9]

(3) Antibacterial properties Table 10 shows the test results of the antibacterial properties. In Examples 4 to 6 of the present invention, sufficient antibacterial properties against all bacteria and fungi were recognized. In contrast, Comparative Example 4a and Comparative Example 6 containing only one of the acid addition salt of N-long-chain acyl basic amino acid derivative and chitosans did not show sufficient antibacterial activity, and methyl paraoxybenzoate was used. Even if added, 0.05% by weight
Did not provide sufficient antibacterial properties.

[Table 10]

Next, the formulation of another embodiment of the present invention will be described.

[Example 7] Softening lotion (1) Sorbitol 4.00 (% by weight) (2) N-stearoyl-L-lysine butyl ester lactate 0.05 (3) Hydroxypropyl chitosan 0.30 (4 ) Ethanol 5.00 (5) Fragrance 0.10 (6) Purified water 90.55 Production method: (1) to (5) are sequentially added to (6) and uniformly dissolved.

Example 8 Astringent Lotion (1) N-palmitoyl-L-histidine benzyl ester 0.10 (% by weight) hydrochloride (2) Deacetylated chitin (Deacetylation degree: 45%) 05 (3) N-glucosyl chitosan 0.05 (4) N-lactosyl chitosan 0.05 (5) Aluminum chloride 0.05 (6) Ethanol 5.00 (7) Fragrance 0.15 (8) Purified water 94 .55 Production method: (1) to (7) are sequentially added to (8) and uniformly dissolved.

Example 9 Washing lotion (1) 1,3-butylene glycol 3.00 (% by weight) (2) N-myristoyl-L-histidine ethyl ester 0.10 DL-pyrrolidone carboxylate (3 ) N-Eicosanoyl-L-histidine ethyl ester 0.10 DL-pyrrolidone carboxylate (4) N-oleoyl-L-arginine ethyl ester 0.10 Hydrochloride (5) Chitosan (average molecular weight 500,000) 0.01 (6) Citric acid 0.50 (7) Fragrance 0.10 (8) Purified water 96.09 Production method: (1) to (7) are sequentially added to (8) and uniformly dissolved.

Example 10 Two-layer lotion (1) Squalane 8.000 (% by weight) (2) Blue No. 403 0.001 (3) N-cocoyl-L-lysine propyl ester acetate 0.200 (4) Glycerin 2.000 (5) Hydroxyethyl chitosan 0.500 (6) Ethanol 6.000 (7) Fragrance 0.150 (8) Purified water 83.149 Production method: Dissolve (2) in (1) Oil phase. On the other hand (3)-(7)
Are sequentially added to (8) and dissolved to form an aqueous phase. The oil phase is added to the aqueous phase at room temperature, and the mixture is stirred and filtered.

Example 11 Hair Restoration Lotion (1) Ethanol 15.00 (% by weight) (2) N-cocoyl-L-histidine methyl ester 0.10 DL-pyrrolidone carboxylate (3) Hydroxypropyl chitosan 60 (4) Hinokitiol 0.01 (5) Assembly extract 5.00 (6) Vitamin B ₆ 0.20 (7) Tocopherol acetate 0.50 (8) Fragrance 0.20 (9) Purified water 78.39 Production method : Dissolve (4) to (8) in (1), then add to (9) together with (2) and (3) and dissolve uniformly.

Examples 7 to 11 described above exhibited good transparency, were excellent in moisture retention and skin affinity, and had reduced skin irritation. In addition, it had a viscosity suitable for use, and had sufficient antibacterial properties.

[0038]

As described above in detail, it is possible to obtain a liquid cosmetic having good transparency, excellent moisturizing properties and skin affinity, low skin irritation and sufficient antibacterial activity according to the present invention. did it. Furthermore, in the liquid cosmetic according to the present invention, it was easy to impart a viscosity suitable for use.

Claims (2)

[Claims] 1. An N-long-chain acyl-basic amino acid derivative represented by the general formula (1), (2) or (3) and one or more acid addition salts thereof, and chitosan , A liquid cosmetic comprising one or more selected from chitosan derivatives and salts thereof. Embedded image Embedded image Embedded image (However, in the general formulas (1) to (3), RCO is a saturated or unsaturated fatty acid residue having 6 to 20 carbon atoms, X is —NH ₂ ,
_{-OCH 3, -OC 2 H 5,} -OC 3 H 7, -OC 4 H 9 or -OC
It represents H ₂ C ₆ H ₅ , and in the general formula (2), n represents 3 or 4. ) 2. The method according to claim 1, wherein one or more of N-long-chain acyl-basic amino acid derivatives and acid addition salts thereof, and one or more of chitosan, chitosan derivatives and salts thereof are liquid. 0.001-0.001 in the total amount of cosmetics
The liquid cosmetic according to claim 1, wherein the amount is 0.5% by weight and 0.001 to 10.0% by weight.