JP2005179239A - Skin care preparation - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To obtain a skin care preparation having the function as a substantial lightening cosmetic exerting bleaching effect while suppressing excessive melanogenesis and maintaining natural feeling. <P>SOLUTION: The skin care preparation is obtained by compounding 4-n-butylresorcinol and/or a salt thereof, an alkylenepolyamine derivative and/or a salt thereof, and as necessary, an antimicrobial polyhydric alcohol and a (co)polymer based on poly(meth)acrylic acid and introduced with hydrophilic groups onto the side chain. <P>COPYRIGHT: (C)2005,JPO&NCIPI

Description

  The present invention relates to a skin external preparation, and more particularly to a skin external preparation suitable for lightening cosmetics.

  Many people want to keep their skin white, but on the other hand, the skin white that has become strange or strange due to the development of various whitening cosmetics in recent years. Some people feel resistance, and whitening that is natural but feels natural is now desired. As a skin external preparation for such a purpose, a cosmetic field called “lightening cosmetic” has recently become common (see, for example, Patent Document 1, Patent Document 2, and Patent Document 3). However, although the concept of lightning cosmetics has been established, there was no effective ingredient responsible for the actual condition, so there was no choice but to say that there was no effective one. In order to achieve such an effect, it is said that it is necessary to have a moderate melanin production suppressing effect, an excellent skin conditioning effect, and an excellent moisturizing effect that are not excessive. It is not yet known about a combination of a raw material and a component that exhibits such an effect.

  As a “whitening agent” that suppresses melanin production, placenta extract, ellagic acid and its salt, ascorbic acid and its derivative, tranexamic acid and its salt, kojic acid and its salt, arbutin and its salt, 4- n-Butyl resorcinol and its salt have already been developed (for example, refer nonpatent literature 1).

  Regarding the alkylenepolyamine derivative and its salt, a technique for incorporating into an external preparation for skin as a rough skin improving agent is known (see, for example, Patent Document 4 and Patent Document 5).

Supervised by Takeda et al., “Advances and Future Prospects in Evaluation Technology for Cosmetics,” Yakuji Nippo Inc., March 31, 2001 JP 2003-31714 A JP 2000-502359 A Japanese Patent Laid-Open No. 08-486201 Japanese Patent Laid-Open No. 2002-212045 Japanese Patent Laid-Open No. 2002-30056

  The present invention has been made under the circumstances as described above, and has a function as a substantial lightening cosmetic that exerts a whitening effect while appropriately suppressing melanin production and maintaining a natural feeling. It is an object to provide an external preparation for skin.

In order to solve the above-mentioned problems, the present inventors have sought for an external preparation for skin having a function as a substantial lightening cosmetic, and as a result of earnest research, 4-n-butylresorcinol and / or a salt thereof have been obtained. And an external preparation for skin containing an alkylene polyamine derivative and / or a salt thereof have been found to have desired characteristics, and the present invention has been completed.
That is, the present invention relates to the following technique.

(1) A skin external preparation comprising 4-n-butylresorcinol and / or a salt thereof, and an alkylene polyamine derivative and / or a salt thereof.
(2) An alkylene polyamine derivative and / or a salt thereof is ethylenediamine-N, N′-diacetic acid, ethylenediamine-N, N, N′-3 acetic acid, ethylenediamine-N, N, N ′, N′-4 acetic acid, ethylenediamine -N, N'-dipropionic acid, ethylenediamine-N, N'-disuccinic acid, ethylenediamine-N, N'-diglutaric acid, trimethylenediamine-N, N'-diacetic acid, trimethylenediamine-N, N ' -Dipropionic acid, trimethylenediamine-N, N'-disuccinic acid, trimethylenediamine-N, N'-diglutaric acid, glutamic acid-N, N-diacetic acid, hydroxyethylethylenediamine-N, N, N'-3 Acetic acid, diethylenetriamine-N, N, N ′, N ″, N ″ -5 acetic acid, ethylenediamine-N, N-di (polyoxyethylene) -N ′, N′-di Reoxypropylene), ethylenediaminetetrakis (2-hydroxyisopropyl) -N, N′-dioleic acid, lauroylethylenediamine-N, N, N′-3 acetic acid, hydroxyethylethylenediamine-N, N, N ′, N′-4 The skin external preparation according to (1), which is one or more selected from acetic acid, cyclohexanediamine-N, N, N ′, N′-4 acetic acid and salts thereof.
(3) The skin external preparation according to (1) or (2), wherein the content of 4-n-butylresorcinol and / or a salt thereof is 0.1 to 10% by mass.
(4) Content of alkylene polyamine derivative and / or its salt is 0.01-5 mass%, The skin external preparation in any one of (1)-(3) characterized by the above-mentioned.
(5) The external preparation for skin according to any one of (1) to (4), further comprising an antibacterial polyhydric alcohol.
(6) Antibacterial polyhydric alcohol is 1,3-butanediol, isoprene glycol, 1,2-pentanediol, 1,2-hexanediol, 2-methyl-2,4-pentanediol, 1,2-heptane The external preparation for skin according to (5), which is one or more selected from diol and 1,2-octanediol.
(7) The method according to any one of (1) to (6), further comprising a polymer or copolymer having polyacrylic acid or polymethacrylic acid as a base and having a hydrophilic group introduced into a side chain. Skin external preparation.
(8) A polymer or copolymer containing polyacrylic acid or polymethacrylic acid as a base and having a hydrophilic group introduced in the side chain is polymethacryloyloxyethoxyphosphorylcholine, polyglucosylethoxymethacrylate, polymethacryloyloxyethoxyphosphorylcholine / butyl methacrylate The external preparation for skin according to (7), which is one or more selected from a copolymer and polymethacryloyl lysine.
(9) The skin external preparation according to any one of (1) to (8), which is a whitening cosmetic.
(10) The external preparation for skin according to (9), which is a lightning cosmetic.

  ADVANTAGE OF THE INVENTION According to this invention, the skin external preparation which has a function as a substantial lightening cosmetics which exhibits a whitening effect, suppressing a melanin production moderately and maintaining natural feeling can be provided.

<1> About 4-n-butylresorcinol and / or its salt which is an essential component of the skin external preparation of this invention The skin external preparation of this invention is 4-n-butylresorcinol and / or its salt (henceforth "4 -N-butylresorcinol etc. "). It is known that 4-n-butylresorcinol and the like are whitening components that suppress melanin production (see, for example, Non-Patent Document 1).

4-n-butylresorcinol can be prepared according to conventional methods, for example, Lille,
J .; Bitter, LA; Peiner, V. Trudy-Nauchono-Issledovatel 'skii Institut Slantsev (1969), No. 18, 127-34. That is, a method in which resorcin and butanoic acid are condensed in the presence of zinc chloride and reduced with zinc amalgam / hydrochloric acid, or a method in which resorcin and n-butyl alcohol are condensed at a high temperature of 200 to 400 ° C. can be exemplified.

  The 4-n-butylresorcinol thus obtained can be converted into a salt by reacting with various basic compounds. Such a salt is not particularly limited as long as it is physiologically acceptable, and examples thereof include alkali metal salts such as sodium salt and potassium salt, alkaline earth metal salts such as calcium salt and magnesium salt, Preferred examples include organic amine salts such as ammonium salt, triethanolamine salt and triethylamine salt, and basic amino acid salts such as lysine salt and arginine salt. Among these salts, alkali metal salts are particularly preferable, and sodium salts are particularly preferable.

  In the external preparation for skin of the present invention, 4-n-butylresorcinol and the like can be contained alone or in combination of two or more.

  The preferred content of 4-n-butylresorcinol and the like in the external preparation for skin of the present invention is 0.1 to 10% by mass and 0.1 to 0.5% by mass with respect to the total amount of external preparation for skin. % Is more preferable. This is because if the amount is too small, the effect may not be exhibited, and if the amount is too large, the effect may reach its peak.

<2> Alkylene polyamine derivative and / or salt thereof, which is an essential component of the skin external preparation of the present invention The skin external preparation of the present invention contains an alkylene polyamine derivative and / or a salt thereof. Here, the “alkylene polyamine derivative” is a general term for a compound having a structure in which at least two hydrogen atoms of an alkane are substituted with an amino group or a derivative thereof, and if desired, a hydroxyl group, a carbonyl group or a carboxyl group in the molecule. Can also be included.

  The alkylene polyamine derivative preferably has 2 to 14 carbon atoms, and more preferably 2 to 6 carbon atoms. For example, ethylenediamine, trimethylenediamine, glutamic acid, hydroxyethylethylenediamine, diethylenetriamine, ethylenediamine-N, N-di (polyoxyethylene) -N ′, N′-di (polyoxypropylene), ethylenediaminetetrakis (2-hydroxyisopropyl) , Lauroylethylenediamine, cyclohexanediamine, 2-hydroxytrimethylenediamine and the like.

  The alkylene polyamine derivative is preferably in the form of a “complex” in which an organic acid is bonded to the alkylene polyamine derivative as described above. Such a complex is a complex of an amine in the molecule of an alkylene polyamine derivative and an organic acid. Some or all of them can be present in the form of salts with organic acids.

  Preferred examples of the organic acid forming the complex as described above include monobasic acids such as acetic acid, propionic acid, lauric acid, and oleic acid, and dibasic acids such as succinic acid and glutaric acid.

Examples of the complex of the alkylene polyamine derivative and the organic acid include ethylenediamine-N, N′-diacetic acid, ethylenediamine-N, N, N′-3 acetic acid, ethylenediamine-N, N, N ′, N′-4 acetic acid, Ethylenediamine-N, N′-dipropionic acid, ethylenediamine-N, N′-disuccinic acid, ethylenediamine-N, N′-diglutaric acid, trimethylenediamine-N, N′-diacetic acid, trimethylenediamine-N, N '-Dipropionic acid, trimethylenediamine-N, N'-disuccinic acid, trimethylenediamine-N, N'-diglutaric acid, glutamic acid-N, N-diacetic acid, hydroxyethylethylenediamine-N, N, N'- 3 acetic acid, diethylenetriamine-N, N, N ′, N ″, N ″ -5 acetic acid, ethylenediaminetetrakis (2-hydroxyisopropyl) -N N′-dioleic acid, lauroylethylenediamine-N, N, N′-3 acetic acid, hydroxyethylethylenediamine-N, N, N ′, N′-4 acetic acid, cyclohexanediamine-N, N, N ′, N′-4 Acetic acid, 2-hydroxytrimethylenediamine-N, N′-diacetic acid, 2-hydroxytrimethylenediamine-N, N′-dipropionic acid, 2-hydroxytrimethylenediamine-N, N′-disuccinic acid, 2- Hydroxytrimethylenediamine-N, N′-diglutaric acid, ethylenediamine-N-acetic acid-N′-succinic acid, ethylenediamine-N-acetic acid-N′-propionic acid, ethylenediamine-N-propionic acid-N′-succinic acid, Ethylenediamine-N-acetic acid-N'-glutaric acid, trimethylenediamine-N-acetic acid-N'-succinic acid, trimethylenediamine-N-vinegar -N'-propionic acid, trimethylenediamine-N-propionic acid-N'-succinic acid, trimethylenediamine-N-succinic acid-N'-glutaric acid, 2-hydroxytrimethylene-N-acetic acid-N'- Preferred examples include succinic acid, 2-hydroxytrimethylenediamine-N-acetic acid-N′-propionic acid, 2-hydroxytrimethylenediamine-N-acetic acid-N′-succinic acid, and the like.

  In addition, the alkylene polyamine derivative is preferably a form in which polyoxyalkylene is bonded to the alkylene polyamine derivative. Such a form includes ethylenediamine-N, N-di (polyoxyethylene) -N ′, N′-di. (Polyoxypropylene) and the like can be suitably exemplified. The polyoxyalkylene preferably has a polymerization degree of 2 to 10.

  Among the above-mentioned alkylene polyamine derivatives, ethylenediamine-N, N′-diacetic acid, ethylenediamine-N, N, N′-3 acetic acid, ethylenediamine-N, N, N ′, N′-4 acetic acid, ethylenediamine-N, N '-Dipropionic acid, ethylenediamine-N, N'-disuccinic acid, ethylenediamine-N, N'-diglutaric acid, trimethylenediamine-N, N'-diacetic acid, trimethylenediamine-N, N'-dipropionic acid , Trimethylenediamine-N, N'-disuccinic acid, trimethylenediamine-N, N'-diglutaric acid, glutamic acid-N, N-diacetic acid, hydroxyethylethylenediamine-N, N, N'-3acetic acid, diethylenetriamine- N, N, N ′, N ″, N ″ -5 acetic acid, ethylenediamine-N, N-di (polyoxyethylene)- ', N'-di (polyoxypropylene), ethylenediaminetetrakis (2-hydroxyisopropyl) -N, N'-dioleic acid, lauroylethylenediamine-N, N, N'-3acetic acid, hydroxyethylethylenediamine-N, N, N ', N'-4 acetic acid, cyclohexanediamine-N, N, N', N'-4 acetic acid can be exemplified more preferably.

  Such derivatives can be made into salts by further adding a base. Examples of such salts include alkali metal salts such as sodium salt and potassium salt, alkaline earth metal salts such as calcium salt and magnesium salt, organic amine salts such as ammonium salt, triethanolamine salt and triethylamine salt, lysine salt, Preferred examples include basic amino acid salts such as arginine salts. Particularly preferred as salts of such alkylene polyamine derivatives are trisodium ethylenediamine-N, N'-disuccinate and tetrasodium glutamate-N, N-diacetate.

Such an alkylene polyamine derivative and / or a salt thereof can be produced according to a known method, for example, by reacting a diamine with a halide or an olefin compound. Here, as the diamine, for example, ethylenediamine, propylenediamine, trimethylenediamine, hexamethylenediamine, 2-hydroxytrimethylenediamine, diethylenetriamine and the like, as the halide, for example, chloroacetic acid, bromoacetic acid, sodium chloroacetate, Sodium bromoacetate, sodium chloropropionate, sodium bromopropionate, 2-chloroethanol, 3-chloropropanol and the like, and examples of olefin compounds include maleic acid, fumaric acid, methyl maleate, methyl fumarate, maleate. Examples include ethyl acrylate, ethyl fumarate, methyl acrylate, ethyl acrylate, acrylonitrile, and propyl fumarate.

  The alkylene polyamine derivative and / or its salt can also be produced by a method of reacting dihalide or the like with ammonia or the like. Here, examples of the dihalide include dichloroethane, dibromoethane, dichloropropane, dichlorobutane, and dibromobutane.

  Alkylene polyamine derivatives and / or salts thereof can be produced and used according to known methods as described above, but many of these are already commercially available, and such commercial products can be purchased and used. . In particular, trisodium ethylenediamine-N, N'-disuccinate and tetrasodium glutamate-N, N-diacetic acid are general-purpose raw materials for cosmetics and are suitable for use.

  In the skin external preparation of the present invention, the alkylene polyamine derivative and / or salt thereof may be used alone or in combination of two or more.

  In the external preparation for skin of the present invention, such an alkylenepolyamine derivative and / or a salt thereof works together with 4-n-butylresorcinol and the like, and is not excessive and has an appropriate melanin production inhibitory effect and an excellent skin conditioning effect. It is applied to an external preparation and has the effect of acting as a skin external preparation having a function as a substantial lightening cosmetic. In order to achieve such an effect, the skin external preparation contains one or more selected from alkylenepolyamine derivatives and salts thereof in a total amount of 0.01 to 5 mass with respect to the total amount of the skin external preparation. %, Preferably 0.05 to 1% by mass.

<3> About the external preparation for skin of the present invention The external preparation for skin of the present invention contains 4-n-butylresorcinol and the like, an alkylene polyamine derivative and / or a salt thereof, which are the essential components.

  The skin external preparation of the present invention, by adopting such a configuration, imparts a moderate melanin production inhibitory effect and an excellent skin conditioning effect to the skin external preparation, not excessive, and functions as a substantial lightening cosmetic. It has the characteristics of making it an external preparation for skin. Therefore, the skin external preparation of the present invention is particularly preferably used as a cosmetic having a lightening effect among whitening cosmetics.

  Moreover, the external preparation for skin as used in the present invention refers to all preparations for external use on the skin, and includes cosmetics, external preparations for skin, miscellaneous items for external use. Particularly preferred among the external preparations for skin of the present invention are cosmetics (including quasi drugs). In particular, from the above viewpoint, it is preferable to apply as a lightening cosmetic among whitening cosmetics.

In the external preparation for skin of the present invention, in addition to the above essential components, optional components that are usually used in external preparations for skin can be contained. Such optional components include, for example, hydrocarbons such as petrolatum, squalane, liquid paraffin, light liquid isoparaffin, heavy liquid isoparaffin, microcrystalline wax, solid paraffin,
Silicones such as dimethicone, femethicone, cyclomethicone, amodimethicone, polyether-modified silicone, jojoba oil, carnauba wax, molasses, beeswax, gallow, octyldodecyl oleate, isopropyl myristate, neopentyl glycol diisostearate, apple Esters such as diisostearyl acid, fatty acids such as stearic acid, lauric acid, myristic acid, palmitic acid, isostearic acid, isopalmitic acid, behenic acid, oleic acid,
Higher alcohols such as behenyl alcohol, cetanol, oleyl alcohol, and octadecyl alcohol; alkyl (alkenyl) glyceryl ethers such as batyl alcohol and ceralkyl alcohol;
Castor oil, coconut oil, hydrogenated coconut oil, coconut oil, wheat germ oil, triglycerides such as isostearic acid triglyceride, isooctanoic acid triglyceride, olive oil, glycerin, diglycerin, dipropylene glycol, polyethylene glycol, 1,3-butanediol Polyhydric alcohols such as isoprene glycol, 1,2-pentanediol, 1,2-hexanediol, 2-methyl-2,4-pentanediol, 1,2-heptanediol, 1,2-octanediol,
Glyceryl monostearate, glyceryl monooleate, diglyceryl monostearate, diglyceryl monooleate, sorbitan sesquioleate, sorbitan monooleate, sorbitan trioleate, sorbitan sesquistearate, sorbitan monostearate, polyoxyethylene (POE) sorbitan mono Olate, polyoxyethylene sorbitan sesquioleate, polyoxyethylene sorbitan monostearate, polyoxyethylene stearate, polyoxyethylene oleate, polyoxyethylene glycerin fatty acid ester, polyoxyethylene alkyl ether, polyoxyethylene hydrogenated castor oil, sucrose Nonionic surfactants such as sucrose fatty acid esters such as monolaurate and sucrose monostearate, Um lauryl stearate, polyoxyethylene alkyl sulfates, anionic surfactants such as sulfosuccinic acid ester salts, cationic surfactants such as quaternary alkyl ammonium salts, amphoteric surfactants such as alkyl betaines,
Organic powders such as crystalline cellulose, cross-linked methylpolysiloxane, polyethylene powder, acrylic resin powder, talc, mica, sericite, magnesium carbonate, calcium carbonate, titanium dioxide, iron oxide, bitumen, ultramarine, titanium mica, titanium Powders that may be surface-treated such as sericite and silica,
Polymethacrylic acid or polymethacrylic acid, such as polymethacryloyloxyethoxyphosphorylcholine, polyglucosylethoxymethacrylate, polymethacryloyloxyethoxyphosphorylcholine / butyl methacrylate copolymer, polymethacryloyllysine, etc., with hydrophilic groups introduced in the side chain Polymers or copolymers, moisturizing ingredients such as sodium pyrrolidonecarboxylate, lactic acid, sodium lactate,
Acrylic acid-alkyl methacrylate copolymers and / or salts thereof, carboxyvinyl polymers and / or salts thereof, thickeners such as xanthan gum and hydroxypropyl cellulose,
Alkaline agents such as potassium hydroxide and sodium hydroxide, vitamins such as retinol, retinoic acid, tocopherol, riboflavin, pyridoxine, and terpenes such as glycyrrhizinate, glycyrrhetinic acid, ursolic acid, oleanolic acid,
Preferred examples include active ingredients such as steroids such as estradiol, ethinyl estradiol, and estriol.

  In addition, as long as the effect by the combination of 4-n-butylresorcinol and / or its salt and an alkylene polyamine derivative and / or its salt is not impaired, the skin external preparation of this invention is whitening other than 4-n-butylresorcinol. Ingredients may be included.

Among the above components, the following are particularly preferred: 1,3-butanediol, isoprene glycol, 1,2-pentanediol, 1,2-hexanediol, 2-methyl-2,4-pentanediol, Antibacterial polyhydric alcohols such as 1,2-heptanediol and 1,2-octanediol. Secondly, polymethacryloyloxyethoxyphosphorylcholine, polyglucosylethoxymethacrylate ester, polymethacryloyloxyethoxyphosphorylcholine / butyl methacrylate copolymer ( Polyquaternium 51), polymethacryloyloxyethoxyphosphorylcholine / stearyl methacrylate copolymer (polyquaternium 61), polyacrylic acid such as polymethacryloyl lysine or polymethacrylic acid as a base, and a hydrophilic group in the side chain It is introduced polymer or copolymer.

  In the present invention, the term “antibacterial” means including antimicrobial in a narrow sense and bacteriostatic (bacteriostatic or fungistatic), and has a bactericidal action or an action of suppressing the growth of microorganisms. The polyhydric alcohol is “antibacterial” as referred to in the present invention. The antibacterial polyhydric alcohol is not particularly limited as long as the effect of the present invention is not impaired. Specifically, for example, linear alkyl diols having a relatively long carbon chain such as the polyhydric alcohols exemplified above are used. Any of these can be used in the external preparation for skin of the present invention. As the content, 1-10 mass% is preferable with respect to the skin external preparation whole quantity by the total amount. By containing such ingredients, it can be formulated without using preservatives such as parabens that can induce irritation to the skin, thereby smoothing the skin and enhancing the lightening effect Can do.

  As a polymer or copolymer having polyacrylic acid or polymethacrylic acid as a base and having a hydrophilic group introduced in the side chain, a polyacrylic acid structure may be used as the base, but those having a polymethacrylic acid structure as the base are preferred. Examples of the hydrophilic group include a sugar residue, an amino acid residue, and a group having a phosphoryl group. Such a polymer or copolymer may be obtained by reacting an acetylated or brominated sugar with acrylic acid or methacrylic acid, if desired, and reacting with an acetylated or brominated sugar, such as thionyl chloride. (Meth) acrylic acid derivatives obtained by inducing acid chlorides and condensing with amino acids, (meth) acrylic acid derivatives obtained by esterifying chloroalcohol with acrylic acid or methacrylic acid and condensing with amino acids or phosphorylcholine, etc. Can be obtained by polymerizing by solution polymerization or the like. Moreover, since there exists a commercial item in any of these, this commercial item can also be purchased and used. The preferable content of the polymer or copolymer having such a polyacrylic acid or polymethacrylic acid as a base and having a hydrophilic group introduced in the side chain is 0.01 to 5% by mass in total with respect to the total amount of the external preparation for skin. . Such a component has an effect of imparting an excellent moisturizing effect to the external preparation for skin, improving the moisture content of the skin surface, and thereby exerting the lightening effect more remarkably.

The skin external preparation of this invention can be manufactured by processing the above-mentioned essential component and an arbitrary component according to a conventional method.
As the dosage form of the external preparation for skin of the present invention, any dosage form known as an external preparation for skin can be applied without any particular limitation. For example, lotions, essences, emulsions, creams, gels and the like are preferably exemplified. it can. In particular, as a lightening cosmetic, there is a case where it is applied to a topical area that is dull and loses its shine, and therefore, a spot essence dosage form can be preferably exemplified.

  Hereinafter, the present invention will be described more specifically with reference to examples, but it goes without saying that the present invention is not limited to such examples.

<Example 1>
In accordance with the formulation shown below, an emulsification type high viscosity essence 1 (cosmetic) which is an external preparation for skin of the present invention was prepared.
That is, prescription components a), b) and c) are each heated to 70 ° C., neutralized by adding b) to a), and gradually added to c) and emulsified, and the emulsified particles are prepared with a homogenizer. Then, the mixture was cooled with stirring to obtain Spots type essence 1.

B)
Acrylic acid-alkyl methacrylate (alkyl group having 10 to 30 carbon atoms) copolymer (trade name “Pemlen TR-2”, manufactured by Goodrich) (hereinafter referred to as “acrylic acid-alkyl methacrylate copolymer”)
0.2 parts by mass carboxyvinyl polymer 0.2 parts by mass 1,3-butanediol 5 parts by mass 1,2-hexanediol 2 parts by mass polyethylene glycol 6000 2 parts by mass ethylenediamine-N, N′-disuccinate trisodium 1 part by weight polymethacryloyloxyethoxyphosphorylcholine 0.1 part by weight 4-n-butylresorcinol 0.3 part by weight POE (20) sorbitan sesquiolate 0.5 part by weight water 30 parts by weight b)
Potassium hydroxide 10 mass% aqueous solution 3 mass parts water 49.5 mass parts c)
Seralkyl alcohol 1.5 parts by mass Glyceryl monostearate 0.5 parts by mass Sucrose monolaurate 0.1 parts by mass Vaseline 5 parts by mass

<Example 2>
In the same manner as in Example 1, emulsification type high-viscosity essence 2 (cosmetics) was produced according to the formulation shown below.

B)
Acrylic acid-alkyl methacrylate copolymer 0.2 parts by mass Carboxyvinyl polymer 0.2 parts by mass 1,3-butanediol 5 parts by mass 1,2-hexanediol 2 parts by mass Polyethylene glycol 6000 2 parts by mass Ethylenediamine-N, N ′ -Trisodium disuccinate 0.1 parts by weight polymethacryloyloxyethoxyphosphorylcholine 0.1 parts by weight 4-n-butylresorcinol 5 parts by weight POE (20) sorbitan sesquiolate 0.5 parts by weight water 30 parts by weight b)
Potassium hydroxide 10 mass% aqueous solution 3 parts by mass water 44.8 parts by mass c)
Seralkyl alcohol 1.5 parts by mass Glyceryl monostearate 0.5 parts by mass Sucrose monolaurate 0.1 parts by mass Vaseline 5 parts by mass

<Example 3>
In the same manner as in Example 1, an emulsification type high-viscosity essence 3 (cosmetics) was produced according to the formulation shown below.

B)
Acrylic acid-alkyl methacrylate copolymer 0.2 parts by mass Carboxyvinyl polymer 0.2 parts by mass 1,3-butanediol 5 parts by mass 1,2-hexanediol 2 parts by mass Polyethylene glycol 6000 2 parts by mass Ethylenediamine-N, N ′ -Trisodium disuccinate 0.1 parts by weight polymethacryloyloxyethoxyphosphorylcholine 0.1 parts by weight 4-n-butylresorcinol 8 parts by weight POE (20) sorbitan sesquiolate 0.5 parts by weight water 30 parts by weight b)
Potassium hydroxide 10 mass% aqueous solution 3 parts by mass water 41.8 parts by mass c)
Seralkyl alcohol 1.5 parts by mass Glyceryl monostearate 0.5 parts by mass Sucrose monolaurate 0.1 parts by mass Vaseline 5 parts by mass

<Test Example 1>
About the essences 1-3 of the said Examples 1-3, the melanin production inhibitory effect was examined using the melanoma B-16 cell (available from the Tomita laboratory of Tohoku University medical school). As Comparative Examples 1 to 3, in which Ethylenediamine-N, N′-disuccinate trisodium of essences 1 to 3 was replaced with water, and in Comparative Example 4, 4-n-butylresorcinol of Essence 1 was replaced with water. A thing was used.

50 μl of MEM (modified eagle medium) supplemented with 15% FBS (fetal calf serum) is added to each well of the microtiter plate, seeded with melanoma B-16 cells at a dose of 5 × 10 ⁵ cells / ml, and 10 μl of specimen is added. And cultured for 48 hours. Cells were collected by centrifugation, washed twice with PBS (phosphate buffered saline), and the color of the cells was determined using the score. The determination was carried out using a sample cultured without adding a sample, score 0: same as control, score 1: slightly thinner than control, score 2: clearly thinner than control, score 3: almost white cells, score 4 : Judgment was made on the basis of white cells. The results are shown in Table 1. From this, it can be seen that, in the cosmetics of the present invention (essences 1 to 3), even when the concentration of 4-n-butylresorcinol increases, the inhibitory action on melanin production is almost constant. That is, in the skin external preparation of this invention, it turns out that the expression of excessive melanin production suppression is controlled. From this, it turns out that the skin external preparation of this invention is suitable as a lightening cosmetics.

<Example 4>
In the same manner as in Example 1, an emulsified high-viscosity essence 4 (cosmetic) was produced according to the following formulation.

B)
Acrylic acid-alkyl methacrylate copolymer 0.2 parts by mass Carboxyvinyl polymer 0.2 parts by mass 1,3-butanediol 5 parts by mass 1,2-hexanediol 2 parts by mass Polyethylene glycol 6000 2 parts by mass Glutamic acid-N, N- Tetrasodium diacetate 0.1 parts by mass polymethacryloyloxyethoxyphosphorylcholine 0.1 parts by mass 4-n-butylresorcinol 0.3 parts by mass POE (20) sorbitan sesquiolate 0.5 parts by weight water 30 parts by mass b)
Potassium hydroxide 10 mass% aqueous solution 3 mass parts water 49.5 mass parts c)
Seralkyl alcohol 1.5 parts by mass Glyceryl monostearate 0.5 parts by mass Sucrose monolaurate 0.1 parts by mass Vaseline 5 parts by mass

<Example 5>
In the same manner as in Example 1, emulsification type high viscosity essence 5 (cosmetics) was produced according to the following formulation.

B)
Acrylic acid-alkyl methacrylate copolymer 0.2 parts by mass Carboxyvinyl polymer 0.2 parts by mass 1,3-butanediol 5 parts by mass 1,2-hexanediol 2 parts by mass Polyethylene glycol 6000 2 parts by mass Glutamic acid-N, N- Tetrasodium diacetate 0.1 parts by mass polymethacryloyloxyethoxyphosphorylcholine 0.1 parts by mass 4-n-butylresorcinol 5 parts by mass POE (20) sorbitan sesquiolate 0.5 parts by weight water 30 parts by mass b)
Potassium hydroxide 10 mass% aqueous solution 3 parts by mass water 44.8 parts by mass c)
Seralkyl alcohol 1.5 parts by mass Glyceryl monostearate 0.5 parts by mass Sucrose monolaurate 0.1 parts by mass Vaseline 5 parts by mass

<Example 6>
In the same manner as in Example 1, an emulsified type high-viscosity essence 6 (cosmetic) was produced according to the following formulation.

B)
Acrylic acid-alkyl methacrylate copolymer 0.2 parts by mass Carboxyvinyl polymer 0.2 parts by mass 1,3-butanediol 5 parts by mass 1,2-hexanediol 2 parts by mass Polyethylene glycol 6000 2 parts by mass Glutamic acid-N, N- Tetrasodium diacetate 0.1 parts by mass polymethacryloyloxyethoxyphosphorylcholine 0.1 parts by mass 4-n-butylresorcinol 8 parts by mass POE (20) sorbitan sesquiolate 0.5 parts by weight water 30 parts by mass b)
Potassium hydroxide 10 mass% aqueous solution 3 parts by mass water 41.8 parts by mass c)
Seralkyl alcohol 1.5 parts by mass Glyceryl monostearate 0.5 parts by mass Sucrose monolaurate 0.1 parts by mass Vaseline 5 parts by mass

<Test Example 2>
In the same manner as in Test Example 1, essences 4 to 6 were evaluated. As Comparative Examples 5-7, the essence 4-6 glutamic acid-N, N-diacetate tetrasodium was replaced with water, and as Comparative Example 8, 4-n-butylresorcinol essence 4 was replaced with water. Was used. The results are shown in Table 2. In the cosmetics of this invention, even if the density | concentration of 4-n-butyl resorcinol increases, it turns out that the melanin production inhibitory effect is substantially constant. That is, in the skin external preparation of this invention, it turns out that the expression of excessive melanin production suppression is controlled. From this, it turns out that the skin external preparation of this invention is suitable as a lightening cosmetics.

<Examples 7 to 25>
Essence of Examples 7 to 25 in the same manner as in Example 1, except that ethylenediamine-N, N′-disuccinate trisodium in Essence 1 of Example 1 was replaced with each alkylene polyamine derivative or salt thereof shown in Table 3. 7-25 were produced. About these, the effect | action with respect to melanoma B-16 cell was investigated like the test example 1. FIG. The results are shown in Table 3. Considering the results shown in Table 4 below, it can be seen that other alkylenepolyamine derivatives or salts thereof have the same action as that of ethylenediamine-N, N′-disuccinate trisodium.

B)
Acrylic acid-alkyl methacrylate copolymer 0.2 parts by mass Carboxyvinyl polymer 0.2 parts by mass 1,3-butanediol 5 parts by mass 1,2-hexanediol 2 parts by mass polyethylene glycol 6000 2 parts by mass Alkylene polyamine according to Table 3 Derivatives or salts thereof 0.1 parts by mass polymethacryloyloxyethoxyphosphorylcholine 0.1 parts by mass 4-n-butylresorcinol 0.3 parts by mass POE (20) sorbitan sesquiolate 0.5 parts by weight water 30 parts by mass b)
Potassium hydroxide 10 mass% aqueous solution 3 mass parts water 49.5 mass parts c)
Seralkyl alcohol 1.5 parts by mass Glyceryl monostearate 0.5 parts by mass Sucrose monolaurate 0.1 parts by mass Vaseline 5 parts by mass

<Examples 26 to 44>
Essence 26 of Examples 26 to 44 was replaced by replacing each of the ethylenediamine-N, N′-disuccinate trisodium salt of Essence 2 of Example 2 with each of the alkylene polyamine derivatives shown in Table 4 or salts thereof. -44 were made. About these, the effect | action with respect to melanoma B-16 cell was investigated like the test example 1. FIG. The results are shown in Table 4. Considering the results in Table 3 above, it can be seen that other alkylene polyamine derivatives or salts thereof have the same action as that of ethylenediamine-N, N′-disuccinate trisodium.

B)
Acrylic acid-alkyl methacrylate copolymer 0.2 parts by mass Carboxyvinyl polymer 0.2 parts by mass 1,3-butanediol 5 parts by mass 1,2-hexanediol 2 parts by mass polyethylene glycol 6000 2 parts by mass Alkylene polyamine according to Table 3 Derivatives or salts thereof 0.1 parts by mass polymethacryloyloxyethoxyphosphorylcholine 0.1 parts by mass 4-n-butylresorcinol 5 parts by mass POE (20) sorbitan sesquiolate 0.5 parts by weight water 30 parts by mass b)
Potassium hydroxide 10 mass% aqueous solution 3 parts by mass water 44.8 parts by mass c)
Seralkyl alcohol 1.5 parts by mass Glyceryl monostearate 0.5 parts by mass Sucrose monolaurate 0.1 parts by mass Vaseline 5 parts by mass

<Example 45>
In the same manner as in Example 1, an essence was produced according to the formulation shown below. This was score 2 in the evaluation by the method of Test Example 1.

B)
Acrylic acid-alkyl methacrylate copolymer 0.2 parts by mass Carboxyvinyl polymer 0.2 parts by mass 1,3-butanediol 5 parts by mass 1,2-hexanediol 2 parts by mass Polyethylene glycol 6000 2 parts by mass Ethylenediamine-N, N ′ -Trisodium disuccinate 0.1 parts by mass polymethacryloyl lysine 0.1 parts by mass 4-n-butylresorcinol 8 parts by mass POE (20) sorbitan sesquiolate 0.5 parts by weight water 30 parts by mass b)
Potassium hydroxide 10 mass% aqueous solution 3 parts by mass water 41.8 parts by mass c)
Seralkyl alcohol 1.5 parts by mass Glyceryl monostearate 0.5 parts by mass Sucrose monolaurate 0.1 parts by mass Vaseline 5 parts by mass

<Example 46>
In the same manner as in Example 1, an essence was produced according to the formulation shown below. This was score 2 in the evaluation by the method of Test Example 1.

B)
Acrylic acid-alkyl methacrylate copolymer 0.2 parts by mass Carboxyvinyl polymer 0.2 parts by mass 1,3-butanediol 5 parts by mass 1,2-hexanediol 2 parts by mass Polyethylene glycol 6000 2 parts by mass Ethylenediamine-N, N ′ -Trisodium disuccinate 0.1 part by mass polyglucosylethoxy methacrylate 0.1 part by mass 4-n-butylresorcinol 8 parts by mass POE (20) sorbitan sesquiolate 0.5 parts by weight water 30 parts by mass b)
Potassium hydroxide 10 mass% aqueous solution 3 parts by mass water 41.8 parts by mass c)
Seralkyl alcohol 1.5 parts by mass Glyceryl monostearate 0.5 parts by mass Sucrose monolaurate 0.1 parts by mass

<Example 47>
In the same manner as in Example 1, an essence was produced according to the formulation shown below. This was score 2 in the evaluation by the method of Test Example 1.

B)
Acrylic acid-alkyl methacrylate copolymer 0.2 parts by mass Carboxyvinyl polymer 0.2 parts by mass 1,3-butanediol 5 parts by mass 1,2-hexanediol 2 parts by mass Polyethylene glycol 6000 2 parts by mass Ethylenediamine-N, N ′ -Trisodium disuccinate 0.1 parts by mass Polyquaternium 51 0.1 parts by mass 4-n-butylresorcinol 8 parts by mass POE (20) sorbitan sesquiolate 0.5 parts by weight water 30 parts by mass b)
Potassium hydroxide 10 mass% aqueous solution 3 parts by mass water 41.8 parts by mass c)
Seralkyl alcohol 1.5 parts by mass Glyceryl monostearate 0.5 parts by mass Sucrose monolaurate 0.1 parts by mass

  The present invention can be applied to skin external preparations such as lightning cosmetics.

Claims (10)

A skin external preparation comprising 4-n-butylresorcinol and / or a salt thereof and an alkylenepolyamine derivative and / or a salt thereof. An alkylene polyamine derivative and / or a salt thereof is ethylenediamine-N, N′-diacetic acid, ethylenediamine-N, N, N′-3 acetic acid, ethylenediamine-N, N, N ′, N′-4 acetic acid, ethylenediamine-N , N′-dipropionic acid, ethylenediamine-N, N′-disuccinic acid, ethylenediamine-N, N′-diglutaric acid, trimethylenediamine-N, N′-diacetic acid, trimethylenediamine-N, N′-di Propionic acid, trimethylenediamine-N, N′-disuccinic acid, trimethylenediamine-N, N′-diglutaric acid, glutamic acid-N, N-diacetic acid, hydroxyethylethylenediamine-N, N, N′-3 acetic acid, Diethylenetriamine-N, N, N ′, N ″, N ″ -5acetic acid, ethylenediamine-N, N-di (polyoxyethylene -N ', N'-di (polyoxypropylene), ethylenediaminetetrakis (2-hydroxyisopropyl) -N, N'-dioleic acid, lauroylethylenediamine-N, N, N'-3acetic acid, hydroxyethylethylenediamine-N, One or more selected from N, N ', N'-4 acetic acid, cyclohexanediamine-N, N, N', N'-4 acetic acid and salts thereof, The external preparation for skin according to 1. The skin external preparation according to claim 1 or 2, wherein the content of 4-n-butylresorcinol and / or a salt thereof is 0.1 to 10% by mass. Content of alkylene polyamine derivative and / or its salt is 0.01-5 mass%, The skin external preparation of any one of Claims 1-3 characterized by the above-mentioned. Furthermore, antibacterial polyhydric alcohol is contained, The skin external preparation of any one of Claims 1-4 characterized by the above-mentioned. Antibacterial polyhydric alcohols are 1,3-butanediol, isoprene glycol, 1,2-pentanediol, 1,2-hexanediol, 2-methyl-2,4-pentanediol, 1,2-heptanediol and 1 The external preparation for skin according to claim 5, which is one or more selected from 1,2-octanediol. Furthermore, the skin external preparation of any one of Claims 1-6 containing the polymer or copolymer which made polyacrylic acid or polymethacrylic acid a base | substrate, and introduce | transduced the hydrophilic group into the side chain. . Polymers or copolymers based on polyacrylic acid or polymethacrylic acid and having hydrophilic groups introduced in the side chains are polymethacryloyloxyethoxyphosphorylcholine, polyglucosylethoxymethacrylate, polymethacryloyloxyethoxyphosphorylcholine / butyl methacrylate copolymer and poly The external preparation for skin according to claim 7, wherein the external preparation is one or more selected from methacryloyl lysine. The skin external preparation according to any one of claims 1 to 8, which is a whitening cosmetic. The skin external preparation according to claim 9, which is a lightening cosmetic.