JP2002302469A - Neopentanoic acid alkyl polyglycol - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a new compound useful as a humectant and to provide a skin care preparation containing the new compound. SOLUTION: This neopentanoic acid alkyl polyglycol is represented by formula (1) (wherein, (m) is an integer of 2-7; and (n) is an integer of 2-3). The humectant is composed of the neopentanoic acid alkyl polyglycol represented by formula (1). The skin care preparation comprises the neopentanoic acid alkyl polyglycol represented by formula (1).

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention has a moisturizing effect,
A novel compound useful as a humectant in external preparations for skin such as cosmetics, alkyl neopentanate polyglycol, a moisturizer composed of the alkyl polypentanoate and a feel of use containing the alkyl neopentanate polyglycol, particularly adaptability to the skin, The present invention relates to an external preparation for skin that has excellent skin smoothness, has no sticky feeling, and has a long-lasting moisturizing effect.

[0002]

2. Description of the Related Art In order to maintain healthy skin, it is essential to retain moisture, and many skin external preparations for moisturizing have been developed. Research on humectants has been actively conducted,
Today, moisturizers such as organic acid salts, polyhydric alcohols, and water-soluble polymers are blended in skin external preparations.

However, conventional moisturizers do not have sufficient moisturizing effects, especially the sustainability of moisturizing effects, and when applied to the skin, they are repelled by sebum, making them less familiar to the skin and having a sticky feeling. For example, the use feeling is not sufficient, and the development of a new humectant has been desired.

[0004]

SUMMARY OF THE INVENTION The present invention has been made in view of the above circumstances, and an object of the present invention is to provide a novel compound useful as a humectant. Another object of the present invention is to provide a skin external preparation containing the novel compound.

[0005]

Means for Solving the Problems The present inventors have conducted intensive studies to solve the above-mentioned problems, and as a result, a novel alkyl polypentanoate has solved the above-mentioned problems. It has been found that the above problems can be solved by blending an alkyl polyglycol acid, and the present invention has been completed based on these findings.

That is, the present invention provides the following formula (1)

Embedded image (Wherein, m represents an integer of 2 to 7 and n represents an integer of 2 to 3).

The novel compound of formula (1) of the present invention, alkyl polypentane neopentanate, has an excellent moisturizing function, in particular, an excellent moisturizing function. Furthermore, it has good familiarity with the skin, and is excellent in use feel such as skin smoothness and stickiness. From the above, the novel compound of the formula (1) of the present invention, alkyl polypentanoate, is useful as a humectant.

In the present invention, ethyltriglycol neopentanate in which m is 3 and n is 2 in the formula (1) is preferred.

The present invention is also a humectant comprising the alkyl polyglycol neopentanate of the formula (1).

The alkyl polyglycol neopentanoate of the formula (1) of the present invention has an excellent moisturizing effect, especially a moisturizing effect with excellent durability. Furthermore, it has good familiarity with the skin and is excellent in use feel such as skin smoothness and stickiness. From these facts, the compound polyalkylene neopentanate of the formula (1) of the present invention is useful as a humectant having an excellent use feeling on the skin. A preferred alkyl polyglycol neopentanate as a humectant in the present invention is ethyl triglycol neopentanate in which m is 3 and n is 2 in formula (1).

The present invention is also an external preparation for skin containing the alkyl polypentane neopentanate of the formula (1).

The external preparation for skin containing the compound of the formula (1) alkylpolypentane glycol neopentanoate of the present invention has an excellent moisturizing effect, in particular, a long-lasting moisturizing effect, and is well adapted to the skin. Since it gives the skin an excellent use feel such as smoothness and stickiness, it can be applied to pharmaceuticals, quasi-drugs, cosmetics and the like.

In the external preparation for skin of the present invention, in formula (1), ethyltriglycol neopentanoate wherein m is 3 and n is 2 is preferred.

In the skin external preparation containing the compound of formula (1) alkylpolypentane glycol of the present invention, it is preferable to further add a component having a moisturizing function, that is, a moisturizing agent. Preferred examples of the humectant include polyhydric alcohols, organic acid salts, mucopolysaccharides, plant extracts and the like, and one or more of these are blended.
Particularly preferred humectants are polyhydric alcohols.

In the skin external preparation of the present invention, a synergistic moisturizing effect can be exhibited by using a humectant in combination with the alkyl polyglycol neopentanoate of the present invention.
Furthermore, it is possible to improve the familiarity of the alkyl polyglycol neopentanate with the skin and the feeling of use of the smoothness of the skin.

[0016]

DESCRIPTION OF THE PREFERRED EMBODIMENTS Hereinafter, embodiments of the present invention will be described in detail.

The following formula (1) according to the present invention:

Embedded image Is a novel compound, which is newly provided by the present invention.

In the formula of the alkyl polyglycol neopentanate represented by the formula (1) according to the present invention, m is 2 to 7, and n is
Represents an integer of 2 to 3. When m and n are 1, there is a problem of skin irritation, and when m is 8 or more or n is 4 or more, when blended in an external preparation for skin, the feeling of use is impaired, which is not preferable. Desirable m is an integer of 2 to 4. Furthermore, m
Is an integer of 2 to 4, n is preferably 2, m is 3, and n is 2, and ethyl triglycol neopentanate is particularly preferable.

Specific examples of the alkyl polyglycol neopentanoate according to the present invention include ethyl diglycol neopentanate, ethyl triglycol neopentanoate, ethyl tetraglycol neopentanoate, ethyl pentaglycol neopentanoate, ethyl hexaglycol neopentanoate and neopentanoic acid. Ethyl heptaglycol,
Examples include propyl diglycol neopentanate, propyl triglycol neopentanate, propyl tetraglycol neopentanate, propyl pentaglycol neopentanate, propyl hexaglycol neopentanate, propyl heptaglycol neopentanate, and the like.

The alkyl polyglycol neopentanate according to the present invention can be produced, for example, by reacting neopentyl chloride with a catalyst of alkyl polyglycol in a solvent.

This reaction is generally promoted in the presence of an alkali catalyst. Examples of the alkali catalyst include sodium hydroxide, alkali hydroxides such as potassium hydroxide, ammonia,
Organic amines such as trimethylamine and triethylamine can be used. As the solvent, chloroform, methylene chloride, dichloroethane, dimethyl sulfoxide and the like are suitable. The reaction temperature is generally between 0 and 25
Although the reaction can be carried out at a temperature of about 70 ° C., the reaction is further promoted by heating to about 70 ° C.

From the reaction mixture thus obtained,
In order to isolate the target compound, silica gel column chromatography or vacuum distillation is generally used. The compound thus isolated is usually a colorless, odorless liquid. This compound can usually be identified by NMR or the like.

The compound of formula (1) of the present invention, alkyl polyglycol neopentanoate, has an excellent moisturizing function, in particular, an excellent moisturizing function. Further, when used on the skin, the skin is well-adapted to the skin, and is excellent in use feel such as smoothness and stickiness of the skin. From these facts, the compound polyalkylene neopentanate of the formula (1) of the present invention is useful as a humectant having an excellent feeling on skin. Alkyl neopentanoate polyglycol, which is particularly preferred as a humectant, is ethyl tripentanoate, and the above-described effects of alkyl polypentanoate can be particularly exhibited.

The alkyl polyglycol neopentanoate of the formula (1) of the present invention is blended with pharmaceuticals, quasi-drugs, cosmetics and the like, particularly for the purpose of imparting a moisturizing effect. In particular, use as a skin external preparation is preferable. The external preparation for skin containing the compound of formula (1) alkyl polyglycol neopentanoate of the present invention has an excellent moisturizing effect, especially a long-lasting moisturizing effect, and has good skin familiarity and smooth skin. Gives the skin an excellent feeling of use such as stickiness. When blending into a skin external preparation,
Particularly preferred is ethyltriglycol neopentanoate from the balance of production, safety, effects and the like.

The amount of the alkyl polyglycol neopentanoate to be added to the external preparation for skin varies depending on the dosage form and the like, but is usually 0.00% in the total amount of the external preparation for skin.
1-20 mass% is preferable. More preferably 0.01
To 10% by mass. Among various dosage forms, for example, in the case of an emulsified skin external preparation, the total amount of the skin external preparation is 0.001 to 0.001.
20% by mass is preferred. More preferably 0.1 to 10
% By mass. If the amount is less than 0.001% by mass, a sufficient effect by the compounding is not exhibited, and if the amount exceeds 20% by mass, the effect cannot be expected to increase. In addition, in the case of an aqueous skin external preparation such as a lotion, 0.001 to 2% by mass of the total amount of the skin external preparation
Is more preferable, and more preferably 0.01 to 1% by mass. If the amount is less than 0.001% by mass, the effect of the composition cannot be sufficiently exerted. Even if the amount exceeds 2% by mass, the effect cannot be expected to be increased, and a stable aqueous skin preparation for external use should be prepared. You will have a hard time.

The external preparation for skin of the present invention can exhibit a synergistic moisturizing effect by using a component having a moisturizing function, that is, a moisturizing agent, in combination with the alkylpolyglycol neopentanoate of the present invention. Furthermore, it is possible to improve the familiarity of the skin with the alkyl polyglycol neopentanate and the feeling of use of the smoothness of the skin.

As the humectant, any humectant that is generally added to the external preparation for skin can be used. For example, polyhydric alcohols, organic acid salts, mucopolysaccharides, plant extracts and the like can be mentioned. One or more of these humectants are selected and blended. Specific examples of preferred humectants include polyhydric alcohols such as ethylene glycol, trimethylene glycol, tetramethylene glycol, propylene glycol, dipropylene glycol,
1,3-butylene glycol, 1,2-butylene glycol, 2,3-butylene glycol, 1,2-pentanediol, pentamethylene glycol, 2-butene-
Dihydric alcohols such as 1,4-diol, hexylene glycol and octylene glycol; trihydric alcohols such as glycerin, trimethylolpropane and 1,2,6-hexanetriol; tetrahydric alcohols such as pentaerythritol; xylitol And pentahydric alcohols such as fructose; hexahydric alcohols such as sorbitol and mannitol; polyhydric alcohols such as amylolytic sugar-reducing alcohol; diethylene glycol, dipropylene glycol;
Triethylene glycol, polypropylene glycol,
Polyhydric alcohol polymers such as tetraethylene glycol, diglycerin, polyethylene glycol, triglycerin, tetraglycerin, and polyglycerin; POE-tetrahydrofurfuryl alcohol, POP-butyl ether, POP / POE-butyl ether, tripolyoxypropylene glycerin ether; POP-glycerin ether, POP / POE-diglycerin ether, P
Examples thereof include polyalkylene oxide ethers such as OP-glycerin ether phosphoric acid and POP / POE-pentaneerythritol ether.

Examples of the organic acid salts include sodium lactate, bile salts, and sodium 2-pyrrolidone-5-carboxylate.

The mucopolysaccharides include chondroitin sulfate, hyaluronic acid, mucoitin sulfate, caronine sulfate, keratosulfate, dermatan sulfate and the like.

[0030] Examples of the plant extract include L. japonica extract, Yarrow extract, and Melilot extract.

Other examples of humectants include atelocollagen, cholesteryl-12-hydroxystearate, short-chain soluble collagen and the like.

Of these, polyhydric alcohols exhibit a remarkable effect particularly in combination with alkylpolyglycol neopentanoate.

The amount of the humectant is not particularly limited, and is usually the amount to be added to the external preparation for skin. When considering the combined effect with the alkyl polyglycol neopentanate, the preferred amount is 0.001 to 20% by mass, more preferably 0.01 to 15% by mass, based on the total amount of the external preparation for skin.

The external preparation for skin of the present invention may optionally contain, in addition to the above-mentioned components, other components used in external preparations for skin such as cosmetics, quasi-drugs, and pharmaceuticals as necessary. It can be manufactured by a conventional method according to the dosage form to be prepared.
Examples of these optional components include powder components, liquid fats and oils, solid fats and oils, waxes, hydrocarbons, higher fatty acids, higher alcohols, esters, silicones, anionic surfactants, cationic surfactants, amphoteric surfactants, Ionic surfactants, water-soluble polymers, thickeners, film agents, ultraviolet absorbers, sequestering agents, lower alcohols, polyhydric alcohols, sugars, amino acids, organic amines, polymer emulsions,
Examples include pH adjusters, skin nutrition, vitamins, antioxidants, antioxidants, fragrances, water and the like. Specific columns of each component are shown below, and one or more of these components may be mixed as necessary.

As the powder component, for example, inorganic powders (for example, talc, kaolin, mica, sericite),
Muscovite, phlogopite, synthetic mica, rhombite, biotite, permiculite, magnesium carbonate, calcium carbonate, aluminum silicate, barium silicate, calcium silicate, magnesium silicate, strontium silicate, metal tungstate, magnesium, Silica, zeolite, barium sulfate, calcined calcium sulfate (baked gypsum), calcium phosphate, fluoroapatite, hydroxyapatite, ceramic powder, metal soap (for example, zinc myristate, calcium palmitate, aluminum stearate), boron nitride, etc .; organic Powders (eg, polyamide resin powder (nylon powder), polyethylene powder, polymethyl methacrylate powder, polystyrene powder, copolymer resin powder of styrene and acrylic acid, benzoguanamine resin powder, polytetrafluoroethylene Powder, cellulose powder, etc.);

Inorganic white pigments (eg, titanium dioxide, zinc oxide, etc.); inorganic red pigments (eg, iron oxide (iron oxide), iron titanate, etc.); inorganic brown pigments (eg, γ-
Inorganic yellow pigments (e.g., yellow iron oxide, loess); inorganic black pigments (e.g., black iron oxide, lower titanium oxide, etc.); inorganic purple pigments (e.g., mango violet, cobalt violet) Inorganic green pigments (eg, chromium oxide, chromium hydroxide, cobalt titanate, etc.); inorganic blue pigments (eg, ultramarine, navy blue, etc.); pearl pigments (eg, titanium oxide coated mica, titanium oxide coated oxy). Bismuth chloride, titanium oxide coated talc, colored titanium oxide coated mica, bismuth oxychloride, fish scale foil, etc .; metal powder pigments (eg, aluminum powder, copper powder, etc.); organic pigments such as zirconium, barium or aluminum lake (eg, Red 201, Red 202, Red 204
No., Red No. 205, Red No. 220, Red No. 226, Red No. 228, Red No. 405, Orange No. 203, Orange No. 204
No. Yellow No. 205, Yellow No. 401, Blue No. 404, Red No. 3, Red No. 104, Red No. 106, Red No. 227, Red No. 230, Red No. 401, Red No. 505, Orange 205
No. 4, Yellow No. 4, Yellow No. 5, Yellow No. 202, Yellow No. 203
No. 3, green No. 3, blue No. 1, etc.); natural pigments (eg, chlorophyll, β-carotene, etc.).

Examples of liquid fats and oils include avocado oil,
Camellia oil, turtle oil, macadamia nut oil, corn oil, mink oil, olive oil, rapeseed oil, egg yolk oil, sesame oil, persic oil, wheat germ oil, sasanqua oil, castor oil, linseed oil, safflower oil, cottonseed oil, eno oil, Examples include soybean oil, peanut oil, teaseed oil, kaya oil, rice bran oil, sinagiri oil, Japanese kiri oil, jojoba oil, germ oil, triglycerin and the like.

Examples of solid fats and oils include cocoa butter, coconut oil, horse fat, hardened coconut oil, palm oil, tallow, sheep fat, hardened tallow, palm kernel oil, lard, beef bone fat, mokuro kernel oil, hardened kernel oil Oil, beef tallow, mocro, hardened castor oil and the like.

Examples of waxes include beeswax, candelilla wax, cotton wax, carnauba wax, bayberry wax, ibota wax, whale wax, montan wax, nuka wax, lanolin, kapok wax, lanolin acetate, liquid lanolin,
Sugar cane wax, isopropyl lanolin fatty acid, hexyl laurate, reduced lanolin, jojoba wax, hard lanolin, shellac wax, POE lanolin alcohol ether, POE lanolin alcohol acetate, POE cholesterol ether, lanolin fatty acid polyethylene glycol, POE hydrogenated lanolin alcohol ether and the like. .

Examples of the hydrocarbon oil include liquid paraffin, ozokerite, squalane, pristane, paraffin, ceresin, squalene, petrolatum, microcrystalline wax and the like.

Examples of higher fatty acids include lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, oleic acid, undecylenic acid, tallic acid, isostearic acid, linoleic acid, linoleic acid, eicosapentaenoic acid (EPA), Docosahexaenoic acid (DHA) and the like.

The higher alcohols include, for example, straight-chain alcohols (eg, lauryl alcohol, cetyl alcohol, stearyl alcohol, behenyl alcohol, myristyl alcohol, oleyl alcohol, cetostearyl alcohol, etc.); and branched-chain alcohols (eg, monostearyl glycerin ether ( Butyl alcohol), 2
-Decyltetradecinol, lanolin alcohol, cholesterol, phytosterol, hexyldecanol, isostearyl alcohol, octyldodecanol, etc.).

Examples of synthetic ester oils include isopropyl myristate, cetyl octoate, octyl dodecyl myristate, isopropyl palmitate, butyl stearate, hexyl laurate, myristyl myristate,
Decyl oleate, hexyl decyl dimethyl octoate, cetyl lactate, myristyl lactate, lanolin acetate, isocetyl stearate, isocetyl isostearate, 1
Cholesteryl 2-hydroxystearate, ethylene glycol di-2-ethylhexanoate, fatty acid ester of dipentaerythritol, N-alkyl glycol monoisostearate, neopentyl glycol dicaprate, diisostearyl malate, di-2-heptylundecanoic acid Glycerin, trimethylolpropane tri-2-ethylhexanoate, trimethylolpropane triisostearate, pentaerythritol tetra-2-ethylhexanoate, glycerin tri-2-ethylhexanoate, glycerin trioctanoate, glycerin triisopalmitate, triglycol Trimethylolpropane isostearate, cetyl 2-ethylhexanoate, 2-ethylhexyl palmitate, glyceryl trimmyristate, tri-2-heptylun Kang acid glyceride, castor oil fatty acid methyl ester, oleyl oleate, aceto glyceride, 2-heptylundecyl palmitate, diisobutyl adipate, N- lauroyl -L- glutamic acid-2-octyldodecyl ester, adipate -
2-heptylundecyl, ethyl laurate, di-2-ethylhexyl sebacate, 2-hexyldecyl myristate, 2-hexyldecyl palmitate, 2-hexyldecyl adipate, diisopropyl sebacate, 2-ethylhexyl succinate, citrate Triethyl acid and the like.

Examples of the silicone oil include linear polysiloxanes (eg, dimethylpolysiloxane, methylphenylpolysiloxane, diphenylpolysiloxane, etc.); cyclic polysiloxanes (eg, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, Dodecamethylcyclohexasiloxane, etc.) Silicone resin, silicone rubber, and various modified polysiloxanes that form a three-dimensional network structure (amino-modified polysiloxane, polyether-modified polysiloxane, alkyl-modified polysiloxane, fluorine-modified polysiloxane, etc.) And the like.

Examples of the anionic surfactant include fatty acid soaps (eg, sodium laurate, sodium palmitate, etc.); higher alkyl sulfates (eg, sodium lauryl sulfate, potassium lauryl sulfate, etc.); alkyl ether sulfates (For example,
POE-triethanolamine lauryl sulfate, POE-
N-acyl sarcosine acids (eg, lauroyl sarcosine sodium, etc.); higher fatty acid amide sulfonates (eg, N-myristoyl-N-methyltaurine sodium, coconut fatty acid sodium methyltauride, laurylmethyltau) Sodium phosphate, etc.); phosphoric acid ester salts (POE-sodium oleyl ether phosphate, POE-stearyl ether phosphoric acid, etc.); sulfosuccinates (eg, sodium di-2-ethylhexylsulfosuccinate, monolauroyl monoethanolamide polyoxyethylene) Sodium sulfosuccinate, sodium lauryl polypropylene glycol sulfosuccinate, etc.); alkyl benzene sulfonates (eg, sodium linear dodecylbenzene sulfonate, linear dodede Higher fatty acid ester sulfates (eg, hydrogenated coconut oil fatty acid sodium glycerin sulfate); N-acyl glutamates (eg, monosodium N-lauroyl glutamate); Disodium N-stearoyl glutamate, monosodium N-myristoyl-L-glutamate and the like); sulfated oil (for example, funnel oil); POE-alkyl ether carboxylic acid; POE-alkyl allyl ether carboxylate; α-olefin sulfone Higher fatty acid ester sulfonate; Secondary alcohol sulfate ester salt; Higher fatty acid alkylolamide sulfate salt; Sodium lauroyl monoethanolamidosuccinate; N-palmitoyl aspartic acid Ditriethanolamine; sodium caseinate;

Examples of the cationic surfactant include alkyltrimethylammonium salts (eg, stearyltrimethylammonium chloride, lauryltrimethylammonium chloride); and alkylpyridinium salts (eg,
Cetylpyridinium chloride, etc.); distearyldimethylammonium dialkyldimethylammonium salt; poly (N, N'-dimethyl-3,5-methylenepiperidinium) chloride; alkyl quaternary ammonium salt; alkyldimethylbenzylammonium salt; alkyliso Quinolinium salt; dialkyl morphonium salt; POE-alkylamine; alkylamine salt; polyamine fatty acid derivative;
Amyl alcohol fatty acid derivatives; benzalkonium chloride; benzethonium chloride and the like.

Examples of the amphoteric surfactant include imidazoline amphoteric surfactants (for example, 2-undecyl-
N, N, N- (hydroxyethylcarboxymethyl)-
2-imidazoline sodium, 2-cocoyl-2-imidazolinium hydroxide-1-carboxyethyloxy disodium salt and the like; betaine surfactants (for example, 2-heptadecyl-N-carboxymethyl-N-hydroxyethylimidazo) Linium betaine, lauryl dimethylamino acetate betaine, alkyl betaine, amido betaine, sulfo betaine, etc.).

The lipophilic nonionic surfactant includes, for example, sorbitan fatty acid esters (for example, sorbitan monooleate, sorbitan monoisostearate, sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan monostearate) Oleate, sorbitan trioleate, diglycerol penta-2-ethylhexyl sorbitan, tetra-2
Glycerin polyglycerin fatty acids (eg, mono-cottonseed oil fatty acid glycerin, glycerin monoerucate, glycerin sesquioleate, glycerin monostearate)
α, α'-oleic acid glyceryl pyroglutamate, glyceryl monostearate malic acid, etc.); propylene glycol fatty acid esters (eg, propylene glycol monostearate); hydrogenated castor oil derivatives; glycerin alkyl ether;

As the hydrophilic nonionic surfactant, for example, POE-sorbitan fatty acid esters (for example, P
OE-sorbitan monooleate, POE-sorbitan monostearate, POE-sorbitan monooleate,
POE-sorbitan tetraoleate and the like); POE sorbite fatty acid esters (for example, POE-sorbit monolaurate, POE-sorbit monooleate,
POE-sorbit pentaoleate, POE-sorbit monostearate, etc.); POE-glycerin fatty acid esters (eg, POE-glycerin monostearate, POE-glycerin monoisostearate, POE)
POE-monooleate such as E-glycerin triisostearate, etc.); POE-fatty acid esters (for example,
POE-distearate, POE-monodioleate,
POE-alkyl ethers (eg, POE-lauryl ether,
POE-oleyl ether, POE-stearyl ether, POE-behenyl ether, POE-2-octyldodecyl ether, POE-cholestanol ether, etc.); Pluronic type (for example, Pluronic etc.);
POE.POP-alkyl ethers (for example, POE
-POP-cetyl ether, POE-POP-2-decyltetradecyl ether, POE-POP-monobutyl ether, POE-POP-hydrogenated lanolin, POE-P
OP-glycerin ether);

Tetra-POE.tetra-POP-ethylenediamine condensates (for example, Tetronic, etc.);
Castor oil-hardened castor oil derivatives (eg, POE-castor oil, POE-hardened castor oil, POE-hardened castor oil monoisostearate, POE-hardened castor oil triisostearate, POE-hardened castor oil monopyroglutamate monoisostearin Acid diesters, POE-hardened castor oil maleic acid, etc.); POE- beeswax lanolin derivatives (eg, POE-sorbitol beeswax, etc.); alkanolamides (eg, coconut oil fatty acid diethanolamide, lauric acid monoethanolamide, fatty acid isopropanolamide, etc.) POE-propylene glycol fatty acid ester; POE-alkylamine; POE-fatty acid amide; sucrose fatty acid ester; alkylethoxydimethylamine oxide; trioleyl phosphoric acid and the like.

Examples of natural water-soluble polymers include, for example, plant polymers (for example, gum arabic, tragacanth gum, galactan, guar gum, carob gum, karaya gum, carrageenan, pectin, agar, quince seed (quince), alge colloid (cassow extract) ),
Starch (rice, corn, potato, wheat), glycyrrhizic acid); microbial macromolecules (eg,
Xanthan gum, dextran, succinoglucan, burlan, etc.); and animal-based polymers (eg, collagen, casein, albumin, gelatin, etc.).

The semi-synthetic water-soluble polymer includes, for example,
Starch-based polymers (for example, carboxymethyl starch, methylhydroxypropyl starch, etc.); cellulose-based polymers (methylcellulose, ethylcellulose, methylhydroxypropylcellulose, hydroxyethylcellulose, sodium cellulose sulfate, hydroxypropylcellulose, carboxymethylcellulose, sodium carboxymethylcellulose, Crystalline cellulose,
Alginic acid-based polymers (eg, sodium alginate, propylene glycol alginate, etc.);

Examples of the synthetic water-soluble polymer include vinyl polymers (eg, polyvinyl alcohol, polyvinyl methyl ether, polyvinyl pyrrolidone, carboxyvinyl polymer, etc.); and polyoxyethylene polymers (eg, polyethylene glycol 20, 000, 4
000, 60,000 polyoxyethylene polyoxypropylene copolymers, etc.); acrylic polymers (eg, sodium polyacrylate, polyethyl acrylate, polyacrylamide, etc.); polyethylene imines; cationic polymers, etc. .

Examples of the thickener include gum arabic,
Carrageenan, karaya gum, tragacanth gum, carob gum, quince seed (quince), casein, dextrin, gelatin, sodium pectate, sodium alginate, methylcellulose, ethylcellulose,
CMC, hydroxyethylcellulose, hydroxypropylcellulose, PVA, PVM, PVP, sodium polyacrylate, carboxyvinyl polymer, locust bean gum, guar gum, tamarind gum, dialkyldimethylammonium cellulose sulfate, xanthan gum, aluminum magnesium silicate, bentonite,
Hectorite, silicic acid A1Mg (Vegum), laponite, silicic anhydride and the like.

Examples of the ultraviolet absorber include, for example, benzoic acid-based ultraviolet absorbers (for example, para-aminobenzoic acid (hereinafter, referred to as para-aminobenzoic acid).
PABA), PABA monoglycerin ester,
N, N-dipropoxy PABA ethyl ester, N, N
-Diethoxy PABA ethyl ester, N, N-dimethyl PABA ethyl ester, N, N-dimethyl PABA
Butyl ester, N, N-dimethyl PABA ethyl ester, etc.); anthranilic acid UV absorbers (e.g., homomenthyl-N-acetylanthranilate); salicylic acid UV absorbers (e.g., amyl salicylate, etc.)
Menthyl salicylate, homomenthyl salicylate, octyl salicylate, phenyl salicylate, benzyl salicylate, p-isopropanol phenyl salicylate, etc.);

Cinnamic acid ultraviolet absorbers (for example, octylcinnamate, ethyl-4-isopropylcinnamate, methyl-2,5-diisopropylcinnamate, ethyl-2,4-diisopropylcinnamate, methyl-
2,4-diisopropylcinnamate, propyl-p-
Methoxycinnamate, isopropyl-p-methoxycinnamate, isoamyl-p-methoxycinnamate,
Octyl-p-methoxycinnamate (2-ethylhexyl-p-methoxycinnamate), 2-ethoxyethyl-p-methoxycinnamate, cyclohexyl-p-methoxycinnamate, ethyl-α-cyano-β-phenylcinnamate, 2-ethylhexyl-α-cyano-β
Phenylcinnamate, glycerylmono-2-ethylhexanoyl-diparamethoxycinnamate, etc.); benzophenone ultraviolet absorbers (for example, 2,4-dihydroxybenzophenone, 2,2′-dihydroxy-4-)
Methoxybenzophenone, 2,2'-dihydroxy-
4,4′-dimethoxybenzophenone, 2,2 ′, 4
4'-tetrahydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-
4-methoxy-4'-methylbenzophenone, 2-hydroxy-4-methoxybenzophenone-5-sulfonate, 4-phenylbenzophenone, 2-ethylhexyl-4'-phenyl-benzophenone-2-carboxylate, 2-hydroxy- 4-n-octoxybenzophenone, 4-hydroxy-3-carboxybenzophenone, etc.);

3- (4'-methylbenzylidene) -d,
l-camphor, 3-benzylidene-d, l-camphor; 2-phenyl-5-methylbenzoxazole;
2'-hydroxy-5-methylphenylbenzotriazole; 2- (2'-hydroxy-5'-t-octylphenyl) benzotriazole; 2- (2'-hydroxy-5'-methylphenylbenzotriazole;dibenzarazine; dianiline Soil methane; 4-methoxy-4'-t
-Butyldibenzoylmethane; 5- (3,3-dimethyl-2-norbornylidene) -3-pentan-2-one and the like.

As the sequestering agent, for example, 1-
Hydroxyethane-1,1-diphosphonic acid, 1-hydroxyethane-1,1-diphosphonic acid tetrasodium salt, disodium edetate, trisodium edetate, tetrasodium edetate, sodium citrate, sodium polyphosphate, metaphosphoric acid Sodium, gluconic acid, phosphoric acid, citric acid, ascorbic acid, succinic acid, edetic acid,
Ethylenediaminehydroxyethyl triacetic acid trisodium and the like.

Examples of the lower alcohol include ethanol, propanol, isopropanol, isobutyl alcohol and t-butyl alcohol.

As the polyhydric alcohol derivative, for example,
Ethylene glycol alkyl ethers (for example, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, ethylene glycol monophenyl ether,
Ethylene glycol monohexyl ether, ethylene glycol mono 2-methylhexyl ether, ethylene glycol monoisoamyl ether, ethylene glycol monobenzyl ether, ethylene glycol monoisopropyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol dibutyl ether, etc.);

Polyethylene glycol alkyl ethers (for example, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol butyl ether, diethylene glycol methyl ethyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl Ether); propylene glycol alkyl ethers (propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, propylene glycol monoisopropyl ether, etc.); polypropylene glycol alkyl Ethers (eg, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol monobutyl ether); ethylene glycol ether esters (eg, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene glycol monobutyl ether acetate) , Ethylene glycol monophenyl ether acetate, etc.); ethylene glycol diesters (ethylene glycol didibate, ethylene glycol disuccinate, etc.); polyethylene glycol ether esters (diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, etc.); propylene glycol Ether es Le acids (propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate,
Propylene glycol monophenyl ether acetate); glycerin monoalkyl ether (eg, xyl alcohol, seraky alcohol, butyl alcohol, etc.); glysolid; tetrahydrofurfuryl alcohol.

The monosaccharides include, for example, sucrose maltose tricarbonate (eg, D-glyceryl aldehyde, dihydroxyacetone, maltotriose, etc.); tetracarbon sugar (eg, D-erythrose, D-erythrulose, D-threose) Pentoses (eg, L-arabinose, D-xylose, L-lyxose, D-arabinose, D-ribose, D-ribulose, D-xylulose, L-xylulose, etc.); hexoses (eg, , D
-Glucose, D-talose, D-bucose, D-galactose, D-fructose, L-galactose, L
-Mannose, D-tagatose, etc.);
Aldoheptose, heprose, etc.);
Octulose etc.); deoxy sugars (eg, 2-deoxy-D-ribose, 6-deoxy-L-galactose, 6
-Deoxy-L-mannose and the like); amino sugars (for example,
Uronic acid (for example, D-glucosamine, D-galactosamine, sialic acid, aminouronic acid, muramic acid, etc.);
-Glucuronic acid, D-mannuronic acid, L-guluronic acid,
D-galacturonic acid, L-iduronic acid, etc.).

The oligosaccharides include, for example, sucrose, guntianose, umbelliferose, lactose, planteose, isoliqunoses, α, α-trehalose,
Raffinose, liqunoses, umbilicin, stachyose bell bath courses and the like.

Examples of polysaccharides include cellulose, quince seed, starch, glycogen, gum arabic,
Examples include tragacanth gum, xanthan gum, guar gum, dextran, locust bingham, succinoglucan and the like.

The amino acids include, for example, neutral amino acids (eg, threonine, cysteine, etc.); basic amino acids (eg, hydroxylysine, etc.). Examples of amino acid derivatives include acyl sarcosine sodium (sodium lauroyl sarcosine), acyl glutamate, sodium acyl β-alanine, glutathione, and pyrrolidone carboxylic acid.

Examples of the organic amine include monoethanolamine, diethanolamine, triethanolamine, morpholine, triisopropanolamine, 2-amino-2-methyl-1,3-propanediol, and 2-amino-2-methyl-1. -Propanol and the like.

Examples of the polymer emulsion include acrylic resin emulsion, polyethyl acrylate emulsion, polyacryl alkyl ester emulsion,
Examples include a polyvinyl acetate resin emulsion and a natural rubber latex.

Examples of the pH adjusting agent include buffers such as lactic acid-sodium lactate, citric acid-sodium citrate, and succinic acid-sodium succinate.

Examples of the vitamins include vitamins A, B ₁ , B ₂ , B ₆ , C, E and derivatives thereof, pantothenic acid and derivatives thereof, and biotin.

Examples of the antibacterial agent include benzoic acid, salicylic acid, sorbic acid, p-hydroxybenzoic acid alkyl ester, phenoxyethanol, hexachlorophen and the like.

Examples of the antioxidant include tocopherols, dibutylhydroxytoluene, butylhydroxyanisole, gallic esters and the like.

As the antioxidant aid, for example, phosphoric acid,
Examples thereof include citric acid, ascorbic acid, maleic acid, malonic acid, succinic acid, fumaric acid, kephalin, hexametaphosphate, phytic acid, and ethylenediaminetetraacetic acid.

Examples of the whitening agent include L-ascorbic acid alkyl ester, L-ascorbic acid phosphate, L-ascorbic acid sulfate and the like.
Specific examples include L-ascorbyl palmitate, L-ascorbyl isopalmitate, L-ascorbyl dipalmitate, L-ascorbyl diisopalmitate, L-ascorbyl stearate, L-ascorbyl isostearate, L-ascorbyl distearate L-ascorbyl diisostearate, L-ascorbyl myristate, L-ascorbyl isomyristate, L-ascorbyl dimyristate, L-ascorbyl diisomyristate, L-ascorbyl 2-ethylhexanoate,
L-ascorbic acid alkyl esters such as L-ascorbyl di-2-ethylhexanoate, L-ascorbyl oleate and L-ascorbyl dioleate; L-ascorbic acid-2-phosphate; L-ascorbic acid-3-
Phosphate ester, DL-α-tocophenol-2-L-
L-ascorbic acid phosphate such as ascorbic acid diester, L-ascorbic acid-2-sulfate, and L-ascorbic acid-3-sulfate such as L-ascorbic acid-3-sulfate
L-ascorbic acid derivatives such as ascorbic acid sulfate ester or salts thereof (such as alkali metal salts such as sodium salt and potassium salt, alkaline earth metal salts such as calcium salt and magnesium salt); kojic acid such as alkyl kojic acid ester Kojic acid derivatives such as esters and kojic acid ethers such as kojic acid alkyl ether;

Hydroquinone α-D-glucose, hydroquinone β-D-glucose, hydroquinone α-L
-Glucose, hydroquinone β-L-glucose, hydroquinone α-D-galactose, hydroquinone β
Hexose glycosides such as -D-galactose, hydroquinone α-L-galactose, hydroquinone β-L-galactose, hydroquinone α-D-ribose, hydroquinone β-D-ribose, hydroquinone α-L-ribose, and hydroquinone β Pentacarbon sugar glycosides such as -L-ribose, hydroquinone α-D-arabinose, hydroquinone β-D-arabinose, hydroquinone α-L-arabinose, hydroquinone β-L-arabinose, hydroquinone α-D-glucosamine, hydroquinone β −
D-glucosamine, hydroquinone α-L-glucosamine, hydroquinone β-L-glucosamine, hydroquinone α-D-galactosamine, hydroquinone β-D-
Amino acid glycosides such as galactosamine, hydroquinone α-L-galactosamine, hydroquinone β-L-galactosamine, hydroquinone α-D-glucuronic acid, hydroquinone β-D-glucuronic acid, hydroquinone α-
L-glucuronic acid, hydroquinone β-L-glucuronic acid, hydroquinone α-D-galacturonic acid, hydroquinone β-D-galacturonic acid, hydroquinone α-L
-Glycosides of hydroquinone such as uronic acid glycosides such as galacturonic acid and hydroquinone β-L-galacturonic acid and derivatives thereof (esters such as acetylation and ethers such as methylated products);

Saxifrage extract, glutathione, tranexamic acid, dimer of tranexamic acid (for example, trans-4- (trans-aminomethylcyclohexanecarbonyl) aminomethylcyclohexanecarboxylic acid hydrochloride, etc.), ester of tranexamic acid and hydroquinone ( For example, trans-4-aminomethylcyclohexanecarboxylic acid 4′-hydroxyphenyl ester and the like, and esters of tranexamic acid and gentisic acid (for example, 2
Amides of-(trans-4-aminomethylcyclohexylcarbonyloxy) -5-hydroxybenzoic acid and salts thereof) and tranexamic acid (e.g., trans-
Tranexamic acids such as 4-aminomethylcyclohexanecarboxylic acid methylamide and its salts, trans-4- (P-methoxybinzoyl) aminomethylcyclohexanecarboxylic acid and its salts, trans-4-guanidinomethylcyclohexanecarboxylic acid and its salts, etc. Derivatives, and salts thereof (eg, alkali metal salts such as sodium salt and potassium salt, alkaline earth metal salts such as calcium salt and magnesium salt, ammonium salt, and alkanolamine salts such as triethanolamine).

Examples of the blood circulation promoting agent include nonylate valenylamide, nicotinic acid benzyl ester, nicotinic acid β-butoxyethyl ester, capsaicin, zingerone, cantaristin tincture, ictamol, tannic acid,
α-borneol, tocopherol nicotinate, inositol hexanicotinate, cyclanderate, cinnarizine, tolazoline, acetylcholine, verapamil, cepharanthin, γ-oryzanol and the like.

In addition, anti-inflammatory agents (eg, glycyrrhizic acid derivatives, glycyrrhetinic acid derivatives, salicylic acid derivatives, hinokitiol, zinc oxide, allantoin, etc.); Loquat, carrot,
Aloe, mallow, iris, grape, yoquinin,
Loofah, lily, saffron, senkyu, ginger,
Hypericum, Ononis, Garlic, Pepper, Chimney, Touki, Seaweed, etc .; Activator (eg, Royal Jelly, Photosensitizer, Cholesterol Derivative, etc.); Antiseborrheic (eg, Sulfur, Thiantol, etc.); Anti-inflammatory Agent (eg, Tranexamic acid, thiotaurine, hypotaurine, etc.).

The external preparation for skin of the present invention can be obtained by blending the above components and treating according to a conventional method. The dosage form of the external preparation for skin of the present invention is optional, a solution system,
Any dosage form such as a solubilizing system, an emulsifying system, a powder dispersion system, a water-oil two-layer system, a water-oil-powder three-layer system may be used. Further, the product form of the external preparation for skin of the present invention is also arbitrary, and facial cosmetics such as lotion, milky lotion, cream, pack, etc .; makeup cosmetics such as foundation, lipstick, eye shadow, etc .; body cosmetics; It can be used for skin removers such as makeup removers and body shampoos; ointments and the like.

In the present invention, in addition to a skin external preparation which is the most preferred use, products such as conventionally known drugs, quasi-drugs, cosmetics, etc., for example, hair cleansing agents such as shampoos and rinses; Hair styling agents), etc .; it can be used as it is in a bath agent to make each product. These products can be produced by a conventional method by blending one or more optional components constituting each product with an alkyl polyglycol neopentanoate.

[0080]

The present invention will be specifically described below with reference to examples.

First, specific examples of the synthesis of the alkyl polyglycol neopentanoate according to the present invention will be described with reference to examples.

Example 1 60 g of ethyltriglycol neopentanoate neopentyl chloride was added to 100 m of methylene chloride.
L, and 45 g of triethylamine was added as a catalyst. To this, 37 g of ethyl triglycol was gradually added with stirring, and the mixture was reacted at room temperature for 3 hours. After the reaction, the reaction solution was neutralized by adding hydrochloric acid, and partitioned with water and chloroform.
After the chloroform layer was concentrated, it was subjected to silica gel column chromatography. The fraction containing ethyl tripentanoate triglycol was concentrated and distilled under reduced pressure to obtain 80 g of ethyl triglycol neopentanoate. ¹ H-NMR of ethyl triglycol neopentanoate thus obtained and
The ^{1 3} C-NMR shown in FIGS. The assignment is shown in the figure.

Example 2 60 g of propyltriglycol neopentanoate neopentyl chloride was added to 100 m of methylene chloride.
L, and 45 g of triethylamine was added as a catalyst. To this, 50 g of propyltriglycol was gradually added with stirring, and reacted at room temperature for 4 hours. After the reaction, the reaction solution was neutralized by adding hydrochloric acid, and partitioned with water and chloroform. The chloroform layer was concentrated and then subjected to silica gel column chromatography. The fraction containing propyl triglycol neopentanate was concentrated and distilled under reduced pressure to obtain 92 g of propyl triglycol neopentanate. Neopentanoate propyl triglycol so obtained ¹ H-
The structure was confirmed by NMR and ¹³ C-NMR.

Hereinafter, the present invention will be specifically described with reference to examples of a moisturizing agent and a skin external preparation. The compounding amount is mass%.
Prior to the description of the examples, test methods and evaluation methods used in the present invention will be described.

“Testing Method by Conductance Measurement” 10
Using the forearm of the name panel, before application and 30 minutes after application, 6
After 0 minute and 120 minutes, the skin conductance was measured, and the rate of change was used to evaluate the moisturizing effect. The rate of change in skin conductance is determined by the following formula, and it is possible to examine the effect on the water absorption and water retention of the stratum corneum. It can be evaluated that the moisturizing effect is high.

Conductance change rate = (Conductance before application) / (Conductance after application)

The evaluation criteria of the “test by conductance measurement” are as follows. ◎: Average of conductance change rate of 10 panelists: 0 or more and less than 0.1…: Average of conductance change rate of 10 panelists: 0.
1 or more and less than 0.2 Δ: average of the conductance change rate of 10 panelists: 0.
2 or more and less than 0.5 ×: average of the conductance change rate of 10 panelists: 0.
5 or more

"Evaluation (1): Good familiarity with skin" A practical use test was carried out by 10 specialized panelists on good familiarity with the skin during use. The evaluation criteria are as follows. …: Eight or more specialized panelists recognized that the adaptation to the skin during use was good. …: 6 or more and less than 8 specialized panelists recognized that the familiarity with the skin during use was good. Δ: 3 or more and less than 6 specialized panelists recognized that the familiarity with the skin during use was good. ×: Less than three professional panelists recognized that the adaptation to the skin during use was good.

“Evaluation (2): Smoothness of skin” The actual use test was carried out by 10 specialized panelists on the smoothness of the skin during and after use. The evaluation criteria are as follows. A: Eight or more professional panelists recognized that the skin was smooth during and after use. …: Six or more and less than eight specialized panelists recognized that the skin was smooth during and after use. B: Three or more and less than six professional panelists recognized that the skin was smooth during and after use. X: Less than 3 professional panelists recognized that the skin was smooth during and after use.

"Evaluation (3): Non-stickiness to skin" A panel 1 specialized in non-stickiness to the skin during and after use.
The actual use test was performed by 0 persons. The evaluation criteria are as follows. A: Eight or more specialized panelists recognized that there was no stickiness to the skin during and after use. …: Six or more and less than eight specialized panelists recognized that there was no stickiness to the skin during and after use. Δ: Three or more and less than six professional panelists recognized that there was no stickiness to the skin during and after use. ×: Less than 3 professional panelists recognized that there was no stickiness to the skin during and after use.

"Evaluation (4): Feeling of moisturizing effect" An actual use test was carried out by 10 expert panelists for the presence or absence of moisturizing effect 120 minutes after use. The evaluation criteria are as follows. …: Eight or more specialized panelists recognized that there was a feeling of moisturizing effect. …: Six or more and less than eight specialized panelists recognized that there was a feeling of moisturizing effect. Δ: 3 or more and less than 6 specialized panelists recognized that there was a feeling of moisturizing effect. X: Less than 3 professional panelists recognized that there was a feeling of moisturizing effect.

"Examples 3 and 4, Comparative Examples 1 to 3" The conductance change rates of the compounds of Examples 3 to 4 and Comparative Examples 1 to 3 shown in Table 1 were measured.

[0093]

[Table 1]

As can be seen from Table 1, the 1% aqueous solution of ethyltriglycol neopentanate and the 1% aqueous solution of propyltriglycol neopentanate have a small conductance change rate, a high moisturizing effect, and the effect lasts long. Examples 3 and 4).

On the other hand, ion-exchanged water (Comparative Example 1) and a 10% aqueous solution of 1,3-butylene glycol (Comparative Example 2)
All have low moisturizing effects. In addition, glycerin 10%
The aqueous solution has a high moisturizing effect, but for a long time (120 minutes)
It can be seen that the effect does not last (Comparative Example 3).

"Examples 5 and 6, Comparative Examples 4 and 6" Evaluation tests of the respective compounds described in Tables 2 and 3 were conducted. The results are shown in each table.

[0097]

[Table 2]

Table 2 shows that the alkylpolyglycol neopentanoate of the present invention has an excellent moisturizing function for the skin, particularly, an excellent moisturizing function for the skin. Further, when used on the skin, the skin is well-adapted to the skin, and is excellent in use feel such as smoothness and stickiness of the skin. From these facts, it is understood that the alkyl polyglycol neopentanoate of the present invention is useful as a humectant having an excellent feeling on use on the skin.

[0099]

[Table 3]

From Table 3, glycerin and 1,3-butylene glycol conventionally known as humectants are:
It can be seen that no satisfactory effects can be obtained in terms of good familiarity with the skin, lack of stickiness to the skin, and moisturizing effect.

"Examples 7 to 11, Comparative Examples 7 to 9" Tables 4 to
The skin external preparations (lotions) of Examples 7 to 11 and Comparative Examples 7 to 9 each having the composition described in Table 5 were produced by a conventional method.
An evaluation test was performed. The results are shown in each table.

[0102]

[Table 4]

As can be seen from Table 4, the lotions of Examples 7 to 10 containing ethyl triglycol neopentanoate had good skin familiarity, smooth skin, non-stickiness to skin, and moisturizing effect. It can be seen that in each case, a sufficient effect can be obtained. In addition, the lotion of Example 11 in which propyltriglycol neopentanoate was blended in place of ethyltriglycol neopentanoate also showed good skin familiarity, smooth skin, non-stickiness to skin, and moisturizing effect. In each case, sufficient effects were obtained.

[0104]

[Table 5]

As can be seen from Table 5, the lotions of Comparative Examples 7 to 9 containing glycerin and 1,3-butylene glycol, which are conventionally known as humectants, and not containing alkylpolyglycol neopentanoate, It can be seen that none of them are satisfactory in terms of good familiarity, lack of stickiness to the skin, and a feeling of moisturizing effect.

"Examples 12 to 14" The conductance change rates of Examples 12 to 14 having the composition shown in Table 6 were measured.

[0107]

[Table 6]

From Table 6, it can be seen that when an aqueous solution containing ethyltriglycol neopentanate and propyltriglycol neopentanate is combined with a humectant, the conductance change rate is synergistically reduced and the moisturizing effect is synergistically increased.

"Examples 15 to 19" External preparations for skin (Examples 15 to 19) each having the composition shown in Table 7
Was produced by a conventional method, and an evaluation test was conducted. The results are shown in Table 7 above.

[0110]

[Table 7]

As can be seen from Table 7, Example 15 in which ethyltriglycol neopentanoate was blended with glycerin and 1,3-butylene glycol, which did not fit well to the skin, had no stickiness to the skin, and had insufficient moisturizing effect. ~ 1
No. 8 shows that sufficient effects can be obtained in terms of good fit to the skin, smoothness of the skin, non-stickiness to the skin, and a feeling of moisturizing effect. In particular, although not shown in the table,
The synergistic effect of the moisturizing effect and the effect of improving the stickiness of the skin were observed. It is also found that when 0.1% by mass or more of ethyltriglycol neopentanate is blended, a remarkable synergistic effect is exhibited. In addition, Example 19 in which propyl triglycol neopentanate was blended in place of ethyl triglycol neopentanoate also showed good conformability to the skin, smoothness of the skin, lack of stickiness to the skin, and a feeling of moisturizing effect. In each case, a remarkable synergistic effect was obtained.

Hereinafter, other embodiments of the present invention will be described.
It was confirmed that all of the following examples have excellent effects of the present invention, such as good adaptability to the skin, excellent skin smoothness, no stickiness, and a long-lasting moisturizing effect.

Example 20 Lotion Component Content (% by mass) Ethanol 10.0 Glycerin 2.0 1,3-butylene glycol 3.0 Ethyl triglycol neopentanoate 0.5 Propyl triglycol neopentanoate 0.5 Nicotinic acid Amide 0.3 Sodium pyrrolidonecarboxylate 0.5 Purified water residue (Preparation method) Other components were dissolved in purified water at room temperature to obtain a lotion.

Example 21 Toner Lotion Ingredients (% by mass) Ethanol 10.0 1,3-butylene glycol 5.0 Propyltriglycol neopentanoate 0.3 Nicotinamide 0.3 Sodium pyrrolidonecarboxylate 0.5 Purification Water residue (Production method) Other components were dissolved in purified water at room temperature to obtain a lotion.

Example 22 Lotion Component Incorporation Amount (% by mass) Aqueous phase buffer Appropriate amount Anti-fading agent Appropriate amount Purified water residue B. Alcohol phase ethyl triglycol neopentanate 0.1 oleyl alcohol 0.1 POE (20) sorbitan monolaurate 0.5 POE (15) lauryl alcohol ether 0.5 ethanol 10.0 preservatives appropriate amount perfume appropriate amount Coloring agent Coloring agent Appropriate amount (Preparation method) Dissolve other aqueous phase components in purified water at room temperature to obtain an aqueous phase. The other alcohol phase components are dissolved in ethanol and mixed and solubilized in the aqueous phase. After that, after toning with colorant,
Filtration and filling were performed.

Example 23 Lotion Component Content (% by mass) Aqueous phase methylcellulose 0.2 quince seed 0.1 buffer appropriate amount anti-fading agent appropriate amount chelating agent appropriate amount purified water residue B. Alcohol phase Ethyl triglycol neopentanoate 0.01 POE (15) oleyl alcohol ether 0.5 ethanol 10.0 Preservative qs perfume qs Coloring agent Coloring agent Appropriate amount (Preparation method) Take a portion of purified water to dissolve the chelating agent, and mix and stir methylcellulose and quince seed to dissolve to form an aqueous phase. The remaining aqueous phase component is added to the remaining portion of the purified water and dissolved at room temperature, and the above aqueous phase is added thereto to obtain a uniform aqueous solution. The other alcohol phase components are dissolved in ethanol, and the resulting mixture is added to the aqueous solution and mixed to solubilize. Then, after toning with a coloring agent, filtration and filling were performed.

Example 24 Cream Ingredients Amount (% by mass) Oil phase Stearic acid 10.0 Stearyl alcohol 4.0 Butyl stearate 8.0 Monoglycerin stearate 2.0 Vitamin E acetate 0.5 Vitamin A palmitate 0.1 Ethyl triglycol neopentanate 5.0 Propyl tripentanoate Glycol 5.0 Macadamia nut oil 1.0 Tea seed oil 3.0 Fragrance 0.4 Preservatives Appropriate amount B. Aqueous phase glycerin 4.0 1,2-pentanediol 3.0 sodium hyaluronate 1.0 potassium hydroxide 2.0 magnesium ascorbate 0.1 L-arginine hydrochloride 0.01 trisodium edetate 0.05 Purified water residue (Preparation method) The oil phase of A and the aqueous phase of B are each heated to 70 ° C. and completely dissolved. Add phase A to phase B and emulsify with an emulsifier. The emulsion was cooled using a heat exchanger to obtain a cream.

Example 25 Cream Ingredients Amount (% by mass) Oil phase Cetanol 4.0 Vaseline 7.0 Isopropyl myristate 8.0 Squalane 10.0 Monoglycerin stearate 2.2 POE (20) Sorbitan monostearate 2.8 Ethyl triglycol neopentanate 5.0 Vitamin E nicotinate 2.0 Fragrance 0.3 Antioxidant qs Preservative qs Aqueous phase Glycerin 7.0 Sodium hyaluronate 0.1 Dipropylene glycol 2.9 Sodium pyrrolidonecarboxylate 1.0 Disodium edetate 0.01 Purified water residue (Production method) Oil phase part of A and water phase part of B Is heated to 70 ° C. and completely dissolved. Add phase A to phase B and emulsify with an emulsifier. The emulsion was cooled using a heat exchanger to obtain a cream.

Example 26 Emulsion Component Compounding Amount (% by mass) Oil phase squalane 5.0 oleyl oleate 3.0 petrolatum 2.0 sorbitan sesquioleate 0.8 polyoxyethylene oleyl ether (20EO) 1.2 evening primrose oil 0.5 fragrance 0.3 preservative appropriate amount B. Aqueous phase Ethyl triglycol neopentanoate 0.1 1,3-butylene glycol 4.5 Ethanol 3.0 Carboxyvinyl polymer 0.2 Potassium hydroxide 0.1 L-arginine L-aspartate 0.01 Edetate 0 .05 Purified water residue (Preparation method) The oil phase of A and the aqueous phase of B were each heated to 70 ° C. and completely dissolved. Add phase A to phase B and emulsify with an emulsifier. The emulsion was cooled using a heat exchanger to obtain an emulsion.

Example 27 Foundation Component Blending Amount (% by mass) Oil phase Cetanol 3.5 Deodorized lanolin 4.0 Jojoba oil 5.0 Vaseline 2.0 Squalane 6.0 Monoglycerin stearate 2.5 POE (60) Hardened castor oil 1.5 POE (20) Cetyl ether 1. 0 Ethyl triglycol neopentanate 2.0 Pyridoxine tripalmitate 0.1 Preservatives Appropriate perfume 0.3 B. Water phase Propylene glycol 9.5 Izayobara extract 0.5 Compound powder 12.0 Ethylenediamine human peroxyethyl triacetate trisodium 1.0 Purified water residue (Production method) The oil phase of A and the aqueous phase of B are each 70 ° C. And completely dissolved. Add phase A to phase B and emulsify with an emulsifier. The emulsion was cooled using a heat exchanger to obtain a foundation.

Example 28 Lotion Component Content (% by mass) Alcohol phase Ethanol 5.0 POE oleyl alcohol ether 2.0 Ethyl triglycol neopentanoate 0.5 2-Ethylhexyl-P-dimethylaminobenzoic acid 0.18 Fragrance 0.05 B. Aqueous phase 1,3-butylene glycol 7.5 cholesteryl-12-human peroxystearate 2.0 sodium pyrrolidone carboxylate 0.5 nicotinamide 0.3 glycerin 5.0 purified water residue The alcohol phase of A B was added to the aqueous phase and solubilized to obtain a lotion.

Example 29 Lotion Component Compounding Amount (% by mass) Alcohol phase Ethanol 5.0 POE oleyl alcohol ether 2.0 Ethyl triglycol neopentanate 1.0 2-Ethylhexyl-P-dimethylaminobenzoic acid 0.18 Fragrance 0.05 B. Aqueous phase 1,3-butylene glycol 9.5 sodium pyrrolidonecarboxylate 0.5 nicotinamide 0.3 glycerin 5.0 citric acid 0.01 sodium citrate 0.09 purified water residue B was added to the aqueous phase and solubilized to obtain a lotion.

Example 30 Emulsion Ingredients Compounding Amount (% by mass) Oil phase squalane 5.0 oleyl oleate 3.0 petrolatum 2.0 sorbitan sesquioleate 0.8 polyoxyethylene oleyl ether (20EO) 1.2 ethyltriglycol neopentanoate 8.0 evening primrose oil 0.5 fragrance 0. 3 Preservative appropriate amount B. Aqueous phase 1,3-butylene glycol 4.5 ethanol 3.0 carboxyvinyl polymer 0.2 potassium hydroxide 0.1 kojic acid 5.0 L-arginine L-aspartate 0.01 edetate 0.05 purified water Residue (Preparation method) The oil phase of A and the aqueous phase of B are each heated to 70 ° C. and completely dissolved. Add phase A to phase B and emulsify with an emulsifier. The emulsion was cooled using a heat exchanger to obtain an emulsion.

Example 31 Emulsion Ingredients Compounding Amount (% by Mass) Oil phase squalane 5.0 oleyl oleate 3.0 petrolatum 2.0 sorbitan sesquioleate 0.8 polyoxyethylene oleyl ether (20EO) 1.2 propyltriglycol neopentanate 3.0 evening primrose oil 0.5 fragrance 0. 3 Preservative appropriate amount B. Aqueous phase 1,3-butylene glycol 4.5 ethanol 3.0 carboxyvinyl polymer 0.2 potassium hydroxide 0.1 kojic acid 5.0 L-arginine L-aspartate 0.01 edetate 0.05 purified water Residue (Preparation method) The oil phase of A and the aqueous phase of B are each heated to 70 ° C. and completely dissolved. Add phase A to phase B and emulsify with an emulsifier. The emulsion was cooled using a heat exchanger to obtain an emulsion.

[0125]

As described in detail above, the novel compound alkyl polypentane neopentanate of the present invention has an excellent moisturizing function, especially a moisturizing function with excellent durability. Furthermore, it has good familiarity with the skin, and is excellent in use feel such as skin smoothness and stickiness. From these facts, the alkyl polyglycol neopentanoate of the present invention is useful as a novel humectant having an excellent use feel on the skin,
For example, it can be applied to medicines, quasi-drugs, cosmetics, etc. by blending it into a skin external preparation. Further, the skin external preparation containing the alkyl polyglycol neopentanoate of the present invention has an excellent moisturizing effect, in particular, while exhibiting a long-lasting moisturizing effect, and has good familiarity with the skin, smoothness of the skin,
Since it gives an excellent feeling of use such as stickiness to the skin, it can be applied to pharmaceuticals, quasi-drugs, cosmetics, and the like. Further, in the skin external preparation of the present invention, a synergistic moisturizing effect can be exhibited by using a humectant in combination with the alkyl polyglycol neopentanoate of the present invention.
Furthermore, it is possible to improve the familiarity of the alkyl polyglycol neopentanate with the skin and the feeling of use of the smoothness of the skin.

[Brief description of the drawings]

FIG. 1. ¹ H- of ethyltriglycol neopentanoate
It is an NMR spectrum figure.

FIG. 2: ¹³ C of ethyltriglycol neopentanoate
-It is an NMR spectrum figure.

Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat II (Reference) A61P 17/16 A61P 17/16 (72) Inventor Reiji Miyahara 2-2-1 Hayabuchi Tsuzuki-ku, Yokohama-shi, Kanagawa (72) Inventor Hiroyuki Kagogi 2-2-1 Hayabuchi, Tsuzuki-ku, Yokohama-shi, Kanagawa Prefecture Inside Shiseido Research Center (Shin-Yokohama) (72) Inventor Tomiyuki Namba Tsuzuki, Yokohama-shi, Kanagawa 2-2-1 Hayabuchi-ku Shiseido Research Center (Shin-Yokohama) F-term (reference) 4C083 AA111 AA112 AA122 AB032 AC012 AC022 AC082 AC102 AC111 AC122 AC182 AC231 AC242 AC302 AC352 AC401 AC402 AC422 AC432 AC442 AC532 AC552 AC582 AC612 AC842 AC852 AD092 AD262 AD311 AD332 AD492 AD512 AD622 AD632 AD642 AD662 BB45 BB48 CC02 CC04 CC05 CC12 EE12 FF01 4C084 AA19 MA02 MA63 NA05 ZA891 4C206 AA01 AA03 CA05 DB03 DB44 MA02 MA83 ZA89 4H006 AA01 AB12 BP10 KA14

Claims (9)

[Claims] [Claim 1] The following formula (1) (Wherein m represents an integer of 2 to 7 and n represents an integer of 2 to 3). 2. The alkyl polyglycol neopentanate of formula (1) according to claim 1, wherein m is 3 and n is 2. 3. A humectant comprising the alkyl polyglycol neopentanate of formula (1) according to claim 1. 4. A humectant comprising the alkyl polyglycol neopentanate of formula (1) according to claim 1, wherein m is 3 and n is 2. 5. An external preparation for skin containing the alkyl polypentane neopentanate of formula (1) according to claim 1. 6. An external preparation for skin containing the alkyl polyglycol neopentanate of formula (1) according to claim 1, wherein m is 3 and n is 2. 7. The external preparation for skin according to claim 5, further comprising a humectant. 8. The humectant is a polyhydric alcohol, an organic acid salt,
8. The external preparation for skin according to claim 7, which is one or more selected from the group consisting of mucopolysaccharides and plant extracts. 9. The external preparation for skin according to claim 7, wherein the humectant is a polyhydric alcohol.