JP6865527B2 - Composition - Google Patents

Description

The present invention relates to a composition containing amino acids and vitamins having excellent biosafety and stability.

Conventionally, health-promoting, nutritional, or cosmetological products containing amino acids and vitamins as active ingredients have been put on the market, but many of these amino acids and vitamins lack stability over time and are expensive. There was a problem in terms of industrial use. In order to solve these problems, compositions containing derivatives such as hydrochlorides of these amino acids and vitamins have been proposed (Patent Documents 1 to 4), but the derivatives of hydrochlorides are strongly acidic and therefore stable. There was a problem in terms of safety. Further, in the industrial treatment process, when the pH of the composition containing the derivative of the above-mentioned hydrochloride is adjusted with a pH adjuster or the like, there is a problem that a large amount of salt is generated.

Japanese Patent Application Laid-Open No. 60-04683 Japanese Unexamined Patent Publication No. 05-004921 Japanese Unexamined Patent Publication No. 11-092385 Japanese Unexamined Patent Publication No. 11-171793

From the above, it is an object of the present invention to improve safety, safety and usability in health-promoting, nutritional-supplementing or cosmetological compositions containing amino acids and vitamins as active ingredients.

The present invention is a composition containing a dehydrochlorinated product of an amino acid or vitamin hydrochloride.
The present invention is a composition containing a dehydrochlorinated product of an amino acid or vitamin hydrochloride and an acidic compound.

The present invention is a composition containing a dehydrochlorinated product of an amino acid or vitamin hydrochloride, and can provide a highly safe and stable composition for health promotion, nutritional supplementation or beauty. .. The present invention also provides a composition containing a dehydrochlorinated product of an amino acid or vitamin hydrochloride and an acidic compound, which is highly safe and stable and has excellent usability. Can be done.

Hereinafter, preferred embodiments of the present invention will be described in detail.
The present invention is a composition containing a dehydrochlorinated product of an amino acid or vitamin hydrochloride.
Examples of the amino acid hydrochloride include lysine or hydroxylysine hydrochloride, cysteine hydrochloride, ornithine hydrochloride, arginine hydrochloride, glucosamine hydrochloride and the like, and examples of the vitamin hydrochloride include thiamine hydrochloride and pyridoxin. Hydrochloride and the like can be mentioned.

In the present invention, as the method of dehydrochloric acid, for example, ion exchange can be used. Hydrochloric acid in an aqueous solution of an amino acid or vitamin hydrochloride is not particularly limited as long as it can be removed from the amino acid or vitamin, and examples thereof include an electrodialysis method using an ion exchange membrane and a replacement method using an ion exchange resin. Further, from the viewpoint of efficiency of dehydrochloric acid, a dehydrochloric acid method using an anion exchange membrane using an electrolytic reduction device can also be used.

In the method using ion exchange, deCling is performed by passing a solution of hydrochloride through a column packed with a strong basic anion exchange resin. The solution obtained here becomes a dehydrochlorinated aqueous solution.

Further, in the composition of the present invention, a dehydrochlorinated product of an amino acid or vitamin hydrochloride and an acidic compound can be used in combination. Examples of the acidic compound include ascorbic acid (vitamin C) or a derivative thereof (ascorbic acid glucoside, ethyl ascorbic acid (3-O-ethylascorbic acid, etc.)) used in products for health promotion, nutritional supplementation or beauty. , Ascorbic acid glyceride, etc.), arbutin, kodiic acid, salicylic acid, carboxyvinyl polymer, polyphenols and the like. When these compounds are used in combination with a strong acid component, the composition becomes unstable, but when used in combination with the dehydrochloric acid-treated product according to the present invention, a composition having excellent stability, safety and usability can be obtained.

In addition, the composition according to the invention is one or two selected from inorganic acids or salts thereof, organic acids or salts thereof, chelating agents, and plant, seaweed, animal-derived components, etc., in order to improve stability. Examples of the inorganic acids or salts thereof, which can contain seeds or more, include inorganic salts such as sulfite or a salt thereof, phosphoric acid or a salt thereof, and organic acids or salts thereof. , Citric acid or its salt, malic acid or its salt, tartaric acid or its salt, oxalic acid or its salt, lactic acid or its salt, sorbic acid or its salt, fumaric acid or its salt, phthalic acid or its salt and the like. .. Examples of the chelating agent include edetonic acid or its salt, ethylenediamine triacetic acid or its salt, gluconic acid or its salt, phytic acid or its salt, pyrophosphoric acid or its salt, polyphosphoric acid or its salt, metaphosphoric acid or its salt, And hydroxyethanediphosphonic acid or a salt thereof and the like.

Further, in the present invention, the inorganic acid salt may be any salt as long as it is a physiologically acceptable inorganic acid salt (potassium, sodium, calcium, magnesium, iron, zinc, etc.). For example, examples of the above-mentioned sulfite include sodium hydrogen sulfite, sodium pyrosulfite or sodium sulfite, potassium hydrogen sulfite, potassium sulfite, calcium hydrogen sulfite, calcium sulfite, magnesium hydrogen sulfite, magnesium sulfite and the like. It is not limited to. Similarly, the phosphate may be any salt as long as it is a physiologically acceptable salt (potassium, sodium, calcium, magnesium, iron, zinc, etc.).

The organic acid salt used in the present invention may be any salt as long as it is a physiologically acceptable salt (potassium, sodium, calcium, magnesium, iron, zinc, etc.). For example, examples of the citrate include, but are not limited to, sodium citrate, disodium citrate, trisodium citrate, potassium citrate, dipotassium citrate, and tripotassium citrate. .. Similarly, the above malate, tartrate, oxalate, lactate, sorbate, pyruvate, fumarate, and phthalate are also physiologically acceptable salts (potassium, sodium, Any salt may be used as long as it is calcium, magnesium, iron, zinc, etc.).

In addition, examples of components derived from natural products (plants, seaweeds, animals) include the following. For example, rice extract, rice bran extract, gentiana extract, aloe extract, amamo extract, chamomile extract, soybean extract, coral grass extract, white potato extract, purple orchid root extract, eggplant extract, paudalco Extract, daily extract, carrot extract, green algae extract, brown algae extract, red algae extract, peach extract, honeybee extract, fig extract, lotus seed extract, hagoromogusa extract, black bean extract, mango Extract, Mangostin extract, Charimoya extract, Strawberry extract, Hibiscus extract, Royal jelly extract, Soy milk extract, Takenoko extract, Benibana extract, Banpeille extract, Licograss extract, Sweet potato extract, Apple extract , Kiwi extract, Hatomugi extract, Perilla extract, Rose extract, Bergamot extract, Sansho extract, Rice leaf extract, Murasakikibu extract, Guava leaf extract, White asparagus extract, Dokudami extract , Tea extracts and their hydrolysates or fermented products.

The pH of the composition prepared as described above is generally adjusted to the range of pH 5.0 to 8.0, and more preferably adjusted to pH 6.0 to 7.0.

The composition according to the present invention is useful as a composition for health promotion, nutritional supplementation or cosmetology. Beverages such as beauty beverages, energy drinks, sports drinks, near water, vitamin beverages, mineral beverages, alcoholic beverages; various soups (including powdered soups), as composition for health promotion, nutritional supplementation and beauty. Foods such as dairy products, jellies, candy, tablets, gums, etc .; can be blended in tablets, liquids, granular or jelly-like health foods / beverages, etc., but the present invention is not limited to this, and is taken orally. It can be blended in foods and drinks that can be produced. The composition according to the present invention can also be used as an external composition, for example, milky lotion, cream, lotion, essence, facial mask, lipstick, foundation, liquid foundation, make-up press powder, blusher, white powder, face wash. Materials, body shampoos, hair shampoos, soaps, etc., and hair restorers, bathing agents, etc. are also mentioned, but are not limited thereto.

The blending amount of the extract of the present invention in the oral composition is preferably in the range of 0.1 to 15% by weight as the solid content of the extract. The blending amount in the external composition is preferably 0.001 to 10.0% by weight as the solid content of the extract.

In addition to the essential components, the composition includes components used in oral compositions and external compositions, such as oily components, surfactants (synthetic and natural products), moisturizers, thickeners, and preservatives. -A bactericide, a powder component, an ultraviolet absorber, an antioxidant, a pigment, a fragrance, etc. can be appropriately blended as needed. In addition, other physiologically active ingredients may be combined and blended as long as the effectiveness and characteristics of the extract are not impaired.

Here, examples of the oily component include bergamot oil, olive oil, jojoba oil, paraffin oil, soybean oil, rice oil, rice bran oil, rice germ oil, palm oil, chamomile oil, palm oil, cacao oil, meadowfoam oil, and rose. Plant-derived fats and oils such as hip oil, lanbender oil, sheer butter, tea tree oil, avocado oil, macadamia nut oil, and plant-derived squalane; animal-derived fats and oils such as mink oil and turtle oil; , Lanorin and other waxes; liquid paraffin, vaseline, paraffin wax, squalane and other hydrocarbons; myristic acid, palmitic acid, stearic acid, oleic acid, isostearic acid, eicosenoic acid and other fatty acids; lauryl alcohol, cetanol, stearyl Higher alcohols such as alcohols; synthetic esters such as isopropyl myristate, isopropyl palmitate, butyl oleate, 2-ethylhexyl glyceride, higher fatty acid octyldodecyl (octyldodecyl stearate, etc.), synthetic triglycerides and the like can be mentioned.

Examples of the surfactant include polyoxyethylene alkyl ether, polyoxyethylene fatty acid ester, polyoxyethylene sorbitan fatty acid ester, glycerin fatty acid ester, polyglycerin fatty acid ester, polyoxyethylene glycerin fatty acid ester, polyoxyethylene hydrogenated castor oil, and poly. Nonionic surfactants such as oxyethylene sorbitol fatty acid esters; fatty acid salts, alkyl sulfates, alkylbenzene sulfonates, polyoxyethylene alkyl ether sulfates, polyoxyethylene fatty amine sulfates, polyoxyethylene alkylphenyl ether sulfates, Anionic surfactants such as polyoxyethylene alkyl ether phosphates, α-sulfonated fatty acid alkyl ester salts, polyoxyethylene alkyl phenyl ether phosphates; quaternary ammonium salts, primary to tertiary fatty amine salts, tris. Cationic surfactants such as alkylbenzylammonium salt, alkylpyridinium salt, 2-alkyl-1-alkyl-1-hydroxyethylimidazolinium salt, N, N-dialkylmorphonium salt, polyethylene polyamine fatty acid amide salt; N, N-dimethyl-N-alkyl-N-carboxymethylammoniobetaine, N, N, N-trialkyl-N-alkylene ammoniocarboxybetaine, N-acylamide propyl-N', N'-dimethyl-N'- An amphoteric surfactant such as β-hydroxypropylammoniosulfobetaine can be used.

Examples of emulsifiers or emulsifying aids include stevia derivatives such as enzyme-treated stevia, saponins or derivatives thereof, casein or salts thereof (sodium, etc.), sugar-protein complexes, sucrose or esters thereof, lactose, and water-soluble soybeans. Polysaccharide, complex of soybean-derived protein and polysaccharide, lanolin or its derivative, cholesterol, stevia derivative (stevia enzyme treated product, etc.), silicate (aluminum, magnesium, etc.), carbonate (calcium, sodium, etc.), saponin and its Derivatives, lecithin and its derivatives (hydrogenated lecithin, etc.), lactic acid bacteria fermented rice, lactic acid bacteria fermented sprouted rice, lactic acid bacteria fermented grains (wheat, beans, miscellaneous grains, etc.) and the like can also be blended.

Examples of the moisturizing agent include glycerin, propylene glycol, dipropylene glycol, 1,3-butylene glycol, polyethylene glycol, sorbitol, xylitol, sodium pyrrolidone carboxylate and the like, and saccharides such as trehalose and mucopolysaccharides (for example, hyalurone). Acids and their derivatives, chondroitin and its derivatives, heparin and its derivatives, etc.), elastin and its derivatives, collagen and its derivatives, NMF-related substances, lactic acid, urea, higher fatty acids octyldodecyl, seaweed extract, silane roots (white) Examples include extracts, various amino acids and their derivatives.

Examples of the thickener include ingredients derived from brown algae such as alginic acid, agar, carrageenan, and fucoidan, green algae or red algae; silane root (white and) extract; pectin, locust bean gum, aloe polysaccharide, alkaligenes-producing polysaccharide and the like. Polysaccharides; gums such as xanthan gum, tragant gum, guar gum; cellulose derivatives such as carboxymethyl cellulose and hydroxyethyl cellulose; synthetic polymers such as polyvinyl alcohol, polyvinyl pyrrolidone, carboxyvinyl polymer, alginic acid / methacrylic acid copolymer; hyaluronic acid And derivatives thereof; examples thereof include polyglutamic acid and derivatives thereof.

Examples of preservatives and bactericides include urea; paraoxybenzoic acid esters such as methyl paraoxybenzoate, ethyl paraoxybenzoate, propyl paraoxybenzoate, and butyl paraoxybenzoate; phenoxyethanol, dichlorophenol, hexachlorophene, chlorhexidine hydrochloride, and benza chloride. Plant-derived ethanol such as luconium, salicylic acid, ethanol, undecyleneic acid, phenols, jamar (imidazodeinylurea), propanediol, 1,2-pentanediol, various essential oils, bark dry distillate, radish fermented liquid, sugar cane Alternatively, there are 1,3-butylene glycol and the like.

Examples of powder components include cericite, titanium oxide, talc, kaolin, bentonite, zinc oxide, magnesium carbonate, magnesium oxide, zirconium oxide, barium sulfate, silicic anhydride, mica, nylon powder, polyethylene powder, silk powder, and cellulose. There are powders of type, grains (rice, wheat, corn, talc, etc.), beans (soybeans, talc, etc.).

Examples of the ultraviolet absorber include ethyl paraaminobenzoate, ethylhexyl paradimethylaminobenzoate, amyl salicylate and its derivatives, 2-ethylhexyl paramethoxycinnamate, octyl silicate, oxybenzone, 2,4-dihydroxybenzophenone, 2-hydroxy-4. -Methoxybenzophenone-5-sulfonate, 4-tershally butyl-4-methoxybenzoylmethane, 2- (2-hydroxy-5-methylphenyl) benzotriazole, urocanic acid, ethyl urocanate, aloe extract, etc. ..

Antioxidants include, for example, butylhydroxyanisole, butylhydroxytoluene, propyl gallate, vitamin E and derivatives thereof (for example, vitamin E nicotinate, vitamin E linoleate, etc.).

Whitening agents include t-cycloamino acid derivatives, kodiic acid and its derivatives, ascorbic acid and its derivatives, hydroquinone or its derivatives, ellagic acid and its derivatives, nicotinic acid and its derivatives, resorcinol derivatives, tranexamic acid and its derivatives, 4 -Potasium methoxysalicylic acid, magnolignan (5,5'-dipropyl-biphenyl-2,2'-diol), hydroxybenzoic acid and its derivatives, vitamin E and its derivatives, α-hydroxy acid, AMP (adenosine monophosphate) , Adenosine monophosphate), and these may be blended alone or in combination of two or more.

Examples of the ascorbic acid derivative include ascorbic acid esters such as ascorbic acid monobutyrate, ascorbic acid monocaplate, ascorbic acid monopalmitate, and ascorbic acid dibutyrate, ascorbic acid ethers, and ascorbic acid sugar derivatives such as ascorbic acid glucoside. However, examples of the ascorbic acid derivative include L-ascorbic acid-2-phosphate ester sodium, L-ascorbic acid-2-phosphate ester magnesium, L-ascorbic acid-2-sulfate sodium ester, and L-ascorbic acid-2. -Ascorbic acid ester salts such as magnesium sulfate, L-ascorbic acid-2-glucoside, L-ascorbic acid-5-glucoside, ascorbic acidcopheryl maleic acid, ascorbic acidcopheryl phosphate K, myristyl 3-glyceryl ascorbic acid, caprylyl Ascorbic acid sugar derivatives such as 2-glyceryl ascorbic acid, 6-position acylated products of these ascorbic acid sugar derivatives (acyl groups are hexanoyl group, octanoyl group, decanoyle group, etc.), L-ascorbic acid tetraisopalmitic acid ester, L- L-ascorbic acid tetrafatty acid esters such as ascorbic acid tetralauric acid ester, 3-O-ethylascorbic acid, L-ascorbic acid-2-phosphate-6-O-palmitate sodium, glyceryl ascorbic acid or acylation thereof Derivatives, glycerin ascorbic acid derivatives such as bisglyceryl ascorbic acid, aminopropyl L-ascorbic acid phosphate, hyaluronic acid derivatives of L-ascorbic acid, 3-OD lactose-L-ascorbic acid, isostearyl ascorbic acid, etc. However, as the hydroquinone derivative, albutin (hydroquinone-β-D-glucopyranoside), α-arbutin (hydroquinone-α-D-glucopyranoside) and the like are used, and as the tranexamic acid derivative, a tranexamic acid ester (for example, tranexamic acid lauryl ester, etc.) Examples thereof include tranexamic acid hexadecyl ester, tranexamic acid cetyl ester or a salt thereof), an amide form of tranexamic acid (for example, methylamide tranexamic acid), and examples of the resorcinol derivative include 4-n-butylresorcinol and 4-isoamylresorsinol. As the 2,5-dihydroxybenzoic acid derivative, for example, 2,5-diacetoxybenzoic acid, 2-acetoxy-5-hydroxybenzoic acid, 2-hydroxy-5-propioniluo, etc. Xybenzoic acid and the like, nicotinic acid derivatives include, for example, nicotinamide, benzyl nicotinate and the like, and α-hydroxy acids include, for example, lactic acid, malic acid, succinic acid, citric acid, α-hydroxyoctanoic acid and the like. ..

Next, the present invention will be described in more detail with reference to Production Examples, Formulation Examples, and Test Examples, but the present invention is not limited thereto. In the following, all parts mean parts by weight, and% means all parts by weight.

Production example 1. Preparation of lysine 100 g of lysine hydrochloride was dissolved in 900 g of purified water. This aqueous hydrochloride solution was passed through a strong basic anion exchange resin column to perform dehydrochlorination treatment. This liquid was concentrated to dryness to obtain 10 g of lysine.

Production example 2. Preparation of Glucosamine 100 g of glucosamine hydrochloride was dissolved in 900 g of purified water. This aqueous hydrochloride solution was passed through a strong basic anion exchange resin column to perform dehydrochlorination treatment. This liquid was concentrated to dryness to obtain 72 g of glucosamine.

Production example 3. Preparation of thiamine 100 g of thiamine hydrochloride was dissolved in 900 g of purified water. This aqueous hydrochloride solution was passed through a strong basic anion exchange resin column to perform dehydrochlorination treatment. This liquid was concentrated to dryness to obtain 43 g of thiamine.

Production example 4. Preparation of pyridoxine 100 g of pyridoxine hydrochloride was dissolved in 900 g of purified water. This aqueous hydrochloride solution was passed through a strong basic anion exchange resin column to perform dehydrochlorination treatment. This solution was concentrated to dryness to obtain 6 g of pyridoxine.

Prescription example 1. Beverage [Ingredients] Part Production Example 1 Compound 3.0
Collagen 5.0
Citric acid 0.1
Sweetener (sucrose) 0.01
Ascorbic acid 0.01
Amount of purified water totaling 100 parts

Prescription example 2. Beverage A beverage was obtained in the same manner as in Formulation 1, except that 3.0 parts of the compound of Production Example 2 was used instead of the compound of Production Example 1 contained in Formulation Example 1.

Prescription example 3. Beverage A beverage was obtained in the same manner as in Formulation 1, except that 3.0 parts of the compound of Production Example 3 was used instead of the compound of Production Example 1 contained in Formulation Example 1.

Prescription example 4. Beverage A beverage was obtained in the same manner as in Formulation 1, except that 3.0 parts of the compound of Production Example 4 was used instead of the compound of Production Example 1 contained in Formulation Example 1.

Prescription example 5. Tablet [Ingredients] Part Compound 2.0 of Production Example 1
Compound 2.0 of Production Example 2
Compound 2.0 of Production Example 3
Compound 2.0 of Production Example 4
Ascorbic acid 5.0
Fatty acid ester 10.0
Calcium lactate 20.0
Lactose 30.0
After mixing each component by weight, pressure molding was performed to obtain a tablet.

Prescription example 6. Toner [A component] Part Olive oil 1.0
Polyoxyethylene (5.5) cetyl alcohol 5.0
Butylparaben 0.1
[B component]
Compound 2.0 of Production Example 1
Ascorbic acid 2.0
Ethanol 5.0
Glycerin 5.0
1,3-butylene glycol 5.0
Sodium metabisulfite 2.0
Appropriate amount of citric acid Trisodium citrate 0.4
Potassium hydroxide Appropriate amount Purified water 100 parts in total [C component]
Appropriate amount of fragrance After heating each of the A component and the B component to 80 ° C. or higher, the B component was added to the A component and stirred, and further homogenized with hiscotron (5000 rpm) for 2 minutes. After cooling this to 50 ° C., the C component was added, stirred and mixed, and further cooled to 30 ° C. or lower to obtain a lotion.

Prescription example 2. Toner A lotion was obtained in the same manner as in Formulation 1, except that 1.0 part of the compound of Production Example 2 was used instead of the compound of Production Example 1 contained in the component B of Formulation Example 1.

Prescription example 3. Toner A lotion was obtained in the same manner as in Formulation 1, except that 1.0 part of the compound of Production Example 3 was used instead of the compound of Production Example 1 contained in the component B of Formulation Example 1.

Prescription example 4. Toner A lotion was obtained in the same manner as in Formulation 1, except that 1.0 part of the compound of Production Example 4 was used instead of the compound of Production Example 1 contained in the component B of Formulation Example 1.

Prescription example 5. Emulsion [Component A] Part Liquid paraffin 6.0
Hexalan 4.0
Jojoba oil 1.0
Polyoxyethylene (20) sorbitan monostearate 1.0
Lipophilic glyceryl stearate 1.0
Soy lecithin 1.5
Lactic acid bacteria fermented rice 2.0
[B component]
Compound 2.0 of Production Example 1
Ascorbic acid 2.0
Potassium hydroxide 0.5
Glycerin 3.0
1,3-butylene glycol 2.0
Carboxymethyl cellulose 0.3
Sodium citrate 0.1
Amount of purified water totaling 100 parts [C component]
Appropriate amount of fragrance The above components A and B were heated to 80 ° C. or higher, and then stirred and mixed. After cooling this to 50 ° C., component C was added and further stirred and mixed to obtain a milky lotion.

Prescription example 6. Emulsion Emulsion was obtained in the same manner as in Formulation 5, except that 2.0 parts of L-ascorbic acid-2-glucoside and 0.5 part of potassium hydroxide were used instead of ascorbic acid in the B component of Formulation Example 5.

Prescription example 7. Emulsion Emulsion was obtained in the same manner as in Formulation 5 except that 3.0 parts of arbutin was used instead of ascorbic acid in the B component of Formulation Example 5.

Prescription example 8. Emulsion Emulsion was obtained in the same manner as in Formulation 5 except that 3.0 parts of kojic acid was used instead of ascorbic acid in the B component of Formulation Example 5.

Prescription example 9. Emulsion Emulsion was obtained in the same manner as in Formulation 5, except that 2.0 parts of 3-O-ethylascorbic acid was used instead of ascorbic acid in the B component of Formulation Example 5.

Prescription example 10. Emulsion Emulsion was obtained in the same manner as in Formulation 5 except that 0.3 part of salicylic acid was used instead of ascorbic acid in the B component of Formulation Example 5.

Prescription example 11. Emulsion [A component] Part Squalene 3.0
Behenyl alcohol 3.0
Hexalan 4.0
Jojoba oil 1.0
Polyoxyethylene (20) sorbitan monostearate 1.0
Glycerin fatty acid ester 1.0
Soy lecithin 1.5
[B component]
Compound 0.5 of Production Example 2
Compound 0.5 of Production Example 4
L-ascorbic acid-2-glucoside 2.0
Potassium hydroxide 0.5
Dipotassium glycyrrhizinate 0.1
Glycerin 3.0
1,3-butylene glycol 2.0
Sodium metabisulfite 0.01
Amount of purified water totaling 100 parts

Prescription example 12. Lotion [ingredient] part Compound 1.0 of Production Example 1
Compound 1.0 of Production Example 3
Ethanol 10.0
Glycerin 3.0
1,3-butylene glycol 2.0
Methylparaben 0.2
Citric acid 0.1
Sodium citrate 0.3
Carboxyvinyl polymer 0.1
Catechin 0.1
Xanthan gum 0.1
Perfume Appropriate amount Potassium hydroxide Appropriate amount Purified water 100 parts in total The above components were mixed to obtain a lotion.

Test example 1. Primary Skin Irritation Suppression Test The safety of the compounds according to Production Examples 1 to 4 of the present invention was evaluated by the primary skin irritation suppression test.
[Test method]
A test site was provided on the medial side of each upper arm for 5 subjects (men and women aged 20 to 60 years), and the amount of erythema in the test area of each subject was measured as an initial value after washing (Mexameter®). Measured by MX18, Courage + (manufactured by Khazaka). Then, the test part was patched with an aqueous solution containing the compounds of Production Examples 1 to 4 (final concentration: 2.0%) for 4 hours. After the occlusion patch was completed, the test part was washed with water, and 3 hours later, the amount of erythema in the test part of each subject was measured by the above measuring device, and the value obtained by subtracting the value immediately after the treatment from the initial value was used as the primary stimulation suppression amount for 5 persons. The average value of the subjects was calculated. Further, as a control, purified water was used instead of Production Examples 1 to 4, and the same operation as described above was performed. Further, as comparison targets, the compounds of Production Examples 1 to 4 before the treatment with hydrochloric acid were used as Comparative Examples 1 to 4, respectively, and the same test was conducted.

The results of Test Example 1 are shown in Table 1.
[Table 1]

As shown in Table 1, it was confirmed that the compound according to the present invention was superior in biosafety as compared with the compound of Comparative Example.

Test Example 2-1. Stability test The combined composition containing the compound according to the present invention and the acidic compound was evaluated by a visual test of the change over time in coloring.
[Test method]
The following mixture was prepared (pH 6.5) and the coloring was visually confirmed every week for 4 weeks under the temperature conditions of 4 ° C., 20 ° C. and 40 ° C. In addition, the following "part" shall indicate weight%.
(mixture)
[1] Compound (1) of Production Example 1, Compound (2) of Production Example 2, Compound (3) of Production Example 3 or Compound (4) of Production Example 4: 1.0 part [2] Acid compound: Ascorbic acid Acid (A), ascorbic acid glucoside (B), 3-O-ethylascorbic acid (C): 2.0 parts [3] 1,3-butylene glycol: 5.0 parts [4] Preservative (methylparaben): 0.2 parts [5] Purified water: 82 parts

The results of Test Example 2 are shown in Tables 2-1 (A) to (C).
[Table 2-1 (A)]

[Table 2-1 (B)]

[Table 2-1 (C)]

As shown in Tables 2-1 (A) to (C), even when the compound according to Production Examples 1 to 4 according to the present invention and the acidic compound are used in combination, coloring is suppressed, and the composition according to the present invention is produced. It was confirmed that it was excellent in terms of stability.

Test Example 2-2. Stability test [Test method]
The following mixture was prepared (pH 6.5) and the coloring was visually confirmed every week for 4 weeks under the temperature conditions of 4 ° C., 20 ° C. and 40 ° C. In addition, the following "part" shall indicate weight%.
(mixture)
[1] Compound (1) of Production Example 1, Compound (2) of Production Example 2, Compound (3) of Production Example 3 or Compound (4) of Production Example 4: 1.0 part [2] Acid compound: Ascorbic acid Acid (A), ascorbic acid glucoside (B) or 3-O-ethylascorbic acid (C): 2.0 parts [3] Sodium metabisulfite: 0.2 parts [4] Citric acid: Appropriate amount [5] Citric acid Sodium: 0.4 parts [6] 1,3-butylene glycol: 5.0 parts [7] Preservative (methylparaben): 0.2 parts [8] Purified water: 100 parts in total

The results of Test Example 2-2 are shown in Tables 2-2 (A) to (C).
[Table 2-2 (A)]

[Table 2-2 (B)]

[Table 2-2 (C)]

As shown in Tables 2-2 (A) to (C), the compounds according to Production Examples 1 to 4 according to the present invention and the acidic compound are further added with a stability improver (sodium pyrosulfite, sodium citrate). It was confirmed that when used in combination, coloring was remarkably suppressed, and the composition according to the present invention was excellent in terms of stability.

Test example 3. Evaluation test of usability In Test Example 3, the following samples (1) to (7) of the present invention and comparative samples (1) and (2) were evaluated for usability. In addition, the following "part" shall indicate weight%.
(1) Sample 1 of the present invention
[Ingredients] Part Ethanol 2.0
Glycerin 5.0
Methylparaben 0.1
Compound 2.0 of Production Example 1
Ascorbic acid glucoside 2.0
Sodium citrate 0.6
Amount of purified water totaling 100 parts (2) Sample 2 of the present invention
An essence in which 2.0 parts of the compound of Production Example 2 is blended in place of the compound of Production Example 1 in the sample 1 of the present invention.
(3) Sample 3 of the present invention
An essence containing 2.0 parts of the compound of Production Example 3 in place of the compound of Production Example 1 in the sample 1 of the present invention.
(4) Sample of the present invention 4.
An essence in which 2.0 parts of the compound of Production Example 4 is blended in place of the compound of Production Example 1 in the sample 1 of the present invention.
(5) Sample 5 of the present invention
An essence containing 2.0 parts of ascorbic acid in place of ascorbic acid glucoside in the sample 1 of the present invention.
(6) Sample 6 of the present invention
An essence containing 2.0 parts of 3-O-ethylascorbic acid in place of ascorbic acid glucoside in Sample 1 of the present invention.
(7) Sample 7 of the present invention
An essence containing 3.0 parts of arbutin in place of ascorbic acid glucoside in Sample 1 of the present invention.
(8) Comparative sample 1
An essence that does not contain the compound of Production Example 1 in the composition of the sample 1 of the present invention.
[Test method]
Twenty-one randomly selected men and women aged 25 to 60 years were divided into 7 groups, and each group of subjects was given one of Samples 1 to 7 of the present invention and Comparative Sample 1 on the left and right cheeks, respectively. The feeling of use when the emulsion of the example of the present invention or the emulsion of the comparative example was applied to the cheeks twice a day (morning and evening) for one month was evaluated. The feeling of use is 5: very good, based on the feel in the hand (a), the elongation at the time of application (b), the smoothness at the time of application (c), and the feel after application (d). Good, 3: Normal, 2: Slightly bad, 1: Bad, respectively, and the total evaluation values of the subjects of each group are shown for the sample of the present invention, and the subjects of each group for the comparative sample. The value obtained by averaging the total evaluation values is shown.

The results of Test Example 3 are shown in Table 3.
[Table 3]

As shown in Table 3, it was confirmed that a composition for external use having an excellent usability can be obtained even when the compounds of Production Examples 1 to 4 according to the present invention and the acidic compound are used in combination.

Claims (2)

Vitamin B6 desalted acid-treated product which contained the face or scalp cosmetic composition hydrochloride (excluding whitening composition). Vitamin B6 desalted acid-treated product of the hydrochloride salt and ascorbic acid or a cosmetic composition comprising the derivative and sodium pyrosulfite (excluding whitening composition).