KR0174165B1 - A method for preparing 3-aminopropane phosphoric acid and cosmetic compositions containing it or its derivatives - Google Patents

Abstract

The present invention relates to 3-aminopropane phosphoric acid, which is capable of preventing skin wrinkles by promoting proliferation and collagen synthesis of fibroblasts while having no irritation to the skin, and having excellent stability of the substance itself, Amino-1-propanol and phosphorus oxychloride in an equivalent ratio of 1: 1 to 1.3 in the presence of an organic solvent to produce a 3-aminopropane phosphoric acid represented by the formula (I) The reaction is carried out at a temperature of 5 ° C for 1 hour, and then the reaction is hydrolyzed in an acid catalyst and crystallized with alcohol.

[Chemical Formula 1]

(I)

The process for producing 3-aminopropane phosphoric acid according to the present invention uses low-cost phosphorus oxychloride, the reaction is economical in two steps, and can be usefully used in industrial methods.

The present invention also relates to a cosmetic composition comprising 3-aminopropane phosphoric acid or a salt thereof as an active ingredient. The cosmetic composition according to the present invention improves water retention ability in the skin, And the effect of effectively reducing the aging of the skin is excellent.

Description

Process for producing 3-aminopropane phosphoric acid and cosmetic composition containing the same

The present invention relates to a process for producing 3-aminopropane phosphoric acid represented by the following structural formula (I) and a cosmetic composition containing the same. More particularly, the present invention relates to a process for producing 3-amino-1-propanol, which comprises the steps of reacting 3-amino-1-propanol with phosphorus oxychloride at a low temperature and hydrolyzing the product under an acid catalyst, Aminopropane phosphoric acid or a salt thereof as an active ingredient to improve the moisture retention ability of the skin and to increase the recovery power against deformation and skin strength to effectively reduce the aging of the skin. .

(I)

The function of cosmetics is to clean, brighten, and keep skin and hair healthy. In particular, a number of studies have been conducted to prevent the formation of fine wrinkles in skin by the activity of skin cells, and many materials have been developed and used. Examples of such substances include vitamins such as retinol and ascorbic acid, proteins extracted from various animals and plants, flavonoids, amino acids, epidermal growth factors, and alpha hydroxy acids such as citric acid. . However, most of these ingredients are known to be extremely unstable in themselves or to cause some irritation to the skin.

Thus, researches on new cosmetic raw materials that can stimulate cell growth and collagen synthesis of the dermis are being actively carried out, while there is no irritation to the skin and the substance itself is stable, so that it is easy to apply to cosmetics. Amino-butyric acid (GABA: H ₂ NCH ₂ CH ₂ CH ₂ COOH) has been already developed and used as such a substance. This material is a taurine-like compound with a structure similar to that of taurine (H ₂ NCH ₂ CH ₂ SO ₃ H) (MARTINDAL, The Extra Pharmacopeia, 29th, The Pharmaceutical Press), well known as a treatment for diseases related to cardiac blood flow Taurine-like compounds are disclosed in JP-A-3-63211, JP-A-2-62810, JP-A-1-22810, JP-A-62-19511, JP-A-62-207312 , Japanese Patent Application Laid-Open No. 60-199810, Japanese Laid-Open Patent Application No. 62-7162, Japanese Laid-Open Patent Application No. 58-26726, etc., which are known to inhibit skin aging and have a whitening function. However, GABA has disadvantages in that it does not exhibit satisfactory skin aging inhibiting action in the actual cosmetic base.

Accordingly, the present inventors have intensively studied to provide a cosmetic composition which can prevent the formation of fine wrinkles and effectively reduce the aging of the skin. The present invention provides a cosmetic composition which has no irritation to the skin and is easy to apply to cosmetics, And to develop a new raw material capable of promoting collagen synthesis of the dermis. As a result, the carboxyl group (-COOH) of inhibiting the skin aging and whitening effects are excellent γ- aminobutyric acid _{(H 2 N-CH 2 CH} 2 CH 2 -COOH), a sulfonic acid group (-O-SO ₂ H) of taurine (H ₂ N-CH ₂ CH ₂ CH ₂ -O-PO ₃ H) having a structure similar to that of the phosphorylated phosphoryl group (-O-PO ₃ H) The above object can be achieved and the present invention is focused on.

Meanwhile, as a conventional method for synthesizing 3-aminopropane phosphoric acid, 3-amino-1-propanol and polyphosphoric acid are reacted at 150-250 DEG C under reduced pressure for 30-40 hours, and then calcium hydroxide or barium hydroxide is used , Respectively, and then neutralizing the salt with sulfuric acid is known. However, this method requires a long reaction time (150 to 250 ° C., 30 to 40 hours) at a high temperature, resulting in high energy consumption, low yield, and removal of excess calcium phosphate or barium salt It is necessary to perform a complicated purification step.

In another synthetic method, 3-formamidopropanol and cyanoethylphosphoric acid are coupled using dicyclohexylcarbodiimide (DCC) and neutralized with barium hydroxide Then, it is hydrolyzed again with sodium hydroxide to produce a barium salt, which is then passed through a cation exchange resin (amberlite IR 120 (H ⁺ )) to convert it to formamidopropyl phosphate and then hydrolyzed with hydrochloric acid to obtain 3- Methods for producing phosphoric acid are also known (Chem. Pharm, Bull., 1969, 17 (1), 202-206).

Further, as shown in Reaction Scheme 1 below, dichlorophosphoric acid phenylester was stirred at room temperature and purified by silica gel column to obtain a compound of formula (III), which was hydrolyzed with hydrochloric acid, and platinum oxide And a method for producing 3-aminopropane phosphoric acid using a hydrogen gas catalyst are also known (J. Med. Chem., 1994, 37, 3986-3993).

However, the methods by these documents have a low production yield of about 38% and complicate the process. In particular, J. Med. Chem is uneconomical because it uses expensive platinum oxide as a catalyst and has a problem that it is difficult to apply it to mass production because a special device for deprotection reaction of phenyl ester group is required under hydrogen gas and platinum oxide catalyst.

That is, the conventional methods for producing 3-aminopropane phosphoric acid are not only economical but also unsuitable as industrial methods because expensive reagents are used, complex purification steps are required, and yields are low.

Accordingly, the present inventors have conducted studies to provide a method for producing 3-aminopropane phosphoric acid at a high yield by a simple process without using an expensive reagent. As a result, it has been found that phosphorus oxychloride, which can be purchased at low cost, 3-aminopropane phosphoric acid can be prepared using the above-mentioned method, and the present invention has been completed.

Accordingly, an object of the present invention is to provide a process for producing 3-aminopropane phosphoric acid represented by the following structural formula (I).

(I)

Another object of the present invention is to provide a cosmetic composition which can effectively prevent the aging of skin by preventing the formation of fine wrinkles by containing 3-aminopropane phosphoric acid or its salt synthesized by such a production method as an active ingredient .

The above object can be attained by reacting 3-amino-1-propanol with phosphorus oxychloride in an organic solvent. More specifically, the process for preparing 3-aminopropane phosphoric acid according to the present invention comprises reacting 3-amino- Propanol and phosphorus oxychloride are reacted in the presence of an organic solvent at an equivalent ratio of 1: 1 to 1.3 at a temperature of 0 to 5 ° C for 1 hour and then hydrolyzed with an acid catalyst and crystallized with alcohol.

The cosmetic composition according to the present invention is characterized by containing 3-aminopropane phosphoric acid or its salt obtained by the above-described production method in an amount of 0.001 to 20% by weight based on the total weight of the composition.

The process for producing 3-aminopropane phosphoric acid according to the present invention comprises:

(A) reacting 3-amino-1-propanol with phosphorus oxychloride in an equivalent ratio of 1: 1 to 1.3 in the presence of an organic solvent at a temperature of 0 to 5 DEG C for about 1 hour;

(B) filtering the reaction solution to obtain a filtrate, and then hydrolyzing the filtrate under reduced pressure and concentration; And

(C) Crystallization with alcohol

And a control unit.

The preparation process according to the invention can be schematically illustrated by the following scheme:

Amino-1-propanol and phosphorus oxychloride are reacted in the presence of an organic solvent at a temperature of 0 to 5 [deg.] C For about 1 hour to produce 2,6-oxa-cyclohexylphosphoryl chloride represented by the formula (V); The filtrate obtained by filtration of the reaction solution is concentrated, and water and an acid catalyst are added thereto. The mixture is heated to a temperature of about 70 to 90 캜 and refluxed for 1 to 3 hours, preferably 2 hours. After cooling again to room temperature, Neutralizing the acid remaining with triethylamine; And slowly dropping the alcohol to crystallize 3-propanaminophosphoric acid.

In the production process according to the present invention, it is preferable that 3-amino-1-propanol and phosphorus oxychloride are reacted at an equivalent ratio of 1: 1 to 1.3. If the equivalent ratio is less than 1: 1, the desired product can not be obtained. If the equivalent ratio is 1: 1.3 or more, excessive by-products are produced in addition to the desired product.

When 3-aminopropane phosphoric acid is prepared by the above-mentioned method, more than 95% of an intermediate in which 3-amino-1-propanol and phosphorus oxychloride are bound at a ratio of 1: 1 is produced, and 3-amino-1-propanol and phosphorus oxychloride This by-product combined with 2: 1 is produced in 1 to 2% or less. However, the above-mentioned by-products can be easily separated by using chromatography or by using a difference in solubility in an alcohol solvent. In particular, when two chlorine atoms of three chlorine atoms in a phosphorus oxychloride molecule are replaced by two functional groups of 3-amino-1-propanol, that is, 2,6-oxa-cyclohexylphosphoryl chloride which is cyclized by substitution by a hydroxyl group and an amine group And the remaining one chlorine atom is left unchanged because the reactivity is decreased at a low temperature of 5 ° C or lower. This is because the chlorine atom of 2,6-oxa-cyclohexylphosphoryl chloride is not easily substituted with 3-amino-1-propanol in a stable anhydrous inert solvent at low temperatures. Accordingly, the production method of the present invention is carried out at an equivalent ratio of 1: 1.0 to 1.3 at a temperature of 0 to 5 ° C for about 1 hour, so that 3-amino-1-propanol And phosphorus oxychloride in a ratio of 2: 1 or more can be prevented. In particular, since a step of introducing an ester group or an amide group to protect one chlorine atom in phosphorus oxychloride is not necessary, There is an advantage that it can be reduced.

As the organic solvent used in the present invention, inert solvents such as dichloromethane, tetrahydrofuran, ethyl acetate, acetonitrile, chloroform, ethyl ether and the like can be used. Also, in order to obtain 3-aminopropane phosphoric acid in high yield, it is preferable to carry out the reaction under anhydrous condition in the presence of an inert gas such as nitrogen gas or argon gas.

Amino-1-propanol is substituted with phosphorus oxychloride to increase the production of by-products, and the reaction is difficult to proceed because the solubility of the reactant is lowered at a temperature lower than 0 ° C. Since the content of the reactant is increased and the reaction yield is lowered, a temperature in the range of 0 to 5 ° C is preferable.

The acid catalyst used in the process for producing 3-aminopropane phosphoric acid of the present invention is not particularly limited, and for example, hydrochloric acid, sulfuric acid or acetic acid can be used. The acid catalyst is added in an amount of 5.0 to 10.0 mol%, preferably 5.0 to 7.0 mol%, based on 2,6-oxa-cyclohexylphosphoryl chloride, which is a compound of the structural formula (V) %, The total yield is decreased. When the amount is more than 10 mol%, discoloration occurs in the reaction and the final product can be colored.

In the above-described production method, after adding water and an acid catalyst, the temperature of the reaction solution is raised to 70 to 90 캜 and refluxed is carried out by using a weak general characteristic of the phosphorus- Oxazine-cyclohexylphosphoryl chloride produced in Step 1 is hydrolyzed to result in selective phosphorylation of the alcohol functional group.

The alcohol as the precipitation solvent used in the present invention is not particularly limited, but methanol, ethanol and isopropanol can be used, for example. In the present invention, alcohol is used as a precipitating solvent because triethylammonium chloride produced by neutralization of triethylamine dissolves in alcohol, but 3-aminopropane phosphoric acid, which is a desired product, is insoluble in alcohol solvent, Because.

The process for producing 3-aminopropane phosphoric acid according to the present invention is economical because it uses phosphorus oxychloride at a low price and the reaction is very simple as a two-step reaction. Can be usefully used.

Further, the present invention relates to a composition containing 3-aminopropane phosphoric acid produced by the above-described production method as an active ingredient, thereby improving the water retention ability of the skin, increasing the resilience against deformation, Or a pharmaceutically acceptable salt thereof. The cosmetic composition according to the present invention contains 3-aminopropane phosphoric acid or its salt in an amount of 0.001 to 20% by weight, preferably 0.1 to 5% by weight, based on the total weight of the cosmetic composition.

The 3-aminopropane phosphoric acid provided by the above-described preparation method is extremely excellent in solubility in water, so that it can be used in cosmetic formulations containing even a small amount of water, but since it has a low pH, it is neutralized and used in salt form desirable. Specific examples thereof include alkali metal salts such as sodium salts and potassium salts; Alkaline earth metal salts such as calcium salts and magnesium salts; Salts with basic amino acids such as lysine, arginine, and histidine; Salts with amines such as triethanolamine or with ammonia; Salts with cationic polymers such as polyquaternium-4, 6, 7, 10, 11, 16; And salts with cationic surfactants such as lauryldimethylbenzylammonium chloride and stearyldimethylbenzylammonium chloride.

Hereinafter, a process for preparing 3-aminopropane phosphoric acid according to the present invention and a cosmetic composition containing the same as an active ingredient will be described in more detail with reference to the following examples. However, the present invention is not limited to these examples.

[Production Example]

112 g of phosphorus oxychloride and 650 ml of dichloromethane were placed in a 2-liter flask equipped with a stirrer and a nitrogen gas injector, and the solution was cooled to 0 to 5 ° C in an ice water bath while injecting nitrogen gas into the flask. In another container, a solution of 50 g of 3-amino-1-propanol and 186 ml of triethylamine was diluted with 180 ml of dichloromethane, and then the above-prepared reaction solution was added dropwise for 30 minutes. After the dropwise addition, the reaction mixture was further stirred for 30 minutes, and triethylammonium chloride produced in the reaction was removed by filtration. After the filtrate was concentrated under reduced pressure, the concentrate was transferred to a 1 L flask equipped with a reflux apparatus, 300 mL of water and 3 mL of concentrated hydrochloric acid were added, and the mixture was heated under reflux for 2 hours. The reaction solution was cooled to room temperature and 90 ml of triethylamine was added. After stirring for 30 minutes at room temperature, 800 ml of ethanol was added dropwise at room temperature, and the resulting crystals were filtered and recrystallized from a mixture of water and ethanol. 93 g of 3-aminopropane phosphoric acid (yield: 90%) was obtained by drying under reduced pressure at 50 캜 so that the water content was less than 5%.

Melting point: 203 - 206 캜 (decomposition)

_{^{1 H-NMR (D 2 O}} ): δ (ppm) = 1.9 (m, 2H), 3.1 (t, 2H), 3.9 (q, 2H)

_{^{13 C-NMR (D 2 O}} ): δ (ppm) = 40.5 (s), 30.6 (d, 6.6), 65.8 (d, 5.3)

[Test Example 1] Effect of 3-aminopropane phosphoric acid

In order to investigate the effect of 3 - aminopropane phosphate on the skin, confirmation of proliferation of fibroblasts and promotion of collagen biosynthesis were examined in vitro by comparing with ascorbic acid. The morphological observation was performed using a hairless mouse to examine the effect of the application on the actual skin.

(1-1) Proliferation of fibroblasts

Type 1 collagenase was added to skin from the newborn epidermis to remove epidermis and fibroblasts were cultured. The culture medium was Dulbecco's modifed Eagle's media (DMEM).

The fibroblasts were measured by MTT method. The experimental results are shown in Table 1 below. The result is 100 for no addition.

density 0.001% 0.0001% 0.00001% 3-Aminopropane Phosphoric Acid 180 202 133 Ascorbic acid 128 149 138

From the results shown in Table 1, it can be seen that 3-aminopropane phosphoric acid is effective for cell proliferation.

(1-2) Promoting collagen synthesis

By the addition of ³ H- proline ⁽³ H-Proline) to the culture medium to the culture, and separating only collagen type 1 collagenase zero by measuring the amount of isotopes were compared to collagen synthesis by approximately 3-aminopropane phosphoric acid and ascorbic acid . The experimental results are shown in Table 2 below. The result is 100 for no addition.

density 0.001% 0.0001% 0.00001% 3-Aminopropane Phosphoric Acid 111 146 124 Ascorbic acid 103 103 120

From the results in Table 2, it can be seen that 3-aminopropane phosphoric acid is effective for collagen synthesis.

(1-3) Collagen synthesis after application

8-week-old hairless mice were treated with a cream base and 1% 3-aminopropane phosphoric acid added thereto for 3 weeks to obtain skin tissues. Then, the skin pellets were treated with a Type 1 pN collagen antibody and ABC (Avidin-Biotin Peroxidase Complex -biotin peroxidase complex) staining was performed by immunohistochemical staining. As a result, it was confirmed that collagen biosynthesis was increased compared with the case where no cream base coated with 3-aminopropane phosphoric acid was added.

[Test Example 2] Human safety of 3-aminopropane phosphoric acid

Since the ingredients of cosmetics are used in the human body, the safety of the human body is of utmost importance. In the present invention, it was confirmed that 3-aminopropane phosphoric acid was toxic and irritant to human body through the following experiment. The safety test of 3-aminopropane phosphoric acid was carried out by mixing a mixture prepared for direct use as a raw material of a cosmetic, that is, a mixture of 3-aminopropane phosphoric acid, glyceryl polymethacrylate, glycerin and purified water at a ratio of 1: 1.5: Mixture.

(2-1) Acute oral toxicity test

As a result of administering 1 ml / kg of 3-aminopropane phosphoric acid to 10 rats of 5 male and 5 female rats, there were no deaths and no significant difference in body weight before and after administration was observed.

(2-2) Acute dermal toxicity test

Aminopropane phosphoric acid (0.2 ml / kg) was transdermally administered to 10 rats in each of 5 male and 5 female rats, and general symptoms and weight changes were observed for 2 weeks. No abnormalities were observed in rabbits in the same way.

(2-3) Primary skin irritation test

Twelve rabbits were observed for 24 hours before application of the test material, removing the hairs from the back, applying 0.1 ml to 2.5 cm x 2.5 cm wide for 24 hours. Observation revealed no stimulation.

(2-4) Eye irritation test

Nine rabbits were diluted with saline at a concentration of 2%, and 0.1 ml / animal was administered to the eyes. Experimental results showed no specific mucosal irritation for cornea, iris, and conjunctiva.

(2-5) Skin sensitization test

Guinea pigs According to the test method of Magnusson and Kligman in 6 dogs of 3 male and 3 female, the skin abnormalities such as erythema, edema and scab formation could not be observed. And it was a highly safe substance belonging to the category of induced sensitization of grade 1 according to Klingmann criteria.

(2-6) Human patch test

The study was conducted in 30 healthy women aged 20-28 years according to the CTFA guidelines (The Cosmetic toiletry and Fragrance Association, INC., Washington, D.C., 20036, 1991). RESULTS: There were no primary skin irritation reactions, and suspicious erythema reactions were present in 4/30 ratios, but they all disappeared after 48 hours.

(2-7) Repeat insult human patch test

Experiments were conducted according to the CTFA guidelines for human patch test subjects. No cumulative stimulation or sensitization was observed.

In the above toxicity and safety test for skin, 3-aminopropane phosphoric acid was confirmed to be a safe substance for external skin application.

[Prescription Examples 1 to 2 and Comparative Examples 1 to 3] Moisture cream

ingredient Prescription Example 1 Prescription Example 2 Comparative Example 1 Comparative Example 2 Comparative Example 3 Glyceryl stearate monostearate cetostearyl alcohol squalane macadamia nut oil silicone oil polysorbate-60 glycerin preservative incense, pigment antioxidant ammonium 3-aminopropane phosphate 3-aminopropane phosphoric acid 3-aminopropane sulfonic acid taurine γ-amino Butyrate purified water 2.03.03.020.010.03.02.510.0. 2.03.03.020.010.03.02.510.0 Yield Yield Yield -5.0 --- to 100 2.03.03.020.010.03.02.510.0 Yield Yield Yield - 5.0 - to 100 2.03.03.020.010.03.02.510.0 [0060] 2.03.03.020.010.03.02.510.0.

[Formulation Examples 3 to 4 and Comparative Examples 4 to 6]

ingredient Prescription Example 3 Prescription Example 4 Comparative Example 4 Comparative Example 5 Comparative Example 6 Stearyl alcohol Self-emulsifying monostearate Glycerin Squalane Polysorbate-60 Sorbitan stearate Glycerin Antiseptic, colorant Antioxidant Lysine 3-Aminopropane Phosphate 3-Aminopropane Phosphoric acid 3-Aminopropane Sulfuric acid Taurine γ-Aminobutyric acid Purified water 0.52.020.02.00.55.0 < tb > < tb > 0.52.020.02.00.55.0 < tb > < SEP > 0.52.020.02.00.55.0 Optimum amount Optimal amount - 1.0 - to 100 0.52.020.02.00.55.0 < tb > < SEP > 0.52.020.02.00.55.0 < tb > < SEP >

[Test Example 3] Skin safety

In order to measure the safety of the skin, the patches of Table 3 and Table 4 were subjected to a general patch test, and the degree of stimulation was classified as follows.

+++: Very irritating and unsuitable for cosmetic use.

++: It is recommended to avoid use because of excessive stimulation.

+: There is slight irritation and caution should be used.

±: Almost no stimulation.

-: There is no irritation at all, so it may be used on sensitive skin.

=: There is no stimulation as a result of repeated experiments.

Name of sample Prescription Example 1 Prescription Example 2 Comparative Example 1 Comparative Example 2 Comparative Example 3 Judgment = = + + + Name of sample Prescription Example 3 Prescription Example 4 Comparative Example 4 Comparative Example 5 Comparative Example 6 Judgment = = + + +

Test Example 4 Skin Hydration (Hydration)

The moisturizing effect was measured by using a corneometer, skin moisture before and after application of the prescriptions shown in Tables 3 and 4, and skin hydration was confirmed to increase or decrease.

Name of sample Prescription Example 1 Prescription Example 2 Comparative Example 1 Comparative Example 2 Comparative Example 3 result 93% 90% 85% 64% 74% Name of sample Prescription Example 3 Prescription Example 4 Comparative Example 4 Comparative Example 5 Comparative Example 6 result 96% 94% 89% 77% 79%

[Test Example 5] Skin elasticity (Extensibility)

The flexibility of the skin of this test example and the resilience and the strength of the skin in the test examples 6 to 7 to be described later were such that 40 women between 21 and 36 years old were allowed to use the product for 4 weeks, Before and after 2 weeks of use, the skin condition after 4 weeks of use was measured using a fermometer, and the value at this time was expressed as a percentage of increase / decrease.

(unit : %) Name of sample Prescription Example 1 Prescription Example 2 Comparative Example 1 Comparative Example 2 Comparative Example 3 Results (2 weeks) +8 +8 +7 +5 +8 Results (4 weeks) +15 +17 +12 +9 +10 Name of sample Prescription Example 3 Prescription Example 4 Comparative Example 4 Comparative Example 5 Comparative Example 6 Results (2 weeks) +10 +11 +9 +6 +7 Results (4 weeks) +17 +17 +14 +8 +11

[Test Example 6] Resistance to deformation (Tonicity)

(unit : %) Name of sample Prescription Example 1 Prescription Example 2 Comparative Example 1 Comparative Example 2 Comparative Example 3 Results (2 weeks) +18 +19 +15 +9 +14 Results (4 weeks) +32 +33 +25 +19 +21 Name of sample Prescription Example 3 Prescription Example 4 Comparative Example 4 Comparative Example 5 Comparative Example 6 Results (2 weeks) +20 +18 +14 +11 +14 Results (4 weeks) +37 +34 +24 +18 +20

[Test Example 7] Firmness of skin

(unit : %) Name of sample Prescription Example 1 Prescription Example 2 Comparative Example 1 Comparative Example 2 Comparative Example 3 Results (2 weeks) +9 +8 +6 +6 +6 Results (4 weeks) +14 +15 +9 +8 +9 Name of sample Prescription Example 3 Prescription Example 4 Comparative Example 4 Comparative Example 5 Comparative Example 6 Results (2 weeks) +10 +12 +9 +6 +8 Results (4 weeks) +18 +19 +14 +8 +10

From the results shown in Tables 5 to 9, it is necessary to recognize an experimental error with respect to each experimental result, but it is generally accepted that the composition containing 2-aminopropane phosphoric acid or its salt is preferably 3-aminopropane sulfonic acid, Compared with a composition containing aminobutyric acid, it has less skin irritation, and shows good results in skin moisturizing effect, skin suppleness and resilience, and skin strength.

[Prescription Example 5] Transparent lotion

ingredient Content (% by weight) Glycerol polysorbate-20 ethanol Sodium 3-aminopropane phosphate 102102

Add an appropriate amount of perfume, coloring agent, preservative, antioxidant, and emollient agent to make 100% purified water.

[Prescription Example 6] High fatty acid cleansing foam

ingredient Content (% by weight) Stearic acid palmitic acid myristin acid lauric acid aqueous solution potassium oxide glycerin calcium 3-aminopropane phosphoric acid 1051566150.5

Add an appropriate amount of preservative, nonionic surfactant, coloring matter, and fragrance to make 100% purified water.

The process for producing 3-aminopropane phosphoric acid according to the present invention uses low-cost phosphorus oxychloride, the reaction is economical in two steps, and can be usefully used in industrial methods.

In addition, the cosmetic composition containing 3-aminopropane phosphoric acid or a salt thereof as an active ingredient provided by the present invention improves the water retention ability in the skin, increases the recovery power against deformation, skin strength, The effect of effectively reducing is excellent.

Claims (7)

A process for preparing 3-aminopropane phosphoric acid from 3-amino-1-propanol, (A) reacting 3-amino-1-propanol with phosphorus oxychloride in an equivalent ratio of 1: 1 to 1.3 in the presence of an organic solvent at a temperature of 0 to 5 DEG C for about 1 hour; (B) filtering the reaction solution to obtain a filtrate, and then hydrolyzing the filtrate under reduced pressure and concentration; And (C) Crystallization with alcohol Lt; RTI ID = 0.0 > 3-aminopropane < / RTI > The method of claim 1, wherein the organic solvent used in step (A) is dichloromethane, tetrahydrofuran, ethyl acetate, acetonitrile, chloroform or ethyl ether. The process for producing 3-aminopropane phosphoric acid according to claim 1, wherein the acid catalyst used in step (B) is hydrochloric acid, sulfuric acid or acetic acid. 4. The process according to claim 3, wherein the acid catalyst is added in an amount of 5.0 to 10.0 mol% based on the 2,6-oxa-cyclohexylphosphoryl chloride represented by the structural formula (V) ≪ / RTI > The process according to claim 1, wherein the alcohol used in step (C) is methanol, ethanol or isopropanol. A cosmetic composition characterized by containing 3-aminopropane phosphoric acid or its salt represented by the following structural formula (I) in an amount of 0.001 to 20% by weight based on the total weight of the composition. (I) 7. The method according to claim 6, wherein the salt of 3-aminopropane phosphoric acid is an alkali metal salt such as a sodium salt, a potassium salt or the like; Alkaline earth metal salts such as calcium salts and magnesium salts; Salts with basic amino acids such as lysine, arginine, and histidine; Salts with amines such as triethanolamine or with ammonia; Salts with cationic polymers such as polyquaternium-4, 6, 7, 10, 11, 16; And a salt with a cationic surfactant such as lauryldimethylbenzylammonium chloride and stearyldimethylbenzylammonium chloride.