KR101062772B1 - Poly ion complex, cosmetic composition using the same and method of manufacturing the same - Google Patents

Abstract

The present invention relates to a poly ion composite, a cosmetic composition using the same and a method for producing the same. The composite according to one embodiment of the present invention is a poly ion composite including an ionic bond between a water soluble anionic polymer and a hydrophobic cationic monomer. The poly-ion composite may be formed in a self-assembly in an aqueous solution, and may be applied as a cosmetic composition by carrying a fat-soluble pharmacological material.

Description

Poly ion complex, cosmetic composition using the same and method of manufacturing the same

The present invention relates to a stabilization technology for agents having biological activity, and more particularly, to a poly ion composite, a cosmetic composition using the same, and a method for preparing the same.

The structure of the skin consists of multiple structures of the stratum corneum, epidermis, dermis and subcutaneous tissue from the outside. The double stratum corneum (Stratum Corneum, SC) is the outermost layer in the skin and is very important to the human body because it is directly in contact with the external environment.

The stratum corneum contains 10 to 30% of moisture, and serves as a barrier to prevent the loss of moisture, electrolytes, etc. to the outside of the body, as well as to prevent excess moisture and foreign matter from penetrating from the outside. In addition, the stratum corneum that maintains the proper moisture content provides the skin with elasticity and flexibility, and allows the skin to function properly. When the moisture content of the stratum corneum is less than 10%, the skin becomes rough and the body loses its protective function, causing aging. In the case of dry skin, the aggregation of keratinocytes is weakened, and keratinocytes are separated from the surface of the skin like scaly pieces. Scaling phenomenon appears.

In addition, even in healthy skin, harsh external conditions such as wind, cold weather. Moisture in the stratum corneum can be reduced by a variety of causes, such as dry weather, sunlight or irritation caused by chemicals used in homes or industries, and various aging stresses and natural aging with increasing age, resulting in dry skin It is very important to properly maintain the moisture content of the stratum corneum because changes in skin appearance such as roughening and crumbness occur.

In general, commercial cosmetics used to maintain a proper moisture content on the skin utilize natural substances such as hyaluronic acid that are involved in the stratum corneum and promote moisturizing. However, these natural moisturizing substances alone do not easily penetrate into the stratum corneum and thus do not obtain an instant moisturizing effect or a long term moisturizing power.

In recent commercial cosmetics, a combination of functions such as anti-aging, wrinkle improvement and antibacterial activity as well as moisturizing effect is a trend. Therefore, there is a need for the development of a cosmetic composition that can be stably compatible with or enhance the efficacy of other active ingredients having pharmacologically active effects such as anti-aging, anti-wrinkle and antimicrobial activity, together with the aforementioned moisturizing effect.

The problem to be solved of the present invention is to improve the useful properties in products such as pharmacological effects or thickening, such as moisturizing effect, anti-aging, wrinkle improvement and / or antimicrobial enhancement, and stably compatible with other pharmacologically active ingredients Together with the other pharmacologically active ingredient is to provide a complex that may have a complex effect.

In addition, another problem to be solved by the present invention is to provide a cosmetic composition using a composite having the above-mentioned advantages.

In addition, another object of the present invention is to provide a method for producing the composite having the above-mentioned advantages.

In addition, another object of the present invention is to provide a method for producing a cosmetic composition using the above-described composition.

The composite according to an embodiment of the present invention for solving the above problems includes a cosmetic poly ion composite in which hydrophobic cationic monomers are ionically bonded to negatively charged portions of the water-soluble anionic polymer. The water-soluble anionic polymer may be at least one selected from the group consisting of hyaluronic acid, gamma-polyglutamic acid, sodium-carboxymethylcellulose, and carbomer. have. In addition, the hydrophobic cationic monomer may be at least one selected from the group consisting of lecithin, cocobetaine, cetyltrimethylammonium bromide, cetyltrimethylammonium chloride, and dimethyldiooctadecyl ammonium chloride. In some embodiments, the water soluble anionic polymer and the hydrophobic cationic monomer may have a weight ratio of 100: 1 to 1: 1.

Cosmetic composition according to an embodiment of the present invention for solving the other problems, the particulate poly ion complex ion-hydrophobic cationic monomers are bonded to the negatively charged portions of the water-soluble anionic polymer; And one or more fat soluble pharmacological substances physically bound to the poly ion composite. The fat-soluble pharmacological material may have a structure supported inside the particles of the poly ion composite.

In some embodiments, the fat-soluble pharmacological substance may be at least one selected from the group consisting of ceramide, retinol, cholesterol, saturated fatty acids having 12 to 18 carbon atoms and unsaturated fatty acids. The fat-soluble pharmacological material may be included in an amount of 0.01 to 5 parts by weight based on 100 parts by weight of the poly ion composite. Particles of the poly ion composite may have a size of 1 to 500 ㎛.

According to another aspect of the present invention, there is provided a method of preparing a poly ion composite, including: forming a mixed solution in which a water-soluble anionic polymer and a hydrophobic cationic monomer are mixed; And stirring the mixed solution to ionically couple the hydrophobic cationic monomers to the negatively charged portions of the water-soluble anionic polymer.

In some embodiments, the solvent of the mixed solution may include distilled water. The forming of the mixed solution may include forming a first solution of the water-soluble anionic polymer using a first solvent; And forming a second solution of the hydrophobic cationic monomer using a second solvent; And mixing the first solution and the second solution to form the mixed solution. In some embodiments, the first solvent is distilled water, and the second solvent may be an organic solvent having a lower boiling point than the distilled water. In some embodiments, the organic solvent may be any one or combination of 1,3-butylene glycol, 1,2-propylene glycol, glycerol, dipropylene glycol, which are acetone, ethanol, methanol, and polyols. have.

Method for producing a cosmetic composition according to an embodiment of the present invention for solving the another problem, forming a mixed solution of a water-soluble anionic polymer and a hydrophobic cationic monomer; Stirring the mixed solution to form a poly ion composite in which the hydrophobic cationic monomers are ionically bonded to the negatively charged portions of the water-soluble anionic polymer; And adding a solution in which the fat soluble pharmacological substance is dissolved to the mixed solution in which the poly ion complex is formed, to prepare particles in which the fat soluble pharmacological substance is physically bonded to the poly ion composite.

The fat-soluble pharmacological material may be supported inside the particles of the poly ion composite. The cosmetic composition may have a formulation of any one of skin, lotion, cream, gel, ointment, paste, powder foundation, emulsion foundation, wax foundation, spray, soap, shampoo, food and drink.

According to one embodiment of the present invention, a polyionic composite may be formed by a hydrophobic cationic monomer that is ionically bonded to a water-soluble anionic polymer, and the poly-ion composite may be a water-soluble anionic polymer such as a moisturizing power of a water-soluble anionic polymer. Not only can the properties be improved, but the usability can be modified. In addition, the poly ion composite may be provided with hydrophobicity by the cationic monomer to form a particle structure capable of supporting an effective pharmacologically active ingredient therein by self-assembly in an aqueous solution. Such particle structures may be applied to carry fat-soluble pharmacologically active ingredients to solubilize them or to improve dispersion stability.

In addition, according to the method for producing a poly ion composite according to another embodiment of the present invention, the poly ion composite may be easily produced by simply stirring the solution of the water-soluble anionic polymer and the hydrophobic cationic monomer.

In addition, according to another embodiment of the present invention, various cosmetic compositions including a fat-soluble pharmacologically active substance in the poly-ion composite may be provided.

1 schematically shows the structure of a poly ion composite according to one embodiment of the invention.
FIG. 2 is a graph illustrating a measurement result of a short time hydrating effect performed on poly ion composite and cosmetic compositions according to various embodiments of the present invention and corresponding comparative examples.

Hereinafter, the present invention will be described in more detail with reference to the following examples, but the following examples are only for illustrating the present invention, and the scope of the present invention is not limited thereto.

1 schematically shows the structure of a poly ion composite 30 according to one embodiment of the invention.

Referring to FIG. 1, a composite according to an embodiment is a poly ion composite 30 including an ionic bond between a water soluble anionic polymer 10 and a hydrophobic cationic monomer 20. The shape shown is exemplary and the present invention is not limited thereto. For example, in the water system, the poly ion composite 30 may form a stable particle structure by self-assembly. In addition, the shape of the poly ion composite 30 may vary depending on the mixing ratio of the hydrophobic cationic monomer 20 to the water soluble anionic polymer 10.

In some embodiments, hydrophobic cationic monomer 20 may comprise any one or combination of lecithin, cocobetaine, cetyltrimethylammonium bromide, cetyltrimethylammonium chloride, dimethyldiooctadecyl ammonium chloride have. The hydrophobic cationic monomer 20 increases the hydrophobicity of the poly ion composite 30 to assist in the formation of the self assembly of the poly ion composite 30 in an aqueous solution.

In some embodiments, the water soluble anionic polymer 10 may comprise any one or combination of hyaluronic acid, gamma-polyglutamic acid, sodium-carboxymethylcellulose, carbomer. However, the present invention is not limited thereto, and other natural or synthetic water soluble anionic polymer materials having suitable moisturizing power may be used. The molecular weight of the water-soluble anionic polymer 10 is 500,000 to 3,000,000 Da, preferably 1,000,000 to 3,000,000.

The weight ratio of the water-soluble anionic polymer 10 and the hydrophobic cationic monomer 20 of the poly ion composite 30 is 100: 1 to 1: 1, preferably 50: 1 to 2: 1, more preferably May be 20: 1 to 3: 1.

The hyaluronic acid in the water-soluble anionic polymer (10) is a non-toxic, biodegradable, biocompatible material, naturally present in the dermal layer and absorb moisture, for example, attracts about 6000 times the weight of the hyaluronic acid itself. The ability to pull and large molecules make the epidermis soft and maintain the proper flexibility and tension. In addition, the hyaluronic acid promotes the transport of nutrition and various minerals from the outside of the cell, and induces immune cells in the wound tissue during the initial inflammatory reaction to promote wound healing, and is a natural moisturizing agent with excellent water binding ability, and very water Pull firmly to form a gel.

The hyaluronic acid combines with the hydrophobic cationic monomer to form a poly ion complex, thereby reducing and offsetting the electrical repulsion between the human skin and the hyaluronic acid that is negatively charged by the hydrophobic cationic monomer, thereby further improving the moisturizing ability of the hyaluronic acid. , Synergistic effect occurs. This advantage will be apparent from Table 6 and a description thereof. It also provides the skin with the ability to store water instantly to soften the skin and improve its skin appearance.

In addition, in the case of gamma-polyglutamic acid, sodium-carboxymethyl cellulose, and carbomer, although it has moisturizing itself, since it has anionic property, similar advantages to hyaluronic acid can be obtained by forming a poly ion composite according to the present invention. Can be achieved.

Poly  Method for preparing ionic complexes and cosmetic compositions

Preparation of the poly ion composite may be accomplished by stirring a solution of a water soluble anionic polymer and a hydrophobic cationic monomer. In some embodiments, the water-soluble anionic polymer and the hydrophobic cationic monomer solution may use the same solvent, for example distilled water, to obtain a mixed solution. As another embodiment, for example, when the hydrophobic cationic monomer is not well dissolved in distilled water, acetone, ethanol, methanol and polyols 1,3-butylene glycol, 1,2-propylene glycol, glycerol And dissolving the hydrophobic cationic monomer using an organic solvent such as dipropylene glycol, mixing and stirring the solution of the water-soluble anionic polymer and the hydrophobic cationic monomer solution, and then removing the organic solvent having a low boiling point by distillation. It is also possible to form the poly ion composite.

In addition, by using the poly-ion composite to form a particle structure with self-assembly in an aqueous solution, at least one effective pharmacologically active ingredient, for example, a fat-soluble pharmacological substance is supported in the poly-ion composite so as to be solubilized or improved in stability. Cosmetic compositions in the form of particles may be provided. The fat-soluble pharmacological substance is, for example, ceramides, retinol, cholesterol, saturated fatty acids and unsaturated fatty acids having 12 to 18 carbon atoms, for example, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid , Linoleic acid or linolenic acid, or a combination thereof. The fat-soluble pharmacological material may be included in an amount of 0.01 to 5% by weight based on 100 parts by weight of the poly ion composite. The above-mentioned fat-soluble pharmacological substances are exemplary and they include various derivatives. For example, the ceramide may be any one of DS Y30 ceramide, PC102 ceramide, PC 104 ceramide, PC 107 ceramide, PC 108 ceramide, LC S20 ceramide, tocomid, PC 9S ceramide, and questamide H, or a combination thereof. And other known ceramides.

Forming the cosmetic composition comprises a first step of forming a mixed solution in which a water-soluble anionic polymer material and a hydrophobic cationic monomer are mixed; Stirring them to form a poly ion composite. Performing the third step of dissolving the fat-soluble cosmetic component in a suitable solvent, and then adding the solution of the third step to a poly ion complex solution of the water-soluble anionic polymer material and the hydrophobic cationic monomer obtained in the second step. The fourth step may be performed to obtain particles in which the fat-soluble cosmetic component is physically supported in the poly-ion composite. Optionally, step 5 may be further performed to remove the solvent of step 4 by drying under reduced pressure.

The poly ion composite is easily changed in structure by ionic bonding between the water soluble anionic polymer material and the hydrophobic cationic monomer, such that the water soluble anionic polymer material portion in the aqueous solution is external to the hydrophobicity of the hydrophobic cationic monomer. The portion undergoes a self-assembly process that collects internally and spontaneously forms fine particles, where the active particles, such as fat-soluble pharmacological substances, can be carried therein. The fine particles may be spherical, non-spherical, or irregular shape, and the size may be preferably 1 to 500 μm.

Example  1: hyaluronic acid-lecithin Poly  Preparation of Ionic Complexes

About 1 g of hyaluronic acid was dissolved in about 90 g of water with stirring at about 70 ° C. After dissolving about 30 mg of lecithin in ethanol, the resultant was mixed with the solution of hyaluronic acid and the ethanol was distilled while stirring at about 70 ° C. for about 2 hours.

Example  2: Ceramide DS - Y30 And hyaluronic acid-lecithin Poly  Preparation of Fine Particles in Ionic Composites

About 300 mg of ceramide DS-Y30 was dissolved in about 10 g of 1, 3-butylene glycol with stirring at about 70 ° C. The above solution was added to the solution of the poly ion composite prepared in Example 1, and stirred at about 70 ° C. for about 2 hours so that the ceramide DS-Y30 was physically supported or bound to the hyaluronic acid-lecithin poly ion composite. Was prepared.

Experimental Example 1 Measurement of Fine Particle Size of Ceramide DS-Y30 and Hyaluronic Acid-Lecithin Poly Ion Composite

The size of the fine particles of the ceramide DS-Y30 and hyaluronic acid-lecithin poly ion composite prepared in Example 2 was measured using a particle size analyzer (Particle Size Analyzer, Microtrac S3500). The results are shown in Table 1 below.

Average particle size in μm Experimental Example 1 4.78 Experimental Example 2 5.45 Experimental Example 3 3.84 Experimental Example 4 6.12 Experimental Example 5 4.88 Experimental Example 6 7.12 Experimental Example 7 6.49

In order to confirm the lecithin peak and the degree of inclusion of the hyaluronic acid-lecithin poly ion complex prepared in Example 1, it was measured using proton NMR spectroscopy. The results are shown in Table 2.

Hyaluronic acid Chemical mobility Integral ratio(%) Unreacted N-CH3 2.20 9.72 95 Reacted N-CH3 2.56 0.5 5

As shown in Table 2, it can be seen that in the hyaluronic acid-lecithin poly ion complex, lecithin is bound at a rate of about 5% with respect to the entire unit of hyaluronic acid.

Example  3: Ceramide PC  104 and hyaluronic acid-lecithin Poly  Preparation of Fine Particles in Ionic Composites

About 300 mg of ceramide PC 104 was dissolved in about 10 g of 1, 3-butylene glycol with stirring at about 70 ° C. The solution was added to the solution of the poly ion composite prepared in Example 1 and stirred at about 70 ° C. for about 2 hours to prepare fine particles in which ceramide PC 104 was physically supported on the hyaluronic acid-lecithin poly ion composite.

Experimental Example 2 Measurement of Fine Particle Size of Ceramide PC 104 and Hyaluronic Acid-Lecithin Poly Ion Composite

The size of the fine particles of ceramide PC 104 and hyaluronic acid-lecithin poly ion composite prepared in Example 3 was measured using a particle size analyzer (Particle Size Analyzer, Microtrac S3500). The results are shown in Table 1 above.

Example  4: Ceramide PC  108 and hyaluronic acid-lecithin Poly  Preparation of Fine Particles in Ionic Composites

About 300 mg of ceramide PC 108 was dissolved in about 10 g of 1, 3-butylene glycol with stirring at about 70 ° C. The solution was added to the poly ion composite solution prepared in Example 1 and stirred at about 70 ° C. for about 2 hours to prepare fine particles in which ceramide PC 108 was physically supported on the hyaluronic acid-lecithin poly ion composite.

Experimental Example 3: Measurement of Fine Particle Size of Ceramide PC 108 and Hyaluronic Acid-Lecithin Poly Ion Composite

The size of the fine particles of the ceramide PC 108 prepared in Example 4 and the hyaluronic acid-lecithin poly ion complex was measured using a particle size analyzer (Particle Size Analyzer, Microtrac S3500). The results are shown in Table 1 above.

Example  5: cholesterol and hyaluronic acid-lecithin Poly  Preparation of Fine Particles in Ionic Composites

About 300 mg of cholesterol was dissolved in about 10 g of 1, 3-butylene glycol with stirring at about 70 ° C. The solution was added to the solution of the poly ion composite prepared in Example 1, and stirred at about 70 ° C. for about 2 hours to prepare fine particles in which cholesterol was physically supported on the hyaluronic acid-lecithin poly ion composite.

Experimental Example 4: Measurement of Fine Particle Size of Cholesterol and Hyaluronic Acid-Lecithin Poly Ion Complex

The particle size of the cholesterol and hyaluronic acid-lecithin poly ion complex prepared in Example 5 was measured using a particle size analyzer (Particle Size Analyzer, Microtrac S3500). The results are shown in Table 1 above.

Example  6: retinol and hyaluronic acid-lecithin Poly  Preparation of Fine Particles in Ionic Composites

About 300 mg of retinol was dissolved in about 10 g of 1, 3-butylene glycol with stirring at about 70 ° C. The above solution was added to the poly ion composite solution prepared in Example 1 and stirred at about 70 ° C. for about 2 hours to prepare fine particles physically supported on the retinol hyaluronic acid-lecithin poly ion composite.

Experimental Example 5: Determination of fine particle size of retinol and hyaluronic acid-lecithin poly ion composite

The particle size of the retinol and hyaluronic acid-lecithin poly ion composite prepared in Example 6 was measured using a particle size analyzer (Particle Size Analyzer, Microtrac S3500). The results are shown in Table 1 above.

Example  7: Stearic acid and  Hyaluronic acid-lecithin Poly  Preparation of Fine Particles in Ionic Composites

About 300 mg of stearic acid was dissolved in 1, 3-butylene glycol with stirring at about 70 ° C. The solution was added to the poly ion composite solution prepared in Example 1 and stirred at about 70 ° C. for about 2 hours to prepare fine particles in which stearic acid was physically supported on the hyaluronic acid-lecithin poly ion composite.

Experimental Example 6: Determination of fine particle size of stearic acid and hyaluronic acid-lecithin poly ion composite

The particle size of the stearic acid and hyaluronic acid-lecithin poly ion composite prepared in Example 7 was measured using a particle size analyzer (Particle Size Analyzer, Microtrac S3500). The results are shown in Table 1 above.

Example  8: Oleic acid and  Hyaluronic acid-lecithin Poly  Preparation of Fine Particles in Ionic Composites

About 300 mg of oleic acid was dissolved in 1, 3-butylene glycol with stirring at about 70 ° C. The solution was added to the poly ion composite solution prepared in Example 1 and stirred at about 70 ° C. for about 2 hours to prepare fine particles in which oleic acid was physically supported on the hyaluronic acid-lecithin poly ion composite.

Experimental Example 7: Determination of fine particle size of oleic acid and hyaluronic acid-lecithin poly ion composite

The size of the fine particles of the oleic acid and hyaluronic acid-lecithin poly ion composite prepared in Example 8 was measured using a particle size analyzer (Particle Size Analyzer, Microtrac S3500). The results are shown in Table 1 above.

The above embodiments are illustrative and the present invention is not limited to these embodiments. For example, a poly ion composite solution including ionic bonds between the various water soluble anionic polymers and hydrophobic cationic monomers described above can be prepared. For example, the poly-ion complex solution is a solvent, for example, dissolved in water by stirring a predetermined amount of a water-soluble anionic polymer such as gamma-polyglutamic acid, sodium-carboxymethyl cellulose or carbomer, and another container. Dissolved in a predetermined amount of hydrophobic cationic monomer, such as cocobetaine, cetyltrimethylammonium bromide, cetyltrimethyl ammonium chloride and / or dimethyldioctadecyl ammonium chloride in water. Then, it can be obtained by adding and stirring the hydrophobic cationic monomer solution to the water-soluble anionic polymer solution prepared first. Then, ceramides, retinol, cholesterol, saturated fatty acids and unsaturated fatty acids having 12 to 18 carbon atoms, for example lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid or linolenic acid The fat-soluble pharmacological substance, such as any one or a combination thereof, is dissolved in a suitable solvent such as alcohol, 1,3 butylene glycol, and then the solution is added to the poly-ion complex solution and stirred to make the fat-soluble pharmacological substance. A material may produce fine particles supported on the poly ion composite. The fine particles may have a size of 1 to 500 ㎛.

< Test Example > Property and chemical stability test

1% cream formulation and 5% cream formulation of the water-soluble anionic polymer material and the hydrophobic cationic monomer prepared in Examples 1 to 8 were prepared, respectively, at 45 ° C, RT (30 ° C), 4 Storage at 0 ° C. for 0 weeks, 1 week, 2 weeks, 3 weeks, and 4 weeks was performed to observe the change in appearance, sensory test, and moisturizing effect experiment.

The change in appearance was visually observed. No change in color or phase separation was observed at 45 ° C, RT (30 ° C), and 4 ° C at 0, 1, 2, 3, and 4 weeks, respectively.

< Test Example > Sensory test and moisturizing effect

In addition to Example 1 of the poly ion composite of the present invention, for the evaluation of the sensory test and the moisturizing effect of Examples 2 to 8 which is a cosmetic composition loaded with a fat-soluble pharmacological substance, these Examples 2 to A mixture according to Comparative Examples 1 to 8, which is a control group, respectively, was prepared. The mixture of these comparative examples is a mixture of a fat-soluble pharmacological substance and a water-soluble anionic polymer in a predetermined ratio, and is distinguished from the cosmetic composition of the present invention in that the fat-soluble pharmacological substance is not supported in the particles.

1. Comparative Example 1: Preparation of hyaluronic acid solution

About 1 g of hyaluronic acid was dissolved in about 99 g of water with stirring at about 70 ° C. Thereafter, the resulting composition was used to prepare a cosmetic composition in a 1% cream formulation and a 5% cream formulation.

2. Comparative Example 2: Preparation of ceramide DS-Y30 and hyaluronic acid mixture

300 mg of ceramide DS-Y30 was dissolved in 10 g of 1, 3-butylene glycol with stirring at 70 ° C. The solution was added to the hyaluronic acid solution and stirred at 70 ° C. for 2 hours to prepare a mixture. Thereafter, the resulting composition was used to prepare a cosmetic composition in a 1% cream formulation and a 5% cream formulation.

3. Comparative Example 3: Preparation of ceramide PC 104 and hyaluronic acid mixture

300 mg of ceramide PC 104 was dissolved in 10 g of 1, 3-butylene glycol with stirring at 70 ° C. The solution was added to the hyaluronic acid solution and stirred at 70 ° C. for 2 hours to prepare a mixture. Thereafter, the resulting composition was used to prepare a cosmetic composition in a 1% cream formulation and a 5% cream formulation.

4. Comparative Example 4: Preparation of Ceramide PC 108 and Hyaluronic Acid Mixture

300 mg of ceramide PC 108 was dissolved in 10 g of 1, 3-butylene glycol with stirring at 70 ° C. The solution was added to the hyaluronic acid solution and stirred at 70 ° C. for 2 hours to prepare a mixture. Then, using the result obtained to prepare a cosmetic composition in 1% cream formulation and 5% cream formulation.

5. Comparative Example 5: Preparation of Cholesterol and Hyaluronic Acid Mixture

300 mg of cholesterol was dissolved in 10 g of 1, 3-butylene glycol with stirring at 70 ° C. The solution was added to the hyaluronic acid solution and stirred at 70 ° C. for 2 hours to prepare a mixture. Thereafter, the resulting composition was used to prepare a cosmetic composition in a 1% cream formulation and a 5% cream formulation.

6. Comparative Example 6: Preparation of Retinol and Hyaluronic Acid Mixture

300 mg of retinol was dissolved in 10 g of 1, 3-butylene glycol with stirring at 70 ° C. The solution was added to the hyaluronic acid solution and stirred at 70 ° C. for 2 hours to prepare a mixture. Thereafter, the resulting composition was used to prepare a cosmetic composition in a 1% cream formulation and a 5% cream formulation.

7. Comparative Example 7: Preparation of Stearic Acid and Hyaluronic Acid Mixture

300 mg of stearic acid was dissolved in 1, 3-butylene glycol with stirring at 70 ° C. The solution was added to the hyaluronic acid solution and stirred at 70 ° C. for 2 hours to prepare a mixture. Then, using the result obtained to prepare a cosmetic composition in 1% cream formulation and 5% cream formulation.

8. Comparative Example 8: Preparation of Oleic Acid and Hyaluronic Acid Mixture

300 mg of oleic acid was dissolved in 1, 3-butylene glycol with stirring at 70 ° C. The solution was added to the hyaluronic acid solution and stirred at 70 ° C. for 2 hours to prepare a mixture. Thereafter, the resulting composition was used to prepare a cosmetic composition in a 1% cream formulation and a 5% cream formulation.

In the sensory test, the average value of each group was measured by measuring the intensity of the odor of 10 healthy women in their 20s, and the intensity of the odor was set as shown in Table 3 below.

Bad smell Explanation 0 Odorless One Detection 2 Normal odor 3 Strong odor 4 Extreme odor 5 Unbearable odor

In addition, the moisturizing effect test was commissioned by the skin clinical research institute, Ltd., Ltd., a short time hydration test (Short Time Hydrating Effect) to measure the amount of skin moisture change with the time change before and after application. The Short Time Hydrating Effect was conducted by a dermatologist who conducted physical examination and questionnaire on the skin, and selected 10 people who met the selection criteria and did not meet the exclusion criteria. 24 hours of skin moisturizing effect evaluation was performed without knowing the information.

The test site (forearm) is a forearm flexion part 5 cm from the left or right arm of the test subject or both arms, and a 1 cm circle is now drawn at 1.5 cm intervals for each test part. Prior to device evaluation using non-invasive measuring equipment, the subject waited for 30 minutes in a waiting room under constant temperature and humidity conditions (temperature 20-24, humidity 40-60%). After 30 minutes, the investigator measured the test site five times with a Coneometer (CM825, Courage & Khazaka, Germany) and averaged three measurements except the maximum minimum. After evaluating the device, the sample was applied to the test site of the subject by 2 / cm ² and allowed to be sufficiently absorbed, and then waited at constant temperature and humidity. After 30 minutes, 1 hour, about 2 hours, 4 hours, 6 hours and 24 hours after sample application, each test site was measured by the same method.

The results of the sensory test and the short time hydration test (Short Time Hydrating Effect) performed on the poly ion composite and the cosmetic compositions according to various embodiments of the present invention and the comparative examples are shown in the following [Table 4] and [Table 5]. , And in the graph of FIG. 2.

Table 4 shows the sensory test evaluation values for the samples of Examples 1 to 8 and Comparative Examples 1 to 8, and Table 5 shows the degree of improvement in the moisturizing power of Examples 1 to 8 for each of Comparative Examples 1 to 8.

Experimental group Sensory test (by direct sensory method) 1% content cream formulation 5% content cream formulation Example 1 0.01 0.12 Example 2 0.12 0.18 Example 3 0.13 0.22 Example 4 0.08 0.13 Example 5 0.11 0.23 Example 6 0.15 0.24 Example 7 0.18 0.30 Example 8 0.22 0.35 Comparative Example 1 0.05 0.15 Comparative Example 2 0.13 0.20 Comparative Example 3 0.18 0.30 Comparative Example 4 0.24 0.32 Comparative Example 5 0.36 0.48 Comparative Example 6 0.27 0.41 Comparative Example 7 0.21 0.38 Comparative Example 8 0.32 0.48

(Example-Comparative Example) / Comparative Example Sensory test performance evaluation result (%) 1% content cream formulation 5% content cream formulation Example 1 Vs Comparative Example 1 80% 20% Example 2 Vs Comparative Example 2 33.3% 10% Example 3 Vs Comparative Example 3 45.8% 26.7% Example 4 Vs Comparative Example 4 77.8% 59.4% Example 5 Vs Comparative Example 5 59.3% 52.1% Example 6 Vs Comparative Example 6 28.6% 41.5% Example 7 Vs Comparative Example 7 43.8% 21.1% Example 8 Vs Comparative Example 8 31.3% 27.1% Average improvement 50.0% 32.2%

Referring to Table 4, as a result of applying the poly-ion complex according to the above-described embodiments to the cream formulation, the odor or odor of the raw material did not occur to have a value of less than one. The cosmetic compositions of Examples 1 to 8 all exhibited excellent performance as compared to the comparative cosmetic compositions according to Comparative Examples 1 to 8. Referring to Table 5, in the 1% content cream formulation, Examples 1-8 showed a 50.0% performance improvement on average. In addition, in the 5% content cream formulations, Examples 1-8 showed a 32.2% performance improvement on average. In addition, it is remarkable that by forming a poly ion complex (corresponding to Example 1) of hyaluronic acid using a hydrophobic cationic monomer in the degree of improving the moisturizing power, it is improved by 80% or more than pure hyaluronic acid (corresponding to Comparative Example 1).

From this, it could be confirmed that the particles by the poly ion composite formed by the addition of the hydrophobic cationic monomer had a remarkable moisturizing effect compared with a simple mixture having no complex structure, and no odor or odor was found. It was confirmed that the suitability and stability as a cosmetic formulation.

In Fig. 2, the red curves represent the moisturizing power measurement results of Examples 1 to 8, the blue curves represent the measurement results of Comparative Examples 1 to 8, and the uncoated curve and the base curve shown in black are each nothing. The measurement result is shown in the case where the uncoated uncoated state and the usual cream base (see the curve referred to as Base) without any additives are applied.

Referring to FIG. 2, Examples 1 to 8 and Comparative Examples 1 to 8 all exhibited improved short-term moisturizing power over an uncoated state and a cream base applied state. The improved short-term moisturizing power observed in Comparative Examples 1 to 8 is basically due to the moisturizing power of hyaluronic acid, which is a water-soluble anionic polymer included in the mixture.

As compared to Comparative Examples 1 to 8 showing the improved moisturizing power as described above, it can be seen that all of Examples 1 to 8 of the present invention exhibit more improved short-term moisturizing power than the comparative examples. Table 6 is a table showing the degree of improvement of the short-term moisturizing power of the improved Examples 1 to 8 with respect to Comparative Examples 1 to 8 shown in FIG.

(Example-Comparative Example) / Comparative Example Short-term moisturizing ability evaluation results (%) 0 hours 30 minutes 1 hours 2 hours 4 hours 6 hours 24 hours Average Example 1 Vs Comparative Example 1 0.8% 6.0% 7.5% 12.3% 22.3% 25.3% 19.7% 13.4% Example 2 Vs Comparative Example 2 -1.2% 8.4% 11.3% 16.8% 21.4% 26.4% 22.9% 15.1% Example 3 Vs Comparative Example 3 -1.6% 10.5% 12.6% 11.2% 8.0% 6.6% 11.2% 8.4% Example 4 Vs Comparative Example 4 4.4% 13.2% 12.8% 15.4% 12.7% 7.0% 5.5% 10.2% Example 5 Vs Comparative Example 5 -0.4% 10.1% 10.5% 11.0% 12.5% 14.3% 5.6% 9.1% Example 6 Vs Comparative Example 6 0.0% 10.5% 10.0% 8.3% 9.7% 6.0% 2.6% 6.7% Example 7 Vs Comparative Example 7 1.6% 3.9% 7.2% 11.8% 6.1% 6.9% 5.5% 6.2% Example 8 Vs Comparative Example 8 2.4% 6.2% 9.0% 4.4% 3.7% 6.8% 5.5% 5.4%

Referring to Table 6 with FIG. 2, Examples 1 to 8, on average, compared to the respective Comparative Examples 1 to 8, 13.4%, 15.1%, 8.4%, 10.2%, 9.1%, 6.7%, 6.2%, and A 5.4% improvement in moisturizing power was shown. Particularly, in the case of Example 1, the moisture retention was improved by 19.69% over pure hyaluronic acid at the time point of 24 hours. From this, it can be seen that poly ion complexes such as hyaluronic acid-lecithin are better at increasing short-term moisturizing power than hyaluronic acid itself.

In addition, in Examples 2 to 8, the short-term moisturizing power is further improved by supporting the fat-soluble pharmacological substance in the poly-ion composite rather than the simple mixture of the fat-soluble pharmacological substance and hyaluronic acid, and due to the moisturizing effect provided by the poly-ion composite, In addition to maintaining this stability, it is expected that fat-soluble pharmacological substances can be rapidly absorbed into the body.

As described above, according to the present invention, the poly ion composite including the ionic bond between the water-soluble anionic polymer material and the hydrophobic cationic monomer improves the moisturizing effect of the pure water-soluble anionic polymer material used as a conventional moisturizing agent. As a result, an immediate and lasting moisturizing effect can be expected. In addition, the poly ion composite includes an ionic bond having structural flexibility compared to a chemical bond, and has a self-assembly property capable of forming a particle structure in an aqueous solution due to the amphoteric property of the water-soluble polymer material and the hydrophobic monomer. As such, by supporting the fat-soluble cosmetic component in the interior using the poly-ion composite which can obtain a self-assembly process in the aqueous solution, it maximizes the moisturizing power, solubilizing the fat-soluble cosmetic component in the aqueous solution or provide dispersion stability. Additional benefits can be expected.

The foregoing examples illustrate the benefits of the present invention with respect to the moisturizing effect, but this is illustrative, and one skilled in the art will appreciate other inherent effects of the water-soluble anionic polymeric material by the positive charge of the hydrophobic cationic monomer, eg For example, it should be understood that pharmacologically active effects such as antimicrobial activity, wrinkle improvement or whitening may be better expressed on human skin, and the present invention should not be limited by these listed effects. In addition, it is to be understood that the self-assembling properties of the poly ion composite may achieve other pharmacological effects depending on the cosmetic composition, as well as the fat-soluble substance loaded therein.

In addition, those skilled in the art will recognize that in addition to cosmetics, other cosmetic applications such as soaps and shampoos that can be used for skin, scalp and drinking, by pharmacological effects such as the inherent whitening and wrinkle improvement of ellagic acid, can be used by those skilled in the art. It is to be understood that the beverages and the like are also included in the present invention.

It will be apparent to those skilled in the art that various modifications and variations can be made in the present invention without departing from the spirit or scope of the invention. Will be clear to those who have knowledge of.

Claims (19)

A cosmetic poly ion composite in which hydrophobic cationic monomers are ion-bonded to negatively charged portions of a water-soluble anionic polymer to form particles by self-assembly in an aqueous system. The method of claim 1,
The water-soluble anionic polymer is a cosmetic poly ion composite, characterized in that the molecular weight of 500,000 to 3,000,000 Da. The method of claim 1,
The water-soluble anionic polymer is one or more selected from the group consisting of hyaluronic acid, gamma-polyglutamic acid, sodium-carboxymethylcellulose, and carbomer. Cosmetic poly ion composite characterized in that. The method of claim 1,
The hydrophobic cationic monomer is at least one cosmetic poly ion selected from the group consisting of lecithin, cocobetaine, cetyltrimethylammonium bromide, cetyltrimethylammonium chloride, and dimethyldioctadecyl ammonium chloride. Complex. The method of claim 1,
The water-soluble anionic polymer and the hydrophobic cationic monomer is a cosmetic poly ion composite, characterized in that it has a weight ratio of 100: 1 to 1: 1. Particulate poly ion composites in which hydrophobic cationic monomers are ionically bonded to the negatively charged portions of the water-soluble anionic polymer; And
Cosmetic composition comprising at least one fat-soluble pharmacological material physically bonded to the poly ion composite. The method according to claim 6,
The fat-soluble pharmacological material is a cosmetic composition, characterized in that supported on the inside of the particles of the poly ion composite. The method according to claim 6,
The fat-soluble pharmacological material is a cosmetic composition, characterized in that at least one selected from the group consisting of ceramides, retinol, cholesterol, saturated fatty acids having 12 to 18 carbon atoms and unsaturated fatty acids. The method according to claim 6,
The fat-soluble pharmacological material is a cosmetic composition, characterized in that contained in 0.01 to 5 parts by weight based on 100 parts by weight of the poly ion composite. The method according to claim 6,
The cosmetic composition is a cosmetic, characterized in that it is added to any one of the skin, lotion, cream, gel, ointment, paste, powder foundation, emulsion foundation, wax foundation, spray, soap, shampoo, food and beverage formulations Composition. Forming a mixed solution in which the water-soluble anionic polymer and the hydrophobic cationic monomer are mixed; And
Stirring the mixed solution to ionically couple the hydrophobic cationic monomers to the negatively charged portions of the water-soluble anionic polymer. The method of claim 11,
The solvent of the mixed solution is a method of producing a cosmetic poly ion composite, characterized in that it comprises distilled water. The method of claim 11, wherein forming the mixed solution,
Forming a first solution of the water-soluble anionic polymer using a first solvent;
Forming a second solution of said hydrophobic cationic monomer using a second solvent; And
And mixing the first solution and the second solution to form the mixed solution. The method of claim 13,
The first solvent is distilled water, the second solvent is a method for producing a cosmetic poly ion composite, characterized in that the boiling point is lower than the distilled water. The method of claim 14,
The organic solvent is prepared from acetone, ethanol, methanol and polyols 1,3-butylene glycol, 1,2-propylene glycol, glycerol, dipropylene glycol production of a cosmetic poly ion composite Way. Forming a mixed solution in which the water-soluble anionic polymer and the hydrophobic cationic monomer are mixed;
Stirring the mixed solution to form a poly ion composite in which the hydrophobic cationic monomers are ionically bonded to the negatively charged portions of the water-soluble anionic polymer; And
And adding a solution in which the fat soluble pharmacological substance is dissolved to the mixed solution in which the poly ion complex is formed, to prepare particles in which the fat soluble pharmacological substance is physically bonded to the poly ion composite. 17. The method of claim 16,
The fat-soluble pharmacological material is a manufacturing method of the cosmetic composition, characterized in that supported on the inside of the particles of the poly ion composite. The cosmetic composition of claim 16, wherein the cosmetic composition has a formulation of any one of skin, lotion, cream, gel, ointment, paste, powder foundation, emulsion foundation, wax foundation, spray, soap, shampoo, food, and beverage. Method for producing a cosmetic composition, characterized in that. The poly-ion complex according to claim 1 is added to the formulation of any one of skin, lotion, cream, gel, ointment, paste, powder foundation, emulsion foundation, wax foundation, spray, soap, shampoo, food and beverage. Cosmetic composition characterized in that.

Images