KR20220058254A - Cosmetic composition for improving skin gloss or moisturizing skin comprising zwitterionic chitosan derivative - Google Patents

Abstract

Provided is a cosmetic composition for improving skin gloss or moisturizing skin comprising a zwitterionic chitosan derivative. The zwitterionic chitosan derivative includes a repeating unit represented by chemical formula 1.

Description

Cosmetic composition for improving skin gloss or moisturizing skin comprising zwitterionic chitosan derivative

It relates to a cosmetic composition for improving skin gloss or moisturizing the skin.

Chitosan is a kind of naturally-derived aminopolysaccharide, obtained by deacetylating chitin contained in the cell walls of microorganisms such as crabs, shrimp shells, squid bones, molds, mushrooms and bacteria. is a homopolymer of Their main role in living organisms is to form an exoskeleton of the living body to protect the living body from the external environment and to maintain homeostasis.

The main component of chitosan is polyglucosamine, which is a colorless amorphous powder with a polymer structure. Chitosan, which is a glucosamine bond, has a molecular structure similar to that of human tissue, and has excellent affinity for the human body and does not cause an immune response. It is a very valuable biomaterial used. However, since most of the chitosan that has been used in the cosmetic field is fat-soluble chitosan, only a very small amount is dissolved in oil or simply used as a concept ingredient in order to exhibit practical efficacy.

Chitosan is an insoluble substance that is not soluble in water because it is firmly bound by strong hydrogen bonds between neighboring molecules. Organic acids including lactic acid, acetic acid, propionic acid, formic acid, ascorbic acid, and tartaric acid in order to dissolve the conventional chitosan; and an inorganic acid composed of hydrochloric acid, nitric acid and sulfuric acid. Recently, research on grafting sugar acids to develop water-soluble chitosan that is more suitable for in vivo application has also been conducted (Patent Document 1).

However, water-soluble chitosan has been limitedly applied to anticancer treatment and food additives. In particular, since low molecular weight chitosan in the form of an oligomer has been mainly used in the food industry, studies on the effect of high molecular weight chitosan of 100,000 kDa or more have not been made. In particular, chitosan used for medical purposes is beta-chitosan in an isomeric form, and since it is quite expensive, there is a realistic entry barrier that it is difficult to apply to the cosmetic industry.

Therefore, there is a need for research on water-soluble high molecular weight chitosan derivatives applicable to the cosmetic industry.

KR 10-2019-0080845 A

Provided is a cosmetic composition for improving skin gloss or moisturizing the skin comprising a zwitterionic chitosan derivative.

Provided is a method for improving skin gloss or moisturizing a subject, comprising administering an effective amount of a zwitterionic chitosan derivative to a subject in need thereof.

Provided is a use of a zwitterionic chitosan derivative for preparing a cosmetic composition for improving skin gloss or moisturizing the skin.

One aspect provides a cosmetic composition for improving skin gloss or moisturizing the skin comprising a zwitterionic chitosan derivative.

The term “improving skin luster” may refer to any action that increases skin luster or a radiance that makes the skin shiny and smooth.

The term “moisturizing the skin” may refer to any action that retains moisture in the skin or prevents moisture loss.

In one embodiment, it was confirmed that the cosmetic composition containing the zwitterionic chitosan derivative is very excellent in improving skin gloss or moisturizing the skin compared to the cosmetic composition containing chitosan.

In another embodiment, since it was confirmed that the zwitterionic chitosan derivative does not have cytotoxicity and skin side effects, it can be safely applied to a cosmetic composition.

The term "zwitterionic" is used interchangeably with "amphoteric," and has acidic (eg -COOH) and basic (eg -NH ₂ ) groups in the molecule, such as acids and bases. It means that it is capable of reacting with all of them.

The term “chitosan” refers to a substance obtained by deacetylation of chitin. The chitosan may include all forms of chitosan, such as an alpha or beta isomer.

The term “derivative” refers to a similar compound obtained by chemically modifying part of a compound.

The "zwitterionic chitosan derivative" may be a derivative obtained by modifying chitosan to have zwitterionic properties. Specifically, the derivative modified to have an anionic moiety in chitosan has an amine group (-NH ₂ ) present in chitosan has a positive charge, and the anion moiety has a negative charge, so it can have zwitterionic properties.

The zwitterionic chitosan derivative may include a repeating unit represented by the following formula (1).

[Formula 1]

(In Formula 1, X is the same or different from each other in each repeating unit and is each independently H, -COCH ₃ or an anionic moiety.)

In Formula 1, the repeating unit in which X is H may be a repeating unit of deacetylated chitosan (hereinafter, referred to as “repeating unit A”).

In Chemical Formula 1, the repeating unit in which X is -COCH ₃ may be a non-deacetylated repeating unit of chitosan (hereinafter, referred to as “repeating unit B”).

In Formula 1, the repeating unit in which X is an anionic moiety may be a repeating unit in which the amine group (—NH ₂ ) of chitosan is modified to have an anionic moiety (hereinafter, referred to as “repeating unit C”).

In Formula 1, X may be the same or different from each other in each repeating unit. Accordingly, the zwitterionic chitosan derivative may include a repeating unit A and a repeating unit C, or include a repeating unit B and a repeating unit C, or may include a repeating unit A, a repeating unit B, and a repeating unit C. The number of repeating units A, B, and C in the total number of repeating units of the zwitterionic chitosan derivative may be different.

The term “anionic moiety” means a moiety that is negatively charged. The anionic moiety may have a negative charge of -1 or -2.

The anionic moiety is any one selected from the group consisting of -RSO ₃ H (sulfonate), -RCOOH (carboxylate) and -RPO ₂ HR' (phosphonate), and R and R' are each independently It may be a C1-C20 aliphatic or aromatic hydrocarbon group substituted or unsubstituted with R and R' are each independently a substituted or unsubstituted C1-C20 alkylene group, a substituted or unsubstituted C3-C20 cycloalkylene group, a substituted or unsubstituted C6-C20 arylene group, or a substituted or unsubstituted C7 It may be a -C20 aralkylene group.

When two or more repeating units C are included in one molecule of the zwitterionic chitosan derivative, the types of anionic moieties of the repeating units C may be the same or different from each other in each repeating unit C. In one embodiment, when one molecule of the zwitterionic chitosan derivative includes two or more repeating units C, the type of the anionic moiety of the repeating unit C may be the same in each repeating unit C.

In one embodiment, when two or more repeating units C are included in one molecule of the zwitterionic chitosan derivative, each repeating unit C may have an anionic moiety -RSO ₃ H. Such zwitterionic chitosan derivatives may be referred to as "sulfonated chitosan". The sulfonated chitosan can be synthesized by reacting 1,3-propanesultone with the amine group of chitosan.

In another embodiment, when two or more repeating units C are included in one molecule of the zwitterionic chitosan derivative, each repeating unit C may have an anionic moiety -RCOOH. Such zwitterionic chitosan derivatives may be referred to as "carboxylated chitosan". The carboxylated chitosan may be synthesized by reacting chloroacetic acid or brominated acetic acid with an amine group of chitosan.

In another embodiment, when two or more repeating units C are included in one molecule of the zwitterionic chitosan derivative, each repeating unit C may have an anionic moiety -RPO ₂ HR′. Such zwitterionic chitosan derivatives may be referred to as “phosphorylated chitosan”. The phosphorylated chitosan may be synthesized by reacting phenyl phosphoric acid with an amine group of chitosan.

Chitosan used in the preparation of the zwitterionic chitosan derivative is not limited in its molecular weight, but may be, for example, high molecular weight chitosan. Specifically, the chitosan may be chitosan having a molecular weight of 1,000 kDa or more, 10,000 kDa or more, 100,000 kDa or more, or 1,000 kDa to 1,000,000 kDa.

The zwitterionic chitosan derivative has a total number of repeating units of 10 to 1,000, 10 to 900, 10 to 800, 10 to 700, 10 to 600, 10 to 500, 100 to 1,000, 100 to 900, 100 to 800, 100 to 700, 100 to 600, 100 to 500, or 500 to 1,000.

Chitosan used in the preparation of the zwitterionic chitosan derivative may have a deacetylation degree of 70% or more, 75% or more, 80% or more, 70 to 100%, 75 to 100%, or 80 to 100%. Accordingly, the ratio of the repeating unit (repeating unit B) in which X is -COCH ₃ in Formula 1 among the total number of repeating units of the zwitterionic chitosan derivative is 30% or less, 25% or less, 20% or less, 0 to 30 %, 0-25%, or 0-20%.

The ratio of the repeating unit (repeating unit C) in which X is an anionic moiety in Formula 1 among the total number of repeating units of the zwitterionic chitosan derivative is greater than 50%, greater than 60%, greater than 70%, greater than 80%, greater than 90% % or more, 60 to 99%, 70 to 99%, 80 to 99%, or 90 to 99%. When the ratio of the repeating unit C among the total number of repeating units of the zwitterionic chitosan derivative is 50% or less, it may not be well soluble in water.

The ratio of the repeating unit C among the total number of repeating units of the zwitterionic chitosan derivative may be referred to as the "Zwitterionization degree (ZD)" or "ionization ratio" of the zwitterionic chitosan derivative.

The cosmetic composition contains 0.1 to 10% by weight of the zwitterionic chitosan derivative, 0.1 to 5% by weight, 0.1 to 3% by weight, 0.1 to 2% by weight, 0.5 to 10% by weight, 0.5 to 5% by weight based on the total weight of the composition , 0.5 to 3% by weight, or 0.5 to 2% by weight may be included.

The cosmetic composition may be an oil-in-water emulsion formulation.

The cosmetic composition comprises: an aqueous phase comprising a zwitterionic chitosan derivative; And it may be an oil-in-water emulsion formulation comprising an oil phase.

The aqueous phase may be included in an amount of 70 to 95% by weight based on the total weight of the composition, but is not limited thereto.

The aqueous phase may further include a polyol. The terms "polyol" and "polyhydric alcohol" are used interchangeably and refer to an aliphatic compound having two or more hydroxyl groups (-OH). The polyol may be glycerol, glycols, sorbitol, or a combination thereof. The glycerol may be glycerin, diglycerin, polyglycerin, glyceritol, glycyl alcohol, or a combination of two or more thereof. The glycerin may be used interchangeably with other commonly used names such as lysline, propane-1,2,3-triol, 1,2,3-propenetriol, and trihydroxypropane. The glycols may be propylene glycol, dipropylene glycol, butylene glycol, diethylene glycol, triethylene glycol, hexylene glycol, pentylene glycol, polyethylene glycol, methylpropanediol, or a combination of two or more thereof.

The oil phase may be included in an amount of 5 to 30% by weight based on the total weight of the composition, but is not limited thereto.

The oil phase may further include an ester-based oil, a hydrocarbon-based oil, a vegetable oil, or a combination thereof.

The ester oil is ethylhexyl isononanoate, ethylhexyl isopalmitate, ethylhexyl isostearate, ethylhexyl myristate, isopropyl myristate, octyldodecyl myristate, ethylhexyl neopentanoate, trie Chilhexanoin, ethylhexyl oleate, ethylhexyl palmitate, ethylhexyl stearate, isononyl isononanoate, phytosteryl isostearyl dimerinoate, polyglyceryl-2 triisostearate, pentaerythrityl From the group consisting of tetraisostearate, cetylethylhexanoate, caprylic/capric triglyceride, butylene glycol dicaprylate/dicaprate, tocopherol acetate dicaprylic carbonate, and diisostearyl malate It may be one or more selected.

The hydrocarbon-based oil may be paraffin-based, olefin-based, squalane, or hydrogenated polydecene, but is not limited thereto.

As the vegetable oil, vegetable oils such as macadamia seed oil, meadow foam seed oil, olive oil, camellia oil, hazelnut oil, and argan oil, and waxes having a low melting point such as shea butter and hydrogenated vegetable oil may be used.

The oil phase may further include silicone oil. The silicone oil may be dimethicone, cyclomethicone, alkylsiloxane, cycloalkylsiloxane, etc., but is not limited thereto.

The cosmetic composition may include a surfactant. The surfactant may be any of a nonionic surfactant, an anionic surfactant, a cationic surfactant, a zwitterionic surfactant, and the like, and the type thereof is not limited. The surfactant may be included in the aqueous phase or oil phase depending on the type thereof. The surfactant may be included in an amount of 0.05 to 1% by weight, 0.05 to 0.5% by weight, 0.05 to 0.3% by weight, 0.1 to 1% by weight, 0.1 to 0.5% by weight, or 0.1 to 0.3% by weight based on the total weight of the composition.

The cosmetic composition may further include a sunscreen. The sunscreen may be an organic sunscreen or an inorganic sunscreen. The type of the sunscreen is not particularly limited as long as it is a conventional component used in a cosmetic composition. Accordingly, the cosmetic composition may be a cosmetic composition for sunscreen.

The cosmetic composition may further add components such as antioxidants, preservatives, pH adjusters, humectants, and lubricants as necessary. In addition, the cosmetic 　 composition may further include a substance capable of providing essential nutrients to the skin auxiliary. The cosmetic composition may contain adjuvants including, but not limited to, natural fragrance, cosmetic fragrance, or plant extract.

The cosmetic composition may be used for skin, mucous membranes, scalp or hair. The cosmetic composition may include a basic cosmetic such as a softening lotion, a nutrient lotion, a cream, a pack, a gel, and a patch; color cosmetics such as lipstick, makeup base, and foundation; cleaning agents such as shampoo, conditioner, body cleanser, toothpaste, and mouthwash; It may be used as a hair conditioner such as hair tonic, gel, mousse, etc., and as a cosmetic for hair such as a hair conditioner and a hair dye, but is not limited thereto.

Another aspect provides a method for improving skin gloss or moisturizing a subject's skin comprising administering to the subject in need thereof an effective amount of a zwitterionic chitosan derivative.

The term "effective amount" means an amount effective enough to produce the above-mentioned effects.

The terms "administering", "introducing", and "implanting" are used interchangeably and in one embodiment into a subject by a method or route that results in at least partial localization of the composition according to one embodiment to a desired site. It may mean the arrangement of the composition according to

Administration may be administered by methods known in the art. Administration may be administered directly to a subject by any means, for example, intravenous, intramuscular, oral, transdermal, mucosal, intranasal, intratracheal or subcutaneous administration. can The administration may be systemically or locally. The administration may be applied to the skin.

The subject may be a mammal, such as a human, cow, horse, pig, dog, sheep, goat, or cat. The subject may be an individual in need of improving skin condition, for example, improving skin gloss or moisturizing the skin.

Another aspect provides the use of a zwitterionic chitosan derivative for preparing a cosmetic composition for improving skin gloss or moisturizing the skin.

Details of skin gloss improvement, skin moisturizing, zwitterionic chitosan derivative, and cosmetic composition are as described above.

The cosmetic composition according to an aspect may exhibit an excellent skin gloss improvement or skin moisturizing effect by including a zwitterionic chitosan derivative.

1 is a result of NMR analysis of sulfonated chitosan.
2 is a graph confirming the effect of improving the glossiness when Example 1 and Comparative Example 1 were applied to the inner skin of the forearm.
3 is a graph confirming the gloss improvement effect when Example 1 and Comparative Example 1 are applied to the facial skin.
4 is a graph showing the cytotoxicity test results of zwitterionic chitosan derivatives.
5 is a graph confirming the moisturizing improvement effect when Example 1 and Comparative Example 1 were applied to the skin.

Hereinafter, the present invention will be described in more detail through examples. However, these examples are for illustrative purposes only, and the scope of the present invention is not limited to these examples.

Preparation Example 1. Synthesis of zwitterionic chitosan derivative 1

Among the zwitterionic chitosan derivatives, sulfonated chitosan was synthesized as shown in Scheme 1 below. Sulfonated chitosan was synthesized by reacting 1,3-propanesultone with the amine group (-NH ₂ ) of chitosan.

[Scheme 1]

Specifically, 0.5 g of chitosan (viscosity: 200-800 cP (1 wt% acetic acid solution, 25°C), degree of acetylation: 75-85%, Sigma-Aldrich, Inc., USA) was dissolved in 40 mL 2% acetic acid solution After stirring, it was heated to 50 °C while stirring with a magnetic stirrer. 1,3-propanesultone (TCI, Japan) having the same number of moles (3.1 mmol, 1 equivalent) of the amine group of chitosan was added to the prepared chitosan solution, and stirring was continued for 16 hours. The reaction solution was precipitated with acetone to obtain a reactant, and a white solid was obtained through centrifugation. Then, the obtained reactant was dispersed in ethanol and washed for several minutes in a sonicator. The solid obtained by centrifugation again was dissolved in distilled water and then freeze-dried.

The obtained chitosan derivative into which sulfonic acid was introduced was dissolved in deuterium oxide (D ₂ O) at a concentration of 3 g/L and subjected to nuclear magnetic resonance ( ¹ H NMR, Varian NMR System) analysis at 500 MHz, and the results were 1 is shown.

1 is a result of NMR analysis of sulfonated chitosan.

As shown in FIG. 1 , after adding 1,3-propanesultone, a sulfonation reaction was performed, and peaks corresponding to a, b, and c of Scheme 1 were confirmed. Therefore, it was confirmed that sulfonated chitosan was prepared.

Preparation Example 2. Synthesis of zwitterionic chitosan derivatives 2

Among the zwitterionic chitosan derivatives, carboxylated chitosan was synthesized as shown in Scheme 2 below. Carboxylated chitosan was synthesized by reacting chloroacetic acid with an amine group (-NH ₂ ) of chitosan.

[Scheme 2]

Specifically, 8.5 equivalents of chlorinated acetic acid (26.35 mmol) was dissolved in distilled water, and the pH was adjusted to 7 using sodium hydroxide solution. 0.5 g of chitosan (viscosity: 200-800 cP (1 wt% acetic acid solution, 25°C), degree of acetylation: 75-85%, Sigma-Aldrich, Inc., USA) was added to the solution, and stirred with a magnetic stirrer and heated to 90 °C. The reaction time was 4 hours, and pH 7 was maintained by dropwise addition of 20% sodium carbonate solution every 30 minutes. The reaction solution was precipitated with ethanol to obtain a reactant, and a white solid was obtained through centrifugation. Then, the obtained product was dispersed in ethanol and washed for several minutes in a sonicator. The solid obtained by centrifugation again was vacuum-dried.

Preparation Example 3. Zwitterionic chitosan derivative synthesis 3

Among the zwitterionic chitosan derivatives, phosphorylated chitosan was synthesized as shown in Scheme 3 below. Phosphorylated chitosan was synthesized by reacting phenyl phosphoric acid with an amine group (-NH ₂ ) of chitosan.

[Scheme 3]

Specifically, 0.5 g of chitosan (viscosity: 200-800 cP (1 wt% acetic acid solution, 25° C.), degree of acetylation: 75-85%, Sigma-Aldrich, Inc., USA) was dissolved in 1% acetic acid solution. . After dissolving the same mass of phenyl phosphoric acid as chitosan in distilled water, it was added to the chitosan solution for 2 hours. The reaction was carried out while stirring with a magnetic stirrer. After raising the temperature of the reaction solution to 80 °C, formic acid in an amount corresponding to 37% by mass of the used chitosan was added for 1 hour, followed by stirring under reflux at the same temperature for 6 hours. It was dialyzed with distilled water for 2 days using a dialysis membrane having a cutoff molecular weight of 6-8 kDa, followed by freeze-drying.

The anion group introduction ratio of the zwitterionic chitosan derivative synthesized in Preparation Examples 1 to 3 was set to 90% or more. When the anionic group introduction ratio is 90% or more, the chitosan derivative may be well soluble in water.

On the other hand, as a result of introducing each anionic group of Preparation Examples 1 to 3 into chitosan, chloroacetic acid or phenylphosphoric acid ending in -COOH caused a condensation reaction with the hydroxyl group of chitosan to produce an ester byproduct. Therefore, the sulfonated chitosan of Preparation Example 1, which has the best reaction efficiency because there is no ester by-product, was used below.

Example 1 and Comparative Examples 1-3. Preparation of oil-in-water emulsion cosmetic composition

An oil-in-water emulsion cosmetic composition was prepared with the ingredients and contents (wt%) shown in Table 1 below.

Specifically, the raw materials corresponding to the aqueous phase except for the zwitterionic chitosan were measured in a beaker and uniformly mixed at a temperature of 75° C. using an emulsion mixer at 5000 rpm. Zwitterionic chitosan was slowly added in the phase of emulsifying and mixing the aqueous phase and mixed uniformly. Then, the raw materials corresponding to the oil phase were measured in a beaker and uniformly dissolved at a temperature of 75°C. The dissolved oil phase was slowly added to the aqueous phase and emulsified at 7000 rpm for 5 minutes using an emulsification mixer.

Comparative Example 1 contains 1 wt% of chitosan (viscosity: 200-800 cP (1 wt% acetic acid solution, 25°C), acetylation degree: 75-85%, Sigma-Aldrich, Inc., USA) without introducing an anionic group was used as

In Comparative Example 2, 0.5 wt% of sulfonated chitosan having an anionic group introduced ratio (ZD) of 50% was used.

In Comparative Example 3, 1 wt% of sulfonated chitosan having an anionic group introduced ratio (ZD) of 50% was used.

In Example 1, 1 wt% of sulfonated chitosan having an anionic group introduced ratio (ZD) of 90% was used.

division ingredient Comparative Example 1 Comparative Example 2 Comparative Example 3 Example 1 Awards Purified water remaining amount remaining amount remaining amount remaining amount 1,2-Hexanediol One One One One 1,3-butylene glycol 2 2 2 2 glycerin 7 7 7 7 Neat-chitosan One - - - Sulfonic acid-chitosan
(ZD=50%) - 0.5 One 0 Sulfonic acid-chitosan
(ZD=90%) - - - One paid cetearyl alcohol 0.8 0.8 0.8 0.8 Glyceryl Stearate SE 0.6 0.6 0.6 0.6 beeswax 0.3 0.3 0.3 0.3 Sorbitan Stearate 0.3 0.3 0.3 0.3 Cetylethylhexanoate 4 4 4 4 Octyldodecyl Myristate 1.5 1.5 1.5 1.5 squalane 3.5 3.5 3.5 3.5 Polysorbate 60 1.2 1.2 1.2 1.2 Sorbitan Sesquioleate 0.4 0.4 0.4 0.4 etc embalming dose dose dose dose Sum 100 100 100 100

In Comparative Examples 2 and 3, zwitterionic chitosan (ZD=50%) did not dissolve well in water, so it was not possible to prepare a stable emulsion.

In addition, the viscosity of the cosmetic compositions of Example 1 and Comparative Examples 1 to 3 was measured. Viscosity was measured with a Brookfield DV2TLV equipped with an LV 64 spindle at 30 rpm for 1 minute. As a result, in the case of Example 1, the viscosity value was greatly increased to 3,000 cPs using zwitterionic chitosan (ZD=90%). On the other hand, Comparative Examples 1 to 3 had a viscosity value of 200 to 300 cPS. Therefore, it was experimentally demonstrated that zwitterionic chitosan can also serve as a viscosity-forming agent.

Experimental Example 1. Evaluation of skin luster improvement

In this experiment, in order to measure the effect of improving the skin's immediate luster, the compositions of Example 1 and Comparative Example 1 were applied to the inner skin of the forearm and the facial skin, and then a skin Gloss meter (Delfin, Finland) and VISIA-CR (Canfield Scientific, Inc., USA) using the equipment was observed for skin gloss (Skin Gloss Unit).

2 is a graph confirming the effect of improving the glossiness when Example 1 and Comparative Example 1 were applied to the inner skin of the forearm.

3 is a graph confirming the gloss improvement effect when Example 1 and Comparative Example 1 are applied to the facial skin.

2 and 3, the gloss increase rate of Example 1 containing the zwitterionic chitosan derivative was 17.7%, and the gloss increase rate of Comparative Example 1 containing chitosan was 6.3%. That is, Example 1 containing the zwitterionic chitosan derivative showed 2.8 times superior skin gloss improvement effect compared to the gloss increase rate of Comparative Example 1.

Experimental Example 2. Cytotoxicity test

Human keratinocytes HaCaT cells were cultured under defined conditions. The evaluation method is as follows. HaCaT cells were suspended in DMEM medium containing 10% FBS, inoculated into a 96-well plate at 1x10 ⁴ cells/well, and cultured until adhered to the bottom of the well. The medium was removed and a DMEM medium containing a zwitterionic chitosan derivative at a concentration of 0.3 μg/ml, 3 μg/ml, 30 μg/ml or 300 μg/ml was added, and 5% CO ₂ , 37° C. for 24 hours. cultured. Then, in order to confirm the cytotoxic effect, MTT (3-(4,5-dimetylthiazol-2-yl)2,5-diphenyltetrazolium bromide) dissolved in DPBS (Dulbecco's phosphate-buffered saline) was added and reacted by adding 20 μl per well. MTT is a pale yellow substrate and turns dark blue by the respiratory chain enzyme in the mitochondria of living cells. After 4 hours, the reaction solution was discarded and DMSO was added to measure the absorbance at 570 nm using a microplate reader for the changed color.

4 is a graph showing the cytotoxicity test results of zwitterionic chitosan derivatives.

As shown in FIG. 4 , the reduction of cells by the zwitterionic chitosan derivative was not observed. Therefore, it was confirmed that the zwitterionic chitosan derivative has no cytotoxicity.

Experimental Example 3. Moisture improvement experiment

In this experiment, in order to measure the immediate moisturizing effect of the zwitterionic chitosan derivative on the skin, the composition of Example 1 was applied to the skin, and then the skin moisture level was observed using Epsilon.

Specifically, the composition of Example 1 was applied to the arms of 5 subjects to measure the moisture level of the skin. As a control group, Comparative Example 1 and the uncoated group were used.

5 is a graph confirming the moisturizing improvement effect when Example 1 and Comparative Example 1 were applied to the skin.

As shown in FIG. 5 , it was confirmed that the skin moisture content increased by about two times immediately after the composition of Example 1 was applied to the skin, and it was found that the increase in skin moisture content was significantly higher even when compared to the non-applied group or the control group. could In addition, compared to Comparative Example 1, it was confirmed that the moisture retention was improved by about 10%.

Therefore, the cosmetic composition comprising the zwitterionic chitosan derivative according to an embodiment can immediately enhance skin moisture, and thus is effective in improving skin moisture and strengthening the skin barrier.

Example 2. Preparation of oil-in-water emulsion cosmetic composition for UV protection

An oil-in-water emulsion cosmetic composition for UV protection was prepared with the ingredients and contents (wt%) shown in Table 2 below.

Specifically, the raw materials corresponding to the aqueous phase except for the zwitterionic chitosan were measured in a beaker and uniformly mixed at a temperature of 75° C. using an emulsion mixer at 5000 rpm. Zwitterionic chitosan was slowly added in the phase of emulsifying and mixing the aqueous phase and mixed uniformly. Then, the raw materials corresponding to the oil phase were measured in a beaker and uniformly dissolved at a temperature of 75°C. The dissolved oil phase was slowly added to the aqueous phase and emulsified for 5 minutes at 7000 rpm using an emulsification mixer. Polysorbate 60 was used as a surfactant.

division ingredient Example 2 Awards Purified water remaining amount tromethamine 0.14 pentylene glycol One 1,2-Hexanediol One glycerin 3 dipropylene glycol 3 Polysorbate 60 0.5 Carbomer 0.2 Zwitterion-chitosan
(SD=90%) One paid Polyglyceryl-6 Stearate/Polyglyceryl-6 Behenate 0.5 phenethyl benzoate 3 Diethylaminohydroxybenzoylhexylbenzoate 2 Ethylhexyltriazone One titanium dioxide 10 caprylyl methicone 2 Dicaprylyl Ether 3 Phenyltrimethicone 5 etc embalming dose Sum 100

As a result, it was confirmed that the oil-in-water emulsion cosmetic composition for UV protection of Example 2 was successfully prepared.

Example 3. Preparation of oil-in-water emulsion cosmetic composition for UV protection

An oil-in-water emulsion cosmetic composition for UV protection was prepared with the ingredients and contents (wt%) shown in Table 3 below.

Specifically, a cosmetic composition was prepared according to the same method as in Example 2. C14-22 alcohol/C12-20 alkyl glucoside was used as a surfactant.

division ingredient Example 3 Awards Purified water remaining amount pentylene glycol One 1,2-Hexanediol 2 glycerin 3 dipropylene glycol 3 silica One tromethamine 0.45 acrylate copolymer 0.6 Zwitterion-chitosan
(SD=90%) 0.7 paid Bis-ethylhexyloxyphenol methoxyphenyltriazine 3 Ethylhexyltriazone 2 Diethylaminohydroxybenzoylhexylbenzoate 3.5 Isoamyl p-methoxycinnamate One Polysilicon-15 One dibutyl adipate 6 Dicaprylyl Carbonate 8 C14-22 alcohol/C12-20 alkyl glucoside 0.2 etc embalming dose Sum 100

As a result, it was confirmed that the oil-in-water emulsion cosmetic composition for UV protection of Example 3 was successfully prepared.

The description of the present invention described above is for illustration, and those of ordinary skill in the art to which the present invention pertains can understand that it can be easily modified into other specific forms without changing the technical spirit or essential features of the present invention. will be. Therefore, it should be understood that the embodiments described above are illustrative in all respects and not restrictive.

Claims (10)

A cosmetic composition for improving skin gloss or moisturizing the skin comprising a zwitterionic chitosan derivative. The cosmetic composition according to claim 1, wherein the zwitterionic chitosan derivative comprises a repeating unit represented by the following formula (1).
[Formula 1]

(In Formula 1, X is the same or different from each other in each repeating unit and is each independently H, -COCH ₃ or an anionic moiety.) The method according to claim 2, wherein the anionic moiety is any one selected from the group consisting of -RSO ₃ H, -RCOOH and -RPO ₂ HR', wherein R and R' are each independently substituted or unsubstituted C1-C20 of an aliphatic or aromatic hydrocarbon group. The cosmetic composition of claim 2, wherein the zwitterionic chitosan derivative has a total number of repeating units of 10 to 1,000. The cosmetic composition according to claim 2, wherein the proportion of the repeating units in which X is an anionic moiety in Formula 1 among the total number of repeating units of the zwitterionic chitosan derivative is 60 to 99%. The cosmetic composition according to claim 1, wherein the zwitterionic chitosan derivative is included in an amount of 0.1 to 10% by weight based on the total weight of the composition. The method according to claim 1, wherein the aqueous phase comprising a zwitterionic chitosan derivative; And a cosmetic composition that is an oil-in-water emulsion formulation comprising an oil phase. The cosmetic composition of claim 7, wherein the aqueous phase further comprises a polyol. The cosmetic composition of claim 7, wherein the oily part further comprises an ester-based oil, a hydrocarbon-based oil, a vegetable oil, or a combination thereof. The cosmetic composition of claim 7, further comprising a sunscreen.

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