KR20180108228A - Cosmetics compositions for skin whitening - Google Patents

Abstract

The present invention relates to a cosmetic composition for skin whitening. The cosmetic composition for skin whitening according to the present invention contains a skin whitening component with a specific functional group capable of covalent-bonding with protein residues on the surface of the skin, thereby forming the covalent bond with the skin without damaging the skin and providing a desired semi-permanent skin whitening effect.

Description

[0001] Cosmetics compositions for skin whitening [0002]

The present invention relates to a skin whitening component and a cosmetic composition for skin whitening.

The whitening function of cosmetics refers to making the efficacious ingredient into its original skin color by brightening the skin color or tone of a person, or by continuously using it to cover and define the defects of the skin such as spots and the like. To prevent the formation of melanin by inhibiting the expression of tyrosinase, it induces a mechanism that interferes with the transfer of melanin. However, in order to obtain a whitening effect, it must be continuously used during the turnover period (28 days during which the exfoliation of the skin is regenerated) There is a drawback to this. In addition, when the cosmetic is applied to the skin, components which do not have affinity for the skin or hair are easily removed during cleaning or daily life, and thus it is difficult to obtain the actual efficacy. On the other hand, in order to obtain an immediate effect, white cosmetics or color cosmetics are used for skin external use to temporarily lighten the tone of the skin, but this method is also easily removed during cleaning and daily use.

In order to improve the disadvantages, various mechanisms such as lipids, ceramides, surfactants, minerals imparting skin-affinity, and techniques for improving skin permeability, which have affinity with surfaces including skin and hair, There is a method of invading, but there is a limit in that the amount remaining in the skin is only a small amount and the effect is also temporarily maintained. Recently, a method of chemically modifying skin and hair surfaces of cosmetic materials has been introduced by using a bioconjugation method. If the horny layer is modified to provide a cosmetic effect by this method, the cosmetic effect can be maintained semi-permanently until desquamation occurs, and it can be easily removed by peeling if necessary.

Recently, a method has been proposed in which the skin is modified with alkoxysilane introduced with amine group in L'Oreal to quickly obtain the artificial tanning effect of dihydroxyacetone (DHA) (Patent Document 1). However, since alkoxysilane has good reactivity, It is classified into three classes and it is difficult to be applied to a practical product. Although prior art studies of Patent Document 2 and Patent Document 3 have proposed a method of modifying the skin, techniques for applying the bioconjugation method to cosmetics are still in an early stage so far.

The inventors of the present invention have devised a method for modifying amine groups, carboxy groups, cholol groups, hydroxyl groups, and the like in skin proteins through prior studies. In particular, a method of directly modifying proteins existing in hair and skin (Patent Document 4) using a polymeric carbodiimide (PCI) has been found and is being applied to a personal care application. The carbodiimide reaction can be minimized by the use of polymeric carbodiimide since acylurea is formed and can be toxic to the human body. However, since there is not a variety of reaction promoters such as PCI that can apply the reaction to the skin, it is necessary to have a reaction medium that can remain in the human body for a long time while the efficacious substance can remain on the skin in order to universally apply the bioconjugation method Do.

U.S. Published Patent Application No. 2010-516546 U.S. Published Patent Application No. 2011-0274639 U.S. Published Patent Application No. 2006-0233729 Korean Patent Publication No. 2008-0064467

It is an object of the present invention to provide a cosmetic composition for skin whitening that can effectively and permanently impart a permanent whitening effect without damaging the skin.

As a means for solving the above problems, the present invention provides a skin whitening cosmetic composition comprising a carbodiimide composition and a peptide bond formation promoting additive.

The cosmetic composition for skin whitening according to the present invention contains a reactive skin whitening component and / or a carbodiimide compound into which a specific functional group capable of covalently bonding with protein residues of the skin is incorporated, To provide a semi-permanent skin whitening effect.

FIG. 1 is a clinical result (n = 7, * p < 0.05) in which the brightness improvement rate of skin due to the two-week use of a cream-type mask pack containing glucosamine, a carbodiimide compound and a reaction promoting additive is quantified.
FIG. 2 is a clinical result (n = 20) in which the brightness improvement rate of the skin due to one week use of the cream pack type mask pack containing glucosamine, carbodiimide compound and reaction promoting additive is quantified through a questionnaire.
FIG. 3 is a clinical result (n = 7, * p < 0.05) in which the yellowness improvement rate of skin due to the two-week use of the cream pack type mask pack containing chitosan, carbodiimide compound and reaction promoting additive is quantified. .
Fig. 4 is a clinical result (n = 7, * p < 0.05) in which the rate of improvement in the skin's shine due to the two-week use of the cream pack type mask pack containing chitosan, carbodiimide compound and reaction promoting additive is quantified.

The present invention relates to a cosmetic composition for skin whitening comprising a carbodiimide compound, a reaction promoting additive and a skin whitening component.

The cosmetic composition for skin whitening according to the present invention can be prepared by, for example, reacting a known skin whitening ingredient with a carbodiimide compound and a reaction promoting additive to form a covalent bond with skin and protein, can do.

The carbodiimide compound is a generic term for compounds having a structure represented by the following formula (1) in the molecule, and is referred to as PCI in the present invention.

[Chemical Formula 1]

-N = C = N-

The carbodiimide compound preferably has at least 1 to 1000 structures represented by the formula (1), more preferably 1 to 100 structures represented by the formula (1) It is more preferable that the structure includes 1 to 10 structures in the molecule.

In this case, if the number of the carbodiimide groups represented by the formula (1) exceeds 1,000 in one molecule, the viscosity of the starting material is too large, the molecular weight is excessively large, the reaction position where the reaction can be performed becomes excessively large, The molecule having the bodymide group becomes too large, and the efficiency is lowered by blocking the portion showing the functional effect of the molecule having the substantial function.

In the present invention, a specific example of the carbodiimide compound may be a compound represented by the following formula (2), wherein n is 4 and m is 11 in the following formula (2): benzene, 1,3, Isocyanato-1-methylethyl) -, homopolymer, polyethylene glycol mono-ether-block (benzene, 1-isocyanato- Me-ether-blocked (hereinafter referred to as polymeric carbodiimide compound of formula (2)).

(2)

In the above formula (2), n is 1 to 100 and m is 1 to 100.

The carbodiimide compound may be used in an amount of 0.001 to 10 parts by weight, 0.01 to 7 parts by weight, or 0.1 to 5 parts by weight based on 100 parts by weight of the total composition. If the content is less than 0.001 part by weight, the whitening component is difficult to sufficiently adhere to the skin surface, and the continuous whitening effect is difficult to be exhibited. If the content exceeds 10 parts by weight, excessive amount of the carbodiimide compound Therefore, it is difficult to contribute to the efficacy, odor, and formability of the product, and there is a problem in formulation and stabilization of the formulation.

In the present invention, the term 'skin whitening effect' refers to a function of brightening the color or tone of the skin, cleansing the skin due to the improvement of the skin's luster, or covering the defects of the skin, it means. It also includes a tone control function to prevent aging or oxidation of the surface of the skin to prevent yellowing of the skin surface.

The reaction promoting additive for forming the peptide bond may be used in an amount of 0.0001 to 10 parts by weight based on 100 parts by weight of the total composition. Preferably 0.001 to 1 part by weight, more preferably 0.001 to 0.1 part by weight. If it is used in an amount exceeding 10 parts by weight, the rate of the chemical reaction is saturated, so that the product is not economical and does not contribute to the stability of the product. When it is used in an amount less than 0.0001, the whitening component adheres to the surface of the skin.

The reaction-promoting additive for forming the peptide bond specifically includes at least one selected from the group consisting of hydroxysuccinimide, hydroxycarboximide, hydroxytriazole, hydroxybenzotriazole, hydroxypyridinone, hydroxyphenylbenzimidazole, But are not limited to, one or more members selected from the group consisting of halide, hydroxybenzotriazine, and oxime. The reaction promoting additive may be in the form of a water-soluble nonionic polymer, a bead-shaped or resin-type polymer resin, or a silica bead in order to improve stability and biosafety in the formulation.

The water-soluble nonionic polymer preferably has a weight average molecular weight of 1,000 Da or more and less than 300,000 Da. When the molecular weight is more than 300,000 Da, the proportion of the carbodiimide compound inducing covalent bond is too small to exhibit the effect.

The water-soluble nonionic polymer may specifically be selected from the group consisting of polyethylene glycol, polyvinyl alcohol, polyethylene oxide, polyacrylonitrile, polyvinylpyrrolidone, polyisopropylacrylamide, cellulose derivatives, starch derivatives, dextran and guar gum And at least one polymer selected from the group consisting of

The resin-type polymer preferably has a weight-average molecular weight of 1,000 Da or more and less than 300,000 Da. When the molecular weight is more than 300,000 Da, the proportion of the carbodiimide compound inducing covalent bond is too small to exhibit the effect.

The bead-shaped polymer resin (polymer bead) preferably has an average particle diameter of 100 nm to 1 mm, preferably 100 nm to 100 μm, more preferably 1 μm to 100 μm, most preferably, 1 占 퐉 to 70 占 퐉. If the diameter of the polymer bead is less than 100 nm, safety problems may occur on the surface of the skin. If the diameter of the polymer bead is larger than 1 mm, there is a problem in formulation and stabilization.

The bead-shaped or resin-type polymer resin may specifically include a resin such as styrene, ethylene, butadiene, acrylonitrile, methylstyrene, terephthalate, ethylene chloride, ether ketone, etherimide, ether sulfone, phthalamide, phenylene ether, , Phenylene sulfide, sulfone, urethane, vinylidene fluoride, and tetrafluoroethylene.

The silica beads preferably have an average particle diameter of 100 nm to 1 mm, preferably 100 nm to 100 μm, more preferably 1 μm to 100 μm, most preferably 1 μm to 70 μm . If the diameter of the silica bead is less than 100 nm, it may cause safety problems on the skin and the surface. If the diameter of the silica bead is larger than 1 mm, there is a problem in formulation and stabilization.

The skin whitening ingredient used in the present invention may include a whitening ingredient capable of improving a damaged area due to deposition of melanin pigment in the skin such as extracts derived from natural materials such as copper, plants and minerals, amino acids, hormones, vitamins and the like , But is not limited thereto. For example, the component may be a hydroquinone compound; Vitamins such as niacinamide, vitamin C, and derivatives thereof; Flavonoid-based compounds such as moietine, hesperidine and the like; Resveratrol compounds and derivatives thereof; Carubbitacin derivatives; Glutaric acid, glutaric acid, glutaric acid, glutaric acid, glutaric acid, glutaric acid and glutaric acid; But are not limited to, arbutin, kojic acid, azelaic acid, alpha hydroxy acid, alpha-bisabolol, adenosine, ascorbyl glucoside, ascorbyl tetraisopalmitate, ethyl ascorbyl ether, fullerene, acetyl tyrosine, diacetyl benzoyl lactol, Magnesium stearate, magnesium ascorbyl phosphate, diosmetin, mace lignan, acetyl sphingosine, dihydroxymethoxaconic, alpha-bisabolol, protocatechuic aldehyde, orzanol, licorice extract, mulberry extract, green tea extract, Yeast extract, Lycopersicon esculentum extract, Wheat germ extract, Peony extract, Dried persimmon extract, Ginseng extract, Red ginseng extract, Saururus chinensis extract, Aglymoni extract, Indian Kannapuri extract, Jeju Sori extract, , Polylysine, glucosamine and derivatives thereof. Be greater than or equal to, but is not limited to this.

The skin whitening ingredient is preferably used in an amount of 0.001 to 50 parts by weight, 0.001 to 30 parts by weight, 0.01 to 10 parts by weight, or 0.1 to 5 parts by weight based on 100 parts by weight of the total cosmetic composition. When the content is less than 0.001, the effect is insufficient and there is a limit. When the content is more than 50 parts by weight, there is a problem in formulation and stabilization.

In particular, in the present invention, the skin whitening component can increase the reaction efficiency with the carbodiimide-based compound by containing a carboxyl group or an amine group in the molecule.

In addition, in the present invention, the skin whitening component may be one having a functional group capable of covalent bonding with protein residues on the skin surface.

The functional groups capable of forming a covalent bond with the protein residues include carbodiimide, imidoesters, aryl azides, diazirines, hydroxymethylphosphines, pentafluorophenyl esters, pyridyl disulfides, sulfo-hydroxysuccinimide esters, alkoxy The present invention relates to a process for the preparation of a compound of formula (I) wherein R 1 is selected from the group consisting of an amine, hydrazide, haloacetyl, azide, carbonate, aldehyde, propionaldehyde, butylaldehyde, nitrophenyl carbonate, aziridine, isocyanate, thiocyanate, epoxide, A group consisting of diesters, imidazoles, oxycarbonyl imidazoles, imines, thiols, maleimides, vinyl sulfones, ethyleneimines, thioethers, acrylonitriles, acrylic or methacrylic esters, disulfides, ketones, carboxylic acids and phosphates Lt; / RTI &gt; but is not limited to any of the above.

In addition, the protein may comprise reactive residues of thiol, hydroxyl, carboxyl or amine.

In a preferred embodiment of the cosmetic composition for skin whitening according to the present invention, a whitening component having a carboxyl group is directly made into a reactive ester whitening component having a bioreactivity, or an amino acid (for example, ex, aspartic acid, and glutamic acid) are reactively esterified to form a form that can be targeted by a skin whitening component including an amine group, thereby increasing the reaction efficiency, thereby significantly enhancing the effect. In a more preferred embodiment, the surface of the skin whitening component molecule or skin protein having a carboxyl group is firstly reacted with a polymeric carbodiimide compound first to form a reactive ester, and the reaction promoting additive is replaced with a reactive ester to increase selectivity , An excellent whitening effect can be obtained by reacting the formed reactive ester functional group with a whitening component having an amine in the molecule or reacting with an amine on the skin surface.

A skin whitening component molecule having a carboxyl group is firstly reacted with a carbodiimide compound to form a reactive ester, and the reaction promoting additive is substituted with a reactive ester to increase selectivity, and then the amino acid of the living body having an amine residue To form a covalent bond.

 [Reaction Scheme 1]

As shown in Reaction Scheme 2, asparaginic acid and glutamic acid, which are biogenic amino acids having a carboxyl group on the surface of a protein in the skin, first react with a carbodiimide compound to form a reactive ester, and the reaction promoting additive is substituted with a reactive ester to increase selectivity, And a reaction scheme with a whitening component having an amine residue to form a covalent bond.

 [Reaction Scheme 2]

Using the carbodiimide compound, the skin whitening component adhered to the skin by protein and peptide bond can be permanently attached to the skin without being removed from the skin by the shampoo, soap and cleanser.

By adding a reaction promoting additive to carbodiimide compound, the reaction efficiency of skin protein and whitening ingredient is increased. The reactive whitening ingredient bonded to the skin does not come off well during general washing due to soap, and is almost permanently attached to skin Can be maintained.

The present invention also relates to a composition for the skin whitening composition which comprises at least one compound selected from the group consisting of carbodiimide, imidoesters, aryl azides, diazylines, hydroxymethylphosphines, pentafluorophenyl esters, pyridyl disulfides, sulfo-hydroxysuccinimide esters, , Hydrazide, haloacetyl, azide, carbonate, aldehyde, propionaldehyde, butylaldehyde, nitrophenyl carbonate, aziridine, isocyanate, thiocyanate, epoxide, tresylate, succinimide, In the group consisting of an ester, an imidazole, an oxycarbonyl imidazole, an imine, a thiol, a maleimide, a vinyl sulfone, an ethyleneimine, a thioether, an acrylonitrile, an acrylic acid or methacrylic acid ester, a disulfide, a ketone, a carboxylic acid and a phosphate Reactive whitening with a functional group covalently bonded to at least one selected protein The can be included.

For example, as shown in Reaction Scheme 1, the reaction promoting additive after the first reaction of the carbodiimide compound may include a whitening component substituted. In addition, the present invention may include a skin whitening cosmetic composition comprising the whitening component substituted with the reaction promoting additive.

In order to further enhance the effect of the cosmetic composition for skin whitening according to the present invention, fatty acids such as palmitic acid and stearic acid, fatty alcohols, long-chain alkyl quaternary ammonium salts of straight chain and branched chain , Cationic polymers such as cationized polyvinylpyrrolidone, silicone, and the like may be used to facilitate the preparation. In order to formulate the composition into a cosmetic preparation, it is also possible to formulate cosmetics such as a solvent, a surfactant, a thickener, a stabilizer, a preservative, a colorant, a pH adjuster, a metal ion sequestrant, a pearlizing agent, an appearance improver, an emollient, Components may be incidentally included. The ingredients for the formulation may be used in an amount of 40 to 99 parts by weight or 60 to 99 parts by weight based on 100 parts by weight of the total composition.

The cosmetic composition for skin whitening according to the present invention can be used for prescribing a cosmetic composition for skin whitening including a skin whitening component having a functional group. Examples of applications of skin products include cosmetics (such as lotion, serum, essence, lotion, cream), color cosmetics (makeup base, foundation, powder, eye shadow, lip gloss, lipstick, lip balm, etc.) , Cosmetics for cleansing (foam cleansing, cleansing oil, cleansing lotion, cleansing cream, cleansing gel, pack, mask, soap, cleansing tissue), sun care cosmetics, body cosmetics (body lotion, shower gel, body cream, Etc.).

More preferably, the cosmetic for whitening skin according to the present invention comprises a whitening component containing a carbodiimide compound and a reaction promoting additive and having a reactive functional group, and when the activity of the above-mentioned preparation is lowered in a water- It is easier to maintain its activity in the formulation, and it can be mixed with a buffer for pH control just before use, or can be made to react with water in a cleaning process. Examples of non-aqueous formulations include liquid, sheet, powder, tablet, oil, wax, ampoule, gel and the like which are used as ordinary non-aqueous cosmetic preparations. In addition, the carbodiimide compound, the reaction promoting additive, and the whitening component can be formulated in a single form or two separate forms in an encapsulated form. In addition, a method of blocking a derivative in which a reactive functional group and a whitening functional component are combined through encapsulation from water may also be used.

In order to increase the whitening effect having a functional group in the skin whitening cosmetic composition according to the present invention, it is preferable to use 2-basic acid esters such as dioctylsuccinate, dioctyl adipate and diethyl sebacate, polyols, polyethylene glycol, propylene glycol, Hexylene glycol, butanediol, and isomers thereof, glycerol, benzyl alcohol, ethoxydiglycol and derivatives thereof. The above-mentioned solvents increase the permeability of hair or skin and are used as a solvent of a poorly soluble substance. More preferably, the solvent used for increasing the activity maintaining effect of a whitening component having a functional group includes diethyl sebacate, ethoxy glycol, bis-ethoxy glycol cyclohexane 1,4-dicarboxylate and the like.

Hereinafter, the present invention will be described in detail by the following examples. However, the following examples are illustrative of the present invention, and the present invention is not limited to the following examples.

Example  1 and Comparative Example  1, 2: Cream ( 100 g ) Preparation of mask pack for formulation

A cream pack type mask pack was prepared with the composition and contents shown in Table 1 below.

The raw materials 3 to 13 were heated to 70 ° C and homogeneously mixed at 1500 rpm for 5 minutes using a homomixer. The oil phase components 15 to 24 dissolved in advance by heating at 70 DEG C were added to the mixed water phase and homogeneously mixed at 3500 rpm for 5 minutes using a homomixer. Thereafter, the temperature was lowered to 50 캜, and a solution containing a neutralizing agent, a carbodiimide compound benzene, 1,3-bis (1-isocyanato-1-methylethyl) -, a homopolymer, a polyethylene glycol mono-ether- 1, Peptide Bond Formation Promotion Additive (Reaction Promotion Additive) PS-HOBt 2 and Fragrance 14 were homogeneously mixed with a homomixer for 3 minutes, followed by defoaming, filtration and cooling.

Hydroxybenzotriazole PS-HOBt (Hydroxybenzotriazole) is a polymer resin having a size of 10 μm bonded to Hydroxybenzotriazole. The polymer resin has a molar ratio of (m + n + x + y): z = 99: 1 ) Of beads of 10 um consisting of polystyrene. The repeating units of z below are crosslinkers that are not attached to a particular site and link randomly between polymers, and are described in Tetrahedron Letters 41 (2000) 2463-2466 and / or Chem. Rev. 2011, 111, 6557-6602.

(3)

.

No ingredient Example 1 Comparative Example 1 Comparative Example 2 One Benzene, 1,3, -bis (1-isocyanato-1-methylethyl) -, homopolymers, polyethylene glycol mono-ether- 0.1 - 0.1 2 PS-HOBt 0.1 0.1 - 3 Glucosamine 1.0 1.0 1.0 4 glycerin 6.0 6.0 6.0 5 DPG 3.0 3.0 3.0 6 1,3-butylene glycol 2.0 2.0 2.0 7 Urea / HEPES 0.8 0.8 0.8 8 antiseptic 1.0 1.0 1.0 9 Anti-inflammatory agent 2.0 2.0 2.0 10 Carbomer 0.2 0.2 0.2 11 Xanthan gum 0.05 0.05 0.05 12 corrector 0.28 0.28 0.28 13 Purified water To 100 To 100 To 100 14 Beauty 0.1 0.1 0.1 15 Cetearyl alcohol 2.5 2.5 2.5 16 Glyceryl stearate 1.2 1.2 1.2 17 PEG-100 stearate 0.3 0.3 0.3 18 PEG-40 stearate 0.5 0.5 0.5 19 Stearic acid 0.3 0.3 0.3 20 Cyclohexasiloxane 6.0 6.0 6.0 21 Petaerythrityl tetraethylhexanoate 3.0 3.0 3.0 22 Dimethicone 5.0 5.0 5.0 23 Macadamia oil 2.0 2.0 2.0 24 Hydrogenated polydecene 4.0 4.0 4.0

Experimental Example  One

Glucosamine was attached to the skin by bioconjugation using a carbodiimide compound and a reaction promoting additive, and its efficacy was confirmed.

The mask pack formulations of Comparative Example 2 and Example 1 were each prepared and applied to 7 subjects to confirm the skin brightness change. The use of the mask pack was performed twice a day for two weeks by cleansing with a cleanser before use, and then applying the mask pack for 30 minutes and washing again. The skin brightness was checked with a LAB measuring instrument (Konica Minolta CR-300 Chroma Meter).

As a result of the experiment, it was confirmed that when the glucosamine was adhered to the skin using the carbodiimide compound and the reaction promoting additive (Example 1), the skin brightness was improved by 1.35% for 2 weeks (Fig. 1). The whitening effect of Example 1 was significantly improved as compared with Comparative Example 2 using only the carbodiimide compound.

Glucosamine as well as various whitening ingredients are attached to the skin by the bioconjugation method together with the reaction promoting additive, and it is expected to remain for a long time and to obtain the whitening effect continuously for a certain period of time

Experimental Example  2

Glucosamine was attached to the skin by bioconjugation using a carbodiimide compound and a reaction promoting additive, and its efficacy was confirmed.

The mask pack formulations of Comparative Example 2 and Example 1 were each prepared and applied to 20 subjects to confirm the skin brightness change. The use of a mask pack was performed by cleansing with a cleanser prior to use, and then once a day for one week by applying the mask pack for 30 minutes and washing again.

Changes in skin brightness were evaluated using a user questionnaire. Moisturizing, whitening, elasticity, etc. were set, and the degree of improvement in the user 's feeling was confirmed by comparing the results with those of ordinary users.

As a result of the experiment, it was confirmed that when the glucosamine was attached to the skin using the bioconjugation method using the carbodiimide compound and the reaction promoting additive, the brightness of the skin sensed by the user was improved by 80% or more over one week ]. The whitening effect of Example 1 was significantly improved as compared with Comparative Example 2.

Glucosamine as well as various whitening ingredients are attached to the skin by the bioconjugation method together with the reaction promoting additive, and it is expected to be retained for a long time to obtain the whitening effect continuously for a certain period of time.

Example  2

A mask pack was prepared in the same manner as in Example 1 except that chitosan was used instead of glucosamine in Example 1.

Comparative Example  3

A mask pack was prepared in the same manner as in Comparative Example 2, except that chitosan was used instead of glucosamine in Comparative Example 2.

Experimental Example  3

Chitosan was attached to the skin using a carbodiimide compound and a reaction promoting additive using bioconjugation, and the efficacy was confirmed. (Preventing aging or oxidation of the skin surface to reduce yellowing, thereby controlling the tone and confirming skin whitening effect)

The mask pack formulations of Example 2 and Comparative Example 3 were respectively prepared and applied to balls of seven subjects to confirm skin yellowness and gloss change as a measure of skin aging. The use of the mask pack was performed twice a day for two weeks by cleansing with a cleanser before use, and then applying the mask pack for 30 minutes and washing again. Yellowness was confirmed with a LAB measuring instrument (Konica Minolta CR-300 Chroma Meter) and the gloss change was confirmed with a gloss meter (C & K MPA 580, skin glossymeter GL200).

As a result, when the chitosan was adhered to the carbodiimide compound and the reaction promoting additive by the bioconjugation method (Example 2), the skin yellowness was 6.51% after 2 weeks of use due to the antioxidant and anti- , And it was confirmed that the skin luster was also improved by 5.43% after 2 weeks of use (FIGS. 3 and 4). The whitening effect of Example 2 using the carbodiimide compound and the reaction promoting additive was faster and significantly improved compared to Comparative Example 3 using only the carbodiimide compound.

It is anticipated that various effective substances as well as chitosan can be attached to the skin by the bioconjugation method and remain for a long time, thereby continuously obtaining the cosmetic effect for a certain period of time.

Example  3 and Comparative Example  4 ~ 6: Manufacture of nonwoven mask pack

Non-woven mask pack formulations were prepared with the compositions and contents shown in Table 2 below.

More specifically, the raw materials 1, 8, 9, 10, 11, 14, 15 and 16 were heated to 70 DEG C and homogeneously mixed at 1500 rpm for 5 minutes using a homomixer. The oil phase components 5, 6, 7, 12 and 13 dissolved in advance by heating to 70 were added to the mixed water phase and mixed homogeneously at 2000 rpm for 5 minutes using a homomixer. Thereafter, the temperature was lowered to 50 ° C and benzene, 1,3-bis (1-isocyanato-1-methylethyl) -, homopolymer, polyethylene glycol mono-ether- Glucosamine 4 and Flavor 17 were added and homogeneously mixed with a homomixer for 3 minutes, followed by defoaming, filtration and cooling. The nonwoven mask was then impregnated with the formulation.

No Raw material (% by weight) Glucosamine (2%) Example 3 Comparative Example 4 Comparative Example 5 Comparative Example 6 One Distilled water To 100 To 100 To 100 To 100 2 Benzene, 1,3, -bis (1-isocyanato-1-methylethyl) -, homopolymers, polyethylene glycol mono-ether- 0.1 - - 0.1 3 PS-HOBt 0.1 - 0.1 - 4 Glucosamine 1.0 1.0 1.0 1.0 5 Dimethicone 4.0 4.0 4.0 4.0 6 Pentaerythrityl
tetraethylhexanoate 3.0 3.0 3.0 3.0 7 Hydrogenated
polydecene 1.0 1.0 1.0 1.0 8 Sorbitol 3.0 3.0 3.0 3.0 9 DPG 7.0 7.0 7.0 7.0 10 1,3-butylene glycol 1.0 1.0 1.0 1.0 11 Glycerin 7.0 7.0 7.0 7.0 12 Bis-PEG-18
Methyl ether
dimethyl silane 2.0 2.0 2.0 2.0 13 Methyl glucose
sesquistearate 0.3 0.3 0.3 0.3 14 antiseptic 1.0 1.0 1.0 1.0 15 Anti-inflammatory agent 2.0 2.0 2.0 2.0 16 Hydroxyethylcellulose 0.4 0.4 0.4 0.4 17 Beauty 0.1 0.1 0.1 0.1

Experimental Example  4: Evaluation of skin brightness improvement

Glucosamine was attached to the skin by bioconjugation of a carbodiimide compound and a reaction promoting additive and its efficacy was confirmed. The mask pack formulations of Example 3 and Comparative Examples 4 to 6 were prepared and applied to 7 subjects to determine the skin brightness change.

The use of a mask pack was performed by cleansing with a cleanser prior to use, and then applying the mask pack for 30 minutes and washing again once a day for 2 weeks. The skin brightness was checked with a LAB measuring instrument (Konica Minolta CR-300 Chroma Meter).

Then, the difference (ΔL *) between the skin color at the measurement time point and the application start point of each of the test materials was calculated according to the following equation (1).

On the other hand, the whitening effect is judged by comparison of DELTA L * between the sample application site and the control site. When the DELTA L * value is 2, the whitening of the deposited pigment is noticeable. .

[Equation 1]

? L = L value at the time of measurement after application? L value at the start of application

division Glucosamine (2%) Example 3 Comparative Example 4 Comparative Example 5 Comparative Example 6 2 days 1.3 0.6 0.7 0.9 7 days 1.6 0.8 0.8 1.2 14 days 2.3 0.9 0.7 2.8

As shown in Table 3, the whitening effect of glucosamine by bioconjugation of the carbodiimide compound and the reaction promoting additive was significantly improved when the carbodiimide compound and the reaction promoting additive were used to improve the skin brightness for 2 weeks .

Glucosamine as well as various whitening substances are attached to the skin by bio-conjugation method and are expected to remain for a long time, so that the cosmetic effect can be continuously obtained for a certain period of time.

Claims (17)

A composition for dyeing comprising a carbodiimide compound, a reaction promoting additive and a skin whitening component.
The method according to claim 1,
Wherein the reaction promoting additive is selected from the group consisting of hydroxysuccinimide, hydroxycarboximide, hydroxytriazole, hydroxybenzotriazole, hydroxypyridinone, hydroxyphenylbenzimidazole, hydroxyindolinone, hydroxybenzotriazine And oxime. &Lt; / RTI &gt;
The method according to claim 1,
Wherein the reaction promoting additive is a water-soluble nonionic polymer, a polymer resin in bead form or resin form, or a form combined with silica beads.
The method of claim 3,
Wherein the water-soluble nonionic polymer has a weight average molecular weight of 1,000 Da or more and less than 300,000 Da.
The method of claim 3,
The water-soluble nonionic polymer may be at least one selected from the group consisting of polyethylene glycol, polyvinyl alcohol, polyethylene oxide, polyacrylonitrile, polyvinylpyrrolidone, polyisopropylacrylamide, cellulose derivatives, starch derivatives, dextran, Lt; RTI ID = 0.0 &gt; 1, &lt; / RTI &gt;
The method of claim 3,
Wherein the resin type polymer resin has a weight average molecular weight of 1,000 Da or more and less than 300,000 Da.
The method of claim 3,
The bead-shaped polymer resin is a cosmetic composition for skin whitening having an average particle diameter of 100 nm to 1 mm
The method of claim 3,
The bead or resin type polymer resin may be selected from the group consisting of styrene, ethylene, butadiene, acrylonitrile, methylstyrene, terephthalate, ethylene chloride, ether ketone, etherimide, ether sulfone, phthalamide, phenylene ether, Wherein the polymer is a polymer polymerized with monomers selected from the group consisting of rhenium sulfide, sulphone, urethane, vinylidene fluoride and tetrafluoroethylene.
The method of claim 3,
Wherein the silica bead has an average particle diameter of 100 nm to 1 mm.
The method according to claim 1,
Wherein the carbodiimide compound is 0.001 to 10 parts by weight based on 100 parts by weight of the total composition.
The method according to claim 1,
Wherein the peptide bond formation reaction promoting additive is 0.0001 to 10 parts by weight per 100 parts by weight of the total composition.
The method according to claim 1,
Wherein the skin whitening component comprises a carboxyl group or an amine group in the molecule.
The method according to claim 1,
The skin whitening component is selected from the group consisting of vitamins and derivatives thereof; Flavonoid compounds; Resveratrol compounds and derivatives thereof; Carubbitacin derivatives; Amino acid-based compounds; But are not limited to, arbutin, kojic acid, azelaic acid, alpha hydroxy acid, alpha-bisabolol, adenosine, ascorbyl glucoside, ascorbyl tetraisopalmitate, ethyl ascorbyl ether, fullerene, acetyl tyrosine, diacetyl benzoyl lactol, Magnesium stearate, magnesium ascorbyl phosphate, diosmetin, mace lignan, acetyl sphingosine, dihydroxymethoxaconic, alpha-bisabolol, protocatechuic aldehyde, orzanol, licorice extract, mulberry extract, green tea extract, Yeast extract, Lycopersicon esculentum extract, Wheat germ extract, Peony extract, Dried persimmon extract, Ginseng extract, Red ginseng extract, Saururus chinensis extract, Aglymoni extract, Indian Kannapuri extract, Jeju Sori extract, , Polylysine, glucosamine and derivatives thereof. A cosmetic composition for skin whitening or more.
The method according to claim 1,
Wherein the skin whitening component has a functional group capable of covalently bonding to protein residues on the skin surface.
15. The method of claim 14,
The functional groups covalently bonded to the protein include carbodiimide, imidoesters, aryl azides, diazylines, hydroxymethylphosphines, pentafluorophenyl esters, pyridyl disulfides, sulfo-hydroxysuccinimide esters, alkoxy amines, But are not limited to, hydrazide, haloacetyl, azide, carbonate, aldehyde, propionaldehyde, butylaldehyde, nitrophenyl carbonate, aziridine, isocyanate, thiocyanate, epoxide, tresylate, succinimide, Selected from the group consisting of imidazole, oxycarbonylamidazole, imine, thiol, maleimide, vinylsulfone, ethyleneimine, thioether, acrylonitrile, acrylic acid or methacrylic acid ester, disulfide, ketone, carboxylic acid and phosphate At least one cosmetic composition for skin whitening.
The method according to claim 1,
Wherein the skin whitening component is 0.001 to 50 parts by weight per 100 parts by weight of the total composition.
The method according to claim 1,
A carbodiimide compound, a reaction promoting additive, and a skin whitening ingredient are encapsulated in a single formulation; A composition for dyeing two formulations in which a carbodiimide compound, a reaction promoting additive, and a skin whitening component are separated.

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