KR20170062957A - 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 whitening component having a specific functional group capable of covalent bonding with protein residues on the surface of the skin to form a covalent bond without damaging the skin, thereby providing a desired whitening effect semi-permanently.

Description

[0001] Cosmetics compositions for skin whitening [0002]

The present invention relates to a reactive skin whitening component to which a functional group binding to a protein is bound 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 which is capable of continuously imparting a permanent whitening effect without damaging the skin.

As means for solving the above problems, the present invention relates to a phosphonium compound; And a skin whitening component.

As another means for solving the above problems, the present invention provides a skin whitening cosmetic composition further comprising a peptide binding-promoting additive in the composition.

The cosmetic composition for skin whitening according to the present invention contains a reactive skin whitening component and / or a phosphonium-based compound into which a specific functional group capable of covalent bonding with the protein residues of the skin is incorporated, thereby forming a covalent bond without damaging the skin, Provides a skin whitening effect. It also provides an effective whitening effect, including a peptide bond formation promoting additive.

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

The present invention relates to a skin whitening cosmetic composition comprising a phosphonium compound and a skin whitening component.

The cosmetic composition for skin skin whitening according to the present invention can be prepared by, for example, reacting a known phosphatid-based compound with a skin whitening component to form a covalent bond with the protein of the skin through a reactive whitening component bonded with phosphonium, The effect can be maximized.

The phosphonium 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 entire cosmetic composition. If the content is less than 0.001 part by weight, there is a problem that continuous skin whitening effect is hardly exhibited. If the content is more than 10 parts by weight, the phosphonium compound, which exists excessively above the reaction site existing in the skin, And thus can not function to improve persistence and can act as a lost component.

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 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 phosphonium-based compound by including 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 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, oxycarbonyl imidazole, imine, thiol, maleimide, vinyl sulfone, ethyleneimine, thioether, acrylonitrile, acrylic acid or methacrylic acid ester, disulfide, ketone, carboxylic acid and phosphate It may be more than one, but it is not limited anymore.

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

The phosphonium-based compound may be a compound represented by the following Formula 1:

[Chemical Formula 1]

In Formula 1,

R1 represents a water-soluble nonionic polymer, a polymer resin in bead or resin form, or a silica bead,

R ₂ is selected from the group consisting of benzotriazole-yloxy, azabenzotriazole-yloxy, nitrobenzotriazole-yloxy, pentafluoropenyl- -O-), pyridylthio, hydrooxobenzotriazin, cyanoethoxycarbonylmethylidene and halogen, and the substituent may be selected from the group consisting of hydrogen,

R ₃ to R ₅ are the same or different from each other and are a dialkylamino compound or a heterocycloamine compound.

The dialkylamino compound may be a compound having 1 to 10 carbon atoms and preferably has 3 or less carbon atoms. The heterocyclic amine compound may be a compound having 2 to 10 carbon atoms and preferably 3 to 6 carbon atoms.

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 300,000 Da or more, the proportion of the phosphonium compound that induces covalent bond is too small to exhibit the efficacy.

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 bead or 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 300,000 Da or more, the proportion of the phosphonium compound that induces covalent bond is too small to exhibit the efficacy.

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 polymer 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 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 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 . When the diameter of the silica beads is less than 100 nm, safety problems may occur on the surface of the skin. If the diameter of the silica beads is larger than 1 mm, there is a problem in formulation and stabilization.

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 phosphonium compound of formula (1) first to form a reactive ester, and the reactive ester functional group An excellent whitening effect can be obtained by reacting a whitening component or reacting with an amine on the skin surface.

In the following Reaction Scheme 1, the skin whitening component molecule having a carboxyl group is firstly reacted with a phosphonium compound to form a reactive ester, followed by reaction with an amino acid 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 skin protein, react first with a phosphonium compound to form a reactive ester, and then react with a whitening component having an amine residue to form a covalent bond Fig.

In the following Reaction Scheme 2, asparaginic acid and glutamic acid, which are carboxylamino group-bearing biogenic amino acids on the protein surface of skin, first react with a phosphonium compound to form a reactive ester, and then react with a whitening component having an amine residue to form a covalent bond. Respectively.

[Reaction Scheme 2]

Using the phosphonium compound, the skin whitening component adhered to the skin by the protein and peptide bond can be maintained permanently attached to the skin without being removed from the skin by a cleaning method such as a soap and a cleanser.

The reactive whitening component bound to the skin increases the reaction efficiency of the protein and whitening component of the skin by the phosphonium-based compound, so that it does not come off well during general cleaning due to soap, and can be maintained almost permanently attached to the skin .

The present invention also relates to a composition for the skin whitening component which comprises at least one compound selected from the group consisting of carbodiimide, imidoesters, aryl azides, diazirines, hydroxymethylphosphines, pentafluorophenyl esters, pyridyl disulfides, sulfo- , 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 a 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, a phosphonium compound produced by a first-step reaction of a phosphonium-based compound may include a whitening component bonded thereto. In addition, the present invention may include a skin whitening cosmetic composition containing the above-mentioned reactive whitening component.

In the cosmetic composition for skin whitening according to the present invention, it is preferable that the cosmetic composition for skin whitening comprises at least one compound selected from the group consisting of a hydroxysuccinimide compound, a hydroxycarboximide compound, a hydroxy triazole compound, a hydroxybenzotriazole compound, a hydroxypyridinone compound, At least one peptide bond formation reaction promoting additive selected from the group consisting of an imidazole-based compound, a hydroxyindoline-based compound, a hydroxybenzotriazine-based compound, and oxime. The term "system compound" means, for example, in the case of a hydroxybenzotriazole-based compound, to include all compounds having hydroxybenzotriazole and hydroxybenzotriazole.

The peptide bond formation reaction promoting additive 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. Even if 10 parts by weight or more is used, 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 used below 0.0001, little or no help is given to reactivity.

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 based on 100 parts by weight of the total composition.

The skin whitening cosmetic composition according to the present invention can be used for the formulation of a whitening cosmetic composition including a whitening function component having a functional group. Examples of application of the hair product include a shampoo composition, a shampoo, a rinse, a treatment, a wax, a gel, a spray, a mousse, a hair lotion, a hair pack, a hair essence, a hair cream, a research hair dye, Non-woven fabric, sheet, and the like. Application examples of the skin product generally include basic cosmetics (lotion, serum, essence, lotion, cream, etc.) for arranging and protecting skin, color cosmetics (makeup base, foundation, powder, Cleansing lotion, cleansing cream, cleansing gel, pack, cosmetics, etc.), makeup for hand and toenails (manicure, nutrient, Mask, soap, cleansing tissue, etc.), sun care cosmetics, body cosmetics (body lotion, shower gel, body cream, body oil, etc.).

More preferably, the cosmetic for whitening skin according to the present invention contains a whitening component having a reactive functional group at the same time as containing a phosphonium compound. When the activity of the above-mentioned preparation is lowered in a water-based form, It may be easier to maintain, and may be mixed with a buffer for pH control just before use, or may be brought into contact with water during the washing 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 phosphonium-based compound and the whitening component can be formulated as a single agent in an encapsulated form or as two separate forms of each. 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 to 2 and Comparative Example  1: 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. After the temperature was lowered to 50 ° C, a neutralizing agent, 1-hydroxybenzotriazole (HOBt), a phosphonium-based compound, Benzotriazol- 2 and Fragrance 14 were homogeneously mixed with a homomixer for 3 minutes, followed by degassing, filtration and cooling.

The PS-BOP is a polymer resin having a weight average molecular weight of 200,000 Da, represented by the formula (1), wherein R ₁ is represented by the following formula 2 (m + n + x + y: z = 99: 1) ; R ₂ is benzotriazole-yloxy; R ₃ to R ₅ are dimethylamino. Z is a crosslinker that is not attached to a specific site but connects randomly between polymers, and Eur . J. Org . Chem . 2004, 1936_1939.

(2)

No ingredient Example 1 Example 2 Comparative Example 1 One PS-BOP 0.1 0.1 - 2 HOBt 0.01 0.01 0.01 3 Glucosamine 2.0 1.0 2.0 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 phosphonium compound and its efficacy was confirmed.

The mask pack formulations of Comparative Example 1 and Example 1 were respectively prepared and applied to 7 subjects to check 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 using the phosphonium compound (Example 1), the skin brightness was improved by 1.18% for 2 weeks (Fig. 1). The whitening effect of Example 1 was significantly improved as compared with Comparative Example 1.

Glucosamine as well as various whitening ingredients are attached to the skin by bio-conjugation method and are expected to remain for a long time to obtain a whitening effect continuously for a certain period of time

Experimental Example  2

Glucosamine was attached to the skin by bioconjugation using a phosphonium compound and its efficacy was confirmed.

The mask pack formulations of Comparative Example 1 and Example 1 were respectively prepared and applied to 20 subjects to check 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 improvement of user 's feeling was confirmed by X when it was similar to usual, and O when it was feeling better.

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

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

Example  3

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

Comparative Example  2

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

Experimental Example  3

Chitosan was attached to the skin using biosorption of phosphonium compounds and its 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 Comparative Example 2 and Example 3 were respectively prepared and applied to balls of 7 subjects to check 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, it was confirmed that the skin yellowness was improved by 5.82% after 2 weeks of use due to the antioxidant and anti-aging ability of chitosan when the chitosan was adhered using the phosphonium compound biocontacting method (Example 3) It was confirmed that the skin luster was also improved by 4.98% after 2 weeks of use (FIGS. 3 and 4). The whitening effect of Example 3 was significantly improved as compared with Comparative Example 2.

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  4 to 5 and Comparative Example  3 ~ 4: 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 at 70 占 폚 were added to the mixed aqueous phase and mixed homogeneously at 2000 rpm for 5 minutes using a homomixer. Thereafter, the temperature was lowered to 50 캜, PS-BOP 2, HOBt 3, glucosamine 4 and flavor 17 were added, homogeneously mixed with a homomixer for 3 minutes, and defoamed, filtered and cooled. The nonwoven mask was then impregnated with the formulation.

No Raw material (% by weight) Glucosamine (2%) Comparative Example 3 Example 4 Comparative Example 4 Example 5 One Distilled water To 100 To 100 To 100 To 100 2 PS-BOP - 0.1 - 0.1 3 HOBt - - 0.01 0.01 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 using the bioconjugation of a phosphonium compound and its efficacy was confirmed. The mask pack formulations of Comparative Examples 3 to 4 and Examples 4 to 5 were prepared and applied to 7 subjects to check 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 (L *) of skin color between the measurement time point and the application start point of each of the test materials was calculated according to the following equation (1), and the results are shown in Table 3 below.

On the other hand, the whitening effect is judged by comparing the L * values of the sample application site and the control site. When the L * value is 2, the whitening of the deposited pigment is noticeable. When the L * value is 1.5 or more, .

[Equation 1]

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

division Glucosamine (2%) Comparative Example 3 Example 4 Comparative Example 4 Example 5 2 days 0.5 0.6 0.5 1.1 7 days 0.5 1.0 0.6 1.8 14 days 0.8 1.4 0.5 2.1

As shown in Table 3, the whitening effect of glucosamine by bioconjugation of the phosphonium-based compound was confirmed to be remarkably improved when the PS-BOP and PS-HOBt were used to improve the skin brightness for two 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 cosmetic composition for skin whitening comprising a phosphonium compound and a skin whitening component.
The method according to claim 1,
Wherein the phosphonium-based compound is a compound represented by the following Formula 1:
[Chemical Formula 1]

In Formula 1,
R ₁ represents a water-soluble nonionic polymer, a polymer resin in bead or resin form, or a silica bead,
R ₂ is selected from the group consisting of benzotriazole-yloxy, azabenzotriazole-yloxy, nitrobenzotriazole-yloxy, pentafluoropenyl- -O-), pyridylthio, hydrooxobenzotriazin, cyanoethoxycarbonylmethylidene and halogen, and the substituent may be selected from the group consisting of hydrogen,
R ₃ to R ₅ are the same or different and each is a dialkylamino compound having 1 to 10 carbon atoms or a heterocycloamine compound having 2 to 10 carbon atoms.
3. The method of claim 2,
Wherein the water-soluble nonionic polymer has a weight average molecular weight of 1,000 Da or more and less than 300,000 Da.
3. The method of claim 2,
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;
3. The method of claim 2,
Wherein the bead or resin type polymer resin has a weight average molecular weight of 1,000 Da or more and less than 300,000 Da.
3. The method of claim 2,
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.
3. The method of claim 2,
Wherein the silica bead has an average particle diameter of 100 nm to 1 mm.
The method according to claim 1,
Wherein the phosphonium compound is 0.001 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.
12. The method of claim 11,
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.
In the first aspect,
Wherein the skin whitening component is 0.001 to 50 parts by weight per 100 parts by weight of the total composition.
In the first aspect,
Wherein the composition further comprises a peptide bond formation reaction promoting additive.
15. The method of claim 14,
The peptide bond formation reaction promoting additive may be at least one compound selected from the group consisting of a hydroxysuccinimide compound, a hydroxycarboximide compound, a hydroxytriazole compound, a hydroxybenzotriazole compound, a hydroxypyridinone compound, a hydroxyphenylbenzimidazole compound , A hydroxyindoline-based compound, a hydroxybenzotriazine-based compound, and an oxime.
15. The method of claim 14,
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,
A phosphonium compound and a skin whitening ingredient are formulated into a single preparation in an encapsulated form; A two - formulated cosmetic composition for whitening skin wherein a phosphonium compound and a skin whitening component are separated from each other.

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