KR102453486B1 - 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 a protein residue on the skin surface, thereby forming a covalent bond without damaging the skin, thereby providing a semi-permanent desired whitening effect.

Description

Cosmetic compositions for skin whitening}

The present invention relates to a reactive skin whitening component and a cosmetic composition for skin whitening to which a protein-binding functional group is bound.

The whitening function of cosmetics refers to the fact that the effective ingredient makes the skin color of its own by continuously using it to brighten the skin color or tone of a person, or to cover and beautify skin defects such as blemishes and blemishes. It prevents the formation of melanin by blocking the expression of tyrosinase or induces a mechanism that interferes with the delivery of melanin, but in order to obtain the whitening effect, it should be used continuously during the turnover period (28 days, the period when the keratin of the skin is regenerated) to see the effect. The downside is that it can. In addition, as a method of applying cosmetics to the skin, there is a disadvantage in that it is difficult to obtain actual efficacy because ingredients that do not have affinity for skin or hair are easily removed during washing or daily life. On the one hand, to obtain an immediate effect, white cosmetics or color cosmetics are used externally to temporarily brighten the skin tone, but this method also has the disadvantage of being easily removed during cleaning and daily life.

In order to improve this shortcoming, cosmetic ingredients are left on the skin using various mechanisms, such as lipids, ceramides, surfactants, skin-friendly minerals, and techniques to increase skin permeability, which have affinity with the skin and hair and other surfaces. Although there is a method of invasiveness, there is a limitation that the amount that actually remains on the skin is only a small amount and the effect is also temporarily maintained. Therefore, recently, a method of chemically modifying the skin and hair surfaces of a cosmetic material using a bioconjugation method has been introduced. If a cosmetic effect is given by modifying the stratum corneum in this way, the cosmetic effect can be maintained semi-permanently until desquamation occurs, and if necessary, it has the advantage that it can be easily removed through peeling.

Recently, L'Oreal has proposed a method for rapidly obtaining the artificial tanning effect of dihydroxyacetone (DHA) by modifying the skin with an amine group-introduced alkoxysilane (Patent Document 1). It is classified into these three grades and has a disadvantage that it is difficult to be applied to practical products. Although the previous studies of Patent Document 2 and Patent Document 3 also suggest a method for skin modification, the technology for applying the bioconjugation method to cosmetics is still in its infancy to the extent that there are not many examples.

The present inventors have devised a method for modifying an amine group, a carboxyl group, a thiol group, a hydroxyl group, etc. in skin proteins through prior research. In particular, a method for directly modifying proteins present in hair and skin using PCI (polymeric carbodiimide) (Patent Document 4) has been discovered and research is being conducted to apply it to personal care. Since the carbodiimide reaction can be toxic to the human body due to the formation of acylurea, it was possible to minimize the carbodiimide reaction by using a carbodiimide in the form of a polymer. However, since there are not a variety of reaction promoters such as PCI that can apply the reaction to the skin, a reaction mediator that is safe for the human body and can remain on the skin for a long time is needed to apply the bioconjugation method universally. do.

US Patent Publication No. 2010-516546 US Patent Publication No. 2011-0274639 US Patent Publication No. 2006-0233729 Korean Patent Publication No. 2008-0064467

An object of the present invention is to provide a cosmetic composition for skin whitening that can continuously impart a semi-permanent whitening effect without damaging the skin.

As a means for solving the above problems, the present invention is a dihydroquinoline-based compound; And it provides a cosmetic composition for skin whitening comprising a skin whitening component.

As another means for solving the above problems, the present invention provides a cosmetic composition for skin whitening further comprising a peptide bond formation 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 dihydroquinoline-based compound that introduces a specific functional group capable of covalent bonding with a protein residue of the skin, thereby forming a covalent bond without damaging the skin, making it semi-permanent provides a skin whitening effect. In addition, it provides an effective whitening effect by including a peptide bond formation promoting additive.

1 is a clinical test result quantifying the skin brightness improvement rate due to 2 weeks of use of a cream-formed mask pack containing glucosamine and a dihydroquinoline-based compound (n=7, *p < 0.05).
2 is a clinical trial result in which the skin brightness improvement rate due to the use of a cream-formed mask pack containing glucosamine and a dihydroquinoline-based compound for one week was quantified through a questionnaire (n=20).
3 is a clinical test result quantifying the improvement rate of yellowness of the skin due to 2 weeks of use of a cream-formed mask pack containing chitosan and a dihydroquinoline-based compound (n=7, *p < 0.05).
4 is a clinical test result quantifying the skin gloss improvement rate due to 2 weeks of use of a cream-formed mask pack containing chitosan and a dihydroquinoline-based compound (n=7, *p < 0.05).

The present invention relates to a cosmetic composition for skin whitening comprising a dihydroquinoline-based compound and a skin whitening component.

The cosmetic composition for skin whitening according to the present invention, for example, reacts a dihydroquinoline-based compound with a known skin whitening component to form a covalent bond with a protein of the skin through a reactive whitening component to which hydroquinoline is bonded. The whitening effect can be maximized.

The dihydroquinoline-based 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 cosmetic composition. If its content is less than 0.001 parts by weight, there is a problem that a continuous skin whitening effect is difficult to appear. There is a problem in that it does not help to improve durability by reacting with a substance and may act as a lost component.

In the present invention, the 'skin whitening effect' refers to a function of brightening the color or tone of the skin, improving the skin's luster to make the skin clear, or covering skin defects such as blemishes and blemishes existing on the skin to beautify it. it means. In addition, a function to control the tone by preventing the skin surface from turning yellow by preventing aging or oxidation is also included.

The skin whitening component used in the present invention may include a whitening component that can improve the damaged area due to melanin pigmentation of the skin, such as extracts derived from natural products such as animals, plants and minerals, amino acids, hormones, vitamins, etc. , but not limited thereto. For example, the component may be a hydroquinone-based compound; vitamins and derivatives thereof, such as niacinamide and vitamin C; flavonoid compounds such as Moistin and Hesperidin; resveratrol compounds and derivatives thereof; curcubitacin derivatives; amino acid-based compounds such as glutathione and methyl undecenoyl leucinate; Arbutin, kojic acid, azelaic acid, alpha hydroxy acid, alpha-bisabolol, adenosine, ascorbyl glucoside, ascorbyl tetraisopalmitate, ethyl ascorbyl ether, fullerene, acetyl tyrosine, diacetyl benzoyl tyrol, baekchul oil, Magnesium ascorbyl phosphate, diosmethin, mayslignan, acetylsphingosine, dihydroxymethoxychalcone, alpha-bisabolol, protocatechuic aldehyde, oryzanol, licorice extract, mulberry extract, green tea extract, epiphyllum extract, Yeast extract, baekchul extract, wheat germ extract, peony extract, rhizome extract, ginseng extract, red ginseng extract, ginseng extract, agrimony extract, indocanna root extract, Jeju reed extract, old ginseng extract, yiin extract, western plum extract, chitosan , may be one or more selected from the group consisting of polylysine, glucosamine and derivatives thereof, but is not limited thereto.

The skin lightening component 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. If the content thereof is less than 0.001, the effect is insignificant and there is a limit, and if it exceeds 50 parts by weight, there is a problem in formulation and stabilization.

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

In addition, the skin whitening component in the present invention may have a functional group capable of covalent bonding with a protein residue on the skin surface.

The functional group covalently bound to the protein is carbodiimide, imidoester, arylazide, diazirine, hydroxymethyl phosphine, pentafluorophenyl ester, pyridyl disulfide, sulfo-hydroxysuccinimide ester, alkoxy amine, hydrazide, haloacetyl, azide, carbonate, aldehyde, propionaldehyde, butylaldehyde, nitrophenyl carbonate, aziridine, isocyanate, thiocyanate, epoxide, tresylate, succinimide, hydroxysuccinimidyl ester , imidazole, oxycarbonyl imidazole, imine, thiol, maleimide, vinylsulfone, ethylenimine, thioether, acrylonitrile, acrylic acid or methacrylic acid ester, disulfide, ketone, carboxylic acid and phosphate selected from the group consisting of There may be more than one, but this is not limited now.

In addition, the protein may include a reactive moiety of thiol, hydroxyl, carboxyl or amine.

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

[Formula 1]

In Formula 1,

R ₁ represents a water-soluble nonionic polymer, a polymer resin in the form of beads or resins, or silica beads,

R ₂ and R ₃ are the same or different, respectively, and represent any one selected from the group consisting of straight-chain or branched saturated or unsaturated alkyl having 1 to 10 carbons, and straight-chain or branched saturated or unsaturated alkoxy having 1 to 10 carbons.

Preferably, the water-soluble nonionic polymer has a weight average molecular weight of 1,000 Da or more and less than 300,000 Da.

The water-soluble nonionic polymer is specifically polyethylene glycol, polyvinyl alcohol, polyethylene oxide, polyacrylonitrile, polyvinylpyrrolidone, polyisopropylacrylamide, cellulose derivatives, starch derivatives, dextran and guar gum. It may be one or more polymers selected from the group consisting of.

It is preferable that the polymer weight average molecular weight of the bead form or resin form is 1,000 Da or more and less than 300,000 Da.

The polymer resin in the form of beads or resin is specifically styrene, ethylene, butadiene, acrylonitrile, methylstyrene, terephthalate, ethylene chloride, etherketone, etherimide, ethersulfone, phthalamide, phenylene ether, phenylene oxide. , phenylene sulfide, sulfone, urethane, vinylidene fluoride and may be a copolymer polymerized with a monomer selected from the group consisting of tetrafluoroethylene.

The polymer beads 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 may be included. If the diameter of the polymer beads is less than 100 nm, it may cause safety problems on the skin surface, and if the diameter of the polymer beads is larger than 1 mm, there are problems in formulation and stabilization.

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

As a preferred embodiment of the cosmetic composition for skin whitening according to the present invention, a whitening component having a carboxyl group is made in the form of a reactive ester whitening component having direct bioreactivity, or an amino acid present in excess in skin keratin (15.5 to 23.5%) ( ex, aspartic acid, glutamic acid) can be reactively esterified to create a targetable form for skin whitening ingredients containing amine groups, thereby increasing the reaction efficiency and significantly enhancing the effect. As a more preferred embodiment, a reactive ester is formed by first reacting a polymeric dihydroquinoline-based compound of Formula 1 on the surface of a skin whitening component molecule or skin protein having a carboxyl group, and then adding an amine to the formed reactive ester functional group in the molecule An excellent whitening effect can be obtained by reacting the whitening component having the present or by reacting it with an amine on the skin surface.

In Reaction Scheme 1 below, the skin lightening component molecule having a carboxyl group reacts primarily with a dihydroquinoline-based compound to form a reactive ester, followed by reaction with an amino acid of a living body having an amine residue to form a covalent bond.

[Scheme 1]

As shown in Scheme 2 below, aspartic acid and glutamic acid, which are biological amino acids having a carboxyl group on the protein surface of the skin, first react with a dihydroquinoline-based compound to form a reactive ester, and then react with a whitening component having an amine residue to form a covalent bond. A reaction schematic diagram is shown.

In Reaction Scheme 2 below, aspartic acid and glutamic acid, which are biological amino acids having a carboxyl group on the protein surface of the skin, first react with a dihydroquinoline-based compound to form a reactive ester, followed by a reaction with a whitening component having an amine residue to form a covalent bond A schematic diagram is shown.

[Scheme 2]

Using a dihydroquinoline-based compound, the skin whitening component attached to the skin protein and peptide bond is not removed from the skin by washing methods such as soap and cleanser, and can remain attached to the skin semi-permanently.

By increasing the reaction efficiency of skin proteins and whitening ingredients by dihydroquinoline compounds, the reactive whitening ingredients bound to the skin do not come off easily during general washing with soap, etc., and can remain attached to the skin almost permanently. have.

The present invention also provides skin lightening ingredients such as carbodiimide, imidoester, arylazide, diazirine, hydroxymethyl phosphine, pentafluorophenyl ester, pyridyl disulfide, sulfo-hydroxysuccinimide ester, alkoxy amine , hydrazide, haloacetyl, azide, carbonate, aldehyde, propionaldehyde, butyraldehyde, nitrophenyl carbonate, aziridine, isocyanate, thiocyanate, epoxide, tresylate, succinimide, hydroxysuccinimidyl from the group consisting of esters, imidazoles, oxycarbonyl imidazoles, imines, thiols, maleimides, vinylsulfones, ethylenimines, thioethers, acrylonitrile, acrylic or methacrylic acid esters, disulfides, ketones, carboxylic acids and phosphates It may include a reactive whitening component to which a functional group covalently binding to one or more selected proteins is bound.

For example, as in Scheme 1, a whitening component to which a dihydroquinoline-based compound produced by a primary reaction of a dihydroquinoline-based compound is combined may be included. In addition, the present invention may include a cosmetic composition for skin whitening comprising the reactive whitening component.

In the cosmetic composition for skin whitening according to the present invention, hydroxysuccinimide, hydroxycarboxyimide, hydroxytriazole, hydroxybenzotriazole, hydroxypyridinone, hydroxyphenylbenzimidazole, hydroxyindolinone , hydroxybenzotriazine and one or more peptide bond formation reaction promoting additives selected from the group consisting of oxima. 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 it is 0.001 - 1 weight part, More preferably, it is 0.001 - 0.1 weight part. Even if 10 parts by weight or more is used, the speed of the chemical reaction is saturated, so there is no economic feasibility of the product, and it does not help the stability of the product. When used below 0.0001, there is little or no benefit to reactivity.

In addition, in order to increase the effect incidentally in the cosmetic composition for skin whitening according to the present invention, fatty acids such as palmitic acid and stearic acid, fatty alcohols, straight-chain and branched long-chain alkyl quaternary ammonium salts Formulation can be facilitated when mixed with cationized surfactants such as cationized surfactants, cationized cellulose, cationized guar, cationized polymer such as cationized polyvinylpyrrolidone, and silicone. In addition, for formulation into cosmetic formulations, solvents, surfactants, thickeners, stabilizers, preservatives, colorants, pH adjusters, metal ion sequestrants, pearlizers, appearance improvers, emollients, pigments, powder particles, etc. for cosmetic formulation Ingredients may be incidentally included. Components 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 cosmetic composition for skin whitening according to the present invention includes a component having a whitening function having a functional group and may be used in the formulation of the cosmetic composition for whitening. Examples of application of hair products include pre-shampoo compositions, shampoos, rinses, treatments, waxes, gels, sprays, mousses, hair lotions, hair packs, hair essences, hair creams, research hair dyes, temporary hair dyes, perms, Non-woven fabrics, sheets, etc. can all be included, and examples of application of skin products include basic cosmetics (lotions, serums, essences, lotions, creams, etc.) for preparing and protecting the skin in general, color cosmetics (make-up base, foundation, powder, Eye shadow, lip gloss, lipstick, lip balm, etc.), makeup for nails and nails (manicure, nutrition, enhancer, top coat, etc.), cleansing cosmetics (foam cleansing, cleansing oil, cleansing lotion, cleansing cream, cleansing gel, pack, Mask, soap, cleansing tissue, etc.), sun care cosmetics, and body cosmetics (body lotion, shower gel, body cream, body oil, etc.) may all be included.

More preferably, the cosmetic composition for skin whitening according to the present invention includes a whitening component having a reactive functional group while including a dihydroquinoline-based compound. It is easier to maintain the activity, and the reaction can be caused by mixing with a buffer to adjust the pH immediately before use, or by contacting with water during the washing process. Examples of the non-aqueous formulation include liquid type, sheet type, powder powder type, tablet type, oil, wax, ampoule, gel, and the like, which are used as conventional non-aqueous cosmetic formulations. In addition, the dihydroquinoline-based compound and the whitening component may be formulated as a single agent in an encapsulated form or as two agents in a separate form. Also, a method of blocking a derivative in which a reactive functional group and a component having a whitening function are combined from moisture through encapsulation may also be used.

In order to enhance the whitening effect having a functional group in the cosmetic composition for skin whitening according to the present invention, a 2-basic acid ester oil such as dioctyl succinate, dioctyl adipate, diethyl sebacate, etc., polyol, polyethylene glycol, propylene glycol, Hexylene glycol, butanediol and their isomers, glycerol, benzyl alcohol, ethoxydiglycol and derivatives thereof can be used. The above-mentioned solvents increase the permeability of hair or skin and are used as solvents for poorly soluble substances. More preferably, the solvent used to enhance the activity-maintaining effect of the 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 only illustrative of the present invention, and the content of the present invention is not limited to the following examples.

Example 1 ~2 and comparative example 1: Cream ( 100 g ) Formulation of mask pack manufacturing

A cream-formed mask pack was prepared with the composition and content of Table 1 below. After heating the aqueous phase raw materials 3 to 13 to 70 ℃, using a homomixer, the mixture was uniformly mixed at 1500 rpm for 5 minutes. The oily components 15 to 24 dissolved by heating to 70° C. in advance were added to the mixed aqueous phase and uniformly mixed at 3500 rpm for 5 minutes using a homomixer. After lowering the temperature to 50℃, neutralizing agent, dihydroxyquinoline compound Polystyrene supported 1-isobutoxycarbonyl-2-isobutoxy-1,2-dihydroquinoline (PS-IIDQ)] 1 and peptide bond formation promoting additive 2 NHS (N-hydroxysuccinimide) ), and fragrance 14, followed by uniform mixing for 3 minutes with a homomixer, followed by defoaming, filtration and cooling.

The PS-IIDQ is a polymer in which R ₁ in Chemical Formula 1 is represented by the following Chemical Formula 2 (m + n: l = 99: 1 mole ratio), and a weight average molecular weight of 200,000 Da; R ₂ is isobutyl; R ₃ is Isobutoxy:

[Formula 2]

No ingredient Example 1 Example 2 Comparative Example 1 One PS-IIDQ 0.1 0.1 - 2 NHS 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 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 fare 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

After attaching glucosamine to the skin by bioconjugation using PS-IIDQ, the efficacy was confirmed.

The mask pack formulations of Comparative Example 1 and Example 1 were prepared, respectively, and the skin brightness change was confirmed by applying it to 7 subjects. The mask pack was used twice a day for 2 weeks by washing the face with a cleanser before use, attaching the mask pack for 30 minutes and washing again. Skin brightness was checked with a LAB measuring device (Konica Minolta CR-300 Chroma Meter).

As a result of the experiment, it was confirmed that when glucosamine was attached using PS-IIDQ (Example 1), the brightness of the skin was improved by 1.22% for 2 weeks [Fig. 1]. Compared to Comparative Example 1, Example 1 had a significantly improved whitening effect.

It is expected that various whitening ingredients, as well as glucosamine, can be attached to the skin by bioconjugation and remain for a long time, so that the whitening effect can be continuously obtained for a certain period of time.

Experimental example 2

After attaching glucosamine to the skin by bioconjugation using PS-IIDQ, the efficacy was confirmed.

The mask pack formulations of Comparative Example 1 and Example 1 were prepared, respectively, and the skin brightness change was confirmed by applying to 20 subjects. The mask pack was used once a day for a week by washing the face with a cleanser before use, attaching the mask pack for 30 minutes, and then washing again.

Changes in skin brightness were evaluated through a user questionnaire. By setting items such as moisturizing, whitening, and elasticity, X was set when it was similar to usual, and O was set when it felt better.

As a result of the experiment, it was confirmed that when glucosamine was attached to the skin using the bioconjugation method using PS-IIDQ, the brightness of the skin felt by the user was improved by 80% or more for 1 week [Fig. 2]. Compared to Comparative Example 1, Example 1 had a significantly improved whitening effect.

It is expected that various whitening ingredients as well as glucosamine can be attached to the skin by bioconjugation and remain for a long time, so that the whitening effect can be continuously obtained 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

After chitosan was attached to the skin using bioconjugation of PS-IIDQ, the efficacy was confirmed. (The skin whitening effect was confirmed by controlling the tone by reducing yellowing by preventing aging or oxidation of the skin surface)

The mask pack formulations of Comparative Examples 2 and 3 were prepared, respectively, and applied to the cheeks of 7 subjects to confirm skin yellowness and gloss change, which are measures of skin aging. The mask pack was used twice a day for 2 weeks by washing the face with a cleanser before use, attaching the mask pack for 30 minutes and washing again. Yellowness was checked with a LAB measuring device (Konica Minolta CR-300 Chroma Meter), and gloss change was checked with a gloss meter (C&K MPA 580, skin glossymeter GL200).

As a result of the experiment, when chitosan was attached using the bioconjugation method of PS-IIDQ (Example 3), it was confirmed that the skin yellowness was improved by 4.97% after 2 weeks of use by the antioxidant and anti-aging ability of chitosan, and the skin It was also confirmed that there was an improvement effect of 5.62% after 2 weeks of use [Figs. 3 and 4]. Compared to Comparative Example 2, Example 3 had a significantly improved whitening effect.

It is expected that not only chitosan but also various effective substances can be attached to the skin by bioconjugation and remain for a long time, so that the cosmetic effect can be continuously obtained for a certain period of time.

Example 4-5 and comparative example 3-4: Manufacture of non-woven mask pack

A mask pack formulation in the form of a non-woven fabric was prepared with the composition and content of Table 2 below.

More specifically, the aqueous phase raw materials 1, 8, 9, 10, 11, 14, 15, and 16 were heated to 70 °C and then uniformly mixed at 1500 rpm for 5 minutes using a homo mixer. Oil phase components 5, 6, 7, 12, 13 dissolved by heating to 70 in advance were added to the mixed aqueous phase and uniformly mixed for 5 minutes at 2000 rpm using a homomixer. Thereafter, the temperature was lowered to 50 °C, and polymer supported IIDQ (PS-IIDQ) 2, NHS 3, glucosamine 4, and fragrance 17 were post-added and uniformly mixed for 3 minutes with a homomixer, followed by defoaming, filtration, and cooling. The formulation was then impregnated into the nonwoven mask.

No Raw material (wt%) 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-IIDQ - 0.1 - 0.1 3 NHS - - 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 2.0 2.0 2.0 2.0 16 Hydroxyethylcellulose 0.4 0.4 0.4 0.4 17 fare 0.1 0.1 0.1 0.1

Experimental example 4: Evaluation of skin brightness improvement

After attaching glucosamine to the skin using bioconjugation of PS-IIDQ, the efficacy was confirmed. The mask pack formulations of Comparative Examples 3 to 4 and Examples 4 to 5 were prepared, and the skin brightness change was confirmed by applying it to 7 subjects.

The mask pack was used once a day for 2 weeks by washing the face with a cleanser before use, attaching the mask pack for 30 minutes and washing again. Skin brightness was checked with LAB measuring equipment (Konica Minolta CR-300 Chroma Meter).

Then, the difference in skin color (ΔL*) at the measurement time point and the application start time after application of each test substance was calculated according to Equation 1 below, and the results are shown in Table 3 below.

On the other hand, the whitening effect is determined by comparing the ΔL* between the sample application site and the control site. When the ΔL* value is about 2, the whitening of the deposited pigment is clear, and when it is about 1.5 or more, it can be determined that there is a whitening effect. .

[Equation 1]

ΔL = L value at the time of measurement after application - L value at the beginning of application

division Glucosamine (2%) Comparative Example 3 Example 4 Comparative Example 4 Example 5 2 days 0.6 0.8 0.7 1.2 7 days 0.8 1.3 0.8 1.7 14 days 0.9 1.7 0.5 2.5

As shown in Table 3, the whitening effect of glucosamine by the bioconjugation of PS-IIDQ was confirmed that the improvement of skin brightness was significantly improved for 2 weeks when PS-IIDQ and NHS were used.

It is expected that various whitening substances as well as glucosamine can be attached to the skin by bioconjugation and remain for a long time, so that the cosmetic effect can be continuously obtained for a certain period of time.

Claims (17)

A dihydroxyquinoline-based compound represented by Formula 1 and a skin whitening component,
The skin whitening component has a functional group capable of covalent bonding with a protein residue on the skin surface,
The skin lightening component is 0.001 to 50 parts by weight based on 100 parts by weight of the total composition.
Cosmetic composition for skin whitening:
[Formula 1]

In Formula 1,
R1 represents a water-soluble nonionic polymer, a polymer resin in the form of beads or resins, or silica beads,
R ₂ and R ₃ are the same or different, respectively, and represent any one selected from the group consisting of straight-chain or branched saturated or unsaturated alkyl having 1 to 10 carbons, and straight-chain or branched saturated or unsaturated alkoxy having 1 to 10 carbons.
delete The method of claim 1,
The water-soluble nonionic polymer has a weight average molecular weight of 1,000 Da or more and less than 300,000 Da of a cosmetic composition for skin whitening.
The method of claim 1,
The water-soluble nonionic polymer is made of polyethylene glycol, polyvinyl alcohol, polyethylene oxide, polyacrylonitrile, polyvinylpyrrolidone, polyisopropylacrylamide, cellulose derivatives, starch derivatives, dextran and guar gum. A cosmetic composition for skin whitening which is one or more polymers selected from the group.
The method of claim 1,
The bead type or resin type polymer resin has a weight average molecular weight of 1,000 Da or more and less than 300,000 Da of a cosmetic composition for skin whitening.
The method of claim 1,
The polymer resin in the form of beads or resin is styrene, ethylene, butadiene, acrylonitrile, methylstyrene, terephthalate, ethylene chloride, etherketone, etherimide, ethersulfone, phthalamide, phenylene ether, phenylene oxide, phenyl A cosmetic composition for skin whitening, which is a polymer polymerized with a monomer selected from the group consisting of lensulfide, sulfone, urethane, vinylidene fluoride and tetrafluoroethylene.
The method of claim 1,
The silica beads have an average particle diameter of 100 nm to 1 mm in a cosmetic composition for skin whitening.
The method of claim 1,
The dihydroxyquinoline-based compound is 0.001 to 10 parts by weight based on 100 parts by weight of the total composition for skin whitening cosmetic composition.
The method of claim 1,
The skin whitening component is a cosmetic composition for skin whitening comprising a carboxyl group or an amine group in a molecule.
The method of claim 1,
The skin lightening component includes vitamins and derivatives thereof; flavonoid compounds; resveratrol compounds and derivatives thereof; curcubitacin derivatives; amino acid-based compounds; Arbutin, kojic acid, azelaic acid, alpha hydroxy acid, alpha-bisabolol, adenosine, ascorbyl glucoside, ascorbyl tetraisopalmitate, ethyl ascorbyl ether, fullerine, acetyl tyrosine, diacetyl benzoyl tyrol, baekchul oil, Magnesium ascorbyl phosphate, diosmethin, mayslignan, acetylsphingosine, dihydroxymethoxychalcone, alpha-bisabolol, protocatechuic aldehyde, oryzanol, licorice extract, mulberry extract, green tea extract, sagebrush extract, Yeast extract, baekchul extract, wheat germ extract, peony extract, rhizome extract, ginseng extract, red ginseng extract, ginseng extract, agrimony extract, indocanna root extract, Jeju reed extract, old ginseng extract, yiin extract, prune extract, chitosan , polylysine, glucosamine, and a cosmetic composition for skin whitening at least one selected from the group consisting of derivatives thereof.
delete The method of claim 1,
The functional group covalently bound to the protein is carbodiimide, imidoester, arylazide, diazirine, hydroxymethyl phosphine, pentafluorophenyl ester, pyridyl disulfide, sulfo-hydroxysuccinimide ester, alkoxy amine, hydrazide, haloacetyl, azide, carbonate, aldehyde, propionaldehyde, butylaldehyde, nitrophenyl carbonate, aziridine, isocyanate, thiocyanate, epoxide, tresylate, succinimide, hydroxysuccinimidyl ester , imidazole, oxycarbonyl imidazole, imine, thiol, maleimide, vinylsulfone, ethylenimine, thioether, acrylonitrile, acrylic acid or methacrylic acid ester, disulfide, ketone, carboxylic acid and phosphate selected from the group consisting of At least one cosmetic composition for skin whitening.
delete The method of claim 1,
The composition is a cosmetic composition for skin whitening further comprising a peptide bond formation reaction promoting additive.
15. The method of claim 14,
The peptide bond-forming reaction promoting additive is hydroxysuccinimide, hydroxycarboxyimide, hydroxytriazole, hydroxybenzotriazole, hydroxypyridinone, hydroxyphenylbenzimidazole, hydroxyindolinone, hydroxy A cosmetic composition for skin whitening at least one selected from the group consisting of benzotriazine and oxima.
15. The method of claim 14,
The peptide bond formation reaction promoting additive is 0.0001 to 10 parts by weight based on 100 parts by weight of the total composition for skin whitening cosmetic composition.
The method of claim 1,
The dihydroxyquinoline-based compound and the skin lightening component are formulated as a single agent in an encapsulated form; A cosmetic composition for skin whitening formulated in two separate forms in which a dihydroxyquinoline-based compound and a skin lightening component are each separated.

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