KR102486936B1 - 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 covalently bonding with a protein residue on the skin surface, thereby providing a desired whitening effect semi-permanently by forming a covalent bond without damaging the skin.

Description

Cosmetic compositions for skin whitening {Cosmetics compositions for skin whitening}

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

The whitening function of cosmetics refers to the brightening of a person's skin color or tone, or to cover and beautify skin defects such as melasma, blemishes, etc., by continuously using effective ingredients to make the skin color of one's own. By blocking the expression of tyrosinase, it induces a mechanism that prevents the formation of melanin or interferes with the transmission of melanin. There are downsides to being able to. In addition, in the method of applying cosmetics to the skin, 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, in order to obtain an immediate effect, white cosmetics or color cosmetics are used externally to brighten the skin tone temporarily, but this method also has the disadvantage of being easily removed during washing and daily life.

In order to improve this shortcoming, various mechanisms such as lipids, ceramides, surfactants, skin-friendly minerals, and skin permeability enhancement technologies that are compatible with surfaces including skin and hair are used to leave cosmetic ingredients on the skin. Although there is an invasive method, there is a limit in that only a small amount actually remains on the skin 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 begun to be introduced. If a cosmetic effect is imparted by modifying the stratum corneum by this method, there is an advantage in that the cosmetic effect can be maintained semi-permanently until desquamation occurs, and can be easily removed through peeling if necessary.

Recently, L'Oreal has proposed a method to quickly obtain the artificial tanning effect of dihydroxyacetone (DHA) by modifying the skin with an alkoxysilane into which an amine group is introduced (Patent Document 1), but alkoxysilane has good reactivity, so MSDS toxicity There is a disadvantage that it is difficult to apply to practical products because it is classified into these 3 grades. Prior research in Patent Document 2 and Patent Document 3 also suggests a method for modifying the skin, but the technology of applying the bioconjugation method to cosmetics is still in its infancy so 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, and the like in skin proteins through previous studies. In particular, a method of directly modifying proteins present in hair and skin using PCI (polymeric carbodiimide) is being discovered (Patent Document 4) and research is being conducted to apply it to personal care. The carbodiimide reaction can be toxic to the human body through the formation of acylurea, so it can be minimized by using a polymeric carbodiimide. However, since there are not many reaction accelerators such as PCI that can apply the reaction to the skin, a reaction mediator that is safe for the human body and can remain effective 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 phosphonium-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 to 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 that introduces a specific functional group capable of covalent bonding with protein residues in the skin, thereby forming a covalent bond without damaging the skin to provide a semi-permanent Provides 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 improvement rate of skin brightness due to the use of a mask pack of a cream formulation containing glucosamine and a phosphonium-based compound for 2 weeks (n = 7, *p < 0.05).
Figure 2 is a clinical test result quantifying the improvement rate of skin brightness due to the use of a mask pack of a cream formulation containing glucosamine and a phosphonium-based compound for one week through a questionnaire (n = 20).
Figure 3 is a clinical test result quantifying the improvement rate of skin yellowness due to the use of a mask pack of a cream formulation containing chitosan and a phosphonium-based compound for 2 weeks (n = 7, *p < 0.05).
Figure 4 is a clinical test result quantifying the improvement rate of skin gloss due to the use of a mask pack of a cream formulation containing chitosan and a phosphonium-based compound for 2 weeks (n = 7, *p < 0.05).

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

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

The phosphonium-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 the content is less than 0.001 parts by weight, there is a problem in that it is difficult to show a continuous skin whitening effect, and if it exceeds 10 parts by weight, the active substance in a state where the phosphonium-based compound present in excess beyond the reactive site in the skin does not react with the skin. By reacting with it, there is a problem that it does not help to improve durability and can act as a component that is lost.

In the present invention, the term 'skin whitening effect' refers to a function of brightening the color or tone of the skin, improving the gloss of the skin, making the skin clear, or covering and beautifying skin defects such as spots and blemishes existing on the skin. it means. In addition, it also includes a function of adjusting the tone by preventing aging or oxidation of the skin surface to prevent it from turning yellow.

The skin whitening component used in the present invention may include a whitening component that can improve areas damaged by 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 their derivatives, such as niacinamide, vitamin C, and the like; flavonoid-based compounds such as Moistin and Hesperidin; resveratrol compounds and their derivatives; curcubitacin derivatives; amino acid compounds such as glutathione, methylundecenoyleucinate and the like; Arbutin, kojic acid, azelaic acid, alpha hydroxy acid, alpha-bisabolol, adenosine, ascorbyl glucoside, ascorbyl tetraisopalmitate, ethyl ascorbyl ether, fullerene, acetyl tyrosine, diacetylbenzoylattyrol, white extract oil, Magnesium Ascorbyl Phosphate, Diosmetin, Mayslignan, Acetylsphingosine, Dihydroxymethoxychalcone, Alpha-Bisabolol, Protocatechuic Aldehyde, Oryzanol, Licorice Extract, Paper Mulberry Extract, Green Tea Extract, Mortar Extract, Adlay Extract, Yeast Extract, Baekchul Extract, Wheat Germ Extract, Peony Extract, Root Extract, Ginseng Extract, Red Ginseng Extract, Sambaekcho Extract, Agrimony Extract, Indian Canna Root Extract, Jeju Sasa Extract, Gosam Extract, Uiyiin Extract, Western Plum Extract, Chitosan , polylysine, may be one or more selected from the group consisting of glucosamine and derivatives thereof, but is not limited thereto.

The skin whitening 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 is less than 0.001, the effect is insignificant and there is a limit, and if it exceeds 50 parts by weight, there are problems in formulation and stabilization.

In particular, the skin whitening component in the present invention can increase the reaction efficiency with the phosphonium-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 covalently bonding with a protein residue on the skin surface.

Functional groups covalently bonded to the protein include carbodiimide, imidoester, arylazide, diazirine, hydroxymethyl phosphine, pentafluorophenyl ester, pyridyl disulfide, sulfo-hydroxysuccinimide ester, alkoxy amine, Hydrazides, haloacetyls, azides, carbonates, aldehydes, propionaldehydes, butyraldehydes, nitrophenyl carbonates, aziridines, isocyanates, thiocyanates, epoxides, tresylates, succinimides, hydroxysuccinimidyl esters , imidazoles, oxycarbonyl imidazoles, imines, thiols, maleimides, vinylsulfones, ethylenimines, thioethers, acrylonitriles, acrylic acid or methacrylic acid esters, disulfides, ketones, carboxylic acids, and phosphates. There can be more than one, but is no longer limited.

In addition, the protein may include a reactive residue such as thiol, hydroxyl, carboxyl, or amine.

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

[Formula 1]

In Formula 1,

R1 represents a water-soluble nonionic polymer, a polymer resin in the form of beads or resin, or silica beads,

R ₂ is benzotriazole-yloxy, azabenzotriazole-yloxy, nitrobenzotriazole-yloxy, pentafluorophenyl-O- (pentafluoroopenyl) It may be one selected from the group consisting of -O-), pyridylthio, hydrooxobenzotriazin, cyanoethoxycarbonylmethylidene, and halogen,

R ₃ to R ₅ are the same as or different from each other, and are dialkylamino-based compounds or heterocycloamine-based compounds.

The dialkylamino-based compound may be a compound having 1 to 10 carbon atoms, and preferably has 3 or less carbon atoms. The heterocycloamine compound may be a compound having 2 to 10 carbon atoms, and preferably has 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, and when the molecular weight is 300,000 Da or more, the ratio of the phosphonium-based compound inducing covalent bonds is too small to exhibit efficacy.

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

It is preferable that the weight average molecular weight of the polymer in the form of beads or resin is 1,000 Da or more and less than 300,000 Da, and when the molecular weight is 300,000 Da or more, the ratio of the phosphonium-based compound inducing covalent bonds is too small to exhibit efficacy.

The bead-type or resin-type polymer resin is specifically styrene, ethylene, butadiene, acrylonitrile, methyl styrene, terephthalate, ethylene chloride, ether ketone, ether imide, ether sulfone, phthalamide, phenylene ether, phenylene oxide , It may be a copolymer polymerized with a monomer selected from the group consisting of phenylene sulfide, sulfone, urethane, vinylidene fluoride and 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, and most preferably 1 μm to 70 μm. can be included If the diameter of the polymer bead is less than 100 nm, it may cause safety problems on the skin surface, and if the diameter of the polymer bead is greater than 1 mm, there is a problem 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. can be included When the diameter of the silica bead is smaller than 100 nm, it may cause safety problems on the skin surface, and when the diameter of the silica bead 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, the whitening component having a carboxyl group is directly made in the form of a reactive ester whitening component having bioreactivity, or an amino acid present in excess in skin keratin (15.5 to 23.5%) ex, aspartic acid, glutamic acid) by reactive esterification to create a form that can be targeted by skin whitening ingredients containing an amine group, thereby increasing reaction efficiency, thereby significantly increasing the effect. As a more preferred embodiment, a reactive ester is formed by a primary reaction of the polymeric phosphonium-based compound of Formula 1 on the skin whitening component molecule having a carboxyl group or on the surface of a skin protein, and the formed reactive ester functional group has an amine in the molecule again. An excellent whitening effect can be obtained by reacting a whitening component or reacting with an amine on the skin surface.

In Reaction Scheme 1 below, a reaction schematic diagram in which a skin whitening ingredient molecule having a carboxyl group reacts first with a phosphonium-based compound to form a reactive ester and subsequently reacts with an amino acid in a living body having an amine residue to form a covalent bond is shown.

[Scheme 1]

As shown in Scheme 2 below, aspartic acid and glutamic acid, biogenic amino acids having carboxyl groups on the surface of skin proteins, react with phosphonium-based compounds to form reactive esters, followed by reaction with whitening ingredients having amine residues to form covalent bonds. A schematic diagram was shown.

In the following Reaction Scheme 2, aspartic acid and glutamic acid, biogenic amino acids having carboxyl groups on the surface of skin proteins, react first with phosphonium-based compounds to form reactive esters, and subsequently react with whitening ingredients having amine residues to form covalent bonds. showed

[Scheme 2]

Skin whitening ingredients attached to skin proteins and peptide bonds using phosphonium-based compounds can remain attached to the skin semi-permanently without being removed from the skin by washing methods such as soaps and cleansers.

By increasing the reaction efficiency of skin proteins and whitening ingredients by phosphonium-based 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. .

The present invention also relates to skin whitening 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 in the group consisting of esters, imidazoles, oxycarbonyl imidazoles, imines, thiols, maleimides, vinylsulfones, ethylenimines, thioethers, acrylonitriles, acrylic or methacrylic acid esters, disulfides, ketones, carboxylic acids and phosphates It may include a reactive whitening component to which a functional group covalently bonded to one or more selected proteins is bound.

For example, as in Reaction Scheme 1, a phosphonium-based compound produced by a primary reaction of a phosphonium-based compound may include a combined whitening component. 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, a hydroxysuccinimide-based compound, a hydroxycarboximide-based compound, a hydroxytriazole-based compound, a hydroxybenzotriazole-based compound, a hydroxypyridinone-based compound, and a hydroxyphenylbenzene It may include at least one peptide bond formation reaction promoting additive selected from the group consisting of midazole-based compounds, hydroxyindolinone-based compounds, hydroxybenzotriazine-based compounds, and oxima. The term "based compound" means to include both hydroxybenzotriazole and hydroxybenzotriazole-containing compounds, for example, in the case of a hydroxybenzotriazole-based compound.

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 to 1 part by weight, more preferably 0.001 to 0.1 part by weight. Even if it is used in an amount of 10 parts by weight or more, the rate of chemical reaction is saturated, so the product is not economically viable and does not help the stability of the product. When used below 0.0001, it provides little or no benefit to reactivity.

In addition, in order to additionally increase the effect in the cosmetic composition for skin whitening according to the present invention, fatty acids such as palmitic acid and stearic acid, fatty alcohols, linear and branched long-chain alkyl quaternary ammonium salts Preparation can be facilitated when mixed with cationized surfactants such as cationized cellulose, cationized guar, cationized polymers such as cationized polyvinylpyrrolidone, silicone, and the like. In addition, for formulation into cosmetic formulations, solvents, surfactants, thickeners, stabilizers, preservatives, colorants, pH adjusters, metal ion sequestering agents, pearlescent agents, appearance improvers, emollients, pigments, powder particles, etc. Ingredients may be included incidentally. 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 may be used in the prescription of a cosmetic composition for whitening, including a component having a whitening function having a functional group. 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, It may include both non-woven fabrics and sheets, and examples of application of skin products generally include basic cosmetics (toilet, serum, essence, lotion, cream, etc.) for skin care and protection, color cosmetics (make-up base, foundation, powder, Eye shadow, lip gloss, lipstick, lip balm, etc.), makeup for hands and toenails (manicure, nutrients, strengthening agent, top coat, etc.), cosmetics for cleansing (foam cleansing, cleansing oil, cleansing lotion, cleansing cream, cleansing gel, pack, Masks, soaps, cleansing tissues, etc.), sun care cosmetics, and body cosmetics (body lotion, shower gel, body cream, body oil, etc.) can all be included.

More preferably, the cosmetic for skin whitening according to the present invention includes a whitening component having a reactive functional group as well as a phosphonium-based compound, and when the activity of the above formulation is reduced in an aqueous system, its activity is reduced in a non-aqueous formulation. It is easier to maintain, and the reaction can be caused by mixing with a buffer to adjust the pH immediately before use or by contact with water in the cleaning process. Examples of non-aqueous formulations include liquid form, sheet form, powder form, tablet form, oil, wax, ampoule, gel, etc., which are used as conventional non-aqueous cosmetic formulations. In addition, the phosphonium-based compound and the whitening component may be formulated as a single agent in encapsulated form or in two separate forms. In addition, 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, 2-base acid ester oil such as dioctylsuccinate, dioctyl adipate, diethyl sebacate, etc., polyol, polyethylene glycol, propylene glycol, Hexylene glycol, butanediol and their isomers, glycerol, benzyl alcohol, ethoxydiglycol and derivatives thereof may be used. The above-mentioned solvent increases the permeability of hair or skin and is used as a solvent for poorly soluble substances. More preferably, solvents used to increase the effect of maintaining the activity of a whitening component having a functional group include 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 to illustrate 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 grams ) Formulation of mask pack manufacturing

A mask pack of a cream formulation was prepared with the composition and content shown in Table 1 below.

Water phase raw materials 3 to 13 were heated to 70 °C and uniformly mixed for 5 minutes at 1500 rpm using a homomixer. Oil phase components 15 to 24 previously dissolved by heating at 70 ° C were added to the mixed aqueous phase and mixed uniformly for 5 minutes at 3500 rpm using a homo mixer. After that, the temperature was lowered to 50 ℃, and a neutralizing agent, polystyrene supported (Benzotriazol-1-yloxy)-tris(dimethylamino)phosphonium hexafluorophosphate) (PS-BOP) 1, a phosphonium-based compound, and 1-Hydroxybenzotriazole (HOBt), an additive for promoting peptide bond formation, were used. 2 and spice 14 were added later, mixed uniformly for 3 minutes with a homomixer, and then degassed, filtered, and cooled.

In the PS-BOP, R ₁ in Formula 1 is represented by the following Formula 2 (m + n + x + y: z = 99: 1 molar ratio), and is a resin-type polymer resin having a weight average molecular weight of 200,000 Da ; R ₂ is benzotriazole-yloxy; R ₃ to R ₅ are dimethylamino. The z is a crosslinker that randomly connects between polymers without being attached to a specific position, Eur . J. Org . Chem . It was synthesized by referring to 2004, 1936_1939.

[Formula 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 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 spices 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 a phosphonium-based compound, the efficacy was confirmed.

The mask pack formulations of Comparative Example 1 and Example 1 were prepared, respectively, and applied to 7 subjects to confirm changes in skin brightness. 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 then washing it again. Skin brightness was confirmed with LAB measuring equipment (Konica Minolta CR-300 Chroma Meter).

As a result of the experiment, when glucosamine was attached using a phosphonium-based compound (Example 1), it was confirmed that the brightness of the skin was improved by 1.18% for 2 weeks [Fig. 1]. Compared to Comparative Example 1, the whitening effect of Example 1 was significantly improved.

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

Experimental example 2

After attaching glucosamine to the skin by bioconjugation using a phosphonium-based compound, the efficacy was confirmed.

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

Changes in skin brightness were evaluated through a user questionnaire. Items such as moisturizing, whitening, and elasticity were set, and the user's perceived improvement was confirmed by setting X if it was similar to usual and O if it felt better.

As a result of the experiment, it was confirmed that when glucosamine was attached to the skin using a bioconjugation method using a phosphonium-based compound, the brightness of the skin experienced by the user was improved by more than 80% for one week [FIG. 2]. Compared to Comparative Example 1, the whitening effect of Example 1 was significantly improved.

It is expected that various whitening ingredients as well as glucosamine can be attached to the skin by bioconjugation method and left for a long time to continuously obtain the whitening effect 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 attaching chitosan to the skin using bioconjugation of a phosphonium-based compound, the efficacy was confirmed. (By preventing aging or oxidation of the skin surface, the yellowing was reduced and the tone was adjusted to confirm the skin whitening effect)

The mask pack formulations of Comparative Example 2 and Example 3 were prepared, respectively, and applied to the cheeks of 7 subjects to confirm changes in skin yellowness and gloss, 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 then washing it again. Yellowness was checked with LAB measuring equipment (Konica Minolta CR-300 Chroma Meter), and gloss change was checked with gloss meter (C&K MPA 580, skin glossymeter GL200).

As a result of the experiment, when chitosan was attached using the bioconjugation method of a phosphonium-based compound (Example 3), it was confirmed that skin yellowness was improved by 5.82% after 2 weeks of use due to the antioxidant and anti-aging ability of chitosan, It was also confirmed that skin gloss was also improved by 4.98% after 2 weeks of use [Figs. 3 and 4]. Compared to Comparative Example 2, the whitening effect of Example 3 was significantly improved.

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

Example 4-5 and comparative example 3~4: Non-woven mask pack manufacturing

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, water phase raw materials 1, 8, 9, 10, 11, 14, 15, and 16 were heated to 70° C. and then uniformly mixed for 5 minutes at 1500 rpm using a homomixer. Oil phase components 5, 6, 7, 12, and 13 previously dissolved by heating at 70 ° C were added to the mixed aqueous phase and mixed uniformly for 5 minutes at 2000 rpm using a homo mixer. Thereafter, the temperature was lowered to 50° C., PS-BOP 2, HOBt 3, Glucosamine 4, and Flavor 17 were added thereto, mixed uniformly for 3 minutes with a homomixer, and then defoamed, filtered, and cooled. Then, the non-woven mask was 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 2.0 2.0 2.0 2.0 16 Hydroxyethylcellulose 0.4 0.4 0.4 0.4 17 spices 0.1 0.1 0.1 0.1

Experimental example 4: Skin brightness improvement evaluation

After attaching glucosamine to the skin using bioconjugation of a phosphonium-based compound, the efficacy was confirmed. Mask pack formulations of Comparative Examples 3 to 4 and Examples 4 to 5 were prepared and applied to 7 subjects to confirm changes in skin brightness.

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 then washing it again. Skin brightness was confirmed with LAB measuring equipment (Konica Minolta CR-300 Chroma Meter).

Then, the difference (L*) in skin color at the time of measurement and the start of application after application of each test material 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 L* of the sample application area and the control area. If the L* value is about 2, the whitening of the deposited pigment is obvious, and if it is about 1.5 or more, it can be judged that there is a whitening effect. .

[Equation 1]

ΔL = 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 phosphonium-based compounds confirmed that the whitening effect was significantly improved for 2 weeks when PS-BOP and PS-HOBt were used. .

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

Claims (17)

A cosmetic composition for skin whitening comprising a phosphonium-based compound represented by Formula 1 and a skin whitening component:
[Formula 1]

In Formula 1,
R ₁ represents a polymer resin in the form of a resin,
R ₂ may be one selected from the group consisting of benzotriazole-yloxy, azabenzotriazole-yloxy, and nitrobenzotriazole-yloxy;
R ₃ to R ₅ are the same as or different from each other, and are dialkylamino-based compounds having 1 to 10 carbon atoms.
delete delete delete According to claim 1,
The polymer resin in the form of the resin is a cosmetic composition for skin whitening having a weight average molecular weight of 1,000 Da or more and less than 300,000 Da.
According to claim 1,
The resin-type polymer resin is styrene, ethylene, butadiene, acrylonitrile, methyl styrene, terephthalate, ethylene chloride, ether ketone, ether imide, ether sulfone, phthalamide, phenylene ether, phenylene oxide, phenylene sulfide, A cosmetic composition for skin whitening, which is a polymer polymerized with a monomer selected from the group consisting of sulfone, urethane, vinylidene fluoride and tetrafluoroethylene.
delete According to claim 1,
The phosphonium-based compound is 0.001 to 10 parts by weight based on 100 parts by weight of the total composition cosmetic composition for skin whitening.
According to claim 1,
The skin whitening component is a cosmetic composition for skin whitening comprising a carboxyl group or an amine group in a molecule.
According to claim 1,
The skin whitening component may include vitamins and derivatives thereof; flavonoid compounds; resveratrol compounds and their derivatives; curcubitacin derivatives; amino acid-based compounds; Arbutin, kojic acid, azelaic acid, alpha hydroxy acid, alpha-bisabolol, adenosine, ascorbyl glucoside, ascorbyl tetraisopalmitate, ethyl ascorbyl ether, fullerene, acetyl tyrosine, diacetylbenzoylatirol, white lily oil, Magnesium Ascorbyl Phosphate, Diosmetin, Mayslignan, Acetylsphingosine, Dihydroxymethoxychalcone, Alpha-Bisabolol, Protocatechuic Aldehyde, Oryzanol, Licorice Extract, Paper Mulberry Extract, Green Tea Extract, Mortar Extract, Adlay Extract, Yeast Extract, Baekchul Extract, Wheat Germ Extract, Peony Extract, Root Extract, Ginseng Extract, Red Ginseng Extract, Sambaekcho Extract, Agrimony Extract, Indian Canna Root Extract, Jeju Sasa Extract, Gosam Extract, Uiyiin Extract, Western Plum Extract, Chitosan At least one cosmetic composition for skin whitening selected from the group consisting of polylysine, glucosamine, and derivatives thereof.
According to claim 1,
The skin whitening component is a cosmetic composition for skin whitening having a functional group capable of covalent bonding with a protein residue on the skin surface.
According to claim 11,
Functional groups covalently bonded to the protein include carbodiimide, imidoester, arylazide, diazirine, hydroxymethyl phosphine, pentafluorophenyl ester, pyridyl disulfide, sulfo-hydroxysuccinimide ester, alkoxy amine, Hydrazides, haloacetyls, azides, carbonates, aldehydes, propionaldehydes, butyraldehydes, nitrophenyl carbonates, aziridines, isocyanates, thiocyanates, epoxides, tresylates, succinimides, hydroxysuccinimidyl esters , imidazoles, oxycarbonyl amidazoles, imines, thiols, maleimides, vinylsulfones, ethylenimines, thioethers, acrylonitriles, acrylic acid or methacrylic acid esters, disulfides, ketones, carboxylic acids and phosphates. At least one cosmetic composition for skin whitening.
In the first,
The skin whitening component is 0.001 to 50 parts by weight based on 100 parts by weight of the total composition cosmetic composition for skin whitening.
In the first,
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 formation reaction promoting additive is a hydroxysuccinimide-based compound, a hydroxycarboximide-based compound, a hydroxytriazole-based compound, a hydroxybenzotriazole-based compound, a hydroxypyridinone-based compound, a hydroxyphenylbenzimidazole-based compound , At least one cosmetic composition for skin whitening selected from the group consisting of hydroxyindolinone-based compounds, hydroxybenzotriazine-based compounds, 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 cosmetic composition for skin whitening.
According to claim 1,
The phosphonium-based compound and the skin whitening component are formulated as a single agent in an encapsulated form; A cosmetic composition for skin whitening formulated in two separate forms of a phosphonium-based compound and a skin whitening component.

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