KR102006948B1 - Cosmetics compositions for skin whitening t - 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 to form a covalent bond without damaging the skin to provide a semi-permanently desired whitening effect.

Description

Cosmetic compositions for skin whitening

The present invention relates to a reactive skin whitening component having a functional group binding to a protein and a cosmetic composition for skin whitening.

Generally, whitening cosmetics are applied to the body in order to brighten the color or tone of a person's skin, to beautify the skin defects such as spots and blemishes, to increase charm, to change appearance, or to keep the skin healthy. It is intended to be used in a similar way to spraying, scattering, and others. In addition, quasi-drugs are defined as having a mild action and not used for the treatment or prevention of diseases, but do not have a purpose for use such as affecting the structure and function of the body.

Whitening cosmetics generally include a part of skin whitening cosmetics for preparing and protecting the skin, makeup whitening cosmetics for bases, points, and nails, and body whitening cosmetic products such as washing, sun care and sun tenning.

In general, the color of the skin is known to depend on melanin. The production of melanin is promoted by stimulation such as ultraviolet rays or inflammation. Therefore, in order to reduce the production of melanin pigment, there are ways to reduce external stimuli such as ultraviolet rays, block the signal transmitted to melanocytes, or inhibit or inhibit the synthesis of melanin-forming enzyme tyrosinase. Can be. In addition, there is a method for reducing the melanin produced or discharged to the outside by the exfoliation action.

Common raw materials used to make up these whitening cosmetics include oily materials such as fats, waxes, hydrocarbons, higher fatty acids, higher alcohols, ester oils, silicone oils, anions, cations, amphoteric, nonionic surfactants, humectants, It contains polymer compounds used as thickeners and film-forming agents, ultraviolet absorbers and blockers, antioxidants, metal ion sequestrants, colorants including dyes and pigments, fragrances, and preservatives.

In addition, the active ingredient acting on the actual whitening function, such as UV-protective components such as octylmethoxycinnamate, oxybenzone, titanium oxide, zinc oxide, stimulation or signal transduction control components such as imerin, chamomile extract, phytoclear EL -1, tyrosinase synthesis inhibitors such as white oil, arbutin, licorice extract, mulberry extract, lettuce extract, tyrosinase inhibitors, vitamin C and derivatives, melanin reducing components such as glutathione, coenzyme Q10, AHA (α-hydroxy acid), Keratin depletion promoting ingredients such as salicylic acid, keratinase is mainly used. In addition to these whitening ingredients, kojic acid, niacin amide, ascorbyl glucoside, magnesium ascorbyl phosphate, acetyl tyrosine, fullerine, oryzanol, methoxypiji-7 ascorbic acid, methyl undecenoyl leucineate, diacetylbenzoylatirrole, proto Catechuic aldehyde, alpha-bisabolol, dihydroxymethoxychalcone, acetylphytosphingosine, polydatin, diosmethine, azelaic acid, mayslignan, vitamins, hormones, amino acids, ginseng extract, Extracts derived from natural products such as red ginseng extract, black ginseng extract, root root extract, triticale extract, agrimoni extract, indochona root extract, jeju stalk extract, red ginseng extract, uiyiin extract, baekchul extract, wheat germ extract, baekchul oil, western plum extract And the like.

However, when used on the skin with such a whitening ingredient only provides a temporary effect until the next cleaning after treatment, there is always a hassle to be reprocessed after cleaning.

Patent document 1 relates to a skin non-aqueous personal care product, and is a functional group capable of covalently bonding to protein residues on the surface of the skin in non-aqueous parts. ), Nitrophenyl carbonate, aziridine, isocyanate, thiocyanate, epoxide, tresylate, succinimide, hydroxy Hydroxysuccinimidyl ester, imidazole, oxycarbonylamidazole, imine, thiol, maleimide, vinylsulfone, ethyleneimine ), Thioether, acrylonitrile, acrylic acid or methacrylic ester, disulfide, ke At least one selected from the group consisting of a ketone and a functional group represented by RX (R is any one selected from the group consisting of alkyl, aryl, aralkyl, a ring and an unsaturated ring, and X is I, Br, or Cl) Although it contains a conditioning ingredient having a non-aqueous part and a water-based part, and discloses a personal care product for skin characterized in that the mixture is used immediately before use, the various functional groups described above are harmful to the human body or Among the amino acids of the protein constituting the skin, the target is lysine containing a small amount of skin keratin (3.1 ~ 6.9%), or cysteine of hair (16.6-18%) and skin keratin (2.3 ~ 3.8%). Because of the targeted reaction, the reaction efficiency is lowered, and there is a problem that each material must be synthesized separately.

Korean Unexamined Patent No. 2008-0064467

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

As a means for solving the above problems, the present invention provides a cosmetic composition for skin whitening comprising a carbodiimide compound and a skin whitening component.

As another means for solving the above problems, the present invention is a skin whitening component, carbodiimide, imido ester, aryl azide, diazirine, hydroxymethyl phosphine, pentafluorophenyl ester, pyridyl disulfide, sulfo- Provided is a reactive skin lightening component having a functional group covalently bonded to a protein on at least one skin surface selected from the group consisting of hydroxysuccinimide esters, alkoxy amines, hydrazides, haloacetyls and azides.

As another means for solving the above problems, the present invention provides a cosmetic composition for skin whitening comprising the reactive skin whitening component.

The cosmetic composition for skin whitening according to the present invention contains a reactive skin whitening component and / or a carbodiimide-based compound incorporating a specific functional group capable of covalently bonding with protein residues of the skin, thus forming a covalent bond without damaging the skin and thus semipermanently. It gives skin whitening effect.

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

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

The carbodiimide-based compound may be included in an amount of 0.001 to 10% by weight, 0.01 to 7% by weight, or 0.1 to 5% by weight based on 100% by weight of the total cosmetic composition. If the content thereof is less than 0.001% by weight, there is a problem in that it is difficult to show a continuous whitening improvement effect. If the content exceeds 10% by weight, the carbodiimide compound that is excessively present beyond the reaction site present on the skin does not react with the skin. There is a problem that can act as a component that does not help to improve the sustainability by reacting with the agonist material.

In the present invention, the term "whitening effect" refers to a function of brightening the color or tone of the skin, or by beautifying the skin defects such as blemishes.

The skin whitening component used in the present invention may include a whitening component that can improve the site damaged by melanin pigmentation of the skin, such as extracts derived from natural products such as copper, plants, minerals, amino acids, hormones, vitamins, etc. This is not restrictive. For example, kojic acid, niacin amide, ascorbyl glucoside, magnesium ascorbyl phosphate, acetyltyrosine, fullerine, oryzanol, methoxypiji-7 ascorbic acid, methylundecenoylleucinate, diacetylbenzoylatilol, protocatechuic Aldehydes, alpha-bisabolol, dihydroxymethoxychalcone, acetylphytosphingosine, polydatin, diomethine, azelaic acid, mayis lignan, ginseng extract, red ginseng extract, black ginseng extract, root root extract, triticale It may be at least one selected from the group consisting of extracts, agrimoni extract, indokhanna root extract, jeju gorge extract, red ginseng extract, uiyiin extract, baekchul extract, wheat germ extract, baekchul oil and prune extract.

The whitening component is preferably used in 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 part by weight, there is a problem of effective performance limitation, and if it exceeds 50 parts by weight, there is a problem in formulation and formulation stabilization.

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

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

The functional group covalently bonded with the protein is carbodiimide, imido ester, aryl azide, diazirine, hydroxymethyl phosphine, pentafluorophenylester, 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 amidazole, imine, thiol, maleimide, vinylsulfone, ethyleneimine, thioether, acrylonitrile, acrylic acid or methacrylic acid ester, disulfide and ketone This is not restrictive.

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

The carbodiimide-based compound is a generic term for a compound containing a structure represented by the following formula (1) in a molecule.

[Formula 1]

-N = C = N-

The carbodiimide-based compound preferably includes at least 1 to 1000 structures of Formula 1, more preferably 1 to 100 structures represented by Formula 1 in a molecule, It is more preferable to include 1 to 10 structures represented in the molecule.

In this case, when the number of carbodiimide groups represented by the formula (1) in one molecule exceeds 1000, the viscosity of the raw material is too large, the molecular weight is too large, and the reaction sites that can react too much are excessively large, and The molecule | numerator which has a bodyimide group becomes so large that the problem which efficiency falls by covering the part which shows the functional effect of the molecule which has a substantial function arises.

Specific examples of the carbodiimide-based compound in the present invention may be a compound represented by the following formula (2), n is 4 and m is 11 in the formula (2) is benzene, 1,3, -bis (1- Isocyanato-1-methylethyl)-, homopolymer, polyethylene glycol mono-meth-ether-block (Benzene, 1,3-bis (1-isocyanato-1-methylethyl)-, homopolymer, polyethylene glycol mono- Me-ether-blocked) (hereinafter referred to as polymer type carbodiimide compound of Formula 2).

(2)

In Formula 2, n is 1 to 100, m is 1 to 100.

In another embodiment of the carbodiimide-based compound in the present invention, as a compound represented by the following formula (3), 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide (1-Ethyl-3- (3-dimethylaminopropyl) carbodiimide) or 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide HCl (1-Ethyl-3- (3-dimethylaminopropyl) carbodiimideHCl) can be used.

(3)

In a preferred embodiment of the cosmetic composition for skin whitening according to the present invention, the skin whitening component having a carboxyl group is made in the form of a reactive ester skin whitening component having direct bioreactivity, or is present in an excess of skin keratin (15.5-23.5%). Reactive esterification of amino acids (ex, aspartic acid, glutamic acid) to produce reactive ester forms (reactive skin whitening components) using carbodiimide compounds that can be targeted by whitening components containing amine groups, thereby increasing the reaction efficiency The effect can be increased significantly. In addition, carbodiimides, imidoesters, arylazides, diazirines, hydroxymethyl phosphines, pentafluorophenylesters, pyridyl disulfides, sulfo-hydroxysuccinimide esters, alkoxy, which may target other amino acids The effect can be further enhanced by using a skin whitening component comprising a functional group such as amine, hydrazide, haloacetyl, azide in the molecule.

In a more preferred embodiment, the skin whitening component molecule having a carboxyl group or the surface of the protein of the skin is first a polymer form carbodiimide compound of formula (2) or 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide. Carbodiimide-based compounds such as (1-ethyl-3- (3-dimethylaminopropyl) carbodiimide.HCl) are first reacted to form a reactive ester, and the whitening component having an amine in the molecule is reacted with the formed reactive ester functional group. Or by reacting with an amine on the surface of the skin, an excellent skin whitening effect can be obtained. In the reaction, the reaction may be preferably performed at a pH of 2 to 10, more preferably at a pH of 3 to 9, and most preferably at a pH of 4 to 5 in an acidic to weakly acidic aqueous solution. The most reaction efficiency can be increased. The reaction is completed within 1 to 30 minutes.

In Scheme 1, a skin whitening component molecule having a carboxyl group was first reacted with a carbodiimide-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.

[Reaction Scheme 1]

In the following scheme 2, aspartic acid and glutamic acid, which are biological amino acids having a carboxyl group on the surface of the protein of the skin, are first reacted with a carbodiimide-based compound to form a reactive ester, followed by reaction with a skin whitening component having an amine residue to form a covalent bond. The reaction schematic is shown.

[Reaction Scheme 2]

Carbodiimide-based compounds enhance the reaction efficiency of skin proteins and skin whitening ingredients, and the reactive skin whitening ingredients bound to the skin do not come off during normal cleaning due to shampoo or soap and are almost permanently attached to the skin. State can be maintained.

The present invention also provides carbodiimide groups, imidoesters, arylazides, diazirines, hydroxymethyl phosphines, pentafluorophenylesters, pyridyl disulfides, sulfo-hydroxysuccinimide esters, and alkoxy to skin whitening components. Amine, hydrazide, haloacetyl, azide, carbonate, aldehyde, propionaldehyde, butylaldehyde, nitrophenyl carbonate, aziridine, isocyanate, thiocyanate, epoxide, tresylate, succinimide, hydroxysuccinimide One or more selected from the group consisting of dill esters, imidazoles, oxycarbonyl amidazoles, imines, thiols, maleimides, vinylsulfones, ethyleneimines, thioethers, acrylonitrile, acrylic acid or methacrylic acid esters, disulfides and ketones It may contain a reactive skin whitening ingredient combined with a functional group covalently bound to a protein. have.

For example, as shown in Scheme 1, the carbodiimide group may include a skin whitening component having a carbodiimide group bonded thereto. In addition, the present invention may include a cosmetic composition for skin whitening comprising the reactive skin whitening component.

In the cosmetic composition for skin whitening according to the present invention for improving incidental effects, cations such as fatty acids such as palmitic acid and stearic acid, fatty alcohols, long-chain alkyl quaternary ammonium salts of straight and branched chains, etc. Formulation may be facilitated when used in combination with cationic polymers such as cationic surfactants, cationic cellulose, cationic guar, and cationic polyvinylpyrrolidone, and silicones. In addition, to formulate into cosmetic formulations for the formulation of cosmetics such as solvents, surfactants, thickeners, stabilizers, preservatives, colorants, pH adjusters, metal ion sequestrants, colorants, pearlescent agents, cosmetics, pigments, powder particles, etc. Components may be incidentally included. The component for the formulation may be used 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 for the preparation of the cosmetic composition for skin whitening including the component of the whitening function having a functional group. Examples of application of skin products generally include skin care, basic cosmetics (cosmetics, serums, essences, lotions, creams), color cosmetics (makeup base, foundation, powder, eye shadow, lip gloss, lipstick, lip balm, etc.) , Makeup for nails (nail polish, nutrients, reinforcing agents, top coats, etc.), cleaning cosmetics (foam cleansing, cleansing oil, cleansing lotion, cleansing cream, cleansing gel, pack, mask, soap, cleansing tissue, etc.), sun care Cosmetics, body cosmetics (body lotion, shower gel, body cream, body oil, etc.) may include all.

More preferably, the cosmetic composition for skin whitening according to the invention comprises a skin whitening component which contains a carbodiimide-based compound and at the same time a reactive functional group. It is easier to maintain the activity and may be reacted by mixing with a buffer just before use to adjust the pH or by contacting with water during the cleaning process. Examples of non-aqueous formulations include liquid form, sheet form, powder powder form, tablet form, oil, wax, ampoule, gel and the like used as conventional non-aqueous cosmetic preparations. In addition, the carbodiimide compound and the skin lightening component may be formulated as a single agent in encapsulated form or as two agents in separate forms, respectively. In addition, a method of blocking derivatives in a form in which a reactive functional group and a component having a whitening function are combined with water through encapsulation may also be used.

In order to increase the whitening effect having a functional group in the cosmetic composition for skin whitening according to the present invention, 2-basic acid ester oil such as dioctyl succinate, dioctyl adipate, diethyl sebacate and the like, 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 the skin and are used as solvents of poorly soluble substances. More preferably, solvents used to increase the activity retention effect of the whitening component having a functional group include diethyl sebacate, ethoxyglycol, bis-ethoxyglycol 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 6 and Comparative Example  1-3

The whitening compositions of Examples 1 to 6 and Comparative Examples 1 to 3 were prepared using the compositions and contents shown in Table 1 below. 3 g of each of the prepared compositions was applied to 20 subjects on the back of an arm and left for 30 minutes to induce a reaction. After rinsing with first flowing water, the process of washing with soap and drying was repeated five times, once daily. The whitening effect was then compared with the sensory of 5-point scale (5 very good, 4 slightly better, 3 no difference, 2 no effect, 1 very no effect), and after 10 days the 5-point scale (5 very good, 4 slightly better) , 3 no difference, 2 no effect, 1 very no effect) to compare the whitening effect was confirmed the persistent effect.

Category (% by weight) Comparative Example 1 Comparative Example 2 Comparative Example 3 Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 Distilled water 49.0 49.0 49.0 48.0 48.0 48.0 48.0 48.0 48.0 Niacin
Amide 1.0 - - 1.0 - - 1.0 - - Acetyltyrosine - 1.0 - - 1.0 - - 1.0 - Azelaixan - - 1.0 - - 1.0 - - 1.0 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide. Hydrochloric acid - - - 1.0 1.0 1.0 - - - Benzene, 1,3, -bis (1-isocyanato-1-methylethyl)-, homopolymer, polyethylene glycol mono-meth-ether-block - - - - - - 1.0 1.0 1.0 Buffer
(pH 4.5) 50.0 50.0 50.0 50.0 50.0 50.0 50.0 50.0 50.0 Sum 100.0 100.0 100.0 100.0 100.0 100.0 100.0 100.0 100.0

Experimental results of Examples 1 to 6 and Comparative Examples 1 to 3 (Table 2), Examples including carbodiimide compared to Comparative Examples 1 to 3 where the bioreactive group does not contain a carbodiimide as a whitening component that is not substituted 1 to 6 showed better whitening and sustainability due to the covalent bond formation effect of carbodiimide, and Examples 4 to 6 using polymer carbodiimide showed the best whitening and whitening sustaining effect.

division Comparative Example 1 Comparative Example 2 Comparative Example 3 Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 Immediately after treatment 3.0 2.9 3.2 3.6 3.6 3.5 4.1 4.0 4.0 After 10 days 2.5 2.3 2.4 3.3 3.2 3.3 3.5 3.4 3.6

Formulation example : Whitening Cosmetics  Produce

According to the conventional cosmetic preparation method, a whitening cosmetic was prepared with the ingredients and contents of Table 3 below.

Component (% by weight) toilet water Lotion cream pack Niacinamide 1.0 1.0 1.0 1.0 Benzene, 1,3, -bis (1-isocyanato-1-methylethyl)-, homopolymer, polyethylene glycol mono-meth-ether-block 1.0 1.0 1.0 1.0 glycerin 3.0 3.0 3.0 3.0 Butylene glycol 3.0 3.0 3.0 - Propylene glycol 3.0 3.0 - - Carboxyvinyl polymer 0.1 0.1 0.1 - Polyvinyl alcohol - - - 15.0 Phage-12 nonylphenyl ether 0.3 - - 0.5 Polysorbate 80 0.5 - - - Polysorbate 60 - 1.5 1.5 1.5 Sorbitacecequioleate - 1.5 - - Sorbitan stearate - - 0.5 - Liquid paraffin - 0.5 10.0 - Caprylic / capric triglyceride - 5.0 5.0 - Squalane - 5.0 5.0 - Cetearylglucoside - - 2.0 - ethanol 10.0 - - - Triethanolamine 0.1 0.1 0.1 - Cetearyl alcohol - 1.0 - - Wax - 5.0 - - antiseptic Suitable amount Suitable amount Suitable amount Suitable amount Spices Suitable amount Suitable amount Suitable amount Suitable amount Buffer (pH 4.5) Balance Balance Balance Balance Sum 100 100 100 100

Claims (9)

A carbodiimide compound represented by the following formula (2); And a skin whitening component having a functional group capable of covalently bonding with a protein residue on the surface of the skin:
(2)

In the above formula (2), n is 1 to 100 and m is 1 to 100.
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 the molecule.
The method of claim 1,
The skin whitening component is kojic acid, niacin amide, ascorbyl glucoside, magnesium ascorbyl phosphate, acetyl tyrosine, fullerine, oryzanol, methoxypiji-7 ascorbic acid, methyl undecenoyl leucineate, diacetyl benzoyl tyrol, protocate Chewing aldehyde, alpha-bisabolol, dihydroxymethoxychalcone, acetylphytosphingosine, polydatin, diosmethine, azelaic acid, mayis lignan, ginseng extract, red ginseng extract, black ginseng extract, root root extract, A cosmetic composition for skin whitening, which is at least one selected from the group consisting of trichoola extract, agrimoni extract, indochona root extract, jeju stalk extract, red ginseng extract, uiyiin extract, baekchul extract, wheat germ extract, baekchul oil and prune extract.
delete The method of claim 1,
The functional group covalently bonded with the protein is imidoester, arylazide, diazirine, hydroxymethyl phosphine, pentafluorophenylester, 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, Cosmetic composition for skin whitening which is at least one selected from the group consisting of oxycarbonyl amidazole, imine, thiol, maleimide, vinylsulfone, ethyleneimine, thioether, acrylonitrile, acrylic acid or methacrylic acid ester, disulfide and ketone.
The method of claim 1,
A cosmetic composition for skin whitening, wherein the carbodiimide compound is contained in an amount of 0.001 to 10% by weight in 100% by weight of the total composition.
The method of claim 1,
The carbodiimide compound and the skin lightening component are formulated in a single agent in encapsulated form; A cosmetic composition for skin whitening, wherein the carbodiimide-based compound and the skin whitening component are formulated in two separate forms.
delete delete