KR20150066826A - Cosmetics compositions for prevention and improvement of wrinkle - Google Patents

Abstract

The present invention relates to a cosmetic composition for preventing and improving wrinkles. The cosmetic composition for preventing and improving wrinkles according to the present invention contains a wrinkles preventing or improving component with a specific functional group enabling a covalent bond with protein residues on the surface of skin to form the covalent bond without damage to the skin, thereby providing a desired semipermanent wrinkles preventing and improving effect.

Description

[0001] Cosmetic compositions for prevention and improvement of wrinkles [

The present invention relates to a composition for preventing and improving wrinkles and a cosmetic composition for preventing and improving wrinkles, the functional group being bonded to a protein.

In general, the composition for preventing and improving wrinkles refers to a composition for preventing or improving wrinkles, which is applied to skin for the purpose of preventing wrinkles formed on human skin, especially facial parts, It is intended to be used in a similar manner to the others, and refers to a slight action on the human body.

It is defined that quasi-drugs do not have the purpose of use such as affecting the structure and function of the body, and not being used for treatment or prevention of diseases, even if the action is on the human body.

Wrinkles are a typical example of signs of aging, and preventing or improving it's occurrence is a big part of cosmetics, along with the desire of many women. The types and symptoms of aging are firstly natural skin aging caused by degenerative changes, resulting in thinning of the skin and smoothing and sagging of the epidermis and dermis. The photoaging by ultraviolet rays causes abnormal cell arrangement and cell polarity.

The factors involved in such wrinkling are known to be various, such as sunlight, skin elastin, collagen, substrate, vascular disorders, and active oxygen. Common methods and working principles for improving these wrinkles are vitamin C, vitamin A ), Peptides, etc., to stimulate cell regeneration by increasing collagen synthesis and by using antioxidative activities of vitamin E (tocopherol), flavonoid, polyphenol, SOD, coenzyme Q10 and alpha lipoic acid to produce lipid peroxides And a method of decreasing muscle motion by using acetyl hexapeptide or the like called so-called botox.

The cosmetic composition for wrinkle prevention and improvement generally includes a composition for preventing and improving wrinkles such as a composition, a base, and a point of a wrinkle prevention and restoration function for cleansing, arranging, and wiping the skin for care of the skin and a composition for bath, sun care, sun tanning, Restraint, deodorization, hair loss, hair removal, and the like.

Common raw materials used for constituting the cosmetic composition for prevention and improvement of wrinkles include oily materials such as oils, waxes, hydrocarbons, higher fatty acids, higher alcohols, ester oils and silicone oils, anionic, cationic, amphoteric and non- Antioxidants, metal ion sequestrants, colorants including dyes and pigments, fragrances, preservatives, and the like, as long as they are compatible with the present invention.

In addition, as a wrinkle preventing and improving functional ingredient for providing a special performance, vitamin A (retinoid) and its derivatives, peptides, vitamin E (tocopherol) and its derivatives, flavonoid, polyphenol, SOD, coenzyme Q10, A wrinkle ingredient such as hexapeptide, retinol, retinyl palmitate, adenosine, vitamin C, collagen, hexapeptide 3, EGF, kinetin, snail mucilage, aquanomide, ceramide, glycerin, hyaluronic acid, betaine, chitosan, vitamin Moisturizing agents such as E (tocopherol), urea (Urea), and the like.

However, when the composition is applied to the skin as a composition for preventing and improving wrinkles and preventing and improving wrinkles, it only provides a temporary effect until the next cleaning after the treatment, but there is always a need to reprocess after cleaning.

Patent Document 1 discloses a skin non-aqueous personal care product which comprises a non-water-based functional group capable of forming a covalent bond with a protein moiety of hair or skin surface on a non-water-based part, such as carbonate, aldehyde, propionaldehyde, but are not limited to, butylaldehyde, nitrophenyl carbonate, aziridine, isocyanate, thiocyanate, epoxide, tresylate, succinimide, (S), hydroxysuccinimidyl ester, imidazole, oxycarbonylamidazole, imine, thiol, maleimide, vinylsulfone, ethyleneimine ethyleneimine, thioether, acrylonitrile, acrylic acid or methacrylic ester, disulfide (d (wherein R is any one selected from the group consisting of alkyl, aryl, aralkyl, cyclic and unsaturated rings, and X is I, Br or Cl) selected from the group consisting of isophide, ketone and RX. Discloses a personal care product for hair or skin characterized in that it contains a conditioning component having at least one of its components and is separated into a non-aqueous part and a water-based part and is mixed immediately before use. However, (16.6 ~ 18%), skin keratin (2.3 ~ 3.8%), and skin keratin (3.1 ~ 6.9%) in the amino acids of harmful or skin constituting proteins. ) Of cysteine is targeted and reacted, so that the reaction efficiency is lowered, and each of the substances must be separately synthesized.

Korean Patent Publication No. 2008-0064467

It is an object of the present invention to provide a cosmetic composition for prevention and improvement of wrinkles which can continuously impart the effect of preventing and improving wrinkles without damaging the skin.

As a means for solving the above problems, the present invention provides a cosmetic composition for prevention and improvement of wrinkles comprising a carbodiimide compound and a wrinkle preventing and improving component.

As another means for solving the above-mentioned problems, the present invention provides a wrinkle preventing and improving composition comprising at least one member selected from the group consisting of carbodiimide, imidoester, aryl azide, diazirine, hydroxymethylphosphine, pentafluorophenyl ester, pyridyl disulfide, At least one hair selected from the group consisting of sulfo-hydroxysuccinimide ester, alkoxyamine, hydrazide, haloacetyl, and azide, or a functional group covalently bonding with a protein on the surface of the skin, .

As another means for solving the above problems, the present invention provides a cosmetic composition for prevention and improvement of wrinkles containing the above-mentioned reactive wrinkle preventing and improving component.

The cosmetic composition for prevention and improvement of wrinkles according to the present invention contains a reactive wrinkle preventing and improving component and / or a carbodiimide compound into which specific functional groups capable of covalently bonding with protein residues of skin are incorporated, Thereby providing a semi-permanent anti-wrinkle prevention effect.

The present invention relates to a cosmetic composition for prevention and improvement of wrinkles comprising a carbodiimide compound and a wrinkle preventing and improving component.

The cosmetic composition for prevention and improvement of wrinkles according to the present invention can be produced by, for example, reacting a carbodiimide compound with a known wrinkle preventing and improving component to prevent and improve wrinkles, So that the effect of preventing and improving wrinkles can be maximized.

The carbodiimide compound may be used in an amount of 0.001 to 10 parts by weight, 0.01 to 7 parts by weight, or 0.1 to 5 parts by weight based on 100 parts by weight of the entire cosmetic composition. When the content is less than 0.001 part by weight, there is a problem that continuous wrinkle prevention and improvement effects are hard to be exhibited. When the content exceeds 10 parts by weight, a carbodiimide compound which is excessively present at a reaction site existing in the skin does not react with skin , There is a problem that it can act as a component to be lost, which does not help to improve persistence.

In the present invention, the term ' wrinkle prevention and improvement effect ' means a function of preventing wrinkles formed on the skin, particularly, the face portion, and restoring or healing and weaving.

The wrinkle preventing and improving component used in the present invention may include, but is not limited to, extracts derived from natural products such as copper, plants and minerals, amino acids, hormones, vitamins and the like. For example, there may be mentioned vitamin A (retinoid), vitamin E (tocopherol), flavonoid, polyphenol, superoxide dismutase (SOD), coenzyme Q10, alpha-lipoic acid, acetylhexapeptide, retinol, retinyl palmitate, retinyl acetate, A group consisting of adenosine, vitamin C, collagen, hexapeptide 3, skin cell growth factor (EGF), kinetin, snail mucilage, aquanomide, ceramide, glycerin, hyaluronic acid, betaine, chitosan, urea and derivatives thereof ≪ / RTI >

It is preferable that 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 of the anti-wrinkle agent is used with respect to 100 parts by weight of the entire cosmetic composition. If the content is less than 0.001 part by weight, there is a problem of effective performance limit. If the content is more than 50 parts by weight, there is a problem in formulation and formulation stabilization.

Particularly, in the present invention, the wrinkle preventing and improving component can increase the reaction efficiency with the carbodiimide compound by including a carboxyl group or an amine group in the molecule.

In the present invention, the wrinkle preventing and improving component may have a functional group capable of covalently bonding to protein residues on the skin surface.

The functional groups covalently bonded to the protein include carbodiimide, imidoesters, aryl azides, diazylines, hydroxymethylphosphines, pentafluorophenyl esters, pyridyl disulfides, sulfo-hydroxysuccinimide esters, alkoxy amines, The present invention also relates to a process for the preparation of a medicament for the treatment and / or prophylaxis of a disease or condition selected from the group consisting of hydrazide, haloacetyl, azide, carbonate, aldehyde, propionaldehyde, butylaldehyde, nitrophenylcarbonate, aziridine, isocyanate, thiocyanate, epoxide, May be at least one selected from the group consisting of imidazole, oxycarbonylamidazole, imine, thiol, maleimide, vinylsulfone, ethyleneimine, thioether, acrylonitrile, acrylic acid or methacrylic acid ester, disulfide and ketone , But is not limited thereto.

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

The carbodiimide compound is generally referred to as a compound containing a structure represented by the following formula (1) in the molecule.

[Chemical Formula 1]

-N = C = N-

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

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

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

(2)

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

Another example of the carbodiimide compound in the present invention is 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide, which is a compound represented by the following formula (3) carbodiimide or 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide.HCl may be used.

(3)

In a preferred embodiment of the cosmetic composition for prevention and improvement of wrinkles according to the present invention, the wrinkle preventing and improving component having a carboxyl group is directly made into a form of preventing and improving wrinkle of reactive ester having a bioreactivity or skin keratin (15.5 to 23.5 (Ex, aspartic acid, glutamic acid) in an excess amount in the form of a reactive esterification (reactive wrinkle prevention) using a carbodiimide compound capable of targeting a wrinkle preventing and improving component containing an amine group And the improvement component), thereby increasing the reaction efficiency and significantly increasing the effect. In addition, it is also possible to use carbodiimides, imidoesters, aryl azides, diazylines, hydroxymethylphosphines, pentafluorophenyl esters, pyridyl disulfides, sulfo-hydroxysuccinimide esters, alkoxy The effect can be further enhanced by using a wrinkle preventing and improving component containing a functional group such as amine, hydrazide, haloacetyl, or azide in the molecule.

In a more preferred embodiment, the polymeric carbodiimide compound of formula (2) or 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide A carbodiimide compound such as 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide.HCl is reacted first to form a reactive ester, and a wrinkle prevention and / By reacting the improving component with the amine on the skin surface, excellent wrinkle prevention and improvement effects can be obtained. The reaction is preferably carried out at a pH of 2 to 10, more preferably at a pH of 3 to 9, most preferably at an acidic to slightly acidic pH of about 4 to 5 The reaction efficiency can be increased most. The reaction is completed within 1 minute to 30 minutes.

In the following Reaction Scheme 1, a wrinkle preventing and improving component having a carboxyl group is firstly reacted with a carbodiimide compound to form a reactive ester, followed by reaction with an amino acid having an amine residue to form a covalent bond .

[Reaction Scheme 1]

In the following Reaction Scheme 2, asparaginic acid and glutamic acid, which are carboxylamino group-bearing biogenic amino acids on the surface of the skin, first react with a carbodiimide compound to form a reactive ester, and then react with a wrinkle preventing and improving component having an amine residue to form a covalent bond The reaction scheme is shown in Fig.

[Reaction Scheme 2]

The carbodiimide compound prevents skin wrinkles and wrinkles and improves the reaction efficiency of the components. Thus, the reactive wrinkle preventing and improving ingredients bonded to the skin do not fall off during general washing due to shampoo or soap, The skin can be kept attached to the skin.

The present invention also relates to the use of the wrinkle prevention and remediation component in the preparation of a wrinkle preventing and improving composition comprising a carbodiimide group, an imidoester, an aryl azide, a diazirine, a hydroxymethylphosphine, a pentafluorophenyl ester, a pyridyl disulfide, a sulfo-hydroxysuccinimide ester , Alkoxyamines, hydrazides, haloacetyls, azides, carbonates, aldehydes, propionaldehydes, butylaldehydes, nitrophenylcarbonates, aziridines, isocyanates, thiocyanates, epoxides, tresylates, succinimides, Selected from the group consisting of succinimidyl esters, imidazoles, oxycarbonylamidazoles, imines, thiols, maleimides, vinyl sulfones, ethyleneimines, thioethers, acrylonitriles, acrylic acid or methacrylic esters, disulfides and ketones Prevention and improvement of reactive wrinkles with functional groups covalently bonded to one or more proteins It may include minutes.

For example, as shown in Reaction Scheme 1, the carbodiimide compound may include a wrinkle preventing and improving component to which a carbodiimide group formed by a first reaction is bonded. In addition, the present invention may include a cosmetic composition for prevention and improvement of wrinkles containing the reactive wrinkle preventing and improving component.

In order to further enhance the effect of the cosmetic composition for prevention and improvement of wrinkles according to the present invention, fatty acids such as palmitic acid and stearic acid, fatty alcohols, long-chain alkyl quaternary ammonium salts of straight chain and branched chain, etc. The cationic surfactant, the cationic cellulose, the cationic guar, the cationic polymer such as cationized polyvinylpyrrolidone, silicone, etc., can be easily formulated. In order to formulate cosmetics such as solvents, surfactants, thickeners, stabilizers, preservatives, coloring agents, pH adjusters, metal ion sequestering agents, coloring agents, pearlizing agents, external appearance improvers, pigments and powder particles, Components may be incidentally included. The ingredients for the formulation may be used in an amount of 40 to 99 parts by weight based on 100 parts by weight of the total composition.

The cosmetic composition for prevention and improvement of wrinkles according to the present invention can be used for the preparation of a cosmetic composition for prevention and improvement of wrinkles including components having a wrinkle preventing and improving function having a functional group. Examples of applications of skin products include cosmetics (such as lotion, serum, essence, lotion, cream), color cosmetics (makeup base, foundation, powder, eye shadow, lip gloss, lipstick, lip balm, etc.) (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.).

More preferably, the cosmetic composition for prevention and improvement of wrinkles according to the present invention contains a carbodiimide compound and at the same time contains a wrinkle preventing and improving component having a reactive functional group. When the activity of the preparation is lowered in the aqueous system, It may be easier to maintain its activity in non-aqueous formulations and may be mixed with a buffer for pH control just prior to use, or may be brought into contact with water during the washing process. Examples of non-aqueous formulations include liquid, sheet, powder, tablet, oil, wax, ampoule, gel and the like which are used as ordinary non-aqueous cosmetic preparations. In addition, the carbodiimide compound and the wrinkle preventing and improving component can be formulated into a single product in the form of an encapsulated product or a two-component product in a separate form. In addition, a method of blocking a derivative having a reactive functional group and a component having a wrinkle preventing and improving function from moisture by encapsulation may also be used.

In order to enhance the effect of preventing and improving wrinkles having functional groups in the cosmetic composition for prevention and improvement of wrinkles according to the present invention, it is preferable to use 2-basic acid esters such as dioctyl succinate, dioctyl adipate, diethyl sebacate, Polyethylene glycol, propylene glycol, hexylene glycol, butanediol and isomers thereof, glycerol, benzyl alcohol, ethoxydiglycol and derivatives thereof. The above-mentioned solvents increase the permeability of the skin and are used as a solvent of a poorly soluble substance. More preferably, the solvent used for preventing the wrinkles having a functional group and enhancing the activity maintaining effect of the improvement component is diethyl sebacate, ethoxy glycol, bis-ethoxy glycol cyclohexane 1,4-dicarboxylate, and the like .

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

Example  1 to 2 and Comparative Example  One

The anti-wrinkle compositions of Examples 1 and 2 and Comparative Example 1 were prepared by the compositions and contents shown in Table 1 below. Each of the compositions prepared was applied to neck wrinkles of 10 subjects and allowed to stand at room temperature for 30 minutes (5 very excellent, 4 slightly superior, 3 no difference, 2 no effect, 2 no effect, 5 no effect, 10 no effect, 1, no effect was observed).

Category (% by weight) Comparative Example 1 Example 1 Example 2 water 49.0 48.0 48.0 Retinyl acetate 1.0 1.0 1.0 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride - 1.0 - Benzene, 1,3, -bis (1-isocyanato-1-methylethyl) -, homopolymers, polyethylene glycol mono-ether- - - 1.0 The buffer (pH 4.5) 50.0 50.0 50.0 Sum 100.0 100.0 100.0

The results of the tests of Examples 1 and 2 and Comparative Example 1 (Table 2) and Comparative Examples 1 and 2, which contain no carbodiimide and contain retinyl acetate, show that carbodiimide- The wrinkle-improving effect was more excellent owing to the covalent bond formation effect, and in particular, the wrinkle-improving effect of Example 2 using the polymeric carbodiimide was more excellent.

Wrinkle improvement effect
(n = 20, 5 point scale) Comparative Example 1 Example 1 Example 2 Wrinkle improvement effect 2.2 3.5 3.7

Formulation example : Wrinkle improvement Cosmetic  Produce

According to the conventional cosmetic preparation method, cosmetic compositions for improving wrinkles were prepared with the components and contents shown in Table 3 below.

Component (% by weight) toilet water Lotion cream pack Retinyl acetate 1.0 1.0 1.0 1.0 Benzene, 1,3, -bis (1-isocyanato-1-methylethyl) -, homopolymers, polyethylene glycol mono-ether- 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 - Cetearyl glucoside - - 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 The buffer (pH 4.5) Balance Balance Balance Balance Sum 100 100 100 100

Claims (9)

Carbodiimide compounds; And a cosmetic composition for prevention and improvement of wrinkles comprising a wrinkle preventing and improving component.
The method according to claim 1,
Wherein the wrinkle preventing and improving component comprises a carboxyl group or an amine group in the molecule.
The method according to claim 1,
The wrinkle preventing and improving ingredient may be at least one selected from the group consisting of vitamin A (retinoid), vitamin E (tocopherol), flavonoid, polyphenol, superoxide dismutase (SOD), coenzyme Q10, alpha-lipoic acid, acetylhexapeptide, retinol, retinyl palmitate, (EGF), kinetin, snail mucilage, aquanomide, ceramide, glycerin, hyaluronic acid, betaine, chitosan, urea and derivatives thereof, and the like. Wherein the cosmetic composition is at least one selected from the group consisting of:
The method according to claim 1,
Wherein the wrinkle preventing and improving component has a functional group capable of being covalently bonded to protein residues on the skin surface.
5. The method of claim 4,
The functional group covalently bonded to the protein is selected from imide ester, aryl azide, diazyline, hydroxymethylphosphine, pentafluorophenyl ester, pyridyl disulfide, sulfo-hydroxy succinimide ester, alkoxyamine, hydrazide, The present invention relates to a process for the preparation of a compound of formula (I) wherein R 1 is selected from the group consisting of haloacetyl, azide, carbonate, aldehyde, propionaldehyde, butylaldehyde, nitrophenylcarbonate, aziridine, isocyanate, thiocyanate, epoxide, At least one selected from the group consisting of oxycarbonylamidazole, imine, thiol, maleimide, vinylsulfone, ethyleneimine, thioether, acrylonitrile, acrylic acid or methacrylic acid ester, disulfide and ketone Composition.
The method according to claim 1,
Wherein the carbodiimide compound is 0.001 to 10 parts by weight based on 100 parts by weight of the total composition.
The method according to claim 1,
A carbodiimide compound and a wrinkle preventing and improving ingredient are formulated into a single preparation in an encapsulated form; A composition for prevention and improvement of wrinkles, which is formulated into two separate forms of carbodiimide compound and wrinkle prevention and improvement component, respectively.
The wrinkle preventing and improving component may further comprise at least one member selected from the group consisting of carbodiimide, imidoesters, aryl azides, diazirines, hydroxymethylphosphines, pentafluorophenyl esters, pyridyl disulfides, sulfo-hydroxysuccinimide esters, alkoxy amines, A functional group covalently bonded to at least one protein selected from the group consisting of tyrosine, tyrosine, tyrosine, tyrosine, tyrosine, tyrosine, tyrosine, tyrosine, tyrosine, tyrosine,
9. A cosmetic composition for prevention and improvement of wrinkles comprising the wrinkle preventing and improving component according to claim 8.