KR20150066806A - Cosmetics Compositions for atopic dermatitis or skin trouble care - Google Patents

Abstract

The present invention relates to a composition for preventing and improving atopic dermatitis or skin troubles. According to the present invention, the composition for preventing and improving atopic dermatitis or skin troubles contains a responsive atopic dermatitis or skin trouble care material and/or a carbodiimide-based compound, which introduces a specific functional group enabling a covalent bond with protein residues of the surface of skin, to form a covalent bond without damage to skin, thereby providing semipermanent effect for preventing and improving atopic dermatitis or skin troubles.

Description

TECHNICAL FIELD The present invention relates to a cosmetic composition for atopic dermatitis or skin trouble,

The present invention relates to a reactive atopic or skin trouble-care substance to which a functional group binding to a protein is bound, and a composition for preventing and improving atopic or skin trouble.

In general, atopic or skin trouble care refers to the ability to reduce or prevent skin troubles caused by environmental factors, immunological reactions, etc., or to protect the skin from the external environment, and particularly to atopic and various allergies, acne, And the like in order to restore the skin to health from a variety of skin troubles such as skin, hair, and the like.

It is also defined that quasi-drugs do not have the purpose of use, such as affecting the structure and function of the body, rather than being used for the treatment or prevention of diseases, even though they have an effect on the human body.

Atopy or skin trouble-care agent generally includes atopic and skin trouble-care agents for preparing and protecting the skin, bases, points, make-up atopy and skin trouble-care agents and body atopic and skin trouble- Some of my products are also included.

However, when used as a raw material and a pharmaceutical ingredient for such atopic or skin trouble-care functional ingredients, it provides only a temporary effect until the next cleansing after the treatment, but there is always the hassle of reprocessing after cleansing.

Patent Document 1 relates to a non-aqueous personal care product for skin. In the non-aqueous part, a functional group capable of covalently bonding with protein residues on the surface of skin is provided with a carbonate, an aldehyde, a propionaldehyde, a butylaldehyde ), Nitrophenyl carbonate, aziridine, isocyanate, thiocyanate, epoxide, tresylate, succinimide, hydroxy, and the like. But are not limited to, hydroxysuccinimidyl ester, imidazole, oxycarbonylamidazole, imine, thiol, maleimide, vinylsulfone, ethyleneimine, ), Thioether, acrylonitrile, acrylic acid or methacrylic ester, disulfide, At least one selected from the group consisting of ketones and functional groups represented by RX (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) Discloses a personal care product for skin characterized in that it is separated into a non-aqueous part and a water-based part including a conditioning component having a hydrophilic property and a conditioning component having a hydrophilic property and is mixed immediately before use. However, Since the content of amino acids in the skin constituting the skin is targeted and reacted with lysine containing a small amount of skin keratin (3.1 to 6.9%), 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 composition for preventing or ameliorating atopic or skin troubles, which is capable of continuously providing a semi-permanent atopic or skin trouble-care effect without damaging the skin.

As a means for solving the above problems, the present invention provides a composition for prevention and improvement of atopic or skin trouble comprising a carbodiimide compound and atopic or skin troublescure substance.

As another means for solving the above-mentioned problems, the present invention provides a method for treating atopy or a skin trouble-care substance, which comprises administering to an atopic or skin troublescale substance an imido ester, an aryl azide, a diazirine, a hydroxymethylphosphine, a pentafluorophenyl ester, a pyridyl disulfide, Wherein the functional group is covalently bonded to at least one protein of the skin surface selected from the group consisting of a hydroxy group, a hydroxy group, a hydroxy group, a hydroxy group, a hydroxy group, a hydroxy group, a hydroxy group,

As another means for solving the above-mentioned problems, the present invention provides a composition for prevention and improvement of atopic or skin trouble comprising the reactive atopic or skin troublescure substance.

The composition for prevention and improvement of atopic or skin troubles according to the present invention contains a reactive atopy or a skin trouble-care substance and / or a carbodiimide compound into which specific functional groups capable of covalently bonding with protein residues of the skin are incorporated, It forms a covalent bond and provides semi-permanent prevention and improvement of atopic or skin troubles.

The present invention relates to a composition for prevention and improvement of atopy or skin trouble comprising a carbodiimide compound and an atopic or skin trouble-care substance.

The composition for preventing or ameliorating atopic or skin troubles according to the present invention can be prepared, for example, by reacting a carbodiimide compound with a known atopic or skin trouble care substance to form a reactive atopic or skin trouble care substance having a carbodiimide group bonded thereto By forming covalent bonds with proteins in the skin, it is possible to maximize atopic and skin troubles and improvement effects.

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 the effect of improving the atopy or the skin trouble is not continuously exhibited. On the other hand, if the content exceeds 10 parts by weight, the carbodiimide- And reacts with an efficacious substance in a state in which it is not reacted with, thereby failing to improve persistence and acting as a lost ingredient.

In the present invention, 'skin trouble' means, for example, secondary troubles such as allergies, dermatitis, abnormal keratinization, itching and inflammation caused thereby.

The atopic or skin trouble-care substance used in the present invention is at least as effective as atopic or skin troubles due to functions such as skin relaxation and regeneration and immunity enhancement such as drugs derived from natural materials such as plants, plants and minerals, fermented extracts, Or at least have the ability to prevent, reduce, or prevent skin irritation. For example, there may be mentioned ceramide, peptide, hyaluronic acid, glycerin, tacrolimus, pimecrolimus, clindamycin, erythromycin, tretinoin, adrenaline, benzoyl peroxide, licorice acid, epidermal growth factor (EGF) Oil, propolis, olive leaf extract, astragalus extract, horsetail extract, arnica extract, and high ginseng tincture. The peptide may specifically be a whey peptide, a wheat hydrolyzed peptide, a keratin peptide, a keratin hydrolyzate peptide, a collagen peptide, a collagen hydrolyzate peptide, and the like, but is not limited thereto.

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 atopic or skin trouble care substance is used for 100 parts by weight of total 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 atopy or skin trouble-care substance can increase the reaction efficiency with the carbodiimide compound by including a carboxyl group or an amine group in the molecule.

In addition, in the present invention, the atopic or skin trouble-care substance 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 composition for preventing or improving atopic or skin troubles according to the present invention, atopic or skin trouble care component having a carboxyl group is made into a form of reactive ester atopic or skin trouble care component having direct bioactivity, (Ex, aspartic acid, and glutamic acid) present in an excessive amount (15.5 to 23.5%) of the amino acid residues (ex., Aspartic acid, and glutamic acid) is reactively esterified using a carbodiimide compound capable of targeting an atopic or skin trouble- The effect can be significantly increased by increasing the reaction efficiency by making the form (reactive atopy or skin trouble care ingredient). 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 an atopy or a skin trouble-care ingredient containing a functional group such as amine, hydrazide, haloacetyl, or azide in the molecule.

As a more preferred embodiment, a polymeric carbodiimide compound of formula (2) or 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide is firstly added to the surface of atopic or skin- A carbodiimide compound such as 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide.HCl is firstly reacted to form a reactive ester, an atopy having an amine in the molecule in addition to the reactive ester functional group formed, or By reacting a skin trouble-care substance or reacting with an amine on the surface of the skin, excellent atopy or skin trouble can be prevented and improved. 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, atopic or skin troublesome substance having a carboxyl group (atopic or skin trouble care component) molecules react with a carbodiimide compound in a primary reaction to form a reactive ester, followed by reaction with an amino acid of a living body having an amine residue Bond is formed.

[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 protein react first with a carbodiimide compound to form a reactive ester, followed by an atopy or a skin trouble-care substance having an amine residue ) To form a covalent bond.

[Reaction Scheme 2]

The carbodiimide compound increases the reaction efficiency of the skin protein with atopic or skin trouble-care ingredients, so that the reactive atopic or skin trouble-care ingredients bound to the skin are easily separated from the skin during shampoo, detergent, soap, etc. And can remain almost permanently attached to the skin.

The present invention also relates to the use of atopic or skin-care agents in combination with at least one compound selected from the group consisting of carbodiimide groups, imidoesters, aryl azides, diazylines, hydroxymethylphosphines, pentafluorophenyl esters, pyridyl disulfides, sulfo-hydroxysuccinimide 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 an ester, alkoxyamine, hydrazide, haloacetyl, azide, carbonate, aldehyde, propionaldehyde, butylaldehyde, nitrophenylcarbonate, aziridine, isocyanate, thiocyanate, epoxide, In the group consisting of an imidyl ester, imidazole, oxycarbonylamidazole, imine, thiol, maleimide, vinylsulfone, ethyleneimine, thioether, acrylonitrile, acrylic acid or methacrylic acid ester, disulfide and ketone A reactive atopy having a functional group covalently bonded to at least one selected protein It can include skin problems, care substances.

For example, as shown in Reaction Scheme 1, a carbodiimide group formed by a primary reaction of a carbodiimide compound may be combined with an atopic or skin trouble substance (reactive atopic or skin trouble care substance). In addition, the present invention may include a composition for preventing and improving atopic or skin troubles including the above-mentioned reactive atopic or skin trouble-care substance.

In order to further enhance the effect of the composition for prevention and improvement of atopic or skin troubles according to the present invention, fatty acids such as palmitic acid and stearic acid, fatty alcohols, long-chain alkyl quaternary When mixed with a cationic surfactant such as an ammonium salt, a cationized cellulose, a cationic guar, a cationic polymer such as cationized polyvinylpyrrolidone, silicone, etc., formulation can be facilitated. 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 composition for preventing or improving atopic or skin troubles according to the present invention can be used for the preparation of a composition for preventing or improving atopic or skin troubles including atopic or skin trouble care functional ingredients 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 composition for preventing or ameliorating atopic or skin troubles according to the present invention comprises a carbodiimide compound and at the same time contains an atopic or skin-care agent having a reactive functional group, , It is easier to maintain its activity in a non-aqueous formulation, and the reaction may be performed by mixing with a buffer for pH control immediately before use, or by contacting with water in a 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-based compound and the atopic or skin trouble-care substance can be formulated into a single agent or an encapsulated form of two or a separate form of the agent. In addition, a method of blocking a derivative having a reactive functional group and an ingredient having atopic or skin-trouble-protecting function combined with water through the encapsulation may also be used.

In order to enhance atopy or skin troubles with functional groups in compositions for preventing and improving atopic or skin troubles according to the present invention, it is possible to use 2-basic acid esters such as dioctyl succinate, dioctyl adipate, diethyl sebacate and the like And polyols, polyethylene glycol, propylene glycol, hexylene glycol, butanediol and isomers thereof, glycerol, benzyl alcohol, ethoxydiglycol and derivatives thereof. The above-mentioned solvents increase the permeability of the skin and are used as a solvent of a poorly soluble substance. More preferably, the solvent used for enhancing the activity-maintaining effect of the atopy or skin-care agent having a functional group is diethyl sebacate, ethoxy glycol, bis-ethoxy glycol cyclohexane 1,4-dicarboxylate and the like have.

Hereinafter, the present invention will be described in detail with reference to Examples and Experimental Examples. However, the following Examples and Experimental Examples are merely illustrative of the present invention, and the present invention is not limited to the following Examples and Experimental Examples.

Example  1 to 4 and Comparative Example  1-2

An aqueous solution prepared by mixing peptide, propolis, carbodiimide compound and buffer solution (pH 4.5) in distilled water was prepared and used for the test according to the composition and contents as shown in Table 1 below.

Category (% by weight) Comparative Example 1 Comparative Example 2 Example 1 Example 2 Example 3 Example 4 Distilled water 49.0 49.0 48.0 48.0 48.0 48.0 Keratin peptide 1.0 - 1.0 - 1.0 - Propolis - 1.0 - 1.0 - 1.0 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride - - 1.0 1.0 - - Benzene, 1,3, -bis (1-isocyanato-1-methylethyl) -, homopolymers, polyethylene glycol mono-ether- - - - - 1.0 1.0 The buffer (pH 4.5) 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

Experimental Example  1: Itching and dermatitis improvement

Each of the atopy-improving cosmetic compositions of Comparative Examples 1 to 2 and Examples 1 to 4 was applied to the inner part of the arm three times a day for 10 applicants having atopic diseases, and the effect was evaluated on a 5-point scale The more excellent the effect, the better the score. The results are shown in Table 2.

Effect (n = 10, 5 point scale) Comparative Example 1 Comparative Example 2 Example 1 Example 2 Example 3 Example 4 Itching improvement effect 2.8 3.0 3.5 3.6 4.2 4.1 Dermatitis improvement effect 3.0 3.2 3.6 3.4 4.3 4.0

The results of the experiments of Examples 1 to 4 and Comparative Examples 1 and 2 (Table 2) show that a derivative having a bioreactive group substitution in comparison with Comparative Examples 1 to 3, which does not contain a carbodiimide, Was evaluated as excellent in atopy improvement and persistence.

Claims (9)

Carbodiimide compounds; And a composition for preventing and improving atopy or skin trouble comprising atopic or skin troublesome substances.
The method according to claim 1,
Wherein the atopic or skin trouble-care substance comprises a carboxyl group or an amine group in the molecule, for preventing or ameliorating atopic or skin troubles.
The method according to claim 1,
The atopic or skin trouble-care substance may be at least one selected from the group consisting of ceramide, peptide, hyaluronic acid, glycerin, tacrolimus, pimecrolimus, clindamycin, erythromycin, tretinoin, adrenalin, benzoyl peroxide, licorice acid, epidermal growth factor Wherein the composition is at least one selected from the group consisting of corn oil, corn oil, macadamia seed oil, propolis, olive leaf extract, ganoderma extract, horsetail extract, arnica extract and gossyta tincture.
The method according to claim 1,
Wherein the atopic or skin trouble-care substance has a functional group capable of covalently bonding 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) as defined in claim 1, wherein the compound is selected from the group consisting of: haloacetyl, azide, carbonate, aldehyde, propionaldehyde, butylaldehyde, nitrophenylcarbonate, aziridine, isocyanate, thiocyanate, epoxide, Prevention of atopy or skin trouble selected from the group consisting of oxycarbonylamidazole, imine, thiol, maleimide, vinylsulfone, ethyleneimine, thioether, acrylonitrile, acrylic acid or methacrylic acid ester, disulfide and ketone, / RTI >
The method according to claim 1,
Wherein the carbodiimide compound is 0.001 to 10 parts by weight per 100 parts by weight of the total composition.
The method according to claim 1,
A carbodiimide-based compound and an atopic or skin trouble-improving substance are formulated into a single preparation in an encapsulated form; A carbodiimide compound and atopy or a skin trouble-clearing substance are separated from each other.
The present invention relates to the use of at least one compound selected from the group consisting of carbodiimide, imidoesters, aryl azides, diazirines, hydroxymethylphosphines, pentafluorophenyl esters, pyridyl disulfides, sulfo-hydroxysuccinimide esters, alkoxy amines, A reactive atopy or a skin trouble-care substance in which a functional group covalently bonded to at least one protein selected from the group consisting of hydrazide, haloacetyl, and azide is bound.
9. A composition for prevention and improvement of atopic or skin trouble comprising the reactive atopic or skin trouble-care substance according to claim 8.