KR102084521B1 - Compositions for prevention and improvement of acne - Google Patents

Abstract

The present invention relates to a composition for preventing and improving acne.
The composition for preventing and improving acne according to the present invention contains an acne prevention component having a specific functional group capable of covalently bonding with protein residues on the surface of the skin, thereby forming a covalent bond without damaging the skin to provide a semi-permanently desired acne improvement effect. .

Description

Compositions for prevention and improvement of acne

The present invention relates to a reactive acne prevention component and a composition for preventing and improving acne with a functional group binding to a protein.

In general, acne prevention and healing agents are used to prevent or cure follicular fatty gland inflammatory diseases that occur in areas where there are many sebaceous glands, such as facial or back, to beautify the skin of the human body, increase attractiveness, change appearance, or The purpose is to apply it to the body, spray, or other similar methods to maintain the health.

In addition, quasi-drugs are defined as having a mild action and are not used for the treatment or prevention of diseases, but do not have a purpose of use such as affecting the structure and function of the body.

Acne is a follicular fatty gland inflammatory disease that occurs in areas with a lot of sebaceous glands such as facial or back, and is likely to occur from adolescence to adolescence, and acne at this time is also called vulgar acne. In addition, there is a big difference in the occurrence of acne, depending on the person, people who are prone to occur repeatedly occurs mentally stressed. Acne is divided into several stages, depending on its clinical symptoms. First, the first symptom is white papules called comedons that match the follicle, which is a mixture of keratin and lipids in the upper part of the capillary. Inflammatory papules include inflammation as connective tissue around the maternal ducts, leukocytes, lymphocytes, and microphages, which precipitate and form pustules, and as they deteriorate, they become sintered and remain scar after treatment. Of course, acne caused by inflammation and pustules may be considered essential to dermatology, but the purpose of acne cosmetics is that skin care does not shift from pulp to purulent papules.

There are four types of skin types: oily, dry, normal skin and dry oily skin. It is known that acne and sebum correlate and correlate with fatty oil and oily skin. Acne is likely to occur especially in the spring and summer when sebum secretion is active, and acne, especially after puberty acne is deeply related to the menstrual cycle, it is known that acne occurs severely before menstruation. It is reported that deterioration of the stratum corneum function such as barrier function and pH rhythm function as one of the factors of comedon formation as the balance of hormones changes greatly before menstruation.

Representative factors of the occurrence of acne can be seen as endocrine factors, abnormal keratinization disorders of the pores, bacterial factors, etc. In addition, there are irritation (external factors) or stress (internal factors), and they are complicated to cause acne do. As a countermeasure against such acne, methods have been attempted through anti-androgen action, hyperlipidemia suppression effect, comedon formation inhibitory action, skin flora inhibition action, and free radical removal action.

Acne prevention and healing cosmetics are generally used for skin preparation, protection foundation acne prevention and healing cosmetics, bases, points, makeup acne prevention and healing cosmetics and body acne prevention and healing cosmetics products such as washing, sun care and sun tanning. It is included.

Common raw materials used to construct the acne prevention and healing cosmetics include oily materials such as fats, waxes, hydrocarbons, higher fatty acids, higher alcohols, ester oils and silicone oils, anionic, cationic, amphoteric and nonionic surfactants. It includes high molecular compounds used as moisturizers, thickeners and film-forming agents, ultraviolet absorbers and blockers, antioxidants, metal ion sequestrants, colorants including dyes and pigments, fragrances, and preservatives.

In addition, active ingredients that act on the prevention and healing of acne are estradiol, estrone, ethynyl estradiol as sebum inhibitors, sulfur, salicylic acid, resorcin, benzalkonium chloride and benzetoni chloride as disinfectants. Um, halokalban, 2,4,4-trichloro-2-hydroxyphenol and the like are used. In addition, ingredients used as disinfectants for cosmetics such as triclosan, trichlorocarbi, isopropylmethylphenol and pinion, and allantoin , anti-inflammatory agents such as ε-aminocapric acid, glycilinic acid, and the like, keratin solubilizers such as glycolic acid and the like can be used.

However, when used on the skin with such an acne prevention and healing ingredient or composition, it provides only a temporary effect until the next cleaning after the treatment, there is always a hassle to reprocess after cleaning.

Patent document 1 relates to a skin non-aqueous personal care product, and is a functional group that can be covalently bonded to protein residues on the skin surface in a non-aqueous part, such as carbonate, aldehyde, propionaldehyde, and butylaldehyde. ), 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 component 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 reaction efficiency is increased by targeting lysine containing a small amount of skin keratin (3.1 to 6.9%) or cysteine of skin keratin (2.3 to 3.8%). There is a problem that it is degraded and must synthesize each material separately.

Korean Unexamined Patent No. 2008-0064467

An object of the present invention is to provide a composition for preventing and improving acne that can continuously give a semi-permanent acne prevention effect without damaging the skin.

As a means for solving the above problems, the present invention provides a composition for preventing and improving acne comprising a carbodiimide compound and an acne prevention component.

As another means for solving the above problems, the present invention is an acne prevention component, carbodiimide, imido ester, aryl azide, diazirine, hydroxymethyl phosphine, pentafluorophenyl ester, pyridyl disulfide, sulfo- Provided is a reactive acne prevention 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 composition for preventing and improving acne comprising the reactive acne prevention component.

The composition for preventing and improving acne according to the present invention contains a reactive acne prevention component and / or a carbodiimide-based compound incorporating a specific functional group capable of covalently bonding with protein residues of the skin, thereby forming a covalent bond without damaging the skin. It provides semi-permanent anti-acne effect.

The present invention relates to a composition for preventing and improving acne comprising a carbodiimide compound and an acne prevention component.

The composition for preventing and improving acne according to the present invention, for example, reacts a carbodiimide-based compound with a known acne prevention component to form a covalent bond with a protein of the skin through a reactive acne prevention component having a carbodiimide group bonded thereto. By maximizing the prevention of acne.

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 total composition. If its content is less than 0.001 parts by weight, there is a problem that it is difficult to show continuous acne improvement effect, and if it exceeds 10 parts by weight, the carbodiimide-based compound that is excessively present beyond the reaction site present on the skin is not effective in the reaction with the skin. By reacting with the substance there is a problem that can act as a component that does not help to improve the sustainability.

In the present invention, the 'acne prevention effect' refers to a function of preventing or healing the follicular fatty gland inflammatory disease occurring in areas where a lot of sebaceous glands such as facial or back are present, to beautify the skin of the human body.

The anti-acne ingredient used in the present invention may include an anti-acne ingredient that can improve the damaged part by melanin pigmentation of the skin, such as extracts derived from natural products such as copper, plants, minerals, amino acids, hormones, vitamins, and the like. However, the present invention is not limited thereto. For example, sebum inhibitors include estradiol, estrone, ethynylestradiol; Sulfur, salicylic acid, resorcin as keratin exfoliating and dissolving agents; Fungicides such as benzalkonium chloride, benzetonium chloride, harockalban, 2,4,4-trichloro-2-hydroxyphenol; As the disinfectant of cosmetics, triclosan, trichlorocarbitol, isopropylmethylphenol, pinion; Anti-inflammatory agents such as allantoin, ε-aminocapric acid, glycilic acid, etc. as keratin solubilizers; It may be at least one selected from the group consisting of keratin solubilizers such as glycolic acid.

The anti-acne component is preferably used from 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 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 anti-acne component in the present invention can increase the reaction efficiency with the carbodiimide compound by including a carboxyl group or an amine group in the molecule.

In addition, the anti-acne component in the present invention may have a functional group capable of covalently bonded to the protein residues on the skin surface.

The functional group covalently bonded with the protein is carbodiimide, imido ester, aryl azide, diazirine, hydroxymethyl phosphine, pentafluorophenyl ester, pyridyl disulfide, sulfo-hydroxysuccinimide ester, alkoxy amine, Hydrazide, haloacetyl, azide, carbonate, aldehyde, propionaldehyde, butylaldehyde, nitrophenyl carbonate, aziridine, isocyanate, thiocyanate, epoxide, tresylate, succinimide, hydroxysuccinimidyl ester , Imidazole, oxycarbonyl 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 reactive moieties of thiol, hydroxyl, carboxyl or amine.

The carbodiimide-based compound generically refers to a compound including 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 excessively large, and the reaction sites capable of reacting are excessively large, and The molecule | numerator which has a bodyimide group becomes so huge 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).

[Formula 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.

[Formula 3]

In a preferred embodiment of the composition for preventing and improving acne according to the present invention, the anti-acne component having a carboxyl group is made in the form of a reactive ester acne prevention component having direct bioreactivity or excessively present in skin keratin (15.5-23.5%). Reactive esterification of amino acids (ex, aspartic acid, glutamic acid) to produce reactive ester forms (reactive acne prevention components) using carbodiimide-based compounds that can be targeted by anti-acne components including amine groups By increasing, 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 an anti-acne component containing a functional group such as amine, hydrazide, haloacetyl, azide in the molecule.

In a more preferred embodiment, the polymer form carbodiimide-based compound of formula (2) or 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide is first applied to the acne prevention component molecule having a carboxyl group or the protein surface of the skin. Carbodiimide-based compounds such as (1-ethyl-3- (3-dimethylaminopropyl) carbodiimide.HCl) are first reacted to form reactive esters, and the reactive ester functional groups formed to react acne prevention having amines in the molecule again. Or by reacting with an amine on the skin surface, an excellent acne prevention 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 the scheme 1, the anti-acne component molecule having a carboxyl group (denoted as acne in the scheme 1) first reacts with a carbodiimide 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. The reaction schematic to form is shown.

Scheme 1

Aspartic acid and glutamic acid, which are biological amino acids having a carboxyl group on the protein surface of the skin, are reacted first with a carbodiimide compound to form a reactive ester, followed by an acne prevention component having an amine residue (represented as acne in Scheme 21 below). ) Shows a reaction schematic to form a covalent bond.

Scheme 2

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

The present invention also provides a carbodiimide group, imido ester, aryl azide, diazirine, hydroxymethyl phosphine, pentafluorophenylester, pyridyl disulfide, sulfo-hydroxysuccinimide ester, alkoxy, etc. 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 Contains reactive anti-acne ingredients combined with covalent functional groups Can.

For example, as shown in Scheme 1, the carbodiimide-based compound may include an acne prevention component having a carbodiimide group bonded thereto. In addition, the present invention may include a composition for preventing and improving acne comprising the reactive acne prevention component.

In the acne prevention and amelioration composition according to the present invention, fatty acids such as palmitic acid and stearic acid, fatty alcohols, long-chain alkyl quaternary ammonium salts such as straight and branched chains, etc. Formulation may be facilitated when used in combination with a cationic polymer such as a cationic surfactant, cationic cellulose, cationic guar, or cationic polyvinylpyrrolidone, or silicone. 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 composition for preventing and improving acne according to the present invention may be used for the preparation of a composition for preventing and improving acne, including an ingredient of an acne preventing function having a functional group. Examples of application of skin products generally include skin care, basic cosmetics (cosmetics, serums, essences, lotions, creams, etc.), color cosmetics (makeup bases, foundations, powders, eye shadows, lip gloss, lipsticks, lip balms, 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 be included.

More preferably, the composition for preventing and improving acne according to the present invention includes a carbodiimide-based compound and at the same time includes an acne-preventing component having a reactive functional group, and when the above agent is deteriorated in water, the non-aqueous formulation It is easier to maintain the activity in the reaction system, and the reaction may be caused by mixing with a buffer for pH control immediately before use or contacting with water during the cleaning process. Examples of non-aqueous formulations include liquid, sheet, powder, tablet, tablets, oils, waxes, ampoules, gels, and the like used as conventional non-aqueous cosmetic preparations. In addition, the carbodiimide-based compound and the anti-acne component may be formulated in a single agent in encapsulated form or in two separate forms, respectively. In addition, a method of blocking derivatives in a form in which a reactive functional group and a component having an acne preventing function are combined with water through encapsulation may also be used.

In order to increase the acne prevention effect having a functional group in the composition for preventing and improving acne according to the present invention, 2-basic acid ester oil such as dioctyl succinate, dioctyl adipate, diethyl sebacate, 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 acne-preventing 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 merely to illustrate the invention, but the content of the present invention is not limited to the following examples.

Example  1 to 4 and Comparative example  1 to 2

The compositions and contents of Examples 1 to 4 and Comparative Examples 1 and 2 were prepared using the compositions and contents shown in Table 1 below, and the prepared compositions were applied to the acne area for 20 subjects and left for 30 minutes. After inducing the reaction and rinsing with the first flowing water, the process of drying was repeated three days twice a day in the morning and in the afternoon, and after 5 days, a five-point scale (5 very good, 4 slightly good, 3 No difference, 2 no effects, 1 very no effect) confirmed acne prevention and healing effects.

division
(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 Glycilic Acid 1.0 - 1.0 - 1.0 - Glycolic acid - 1.0 - 1.0 - 1.0 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide. Hydrochloric acid - - 1.0 1.0 - - Benzene, 1,3, -bis (1-isocyanato-1-methylethyl)-, homopolymer, polyethylene glycol mono-meth-ether-block - - - - 1.0 1.0 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 results of Examples 1 to 4 and Comparative Examples 1 and 2 (Table 2), compared to Comparative Examples 1 and 2, in which the bioreactive group does not contain a carbodiimide as an anti-acne component, was carried out including carbodiimide Examples 1 to 4 showed better acne prevention and persistence due to the covalent bond formation effect of carbodiimide, and Examples 3 and 4 using polymer carbodiimide showed the best acne prevention and acne sustaining effect. It was.

Acne Improvements (n = 10) Comparative Example 1 Comparative Example 2 Example 1 Example 2 Example 3 Example 4 Satisfaction after 5 days
(5-point scale) 2.8 3.0 3.7 3.8 4.0 3.9

Formulation example : Acne Improvement Cosmetic  Produce

According to the conventional cosmetic preparation method, acne-improving cosmetics were prepared with the ingredients and contents shown in Table 3 below.

Ingredient (% by weight) toilet water Lotion cream pack Glycilic Acid 0.5 0.5 0.5 0.5 Glycolic acid 0.5 0.5 0.5 0.5 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 - - Carboxy Vinyl Polymer 0.1 0.1 0.1 - Polyvinyl alcohol - - - 15.0 Fiji-12 nonylphenyl ether 0.3 - - 0.5 Polysorbate 80 0.5 - - - Polysorbate 60 - 1.5 1.5 1.5 Sorbitassquioleate - 1.5 - - Sorbitan stearate - - 0.5 - Liquid paraffin - 0.5 10.0 - Caprylic / Capric Triglycerides - 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 - - Beeswax - 5.0 - - antiseptic Quantity Quantity Quantity Quantity Spices Quantity Quantity Quantity Quantity Buffer (pH 4.5) Remaining amount Remaining amount Remaining amount Remaining amount Sum 100.0 100.0 100.0 100.0

Claims (9)

Carbodiimide-based compounds represented by Formula 2; And acne prevention and composition comprising an anti-acne component:
[Formula 2]

In Formula 2, n is 1 to 100, m is 1 to 100.
The method of claim 1,
The acne prevention component is a composition for preventing and improving acne comprising a carboxyl group or an amine group in the molecule.
The method of claim 1,
The anti-acne component is estradiol, estrone, ethynyl estradiol, sulfur, salicylic acid, resorcin, benzalkonium chloride, benzetonium chloride, harocban, 2,4,4-trichloro-2-hydroxyphenol, Triclosan, trichlorocarbitol, isopropylmethylphenol, pinion, allantoin, ε-aminocapric acid, glycylic acid and glycolic acid composition for preventing and improving at least one selected from the group consisting of.
The method of claim 1,
The acne prevention component is a composition for preventing and improving acne having a functional group capable of covalently bonding with a protein residue on the skin surface.
The method of claim 4, wherein
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, Oxycarbonyl amidazole, imine, thiol, maleimide, vinylsulfone, ethyleneimine, thioether, acrylonitrile, acrylic or methacrylic acid esters, disulfide and ketones composition for acne prevention and improvement .
The method of claim 1,
Carbodiimide compound is 0.001 to 10 parts by weight based on 100 parts by weight of the total composition for preventing and improving acne.
The method of claim 1,
Carbodiimide-based compounds and anti-acne ingredients are formulated in a single agent in encapsulated form; A composition for preventing and improving acne, wherein the carbodiimide-based compound and the anti-acne component are formulated in two separate forms.
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