KR102640681B1 - Eutectic mixture comprising salicylic acid - Google Patents

Abstract

The present invention relates to a eutectic mixture containing an alkylamidoamine of the following formula (1) and salicylic acid, a cleaning composition containing the same, and a method for producing the same,
When salicylic acid and an alkylamidoamine of Formula 1 are included in the form of a eutectic mixture, it can be stable and hypoallergenic, and can increase the skin adsorption rate of salicylic acid to provide an appropriate cleansing composition for improving acne.
[Formula 1]

Description

Eutectic mixture comprising salicylic acid}

The present invention relates to a eutectic mixture containing salicylic acid, a cleaning composition containing the same, and a method for producing the same.

One of the important functions of the skin is to protect the human body from various external stimuli, and various organs are gathered accordingly. Among these, the sebaceous glands that secrete sebum help maintain skin homeostasis by secreting sebum that suppresses antibacterial and moisture evaporation through pores. However, it is known that in the process of secreting sebum through pores, pores become enlarged and sebum can lead to acne.

Acne is a chronic inflammatory disease of the sebaceous gland unit and occurs mainly in adolescents, but is also known to be observed in adults. In general, acne occurs frequently on the face, neck, chest, and back where sebaceous glands are concentrated, and is characterized by skin changes such as comedones that harden as sebum accumulates in the hair follicles, papules in the form of raised skin less than 1 cm in size, pus blisters, and nodules. It is known that it extends beyond the affected area and leaves a scar. Acne is usually caused by a combination of various factors, and representative causes include increased sebum secretion, hyperkeratinization, proliferation of Propionibacterium acnes, and inflammatory reactions. In addition, genetic or inflammatory reactions are known. It is known to be caused by environmental factors.

Such acne is treated by controlling sebum secretion, managing dead skin cells, removing causative bacteria using antibacterial ingredients, and suppressing inflammatory reactions. Representative examples include using face washes with antibacterial effects and increasing the acidity of the skin. In addition, treatment using salicylic acid is known, which can improve acne by promoting skin turnover and suppressing inflammatory reactions.

Meanwhile, salicylic acid is a type of strong acid, which is irritating to the skin due to its acidity and has the problem of destabilizing the formulation of the skin improvement composition due to its high crystallinity. In addition, when the active ingredient is included in a cleansing product, a large amount of salicylic acid applied to the skin is removed during the washing process with water, resulting in a problem that very little of the active ingredient remains on the skin.

Accordingly, there is a need for the development of a skin improvement composition that contains salicylic acid, which is effective in improving acne, but is also mild to the skin, has a stable formulation, and allows a large amount to remain on the skin during the cleansing process.

The present invention is intended to solve the above problems, and aims to provide a composition that increases the adsorption rate and skin permeability of salicylic acid to the skin and is not irritating to the skin.

Additionally, the present invention seeks to provide a composition for treating and improving acne, including salicylic acid.

The present inventors completed the present invention by confirming that when salicylic acid and alkylamidoamine are used together to form a eutectic mixture, the crystallinity of salicylic acid is lowered and that this eutectic mixture increases the adsorption rate of salicylic acid on the skin.

Accordingly, the present invention provides a eutectic mixture containing an alkylamidoamine of the following formula (1) and salicylic acid.

[Formula 1]

In Formula 1,

R ₁ is hydrogen or a linear or branched hydrocarbon group having 1 to 50 carbon atoms, and is substituted or unsubstituted with one or more substituents selected from the group consisting of a hydroxy group, an amine group, a thiol group, and a halogen group,

R ₂ is a direct bond or a linear or branched divalent hydrocarbon group having 1 to 5 carbon atoms,

R ₃ is each independently hydrogen or a linear or branched hydrocarbon group having 1 to 5 carbon atoms.

Additionally, the present invention provides a cleaning composition containing the above eutectic mixture.

In addition, the present invention includes the steps of mixing salicylic acid and an alkylamidoamine of the following formula (1) to prepare a eutectic mixture; It provides a method for producing a eutectic mixture comprising.

In the present invention, by including salicylic acid and an alkylamidoamine of Formula 1 in the form of a eutectic mixture, the crystallinity of salicylic acid can be lowered and a stable eutectic mixture can be obtained. In addition, this eutectic mixture contains salicylic acid, which is effective in improving acne, while exhibiting hypoallergenicity by lowering acidity, and can exhibit a high skin turnover effect, skin adsorption rate, and permeability without salicylic acid being released by water during washing.

Figure 1 shows general microscope and polarizing microscope images of Example 2 according to Experimental Example 1 of the present invention.
Figure 2 shows general microscope and polarizing microscope images of Comparative Example 1 according to Experimental Example 1 of the present invention.
Figure 3 shows images confirmed with the naked eye of Comparative Examples 1, 2, and Example 6 of the present invention.
Figure 4 is a graph showing the average daily peeling rate for each formulation according to Experimental Example 5 of the present invention.
Figure 5 is an image confirming the turnover promotion effect for each formulation according to Experimental Example 5 of the present invention.

Hereinafter, the present invention will be described in detail.

Since the present invention is subject to various changes and can take various forms, specific embodiments will be illustrated and described in detail below. However, this is not intended to limit the present invention to a specific disclosed form, and should be understood to include all changes, equivalents, and substitutes included in the spirit and technical scope of the present invention.

The present invention provides a eutectic mixture containing an alkylamidoamine of the following formula (1) and salicylic acid.

[Formula 1]

In Formula 1,

R ₁ is hydrogen or a linear or branched hydrocarbon group having 1 to 50 carbon atoms, and is substituted or unsubstituted with one or more substituents selected from the group consisting of a hydroxy group, an amine group, a thiol group, and a halogen group,

R ₂ is a direct bond or a linear or branched divalent hydrocarbon group having 1 to 5 carbon atoms,

R ₃ is each independently hydrogen or a linear or branched hydrocarbon group having 1 to 5 carbon atoms.

When salicylic acid, which is solid and has crystalline particles at room temperature, is mixed with alkylamidoamine and heated, a eutectic mixture can be formed. The eutectic mixture formed in this way can provide a liquid formulation that does not solidify even when the temperature is lowered to room temperature.

In the present invention, "eutectic mixture" refers to a mixture of two or more solid or liquid substances, where two components with high melting points are mixed to form polar intermolecular dipole-dipole attraction, dipole-induced dipole attraction, intermolecular hydrogen bonding or anti-polarization. The two components form a complex through Derwaals interaction. The complex formed as above has a lower melting point than the component with the lowest melting point among each component by interfering with the ability of each component to crystallize, that is, to return to the solid state, and thus can exhibit a liquid state at room temperature. .

In the alkylamidoamine of Formula 1, the “hydrocarbon group” is a substituent consisting of carbon and hydrogen and may be a saturated hydrocarbon group or an unsaturated hydrocarbon group containing one or more double or triple bonds.

In Formula 1, R ₁ may be a linear or branched hydrocarbon group having 3 to 45 carbon atoms, and may be substituted or unsubstituted with a hydroxy group.

In Formula 1, R ₂ may be a linear divalent hydrocarbon group having 1 to 4 carbon atoms, and preferably may be ethylene or propylene.

In Formula 1, R ₃ is hydrogen or a linear or branched hydrocarbon group having 1 to 5 carbon atoms, and may be the same or different from each other. Preferably, R ₃ may be the same as each other.

In one specific embodiment of the present invention, in Formula 1, R ₂ is ethylene or propylene, and R ₃ may be a linear or branched hydrocarbon group having 1 to 5 carbon atoms.

The alkylamidoamine of Formula 1 is Abyssinian/Meadowfoamamidopropyl Dimethylamine, Almondamidopropyl Dimethylamine, Avocadamidopropyl Dimethylamine, and Babasuami. Babassuamidopropyl Dimethylamine, Behenamidopropyl Dimethylamine, Brassicamidopropyl Dimethylamine, Cannabisamidopropyl Dimethylamine, Cocamidopropyl Dimethylamine ( Cocamidopropyl Dimethylamine, Dibehenamidopropyl Dimethylamine, Dilinoleamidopropyl Dimethylamine, Isostearamidopropyl Dimethylamine, Lauramidopropyl Dimethylamine ), Linoleamidopropyl Dimethylamine, Minkamidopropyl Dimethylamine, Myristamidopropyl Dimethylamine, Oatamidopropyl Dimethylamine, Oleamido Oleamidopropyl Dimethylamine, Olivamidopropyl Dimethylamine, Palmitamidopropyl Dimethylamine, Pentaclethramidopropyl Dimethylamine, Polyhydroxystearamidopropyl Dimethylamine ( Polyhydroxystearamidopropyl Dimethylamine, Ricinoleamidopropyl Dimethylamine, Sesamidopropyl Dimethylamine, Shea Butteramidopropyl Dimethylamine, Soyamidopropyl Dimethylamine, Stear Amidopropyl Dimethylamine, Sunflowerseedamidopropyl Dimethylamine, Tallamidopropyl Dimethylamine, Tallowamidopropyl Dimethylamine, Wheat Germamidopropyl Dimethylamine (Wheat Germamidopropyl Dimethylamine), Behenamidoethyl Diethylamine, Palmitamidopropyl Diethylamine, and Stearamidoethyl Diethylamine. It could be more than that.

Specifically, the alkylamidoamine of Formula 1 is myristamidopropyl dimethylamine, stearamidopropyl dimethylamine, behenamidopropyl dimethylamine, brassicamidopropyl dimethylamine, and oleamidopropyl. Dimethylamine (Oleamidopropyl Dimethylamine), Isostearamidopropyl Dimethylamine, Palmitamidopropyl Dimethylamine, Sunflowerseedamidopropyl Dimethylamine, Wheat Germamidopropyl Dimethylamine In the group consisting of Germamidopropyl Dimethylamine, Behenamidoethyl Diethylamine, Palmitamidopropyl Diethylamine, Stearamidoethyl Diethylamine and Cocamidopropyl Dimethylamine There may be one or more types selected.

More preferably, the alkylamidoamine of Formula 1 is one selected from the group consisting of myristamidopropyl dimethylamine, stearamidopropyl dimethylamine, behenamidopropyl dimethylamine, and cocamidopropyl dimethylamine. It could be more than that.

In one embodiment of the present invention, the molar ratio of the alkylamidoamine of Formula 1 and salicylic acid may be 15:85 to 60:40. Preferably, the molar ratio may be 18:82 to 60:40, 15:85 to 50:50, 20:80 to 50:50, 20:80 to 45:55, or 25:75 to 40:60. If the molar ratio of alkyl amidoamine and salicylic acid is less than 15:85, salicylic acid may precipitate when cooled after melting and mixing when preparing the eutectic mixture, and if it exceeds 60:40, alkyl amidoamine may be precipitated when preparing the eutectic mixture. It may precipitate.

The present invention can also provide a cleaning composition containing a eutectic mixture according to the present invention.

In one embodiment of the present invention, the eutectic mixture may be included in an amount of 0.0001 to 20% by weight based on the total weight of the composition. Specifically, it may be included at 0.2 to 20% by weight, 0.2 to 15% by weight, 1 to 10% by weight, or 2 to 8% by weight.

In one embodiment of the present invention, the alkylamidoamine of Formula 1 may be included in an amount of 0.00005 to 10% by weight based on the total weight of the composition. Specifically, it may be 0.001 to 8% by weight, 1 to 6% by weight, or 1 to 4% by weight.

In one embodiment of the present invention, the salicylic acid may be included in an amount of 0.00005 to 5% by weight based on the total weight of the composition. Specifically, it may be 0.01 to 5% by weight, 0.1 to 4% by weight, or 1 to 3% by weight.

The composition of the present invention may further include one or more of wax and oil. Waxes and oils can increase the adsorption rate of salicylic acid onto the skin by lowering surface energy and increasing spreadability. Wax and oil may be added during heating and mixing in the preparation of the composition, and the order of addition is not limited.

In one embodiment of the present invention, the wax may be a wax that is solid at room temperature and has a melting point of 40°C or higher, but is not limited thereto.

In one embodiment of the present invention, the wax may be a mixed material of two or more components, and due to the lower crystallinity of this mixed material compared to a single material, separation between materials occurs when mixed with a eutectic mixture at high temperature and then cooled to room temperature. You can prevent this from happening.

In one embodiment of the present invention, the surface energy of the wax is 15 to 80 mJ/m ² , preferably 17 to 75 mJ/m ² , which is a similar value to skin having a surface energy of 38 to 57 mJ/m ² . Typically, it may be 20 to 70 mJ/m ² .

The surface energy can be measured using the contact angle of water and can be defined by the following equation.

[Equation 1]

In one embodiment of the present invention, the wax may be an ester wax, an alcohol wax, a carboxylic acid wax, or a wax containing one or more structures such as a linear alkyl group in the molecule.

Specifically, the waxes include white fir leaf wax (Abies Alba Leaf Wax), mimosa acacia flower wax (Acacia Dealbata Flower Wax), green wattle flower wax (Acacia Decurrens Flower Wax), green wattle/jojoba/sunflower seed wax polyglyceryl -3 Esters (Acacia Decurrens/Jojoba/Sunflower Seed Wax Polyglyceryl-3 Esters), Sweet Acacia Flower Wax (Acacia Farnesiana Flower Wax), Beeswax, Beeswax Acid, Beeswax Polyglyceryl-3 Esters, Beeswax Behenyl Beeswax, Behenyl/Isostearyl Beeswax, Bis-Hydroxyethoxypropyl Dimethicone Beeswax Esters, Bis-PEG-12 Dimethicone Beeswax , Butyloctyl Beeswax, C14-30 Alkyl Beeswax, C18-38 Alkyl Beeswax, C30-50 Alkyl Beeswax ), Camellia Japonica Leaf Wax, Camellia Sinensis Leaf Wax, Cananga Odorata Flower Wax, Candelilla Wax Esters, Candelilla Wax Hydrocarbon Wax Hydrocarbons, Carnauba Acid Wax, Carnauba Acid Wax Butylene Glycol Esters, Carnauba Acid Wax Glycol Esters, Caster Isostearate Beads Castor Isostearate Beeswax Succinate, Cistus Ladaniferus Flower Wax, Citrus Aurantium Amara (Bitter Orange) Flower Wax, Citrus Aurantium Dulcis (Orange) Flower Wax , Orange Peel Wax (Citrus Aurantium Dulcis (Orange) Peel Wax), Lemon Peel Wax (Citrus Limon (Lemon) Peel Wax), Carnauba Wax (Copernicia Cerifera (Carnauba) Wax), Carnauba Wax Extract (Copernicia Cerifera (Carnauba) Wax Extract, Cytisus Scoparius Flower Wax, Cocamide MEA, Dimethicone PEG-8 Beeswax, Dimethiconol Beeswax ), Eclipta Prostrata Wax, Ericerus Pela Wax, Euphorbia Cerifera (Candelilla) Wax, Euphorbia Cerifera (Candelilla) Wax Extract, sunflower seed wax (Helianthus Annuus (Sunflower) Seed Wax), Helichrysum Angustifolium Wax, Hexanediol Beeswax, Hexanetriol Beeswax, Hydrolyzed Beeswax, Hydrolyzed Candelilla Wax, Hydrolyzed Carnauba Wax, Hydrolyzed Sunflower Seed Wax, Iris Florentina Flower Wax, Spain Jasminum Grandiflorum (Jasmine) Flower Wax, Common Jasmine Officinale (Jasmine) Flower Wax, Arabian Jasmine Sambac (Jasmine) Flower Wax, Jojoba Oil/Wax Polyglyceryl-3 Esters (Jojoba Oil/Wax Polyglyceryl-3 Esters), Jojoba Wax PEG-80 Esters, Jojoba Wax PEG-120 Esters, Lanolin Wax , Lavender Flower Wax (Laandula Angustifolia (Laender) Flower Wax), Henna Wax (Lawsonia Inermis (Henna) Wax), Liriodendron Tulipifera Leaf Wax, Microcrystalline Wax, Mink Wax ), Montan Acid Wax, Montan Wax, Myrica Cerifera (Bayberry) Fruit Wax, Myrica Pubescens Fruit Wax, rouge daffodil flower Narcissus Poeticus Flower Wax, Nelumbo Nucifera Flower Wax, Nutmeg Kernel Oil/Flower Wax Glycerides, Octyldodecyl Beeswax, Ormenis Water Ormenis Multicaulis Flower Wax, Oryza Sativa (Rice) Bran Wax, Ouricury Wax, Oxidized Beeswax, Oxidized Microcrystals Oxidized Microcrystalline Wax, Oxidized Rice Bran Wax, Palm Kernel Wax, PEG-6 Beeswax, PEG-8 Beeswax ( PEG-8 Beeswax, PEG-12 Beeswax, PEG-20 Beeswax, PEG-75 Lanolin Wax, Scented Geranium Wax (Pelargonium Graveolens Wax), Avocado Wax (Persea Gratissima (Aocado) Wax), Mastic Leaf Wax (Pistacia Lentiscus (Mastic) Leaf Wax), Tuberose Flower Wax (Polianthes Tuberosa Flower Wax), Polyglyceryl-3 Beeswax ( Polyglyceryl-3 Beeswax), Potassium Oxidized Microcrystalline Wax, PPG-5 Lanolin Wax, PPG-5 Lanolin Wax Glyceride, Propolis Wax, Prunus Armeniaca (Apricot) Kernel Wax, Pyrus Cydonia Peel/Fruit Wax, Pyrus Malus (Apple) Peel Wax, Rhus Succedanea Fruit Wax, Rhus Verniciflua Peel Wax, Ribes Nigrum (Black Currant) Bud Wax, Rice Bran Wax Ethyl Esters, Rosa Centifolia Flower Wax, Rosa Damascena Flower Wax, Rosa Hybrid Flower Wax, Rosa Multiflora Flower Wax, Rosemary Flower Wax ( Rosmarinus Officinalis (Rosemary) Flower Wax), Rubus Idaeus (Raspberry) Leaf Wax, Saccharum Officinarum (Sugarcane) Wax, Salicylyl Beeswax, Clary flower/leaf/stem wax (Salvia Sclarea (Clary) Flower/Leaf/Stem Wax), Black Elderberry Wax (Sambucus Nigra Wax), Shellac Wax, Jojoba Seed Wax (Simmondsia Chinensis (Jojoba) Seed Wax), Sodium Beeswax , Sorbeth-2 Beeswax, Sorbeth-6 Beeswax, Sorbeth-8 Beeswax, Sorbeth-20 Beeswax Beeswax, Spent Grain Wax, Stearyl Beeswax, Stipa Tenacissima Wax, Sunflower Seed Wax Alkanes, Synthetic Beeswax , Synthetic Candelilla Wax, Synthetic Japan Wax, Synthetic Wax, Sorbitan Oleate, Cetearyl Olivate, Sorbitan Olivate ( Sorbitan Olivate, Sorbitan Palmate, Sorbitan Palmitate, Sorbitan Sesquicaprylate, Sorbitan Sesquiisostearate, Sorbitan Sesquioli Sorbitan Sesquioleate, Sorbitan Sesquistearate, Sorbitan Stearate, TDI Oxidized Microcrystalline Wax, Fragrant Violet Petal Wax (iola Odorata) Leaf Wax), Vitis vinifera (Grape) Leaf Wax, Hydrogenated Adansonia Digitata Seed Oil, Hydrogenated Apricot Kernel Oil, Hydrogenated Argan Kernel Oil (Hydrogenated Argania Spinosa Kernel Oil), Hydrogenated Avocado Oil, Hydrogenated Black Currant Seed Oil, Hydrogenated Calophyllum Inophyllum Seed Oil, Hydro Hydrogenated Camelina Sativa Seed Oil, Hydrogenated Camellia Japonica Seed Oil, Hydrogenated Camellia Oleifera Seed Oil, Hydrogenated Canola Oil (Hydrogenated Canola Oil), Hydrogenated Castor Oil, Hydrogenated Coconut Acid, Hydrogenated Coconut Oil, Hydrogenated Corn Oil, Hydrogenated Cottonseed Oil, Hydrogenated Crambe Abyssinica Seed Oil, Hydrogenated Cranberry Seed Oil, Hydrogenated C12-18 Triglyceride Rise (Hydrogenated C12-18 Triglycerides), Hydrogenated Didecene, Hydrogenated Didodecene, Hydrogenated Egg Oil, Hydrogenated Evening Primrose Oil Primrose Oil, Hydrogenated Fish Oil, Hydrogenated Grapefruit Seed Oil, Hydrogenated Grapeseed Oil, Hydrogenated Hazelnut Oil, Hydrogenated Hemp Seed Oil, Hydrogenated Jojoba Oil, Hydrogenated Kukui Nut Oil, Hydrogenated Lime Seed Oil, Hydro Hydrogenated Macadamia Seed Oil, Hydrogenated Meadowfoam Seed Oil, Hydrogenated Menhaden Oil, Hydrogenated Microcrystalline Wax , Hydrogenated Milk Lipids, Hydrogenated Mineral Oil, Hydrogenated Mink Oil, Hydrogenated Moringa Oleifera Seed Oil, Hydro Hydrogenated Nepeta Cataria Oil, Hydrogenated Oat Kernel Oil, Hydrogenated Olive Oil, Hydrogenated Orange Roughy Oil, Hydrogenay Hydrogenated Orange Seed Oil, Hydrogenated Ostrich Oil, Hydrogenated Palm Kernel Oil, Hydrogenated Palm Oil, Hydrogenated Red Ginseng Oil (Hydrogenated Panax Ginseng Root Oil), Hydrogenated Passiflora Edulis Seed Oil, Hydrogenated Peach Kernel Oil, Hydrogenated Peanut Oil, Hydrogenay Hydrogenated Phosphatidylcholine, Hydrogenated Pinus Pinaster Seed Oil, Hydrogenated Pistachio Seed Oil, Hydrogenated Pistacia Vera Seed Oil, Hydro Hydrogenated Plukenetia Volubilis Seed Oil, Hydrogenated Polybutene, Hydrogenated Prunus Domestica Seed Oil, Hydrogenated Pumpkin Seed Oil , Hydrogenated Punica Granatum Seed Oil, Hydrogenated Rapeseed Oil, Hydrogenated Raspberry Seed Oil, Hydrogenated Rhus Verniciflua Peel Wax ), Hydrogenated Rice Bran Oil, Hydrogenated Rice Bran Wax, Hydrogenated Rosa Canina Fruit Oil, Hydrogenated Rosin, Hydrogenated Safflower Seed Oil, Hydrogenated Sesame Seed Oil, Hydrogenated Shark Liver Oil, Hydrogenated Shea Butter, Hydrogenated Shea Oil, Hydrogenated Soybean Oil, Hydrogenated Sunflower Seed Oil, Hydrogenated Sweet Almond Oil, Hydrogenay Hydrogenated Torreya Nucifera Seed Oil, Hydrogenated Vegetable Oil, Hydrogenated Walnut Seed Oil, and Hydrogenated Wheat Germ Oil One or more types selected from the group consisting of may be used.

More specifically, the wax includes Bees Wax, Carnauba Wax, Cocamide MEA, Cetearyl Olivate, Sorbitan Olivate, and Rice Bran. Rice Bran Wax, Hydrogenated Castor Oil, Hydrogenated Coconut Oil, Microcrystalline Wax, and Hydrogenated Jojoba Oil. It may include one or more types selected from the group consisting of

In one embodiment of the present invention, the wax may be included in an amount of 30 to 200 parts by weight based on 100 parts by weight of the eutectic mixture. Preferably, it may be included in an amount of 40 to 180 parts by weight, more preferably 50 to 160 parts by weight, based on 100 parts by weight of the eutectic mixture. When the wax is included in the above range, the skin absorption rate of salicylic acid in the eutectic mixture can be further improved and can be homogeneously mixed with the eutectic mixture.

On the other hand, like wax, separation of substances may not occur even if oil is mixed with a eutectic mixture at high temperature and then cooled to room temperature, and the spreadability of the formulation can be increased to increase the adsorption rate of salicylic acid on the skin.

In one embodiment of the present invention, the oil is a hydrocarbon-based oil with a linear or non-linear structure such as pentane, hexane, cyclohexane, heptane, octane, isododecane, or dodecane, ethyl ether, butyl ether, or methyl-t -Ether-based oils containing ether groups such as butyl ether, ester-based oils containing ester groups such as ethyl acetate, butyl acetate, or ethyl butyrate, ketone-based oils such as methyl ethyl ketone, benzene, toluene, or xylene. It may include one or more types selected from the group consisting of aromatic oils, haloalkane oils such as dichloromethane, dichloroethane, chloroform, or carbon tetrachloride, and silicone oils such as dimethicone or cyclomethicone.

More specifically, the oil consists of cetyl ethylhexanoate, caprylic/capric triglyceride, isopropyl myristate, mineral oil, isononyl isononanoate, isostearyl isostearate, squalane and dodecane. It may include one or more types selected from the group.

In one embodiment of the present invention, the oil may be included in an amount of 30 to 200 parts by weight based on 100 parts by weight of the eutectic mixture. Preferably, it may be included in an amount of 40 to 180 parts by weight, more preferably 50 to 160 parts by weight, based on 100 parts by weight of the eutectic mixture. When the oil is included in the above range, the skin absorption rate of salicylic acid in the eutectic mixture can be further improved and can be homogeneously mixed with the eutectic mixture.

The cleaning composition of the present invention may further include a moisturizer, water, oxidizing agent, preservative, thickener, viscosity modifier, ultraviolet absorber, pH adjuster, fragrance, dye, conditioning agent, etc., but are usually mixed in the cleaning composition. There are no restrictions as long as it is an ingredient that can be used.

The cleaning composition of the present invention can be used for cleaning the scalp, face, body, hands and feet, etc. for cleaning the human body, and the area of use is not particularly limited.

The composition of the present invention can be applied to various formulations such as cream, liquid, emulsion, gel, or oil. The composition of the present invention may be contained in products for cleaning the face, skin, or hair, such as cosmetic soap, body wash, face wash, hand wash, bath salt, liquid cleanser, cleansing oil, shampoo, rinse, or conditioner. , but is not limited to this.

The present invention also provides a composition for promoting skin turnover comprising the eutectic mixture according to the present invention.

Additionally, the present invention provides a method for producing the above eutectic mixture.

The production method according to the present invention includes mixing salicylic acid and an alkylamidoamine of Formula 1 to prepare a eutectic mixture.

In the above manufacturing method,

The eutectic mixture may be prepared through the steps of mixing salicylic acid and the alkylamidoamine of Formula 1 at room temperature, heating the mixture, and cooling the mixture.

In the present invention, “room temperature” is room temperature without artificially applying heat or lowering the temperature, and may vary depending on the season and/or region, but may generally mean a temperature range of 15 to 40°C, or 20 to 35°C. there is.

The stirring speed for each step may be different. For example, the room temperature mixing step may be mixing at room temperature at low speed, specifically at a stirring speed of 5 rpm to 100 rpm, preferably 10 rpm to 80 rpm, and more preferably 25 rpm to 70 rpm.

The step of heating the mixture may be performed at 25 to 100°C for 30 minutes to 10 hours, preferably at 30 to 95°C for 40 minutes to 8 hours, more preferably at 40 to 90°C for 50 minutes to 4 hours. It can be done over time. Alternatively, the step of heating the mixture may be heating the mixture to a temperature that is 5 to 20°C higher than the melting point of the alkylamidoamine of Chemical Formula 1. This heating step can liquefy the mixture or change it into a viscous gel-like preparation.

The stirring speed in the heating step may be 100 rpm to 800 rpm, preferably 200 rpm to 700 rpm, and more preferably 300 rpm to 600 rpm.

After the heating step, a cooling step may be performed. The cooling step may be a step of cooling to room temperature and is performed to lower the temperature of the heated mixture. At this time, low-speed stirring may be performed to facilitate the degassing process. Here, the stirring speed may be 5 rpm to 100 rpm, preferably 10 rpm to 80 rpm, and more preferably 25 rpm to 70 rpm.

The present invention also provides the step of preparing the eutectic mixture; and preparing a cleaning composition containing a eutectic mixture. A method for producing a cleaning composition comprising a.

Preparing the cleaning composition may include mixing with ingredients to prepare the cleaning formulation. The above ingredients are not limited as long as they are ingredients commonly added to cleaning formulations.

In the step of preparing the cleansing composition, the eutectic mixture may be added to the cleansing formulation. The cleansing formulation is not limited as long as it contains commonly known cleaning ingredients. Additionally, the eutectic mixture may be added to the cleansing formulation and stirred at a stirring speed of 200 to 800 rpm, preferably 400 to 800 rpm, for 5 minutes to 1 hour, preferably 5 minutes to 30 minutes.

When the cleaning composition includes one or more of wax and oil, the cleaning composition can be prepared by preparing a eutectic mixture and then adding one or more of wax and oil. In addition, the steps of mixing alkylamidoamine and salicylic acid, cooling, and preparing the cleaning composition can be applied in the same manner as previously described.

In the above production method, the contents of the alkylamidoamine of Formula 1, salicylic acid, eutectic mixture, wax, oil, and cleaning composition can be applied as described above.

Hereinafter, the present invention will be described in detail through the following experimental examples. However, the following experimental examples are merely illustrative of the present invention, and the content of the present invention is not limited by the following experimental examples. Additionally, since these experimental examples are only for the purpose of aiding understanding of the present invention, the scope of the present invention is not limited by them in any way.

Example

Experimental Example 1. Determination of crystal formation of alkyl amidoamine and salicylic acid

Eutectic mixtures were prepared with various alkylamidoamines and salicylic acid as follows, frozen at -24°C, stored at room temperature (F/T), and stored at 25°C and 50°C for 1 day and then stored for more than 2 hours. The formation of crystals was confirmed by exposure to room temperature. The formation of crystals was checked visually and using a polarizing microscope to determine whether fine crystal particles were formed, and the results are shown in Table 1 and Figures 1 and 2.

<Preparation of Comparative Examples 1 and 2>

Salicylic acid and the corresponding mixed raw materials according to Table 1 were mixed in the corresponding mole % in a container, and then heated to about 10 ° C higher than the melting point (MP) of the mixed raw materials and waited until melted. The molten mixture was stirred at about 400 RPM for 15 minutes using an overhead stirrer (IKA) and then cooled to room temperature.

<Preparation of Comparative Example 3>

Salicylic acid and caprylic/capric triglyceride were mixed in a container at the mole percentage according to Table 1, and then the mixed raw materials were heated at about 70°C. Afterwards, it was stirred for 15 minutes at about 400 RPM using an overhead stirrer (IKA), and then cooled to room temperature.

<Preparation of Examples 1 to 4>

Salicylic acid and alkyl amidoamine according to Table 1 were mixed in a container in mole percentage according to Table 1, and then heated to about 10°C higher than the melting point (MP) of the mixed raw materials and waited until melted. The molten mixture was stirred at about 400 RPM for 15 minutes using an overhead stirrer (IKA) and then cooled to room temperature.

Raw material name Comparative Example 1 Comparative example 2 Comparative Example 3 Example 1 Example 2 Example 3 Example 4 beeswax 37.5 - - - - - - rice bran wax - 37.5 - - - - - Caprylic/Capric Triglyceride - - 37.5 - - - - Myristamidopropyl dimethylamine - - - 37.5 - - - Stearamidopropyl dimethylamine - - - - 37.5 - - Behenamidopropyl dimethylamine - - - - - 37.5 - Cocamidopropyl dimethylamine - - - - - - 37.5 salicylic acid 62.5 62.5 62.5 62.5 62.5 62.5 62.5 Total (mole%) 100 100 100 100 100 100 100 Salicylic acid recrystallization or not O O O X X X X

As shown in Table 1 and Figures 1 and 2, in Comparative Examples 1 to 3, crystallization of salicylic acid progressed during cooling after heating and mixing, but in Examples 1 to 4, crystallization of salicylic acid did not proceed during cooling after heating and mixing. It showed stability under all temperature conditions.

Experimental Example 2. Determination of crystal formation according to the molar ratio of alkylamidoamine and salicylic acid

As in Examples 5 to 8 below, eutectic mixtures were prepared by varying the mixing ratios of alkyl amidoamine and salicylic acid, frozen at -24°C and then stored at room temperature (F/T), 25°C, and 50°C. After storing at °C for 1 day, crystal formation was checked by exposing to room temperature for more than 2 hours. The formation of crystals was confirmed by visual inspection and the formation of fine crystal particles using a polarizing microscope.

<Production of Examples 5 to 8>

Salicylic acid and stearamidopropyl dimethylamine were mixed in a container at mole percentages according to Table 2, then heated to about 10°C higher than the melting point of stearamidopropyl dimethylamine and waited until melted. Once melted, it was mixed using an overhead stirrer (IKA) at about 400 RPM for 15 minutes and then cooled to room temperature to prepare the mixtures of Examples 5 to 8.

Raw material name Example 5 Example 6 Example 7 Example 8 Stearamidopropyl dimethylamine 15 20 40 50 salicylic acid 85 80 60 50 Total (mole%) 100 100 100 100 Salicylic acid recrystallization or not △ X X X

As a result of the experiment, it was confirmed that in Example 5, the crystallization of salicylic acid progressed slightly immediately after preparing the eutectic mixture, and in the case of Example 8, although it did not recrystallize, it was solidified without showing the room temperature liquid phase characteristics that are characteristic of the eutectic mixture. On the other hand, Examples 6 and 7 showed stability under various conditions, similar to Example 4.

Meanwhile, Figure 3 shows images confirming with the naked eye whether crystallization of Comparative Examples 1 and 2 prepared in Experimental Example 1 and Example 6 prepared in Experimental Example 2 were shown. In Comparative Examples 1 and 2 of FIG. 3, it can be confirmed that crystallization of salicylic acid proceeds during heating and mixing followed by cooling during the manufacturing process. However, in Example 6, it can be confirmed that crystallization of salicylic acid does not proceed even after heating and mixing and cooling. .

Experimental Example 3. Evaluation of salicylic acid adsorption depending on whether it is a eutectic mixture or not

In this experiment, in order to evaluate whether the adsorption amount of salicylic acid increases or decreases in the case of a eutectic mixture of salicylic acid and alkylamidoamine, each formulation was applied to the surface of pig skin, washed, and the skin permeability of the remaining salicylic acid was measured to evaluate the effect. did.

<Preparation of Comparative Example 4 and Examples 9 to 12>

The eutectic mixtures of Examples 1 to 4 and the cleansing foam formulation prepared above were placed in a mixing container and mixed at room temperature at 600 RPM using an overhead stirrer for about 30 minutes to prepare the cleansing compositions of Examples 9 to 12.

For Comparative Example 4, a cleansing composition containing 2% by weight of salicylic acid was prepared in the same manner as above, and the compositions of the compositions of Comparative Example 4 and Examples 9 to 12 prepared accordingly are shown in Table 3 below.

<Confirmation of salicylic acid permeation amount in Comparative Example 4 and Examples 9 to 12>

Sterilized pig skin (thickness: 1.7~2.0mm, ² I put it in.

The evaluation method was to apply 20 μL of water on the pig skin to simulate wet skin, and then apply 40 μL of the cleansing formulation of Comparative Example 4 and Examples 9 to 12 (Bellman Microbiome Capsule Cleansing Foam from LG Household & Health Care Co., Ltd.). . Afterwards, it was rolled 30 times with a polyethylene stick for 30 seconds and kept at room temperature for 30 seconds. Afterwards, the surface was washed with water at a flow rate of approximately 1 L/min for 30 seconds, and then placed in a constant temperature and humidity chamber at 37.5°C and 50% relative humidity for 30 minutes to proceed with permeation. Afterwards, the content of salicylic acid remaining in the pig skin and receptor chamber was measured. Here, the concentration of salicylic acid was obtained by measuring the fluorescence spectrum (Ex: 300 nm, measurement range: 340 ~ 510 nm), and the concentration was calculated after creating a calibration curve using the fluorescence intensity measured at 400 nm, and calculating the concentration and extraction solvent. The permeation amount of salicylic acid was measured using volume.

Raw material name Comparative Example 4 Example 9 Example 10 Example 11 Example 12 Myristamidopropyl dimethylamine - 1.7 - - - Stearamidopropyl dimethylamine - - 2 - - Behenamidopropyl dimethylamine - - - 2.31 - Cocamidopropyl dimethylamine - - - - 1.54 salicylic acid 2 2 2 2 2 Cleansing foam formulation 98 96.3 96 95.69 96.46 Total (mass%) 100 100 100 100 100 Skin penetration amount of salicylic acid (μg) 2.6 4.9 5.4 6.2 4.7

As shown in Table 3, the cleansing compositions of Examples 9 to 12 containing a eutectic mixture of salicylic acid and alkylamidoamine allowed salicylic acid to permeate at least 1.8 to 2.38 times more than Comparative Example 4 containing only salicylic acid after washing. It was confirmed that it was possible.

Experimental Example 4. Evaluation of salicylic acid adsorption amount according to addition of wax and oil

In this experiment, to evaluate whether the adsorption amount of salicylic acid increases or decreases when one or more types of wax or oil is added to the eutectic mixture of salicylic acid and alkylamidoamine, each formulation is applied to the surface of pig skin and the remaining salicylic acid is washed. The effect was evaluated by measuring skin permeability.

<Preparation of Examples 13 to 18>

Salicylic acid and stearamidopropyl dimethylamine were mixed at 2% by mass each in a container, then heated to about 80-90°C and waited until melted. The molten mixture was mixed using an overhead stirrer (IKA) at about 400 RPM for 15 minutes, and then one or more types of wax and oil according to the composition in Table 4 above were added at 95°C. After mixing for 15 minutes at about 600 RPM, it was cooled to room temperature.

<Preparation of cleansing foam formulations of Examples 13 to 18>

6.67% by weight of each example formulation prepared in <Preparation of Examples 13 to 18> was added to 93.33% by weight of the cleansing foam formulation and mixed at room temperature at 600 RPM using an overhead stirrer for about 30 minutes.

<Evaluation of skin permeability>

Skin adsorption amount was measured using a Franz Cell. The Franz cell used was Labfine's FCDV-15, sterilized pig skin (thickness: 1.7~2.0mm, ² and Ethanol 1:1 mixed solution was added.

The evaluation method was to apply 20 μL of water on the pig skin to simulate wet skin, and then apply 40 μL of the cleansing foam formulation of Examples 13 to 18 (LG Household & Health Care's Bellman Microbiome Capsule Cleansing Foam). . Afterwards, it was rolled 30 times with a polyethylene stick for 30 seconds and kept at room temperature for 30 seconds. Afterwards, the surface was washed with water at a flow rate of approximately 1 L/min for 30 seconds, and then placed in a constant temperature and humidity chamber at 37.5°C and 50% relative humidity for 30 minutes to proceed with permeation. Afterwards, the content of salicylic acid remaining in the pig skin and receptor chamber was measured. The concentration of salicylic acid was determined through Fluorescence Spectrum measurement (Ex: 300 nm, measurement range: 340 ~ 510 nm), and the concentration was calculated after creating a calibration curve using the fluorescence intensity measured at 400 nm, and the concentration and volume of extraction solvent were calculated. The permeation amount of salicylic acid was measured using this method. The results are shown in Table 4.

M.P. Example 13 Example 14 Example 15 Example 16 Example 17 Example 18 beeswax 62~64℃ 2.67 - - - - - rice bran wax 79~85℃ - 2.67 - - - - Hydrogenated Castor Oil 84~89℃ - - 2.67 - - - Hydrogenated Olive Oil 54~72℃ - - - 2.67 - - cetearyl olivate 65~75℃ - - - - 2.67 0.80 Stearamidopropyl dimethylamine 69~70℃ 2.00 2.00 2.00 2.00 2.00 2.00 salicylic acid - 2.00 2.00 2.00 2.00 2.00 2.00 Sorbitan Olivate 65~75℃ - - - - - 0.53 Caprylic/Capric Triglyceride - - - - - - 1.33 Cleansing foam formulation - 93.33 93.33 93.33 93.33 93.33 93.33 Total (mass%) - 100 100 100 100 100 100 Skin permeability (μg) - 14.9 7.9 6 16.4 15.4 24.9

As a result of the evaluation, the permeability of salicylic acid in Examples 13 to 17 in which wax was added increased by about 1.11 to 3.08 times compared to Example 10 in which wax was not added. In addition, in Example 18, in which oil was added to wax, the permeability of salicylic acid increased by about 4.7 times compared to Example 10, and Example 18, in which both wax and oil were added, had a higher permeability than Examples 13 to 17 in which only wax was added. It was also confirmed that the was higher.

Experimental Example 5. Confirmation of turnover promotion effect

The turnover promotion effect was evaluated under actual use conditions using Example 10 containing a eutectic mixture of salicylic acid and alkylamidoamine and Example 18 containing this eutectic mixture and wax and oil. As a comparison group, Comparative Example 4, which was a non-coated formulation and a formulation containing 2% by weight of salicylic acid, was used.

Each formulation was applied to the henna-stained area (circular area with a diameter of 2 cm) during a shower, and the change in brightness was measured twice a week using a colorimeter (5 participants, evaluated over 3 weeks). At this time, the L value evaluated at each time point was calculated as the daily average peeling rate using the following equation.

[Equation 2]

L _max : L value immediately after coloring, L _d : L value by date, L ₀ : Initial L value

The evaluation results are shown in Figures 4 and 5, and it was confirmed that the turnover promotion effect of Example 10, which is a formulation containing a eutectic mixture, was higher than that of Comparative Example 4 even under actual use conditions, and that the formulation containing both wax and oil in the eutectic mixture was confirmed. Example 18 was the highest.

Claims (10)

A eutectic mixture containing an alkylamidoamine of the following formula (1) and salicylic acid.
[Formula 1]

In Formula 1,
R ₁ is hydrogen or a linear or branched hydrocarbon group having 1 to 50 carbon atoms, and is substituted or unsubstituted with one or more substituents selected from the group consisting of a hydroxy group, an amine group, a thiol group, and a halogen group,
R ₂ is a direct bond or a linear or branched divalent hydrocarbon group having 1 to 5 carbon atoms,
R ₃ is each independently hydrogen or a linear or branched hydrocarbon group having 1 to 5 carbon atoms. According to claim 1,
In Formula 1, R ₂ is ethylene or propylene, and R ₃ is a linear or branched hydrocarbon group having 1 to 5 carbon atoms. According to claim 1,
The alkylamidoamine of Formula 1 includes myristamidopropyl dimethylamine, stearamidopropyl dimethylamine, behenamidopropyl dimethylamine, brassicamidopropyl dimethylamine, and oleamidopropyl dimethylamine ( Oleamidopropyl Dimethylamine, Isostearamidopropyl Dimethylamine, Palmitamidopropyl Dimethylamine, Sunflowerseedamidopropyl Dimethylamine, Wheat Germamidopropyl Dimethylamine , 1 selected from the group consisting of Behenamidoethyl Diethylamine, Palmitamidopropyl Diethylamine, Stearamidoethyl Diethylamine, and Cocamidopropyl Dimethylamine. Eutectic mixture of more than one species. According to claim 1,
A eutectic mixture in which the alkylamidoamine of Formula 1 and salicylic acid have a molar ratio of 15:85 to 60:40. A cleaning composition comprising the eutectic mixture of claim 1. According to clause 5,
A cleaning composition containing the eutectic mixture in an amount of 0.0001 to 20% by weight based on the total weight of the composition. According to claim 5,
The cleaning composition further includes one or more of wax and oil. A composition for promoting skin turnover comprising the eutectic mixture of claim 1. Preparing a eutectic mixture by mixing salicylic acid and an alkylamidoamine of the following formula (1); Method for producing a eutectic mixture comprising.
[Formula 1]

In Formula 1,
R ₁ is hydrogen or a linear or branched hydrocarbon group having 1 to 50 carbon atoms, and is substituted or unsubstituted with one or more substituents selected from the group consisting of a hydroxy group, an amine group, a thiol group, and a halogen group,
R ₂ is a direct bond or a linear or branched divalent hydrocarbon group having 1 to 5 carbon atoms,
R ₃ is each independently hydrogen or a linear or branched hydrocarbon group having 1 to 5 carbon atoms. According to clause 9,
A method of producing a eutectic mixture comprising mixing salicylic acid and an alkylamidoamine of Formula 1 at room temperature, heating the mixture, and cooling the mixture.