Oleosome formulation composition having excellent stability and antibacterial properties containing a branched diol-based compound as an active ingredient and a method for producing the same

Abstract

The present invention relates to an oleosome preparation composition having excellent stability and antibacterial properties containing a branched diol-based compound as an active ingredient and a method for producing the same. More specifically, by treating oleosomes with a mixture of a branched diol-based compound, a linear diol-based compound, a glyceryl ether / ester compound, and other preservatives, it has excellent dosage form stability, exhibits very excellent antibacterial activity against bacteria, molds, yeasts, etc., and has an anti-corrosion boosting effect.

Description

Technical Field

[0001] The present invention relates to an oleosome formulation composition having excellent stability and antibacterial properties containing a branched diol-based compound as an active ingredient, and a method for producing the same. More specifically, the present invention relates to an oleosome formulation composition having excellent dosage form stability and microbial contamination prevention effect, and a method for producing the same.

Background Art

[0002] An oleosome is a special structure in plant seeds and is a structure that stores energy in the form of oil of a natural material having a function of transmitting fragrance and functional substances to the skin without irritation. Oleosomes can be used as emulsifiers for various cosmetics, can produce cold-pressed emulsions at low production costs, and have the ability to protect and release functional substances by a natural transmission method.

[0003] Triacylglycerol molecules in plant seeds are insoluble in an aqueous environment and tend to aggregate as oil droplets. However, in order to store these water-insoluble triacylglycerols, plants have unique seed oil storage compartments with a diameter of about 1 to 10 μm, known as oil bodies, oleosomes, adiposomes, and spherosomes (collectively referred to as oleosomes) in plant seed cells (Huang, Ann. Rev. Plant Mol. Biol. 43: 177-200, 1992).

[0004] When separating vegetable oil by a process involving the use of typical organic solvents, the oleosome structure is destroyed, and wet milling and a three-phase centrifuge must be used to obtain oleosomes in their original form (Guth (Guth) PCT / US2009 / 002243).

[0005] However, biological agents such as bacteria, fungi, and mycoplasma are likely to decompose oleosomes when exposed to oleosome formulations. To protect oleosomes from exposure to biological agents, preservatives can be added. As preservatives, acid salts such as benzoates, salicylates, sorbates, propionates, or acids such as dehydroacetic acid and ferulic acid are mainly used.

[0006] To act as preservatives, acid or acid salt preservatives must exist substantially in their acid form, i.e., at a pH below 6.0, preferably between pH 4.0 and 5.0. However, in such an acidic pH range of 4.0 - 5.0, the oleosome structure is weakened, oil leaks from the oleosomes, and the oleosome formulation loses its physical stability, which poses a problem in manufacturing a final formulation consisting of intact oleosomes by mixing the components. Also, pH 4.0 - 5.0 is the isoelectric point range of oleosomes, and oleosome formulations are unstable (Qi et al. 2017). Lowering the pH to a more acidic pH outside the isoelectric point stabilizes the oleosome formulation, but it is irritating to the skin for use as a cosmetic.

[0007] Oleosomes are most stable in the neutral and alkaline pH ranges, with no oil leakage occurring. In particular, a neutral pH range is optimal for the formulation to be stable and non - irritating to the skin. However, in the neutral pH range, microbial growth is likely to occur, and microbial contamination reduces the stability of oleosome formulations. Therefore, it is necessary to find additives to effectively maintain the stability of oleosome formulations in the neutral pH range.

[0008] Generally, when a linear polyol compound, a glyceryl compound, and other preservatives, which are substances used in cosmetic compositions used in a neutral pH range, are treated with oleosomes, a phenomenon occurs in which the oleosome preparation becomes unstable and its physical properties are impaired. When the present inventor was examining substances that can stably hold an oleosome preparation, it was confirmed that a branched polyol compound does not damage the oleosome preparation, and furthermore, it has the possibility of maintaining excellent oleosome stability even when used together with other compounds that destabilize the oleosome preparation. Based on this, the inventors have worked on the development of a composition that can effectively maintain the stability of an oleosome preparation in a neutral pH range and further has the effect of preventing microbial contamination that damages the oleosome preparation.

[0009] Moreover, oleosomes are structures present in most plant seeds, and have the advantage that the supply of raw materials and the acquisition of oleosome preparations are easy. The plant seeds may be safflower seeds (Carthamus tinctorious seed), hemp seeds (Cannabis Sativa Seed), sunflower seeds (Helianthus annuus seed), coconuts (Cocos nucifera), torreya seeds (Torreya nucifera seed), camellia seeds (Camellia japonica seed), tea seeds (Camellia sinensis seed), chia seeds (Salvia Hispanica Seed), pomegranate seeds (Punica Granatum Seed), moringa seeds (Moringa Oleifera Seed), oil tea seeds (Camellia oleifera seed), rapeseed (Brassica napus seed), yuzu seeds (Citrus junos seed), olives (Olea europaea), grape seeds (Vitis vinifera seed), soybeans (Glycine max), rose hips (Rosa canina), macadamia nuts (Macadamia), meadowfoam seeds (Limnanthes Alba seed), borage (Borago officinalis), cottonseed (Gossypium hirstutum), rice bran (Oryza Sativa seed), apricot seeds (Prunus armeniaca seed), corn (Zea mays), horse chestnut fruits (Aesculus hippocastanum fruit), palm (Elaeis Guineensis), palm kernels (Elaeis Guineensis Kernel), castor beans (Ricinus communis), hazelnuts (Corylus heterophylla), jojoba (Simmondsia chinensis), avocados (Persea americana), walnut seeds (Juglans regia seed), peanuts (Arachis Hypogaea), argan (Argania Spinosa), etc.

[0010] On the one hand, safflower (Carthamus tinctorious L.) is an annual herb belonging to the Asteraceae family. Its original place is the acid mountainous area of Afghanistan or Ethiopia, and it is cultivated in China, Tibet, etc. The medicinal parts of safflower are flowers and seeds, which can inhibit platelet coagulation, delay bleeding time, and also have the effect of reducing plasma cholesterol and triglycerides. In particular, safflower seed oil contains a large amount of unsaturated fatty acids such as linolenic acid and tocopherol, and is used as a new material for antioxidation, antithrombosis and antihypertensive effects. Therefore, roasted safflower seeds are squeezed for oil and used as edible oil.

[0011] On the other hand, sunflower seeds, which are the seeds of sunflower (Helianthus annuus), contain about 50% oil. The oil contains linolenic acid, phospholipid, beta-sitosterol, glycolipid, ceramide, etc. The sugars contained in the sunflower seeds range from monosaccharides to trisaccharides, and contain organic acids such as citric acid and tartaric acid and beta-carotene. The proteins that make up sunflower seeds are rich in essential amino acids, especially arginine. Phospholipid, beta-sitosterol, glycolipid, and ceramide are lipid membrane components of the stratum corneum that prevent water loss and maintain it at an appropriate level, form a skin barrier, have excellent moisturizing effects, and have a skin softening effect.

[0012] On the one hand, hemp seed oil is an oil obtained by cold pressing from the hemp plant. It contains essential fatty acids, vitamins A, D, and E, minerals, omega-3, and omega-6, and is the only oil that supplies omega-3 and omega-6 except for fish oil. It contains more essential fatty acids than any other vegetable oil and contains the natural antioxidant vitamin E and sterols that prevent cholesterol absorption. In addition, hemp seed oil is rich in alpha-linolenic acid (ALA) and gamma-linolenic acid, plays an excellent role in moisturizing and softening the skin, and is also rich in minerals such as phosphorus, potassium, magnesium, sulfur, calcium, iron, and zinc. Such hemp seed oil can also lower cholesterol levels, treat vascular inflammation, clean the blood, and reduce hypertension, heart disease, and strokes. In particular, when used on the skin, it is excellent in moisturizing, preventing skin aging, and skin regeneration effects, and is known to relieve itching when used on atopic skin.

[0013] On the other hand, Brassica Napus L. is a biennial herb belonging to the Brassicaceae family of dicotyledonous plants, mainly cultivated around the island regions in southern Korea and Jeju Island. It was cultivated for ornamental purposes, but in recent years, it has become a major oil crop cultivated for the production of edible oil and biodiesel. Rapeseed contains 35-45% oil and is widely used in cosmetics for skin moisturization, biofuels, etc. in addition to edible oil due to its high content of oleic acid, a typical unsaturated fatty acid.

[0014] On the one hand, Camellia japonica is an evergreen tall tree native to southern Korea, Japan, and China. It mainly grows in mountainous areas, coastal areas, and near villages, and is distributed south of the central part of Korea. Camellia oil is a fatty oil obtained by drying and pulverizing the seeds of Camellia japonica L. of the Theaceae family and its congeners, and then extracting them by pressing or solvent extraction. It contains more than 80% oleic acid in the total fatty acid composition. Oleic acid is the main component of fatty acids contained in olive oil and other oils, and is an omega-9 unsaturated fatty acid.

[0015] Camellia oil does not contain any cholesterol and contains vitamin E, omega-6, omega-9, phenolic compounds such as tyrosol and hydroxytyrosol, and glycosides such as oleuropein and ligstroside, and has excellent antioxidant activity. Camellia oil is used in creams, emulsions, etc. for similar uses as olive oil, has an excellent conditioning effect, and is particularly widely used in hair products. In addition, it has no sense of rejection to the skin, has good water absorption, has a very excellent moisturizing effect, is effective for atopic treatment, does not easily deteriorate, and penetrates well into the skin, so it is very excellent as a massage base oil. It also has the effect of suppressing the oxidation of sebum and is widely used in aging skin and dry skin.

[0016] On the one hand, yuzu (Citrus Junos) was spread from China to Korea. The seeds and peel of yuzu contain bitter limonene and limonoids. Limonene in the essential oil components exhibits blood pressure lowering, antioxidant, and antibacterial effects. Limonoids can be expected to have anti-cancer effects, and phenolic and flavonoid substances have antioxidant efficacy. Therefore, it is used as a folk remedy for detoxification, cough suppression, colds, etc. Yuzu seeds are rich in natural fragrance and essential oils, and the pulp contains amino acids, free sugars, organic acids, etc. Despite containing beneficial essential oil components, yuzu seeds have not been actively utilized until now. Yuzu seeds are generated at over 1,800 tons per year, and it is necessary to expand their scope of utilization in various ways.

Summary of the Invention

Problems to be Solved by the Invention

[0017] An object of the present invention is to provide a method for manufacturing an oleosome preparation excellent in dosage form stability and microbial contamination prevention effect, and an oleosome preparation manufactured therefrom.

Means for Solving the Problems

[0018] To achieve the above object, the present invention provides a method for manufacturing an oleosome preparation composition having excellent stability and antibacterial properties, comprising: 1) a step of manufacturing an oleosome; 2) a step of treating the oleosome with a mixture of a C1-C5 branched diol-based compound; a C1-C 10 linear diol-based compound; and a glyceryl ether / ester compound or other preservatives; and 3) a step of adjusting the pH to 5.0-8.0.

[0019] The branched diol compound is one or more selected from the group consisting of 2-methyl-1,3-propanediol, 2,2-dimethyl-1,3-propanediol, 2-methyl-2-propyl-1,3-propanediol, and 3-methyl-1,3-butanediol, preferably 2-methyl-1,3-propanediol, The linear diol compound is one or more selected from the group consisting of 1,3-propanediol, 1,3-butanediol, 1,2-hexanediol, and 1,2-octanediol, preferably 1,2-hexanediol, The glyceryl ether / ester compound is one or more selected from the group consisting of ethylhexylglycerin, glyceryl caprylate, glyceryl stearate, glyceryl undecylenate, caprylyl glyceryl ether, and glyceryl laurate. Preferably, the glyceryl ether compound is ethylhexylglycerin and the glyceryl ester compound is glyceryl caprylate, The other preservative is phenoxyethanol.

[0020] The above step 1) includes the steps of immersing seeds in water, washing the seeds, wet-grinding the washed seeds at a weight ratio of 1:2 with water, filtering to obtain a grinding solution, mixing the grinding solution with sodium bicarbonate, and centrifuging to obtain oleosomes.

[0021] The seeds may include safflower seeds (Carthamus tinctorious seed), hemp seeds (Cannabis Sativa Seed), sunflower seeds (Helianthus annuus seed), coconuts (Cocos nucifera), torreya seeds (Torreya nucifera seed), camellia seeds (Camellia japonica seed), tea seeds (Camellia sinensis seed), chia seeds (Salvia Hispanica Seed), pomegranate seeds (Punica Granatum Seed), moringa seeds (Moringa Oleifera Seed), oil-tea camellia seeds (Camellia oleifera seed), rapeseed (Brassica napus seed), yuzu seeds (Citrus junos seed), olives (Olea europaea), grape seeds (Vitis vinifera seed), soybeans (Glycine max), rose hips (Rosa canina), macadamias (Macadamia), meadowfoam seeds (Limnanthes Alba seed), borage (Borago officinalis), cottonseed (Gossypium hirstutum), rice bran (Oryza Sativa seed), apricot seeds (Prunus armeniaca seed), corn (Zea mays), horse chestnut fruits (Aesculus hippocastanum fruit), palms (Elaeis Guineensis), palm kernels (Elaeis Guineensis Kernel), castor beans (Ricinus communis), hazelnuts (Corylus heterophylla), jojoba (Simmondsia chinensis), avocados (Persea americana), walnut seeds (Juglans regia seed), peanuts (Arachis Hypogaea), or argan (Argania Spinosa).

[0022] In another aspect, the present invention provides an oleosome formulation composition having excellent stability and antibacterial properties produced by the above production method, and a cosmetic containing the same.

[0023] The cosmetic is selected from the group consisting of skin care products, makeup products, hair care products, sunscreen agents, body care products, hand disinfectants, deodorants, products for removing keratin, topical application products, dermatological products, and acne treatment products.

[0024] The present invention also provides an oleosome formulation composition having excellent stability and antibacterial properties, comprising 79.3 to 94.5 parts by weight of oleosome, 0.5 to 4.0 parts by weight of 1,2 - hexanediol, 0.01 to 0.1 parts by weight of ethylhexylglycerin, 0.1 to 1 part by weight of glyceryl caprylate, and 4.8 to 20 parts by weight of 2 - methyl - 1,3 - propanediol.

[0025] The pH of the composition is characterized by being 5.0 to 8.0.

[0026] The composition may be formulated into a dosage form such as a pack, ointment, lotion, solubilized phase, suspension, emulsion, cream, gel, spray, poultice, plaster, patch, or painting ship.

Advantages of the Invention

[0027] The oleosome formulation composition produced by the production method according to the present invention can improve the stability of the oleosome formulation in the neutral pH range by treating the oleosome with a branched - chain diol - based compound. In addition, by mixing a linear diol - based compound, a glyceryl - based ether / ester compound, and other preservatives that damage the oleosome formulation with a branched - chain diol - based compound, the side effects that damage the oleosome formulation can be complemented, and the effect of significantly improving the formulation stability can be obtained. In addition, it has an excellent antiseptic effect by effectively suppressing the growth of bacteria, fungi, etc. to prevent microbial contamination, and can be effectively utilized in cosmetics, etc. by embodying the antiseptic boosting effect.

[0028] Moreover, by producing oleosomes in an oil-in-water emulsion dosage form from seeds, it can be produced in an environmentally friendly manner without an emulsifier or a solvent.

Brief Description of the Drawings

[0029]

Figure 1

Figure 2

Figure 3

Figure 4

Figure 5

Figure 6

Modes for Carrying Out the Invention

[0030] Hereinafter, the present invention will be described in more detail.

[0031] In the present application, the term "oleosome" means any discontinuous intracellular oil or wax storage organelle obtained from living cells. Oleosomes can be obtained from any cell containing the organelle, including plant cells, fungal cells, yeast cells (Leber, R et al, 1994, Yeast 10: 1421-28), bacterial cells (Pieper-Fuerst et al., 1994, J Bacteriol. 176: 4328-37), and algal cells (Roessler, PG, 1988, J Phycol. (London) 24: 394-400).

[0032] In a preferred specific example of the invention, the oleosome is obtained from plant cells, where "cells" each include the cells of pollen, spores, seeds, and vegetative plant organs in which the oleosome is present [General example: Huang, Ann Rev Plant Physiol. 43:177-200 (1992)]. More preferably, the oleosome used in the present invention is obtained from plant seeds.

[0033] The oleosome consists of an oil-in-water emulsion formed by oil globules provided with a lamellar liquid crystal coating dispersed in an aqueous phase.

[0034] In the present application, it may be, but is not limited to, an oil body generated from safflower seeds (Carthamus tinctorious seed). For example, it may be an oil body generated from hemp seeds (Cannabis Sativa Seed), sunflower seeds (Helianthus annuus seed), coconuts (Cocos nucifera), torreya seeds (Torreya nucifera seed), camellia seeds (Camellia japonica seed), tea seeds (Camellia sinensis seed), chia seeds (Salvia Hispanica Seed), pomegranate seeds (Punica Granatum Seed), moringa seeds (Moringa Oleifera Seed), oil-tea camellia seeds (Camellia oleifera seed), rapeseed (Brassica napus seed), yuzu seeds (Citrus junos seed), olives (Olea europaea), grape seeds (Vitis vinifera seed), soybeans (Glycine max), rose hips (Rosa canina), macadamia nuts (Macadamia), meadowfoam seeds (Limnanthes Alba seed), borage (Borago officinalis), cottonseed (Gossypium hirstutum), rice bran (Oryza Sativa seed), apricot seeds (Prunus armeniaca seed), corn (Zea mays), horse chestnut fruits (Aesculus hippocastanum fruit), palm (Elaeis Guineensis), palm kernels (Elaeis Guineensis Kernel), castor beans (Ricinus communis), hazelnuts (Corylus heterophylla), jojoba (Simmondsia chinensis), avocados (Persea americana), walnut seeds (Juglans regia seed), peanuts (Arachis Hypogaea) or argan (Argania Spinosa).

[0035] In the present application, the term "diol" means a compound containing two hydroxy groups (-OH).

[0036] The present invention provides a method for producing an oleosome formulation composition having excellent stability and antibacterial properties, and an oleosome formulation composition produced therefrom.

[0037] The method for producing an oleosome formulation composition having excellent stability and antibacterial properties according to the present invention includes: 1) a step of producing oleosomes; 2) treating the oleosomes with a mixture of a C1-C5 branched diol compound; a C1-C 10 linear diol compound; and a glyceryl ether / ester compound or other preservative; and 3) a step of adjusting the pH to 5.0-8.0.

[0038] The antibacterial property means an activity inhibitory effect against bacteria, fungi or viruses.

[0039] The bacteria include, but are not limited to, Bacillus subtilis, Pseudomonas aeruginosa, Escherichia coli, or Staphylococcus aureus.

[0040] The fungi may include, but are not limited to, Candida albicans or Aspergillus niger.

[0041] The above step 1) includes a step of immersing seeds in water, a step of washing the seeds, a step of wet-milling the washed seeds at a weight ratio of 1:2 with water, a step of filtering to obtain a pulverized solution, a step of mixing the pulverized solution with sodium bicarbonate, and a step of centrifuging to obtain oleosomes.

[0042] The seeds may include, but are not limited to, safflower seeds (Carthamus tinctorious seed), hemp seeds (Cannabis Sativa Seed), sunflower seeds (Helianthus annuus seed), coconuts (Cocos nucifera), kaya seeds (Torreya nucifera seed), camellia seeds (Camellia japonica seed), tea seeds (Camellia sinensis seed), chia seeds (Salvia Hispanica Seed), pomegranate seeds (Punica Granatum Seed), moringa seeds (Moringa Oleifera Seed), oil tea seeds (Camellia oleifera seed), rapeseed (Brassica napus seed), yuzu seeds (Citrus junos seed), olives (Olea europaea), grape seeds (Vitis vinifera seed), soybeans (Glycine max), rose hips (Rosa canina), macadamia nuts (Macadamia), meadowfoam seeds (Limnanthes Alba seed), borage (Borago officinalis), cottonseed (Gossypium hirstutum), rice bran (Oryza Sativa seed), apricot seeds (Prunus armeniaca seed), corn (Zea mays), horse chestnut fruits (Aesculus hippocastanum fruit), palm (Elaeis Guineensis), palm kernels (Elaeis Guineensis Kernel), castor beans (Ricinus communis), hazelnuts (Corylus heterophylla), jojoba (Simmondsia chinensis), avocados (Persea americana), walnut seeds (Juglans regia seed), peanuts (Arachis Hypogaea) or argan (Argania Spinosa).

[0043] In the step of immersing the seeds in water, the immersion may be carried out for 1 to 2 days, but is not limited thereto. Prior to pulverization, the seeds may be immersed in water to absorb liquid, softening the cell walls to facilitate the pulverization process. Since long-term liquid absorption can mimic the germination process, the composition of the seed components can be changed to a specifically advantageous degree.

[0044] Also, the pulverized seed fraction can be filtered to remove solid contaminants such as seed husks, fibrous substances, insoluble carbohydrates and proteins, and other insoluble contaminants. The filtration may include the steps of primary filtration through a mesh screen and secondary filtration through a cotton cloth, but is not limited thereto.

[0045] The concentration of the sodium hydrogen carbonate may be 0.1N, but is not limited thereto.

[0046] The branched diol-based compound may be one or more selected from the group consisting of 2-methyl-1,3-propanediol, 2,2-dimethyl-1,3-propanediol, 2-methyl-2-propyl-1,3-propanediol, and 3-methyl-1,3-butanediol, and preferably may be 2-methyl-1,3-propanediol.

[0047] The linear diol-based compound may be selected from the group consisting of 1,3-propanediol, 1,3-butanediol, 1,2-hexanediol, and 1,2-octanediol, and preferably may be 1,2-hexanediol.

[0048] The glyceryl ether / ester compound may be selected from the group consisting of Ethylhexylglycerin, Glyceryl Caprylate, Glyceryl Stearate, Glyceryl Undecylenate, Caprylyl Glyceryl Ether, and Glyceryl Laurate, and preferably may be Ethylhexylglycerin and / or Glyceryl Caprylate.

[0049] The other preservative may be Phenoxyethanol.

[0050] The above step 2) may preferably be to treat the oleosome with a mixture of 2-Methyl-1,3-propanediol, 1,2-Hexanediol, Ethylhexylglycerin, Glyceryl Caprylate, and Phenoxyethanol.

[0051] When a branched diol compound and a linear diol compound are used in combination, they have an excellent antimicrobial contamination prevention effect compared to when each is used alone, and have an anti-corrosion boosting effect on compounds that have insufficient anti-corrosion effect when used alone. In addition, the branched diol compound prevents the phenomenon that a linear diol compound, a glyceryl ether / ester compound, or other preservatives damage the oleosome preparation, and plays a role in stably maintaining the oleosome preparation.

[0052] In another aspect, the present invention provides an oleosome preparation composition having excellent stability and antibacterial properties produced by the above production method, and a cosmetic containing the same.

[0053] The cosmetic may be selected from the group consisting of, but not limited to, skin care products, makeup products, hair care products, sunscreen agents, body care products, hand sanitizers, deodorants, products for removing keratin, topical application products, dermatological products, and acne treatment products.

[0054] The present invention also provides an oleosome formulation composition having excellent stability and antibacterial properties, which contains 79.3 to 94.5 parts by weight of oleosome, 0.5 to 4.0 parts by weight of 1,2 - hexanediol, 0.01 to 0.1 parts by weight of ethylhexylglycerin, 0.1 to 1 part by weight of glyceryl caprylate, and 4.8 to 20 parts by weight of 2 - methyl - 1,3 - propanediol.

[0055] The pH of the composition is characterized by being 5.0 to 8.0, and stability can be maintained within the above pH range.

[0056] The oleosome formulation composition mixed within the above range is not limited in its dosage form and can be formulated into any dosage form well - known in the art. Examples of dosage forms include, in addition to cosmetics such as lotions, creams, and emulsions, topical skin bases such as ointments, solubilized phases, suspensions, gels, sprays, poultices, plasters, patches, or painting ships. The blending amounts of these dosage forms may be appropriately selected and blended by ordinary techniques in the art to obtain the desired effects. For example, the oleosome composition may be contained at 0.1% to 1.0% by weight based on the total weight of the cosmetic composition, but is not limited thereto.

[0057] Hereinafter, the present invention will be described in detail based on examples, but the present invention is not limited by these examples.

[0058] Example 1. Preparation of Oleosome After immersing 1 kg of plant seeds in 1 L of water at room temperature for about 1 to 2 days, they were washed about 1 to 2 times with water. The washed seeds were wet-milled using a mortar and pestle at a ratio of 1:2 with water, and the pulverized solution was obtained by first filtering through a mesh screen and then second filtering through a cotton cloth. After supplying water and sodium hydrogen carbonate at a final volume of 7 L so that the concentration of sodium hydrogen carbonate was 0.1 N, centrifugation was performed at room temperature using a three-phase centrifuge to obtain oleosomes.

[0059] An oleosome composition for each plant seed was produced by the production method of Example 1 above. In Examples 1-1 to 1-36 below, as the linear diol-based compound, 1,3-propanediol (1,3-Propanediol; hereinafter abbreviated as PD), 1,3-butanediol (1,3-Butanediol; hereinafter abbreviated as BD), 1,2-hexanediol (1,2-Hexanediol; hereinafter abbreviated as HD), or 1,2-octanediol (1,2-Octanediol; hereinafter abbreviated as OD) was used, and as the branched diol-based compound, 2-methyl-1,3-propanediol (2-Methyl-1,3-propanediol; hereinafter abbreviated as MP), 2,2-dimethyl-1,3-propanediol (2,2-Dimethyl-1,3-propanediol; hereinafter abbreviated as DP), 2-methyl-2-propyl-1,3-propanediol (2-Methyl-2-propyl-1,3-propanediol; hereinafter abbreviated as MPP), or 3-methyl-1,3-butanediol (3-Methyl-1,3-butanediol; hereinafter abbreviated as MB) was used. As the glyceryl ether compound, ethylhexylglycerin (Ethylhexylglycerin; hereinafter abbreviated as EHG) was used, as the glyceryl ester compound, glyceryl caprylate (Glyceryl Caprylate; hereinafter abbreviated as GC) was used, and as the other preservative, phenoxyethanol (Phenoxyethanol; hereinafter abbreviated as PE) was used.

[0060] [Example 1-1] to [Example 1-11] Carthamus tinctorius oleosome Using safflower seeds as plant seeds, a safflower oleosome composition was produced by the production method of Example 1 described above. Table 1 below shows the components and contents (parts by weight) of the safflower oleosome composition.

[0061]

Table 1

[0062] [Example 1-12]~[Example 1-22] Hempseed oleosome Using hemp seeds as plant seeds, a hemp seed oleosome composition was produced by the production method of Example 1 described above. Table 2 below shows the components and contents (parts by weight) of the hemp seed oleosome composition.

[0063]

Table 2

[0064] [Example 1-23]~[Example 1-36] Camellia japonica oleosome Using camellia seeds as plant seeds, a camellia oleosome composition was produced by the production method of Example 1 described above. Table 3 below shows the components and contents (parts by weight) of the camellia oleosome composition.

[0065]

Table 3

[0066] [Comparative Example] Oleosomes were produced in the same manner as in Example 1 described above. Referring to Tables 4, 5, and 6 below, safflower oleosome compositions (Comparative Examples 1-1 to 1-5), hemp seed oleosome compositions (Comparative Examples 1-6 to 1-10), and camellia oleosome compositions (Comparative Examples 1-11 to 1-25) were produced as comparative target compositions.

[0067]

Table 4

[0068]

Table 5

[0069]

Table 6

[0070] Experimental Example 1. Stability Evaluation of Oleosome Formulation Compositions by Mixing Branched Diol Compounds, Linear Diol Compounds, Glyceryl Ether / Ester Compounds, and Other Preservative Compounds In the pH range of 5 to 8 where the oleosome formulation is stable, the branched diol compound, linear diol compound, glyceryl ether / ester compound, and other preservative compounds were each treated on the oleosome and centrifuged at 10,000 rpm to confirm the stability of the oleosome formulation composition. The degree of oil separation in the oleosome was confirmed over time, and the separation degree was visually evaluated and expressed as +++ (extremely stable), ++ (stable), + (somewhat stable), - (somewhat unstable), -- (unstable), --- (extremely unstable).

[0071] Referring to Table 7 and Figure 1 below, when the linear diol compound, glyceryl ether / ester compound, and other preservatives were treated alone as in Comparative Examples 1-1 to 1-15, 1-20, 1-22, and 1-25, it was confirmed that the oleosome formulation became unstable and oil separation occurred. However, when the C1 to C5 branched diol compounds were treated alone as in Examples 1-1 to 1-4, 1-12 to 1-15, and 1-23 to 1-26, it can be seen that the formulation was maintained much more stably than the linear diol compound, glyceryl ether / ester compound, and other preservatives, and no oil separation occurred.

[0072]

Table 7

[0073] Also, referring to Table 8 and Figure 2 below, when a mixture of a linear diol compound and a glyceryl ether / ester compound or other preservatives is dispersed in a branched diol compound and treated with oleosomes, it was confirmed that the preparation can be stably retained without damaging the formulation (Examples 1-5 to 1-11, 1-16 to 1-22, 1-27 to 1-30, 1-34 to 1-36). From this, it can be seen that the branched diol compound can stably retain the oleosome formulation.

[0074]

Table 8

[0075] Experimental Example 2. Confirmation of the Optimal pH for the Stability of the Oleosome Formulation Composition After subjecting oleosomes to acidic, neutral, and alkaline conditions, a dosage form stability test was conducted. The pH was adjusted to three conditions, and after treating each with a composition in which 1,2-hexanediol (hereinafter abbreviated as HD) and 2-methyl-1,3-propanediol (hereinafter abbreviated as MPD) were mixed, when centrifugation was performed at 10,000 rpm, the degree of oil separation in the oleosomes was confirmed over time, and the degree of separation was visually evaluated and expressed as +++ (extremely stable), ++ (stable), + (somewhat stable), - (somewhat unstable), -- (unstable), --- (extremely unstable).

[0076] Referring to Table 9 and Figure 3 below, in the untreated group, the oil was stable without separation under all conditions (Comparative Examples 1-11). In the mixed composition treatment group, it was confirmed that significant oil separation occurred under the conditions of pH 4-5 (acidic), and it was stable under the conditions of pH 5-7 (neutral) and pH 7-8 (alkaline) (Examples 1-27). Thus, it was confirmed that the said composition could not stably hold the oleosome formulation under acidic conditions, but could stably hold the oleosome formulation under neutral and alkaline conditions. Also, the color of the oleosome formulation was maintained under neutral and alkaline conditions, but it was confirmed that the color of the oleosome formulation itself also changed somewhat to yellow and was unstable under acidic conditions. As a result of observing the particles of the oleosome formulation by pH under a microscope, it was confirmed that the oleosome particles were uniformly distributed and had fluidity under neutral and alkaline conditions, and under acidic conditions, the particles agglomerated and there was a lack of fluidity, and a phenomenon of oil particles splashing was observed. From this, it can be seen that when applying the mixed composition of 1,2-hexanediol and 2-methyl-1,3-propanediol to the oleosome formulation, neutral and alkaline conditions are optimal for stably holding the oleosome formulation.

[0077]

Table 9

[0078] Experimental Example 3. Confirmation of the effect of preventing microbial contamination of the oleosome formulation composition To confirm the effect of preventing microbial contamination of the compound composition treated with oleosomes, it was confirmed whether residual bacteria were detected in the oleosomes 7 days after treating the compound. For the evaluation of the antiseptic effect, oleosomes treated with each compound were added to MLA (Modified letheen Agar) medium, which is a bacterial culture medium, and SDA (Sabouraud’s dextrose agar) medium, which is a fungal culture medium, at different concentrations, solidified in Petri dishes to prepare solid media, and then the growth states of the cultured bacteria and molds were observed. The bacteria were cultured at 37 °C for 48 hours, and the fungi were cultured at 30 °C for 72 hours, and then the presence or absence of bacteria detection was observed to confirm the composition and concentration that inhibit the growth of bacteria. The bacteria may be Bacillus subtilis (B. subtilis), Pseudomonas aeruginosa (P. aeruginosa), Escherichia coli (E. coli), and Staphylococcus aureus (S. aureus), and the fungi may be Candida albicans (C. albicans) and Aspergillus niger (A. niger).

[0079] Referring to Table 10 and Figure 4 below, it was found that oleosomes treated with 1,2 - hexanediol and 2 - methyl - 1,3 - propanediol alone had both bacteria and fungi detected (Comparative Example 1 - 17, Comparative Example 1 - 18, Example 1 - 23, Example 1 - 31). When 1,2 - hexanediol was treated alone at 2%, it was confirmed that the growth of bacteria was inhibited by 90% or more and the growth of fungi was inhibited by 100% (Comparative Example 1 - 16), but there was a side effect of destabilizing the oleosome preparation, which was unsuitable for application to oleosomes. However, when treated with 1,2 - hexanediol and 2 - methyl - 1,3 - propanediol (1:5) at 2%, both bacteria and fungi showed 100% growth inhibition and an antiseptic effect, and it was confirmed that the oleosome preparation was also stably maintained (Example 1 - 27). Thus, it can be seen that this composition has the effect of maintaining excellent stability of the oleosome preparation by preventing bacterial contamination of the oleosome and inhibiting the growth of bacteria.

[0080]

Table 10

[0081] In Table 10 above, the notation of the presence or absence of microbial growth inhibition is as follows. -: No growth, +: <10 2 Detection, ++: <10 3 Detection, +++: >10 3 Detection

[0082] Experimental Example 4. Antimicrobial Boosting Effect of the Mixed Composition of 1,2-Hexanediol and 2-Methyl-1,3-propanediol The antimicrobial boosting effect was confirmed when an oleosome was treated by mixing both another preservative and a mixed composition of 1,2-hexanediol and 2-methyl-1,3-propanediol.

[0083] Referring to Table 11 and FIGS. 5 to 7 below, among the glyceryl ether compounds generally used in cosmetics, Ethylhexylglycerin (hereinafter abbreviated as EHG), among the glyceryl ester compounds, Glyceryl Caprylate (hereinafter abbreviated as GC), and Phenoxyethanol (hereinafter abbreviated as PE) as another preservative were tested. When these mixtures were treated with an oleosome alone, it was confirmed that the antimicrobial effect was somewhat inferior even at high contents (Comparative Examples 1-19 to 1-25). However, as a result of treating each compound at a further lower concentration in a mixed composition of 1% of 1,2-hexanediol and 5% of 2-methyl-1,3-propanediol, it was confirmed that both bacteria and fungi were inhibited from growing by 100% and there was an antimicrobial effect. Also, when the mixed composition of 1,2-hexanediol and 2-methyl-1,3-propanediol (1:5) was treated alone at 2% or less, the antimicrobial effect was somewhat inferior (Example 1-32), but when treated together with each of the other compounds, the antimicrobial power was improved at 1%. From this, it was confirmed that the mixed composition of 1,2-hexanediol and 2-methyl-1,3-propanediol is excellent in the effect of boosting the antimicrobial effect of other compounds (Examples 1-34 to 1-36).

[0084]

Table 11

[0085] In the above Table 11, the notations for the presence or absence of microbial growth inhibition are as follows. -: No growth, +: <10 2 detection, ++: <10 3 detection, +++: >10 3 detection

[0086] As described above, the present inventors conducted tests on various compounds in order to find a mixture that stably holds the oleosome preparation and has an antiseptic effect. Among linear diol-based, branched diol-based, glyceryl ester / ether compounds, and other preservatives, 1,2-hexanediol, 2-methyl-1,3-propanediol, ethylhexylglycerin, glyceryl caprylate, and phenoxyethanol, which are commonly used compounds, were selected, and the formulation stability test and the effect of preventing microbial contamination were confirmed.

[0087] First, as a result of conducting a stability test by applying commonly used diol compounds, it was confirmed that linear diol compounds, glyceryl esters / ethers compounds, and other preservatives destabilize the oleosome formulation and cause oil leakage. Specifically, it was confirmed that branched diol compounds effectively maintain the stability of the oleosome formulation. As linear diol compounds, 1,2-propanediol, 1,3-propanediol, 1,3-butanediol, 1,2-hexanediol, etc. were confirmed. As glyceryl esters / ethers compounds, ethylhexylglycerin, glyceryl caprylate, etc. were confirmed. As other preservatives, phenoxyethanol, etc. were confirmed. As branched diol compounds, 2-methyl-1,3-propanediol, 2,2-dimethyl-1,3-propanediol, 2-methyl-2-propyl-1,3-propanediol, 3-methyl-1,3-butanediol, etc. were confirmed. In terms of structural characteristics, the linear structure weakens the "spherical structure covered with a single-layer phospholipid", which is the specific structure of the oleosome, resulting in oil leakage. However, the branched structure was found to strengthen the oleosome structure and stabilize the formulation, preventing oil leakage.

[0088] Specifically, linear diol compounds, glyceryl esters / ethers compounds, and other preservatives alone damage the oleosome formulation. However, when mixed with branched diol compounds and applied to the oleosome formulation, it was confirmed that they can stably maintain the oleosome formulation. Thus, it was found that branched diol compounds have the effect of preventing the phenomenon that linear diol compounds, glyceryl esters / ethers compounds, and other preservatives damage the oleosome formulation.

[0089] When 2-methyl-1,3-propanediol was mixed with 1,2-hexanediol, ethylhexylglycerin, glyceryl caprylate, and phenoxyethanol and tested in an oleosome formulation, the oleosome formulation was stably maintained and no oil leakage occurred. When 1,2-hexanediol, ethylhexylglycerin, glyceryl caprylate, and phenoxyethanol were individually treated directly on the oleosome formulation, the oleosome formulation was damaged and an oil leakage occurred. However, when 1,2-hexanediol, ethylhexylglycerin, glyceryl caprylate, and phenoxyethanol were dispersed and stabilized in 2-methyl-1,3-propanediol and then treated on the oleosome formulation, it was confirmed that the oleosome formulation was stabilized and no oil leakage occurred.

[0090] Furthermore, when the anti-microbial contamination effect was confirmed, when 1,2-hexanediol and 2-methyl-1,3-propanediol were used alone, they were inferior in the anti-microbial contamination effect. However, when both were used in combination, it was confirmed that the oleosome formulation was stably maintained and the anti-microbial contamination effect was also much superior.

[0091] In addition, other compounds (ethylhexylglycerin, phenoxyethanol, glyceryl caprylate) that have the problem of insufficient anti-corrosion effect and need to be treated in a large amount when used alone were tested by being treated together with the mixed composition of 1,2-hexanediol and 2-methyl-1,3-propanediol. As a result, it was confirmed that even in a smaller amount, they are superior in the prevention effect of microbial contamination, and the oleosome formulation was also stably maintained. Thereby, the anti-corrosion boosting effect of the mixed composition of 1,2-hexanediol and methylpropanediol was also confirmed.

[0092] Formulation Example An ultraviolet-blocking emulsion formulation containing an oleosome formulation

[0093] Phase 1 Oil phase Stabilized oleosome (oleosome 88%, 1,2 - hexanediol 2%, 2 - methyl - 1,3 - propanediol 10%) 12.0% Octyl methoxycinnamate 1.0% Octocrylene 0.5% Ethylhexyl salicylate 0.5% Benzophenone - 3 0.5% Titanium dioxide 2.0% Novemer EC - 1 1.1%

[0094] Phase 2 Aqueous phase Urea 5.0% Polyglycerin - 10 5.0% Water up to 100%

[0095] Phase 3 Fragrance 0.14% Preservative 0.4%

[0096] Treatment process 1. The components of Phase 1 were added together while stirring at low shear. 2. The components of Phase 2 were added together. 3. Phase 2 was gradually added to Phase 1 while mixing at low shear. 4. Phase 3 was added and stirred.

[0097] The above description is merely illustrative of the present invention. Those with ordinary knowledge in the technical field to which the present invention pertains can make various modifications without departing from the essential characteristics of the present invention. Therefore, the embodiments disclosed in this specification are for the purpose of explanation rather than limitation of the present invention, and the idea and scope of the present invention are not limited by such embodiments. The protection scope of the present invention should be interpreted according to the appended claims, and any technology within the equivalent scope should be construed as being included within the scope of the rights of the present invention.

Industrial Applicability

[0098] According to the present invention, it is possible to produce an oleosome having an excellent antiseptic effect by improving the formulation stability, effectively suppressing the growth of bacteria, and preventing microbial contamination, and it can be effectively utilized in cosmetics and the like.

Claims

1. 1) a step of manufacturing an oleosome; 2) treating the oleosome with a mixture of a branched diol compound having C １ to C ５ ; a linear diol compound having C １ to C １０ ; and a glyceryl ether / ester compound or other preservative; 3) a step of adjusting the pH to 5.0 to 8.0, wherein the branched diol compound is one or more selected from the group consisting of 2-methyl-1,3-propanediol, 2,2-dimethyl-1,3-propanediol, 2-methyl-2-propyl-1,3-propanediol, and 3-methyl-1,3-butanediol; the linear diol compound is one or more selected from the group consisting of 1,3-propanediol, 1,3-butanediol, 1,2-hexanediol, and 1,2-octanediol; the glyceryl ether / ester compound is one or more selected from the group consisting of ethylhexylglycerin, glyceryl caprylate, glyceryl stearate, glyceryl undecylenate, caprylyl glyceryl ether, and glyceryl laurate; and the other preservative is phenoxyethanol, and a method for manufacturing an oleosome preparation composition having excellent stability and antibacterial properties.

2. The branched diol compound is 2-methyl-1,3-propanediol, the linear diol compound is 1,2-hexanediol, the glyceryl ether compound is ethylhexylglycerin, the glyceryl ester compound is glyceryl caprylate, and the other preservative is phenoxyethanol. A method for producing an oleosome preparation composition according to claim 1, characterized in that

3. The step (1) is soaking the seeds in water; washing the seeds; wet-milling the washed seeds at a weight ratio of 1:2 with water; filtering to obtain a pulverized solution; mixing the pulverized solution with sodium hydrogen carbonate; centrifuging to obtain oleosomes. A method for producing an oleosome preparation composition according to claim 1, characterized by comprising

4. The seeds are plant seeds including safflower seeds, hemp seeds, sunflower seeds, camellia seeds, yuzu seeds, or rape seeds. A method for producing an oleosome preparation composition according to claim 3, characterized in that

5. An oleosome preparation composition having excellent stability and antibacterial properties, produced by the production method according to any one of claims 1 to 4.

6. A cosmetic containing the oleosome preparation composition having excellent stability and antibacterial properties according to claim 5.

7. The cosmetic according to claim 6, characterized in that it is selected from the group consisting of skin care products, makeup products, hair care products, sunscreen agents, body care products, hand disinfectants, deodorants, products for removing keratin, topical application products, dermatological products, and acne treatment products.

8. An oleosome preparation composition having excellent stability and antibacterial properties, comprising 79.3 to 94.5 parts by weight of oleosome, 0.5 to 4.0 parts by weight of 1,2 - hexanediol, 0.01 to 0.1 parts by weight of ethylhexylglycerin, 0.1 to 1 part by weight of glyceryl caprylate, and 4.8 to 20 parts by weight of 2 - methyl - 1,3 - propanediol.

9. The oleosome preparation composition according to claim 8, characterized in that the pH of the composition is 5.0 to 8.

0.

10. The oleosome preparation composition according to claim 8, characterized in that the composition is formulated into a dosage form such as a pack, ointment, lotion, solubilized phase, suspension, emulsion, cream, gel, spray, poultice, plaster, patch, or paint-on ship.

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