KR102304868B1 - The preservative composition with freezing point depression for cosmetics and the process for preparing the same - Google Patents

Abstract

The present invention relates to a freezing point lowering preservative composition for cosmetics and a method for manufacturing the same, and more particularly, by lowering the freezing point while maintaining the chemical properties of the cosmetic composition to prevent solidification according to the drop in outdoor air temperature in winter and summer, so that it is liquid at room temperature It relates to a freezing point lowering preservative composition for cosmetics that can be maintained as an antiseptic composition and a method for manufacturing the same. According to the freezing point lowering composition for cosmetics according to the present invention, 1,2-octanediol is used and a hydrocarbon-based material containing a hydroxyl group is used to maintain the liquid phase due to the freezing point lowering effect while maintaining the existing 1,2-octanediol. It can preserve the preservative power it had. In addition, it can be a promising preservative that can replace parabens and phenoxyethanol that are harmful to the human body and cause skin irritation and allergies, which have been used as preservatives in cosmetic compositions.

Description

The preservative composition with freezing point depression for cosmetics and the process for preparing the same

The present invention relates to a freezing point lowering preservative composition for cosmetics and a method for manufacturing the same, and more particularly, by lowering the freezing point while maintaining the chemical properties of the cosmetic composition to prevent solidification according to the drop in outdoor air temperature in winter and summer, so that it is liquid at room temperature It relates to a freezing point lowering preservative composition for cosmetics that can be maintained as an antiseptic composition and a method for manufacturing the same.

Compositions for external use such as cosmetics are difficult to avoid contamination by microorganisms during the manufacturing process or use.

Therefore, in the composition for external use, preservatives such as paraoxybenzoic acid esters (commonly referred to as parabens) or preservatives such as imidazolidinyl urea and phenoxyethanol in order to inhibit the growth of microorganisms or to kill microorganisms to improve product preservation are used in combination.

Of course, it is possible to prepare an external composition that does not contain preservatives such as parabens and imidazolidinyl urea. Complementary and complicated means such as the use of small-scale containers for this purpose or the use of non-refillable small-volume containers (bagless tube, dispenser container, etc.)

Several types of parabens (69 types) used as preservatives among ingredients necessary to make cosmetics are classified as carcinogens by the Food and Drug Administration (FDA) of the United States, and their use is being regulated in each country.

Accordingly, since 2008, when the all-ingredient labeling system was implemented for cosmetic handling companies, many cosmetic-related companies started researching ingredients that could substitute for parabens.

On the other hand, in the case of existing preservatives, their use for preservation of external preparations such as cosmetics is gradually decreasing due to safety concerns, such as skin irritation and carcinogenicity, while some linear forms of 1,2-alkandiol are It has been evaluated as a relatively safe material compared to antibacterial activity and existing preservatives (United States Patent No. 3970759, 1976), and its use is increasing.

These 1,2-alkandiols have different material properties depending on the number of carbon atoms in the constituent materials, and in particular, there is a big difference in antibacterial power and irritation to the skin. That is, if the carbon number is 6 or less, it is liquid at room temperature and has low skin irritation but has weak antibacterial activity.

Therefore, 1,2-Alkanediols having 6 or less carbon atoms are widely used by applying them to general cosmetics that can come into direct contact with the skin. As it can be applied to off products (shampoo, rinse, etc.), its usage has been increasing recently, but since it is in a solid state at room temperature, it is a problem that causes great inconvenience in use.

U.S. Patent No. 03,970,759 (1976.07.20.)

The present inventors have intensively studied to improve the problems associated with the prior art as described above and to solve the problem that 1,2-alkanediols having 8 or more carbon atoms are solidified at room temperature. As a result, alkanediol; and a hydrocarbon-based material containing a hydroxyl group, and the freezing point lowering preservative composition for cosmetics, characterized in that it begins to be liquefied at a temperature of 4° C. or higher, or partially liquefies, or forms a uniform liquid phase is 1,2- To complete the present invention, discovering that octanediol can provide convenience for use by consumers by resolving the problem of solidification at room temperature while maintaining the original cosmetic properties of 1,2-alkanediol, such as preservative, moisturizing and lubricating power. reached

Therefore, the present invention solves the problem of solidification at room temperature of 1,2-octanediol, which is widely used as a cosmetic preservative, moisturizer, lubricant, etc., while maintaining the original preservative power of 1,2-octanediol for convenience for consumers. An object of the present invention is to provide an alkanediol freezing point lowering preservative composition and a method for preparing the same.

Another object of the present invention is to provide a preservative composition for lowering the freezing point of alkanediol that can replace parabens, which are preservatives used in conventional cosmetics or detergents, and a method for preparing the same.

The object of the present invention as described above is alkanediol; and a hydrocarbon-based material containing a hydroxyl group, and the freezing point lowering preservative composition for cosmetics, characterized in that it starts to be liquefied at a temperature of 4° C. or more, is partially liquefied, or forms a uniform liquid phase, and preparation thereof method can be achieved.

According to the freezing point lowering composition for cosmetics according to the present invention, 1,2-octanediol is used and a hydrocarbon-based material containing a hydroxyl group is used to maintain the liquid phase due to the freezing point lowering effect while maintaining the existing 1,2-octanediol. It can preserve the preservative power it had. In addition, it can be a promising preservative that can replace parabens and phenoxyethanol that are harmful to the human body and cause skin irritation and allergies, which have been used as preservatives in cosmetic compositions.

1 is a graph schematically showing the freezing point descending of a solution.
2 is a photograph showing the freezing point reduction test results for the freezing point reduction composition prepared using 1,3-butylene glycol.
3 is a photograph showing the results of a freezing point reduction test for a freezing point reduction composition prepared using ethanol.
4 is a photograph showing the results of a freezing point reduction test for a freezing point reduction composition prepared using a mixture (BP) in which propylene glycol and 1,3-butylene glycol were mixed in a 1:1 ratio.

The present invention, in one aspect, alkanediol; and a hydrocarbon-based material including a hydroxyl group, and is liquefied at a temperature of 4° C. or higher or forms a uniform liquid phase, wherein the alkanediol is 1,2-octanediol or 1,2-decanediol; , The hydrocarbon-based material containing the hydroxyl group is 1,2-propanediol (= propylene glycol), 1,3-propanediol, 2-methyl-1,3-propanediol (MPO), 1,2-butanediol ( =butylene glycol), 1,3-butanediol, ethylhexyl glycerin, ethanol, and provides a cosmetic freezing point lowering preservative composition, characterized in that at least one selected from the group consisting of mixtures thereof.

The present invention, in yet another aspect, provides a freezing point lowering antiseptic composition for cosmetics, wherein the alkanediol functions as a preservative, a moisturizing agent or a lubricant.

The present invention, in another aspect,

(a) mixing a liquid alkanediol and a hydrocarbon-based material containing a hydroxyl group to prepare a homogeneous liquid mixture; and

(b) maintaining the liquid mixture of the homogeneous phase in a liquid state; wherein the alkanediol is 1,2-octanediol or 1,2-decanediol, and the hydrocarbon-based material including the hydroxyl group is 1, 2-propanediol, 1,3-propanediol, 2-methyl-1,3-propanediol (MPO), 1,2-butanediol, 1,3-butanediol, ethylhexylglycerin, ethanol and mixtures thereof It provides a method for manufacturing a cosmetic freezing point lowering preservative composition, characterized in that at least one selected from among.

In a further aspect, the present invention provides a method for preparing a freezing point lowering preservative composition for cosmetics, which further comprises a step of heating and liquefying the alkanediol when it is in a solid state prior to step (a). to provide.

In another further aspect, the present invention provides a composition for external application comprising the above-described freezing point lowering antiseptic composition according to the present invention as a main component of a preservative, a moisturizer, or a lubricant.

The present invention provides an external composition, characterized in that the composition for external use is a basic cosmetic, makeup cosmetic, hair cosmetic, ointment, personal care product, or home care product in another further aspect.

Hereinafter, a freezing point lowering composition for cosmetics and a method for manufacturing the same according to the present invention will be described with reference to the accompanying drawings.

The present invention may be embodied in various different forms, and thus is not limited to the embodiments described herein. And in order to clearly explain the present invention in the drawings, parts irrelevant to the description are omitted, and similar reference numerals are attached to similar parts throughout the specification.

In cosmetics or detergents, preservatives are usually used for stable material preservation. Parabens are the most commonly used preservatives. Parabens are classified as carcinogens, and because of their high skin irritation, the concentration range is limited. Also, recently, the number of people allergic to parabens is increasing. Since people who cause an allergic reaction will also react with parabens at very low concentrations, the demand for cosmetics without parabens is increasing.

However, since cosmetics without preservatives have poor storage stability and are difficult to manage as a commodity, a substance having a high stability and antiseptic effect on the human body is required.

Therefore, it is known that diol compounds such as alkanediols and alkylglyceryl ethers are used. These compounds are substances with good preservative power and have relatively high safety for the human body compared to parabens.

The present invention provides an excellent antiseptic effect by blending alkanediol, more specifically, any one or more of 1,2-octanediol and 1,2-decanediol, in a composition for external application. 1,2-octanediol, 1,2-decanediol (1,2-decanediol), which are a kind of alkanediol that can secure normal preservative power even when the compounding amount of chemical preservatives such as parabens is drastically reduced ) of any one or more of the freezing point lowering composition may be provided.

According to an embodiment of the present invention, in the freezing point lowering composition of an alkanediol, one or more hydroxy (OH) using any one or more of 1,2-octanediol and 1,2-decanediol ) A composition capable of lowering the freezing point of at least one of 1,2-octanediol and 1,2-decanediol, which are a kind of alkanediol, by mixing with a hydrocarbon-based material having a group is provided.

In the freezing point lowering composition of an alkanediol according to an embodiment of the present invention, the 'composition for external application' is a concept that encompasses the overall composition generally used for external use, for example, basic cosmetics, makeup cosmetics, hair cosmetics, etc. It refers to a composition that can be widely applied to various pharmaceuticals, such as cosmetics or ointments, or quasi-drugs. Furthermore, the present invention can be applied to these types of compositions for external use.

Examples of the cosmetics include, but are not limited to, personal care products, home care products, and various products such as shampoo, conditioner, wet tissue, and bath products.

Also, in one embodiment of the present invention, 'preservation' means resistance to all contaminating microorganisms such as bacteria, mold, yeast, and 'preservative power' means defense against these contaminating microorganisms.

Any one or more alkanediol of 1,2-octanediol and 1,2-decanediol having 8 or more carbon atoms and 10 or less carbon atoms is included in cosmetics to exhibit antibacterial activity It functions as a preservative, humectant, lubricant and solubilizer.

In particular, 1,2-octanediol and 1,2-decanediol used in the composition for lowering the freezing point of alkanediol according to the present invention can be maintained in a liquid state at a high temperature above the melting point. However, in the production process, it is packaged in a sealed container (drum or barrel) in a liquid state, solidified at room temperature, and then sold and distributed. cumbersome and inconvenient.

In the present invention, the term “room temperature” means a temperature of 4°C or higher to 35°C, more preferably 4°C to 31°C.

According to the present invention, when a hydrocarbon-based material containing a hydroxyl group is mixed with an alkanediol, the mixture begins to be liquefied at a temperature of 4° C. or higher, partially liquefied, or achieves a uniform liquid phase, and the temperature set above Within the range, liquefaction may be performed better as the temperature increases, and may proceed slowly as the temperature decreases. Therefore, when liquefaction proceeds at a relatively low temperature near 4°C, there may be a state in which a liquid and a solid coexist, and the properties of the mixture in this case maintain a stable state.

Therefore, in the present invention, the suitable mixing ratio is suitable to include a case in which a uniform liquid phase is rapidly formed, as well as a case in which a liquid phase and a solid phase coexist or a case in which liquefaction begins.

The present invention relates to 1,2-propanediol, 1,3-propanediol, 2-methyl-1,3-propanediol (MPO), 1,2-butanediol, 1,3-butanediol, ethylhexylglycerin, ethanol and these There is a technical feature in continuously maintaining functionality such as preservative power while maintaining a uniform liquid state by mixing a hydrocarbon-based material containing at least one hydroxyl group selected from the group consisting of a mixture of

The hydrocarbon-based material containing a hydroxyl group preferably used in the composition for lowering the freezing point of the present invention is more preferably 1,2-propanediol, 1,3-propanediol, 2-methyl-1,3-propanediol ( MPO), 1,2-butanediol, 1,3-butanediol, ethylhexyl glycerin, ethanol, and at least one selected from the group consisting of mixtures thereof may be used.

On the basis of known general chemistry, a solution with the same attraction between solute and solute, between solvent and solvent, and between solvent and solute is called an ideal solution. .

When the conditions of an ideal solution are satisfied, the properties of the solution are determined according to the amount (concentration) of the solute regardless of the type of solute. In other words, the properties are determined by the number of molecules that make up a substance, regardless of the kind. As such, a decrease in vapor pressure, an increase in boiling point, decrease in freezing point, and osmotic pressure of a solution in which a nonvolatile solute is dissolved in a pure solvent (such a solution is called an ideal solution following Raoult's law).

These are collectively called the overall solution, and are characteristic values of the solution that depend only on the concentration regardless of the type of solute.

In the case of a solution in which a non-volatile solute is dissolved in a pure solvent, a drop in the vapor pressure of the solution may occur. Evaporation occurs at the surface of a solvent or solution. The vapor pressure is the pressure exhibited by the evaporated solvent when the vaporization ↔ liquefaction phenomenon of the solvent at a certain temperature achieves a dynamic equilibrium state. Since evaporation is a phenomenon in which the solvent is vaporized, the solution is non-volatile compared to the pure solvent, and the solution in which the non-electrolyte solute is dissolved has reduced evaporation as much as there are solute particles on the surface. The reason is that, when there is only a solvent, solvent molecules evaporate from all surfaces of the solution at the surface, but as the number of particles of the solute increases, the relative surface area occupied by the solute expands, preventing evaporation of the solvent molecules. Therefore, the vapor pressure of the solution is lowered.

This phenomenon is called vapor pressure lowering, and this vapor pressure lowering can be expressed by Equation (1).

[Equation 1]

P = P ₀ (1-X _s ) (X _s : mole fraction of solute)

The phenomenon of boiling point rise can be understood from the explanation of vapor pressure drop. A decrease in the vapor pressure of a solution at a specific temperature may mean the same as that the vapor pressure at the boiling point of a pure solvent does not become 1 atm, which is the atmospheric pressure at normal times.

This means that the vapor pressure of the solution becomes 1 atm when the temperature is higher than the existing predetermined boiling point, and the solution can boil. The equation of the boiling point rise can be expressed as Equation (2).

[Equation 2]

T _b =K _b ⅹm _s (In Equation 2, T _b is the boiling point rising, K _b is the boiling point rising constant, m _s is the molality of the solute.)

If the definition of the freezing point is also chemically explained, it can be seen as the moment when the vapor pressure of the solution and the vapor pressure of the solid state of the solution become equal.

1 is a graph schematically showing the freezing point descending of a solution. Referring to FIG. 1 , in this case, since the solid state of the solution consists only of a pure solvent, the vapor pressure curve according to temperature is the same, and the solution may have a shape in which the vapor pressure curve according to temperature moves in the negative direction on the y-axis.

(Equation 3) can represent the freezing point depression of the solution as the molality of the solution (m _s ) and the freezing point depression (Kf) of the solution.

[Equation 3]

T _f = K _f ⅹm _s (where K _F is the freezing point rounding constant).

In the case of a dilute solution in which a non-volatile substance is dissolved, that is, close to an ideal solution, the degree of freezing point depression is proportional to the number of moles.

That is, if the difference between the freezing point of the net solvent and the freezing point of a solution in which the solute Wg is dissolved in 100 g of the solvent (decreasing the freezing point) is ΔT, the molecular weight M of the solution can be expressed in the form of Equation 4.

[Equation 4]

M = kW _g /ΔT (In Equation 4, k is called the melting point descending constant of the solvent.)

The freezing point depression can be calculated from the freezing point or heat of fusion of the solvent. Usually, the freezing point depression (k) is determined in a sample with known molecular weight (solution), and the substance to be measured W _g is weighed, and ΔT is By measuring, M can be obtained from Equation (4). As the solvent, water (H ₂ O), acetic acid (CH ₃ COOH), or benzene (C ₆ H ₆ ) may be used.

In this case, when a solute causes a chemical change in a solvent or when a solid solution is formed, the method for preparing a freezing point lowering composition of alkanediol according to an embodiment of the present invention cannot be used.

According to one embodiment of the present invention, paraoxybenzoic acid ester and imidazolidinyl urea, phenoxyethanol in the composition for external application of various pharmaceuticals or quasi-drugs such as various cosmetics or ointments such as basic cosmetics, makeup cosmetics, or hair cosmetics It has an excellent effect of providing a composition for external use that is excellent in preservative power and excellent in usability and safety without compounding chemical preservatives such as these. Of course, even in the case of 1,2-octanediol, although it is a substance that exhibits an antiseptic effect, a method of adding a very small amount to the cosmetic composition can be used because it corresponds to a substance with skin irritation.

Due to this effect, it can be used as a substitute for CMIT/MIT (Methylchloroisothiazolinone/Methylisothiazolinone) used in humidifiers, which was a problem in 2012, and can be used in wash-off cosmetics (shampoo, conditioner, etc.) and household detergents.

From this point of view, 1,2-octanediol can be used as a substitute for preservatives, antibacterial agents, and moisturizing agents in products that come into contact with the human body, such as cosmetic raw materials and household products.

Among the alkanediols, 1,2-pentanediol and 1,2-hexanediol have weak preservative power, but are less irritating to the skin despite being expensive, so their usage is gradually increasing. On the other hand, it is believed that 1,2-octanediol and 1,2-decanediol according to an embodiment of the present invention can expand their use area in the future when their properties are liquefied.

Hereinafter, a method for preparing the freezing point lowering composition according to the present invention will be described.

(a) liquefaction step of alkanediol

In step (a), when the alkali diol (eg, 1,2-octanediol) is in a solid state depending on the winter season or the surrounding environment, the alkali diol (eg, 1,2-octanediol) is heated using hot water or steam. to liquefy and use.

(b) preparing the liquid mixture in the homogeneous phase

A liquid alkanediol and a hydrocarbon-based material containing a hydroxyl group are mixed in a weight ratio of 10:2 to 10 to form a homogeneous liquid mixture.

The hydrocarbon-based material including the hydroxyl group is 1,2-propanediol, 1,3-propanediol, 2-methyl-1,3-propanediol (MPO), 1,2-butanediol, 1,3-butanediol, At least one selected from the group consisting of ethylhexylglycerin, ethanol, and mixtures thereof is preferable.

(c) maintaining the liquid state of the liquid mixture (prevent solidification)

The homogeneous liquid mixture prepared in step (b) is stored at ambient temperature to prevent solidification. When it is solidified, it is preferable to use it by heating or heating to form a homogeneous phase after liquefaction.

(Example)

Hereinafter, the present invention will be described in more detail based on the following examples. These examples are presented for the purpose of explaining the present invention more easily, and the present invention is not limited by these examples, and can be substituted and replaced with other equivalent examples within the scope without departing from the technical spirit of the present invention. It will be apparent to those of ordinary skill in the art to which the present invention pertains.

Example 1: Preparation of a composition for lowering the freezing point using alkaline diol and 1,2-propylene glycol

Various samples were prepared by mixing and dissolving 1,2-octanediol (OD) as a solvent and 1,2-propylene glycol (PG) of the following formula (1) in a weight ratio of 10:0 to 10, followed by 2 days at 4°C Afterwards, these were used in subsequent test examples.

[Formula 1]

HOCH ₂ C(OH)HCH ₃

Test Example 1: Freezing point drop test

The sample composition prepared in Example 1 was subjected to a freezing point drop test at 4° C. for 2 days, and the results are shown in Table 1. Table 1 is a result showing whether a solid material is formed after 2 days at 4°C. In the following examples, when the sample composition is a solid, it is denoted by "O", when the sample is liquefied and there is some solid content, it is denoted by "Δ", and when it is completely liquid, it is denoted by "X".

Sample name OD(g) PG(g) PG concentration (wt%) solid matter
Formation note Sample 1-1 10 0 0 O solidification Sample 1-1.5 10 0.5 4.7 O solidification Sample 1-2 10 One 9.1 O solidification Sample 1-3 10 2 16.7 △ solid + liquid Sample 1-4 10 3 23.1 △ solid + liquid Samples 1-5 10 4 28.6 X liquid Samples 1-6 10 5 33.3 X liquid Sample 1-7 10 6.8 40.5 X liquid Samples 1-8 10 10 50.0 X liquid (Abbreviation explanation) *OD: 1,2-Octanediol, PG: 1,2-Propylene Glycol

As shown in Table 1, in the formulation of 1,2-octanediol and 1,2-propylene glycol according to Example 1 of the present invention, liquefaction proceeds at a ratio of 10:2, and at a ratio of 10:4-10 It can be seen that no precipitate is formed.

Example 2: Preparation of a composition for lowering the freezing point using alkaline diol and 1,3-butylene glycol

Various samples were prepared by mixing and dissolving 1,2-octanediol (OD) and 1,3-butylene glycol (BG) in a weight ratio of 10:0 to 10 as a solvent, and after 2 days at 4°C, they were subsequently tested used in the example.

Test Example 2: Freezing point drop test

The melting point was compared for the freezing point lowering composition of various concentrations prepared in Example 2, and the results are shown in Table 2 below. Table 2 is a result showing whether a solid material is formed after 2 days at 4°C.

Sample name OD(g) BG(g) BG concentration
(wt%) solid matter
Formation note Sample 2-1 10 0 0 O solidification Sample 2-1.5 10 0.5 4.7 O solidification Sample 2-2 10 One 9.1 O solidification Sample 2-3 10 2 16.7 △ solid + liquid Sample 2-4 10 3 23.1 △ solid + liquid Sample 2-5 10 4 28.6 △ solid + liquid Sample 2-6 10 5 33.3 X liquid Sample 2-7 10 6.8 40.5 X liquid Sample 2-8 10 10 50.0 X liquid (Abbreviation explanation) *OD: 1,2-Octanediol, BG: 1,3-Butylene Glycol

As shown in Table 2, the mixture of 1,2-octanediol and 1,3-butylene glycol according to Example 2 of the present invention is liquefied at a ratio of 10:2, and a ratio of 10:5 to 10 It can be seen that no precipitates are formed.

Example 3: Preparation of a composition for lowering the freezing point using an alkalidiol and ethanol

Various samples were prepared by mixing and dissolving 1,2-octanediol (OD) and ethanol (EtOH) in a weight ratio of 10:0 to 10 as solvents, and after 2 days at 4°C, these were used in subsequent test examples.

Test Example 3: Freezing point drop test

The melting point was compared for the freezing point lowering composition of various concentrations prepared in Example 3, and the results are shown in Table 3 below. Table 3 is a result showing whether a solid material is formed after 2 days at 4°C.

Sample name OD EtOH (g) EtOH concentration (wt%) solid matter
Formation note No additives (OD: 100%) 10 0 0 O solidification Sample 3-1 10 0.5 4.7 O solidification Sample 3-2 10 One 9.1 △ solid + liquid Sample 3-3 10 2 16.7 △ solid + liquid Sample 3-4 10 3 23.1 X liquid Sample 3-5 10 4 28.6 X liquid Sample 3-6 10 5 33.3 X liquid Sample 3-7 10 6.8 40.5 X liquid Sample 3-8 10 10 50 X liquid (Abbreviation explanation) *OD: 1,2-Octanediol, EtOH: Ethyl Alcohol

From the results in Table 3, when ethanol is added to 1,2-octanediol, it can be confirmed that a liquid phase is formed even when a small amount of ethanol is added. That is, in the case of ethanol, liquefaction proceeds at a ratio of 10: 1, and exists as a liquid at a ratio of 10: 3, so that the liquid composition to be obtained in the present invention can be confirmed. This is considered to be because ethanol has a lower molecular weight than in the case of adding propylene glycol or 1,3-butylene glycol.

Example 4: Preparation of a composition for lowering the freezing point using alkalidiol and ethylhexylglycerin

Various samples were prepared by mixing and dissolving 1,2-octanediol (OD) and ethylhexylglycerin in a weight ratio of 10:0 to 10 as a solvent, and after 2 days at 4°C, these were used in subsequent test examples.

Test Example 4: Freezing point drop test

The sample composition prepared in Example 4 was subjected to a freezing point drop test at 4° C. for 2 days, and the results are shown in Table 4. Table 4 is a result showing whether a solid material is formed after 2 days at 4°C.

Sample name OD(g) EHG(g) Concentration (wt%) solid matter
Formation note Sample 4-1 10 0 0 O solidification Sample 4-1.5 10 0.5 4.7 O solidification Sample 4-2 10 One 9.1 △ solid + liquid Sample 4-3 10 2 16.7 △ solid + liquid Sample 4-4 10 3 23.1 △ solid + liquid Sample 4-5 10 4 28.6 X liquid Sample 4-6 10 5 33.3 X liquid Sample 4-7 10 6.8 40.5 X liquid Sample 4-8 10 10 50.0 X liquid (Abbreviation explanation) *OD: 1,2-Octanediol, EHG: Ethyl Hexyl Glycerine

As shown in Table 4, in the combination of 1,2-octanediol and ethylhexylglycerin according to Example 4 of the present invention, liquefaction proceeds at a ratio of 10: 1, and precipitates are formed at a ratio of 10: 4 to 10 It can be seen that it does not

Example 5: Preparation of a composition for lowering the freezing point using an alkalidiol and 1,3-propylene glycol

Various samples were prepared by mixing and dissolving 1,2-octanediol (OD) and 1,3-propylene glycol (PG) in a weight ratio of 10:0 to 10 as a solvent, and after 2 days at 4° C. was used in

Test Example 5: Freezing point drop test

The sample composition prepared in Example 5 was subjected to a freezing point drop test at 4° C. for 2 days, and the results are shown in Table 5. Table 5 is a result showing whether a solid material is formed after 2 days at 4°C.

Sample name OD(g) PD(g) PD concentration (wt%) solid matter
Formation note Sample 5-1 10 0 0 O solidification Sample 5-1.5 10 0.5 4.7 O solidification Sample 5-2 10 One 9.1 O solidification Sample 5-3 10 2 16.7 △ solid + liquid Sample 5-4 10 3 23.1 △ solid + liquid Sample 5-5 10 4 28.6 X liquid Sample 5-6 10 5 33.3 X liquid Sample 5-7 10 6.8 40.5 X liquid Samples 5-8 10 10 50.0 X liquid (Abbreviation explanation) *OD: 1,2-Octanediol, PD: 1,3-Propanediol

As shown in Table 5, the blending of 1,2-octanediol and 1,3-propanediol according to Example 5 of the present invention starts liquefaction at a ratio of 10:2, and at a ratio of 10:4-10 It can be seen that no precipitate is formed.

Example 6: Preparation of a composition for lowering the freezing point using a mixture of alkaline diol, 1,2-propylene glycol and 1,3-butylene glycol

As a solvent, a 1:1 mixture (BP) of 1,2-octanediol (OD) and 1,2-propylene glycol and 1,3-butylene glycol was mixed and dissolved in a weight ratio of 10:0 to 10 to prepare various samples. After 2 days at 4°C after preparation, they were used in subsequent test examples.

Test Example 6: Freezing point drop test

The melting point was compared for the freezing point lowering composition of various concentrations prepared in Example 6, and the results are shown in Table 6 below. Table 6 is a result showing whether a solid material is formed after 2 days at 4°C.

Sample name OD(g) BP
(BG/PG)(g) BP
density(%) solid matter
Formation note Sample 6-1 10 0 0 O solidification Sample 6-1.5 10 0.5 4.7 O solidification Sample 6-2 10 One 9.1 O solidification Sample 6-3 10 2 16.7 △ solid + liquid Sample 6-4 10 3 23.1 △ solid + liquid Sample 6-5 10 4 28.6 △ solid + liquid Sample 6-6 10 5 33.3 X liquid Sample 6-7 10 6.8 40.5 X liquid Sample 6-8 10 10 50.0 X liquid (Abbreviation explanation) *OD: 1,2-Octanediol, PG: 1,2-Propylene Glycol, BG: 1,3-Butylene Glycol
*BP: 1:1 mixture of BG and PG (wt%)

Referring to Table 6, it can be seen that liquefaction proceeds at a mixing ratio of 10:2, and is observed in a liquid state from the case of Samples 6-6.

Example 7: Preparation of a composition for lowering the freezing point using alkaline diol, ethylhexyl glycerin and 1,2-propylene glycol

As a solvent, various samples were prepared by mixing and dissolving 1,2-octanediol (OD), ethylhexylglycerin and 1,2-propylene glycol in a weight ratio of 10:0 to 10, and after 2 days at 4°C, they were subjected to subsequent tests. used in the example.

Test Example 7: Freezing point drop test

The sample composition prepared in Example 7 was subjected to a freezing point drop test at 4° C. for 2 days, and the results are shown in Table 7. Table 7 is a result showing whether a solid material is formed after 2 days at 4°C.

Sample name OD(g) EHG+PG(g) Concentration (wt%) solid matter
Formation note Sample 7-0 10 0 0 O solidification Sample 7-0.5 10 0.5 4.7 O solidification Sample 7-1 10 One 9.1 △ solid + liquid Sample 7-2 10 2 16.7 △ solid + liquid Sample 7-3 10 3 23.1 △ solid + liquid Sample 7-4 10 4 28.6 X liquid Sample 7-5 10 5 33.3 X liquid Sample 7-6 10 6.8 40.5 X liquid Sample 7-7 10 10 50.0 X liquid (Abbreviation explanation) *OD: 1,2-Octanediol, EHG: Ethyl Hexyl Glycerine,
PG: 1,2-Propylene Glycol
*EHG+PG: 1:1 mixture of EHG and PG (wt%)

As shown in Table 7, the blend of 1,2-octanediol, ethylhexylglycerin, and 1,2-propylene glycol according to Example 7 of the present invention is liquefied at a ratio of 10:1, and 10:4~ It can be seen that no precipitate is formed at a ratio of 10.

Test Example 8: Freezing point drop test

The sample composition prepared using 1,2-propylene glycol in Example 1 was subjected to a freezing point drop test at 10° C. for 2 days, and the results are shown in Table 8. Table 8 is a result showing whether a solid material is formed after 2 days at 10 °C.

Sample name OD(g) PG(g) PG concentration (wt%) solid matter
Formation note Sample 1-1 10 0 0 O solidification Sample 1-1.5 10 0.5 4.7 O solidification Sample 1-2 10 One 9.1 △ solid + liquid Sample 1-3 10 2 16.7 △ solid + liquid Sample 1-4 10 3 23.1 X liquid Samples 1-5 10 4 28.6 X liquid Samples 1-6 10 5 33.3 X liquid Sample 1-7 10 6.8 40.5 X liquid Samples 1-8 10 10 50.0 X liquid (Abbreviation explanation) *OD: 1,2-Octanediol, PG: 1,2-Propylene Glycol

As shown in Table 8, the mixture of 1,2-octanediol and propylene glycol according to Example 1 of the present invention is liquefied at a ratio of 10: 1 after 2 days at 10 ° C., 10: 3 ~ It can be seen that no precipitate is formed at a ratio of 10.

Test Example 9: Freezing point drop test

The melting point was compared for the freezing point lowering composition of various concentrations prepared using 1,3-butylene glycol in Example 2, and the results are shown in Table 9 below. Table 9 is a result showing whether a solid material is formed after 2 days at 10 °C. 2 is a photograph of this.

Sample name OD(g) BG(g) BG concentration
(wt%) solid matter
Formation note Sample 2-1 10 0 0 O solidification Sample 2-1.5 10 0.5 4.7 O solidification Sample 2-2 10 One 9.1 △ solid + liquid Sample 2-3 10 2 16.7 △ solid + liquid Sample 2-4 10 3 23.1 X liquid Sample 2-5 10 4 28.6 X liquid Sample 2-6 10 5 33.3 X liquid Sample 2-7 10 6.8 40.5 X liquid Sample 2-8 10 10 50.0 X liquid (Abbreviation explanation) *OD: 1,2-Octanediol, BG: 1,3-Butylene Glycol

As shown in Table 9, the mixture of 1,2-octanediol and 1,3-butylene glycol according to Example 2 of the present invention starts liquefaction at a ratio of 10:1 after 2 days at 10°C, It can be seen that precipitates are not formed at a ratio of 10:3 to 10.

Test Example 10: Freezing point drop test

The melting point was compared for the freezing point lowering composition of various concentrations prepared using ethanol in Example 3, and the results are shown in Table 10 below. Table 10 is a result showing whether a solid material is formed after 2 days at 10 °C. 3 is a photograph of this.

Sample name OD EtOH (g) EtOH concentration (wt%) solid matter
Formation note additive-free 10 0 0 O solid content Sample 3-1 10 0.5 4.7 △ solid + liquid Sample 3-2 10 One 9.1 △ solid + liquid Sample 3-3 10 2 16.7 X liquid Sample 3-4 10 3 23.1 X liquid Sample 3-5 10 4 28.6 X liquid Sample 3-6 10 5 33.3 X liquid Sample 3-7 10 6.8 40.5 X liquid Sample 3-8 10 10 50 X liquid (Abbreviation explanation) *OD: 1,2-Octanediol, EtOH: Ethyl Alcohol

From the results in Table 10, when ethanol is added to 1,2-octanediol, liquefaction starts at a ratio of 10:0.5, and a liquid phase is formed even when a small amount of ethanol (10:2 mixing ratio) is added. it can be confirmed that

Test Example 11: Freezing point drop test

In Example 6, the melting point was compared for the freezing point lowering composition of various concentrations prepared using a 1:1 mixture (BP) of propylene glycol and 1,3-butylene glycol, and the results are shown in the following table. 11 is shown. Table 11 is a result showing whether a solid material is formed after 2 days at 10 °C. 4 is a photograph of the result.

Sample name OD(g) BP
(BG/PG)(g) BP
density(%) solid matter
Formation note Sample 6-1 10 0 0 O solidification Sample 6-1.5 10 0.5 4.7 O solidification Sample 6-2 10 One 9.1 △ solid + liquid Sample 6-3 10 2 16.7 △ solid + liquid Sample 6-4 10 3 23.1 X liquid Sample 6-5 10 4 28.6 X liquid Sample 6-6 10 5 33.3 X liquid Sample 6-7 10 6.8 40.5 X liquid Sample 6-8 10 10 50.0 X liquid (Abbreviation explanation) *OD: 1,2-Octanediol, PG: 1,2-Propylene Glycol, BG: 1,3-Butylene Glycol
*BP: 1:1 mixture of BG and PG (wt%)

Referring to Table 11, it can be seen that liquefaction starts at a ratio of 10: 1 after 2 days at 10° C. and is observed in a liquid state at a ratio of 10: 3.

Test Example 12: Freezing point drop test

The sample composition prepared in Example 7 was subjected to a freezing point drop test at 10° C. for 2 days, and the results are shown in Table 12. Table 12 is a result showing whether a solid material is formed after 2 days at 10 °C.

Sample name OD(g) EHG +PG(g) Concentration (wt%) solid matter
Formation note Sample 7-0 10 0 0 O solidification Sample 7-0.5 10 0.5 4.7 O solidification Sample 7-1 10 One 9.1 △ solid + liquid Sample 7-2 10 2 16.7 △ solid + liquid Sample 7-3 10 3 23.1 X liquid Sample 7-4 10 4 28.6 X liquid Sample 7-5 10 5 33.3 X liquid Sample 7-6 10 6.8 40.5 X liquid Sample 7-7 10 10 50.0 X liquid (Abbreviation explanation) *OD: 1,2-Octanediol, EHG: Ethyl Hexyl Glycerine, PG: 1,2-Propylene Glycol
*EHG+PG: 1:1 mixture of EHG and PG (wt%)

As shown in Table 12, the combination of 1,2-octanediol, ethylhexylglycerin and 1,2-propylene glycol according to Example 7 of the present invention was liquefied at a ratio of 10:1 after 2 days at 10°C. It can be seen that the precipitate is not formed at a ratio of 10:3 to 10.

Example 8: Preparation of a composition for lowering the freezing point using an alkalidiol and a complex component

As a solvent, various samples were prepared by mixing and dissolving 1,2-octanediol (OD) and the complex component in a weight ratio of 10:0 to 10, and after 2 days at 10° C., these were used in subsequent test examples.

Test Example 13: Freezing point drop test

The sample composition prepared in Example 8 was subjected to a freezing point drop test at 10° C. for 2 days, and the results are shown in Table 13. Table 13 is a result showing whether a solid material is formed after 2 days at 10 °C.

Sample name OD(g) CP(g) CP concentration (wt%) solid matter
Formation note Sample 8-1 10 0 0 O solidification Sample 8-1.5 10 0.5 4.7 O solidification Sample 8-2 10 One 9.1 △ solid + liquid Sample 8-3 10 2 16.7 △ solid + liquid Sample 8-4 10 3 23.1 X liquid Sample 8-5 10 4 28.6 X liquid Sample 8-6 10 5 33.3 X liquid Sample 8-7 10 6.8 40.5 X liquid Sample 8-8 10 10 50.0 X liquid (Abbreviation explanation) *OD: 1,2-Octanediol, CP (Complex as listed belows): 1,2-Propanediol+1,3-Propanediol+2-Methyl-1,3-propanediol+1,2-Butanediol+1,3-Butanediol Equal amount mixture of +Ethylhexylglycerine + EtOH

As shown in Table 13, in the mixing of 1,2-octanediol and the complex component according to Example 8 of the present invention, liquefaction was started at a mixing ratio of 10:1, and precipitates were not formed at a mixing ratio of 10:3 to 10. it can be seen that

Test Example 14: Freezing point drop test

The melting point was compared for the freezing point lowering composition of various concentrations prepared in Example 1, and the results are shown in Table 14 below. Table 14 is a result showing whether a solid material is formed after 2 days at 25 ~ 27 ℃.

Sample name OD(g) PG(g) PG
density(%) solid matter
Formation note Sample 1-1 10 0 0 O solid content Sample 1-1.5 10 0.5 4.7 △ solid + liquid Sample 1-2 10 One 9.1 X liquid Sample 1-3 10 2 16.7 X liquid Sample 1-4 10 3 23.1 X liquid Samples 1-5 10 4 28.6 X liquid Samples 1-6 10 5 33.3 X liquid Sample 1-7 10 6.8 40.5 X liquid Samples 1-8 10 10 50.0 X liquid (Abbreviation explanation) *OD: 1,2-Octanediol, PG: 1,2-Propylene Glycol

As shown in Table 14, it can be confirmed that even when a small amount of 1,2-propylene glycol is added to 1,2-octanediol under the conditions of 25 to 27 ° C, which can be called room temperature, it is formed in a liquid phase. .

Likewise, it can be seen that the mixture is maintained in a liquid state at a ratio of 10:1 even when 1,3-butylene glycol, ethanol or 50 wt% of 1,2-propylene glycol and 1,3-butylene glycol are each included. there was.

Test Example 15: Preservative force test

The preservative power of the freezing point lowering composition of various concentrations prepared in the above Examples was compared with the Korea Research Institute of Chemical Technology (KTR), and the results are shown in Table 15 below. Table 15 shows the test results for preservative power after 2 weeks at 10°C.

Sample name unit microbe MIC results
%(v/v) Test Methods Sample 1-1
Sample 3-3 %(v/v) E. coli ATCC 8739 0.195 CLSI M07-A10:2015 Sample 1-1.5
Sample 2-3 %(v/v) Staphylococcus aureus ATCC 6538 0.391 CLSI M07-A10:2015 Sample 2-2
Sample 3-3 %(v/v) Pseudomonas aeruginosa ATCC 9027 0.0.391 CLSI M07-A10:2015 Sample 3-2
Sample 4-3 %(v/v) Candida albicans ATCC 10231 0.156 CLSI M27-A3:2008 Sample 4-2
Sample 5-3 %(v/v) Aspergillus brasiliensis ATCC16404 0.078 CLSI M38-A2:2008

From the above test results, the minimum concentration that inhibits the growth of 5 types of bacteria, that is, the MIC (minium inhibitory concentration) test value, compared to 100% of octanediol, the test results applied to samples of various concentrations were the same. It was confirmed to have the same preservative power, and it was confirmed that the preservative power was maintained at the same level as that of octanediol even when the composition of the present invention was included in a trace amount.

The physical properties of the materials used in Examples and Test Examples are shown in Table 16 below.

substance type Molecular Weight M.P. Remarks (experimental use products) 1,2-Octandiol 146.23g 36-38℃ Daedal Industrial: 99.0% 1,2-Propylene Glycol 76.1g -59.0℃ Duksan E-Chem: 99.0% EtOH 46.04g -114.0℃ Duksan E-Chem: 94% 1,3-Butylene Glycol 90.12g -57.0℃ US OXA; 99.5% 1,3-Propane Diol 76.1g -27.0℃ Duksan E-Chem: 99.0% Ethylhexyl Glycerine 204.3g -76.0℃ India Jeevan chemical: 99% 2-Methyl-1,3-propanediol 90.12g -91.0℃ Duksan E-Chem: 99.0% 1,2-Butanediol 90.12g -50.0℃ TCI reagent: 98.0%

Although the present invention has been shown and described with reference to specific embodiments, it is within the art that the present invention can be variously improved and changed without departing from the spirit of the present invention provided by the following claims. It will be obvious to those of ordinary skill in the art.

Claims (7)

alkanediol; And a hydrocarbon-based material comprising a hydroxyl group; Consisting of, liquefaction begins at 4 ° C. or higher, or forms a uniform liquid phase,
The alkanediol is 1,2-octanediol or 1,2-decanediol,
The hydrocarbon-based material including the hydroxyl group is 1,2-propanediol, 1,3-propanediol, 2-methyl-1,3-propanediol (MPO), 1,2-butanediol, 1,3-butanediol, At least one selected from the group consisting of ethylhexylglycerin, ethanol, and mixtures thereof,
The mixing ratio of the alkanediol and the hydrocarbon-based material containing a hydroxyl group is 10:2-10 by weight,
However, the material containing the hydroxyl group is at least one selected from the group consisting of 1,2-propanediol, 1,3-butanediol and ethanol, and the mixing ratio of the alkanediol and the hydrocarbon-based material containing the hydroxyl group is based on the weight. 10: 5 to 10, and the material including the hydroxyl group is at least one selected from the group consisting of 1,2-propanediol, 1,3-butanediol, 1,3-propanediol and ethanol; The freezing point lowering preservative composition for cosmetics, characterized in that the case where the mixing ratio of the alkanediol and the hydrocarbon-based material containing a hydroxyl group is in the range of 10:2 to 10 by weight. The method according to claim 1,
The alkanediol is a freezing point lowering antiseptic composition for cosmetics, characterized in that it performs the function of a preservative, a moisturizer or a lubricant. delete (a) mixing a liquid alkanediol and a hydrocarbon-based material containing a hydroxyl group to prepare a homogeneous liquid mixture; and
(b) maintaining the liquid mixture of the homogeneous phase in a liquid state;
The alkanediol is 1,2-octanediol or 1,2-decanediol,
The hydrocarbon-based material including the hydroxyl group is 1,2-propanediol, 1,3-propanediol, 2-methyl-1,3-propanediol (MPO), 1,2-butanediol, 1,3-butanediol, At least one selected from the group consisting of ethylhexylglycerin, ethanol, and mixtures thereof,
The mixing ratio of the alkanediol and the hydrocarbon-based material containing a hydroxyl group is 10:2-10 by weight,
However, the material containing the hydroxyl group is at least one selected from the group consisting of 1,2-propanediol, 1,3-butanediol and ethanol, and the mixing ratio of the alkanediol and the hydrocarbon-based material containing the hydroxyl group is based on the weight. 10: 5 to 10, and the material including the hydroxyl group is at least one selected from the group consisting of 1,2-propanediol, 1,3-butanediol, 1,3-propanediol and ethanol; A method for producing a freezing point lowering preservative composition for cosmetics, wherein the mixing ratio of the alkanediol and the hydrocarbon-based material containing a hydroxyl group is excluded from the range of 10:2 to 10 by weight. 5. The method according to claim 4,
When the alkanediol is in a solid state prior to step (a), heating it to liquefy the alkanediol. An external composition comprising the freezing point lowering antiseptic composition according to claim 1 as a main component of a preservative, a moisturizer, or a lubricant. 7. The method of claim 6,
The composition for external application is a composition for external application, characterized in that it is a basic cosmetic, makeup cosmetic, hair cosmetic, ointment, personal care product or home care product.

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