Compound and molded body containing same

Abstract

The present specification relates to a compound represented by Chemical Formula 1, which is soluble in at least two of ether, toluene, and ethyl acetate at room temperature, and a molded article containing the compound.

Description

[Technical field]

[0001] The present specification relates to a compound and a molded body comprising the same.

[0002] This application claims the benefit of the filing date of Korean Patent Application No. 10-2022-0131730 filed with the Korean Intellectual Property Office on October 13, 2022, and Korean Patent Application No. 10-2023-0136265 filed with the Korean Intellectual Property Office on October 12, 2023, the entire contents of which are incorporated herein by reference. [Background technology]

[0003] In recent years, there has been a demand for high antibacterial properties in a variety of products, including household goods and hygiene products.

[0004] The required level of antibacterial properties and the requirements for materials to provide antibacterial properties vary depending on the material of the product for which antibacterial properties are required and the final state of use. For example, the nature of the material to provide antibacterial properties and the level of antibacterial properties vary depending on the amount of antibacterial material applied to the product and the materials used together.

[0005] However, when introducing antibacterial agents that inhibit bacterial growth into resins, it is not easy to select and introduce antibacterial components that exhibit excellent bacterial growth inhibition properties, are harmless to the human body, are economical, and do not deteriorate the basic physical properties of the polymer resin.

[0006] For example, most of the widely used quaternary ammonium antibacterial agents are substituted with halogen anions, but in this case, there is a problem that they are only soluble in certain solvents, reducing their practicality, and there is also a problem that consumers have a negative perception of antibacterial agents containing halogens.

[0007] Therefore, there is a need to develop a material that is soluble in various solvents, exhibits high antibacterial properties, does not release antibacterial substances, and is harmless to the human body. [Prior art documents] [Patent documents]

[0008] [Patent Document 1] Korean Patent Publication No. 10-2009-0131847 Summary of the Invention [Problem to be solved by the invention]

[0009] The present specification provides a compound and a molded article containing the same. [Means for solving the problem]

[0010] One embodiment of the present specification is represented by the following chemical formula 1: Provided is a compound that is soluble in at least two of ether, toluene, and ethyl acetate at room temperature.

[0011] [ka]

[0012] In the above Chemical Formula 1, L1 is an alkylene group; R1 to R3 are the same or different and each independently represents an alkyl group, and at least one of R1 to R3 is an alkyl group having 5 to 30 carbon atoms; R4 is hydrogen or an alkyl group; R - is a salicylate-based anion, a sulfate-based anion, a bisulfate-based anion, a benzoate-based anion, a sorbate-based anion, or a lactate-based anion.

[0013] Another embodiment herein provides an antibacterial composition comprising the aforementioned compound.

[0014] Another embodiment herein provides a molded body comprising or made from the compound described above. Effect of the Invention

[0015] The compounds according to some embodiments herein can be dissolved in a variety of solvents.

[0016] The compounds according to some embodiments of the present invention have both hydrophilic and hydrophobic properties and have excellent antibacterial properties.

[0017] Compounds according to some embodiments herein can address safety concerns due to antibacterial spillage.

[0018] Compounds according to some embodiments herein can exert antibacterial properties within a short period of time.

[0019] The compounds according to some embodiments of the present specification have little change in antibacterial activity depending on the amount of antibacterial material used, so that even if the concentration of the compound is unintentionally varied when applied to a product, the compound can exhibit antibacterial activity within a predicted range. Therefore, the antibacterial activity can be controlled within a specific range, and antibacterial activity with excellent safety can be imparted.

[0020] The compounds according to some embodiments of the present invention have low toxicity, which can solve the safety issue. [Brief description of the drawings]

[0021] [Figure 1] FIG. 1 shows the results of NMR measurement of compound 12 in which R- is Br-. [Diagram 2] FIG. 1 shows the results of NMR measurement of compound 13 in which R- is Br-. [Diagram 3] The NMR measurement results of compound 13, in which R- is salicylate, are shown. [Figure 4] FIG. 1 shows the results of NMR measurement of compound 13 in which R- is citrate. [Diagram 5] FIG. 1 shows the results of NMR measurement of compound 13 in which R- is a sorbate. [Figure 6]FIG. 1 shows the NMR measurement results of compound 13 in which R- is benzoate. [Figure 7] FIG. 1 shows the results of NMR measurement of compound 12 in which R- is sulfate. [Figure 8] FIG. 1 shows the results of NMR measurement of compound 12 in which R- is bisulfate. [Figure 9] FIG. 1 shows the results of TGA measurement. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0022] This specification will be explained in detail below.

[0023] One embodiment of the present specification is represented by the following chemical formula 1: A compound is provided which is soluble in at least two of ether, toluene and ethyl acetate at room temperature.

[0024] [ka]

[0025] In the above Chemical Formula 1, L1 is an alkylene group; R1 to R3 are the same or different and each independently represents an alkyl group, and at least one of R1 to R3 is an alkyl group having 5 to 30 carbon atoms; R4 is hydrogen or an alkyl group; R - is a salicylate-based anion, a sulfate-based anion, a bisulfate-based anion, a benzoate-based anion, a sorbate-based anion, or a lactate-based anion.

[0026] Conventionally, quaternary ammonium antibacterial agents have been used in the form of quaternary ammonium substituted with a halogen anion. However, in this case, there is a problem that it dissolves only in certain solvents, reducing its practicality. Specifically, the halogen anion (F - , Cl - , Br- or I - ) is substituted with a quaternary ammonium compound, particularly represented by the above formula 1, - Compounds in which the halogen anion is a halogen anion dissolve only in specific solvents such as ethanol, methylene chloride, and acetone, but not in ether, toluene, and ethyl acetate, etc., and therefore have limitations in the fields of application, and have the problem of being unable to be used in lacquer-based paints, synthetic resin paints, acrylic paints, etc. In addition, there is a trend for authorities to tighten regulations on antibacterial agents containing halogens due to issues such as toxicity, the possibility of inducing environmental pollution, and handling issues due to high reactivity, and there is also the problem of negative perception from consumers.

[0027] Meanwhile, the compound according to the present specification does not contain a halogen group, but contains other specific anions, and thus can be dissolved in various solvents, which has the advantage of improving practicality. Specifically, the compound represented by Chemical Formula 1 according to the present specification shows the effect of dissolving in various solvents that could not be dissolved when using halogen anions, by changing the anion to a type other than halogen anion. Therefore, by selectively using a solvent as needed, the compound shows the effect of diversifying the application field.

[0028] In this specification, when a part is said to "comprise" a certain component, this means that it may further include other components, rather than excluding other components, unless specifically stated to the contrary.

[0029] In this specification, among physical properties, those that are affected by temperature are physical properties measured at room temperature, unless otherwise specified.

[0030] In this specification, "room temperature" refers to a natural temperature that is neither heated nor cooled, and means, for example, any temperature within a range of about 10° C. to 30° C., such as about 15° C., about 18° C., about 20° C., about 23° C., or about 25° C. Unless otherwise specified in this specification, the unit of temperature is ° C.

[0031] In this specification, when pressure affects the results of a physical property, the physical property is measured at normal pressure unless otherwise specified.

[0032] In this specification, "normal pressure" refers to the natural pressure that is neither increased nor decreased, and generally refers to approximately 1 atmosphere (approximately 700 to 800 mmHg).

[0033] In this specification, when humidity affects the results of a physical property, the physical property is measured at room temperature and pressure at unadjusted humidity, unless otherwise specified.

[0034] In the present specification, the "alkyl group" may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. In one embodiment of the present specification, the number of carbon atoms of the alkyl group is 1 to 30. Specific examples of the alkyl group include, but are not limited to, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, and a tridecyl group.

[0035] In this specification, the term "alkylene group" refers to an alkyl group having two bonding positions, i.e., a divalent group. The above description of the alkyl group can be applied to these groups, except that they are both divalent groups.

[0036] In this specification, the "aryl group" may be monocyclic or polycyclic, and the number of carbon atoms is not particularly limited, but is preferably 6 to 30. Specific examples of the aryl group include, but are not limited to, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, and a triphenyl group.

[0037] In this specification, "dissolved" means that the solubility measured by the following method 2 is 3 g / L or more.

[0038] [Method 2] 0.2g of the measurement target is taken and the solvent is added so that the total weight becomes 6.6g. After stirring at 25℃ for 30 minutes, the insoluble residual solute is removed. The amount of the removed residual solute is measured, and the amount of solute dissolved in the solvent is measured, and the measured amount is converted to a value for 1L of solvent to evaluate the solubility. In the above, the removal of the residual solute is performed by filtering the solution with a pore size of 0.45μm.

[0039] In one embodiment herein, the compound is dissolved in two of ether, toluene, and ethyl acetate at room temperature.

[0040] In one embodiment herein, the compound is dissolved in all three of ether, toluene, and ethyl acetate at room temperature.

[0041] In one embodiment of the present specification, the compound has a solubility in ether at room temperature of 3 g / L or more. Specifically, the solubility is 5 g / L or more, or 10 g / L or more. The upper limit of the solubility is not particularly limited, and for example, the solubility is 100 g / L or less, 90 g / L or less, or 80 g / L or less.

[0042] In one embodiment of the present specification, the compound has a solubility in toluene at room temperature of 3 g / L or more. Specifically, the solubility is 5 g / L or more, or 10 g / L or more. The upper limit of the solubility is not particularly limited, and for example, the solubility is 100 g / L or less, 90 g / L or less, or 80 g / L or less.

[0043] In one embodiment of the present specification, the compound has a solubility in ethyl acetate at room temperature of 3 g / L or more. Specifically, the solubility is 5 g / L or more, or 10 g / L or more. The upper limit of the solubility is not particularly limited, and for example, the solubility is 100 g / L or less, 90 g / L or less, or 80 g / L or less.

[0044] In this specification, the solubility being 3 g / L or more means that 3 g or more of the compound is dissolved in 1 L of the solvent.

[0045] In one embodiment herein, the compound is also soluble in ethanol, methylene chloride and acetone (ACT) at room temperature.

[0046] In one embodiment of the present specification, L1 is an alkylene group having 1 to 10 carbon atoms.

[0047] In one embodiment of the present specification, L1 is an alkylene group having 1 to 5 carbon atoms.

[0048] In one embodiment of the present specification, L1 is a methylene group; an ethylene group; a propylene group; or a butylene group.

[0049] In one embodiment of the present specification, any one of R1 to R3 is an alkyl group having 5 to 30 carbon atoms, and the rest are the same or different and each independently an alkyl group having 1 to 30 carbon atoms.

[0050] In one embodiment of the present specification, any one of R1 to R3 is an alkyl group having 5 to 30 carbon atoms, and the rest are the same or different and each independently an alkyl group having 1 to 20 carbon atoms.

[0051] In one embodiment of the present specification, any one of R1 to R3 is an alkyl group having 5 to 30 carbon atoms, and the rest are the same or different and each independently an alkyl group having 1 to 10 carbon atoms.

[0052] In one embodiment of the present specification, L1 is an alkylene group having 1 to 10 carbon atoms, any one of R1 to R3 is an alkyl group having 5 to 30 carbon atoms, and the remainder of R1 to R3 are the same or different and each independently an alkyl group having 1 to 30 carbon atoms.

[0053] In one embodiment of the present specification, L1 is an alkylene group having 1 to 5 carbon atoms, any one of R1 to R3 is an alkyl group having 5 to 30 carbon atoms, and the remainder of R1 to R3 are the same or different and each independently an alkyl group having 1 to 30 carbon atoms.

[0054] In one embodiment of the present specification, L1 is a methylene group, an ethylene group, or a butylene group, any one of R1 to R3 is an alkyl group having 5 to 30 carbon atoms, and the remainder of R1 to R3 are the same or different and each independently an alkyl group having 1 to 30 carbon atoms.

[0055] In one embodiment of the present specification, two or more of R1 to R3 are alkyl groups having 6 to 30 carbon atoms, or the difference in carbon number between the alkyl group with the largest carbon number and the alkyl group with the smallest carbon number among R1 to R3 is 4 or more.

[0056] Specifically, three of R1 to R3 are alkyl groups having 6 to 30 carbon atoms; two of R1 to R3 are alkyl groups having 6 to 30 carbon atoms and the remaining one is an alkyl group having 1 to 30 carbon atoms; or the difference in carbon number between the alkyl group with the largest carbon number and the alkyl group with the smallest carbon number among R1 to R3 is 4 or more. In this case, excellent antibacterial effect is exhibited.

[0057] In one embodiment of the present specification, the difference in carbon number between the alkyl group with the largest carbon number and the alkyl group with the smallest carbon number being 4 or more means that asymmetry is high, and the difference in carbon number may be 4 to 30, 5 to 30, or 5 to 10.

[0058] In one embodiment of the present specification, the compound has any one of the following structures:

[0059] [ka]

[0060] In the above structure, R - is as mentioned above.

[0061] In one embodiment of the present specification, the salicylate-based anion is

[0062] [ka]

[0063] where R10 is a hydrogen atom; an alkyl group; or an aryl group; and r10 is an integer of 1 to 4.

[0064] In one embodiment of the present specification, R - When is a salicylate anion, the compound exhibits solid properties.

[0065] In one embodiment of the present specification, R10 is hydrogen.

[0066] In one embodiment of the present specification, the benzoate-based anion is

[0067] [ka]

[0068] where R11 is a hydrogen atom; an alkyl group; or an aryl group; and r11 is an integer of 1 to 5.

[0069] In one embodiment of the present specification, R - When is a benzoate-based anion, the compound exhibits liquid properties.

[0070] In one embodiment of the present specification, R11 is hydrogen.

[0071] In one embodiment of the present specification, the sorbate anion is

[0072] [ka]

[0073] It is expressed as:

[0074] In one embodiment of the present specification, R - When is a sorbate anion, the compound exhibits solid properties.

[0075] In one embodiment of the present specification, the lactate-based anion is

[0076] [ka]

[0077] It is expressed as:

[0078] In one embodiment of the present specification, R - When is a lactate-based anion, the compound exhibits solid properties.

[0079] In one embodiment of the present specification, the sulfate-based anion is

[0080] [ka]

[0081] and R12 is an alkyl group.

[0082] In one embodiment of the present specification, R - When is a sulfate-based anion, the compound exhibits solid properties.

[0083] In one embodiment of the present specification, the bisulfate-based anion is

[0084] [ka]

[0085] and R12 is hydrogen.

[0086] In one embodiment of the present specification, R - When is a bisulfate anion, the compound exhibits solid properties.

[0087] In the present specification, unless otherwise specified, the carbon number of the alkyl group refers to an alkyl group having 1 to 30 carbon atoms, and the carbon number of the aryl group refers to an aryl group having 6 to 30 carbon atoms, and the substituents thereof are well known in the art and are not particularly limited as long as they do not deviate from the intent of the present invention.

[0088] As mentioned above, the properties of the compound vary depending on the type of anion group. That is, in one embodiment of the present specification, the properties of the compound can be adjusted through anion substitution. Therefore, the compound according to one embodiment of the present specification exhibits the effect of diversifying the application field of the compound by selectively substituting the anion as necessary.

[0089] In one embodiment of the present specification, - is one of the following structures:

[0090] [ka]

[0091] In the above-mentioned configuration, R10 to R12 are the same or different and each independently represents a hydrogen atom; an alkyl group; or an aryl group. r10 is an integer of 1 to 4, and when r10 is 2 or more, two or more R10 are the same or different. r11 is an integer of 1 to 5, and when r11 is 2 or more, the two or more R11's are the same or different from each other.

[0092] In one embodiment of the present specification, the compound does not precipitate after a certain period of time and remains dissolved in the solvent, i.e., the compound exhibits dissolution stability.

[0093] In one embodiment herein, the compound has antibacterial properties.

[0094] In this specification, having antibacterial properties means that the antibacterial activity measured based on the following method 1, that is, the bacteriostatic reduction rate, is 90% or more.

[0095] In one embodiment of the present specification, the compound has a bacteriostatic reduction rate of 90% or more against at least one strain selected from the group consisting of gram-positive bacteria, gram-negative bacteria, and fungi, as measured by the following method 1.

[0096] [Method 1] 20mL of broth type medium (Nutrient broth, BD DIFCO., 8g / L) inoculated with 3000CFU / mL bacteria is transferred to a 50mL conical tube, and 0.005g, 0.01g, 0.015g or 0.020g of compound is added and vortexed. The thoroughly mixed solution is cultured for 16 hours in a shaking water bath maintained at 35℃. The cultured solution is diluted 1 / 5 with 1x PBS buffer solution, and the absorbance at 600nm wavelength is measured using a UV / Vis spectrophotometer. The measured absorbance is compared with the solution cultured without bacteriostatic substance, and the bacteriostatic reduction rate is calculated using the following formula.

[0097]

number

[0098] In the present specification, the bacteriostatic substance of Formula 1 is a compound of Chemical Formula 1.

[0099] In this specification, CFU (Colony Forming Unit) means colony forming unit, and CFU / mL means the number of CFU per mL.

[0100] When the bacteriostatic reduction rate of the compounds of the present specification was evaluated by the above-mentioned method 1, the bacteriostatic reduction rate (antibacterial activity) was observed only in cases of 92% or more. As a result, it was confirmed that the compounds of the present specification have excellent antibacterial activity.

[0101] In this specification, gram-positive bacteria is a general term for bacteria that are stained purple when stained by the gram staining method. The cell walls of gram-positive bacteria are composed of multiple layers of peptidoglycan, and after staining with a basic dye such as crystal violet, the color does not fade and remains purple even when treated with ethanol.

[0102] In one embodiment of the present specification, the Gram-positive bacterium is selected from Enterococcus faecalis, Staphylococcus aureus, Streptococcus pneumoniae, Enterococcus faecium, and Lactobacillus lactis. Specifically, it is any one selected from the above examples, but is not limited thereto.

[0103] As used herein, gram-negative bacteria are a collective term for bacteria that stain red when stained with the gram staining method, and have a cell wall that has a relatively small amount of peptidoglycan compared to gram-positive bacteria, but instead have an outer membrane composed of lipid polysaccharides, lipid proteins and / or other complex polymeric substances.

[0104] In one embodiment of the present specification, the Gram-negative bacterium is selected from Proteus mirabilis, Escherichia coli, Salmonella typhi, Pseudomonas aeruginosa, and Vibrio cholerae. Specifically, the Gram-negative bacterium is any one selected from the above-mentioned examples, but is not limited thereto.

[0105] In one embodiment of the present specification, the fungus may be, but is not limited to, Candida albicans.

[0106] In one embodiment of the present specification, the compound has an antibacterial activity against Gram-positive bacteria of 90% or more as measured by the method 1 described above.

[0107] In one embodiment of the present specification, the compound has an antibacterial activity against Gram-negative bacteria of 90% or more as measured by the method 1 described above.

[0108] As the above mentioned gram positive, gram negative and fungal strains can cause various diseases upon contact as well as secondary infections, it is preferable to use one compound that is antibacterial against both the above mentioned gram positive, gram negative and fungal strains.

[0109] In one embodiment of the present specification, the compound has an acute oral toxicity concentration LD50 of more than 300 mg / Kg, preferably 320 mg / Kg or more. The higher the acute oral toxicity concentration LD50 of the compound according to the above embodiment, the lower the toxicity, which is advantageous. However, the value of LD50 can be determined from the viewpoint that the above-mentioned antibacterial activity must also be satisfied. For example, the acute oral toxicity concentration LD50 of the compound may be 50,000 mg / Kg or less, for example, 10,000 mg / Kg or less, 5,000 mg / Kg or less, or 2,000 mg / Kg or less. In one example, the acute oral toxicity concentration LD50 of the compound according to the above embodiment may be 1,000 mg / Kg or less.

[0110] One embodiment herein provides an antibacterial composition comprising the aforementioned compound.

[0111] In one embodiment herein, the aforementioned antimicrobial composition further comprises a solvent, said solvent being at least one of ether, toluene, ethyl acetate, acetone, water, acetonitrile, ethanol, dichloromethane, chloroform, and hexane.

[0112] In one embodiment of the present specification, the solvent contained in the antibacterial composition is 1 to 10 types, 1 to 7 types, 1 to 5 types, 1 to 3 types, or 1 type of the above-mentioned solvents.

[0113] In one embodiment of the present specification, the solvent contained in the antibacterial composition is one to three of ether, toluene, and ethyl acetate.

[0114] In one embodiment herein, the solvent contained in the antimicrobial composition is one of ether, toluene, and ethyl acetate.

[0115] One embodiment of the present specification provides a molded article containing or produced from the antibacterial resin. The molded article may be, but is not limited to, an automobile part, a blow molded article, an inflation molded article, a cast molded article, an extrusion laminate molded article, an extrusion molded article, a foam molded article, an injection molded article, a sheet, a film, a fiber, a monofilament, or a nonwoven fabric. The automobile part may be an interior or exterior material for an automobile. EXAMPLES

[0116] Hereinafter, the present specification will be described in detail with reference to examples in order to specifically explain the present specification. However, the embodiments of the present invention can be modified into various other forms, and the scope of the present specification is not to be construed as being limited to the examples described below. The examples of the present specification are provided to more completely explain the present specification to those having average knowledge in the art.

[0117] <Production Example 1> Production Example 1-1. Synthesis of Compound 1 Step 1. (1) 0.1 mol of 2-(dibutylamino)ethanol (DBAE), 0.1 mol of trimethylamine, and 0.001 mol of hydroquinone were added to 100 mL of THF (solvent). (2) While stirring the materials, 0.1 mol of methacryloyl chloride was added dropwise onto the reaction solution (at room temperature). (3) Stirred for 2 hours. (4) After removing the triethylamine salt by filtration, the solvent was removed using a rotary evaporator. (5) Vacuum dried at 83°C to 87°C.

[0118] Step 2. (1) The product of Step 1 and 1-bromooctane were dissolved in acrylonitrile (solvent) at a molar ratio of 1:1 at 50 wt %. (2) Next, p-methoxyphenol, a polymerization inhibitor, was added (ratio to reactants: 1:0.001 (eq)). (3) The reaction was carried out at 50°C for 20 hours. (4) The mixture was precipitated in methyl t-butyl ether (MTBE) (MTBE:reaction solution=15:1 (volume ratio)) and then filtered. (5) Vacuum dried at 45°C.

[0119] Step 3. (1) The product of step 2 was dissolved in water. (2) The salt was dissolved in water. (3) The two solutions prepared in (1) and (2) above were mixed and stirred overnight. (4) After the reaction was completed, the organic layer was extracted with ethyl acetate to produce compound 1.

[0120] The salt used in step 3 was sodium salicylate, sodium citrate, or sodium benzoate depending on the type of compound to be prepared.

[0121] Preparation Example 1-2. Synthesis of Compounds 2 and 3 Compounds 2 and 3 were prepared in the same manner as in Preparation Example 1-1, except that in step 2(1) of Preparation Example 1-1, 1-bromodecane (1-boromodecane, preparation of compound 2) or 1-bromododecane (1-boromododecane, preparation of compound 3) was used instead of 1-bromooctane.

[0122] Preparation Example 1-3. Synthesis of Compound 4 Compound 4 was prepared in the same manner as in Preparation Example 1-1, except that 2-(dioctylamino)ethanol (DOAE) was used instead of 2-(dibutylamino)ethanol in step 1(1) of Preparation Example 1-1.

[0123] Preparation Example 1-4. Synthesis of Compound 5 Step 1. (1) 0.1 mol of 2-(dihexylamino)ethanol (DHAE), 0.1 mol of trimethylamine, and 0.001 mol of hydroquinone were added to 100 mL of THF (solvent). (2) While stirring the materials, 0.1 mol of methacryloyl chloride was added dropwise onto the reaction solution (at room temperature). (3) Stirred for 2 hours. (4) After removing the triethylamine salt by filtration, the solvent was removed using a rotary evaporator. (5) Vacuum dried at 83°C to 87°C.

[0124] Step 2. (1) The product of Step 1 and 1-bromodecane were dissolved in acrylonitrile (solvent) at a molar ratio of 1:1 at 50 wt%. (2) Next, p-methoxyphenol, a polymerization inhibitor, was added (ratio to reactants: 1:0.001 (eq)). (3) The reaction was carried out at 50°C for 20 hours. (4) The mixture was precipitated in methyl t-butyl ether (MTBE) (MTBE:reaction solution=15:1 (volume ratio)) and then filtered. (5) Vacuum dried at 45°C.

[0125] Step 3. (1) The product of step 2 was dissolved in water. (2) The salt was dissolved in water. (3) The two solutions prepared in (1) and (2) above were mixed and stirred overnight. (4) After the reaction was completed, the organic layer was extracted with ethyl acetate to produce compound 1.

[0126] The salt used in step 3 was sodium salicylate, sodium citrate, or sodium benzoate depending on the type of compound to be prepared.

[0127] Preparation Example 1-5. Synthesis of Compound 6 Compound 6 was prepared in the same manner as in Preparation Example 1-4, except that 2-(butylhexylamino)ethanol (BHAE) was used instead of 2-(dihexylamino)ethanol in step 1(1) of Preparation Example 1-4.

[0128] Preparation Example 1-6. Synthesis of Compound 7 Compound 7 was prepared in the same manner as in Preparation Example 1-4, except that 2-(butyloctylamino)ethanol (BOAE) was used instead of 2-(dihexylamino)ethanol in step 1(1) of Preparation Example 1-4.

[0129] Preparation Example 1-7. Synthesis of Compound 8 Compound 8 was prepared in the same manner as in Preparation Example 1-4, except that 2-(butyldecylamino)ethanol (BOAE) was used instead of 2-(dihexylamino)ethanol in step 1(1) of Preparation Example 1-4.

[0130] Preparation Example 1-8. Synthesis of Compound 9 Compound 9 was prepared in the same manner as in Preparation Example 1-1, except that in step 1(1) of Preparation Example 1-1, 2-(dibutylamino)butanol (DBAB) was used instead of 2-(dibutylamino)ethanol.

[0131] Preparation Example 1-9. Synthesis of Compound 10 Compound 10 was prepared in the same manner as in Preparation Example 1-1, except that in step 1(1) of Preparation Example 1-1, 2-(dioctylamino)butanol (DOAB) was used instead of 2-(dibutylamino)ethanol.

[0132] Preparation Example 1-10. Synthesis of Compound 11 Step 1. (1) 5.3 g of 1-bromooctane, 3.7 g of 2-(dimethylamino)ethyl methacrylate, 89.4 mg of 4-methoxyphenol, and 12 mL of acetonitrile were placed in a two-neck round bottom flask (RBF). (2) The reaction was carried out at 60°C for 6 hours. (3) The mixture was precipitated in methyl t-butyl ether (MTBE) (MTBE: reaction solution = 15:1 (volume ratio)) and then filtered. (4) Vacuum dried at 45°C.

[0133] Step 2. (1) The product of step 1 was dissolved in water. (2) The salt to be replaced was dissolved in water. (3) The two solutions prepared in (1) and (2) above were mixed and stirred overnight. (4) After the reaction was completed, the organic layer was extracted with ethyl acetate to produce compound 1.

[0134] The salts used were sodium salicylate, sodium citrate, sodium benzoate, sodium sorbate, or sodium bisulfate depending on the type of compound to be prepared. However, when sodium dodecyl sulfate was used as the salt to be substituted, an excess amount of sodium chloride was added after the reaction in step 3(4) to extract the compound (salting out).

[0135] Preparation Example 1-11. Synthesis of Compounds 12 and 13 Compounds 12 and 13 were prepared in the same manner as in Preparation Example 1-10, except that 1-bromodecane (1-boromodecane, preparation of compound 12) or 1-bromododecane (1-boromododecane, preparation of compound 13) was used instead of 1-bromooctane in Preparation Example 1-10.

[0136] R - Br - Compounds 12 and 13 were obtained by terminating the reaction at step 1 of the above Production Examples 1-10 and 1-11.

[0137] In the above Preparation Examples 1-1 to 1-11, a static precipitation method was used in which the reactants were added to a nonsolvent, but a reverse precipitation method in which the nonsolvent is added to the reactants may also be used. In addition, the ratio of MTBE to the reaction solution may be other than 15:1, for example, 12:1 or 26:1.

[0138] The structures of compounds 1 to 13 produced in the above Production Examples 1-1 to 1-11 are as follows.

[0139] [ka]

[0140] [ka]

[0141] It was confirmed by NMR measurement that the compounds 1 to 13 substituted with specific anions were synthesized.

[0142] Figure 1 shows the R - Br - The NMR measurement result of compound 12 is shown below.

[0143] Figure 2 shows the R - Br - The NMR measurement results of compound 13 are shown below.

[0144] Figure 3 shows the R - The NMR measurement results of compound 13, which is a salicylate, are shown below.

[0145] Figure 4 shows the R - The NMR measurement results of compound 13, in which the compound is a citrate, are shown.

[0146] Figure 5 shows the R - The NMR measurement results of compound 13, which is a sorbate, are shown.

[0147] Figure 6 shows the R - The NMR measurement results of compound 13, in which the benzoate is

[0148] Figure 7 shows the R - The NMR measurement results of compound 12, in which the carbon atom is sulfate, are shown.

[0149] Figure 8 shows the R - The NMR measurement results of compound 12, in which the compound is a bisulfate, are shown.

[0150] <Experimental Example 1> Solubility measurement 0.2 g of the measurement target was collected, and the solvent was added so that the total weight became 6.6 g. After stirring at 25°C for 30 minutes, the insoluble residual solute was removed. The amount of the removed residual solute was measured, and the amount of the solute dissolved in the solvent was measured, and the measured amount was converted into a value for 1 L of the solvent to evaluate the solubility. In the above, the removal of the residual solute was performed by filtering the solution with a pore size of 0.45 μm.

[0151] The object of measurement is the compound 13 produced in the above Production Example 1-11. - According to the type, they are designated as shown in Table 1 below.

[0152] The solubility measurement results are shown in Table 1 below.

[0153] [Table 1]

[0154] From Table 1, the compound has a halogen group (specifically, Br - It can be seen that the inclusion of a specific anion other than citrate or citrate can improve the solubility in various solvents.

[0155] <Experimental Example 2> Antibacterial activity measurement 3000 CFU / mL E. coli was transferred to 20 mL of broth type medium (Nutrient broth, BD DIFCO., 8 g / L) in a 50 mL conical tube, and 0.005 g, 0.01 g, 0.015 g, or 0.020 g of compound was added and vortexed. The thoroughly mixed solution was cultured for 16 hours in a shaking incubator maintained at 35°C. The cultured solution was diluted 1 / 5 with 1x PBS buffer solution, and the absorbance at 600 nm wavelength was measured using a UV / Vis spectrophotometer. The measured absorbance was compared with the solution cultured without the bacteriostatic substance, and the bacteriostatic reduction rate was calculated using the following formula.

[0156] The object of measurement is the compound 13 produced in the above Production Example 1-11. - According to the type, they are named as shown in Table 2 below.

[0157]

number

[0158] The derived bacteriostatic reduction rates (antibacterial activities) are shown in Table 2 below.

[0159] [Table 2]

[0160] In Table 2 above, 0.5 phr, 1 phr, 1.5 phr and 2 phr are as follows:

[0161] -0.5phr: 0.005g of compound was added to 20mL of 3000CFU / mL bacterial solution. -1phr: 0.01g of compound was added to 20mL of 3000CFU / mL bacterial solution. -1.5phr: 0.015g of compound was added to 20mL of 3000CFU / mL bacterial solution. -2phr: 0.02g of compound was added to 20mL of 3000CFU / mL bacterial solution.

[0162] From Table 2, it can be seen that the compounds according to one embodiment of the present invention can be obtained by using specific anions, such as Br - It can be confirmed that the compound containing citrate exhibits the same or greater antibacterial activity as the compound containing citrate.

[0163] <Experimental Example 3> Toxicity and Stability Evaluation The acute oral toxicity concentration LD50 was measured according to the 3T3 Neutral Red Uptake (NRU) assay (OECD Guidance Document NO 129). Specifically, the LD50 was calculated as follows.

[0164]

number

[0165] The calculated results are shown in Table 3 below.

[0166] The object of measurement is the compound 13 produced in the above Production Example 1-11. - According to the type, they are named as shown in Table 3 below.

[0167] [Table 3]

[0168] From Table 3, it can be seen that the compound according to one embodiment of the present specification has an LD50 that falls within acute toxicity criteria category 4 (300 mg / kg to 2,000 mg / kg) similarly to the case where a halogen group is applied as an anion and the case where citrate is applied as an anion. Therefore, from Tables 1 to 3, it can be seen that the compound according to one embodiment of the present specification has an acute toxicity criteria of Br - and citrate, which belong to the same Category 4, have improved antibacterial activity and can dissolve in a variety of solvents.

[0169] <Experimental Example 4> Heat resistance evaluation In this experiment, the heat resistance evaluation was defined as the extrapolated intersection point (first pyrolysis temperature) between the initial mass reference line and the tangent line of the maximum gradient point in the first mass loss section of the mass loss curve measured by a thermogravimetric analyzer (TGA) in an N2 atmospheric environment.

[0170] In the present invention, when the first thermal decomposition temperature of the compound is higher than the first thermal decomposition temperature of the material before anion substitution, it is determined that the heat resistance is increased. The measurement results are shown in Figure 9 below.

[0171] The object of measurement is the compound 12 produced in the above Production Example 1-11. -The results are shown in FIG. 9 for Comparative Example 4-1 and Example 4-1 according to the type of the compound.

[0172] Referring to FIG. 9, the anion is Br - It can be confirmed that the Td (thermal decomposition temperature) of Comparative Example 4-1 is about 230° C., and the heat resistance is improved compared to Example 4-1 in which the anion is substituted with bisulfate.

Claims

1. Represented by the following chemical formula 1: A compound that is soluble in at least two of ether, toluene, and ethyl acetate at room temperature: 【Chemistry 1】 In the above Chemical Formula 1, L1 is an alkylene group; R1 to R3 are the same or different and each independently represent an alkyl group, and at least one of R1 to R3 represents an alkyl group having 5 to 30 carbon atoms; R4 is hydrogen or an alkyl group; R － is a salicylate-based anion, a sulfate-based anion, a bisulfate-based anion, a benzoate-based anion, a sorbate-based anion, or a lactate-based anion.

2. The R － is any one of the following structures: 【Chemistry 2】 In the above-mentioned configuration, R10 to R12 are the same or different and each independently represents a hydrogen atom; an alkyl group; or an aryl group; r10 is an integer of 1 to 4, and when r10 is 2 or more, two or more R10 are the same or different. r11 is an integer of 1 to 5, and when r11 is 2 or more, the two or more R11's are the same or different.

3. The compound according to claim 1, wherein any one of R1 to R3 is an alkyl group having 5 to 30 carbon atoms, and the rest are the same or different and each independently is an alkyl group having 1 to 30 carbon atoms.

4. The compound of claim 1 having one of the following structures: 【Chemistry 3】 In the above structure, R － is as defined in claim 1.

5. The compound according to claim 1, which has a bacteriostatic reduction rate of 90% or more against at least one strain selected from the group consisting of gram-positive bacteria, gram-negative bacteria and fungi, as measured by the following method 1: [Method 1] 20 mL of broth type medium (Nutrient broth, BD DIFCO., 8 g / L) inoculated with 3000 CFU / mL of bacteria was transferred to a 50 mL conical tube, and 0.005 g, 0.01 g, 0.015 g, or 0.020 g of a compound was added and vortexed. The well-mixed solution was cultured in a shaking incubator maintained at 35° C. for 16 hours. The solution after the completion of the incubation is diluted 1 / 5 with 1x PBS buffer solution, and the absorbance at 600 nm is measured using a UV / Vis spectrophotometer. The measured absorbance is compared with that of a solution incubated without a bacteriostatic substance, and the bacteriostatic reduction rate is calculated using the following formula. [0010]

6. 6. The compound according to claim 5, wherein the Gram-positive bacteria is selected from among Enterococcus faecalis, Staphylococcus aureus, Streptococcus pneumoniae, Enterococcus faecium and Lactobacillus lactis.

7. 6. The compound according to claim 5, wherein the Gram-negative bacteria is selected from among Proteus mirabilis, Escherichia coli, Salmonella typhi, Pseudomonas aeruginosa and Vibrio cholerae.

8. An antibacterial composition comprising a compound according to any one of claims 1 to 7.

9. The antimicrobial composition further comprises a solvent; 9. The antimicrobial composition of claim 8, wherein the solvent is at least one of ether, toluene, ethyl acetate, acetone, water, acetonitrile, ethanol, dichloromethane, chloroform, and hexane.

10. A molding comprising or produced from a compound according to any one of claims 1 to 7.

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