How to identify compounds and impurities contained in them

Abstract

The present invention relates to a method for identifying a compound and impurities contained therein.

Description

[Technical field]

[0001] This application claims the benefit of the filing date of Korean Patent Application No. 10-2022-0117306, filed with the Korean Intellectual Property Office on September 16, 2022, the entire contents of which are incorporated herein by reference.

[0002] The present invention relates to a method for identifying a compound and impurities contained therein. [Background technology]

[0003] In recent years, antibacterial properties have been required for 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, the antibacterial products contain unintended decomposition products or intermediate products that are not the intended target due to the high temperature process required during the manufacturing process, making it difficult to obtain a highly pure product.

[0006] Therefore, there is a need to develop a method for determining whether an antibacterial material suitable for application to various products contains decomposition products or impurities that are not the intended target. Summary of the Invention [Problem to be solved by the invention]

[0007] The present invention relates to a method for identifying a compound and impurities contained therein. [Means for solving the problem]

[0008] One embodiment of the present invention provides a compound comprising a quaternary ammonium structure having an acrylate or methacrylate group, the compound having a turbidity of less than 120 as derived by Method 1 below.

[0009] [Method 1] A 20 wt % aqueous solution of the compound is analyzed by UV / Vis spectroscopy to measure the absorbance Abs for light with a wavelength of 290 nm, and the turbidity Tb is calculated from the measured absorbance Abs using the following formula 1.

[0010] [Formula 1] Abs=0.00309Tb+0.04946

[0011] Another embodiment of the present invention provides a method for identifying impurities in a compound containing a quaternary ammonium structure having an acrylate group or a methacrylate group, the impurities being identified by at least one of the following methods 1' to 3':

[0012] [Method 1'] A 20 wt % aqueous solution of the compound is analyzed by UV / Vis spectroscopy to measure the absorbance Abs for light with a wavelength of 290 nm, and the turbidity Tb is calculated from the measured absorbance Abs using the following formula 1. If the calculated turbidity Tb is 120 or more, the presence of impurities is confirmed.

[0013] [Formula 1] Abs=0.00309Tb+0.04946

[0014] [Method 2'] The compound is dissolved in a mixed solution containing acetonitrile and water in a volume ratio of 5:5 and analyzed by HPLC / CAD. When a peak of 100 mV or more is detected at 4 to 9 minutes, the presence of impurities is confirmed.

[0015] [Method 3'] The compound is dissolved in DMF and analyzed by GPC / RI-DMF. When a peak of 10 mV or more is detected at 10 to 18 minutes, the presence of an impurity is confirmed. Effect of the Invention

[0016] Compounds according to some embodiments of the present invention have the advantage that they are free or substantially free of impurities.

[0017] The compounds according to some embodiments of the present invention have the advantage of having excellent antibacterial activity.

[0018] The method for checking impurities according to some embodiments of the present invention makes it easy to check whether a target impurity is present.

[0019] The method for checking impurities according to some embodiments of the present invention can be applied to quality control such as QC (Quality Control).

[0020] The method for identifying impurities according to some embodiments of the present invention has the advantage that it proceeds in a short period of time. [Brief description of the drawings]

[0021] [Figure 1] FIG. 1 shows UV / Vis measurements according to some embodiments of the present invention. [Diagram 2] FIG. 1 shows HPLC / CAD results according to some embodiments of the present invention. [Diagram 3] FIG. 1 shows HPLC / CAD results according to some embodiments of the present invention. [Figure 4] FIG. 2 shows the results of GPC / RI-DMF measurements according to some embodiments of the present invention. [Diagram 5] FIG. 2 shows the results of GPC / RI-DMF measurements according to some embodiments of the present invention. [Figure 6] FIG. 2 shows the results of GPC / RI-CHCl3 measurements according to some embodiments of the present invention. [Figure 7] FIG. 2 shows the results of GPC / RI-CHCl3 measurements according to some embodiments of the present invention. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0022] The present invention will be described in detail below.

[0023] One embodiment of the present invention provides a compound comprising a quaternary ammonium structure having an acrylate or methacrylate group, the compound having a turbidity of less than 120 as derived by Method 1 below.

[0024] [Method 1] A 20 wt % aqueous solution of the compound is analyzed by UV / Vis spectroscopy to measure the absorbance Abs for light with a wavelength of 290 nm, and the turbidity Tb is calculated from the measured absorbance Abs using the following formula 1.

[0025] [Formula 1] Abs=0.00309Tb+0.04946

[0026] According to one embodiment of the present specification, the formula 1 is derived via the following method A.

[0027] [Method A] Five types of turbidity standard solutions (0, 1, 10, 100, 1000 NTU each) are analyzed by UV / Vis spectroscopy (Agilent 8453, 200~1100nm, resolution 2nm, 1mm cuvette) to confirm the absorbance of light with a wavelength of 290nm. An empty cuvette cell is used as a reference for the measurement. A calibration curve (Equation 1) is derived from the absorbance in the range from 0 NTU to 1,000 NTU. (NTU: Nephelometric Turbidity Unit, water quality standard is 1 NTU)

[0028] According to one embodiment of the present invention, in the method 1, when the turbidity is 120 or more, it can be determined that a large amount of impurities is contained, and when the turbidity is 40 or more and less than 120, it can be determined that some impurities are contained. As an example, when the turbidity is 40 or more and less than 120, it can be determined that some impurities are contained in sample numbers 3 to 6 in the examples described later.

[0029] According to one embodiment of the present invention, the turbidity of the compound is less than 40. Preferably, when the turbidity Tb in the method 1 is less than 40, the absence of impurities can be confirmed. As an example, it can be determined that sample numbers 1 and 2 in the examples described below, which have a turbidity Tb of less than 40, have no or very few impurities.

[0030] On the other hand, when the turbidity Tb is 120 or more, it can be confirmed that the compound contains a very large amount of impurities. As an example, sample No. 7 in the examples described below, which has a turbidity Tb of 120 or more, can be determined to contain a very large amount of impurities.

[0031] According to one embodiment of the present invention, the lower limit of the turbidity of the compound is not limited and may be 0 or more.

[0032] According to one embodiment of the present invention, when the turbidity of the compound satisfies the requirement of less than 120, the antibacterial activity can be improved.

[0033] According to one embodiment of the present invention, in order to make the turbidity of the compound satisfy the above range, i.e., to reduce the concentration of impurities, the synthesis conditions of the compound can be adjusted, or purification can be performed during or after the synthesis.

[0034] Specifically, in order to reduce the impurity concentration, the synthesis may be carried out at a temperature of 20° C. to 80° C. for 3 to 30 hours during compound production. More specifically, the synthesis may be carried out at a temperature of 40° C. to 70° C. for 4 to 25 hours. More specifically, the synthesis may be carried out for 4 to 20 hours.

[0035] In order to reduce the impurity concentration, a polymerization inhibitor may be used in an amount of 0.001 to 0.05 equivalents, specifically 0.001 to 0.01 equivalents, per equivalent of a reactant during production of the compound.

[0036] In addition, in order to reduce the impurity concentration, the reaction solution and the precipitation solution may be used in a volume ratio of 1:1 to 1:30 (reaction solution:precipitation solution), specifically, a volume ratio of 1:3 to 1:20, during precipitation for producing a compound.

[0037] In one embodiment of the present invention, the polymerization inhibitor and the precipitating solution can be any material used in the art without any limitation.

[0038] According to one embodiment of the present invention, the impurity may be a polymer containing a compound containing a quaternary ammonium structure having an acrylate group or a methacrylate group and / or a polymer containing a unit derived from the compound containing a quaternary ammonium structure having an acrylate group or a methacrylate group. For example, the impurity may be a homopolymer of the compound.

[0039] According to one embodiment of the present invention, when the compound is subjected to the following method 2, no peak of 100 mV or more is detected within 4 to 9 minutes.

[0040] [Method 2] The compound is dissolved in a mixed solution containing acetonitrile and water in a volume ratio of 5:5, and analyzed by HPLC / CAD (High Performance Liquid Chromatography / Charged Aerosol Detector).

[0041] At this time, the method 2 may be carried out according to the following specific conditions.

[0042] -Column: Capcellpak CN, 4.6mmIDx150mmL, 5μm, Shiseido -First mobile phase: acetonitrile / trichloroacetic acid = 100 / 0.1 (v / v,%) - Second mobile phase: H2O / trichloroacetic acid = 100 / 0.1 (v / v,%) -Flow rate: 1mL / min -Injection volume: 5μL -Progress time: 15 minutes

[0043] According to one embodiment of the present invention, a sample in which 1 mg of a compound is dissolved in 1 mL of a mixed solution may be used in the method 2. That is, the method 2 is measured using a sample with a concentration of 1 mg / mL (compound / mixed solution).

[0044] According to one embodiment of the present invention, a compound containing a quaternary ammonium structure having an acrylate or methacrylate group that does not contain impurities does not have a peak of 100 mV or more at 4 to 9 minutes when subjected to the method 2. On the other hand, when impurities are mixed in, a peak of 100 mV or more is present at 4 to 9 minutes when subjected to the method 2. Based on this, when a peak of 100 mV or more is detected at 4 to 9 minutes when subjected to the method 2, it can be confirmed that the sample further contains impurities in addition to the compound containing a quaternary ammonium structure having an acrylate or methacrylate group.

[0045] According to one embodiment of the present invention, when impurities are present, a peak of 125 mV or more is detected at 4 to 9 minutes when the method 2 is used.

[0046] According to one embodiment of the present invention, when the compound is subjected to the method 2, no peak of 50 mV or more is detected between 4 minutes and 9 minutes.

[0047] According to one embodiment of the present invention, when the compound is subjected to the method 2, either no peak is detected between 4 and 9 minutes or a peak of less than 50 mV is detected.

[0048] According to one embodiment of the present invention, when the compound is subjected to the method 2, no peak of 100 mV or more is detected between 4 minutes and 12 minutes.

[0049] According to one embodiment of the present invention, when the compound is subjected to the method 2, a peak is detected at 1 to 3 minutes.

[0050] According to one embodiment of the present invention, when the compound is subjected to the method 2, a peak of 100 mV or more is detected within 1 to 3 minutes.

[0051] According to one embodiment of the present invention, when the compound is subjected to the method 2, peaks are detected at 1 minute to 3 minutes, and one or more of the detected peaks are at 100 mV to 5,000 mV.

[0052] In the present invention, the magnitude of a peak means the magnitude of the highest point of the peak. For example, a peak of 100 mV or more detected from 1 minute to 3 minutes means that the highest point of the peak present from 1 minute to 3 minutes is 100 mV or more.

[0053] According to one embodiment of the present invention, when the above method 2 is used, a compound in which no peak of 100 mV or more is detected between 4 and 9 minutes exhibits an effect of improving antibacterial activity.

[0054] According to one embodiment of the present invention, in order to prevent a peak of 100 mV or more from being detected at 4 to 9 minutes, i.e., to reduce the concentration of impurities, the synthesis conditions of the compound can be adjusted or purification can be performed during or after the synthesis process when using the method 2. The specific synthesis conditions for this purpose are the same as those described above for the method 1.

[0055] According to one embodiment of the present invention, when the compound is subjected to the following method 3, no peak of 10 mV or more is detected within 10 to 18 minutes.

[0056] [Method 3] The compound is dissolved in DMF and analyzed by GPC / RI-DMF (Gel Permeation Chromatography / Refractive Index-DMF).

[0057] At this time, the method 3 may be carried out according to the following specific conditions.

[0058] -Column: PLgel column -1st mobile phase: DMF / 0.01M LiBr -Flow rate: 1mL / min -Injection volume: 100μL -Progress time: 35 minutes

[0059] According to one embodiment of the present invention, a sample in which 5 mg of a compound is dissolved in 1 mL of DMF (dimethylformamide) can be used in the method 3. That is, the method 3 is measured using a sample with a concentration of 5 mg / mL (compound / mixed solution).

[0060] According to one embodiment of the present invention, a compound containing a quaternary ammonium structure having an acrylate or methacrylate group that does not contain impurities does not have a peak of 10 mV or more at 10 to 18 minutes when subjected to the method 3. On the other hand, when impurities are present, a peak of 10 mV or more is present at 10 to 18 minutes when subjected to the method 3. Based on this, when a peak of 10 mV or more is detected at 10 to 18 minutes when subjected to the method 3, it can be confirmed that the sample further contains impurities in addition to the compound containing a quaternary ammonium structure having an acrylate or methacrylate group.

[0061] According to one embodiment of the present invention, when the compound is subjected to Method 3, no peak of 5 mV or more is detected between 10 minutes and 18 minutes.

[0062] According to one embodiment of the present invention, when the compound is subjected to Method 3, no peak is detected between 10 minutes and 18 minutes.

[0063] According to one embodiment of the present invention, when a sample containing impurities is subjected to Method 3, a peak of 10 mV or more is detected in 10 to 18 minutes.

[0064] According to one embodiment of the present invention, the upper limit of the peak detected from a sample containing impurities is not limited, but may be, for example, 500 mV or less. For example, when a sample containing impurities is subjected to the method 3, a peak of 10 mV or more and 500 mV or less is detected in 10 to 18 minutes.

[0065] According to one embodiment of the present invention, in the method 3, a sample may be dissolved in DMF at a concentration of 5 mg / ml (sample / DMF), and then the sample may be shaken for about 10 to 14 hours, followed by measurement of GPC / RI-DMF.

[0066] According to one embodiment of the present invention, when the above method 3 is used, a compound in which no peak of 10 mV or more is detected between 10 and 18 minutes exhibits an effect of improving antibacterial activity.

[0067] According to one embodiment of the present invention, in order to prevent a peak of 10 mV or more from being detected at 10 to 18 minutes, i.e., to reduce the concentration of impurities, the synthesis conditions of the compound can be adjusted or purification can be performed during or after the synthesis in the method 3. The specific synthesis conditions for this purpose are the same as those described above in the method 1.

[0068] According to one embodiment of the present invention, the compound is represented by the following formula 1:

[0069] [ka]

[0070] In the above Chemical Formula 1, R1 to R3 are the same or different and each independently represents a hydrogen atom or a methyl group; R4 to R6 are the same or different and each independently represents an alkyl group; L is an alkylene group.

[0071] According to one embodiment of the present invention, R1 is hydrogen or a methyl group.

[0072] According to one embodiment of the present invention, R2 is hydrogen or a methyl group.

[0073] According to one embodiment of the present invention, R3 is hydrogen or a methyl group.

[0074] According to one embodiment of the present invention, R2 and R3 are hydrogen, and R1 is hydrogen or a methyl group.

[0075] According to one embodiment of the present invention, the L is an alkylene group having 1 to 30 carbon atoms.

[0076] According to one embodiment of the present invention, the L is an alkylene group having 1 to 10 carbon atoms.

[0077] According to one embodiment of the present invention, the L is an alkylene group having 1 to 5 carbon atoms.

[0078] According to one embodiment of the present invention, L is a methylene group, an ethylene group, a propylene group or a butylene group.

[0079] According to one embodiment of the present invention, the R2 and R3 are hydrogen, the R1 is hydrogen or a methyl group, and the L is an alkylene group having 1 to 30 carbon atoms.

[0080] According to one embodiment of the present invention, the R2 and R3 are hydrogen, the R1 is hydrogen or a methyl group, and the L is an alkylene group having 1 to 10 carbon atoms.

[0081] According to one embodiment of the present invention, R2 and R3 are hydrogen, R1 is hydrogen or a methyl group, and L is a methylene group, an ethylene group, a propylene group, or a butylene group.

[0082] According to one embodiment of the present invention, R4 to R6 are the same or different and each independently represents an alkyl group having 1 to 30 carbon atoms.

[0083] According to one embodiment of the present invention, any one of R4 to R6 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.

[0084] According to one embodiment of the present invention, any one of R4 to R6 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.

[0085] According to one embodiment of the present invention, any one of R4 to R6 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 15 carbon atoms.

[0086] According to one embodiment of the present invention, any one of R4 to R6 is an alkyl group having 5 to 20 carbon atoms, and the rest are the same or different and each independently an alkyl group having 1 to 30 carbon atoms.

[0087] According to one embodiment of the present invention, any one of R4 to R6 is an alkyl group having 5 to 20 carbon atoms, and the rest are the same or different and each independently an alkyl group having 1 to 20 carbon atoms.

[0088] According to one embodiment of the present invention, any one of R4 to R6 is an alkyl group having 5 to 20 carbon atoms, and the rest are the same or different and each independently an alkyl group having 1 to 10 carbon atoms.

[0089] According to one embodiment of the present invention, any one of R4 to R6 is an alkyl group having 5 to 20 carbon atoms, and the rest are the same or different and each independently an alkyl group having 1 to 4 carbon atoms.

[0090] According to one embodiment of the present invention, the R2 and R3 are hydrogen, the R1 is hydrogen or a methyl group, the L is an alkylene group having 1 to 30 carbon atoms, any of the R4 to R6 is an alkyl group having 5 to 30 carbon atoms, and the remainder of the R4 to R6 are the same or different and each independently is an alkyl group having 1 to 30 carbon atoms.

[0091] According to one embodiment of the present invention, the R2 and R3 are hydrogen, the R1 is hydrogen or a methyl group, the L is an alkylene group having 1 to 20 carbon atoms, any of the R4 to R6 is an alkyl group having 5 to 20 carbon atoms, and the remainder of the R4 to R6 are the same or different and each independently is an alkyl group having 1 to 20 carbon atoms.

[0092] According to one embodiment of the present invention, the R2 and R3 are hydrogen, the R1 is hydrogen or a methyl group, the L is an alkylene group having 1 to 10 carbon atoms, any of the R4 to R6 is an alkyl group having 5 to 20 carbon atoms, and the remainder of the R4 to R6 are the same or different and each independently an alkyl group having 1 to 15 carbon atoms.

[0093] According to one embodiment of the present invention, the compound is any one selected from the following compounds 1 to 10.

[0094] [ka] [ka]

[0095] According to one embodiment of the present invention, the compound containing a quaternary ammonium structure having an acrylate group or a methacrylate group exhibits cationicity, and may therefore exist in the form of a salt together with a group exhibiting anionicity. In this case, the group exhibiting anionicity is not particularly limited, and any material known in the art may be used as long as it does not impair the purpose of the antibacterial resin. For example, the group exhibiting anionicity may be a halogen-based anion or a sulfonate-based anion, and specifically, Br- may be, but is not limited to.

[0096] According to one embodiment of the invention, the compound is an antibacterial compound, i.e., the compound exhibits antibacterial properties.

[0097] In one embodiment of the present specification, the antimicrobial resin exhibits antimicrobial activity against at least one of gram-positive bacteria, gram-negative bacteria, and fungi.

[0098] In this specification, gram-positive bacteria is a general term for bacteria that stain purple when stained with 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.

[0099] In one embodiment of the present specification, the Gram-positive bacteria 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.

[0100] As used herein, gram-negative bacteria is a collective term for bacteria that stain red when stained with the gram staining method, and which, instead of having a cell wall with a relatively small amount of peptidoglycan compared to gram-positive bacteria, have an outer membrane composed of lipid polysaccharides, lipid proteins and / or other complex polymeric substances.

[0101] 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.

[0102] In one embodiment of the present invention, the fungus may be, but is not limited to, Candida albicans.

[0103] In this specification, showing antibacterial properties means that the antibacterial activity measured based on the following method 4, that is, the bacteriostatic reduction rate, is 90% or more.

[0104] According to one embodiment of the present specification, the antibacterial resin has an antibacterial activity of 90% or more against any strain selected from the group consisting of gram-positive bacteria, gram-negative bacteria, and fungi, as measured by the following method 4.

[0105] [Method 4] 1 g of sample was placed in a 250 mL Erlenmeyer flask, and 50 mL of phosphate buffered saline (PBS) inoculated with the bacterial strain was poured in. This was cultured for 1 hour in a shaking incubator maintained at 35°C. The culture solution was diluted and smeared on an agar medium plate. Serial dilution was performed to enable colony counting, and a 0.9 wt.% NaCl solution was used in this process. After calculating the initial microbial concentration (C0, CFU / mL) taking into account the dilution concentration, the antibacterial activity was calculated using the following formula 1.

[0106]

number

[0107] In one embodiment of the present specification, the sample used in the method 4 is a sample containing the compound.

[0108] In one embodiment of the present specification, when carrying out the method 4, the standard strain of E. coli ATCC25922 is used.

[0109] In one embodiment of the present invention, when carrying out the method 4, the strain is 1.5×10 5 CFU / ml ~3×10 5 Use by inoculating CFU / ml.

[0110] In one embodiment of the present specification, the antibacterial resin has an antibacterial activity against Gram-positive bacteria of 90% or more as measured by the above method 4.

[0111] In one embodiment of the present specification, the compound has an antibacterial activity against Gram-negative bacteria of 90% or more as measured by Method 4 above.

[0112] In one embodiment of the present specification, the compound has an antibacterial activity against fungi of 90% or more as measured by method 4 above.

[0113] According to one embodiment of the present specification, the antibacterial activity is 92% or more, 94% or more, 96% or more, 98% or more, 99% or more, or 99.8% or more. The upper limit of the antibacterial activity is not particularly limited, and is, for example, 100% or less or less than 100%.

[0114] Since the above Gram-positive, Gram-negative and fungal strains can cause various diseases when in contact, as well as secondary infections, it is preferable to use one compound that exhibits antibacterial properties against all of the above Gram-positive, Gram-negative and fungal strains.

[0115] One embodiment of the present invention provides a method for checking impurities as follows. Specifically, the method is a method for checking impurities in a compound containing a quaternary ammonium structure having an acrylate group or a methacrylate group, and the impurity checking is carried out by at least one of the following methods 1' to 3'.

[0116] [Method 1'] A 20 wt % aqueous solution of the compound is analyzed by UV / Vis spectroscopy to measure the absorbance Abs for light with a wavelength of 290 nm, and the turbidity Tb is calculated from the measured absorbance Abs using the following formula 1. If the calculated turbidity Tb is 120 or more, the presence of impurities is confirmed.

[0117] [Formula 1] Abs=0.00309Tb+0.04946

[0118] [Method 2'] The compound is dissolved in a mixed solution containing acetonitrile and water in a volume ratio of 5:5 and analyzed by HPLC / CAD. When a peak of 100 mV or more is detected at 4 to 9 minutes, the presence of impurities is confirmed.

[0119] [Method 3'] The compound is dissolved in DMF and analyzed by GPC / RI-DMF. When a peak of 10 mV or more is detected at 10 to 18 minutes, the presence of an impurity is confirmed.

[0120] Here, the method 2' may be carried out according to the following specific conditions.

[0121] -Column: Capcellpak CN, 4.6mmIDx150mmL, 5μm, Shiseido -First mobile phase: acetonitrile / trichloroacetic acid = 100 / 0.1 (v / v,%) - Second mobile phase: H2O / trichloroacetic acid = 100 / 0.1 (v / v,%) -Flow rate: 1mL / min -Injection volume: 5μL -Progress time: 15 minutes

[0122] Here, the method 3' may be carried out according to the following specific conditions.

[0123] -Column: PLgel column -1st mobile phase: DMF / 0.01M LiBr -Flow rate: 1mL / min -Injection volume: 100μL -Progress time: 35 minutes

[0124] According to one embodiment of the present invention, the impurity may be a polymer containing a compound containing a quaternary ammonium structure having an acrylate group or a methacrylate group and / or a polymer containing a unit derived from the compound containing a quaternary ammonium structure having an acrylate group or a methacrylate group. For example, the impurity may be a homopolymer of the compound.

[0125] In general, the compound containing a quaternary ammonium structure having an acrylate group or a methacrylate group has a very high solubility in water or an organic solvent, and therefore the structure can be easily confirmed by a general solution 1H NMR spectrum. On the other hand, the polymer containing the compound containing a quaternary ammonium structure having an acrylate group or a methacrylate group and the polymer containing a unit derived from the compound containing a quaternary ammonium structure having an acrylate group or a methacrylate group have a low solubility in water or an organic solvent, and therefore the structure cannot be easily confirmed by a solution NMR spectrum. In other words, when the compound containing a quaternary ammonium structure having an acrylate group or a methacrylate group is mixed with impurities, it is difficult to confirm whether the impurities are included in the solution NMR spectrum.

[0126] The method for identifying impurities according to the present invention has an advantage that impurities can be easily identified even when the compound containing a quaternary ammonium structure having an acrylate group or methacrylate group and impurities are mixed together.

[0127] In addition, while methods such as solid NMR require long experimental times, the method of the present invention for checking impurities does not require long experimental times, which has the advantage that it can be applied to quality control such as QC (Quality Control).

[0128] For example, homopolymer impurities may be generated during the scale-up synthesis process of the compound, and the above-mentioned method for identifying the impurities allows the grade of the impurity to be easily and quickly evaluated according to its amount.

[0129] According to one embodiment of the present invention, the above-mentioned explanation for Method 1 can be applied to Method 1' used in the impurity confirmation method, the above-mentioned explanation for Method 2 can be applied to Method 2', and the above-mentioned explanation for Method 3 can be applied to Method 3'.

[0130] One embodiment of the present invention provides a composition comprising the aforementioned compound.

[0131] According to one embodiment of the invention, the composition is an antibacterial composition.

[0132] According to one embodiment of the present invention, the composition may consist of the aforementioned compounds, for example, the composition may consist of a compound containing a quaternary ammonium structure having an acrylate or methacrylate group, and having a turbidity of less than 120 as determined by method 1.

[0133] According to one embodiment of the present invention, the composition may contain the above-mentioned compounds and the above-mentioned impurities. For example, the composition may consist of compounds containing a quaternary ammonium structure having an acrylate group or a methacrylate group, and having a turbidity of less than 120 and a turbidity of 120 or more as determined by the method 1.

[0134] According to one embodiment of the present invention, the composition may further comprise an additive in addition to the compound.

[0135] According to one embodiment of the present invention, the additive may be an additive that exhibits an antibacterial effect.

[0136] According to one embodiment of the present invention, the additive may be any material used in the art without any limitations.

[0137] In the present invention, when it is said that a member (layer) is located "on" another member (layer), this includes not only the case where a member (layer) is in contact with the other member, but also the case where another member (layer) exists between the two members (layers).

[0138] In the present invention, when a part is said to "comprise" a certain component, this does not mean that it excludes other components, but that it may further include other components, unless otherwise specified to the contrary. EXAMPLES

[0139] Hereinafter, the present invention will be described in detail with reference to examples in order to specifically explain the present invention. However, the examples of the present invention can be modified in various different forms, and the scope of the present invention is not to be construed as being limited to the examples described below. The examples of the present invention are provided to more completely explain the present invention to those having average knowledge in the art.

[0140] <Production Example A> Synthesis of Compound A-1. Synthesis of Compound 1, Compound 2, and Compound 3

[0141] [ka]

[0142] 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 tetrahydrofuran (THF) (solvent). (2) While stirring the materials, 0.1 mol of acryloyl chloride was added dropwise onto the reaction solution (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.

[0143] Step 2. (1) The product of Step 1 and 1-bromooctane (production of compound 1), 1-bromodecane (production of compound 2), or 1-bromododecane (production of compound 3) were dissolved in acrylonitrile (solvent) in a 1:1 ratio at 50 wt%. (2) Next, p-methoxyphenol, a polymerization inhibitor, was added (ratio to reactants: 1:0.001eq). (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) and then filtered. (5) Vacuum dried at 45°C.

[0144] A-2. Synthesis of compound 4

[0145] [ka]

[0146] Step 1 (1) 0.1 mol of 2-(dioctylamino)ethanol (DOAE), 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 acryloyl chloride was added dropwise onto the reaction solution (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.

[0147] Step 2 (1) The product of Step 1 and 1-bromooctane were dissolved in acrylonitrile (solvent) in a 1:1 ratio at 50 wt%. (2) Next, p-methoxyphenol, a polymerization inhibitor, was added (ratio to reactants: 1:0.001eq). (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) and then filtered. (5) Vacuum dried at 45°C.

[0148] A-3. Synthesis of compound 5

[0149] [ka]

[0150] 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 above materials, 0.1 mol of methacryloyl chloride was added dropwise onto the reaction solution (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.

[0151] Step 2. (1) The product of Step 1 and 1-bromodecane were dissolved in acrylonitrile (solvent) in a 1:1 ratio at 50 wt%. (2) Next, p-methoxyphenol, a polymerization inhibitor, was added (ratio to reactants: 1:0.001eq). (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) and then filtered. (5) Vacuum dried at 45°C.

[0152] A-4. Synthesis of compound 6

[0153] [ka]

[0154] Step 1. (1) 0.1 mol of 2-(butylhexylamino)ethanol (BHAE), 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 (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.

[0155] Step 2. (1) The product of Step 1 and 1-bromodecane were dissolved in acrylonitrile (solvent) in a 1:1 ratio at 50 wt%. (2) Next, p-methoxyphenol, a polymerization inhibitor, was added (ratio to reactants: 1:0.001eq). (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) and then filtered. (5) Vacuum dried at 45°C.

[0156] A-5. Synthesis of compound 7

[0157] [ka]

[0158] Step 1. (1) 0.1 mol of 2-(butyloctylamino)ethanol (BOAE), 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 (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.

[0159] Step 2. (1) The product of Step 1 and 1-bromodecane were dissolved in acrylonitrile (solvent) in a 1:1 ratio at 50 wt%. (2) Next, p-methoxyphenol, a polymerization inhibitor, was added (ratio to reactants: 1:0.001eq). (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) and then filtered. (5) Vacuum dried at 45°C.

[0160] A-6. Synthesis of compound 8

[0161] [ka]

[0162] Step 1. (1) 0.1 mol of 2-(butyldecylamino)ethanol (BDAE), 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 acryloyl chloride was added dropwise onto the reaction solution (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.

[0163] Step 2. (1) The product of Step 1 and 1-bromodecane were dissolved in acrylonitrile (solvent) in a 1:1 ratio at 50 wt%. (2) Next, p-methoxyphenol, a polymerization inhibitor, was added (ratio to reactants: 1:0.001eq). (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) and then filtered. (5) Vacuum dried at 45°C.

[0164] A-7. Synthesis of Compound 9

[0165] [ka]

[0166] Step 1. (1) 0.1 mol of 2-(dibutylamino)butanol (DBAB), 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 acryloyl chloride was added dropwise onto the reaction solution (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.

[0167] Step 2. (1) The product of Step 1 and 1-bromooctane were dissolved in acrylonitrile (solvent) in a 1:1 ratio at 50 wt%. (2) Next, p-methoxyphenol, a polymerization inhibitor, was added (ratio to reactants: 1:0.001eq). (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) and then filtered. (5) Vacuum dried at 45°C.

[0168] A-8. Synthesis of compound 10

[0169] [ka]

[0170] Step 1. (1) 0.1 mol of 2-(dioctylamino)butanol (DOAB), 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 acryloyl chloride was added dropwise onto the reaction solution (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.

[0171] Step 2. (1) The product of Step 1 and 1-bromooctane were dissolved in acrylonitrile (solvent) in a 1:1 ratio at 50 wt%. (2) Next, p-methoxyphenol, a polymerization inhibitor, was added (ratio to reactants: 1:0.001eq). (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) and then filtered. (5) Vacuum dried at 45°C.

[0172] In the above synthesis example, 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 can 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.

[0173] <Production Example B> Sample production In the preparation of compound 3 in step 2(3) of Preparation Example A-1, the reaction time was 4 hours, 8 hours, 10 hours, 12 hours, 16 hours, 20 hours, and 24 hours, respectively, and the products were collected and named samples 1 to 7, respectively.

[0174] <Example> Example 1. Turbidity measurement The UV / Vis of Samples 1 to 7 produced in Production Example B was measured using Method 1 of the present invention, and the results are shown in Figure 1. In addition, the measured absorbance (Abs) was converted into turbidity using the following formula 1, and the converted values ​​are shown in Table 1 below.

[0175] [Formula 1] Abs=0.00309Tb+0.04946

[0176] Specifically, the turbidity was measured by UV / Vis spectroscopy analysis under the following conditions.

[0177] 1) UV / Vis spectroscopy measurement 500 mg of each of samples 1 to 7 was placed in a vial, and 20 wt% aqueous solutions were prepared using distilled water (DI water), and then the absorbance at 290 nm wavelength was confirmed by UV / Vis spectroscopy (Agilent 8453, 200-1100 nm, resolution 2 nm, 1 mm cuvette used). DI water was used as a reference for the measurement.

[0178] 2) Derivation of turbidity calculation formula (formula 1) Five types of turbidity standard solutions (0, 1, 10, 100, 1000 NTU each) were analyzed by UV / Vis spectroscopy (Agilent 8453, 200~1100 nm, resolution 2 nm, 1 mm cuvette) to confirm the absorbance at 290 nm wavelength. An empty cuvette cell was used as a reference for the measurement.

[0179] A calibration curve (Equation 1) was derived from the absorbance in the range of 0 NTU to 1,000 NTU. (NTU: Nephelometric Turbidity Unit, water quality standard is 1 NTU)

[0180] [Formula 1] Abs=0.00309Tb+0.04946 (Abs: absorbance, Tb: turbidity)

[0181] 3) Turbidity calculation for samples 1 to 7 The absorbances of Samples 1 to 7 confirmed in 1) above were inserted into Equation 1 to derive the turbidity.

[0182] [Table 1]

[0183] From Table 1, it can be seen that as the polymerization proceeds and the amount of homopolymer relative to the compound increases (from sample 1 to 7), the turbidity improves. Specifically, it can be seen that samples 1 and 2, which had a short polymerization time and produced little homopolymer, have a converted turbidity of less than 40. It can also be seen that samples 3 to 6, which had an intermediate polymerization time, produced some homopolymer and had a turbidity of 40 or more and less than 120. On the other hand, it can be seen that sample 7, which had a long polymerization time and produced a large amount of homopolymer, had a turbidity of 120 or more.

[0184] This shows that the level of impurities can be confirmed by measuring turbidity using Method 1 and Equation 1.

[0185] Example 2. HPLC / CAD measurement The impurities in Sample 1 and Sample 6 were identified using Method 2 of the present invention.

[0186] Specifically, HPLC / CAD was measured under the following conditions.

[0187] -Column: Capcellpak CN, 4.6mmIDx150mmL, 5μm, Shiseido -First mobile phase: acetonitrile / trichloroacetic acid = 100 / 0.1 (v / v,%) - Second mobile phase: H2O / trichloroacetic acid = 100 / 0.1 (v / v,%) -Flow rate: 1mL / min -Injection volume: 5μL -Progress time: 15 minutes

[0188] Figure 2 shows the HPLC / CAD measurement results for sample 1. Since no impurities other than compound 3 were contained during the measurement in Figure 2, it can be seen that two or more peaks were derived only at 1 to 3 minutes, and no peaks were derived at 4 to 9 minutes.

[0189] Figure 3 shows the HPLC / CAD measurement results for sample 6. Sample 6 used in Figure 3 contains compound 3 and impurities, and it can be seen that a peak of 100 mV or more was detected at 4 to 9 minutes, along with two or more peaks detected at 1 to 3 minutes.

[0190] Example 3. GPC / RI-DMF measurement Using method 3 of the present invention, impurities in Sample 1 and Sample 7 were identified.

[0191] Specifically, GPC / RI-DMF was measured under the following conditions.

[0192] -Column: PLgel column -1st mobile phase: DMF / 0.01M LiBr -Flow rate: 1mL / min -Injection volume: 100μL -Progress time: 35 minutes

[0193] FIG. 4 shows the results of GPC / RI-DMF measurement of sample 1, and FIG. 5 shows the results of GPC / RI-DMF measurement of sample 7.

[0194] Figure 4 shows the results of measurements taken with Sample 1, which contains the compound and a trace amount of homopolymer, and Figure 5 shows the results of measurements taken with Sample 7, which contains the compound and a large amount of homopolymer. It can be seen that peaks of 10 mV or more were detected between 10 and 18 minutes in both Figures 4 and 5. This confirmed that even if the compound contains only a trace amount of homopolymer (impurity), it is possible to detect whether or not the impurity is present by GPC / RI-DMF measurement as in Method 3.

[0195] Comparative example 1.GPC / RI-CHCl3 measurement In Example 3, GPC / RI-CHCl3 was measured for Sample 1 and Sample 6 using CHCl3 instead of DMF.

[0196] FIG. 6 shows the measurement results of compound 3 produced in Production Example A-1, and FIG. 7 shows the measurement results of sample 6 by GPC / RI-CHCl3.

[0197] It can be seen from Fig. 6 that a peak of 20 mV or more was detected at 18 to 22 minutes when the compound of the present invention was measured using GPC / RI-CHCl3. On the other hand, it can be seen from Fig. 7 that no peak was detected at 18 to 22 minutes. Sample 6 contains compounds and impurities, and a peak of 20 mV or more should have been detected at 18 to 22 minutes in Fig. 7 as in Fig. 6. However, since no such peak was detected in Fig. 7, it was confirmed that GPC / RI-CHCl3 is not suitable for detecting impurities.

[0198] Example 4. Antibacterial activity measurement 1 g of sample was placed in a 250 mL Erlenmeyer flask, and 50 mL of phosphate buffered saline (PBS) inoculated with E. coli ATCC 25922 standard strain was poured in. This was cultured for 1 hour in a shaking incubator maintained at 35°C. The culture solution was diluted and smeared on an agar medium plate. Serial dilutions were performed to enable colony counting, and 0.9 wt.% NaCl solution was used in this process. The initial microbial concentration (C0, CFU / mL) was calculated taking into account the dilution concentration, and the antibacterial activity was calculated using the following formula 1.

[0199]

number

[0200] In the following Table 2, the control is a bacterial inoculated culture medium to which no sample was added, and is a measure of whether the bacteria grew properly. In the following Example 4-1 and Comparative Example 4-1, the reliability of the experiment was confirmed through the control in the following Table 2, and then the experiment was carried out.

[0201] [Table 2]

[0202] When the results in Table 2 are summarized in Table 1, it can be seen that samples with low turbidity have high antibacterial activity.

[0203] This confirms that the lower the impurity content, the lower the turbidity and the higher the antibacterial activity.

Claims

1. A compound containing a quaternary ammonium structure having an acrylate group or a methacrylate group, A compound having a turbidity of less than 120 as derived by Method 1 below: [Method 1] A 20 wt % aqueous solution of the compound was analyzed by UV / Vis spectroscopy to measure absorbance Abs for light with a wavelength of 290 nm, and turbidity Tb was calculated from the measured absorbance Abs using the following Equation 1. [Formula 1] Abs=0.00309Tb+0.04946

2. 2. The compound of claim 1, wherein the turbidity is less than 40.

3. The compound according to claim 1, wherein no peak of 100 mV or more is detected between 4 and 9 minutes when the compound is subjected to the following method 2: [Method 2] The compound is dissolved in a mixed solution containing acetonitrile and water in a volume ratio of 5:5, and analyzed by HPLC / CAD.

4. The compound according to claim 3, wherein the compound has a peak detected at 1 to 3 minutes when subjected to method 2.

5. The compound according to claim 1, wherein no peak of 10 mV or more is detected between 10 and 18 minutes when the compound is subjected to the following method 3: [Method 3] The compound is dissolved in DMF and analyzed by GPC / RI-DMF.

6. The compound according to claim 1, which is represented by the following chemical formula 1: 【Chemistry 1】 In the above Chemical Formula 1, R1 to R3 are the same or different and each independently represents a hydrogen atom or a methyl group; R4 to R6 are the same or different and each independently represents an alkyl group; L is an alkylene group.

7. The compound according to claim 6, wherein any one of R4 to R6 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.

8. The compound according to claim 6, wherein R2 and R3 are hydrogen, R1 is hydrogen or a methyl group, and L is an alkylene group having 1 to 30 carbon atoms.

9. The compound according to claim 1, which is any one selected from the following compounds 1 to 10: 【Chemistry 2】 【Chemistry 3】

10. A method for identifying impurities in a compound containing a quaternary ammonium structure having an acrylate group or a methacrylate group, comprising the steps of: The impurity confirmation is carried out by at least one of the following methods 1' to 3': [Method 1'] A 20 wt % aqueous solution of the compound is analyzed by UV / Vis spectroscopy to measure absorbance Abs for light with a wavelength of 290 nm, and turbidity Tb is calculated from the measured absorbance Abs using the following formula 1. If the calculated turbidity Tb is 120 or more, the presence of impurities is confirmed. [Formula 1] Abs=0.00309Tb+0.04946 [Method 2'] The compound is dissolved in a mixed solution containing acetonitrile and water in a volume ratio of 5:5 and analyzed by HPLC / CAD. When a peak of 100 mV or more is detected at 4 to 9 minutes, the presence of impurities is confirmed. [Method 3'] The compound is dissolved in DMF and analyzed by GPC / RI-DMF. When a peak of 10 mV or more is detected between 10 and 18 minutes, the presence of an impurity is confirmed.

11. An antibacterial composition comprising a compound according to any one of claims 1 to 9.

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