An antibacterial agent and its preparation method and application

Abstract

The invention discloses an antibacterial agent and a preparation method and application thereof, comprising 0.005-0.02 parts of chitosan-2-(3-methylbenzamide), 0.05-0.1 parts of pH buffer, 0.1-0.15 parts of moisturizing agent, 0.01-0.02 parts of surfactant and 0.01-0.2 parts of essence; the structural formula of chitosan-2-(3-methylbenzamide) is shown in formula (I): wherein n is a natural number, the bactericidal rate is high and the antibacterial range is wide.

Description

Technical Field

[0001] The present invention relates to the technical field of paper towels, and in particular to an antibacterial agent and a preparation method and application thereof. Background Art

[0002] In daily life, due to the uneven living standards and lack of health and safety awareness, various bacteria, fungi and other pathogenic microorganisms often cause biological pathology, posing a serious threat to human physical and mental health. In order to protect people's life, health and physical and mental safety, the research and development of antimicrobial agents cannot be ignored.

[0003] In the related art, in order to reduce the irritation of antibacterial agents to the skin, chitosan is often added as a bactericide. Chitosan has been widely studied and applied in many fields due to its unique physical and chemical properties such as natural cationicity, easy degradability, and non-toxicity of reduced products. In particular, its broad-spectrum antibacterial property has attracted special attention in the field of antibacterial and antiviral.

[0004] However, chitosan has a mild antibacterial effect, can only be manifested under acidic conditions, and has poor solubility, which greatly reduces the application range and bactericidal effect of antibacterial agents. Summary of the invention

[0005] In view of this, the present application provides an antibacterial agent and a preparation method and application thereof, which has a high bactericidal rate and a wide antibacterial range.

[0006] In order to achieve the above technical objectives, this application adopts the following technical solutions:

[0007] In a first aspect, the present application provides an antibacterial agent, comprising 0.005-0.02 parts of chitosan-2-(3-methylbenzamide), 0.05-0.1 parts of pH buffer, 0.1-0.15 parts of moisturizer, 0.01-0.02 parts of surfactant, and 0.01-0.2 parts of flavor; the structural formula of chitosan-2-(3-methylbenzamide) is shown in formula (I):

[0008] Wherein, n is a natural number.

[0009] Preferably, the preparation method of chitosan-2-(3-methylbenzamide) is as follows:

[0010] S1. Using DCC and 3-methylbenzoic acid as raw materials, a dehydration reaction is carried out to obtain 3-methylbenzoic anhydride;

[0011] S2. In an alkaline alcohol solution, chitosan and 3-methylbenzoic anhydride are used as raw materials to carry out an amidation reaction to obtain chitosan-2-(3-methylbenzamide).

[0012] Preferably, the molar ratio of 3-methylbenzoic acid to DCC is 1:0.5-1.

[0013] Preferably, the mass ratio of 3-methylbenzoic anhydride to chitosan is 30:1-2.

[0014] Preferably, in step S1, the temperature of the dehydration reaction is 25-30°C, and the reaction time is 6-8h.

[0015] Preferably, in step S2, the temperature of the amidation reaction is 45-50° C., and the reaction time is 7-10 h.

[0016] Preferably, the base includes one or more of triethylamine, tetramethylethylenediamine, sodium hydroxide, potassium hydroxide, potassium carbonate, and sodium carbonate.

[0017] Preferably, the moisturizing agent comprises a mixture of ethanol, glycerol, propylene glycol and 1,3-butylene glycol.

[0018] In a second aspect, the present application provides a method for preparing an antibacterial agent, comprising the following steps: mixing a moisturizer, a surfactant and water and heating the mixture to 90-95°C, keeping the mixture warm for 30-60 minutes, cooling the mixture to 45-50°C, adding chitosan-2-(3-methylbenzamide), pH buffer solution and essence, continuing to cool the mixture to room temperature, and discharging the mixture to obtain the antibacterial agent.

[0019] In a third aspect, the present application provides a disinfectant tissue containing an antibacterial agent.

[0020] The beneficial effects of the present application are as follows: the antibacterial agent component of the present application is mild and non-irritating, has no side effects, and has multiple functions such as sterilization and disinfection, cleaning and decontamination, and odor elimination; the production process is simple and the raw materials are easily available; the antibacterial agent of the present application has a wide pH applicability and excellent bactericidal performance. DETAILED DESCRIPTION

[0021] In order to make the purpose, technical solution and advantages of the present invention more clearly understood, the present invention is further described in detail below in conjunction with the embodiments. It should be understood that the specific embodiments described herein are only used to explain the present invention and are not used to limit the present invention.

[0022] The present application provides an antibacterial agent, comprising 0.005-0.02 parts of chitosan-2-(3-methylbenzamide), 0.05-0.1 parts of pH buffer, 0.1-0.15 parts of moisturizer, 0.01-0.02 parts of surfactant, and 0.01-0.2 parts of flavor; the structural formula of chitosan-2-(3-methylbenzamide) is shown in formula (I):

[0023] Wherein, n is a natural number;

[0024] The value of n depends on the degree of polymerization of the commercial chitosan raw material.

[0025] In this scheme, pH buffer is added according to the formula ratio to maintain the pH of the disinfectant within the range applicable to the human body; moisturizer is added according to the formula ratio to make it have a good moisturizing effect; surfactant is added according to the formula ratio to make it have the functions of washing, cleaning and decontamination, and can make all components evenly dispersed and mixed; an appropriate amount of flavor is added to make it have a refreshing and odor-removing effect; the remaining material of this scheme is water; chitosan-2-(3-methylbenzamide) plays an antibacterial role, and has the following advantages compared with chitosan: chitosan Chitosan-2-(3-methylbenzamide) belongs to amide-modified chitosan. The chitosan-2-(3-methylbenzamide) of this scheme has a wide pH adaptability for sterilization, which broadens the antibacterial range of chitosan. The modified chitosan-2-(3-methylbenzamide) is more conducive to the ability of chitosan to pass through the cell wall and cytoplasmic membrane, thereby further improving the antibacterial activity. Chitosan-2-(3-methylbenzamide) has good solubility and is easy to be evenly dispersed in water with the help of a moisturizer, further improving the antibacterial effect.

[0026] The pH buffer includes one or more of citric acid-sodium citrate, potassium hydrogen phosphate-disodium hydrogen phosphate, acetic acid-sodium acetate or lauric acid-sodium laurate.

[0027] The surfactant includes one or more of dodecylpyridinium chloride, dodecylpyridinium bromide, cetylpyridinium chloride, cetylpyridinium bromide, sodium lauryl sulfate, polyethylene glycol monostearate, polyoxyethylene stearate, and polyoxyethylene hardened castor oil.

[0028] The essence includes one or more of jasmine essence, orange essence, rose essence, mint essence and osmanthus essence, and the essences are all commercially available raw materials.

[0029] The moisturizer includes a mixture of ethanol, glycerol, propylene glycol, and 1,3-butylene glycol; in some embodiments, the moisturizer includes 1-2 parts of ethanol, 3-5.5 parts of glycerol, 1.5-2.5 parts of propylene glycol, and 1.5-2 parts of 1,3-butylene glycol.

[0030] The preparation method of chitosan-2-(3-methylbenzamide) is as follows:

[0031] S1. Using DCC and 3-methylbenzoic acid as raw materials, a dehydration reaction is carried out to obtain 3-methylbenzoic anhydride;

[0032] S2. In an alkaline alcohol solution, chitosan and 3-methylbenzoic anhydride are used as raw materials to carry out an amidation reaction to obtain chitosan-2-(3-methylbenzamide).

[0033] The introduction of side chains in the preparation of chitosan-2-(3-methylbenzamide) can improve the solubility of chitosan. At the same time, the amide-modified chitosan broadens the pH value of chitosan and expands its antibacterial range. After modification, it is more conducive to the ability of chitosan to pass through the cell wall and cytoplasmic membrane, thereby further improving the antibacterial activity.

[0034] The reaction formula for its preparation is as follows:

[0035]

[0036] In step S1, the temperature of the dehydration reaction is 25-30°C, and the reaction time is 6-8h.

[0037] In step S2, the temperature of the amidation reaction is 45-50° C., and the reaction time is 7-10 h.

[0038] Specifically, the preparation process of chitosan-2-(3-methylbenzamide) is as follows:

[0039] Dissolve 3-methylbenzoic acid and dicyclohexylcarbodiimide (DCC) in an organic solvent, stir and react for 6-8 hours at 25-30° C., filter, and remove the organic solvent from the filtrate under reduced pressure to obtain 3-methylbenzoic anhydride;

[0040] The prepared 3-methylbenzoic anhydride and chitosan are dissolved in an alkaline alcohol solution, stirred and reacted at 45-50°C for 7-10 hours, the reaction solution is poured into an alkaline alcohol solution, stirred overnight, filtered, the filter cake is washed with alcohol until neutral, the filter cake is vacuum dried, and then the product is extracted and purified with chloroform and dried to obtain chitosan-2-(3-methylbenzamide).

[0041] The base includes one or more of triethylamine, tetramethylethylenediamine, sodium hydroxide, potassium hydroxide, potassium carbonate, and sodium carbonate.

[0042] The organic solvent includes at least one of dichloromethane, dichloroethane, 1,4-dioxane, tetrahydrofuran and acetonitrile.

[0043] The alcohol includes one or more of methanol, ethanol, isopropanol and n-butanol.

[0044] In some embodiments, the molar ratio of 3-methylbenzoic acid to DCC is 1:0.5-1.

[0045] In some embodiments, the mass ratio of 3-methylbenzoic anhydride to chitosan is 30:1-2.

[0046] In some embodiments, the ratio of 3-methylbenzoic acid to the organic solvent is 1 g: 5-20 mL.

[0047] In some embodiments, the ratio of 3-methylbenzoic anhydride to the alcohol solution of the base is 1 g: 2-10 ml.

[0048] In some embodiments, the ratio of base to alcohol is 1 g: 2-30 ml.

[0049] Within the limited range, while ensuring the normal progress of the reaction, it is beneficial to improve the yield of chitosan-2-(3-methylbenzamide).

[0050] The present application provides a method for preparing an antibacterial agent, comprising the following steps: mixing a moisturizer, a surfactant and water, heating the mixture to 90-95°C, keeping the mixture warm for 30-60 minutes, cooling the mixture to 45-50°C, adding chitosan-2-(3-methylbenzamide), a pH buffer solution and an essence, continuing to cool the mixture to room temperature and discharging the mixture to obtain the antibacterial agent.

[0051] The present application provides a disinfectant paper towel containing an antibacterial agent. The disinfectant paper towel can be obtained by soaking a wet wipe carrier in the antibacterial agent for 3-6 hours, or by spraying the antibacterial agent on the surface of the paper towel.

[0052] The present solution is further described below through specific embodiments.

[0053] Raw material preparation

[0054] Chitosan-2-(3-methylbenzamide): In a 250mL three-necked flask with a magnet, add 50.2g 3-methylbenzoic acid, 500mL dichloromethane, and 38.0g dicyclohexylcarbodiimide (DCC). Stir and dissolve at room temperature for 7h, then filter and vacuum evaporate the filtrate to obtain 3-methylbenzoic anhydride. In a 250mL three-necked flask with a magnet, add the above 43.0g 3-methylbenzoic anhydride and 100mL methanol, stir and dissolve for use. Take another 500mL three-necked flask with a magnet, add 1.5g chitosan, 45mL water, and 100mL methanol, stir and dissolve, pour the above 3-methylbenzoic anhydride methanol solution into the chitosan solution, and stir and react at 45°C for 7h. Dissolve 36.9g potassium hydroxide in 500mL anhydrous ethanol. After the reaction is completed, pour the reaction solution into the potassium hydroxide ethanol solution and stir overnight at room temperature. The mixture was filtered and washed with ethanol until neutral. The filter cake was dried in vacuum and then extracted with chloroform. Chitosan-2-(3-methylbenzamide) was obtained by vacuum drying. The yield was 77%.

[0055] The structural formula of chitosan-2-(3-methylbenzamide) is shown in formula (Ⅰ):

[0056] Wherein, n is a natural number.

[0057] Moisturizer: A mixture of 1 part ethanol, 3 parts glycerin, 1.5 parts propylene glycol, and 1.5 parts 1,3-butylene glycol.

[0058] Example 1

[0059] An antibacterial agent comprises 0.01 parts of chitosan-2-(3-methylbenzamide), 0.05 parts of citric acid-sodium citrate buffer, 0.1 parts of moisturizer, 0.01 parts of dodecylpyridinium chloride, 0.01 parts of jasmine essence and 100 parts of water.

[0060] A method for preparing an antibacterial agent comprises the following steps: mixing a moisturizer, a surfactant and water, heating the mixture to 90°C, keeping the mixture warm for 30 minutes, cooling the mixture to 50°C, adding chitosan-2-(3-methylbenzamide), a pH buffer solution and an essence, cooling the mixture to room temperature and discharging the mixture to obtain the antibacterial agent.

[0061] Example 2

[0062] An antibacterial agent, the rest of the contents are the same as those in Example 1, except that 0.005 parts of chitosan-2-(3-methylbenzamide) is included.

[0063] Example 3

[0064] An antibacterial agent, the rest of the contents are the same as those in Example 1, except that 0.02 parts of chitosan-2-(3-methylbenzamide) is included.

[0065] Example 4

[0066] An antibacterial agent, the rest of the contents are the same as those in Example 1, except that 0.05 parts of chitosan-2-(3-methylbenzamide) is included.

[0067] Example 5

[0068] An antibacterial agent comprises 0.01 parts of chitosan-2-(3-methylbenzamide), 0.1 parts of potassium hydrogen phosphate-disodium hydrogen phosphate buffer, 0.15 parts of moisturizer, 0.02 parts of sodium lauryl sulfate, 0.2 parts of orange essence and 100 parts of water.

[0069] Comparative Example 1

[0070] An antibacterial agent, the rest of the contents are the same as those of Example 1, except that chitosan-2-(3-methylbenzamide) is replaced by chitosan.

[0071] Comparative Example 2

[0072] An antibacterial agent, the rest of the contents are the same as those in Example 1, except that a moisturizing agent is not included.

[0073] Evaluation Test

[0074] According to the bactericidal performance test scheme in Appendix C of the "Hygiene Standard for Disposable Sanitary Products" (GB15979-2002), the antibacterial performance of the antibacterial agents of Examples 1-5 and Comparative Examples 1-2 was tested for antibacterial properties, and the bactericidal effects on typical pathogens Escherichia coli and Staphylococcus aureus were tested in different pH environments. The results are shown in Table 1.

[0075] Table 1 Test results

[0076]

[0077] The above are only preferred specific implementations of the present invention, but the protection scope of the present invention is not limited thereto. Any changes or substitutions that can be easily conceived by any technician familiar with the technical field within the technical scope disclosed by the present invention should be covered within the protection scope of the present invention.

Claims

1. An antibacterial agent, characterized in that It comprises 0.005-0.02 parts of chitosan-2-(3-methylbenzamide), 0.05-0.1 parts of pH buffer, 0.1-0.15 parts of moisturizer, 0.01-0.02 parts of surfactant, and 0.01-0.2 parts of flavor; the structural formula of the chitosan-2-(3-methylbenzamide) is shown in formula (I): , where n is a natural number; The preparation method of chitosan-2-(3-methylbenzamide) is as follows: 50.2 g of 3-methylbenzoic acid, 500 mL of dichloromethane, and 38.0 g of dicyclohexylcarbodiimide (DCC) are added to a 250 mL three-necked flask with a magnetic device, and the mixture is stirred and dissolved at room temperature for 7 h, and then filtered and the filtrate is evaporated in vacuum to obtain 3-methylbenzoic anhydride. 43.0 g of the above 3-methylbenzoic anhydride and 100 mL of methanol are added to a 250 mL three-necked flask with a magnetic device, and stirred and dissolved for later use. Another 500 mL three-necked flask with a magnetic device is used, and 1.5 g of chitosan, 45 mL of water, and 100 mL of methanol are added to stir and dissolve. The methanol solution of the above 3-methylbenzoic anhydride is poured into the chitosan solution, and stirred and reacted at 45 °C for 7 h. 36.9 g of potassium hydroxide is dissolved in 500 mL of water and stirred and dissolved. mL of anhydrous ethanol, after the reaction is completed, pour the reaction solution into potassium hydroxide ethanol solution and stir overnight at room temperature, filter, wash with ethanol until neutral, vacuum dry the filter cake, extract with chloroform, and vacuum dry to obtain chitosan-2-(3-methylbenzamide).

2. A method for preparing an antibacterial agent, characterized in that: The method comprises the following steps: mixing a moisturizing agent, a surfactant and water, heating the mixture to 90°C, keeping the mixture warm for 30 minutes, cooling the mixture to 50°C, adding chitosan-2-(3-methylbenzamide), a pH buffer solution and an essence, and continuing to cool the mixture to room temperature, discharging the mixture to obtain an antibacterial agent; wherein the antibacterial agent comprises 0.01 parts of chitosan-2-(3-methylbenzamide), 0.05 parts of citric acid-sodium citrate buffer solution, 0.1 parts of moisturizing agent, 0.01 parts of dodecylpyridinium chloride, 0.01 parts of jasmine essence and 100 parts of water; or the antibacterial agent comprises 0.005 parts of chitosan-2-(3-methylbenzamide), 0.05 parts of citric acid-sodium citrate buffer solution, 0.1 parts of moisturizing agent, 0.01 parts of dodecylpyridinium chloride, 0.01 parts of jasmine essence and 100 parts of water. Sodium citrate buffer, 0.1 parts of humectant, 0.01 parts of dodecylpyridinium chloride, 0.01 parts of jasmine essence, and 100 parts of water; or, the antibacterial agent is composed of 0.02 parts of chitosan-2-(3-methylbenzamide), 0.05 parts of citric acid-sodium citrate buffer, 0.1 parts of humectant, 0.01 parts of dodecylpyridinium chloride, 0.01 parts of jasmine essence, and 100 parts of water; or, the antibacterial agent is composed of 0.05 parts of chitosan-2-(3-methylbenzamide), 0.05 parts of citric acid-sodium citrate buffer, 0.1 parts of humectant, 0.01 parts of dodecylpyridinium chloride, 0.01 parts of jasmine essence, and 100 parts of water; The preparation method of chitosan-2-(3-methylbenzamide) is as follows: 50.2 g of 3-methylbenzoic acid, 500 mL of dichloromethane, and 38.0 g of dicyclohexylcarbodiimide (DCC) are added to a 250 mL three-necked flask with a magnetic device, and the mixture is stirred and dissolved for reaction for 7 h at room temperature, and then the mixture is filtered and the filtrate is evaporated in vacuum to obtain 3-methylbenzoic anhydride; 43.0 g of the above 3-methylbenzoic anhydride and 100 mL of methanol are added to a 250 mL three-necked flask with a magnetic device, and the mixture is stirred and dissolved for later use; another 500 mL three-necked flask with a magnetic device is taken, and 1.5 g of chitosan, 45 mL of water, and 100 mL of methanol are added to stir and dissolve; the methanol solution of the above 3-methylbenzoic anhydride is poured into the chitosan solution, and the mixture is stirred and reacted at 45° C. for 7 h; 36.9 g of potassium hydroxide is dissolved in 500 mL of water, and the mixture is stirred and dissolved for later use; mL of anhydrous ethanol, after the reaction is completed, pour the reaction solution into potassium hydroxide ethanol solution and stir overnight at room temperature, filter, wash with ethanol until neutral, vacuum dry the filter cake, extract with chloroform, and vacuum dry to obtain chitosan-2-(3-methylbenzamide).

3. A method for preparing an antibacterial agent, characterized in that: The method comprises the following steps: mixing a moisturizing agent, a surfactant and water, heating the mixture to 90°C, keeping the mixture warm for 30 minutes, cooling the mixture to 50°C, adding chitosan-2-(3-methylbenzamide), a pH buffer solution and an essence, continuing to cool the mixture to room temperature, discharging the mixture and obtaining an antibacterial agent; wherein the antibacterial agent comprises 0.01 parts of chitosan-2-(3-methylbenzamide), 0.1 parts of potassium hydrogen phosphate-disodium hydrogen phosphate buffer solution, 0.15 parts of a moisturizing agent, 0.02 parts of sodium dodecyl sulfate, 0.2 parts of orange essence and 100 parts of water; The preparation method of chitosan-2-(3-methylbenzamide) is as follows: 50.2 g of 3-methylbenzoic acid, 500 mL of dichloromethane, and 38.0 g of dicyclohexylcarbodiimide (DCC) are added to a 250 mL three-necked flask with a magnetic device, and the mixture is stirred and dissolved for reaction for 7 h at room temperature, and then the mixture is filtered and the filtrate is evaporated in vacuum to obtain 3-methylbenzoic anhydride; 43.0 g of the above 3-methylbenzoic anhydride and 100 mL of methanol are added to a 250 mL three-necked flask with a magnetic device, and the mixture is stirred and dissolved for later use; another 500 mL three-necked flask with a magnetic device is taken, and 1.5 g of chitosan, 45 mL of water, and 100 mL of methanol are added to stir and dissolve; the methanol solution of the above 3-methylbenzoic anhydride is poured into the chitosan solution, and the mixture is stirred and reacted at 45° C. for 7 h; 36.9 g of potassium hydroxide is dissolved in 500 mL of water, and the mixture is stirred and dissolved for later use; mL of anhydrous ethanol, after the reaction is completed, pour the reaction solution into potassium hydroxide ethanol solution and stir overnight at room temperature, filter, wash with ethanol until neutral, vacuum dry the filter cake, extract with chloroform, and vacuum dry to obtain chitosan-2-(3-methylbenzamide).

4. A disinfecting paper towel comprising the antibacterial agent according to claim 1.

Images