Bacteriostatic agent and preparation method thereof

Abstract

The invention discloses a bacteriostatic agent and a preparation method thereof, and the bacteriostatic agent comprises the following components: triclocarban, 2, 4-dichlorobenzyl alcohol, 18-crown-6, a surfactant and a solvent. According to the bacteriostatic agent, efficient and non-toxic triclocarban is used as a main bactericide, 2, 4-dichlorobenzyl alcohol and 18-crown-6 are compounded to improve the bacteriostatic effect, and the bacteriostatic agent has a good inhibition effect on staphylococcus aureus, escherichia coli, candida albicans and pseudomonas aeruginosa.

Description

Technical Field

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

[0002] In daily life, toiletries are closely related to people's health. In order to maintain personal hygiene and prevent diseases, antimicrobial agents are added to many toiletries to inhibit bacterial growth. The function of these antimicrobial agents is to reduce or prevent the reproduction of bacteria in the product, thereby reducing the risk of infection and protecting the health of users. However, the use of antimicrobial agents has also aroused public concern about their safety and effectiveness.

[0003] Although antimicrobial agents are widely used in toiletries, some contain ingredients that are harmful to the environment or the human body. For example, some antimicrobial agents such as Triclosan and Benzalkonium chloride have been found to be harmful to aquatic ecosystems and may affect human health through the food chain. In addition, these chemicals may also promote the development of bacterial resistance, which is a global public health problem.

[0004] Although antimicrobial agents are added to many toiletries, the antibacterial effects of these antimicrobial agents are not always ideal. Some studies have shown that existing antimicrobial agents have a low inhibition rate against certain bacteria and are often only inhibitory against a few specific bacteria. This may be due to increased bacterial resistance or insufficient concentration of antimicrobial agents to effectively inhibit all types of bacteria. Therefore, developing new antimicrobial agents or improving the formulation of existing antimicrobial agents to improve their broad spectrum and antibacterial effects is an important direction of current research. Summary of the invention

[0005] The purpose of the present application is to provide an antibacterial agent with good antibacterial effect.

[0006] In order to achieve the above objectives, the technical solution adopted in the present application is: to provide an antibacterial agent, comprising the following components: triclocarban, 2,4-dichlorobenzyl alcohol, 18-crown-6, a surfactant and a solvent.

[0007] As a preference, the mass ratio of the 2,4-dichlorobenzyl alcohol to the 18-crown-6 is (3:5) to (1:1).

[0008] As another preference, the mass ratio of the 2,4-dichlorobenzyl alcohol to the 18-crown-6 is 1:1.

[0009] As another preferred embodiment, the composition comprises, by mass fraction, 15% to 30% triclocarban, 3% to 5% 2,4-dichlorobenzyl alcohol, 3% to 5% 18-crown-6, 5% to 10% surfactant and the remainder solvent.

[0010] As another preference, the solvent is polyoxyethylene ether.

[0011] As another preference, the surfactant is an amphoteric surfactant.

[0012] As another preference, the amphoteric surfactant is any one or more combinations of betaine-type amphoteric surfactants, amino acid-type amphoteric surfactants, phosphate betaine, and imidazoline-type amphoteric surfactants.

[0013] As another preference, the amphoteric surfactant is BS-12 dodecyl betaine.

[0014] Provided is a method for preparing an antibacterial agent, comprising the following steps:

[0015] S1: mixing and heating the surfactant and the solvent in a reaction vessel, followed by dehydration and desalination;

[0016] S2: Control the reaction temperature, add triclocarban, 2,4-dichlorobenzyl alcohol and 18-crown-6 into the reaction container, stir the reaction for a period of time and then cool to room temperature, filter the product and obtain the antibacterial agent.

[0017] More preferably, the reaction temperature is 50-80°C.

[0018] Compared with the prior art, the beneficial effects of this application are:

[0019] (1) The antibacterial agent of the present application uses highly efficient and non-toxic triclocarban as the main bactericide, and combines 2,4-dichlorobenzyl alcohol and 18-crown-6 to enhance the antibacterial effect, and has a good inhibitory effect on Staphylococcus aureus, Escherichia coli, Candida albicans and Pseudomonas aeruginosa;

[0020] (2) Adding 18-crown-6 to the antibacterial agent of the present application can improve the antibacterial stability of the antibacterial agent;

[0021] (3) The present application selects surfactants and suitable solvents, and adds triclocarban and 2,4-dichlorobenzyl alcohol during the heating process, so that the solubility of triclocarban and 2,4-dichlorobenzyl alcohol is improved, thereby obtaining a better antibacterial effect. DETAILED DESCRIPTION

[0022] Below, the present application is further described in conjunction with specific implementation methods. It should be noted that, under the premise of no conflict, the various embodiments or technical features described below can be arbitrarily combined to form new embodiments.

[0023] The terms "including" and "having" and any variations thereof in the specification and claims of this application are intended to cover non-exclusive inclusions. For example, a process, method, system, product or apparatus comprising a series of steps or units is not necessarily limited to those steps or units explicitly listed, but may include other steps or units not explicitly listed or inherent to these processes, methods, products or apparatuses.

[0024] The present application provides an antibacterial agent, comprising the following components: triclocarban, 2,4-dichlorobenzyl alcohol, 18-crown-6, a surfactant and a solvent.

[0025] The present application adds 2,4-dichlorobenzyl alcohol and 18-crown-6 components to the antibacterial agent, thereby being able to inhibit the proliferation of various different types of bacteria, and having a high inhibition rate for various bacteria, and is a relatively efficient antibacterial agent.

[0026] In some embodiments, the components of the antibacterial agent include, by mass fraction, 15% to 30% triclocarban, 3% to 5% 2,4-dichlorobenzyl alcohol, 3% to 5% 18-crown-6, 5% to 10% surfactant and the remainder solvent.

[0027] In some embodiments, the mass ratio of 2,4-dichlorobenzyl alcohol to 18-crown-6 is (3:5) to (1:1).

[0028] In some preferred embodiments, the ratio of 2,4-dichlorobenzyl alcohol to 18-crown-6 is 1:1.

[0029] As a new type of highly effective, broad-spectrum and safe antibacterial agent, triclocarban is widely used in medical disinfectants. It has a highly effective inhibitory effect on Gram-positive bacteria, Gram-negative bacteria, fungi, yeasts and viruses. When added to laundry detergent, triclocarban can kill germs on clothing and eliminate odors caused by bacterial growth; when added to antibacterial deodorant soap, it can be used by doctors, patients and food industry operators to wash their hands and disinfect, reducing cross-infection. When added to mouthwash and toothpaste, it has a highly effective antibacterial effect on oral pathogens, and has no adverse effects on the composition of natural flora in the oral cavity, and can reduce gum infection, eliminate bad breath, and remove dental plaque.

[0030] This application uses highly efficient and non-toxic triclocarban as the main bactericide. Triclocarban has a good effect on killing human odor bacteria and has good bactericidal function when used in laundry detergent. At the same time, other bactericides 2,4-dichlorobenzyl alcohol and 18-crown-6 are combined to complement each other to improve the bactericidal effect. Through scientific proportioning, a composite antibacterial agent that can take into account both rapid bactericidal and long-term antibacterial efficacy is formed.

[0031] The molecular structure of 18-crown-6 consists of a macrocyclic ring of 12 carbon atoms and 6 oxygen atoms alternating to form a cavity that can accommodate specific ions. 8-crown-6 is widely used in chemical and industrial applications, such as as an extractant, separation agent and ligand for metal ions, as well as in ion sensors and coordination polymers.

[0032] In the structure of 2,4-dichlorobenzyl alcohol, there is a chlorine atom at the 2nd and 4th positions of the benzene ring, and a hydroxyl group is connected to the methyl group of the benzene ring. 2,4-dichlorobenzyl alcohol is mainly used as a pharmaceutical intermediate. It is also used as a preservative for aqueous solutions, skin care lotions, creams, and gel products. It can also be used as a sterilant and disinfectant for sterilizing ointments, oral washes, and mouthwashes.

[0033] In some embodiments, the surfactant can be any one or a combination of multiple of a cationic surfactant, an anionic surfactant, a nonionic surfactant or an amphoteric surfactant.

[0034] Cationic surfactants include, but are not limited to, benzalkonium chloride, benzalkonium bromide, cetyltrimethylammonium chloride, dodecyldimethylbenzylammonium chloride, didecyldimethylammonium chloride.

[0035] Anionic surfactants include, but are not limited to, sodium dodecyl sulfate, sodium dodecylbenzene sulfonate, fatty acid salts, phosphate ester surfactants, carboxylate type gemini surfactants, and sulfonate type gemini surfactants.

[0036] The nonionic surfactants include, but are not limited to, fatty alcohol polyoxyethylene ethers, alkylphenol polyoxyethylene ethers, polyol polyoxyethylene ether fatty acid esters, glycerol fatty acid esters, and dodecyl polyethylene glycol ethers.

[0037] The amphoteric surfactant includes, but is not limited to, betaine-type amphoteric surfactant, amino acid-type amphoteric surfactant, phosphate betaine, and imidazoline-type amphoteric surfactant. Among them, the betaine-type amphoteric surfactant can be dodecyl betaine.

[0038] In some embodiments, the solvent is a polyoxyethylene ether.

[0039] In the preferred embodiment, the present application uses BS-12 dodecyl betaine as the amphoteric surfactant and secondary alcohol polyoxyethylene ether-9 as the solvent, both of which have good solubility for triclocarban and have a good synergistic effect on decontamination and sterilization. The use of amphoteric surfactants and solvents with better solubility can increase the content of antibacterial components and have a better antibacterial effect.

[0040] The present application also provides a method for preparing an antibacterial agent, comprising the following steps:

[0041] S1: mixing and heating the surfactant and the solvent in a reaction vessel, followed by dehydration and desalination;

[0042] S2: Control the reaction temperature, add triclocarban, 2,4-dichlorobenzyl alcohol and 18-crown-6 into the reaction container, stir the reaction for a period of time and then cool to room temperature, filter the product and obtain the antibacterial agent of the present application.

[0043] The present application improves the preparation method, liquefies triclocarban, and makes it water-based, thereby successfully solving the compatibility problem of triclocarban in aqueous media. At the same time, 2,4-dichlorobenzyl alcohol and 18-crown-6 are synergistically compounded to have efficient antibacterial properties. The laundry detergent containing the efficient cleaning and antibacterial agent can be well combined with textile fibers during the washing process, so that the textiles have a lasting antibacterial effect. At the same time, the efficient cleaning and antibacterial agent has excellent stability under acidic or alkaline conditions, and has a good compatibility effect with amphoteric surfactants.

[0044] The specific preparation method includes the following preparation steps:

[0045] S1: Add the surfactant and solvent into the reaction tank, mix them evenly, start stirring and heat to 60°C, evacuate the reaction tank, dehydrate, filter and desalinate, and control the temperature between 60 and 80°C according to the water content during the desalination process;

[0046] S2: Control the temperature of the reaction tank to 50-80°C, add corresponding amounts of triclocarban, 2,4-dichlorobenzyl alcohol and 18-crown-6, stir the reaction for a period of time and then cool to room temperature, filter the product and obtain the antibacterial agent of the present application.

[0047] Since triclocarban and 2,4-dichlorobenzyl alcohol have poor solubility in water and are easy to precipitate, the solubility of triclocarban and 2,4-dichlorobenzyl alcohol in the solvent is greatly increased through moderate heating reaction. After the same amount of antibacterial agent is added to the laundry detergent, the antibacterial effect of the laundry detergent is enhanced due to the increase in the content of triclocarban and 2,4-dichlorobenzyl alcohol.

[0048] At the same time, when the temperature when triclocarban and 2,4-dichlorobenzyl alcohol are added is controlled at 60°C, the solubility of triclocarban and 2,4-dichlorobenzyl alcohol is the largest, no precipitation occurs after cooling, and the solution is transparent. This is because triclocarban, 2,4-dichlorobenzyl alcohol and the solvent secondary alcohol polyoxyethylene ether-9 react well at 60°C, achieving water-based modification of triclocarban and 2,4-dichlorobenzyl alcohol and enhancing the solubility in laundry detergent.

[0049] Example 1

[0050] The preparation of an antibacterial agent comprises the following steps:

[0051] S1: Add 5 kg BS-12 dodecyl betaine and 72 kg polyoxyethylene ether into a reaction tank, mix well, start stirring and heat to 60 ° C, evacuate the reaction tank, dehydrate, filter and remove 5 kg of salt, and control the temperature between 60 and 80 ° C according to the water content during the desalination process;

[0052] S2: Control the temperature of the reaction tank to 60°C, add 15kg of triclocarban, 3kg of 2,4-dichlorobenzyl alcohol and 5kg of 18-crown-6 of corresponding mass, stir the reaction for a period of time and then cool to room temperature, filter the product and obtain the antibacterial agent of Example 1 of the present application.

[0053] Example 2

[0054] The addition amounts of 2,4-dichlorobenzyl alcohol and 18-crown-6 were adjusted to 3 kg each, and the addition amount of the solvent was adjusted to 74 kg. The other preparation steps were consistent with those in Example 1.

[0055] Example 3

[0056] The added amounts of 2,4-dichlorobenzyl alcohol and 18-crown-6 were adjusted to 5 kg, the added amount of the solvent was adjusted to 70 kg, and the other preparation steps were consistent with the preparation steps in Example 1.

[0057] Example 4

[0058] The addition amount of triclocarban was adjusted to 20 kg, the addition amount of the solvent was adjusted to 65 kg, and the other preparation steps were consistent with the preparation steps in Example 3.

[0059] Example 5

[0060] The addition amount of triclocarban was adjusted to 30 kg, the addition amount of the solvent was adjusted to 55 kg, and the other preparation steps were consistent with the preparation steps in Example 3.

[0061] Comparative Example 1

[0062] During the preparation process, 18-crown-6 was not added, and the amount of solvent added was adjusted to 77 kg accordingly. The other preparation steps were consistent with those in Example 2.

[0063] Comparative Example 2

[0064] During the preparation process, 2,4-dichlorobenzyl alcohol was not added, and the amount of solvent added was adjusted to 77 kg accordingly. The other preparation steps were consistent with the preparation steps in Example 2.

[0065] Comparative Example 3

[0066] No triclocarban was added during the preparation process, the amount of solvent added was adjusted to 89 kg accordingly, and the other preparation steps were consistent with the preparation steps in Example 2.

[0067] Comparative Example 4

[0068] During the preparation process, triclocarban and 2,4-dichlorobenzyl alcohol were not added, 21 kg of 18-crown-6 was added to 5 kg of surfactant and 74 kg of solvent, and the other preparation steps were consistent with the preparation steps in Example 2.

[0069] In order to intuitively present the differences between each embodiment and each comparative example, the preparation formulas of each embodiment and each comparative example are recorded in the following Table 1.

[0070] Table 1 Preparation formula of each embodiment and each comparative example project Triclocarban 2,4-Dichlorobenzyl alcohol 18-Crown-6 Surfactants Solvents Example 1 15 3 5 5 72 Example 2 15 3 3 5 74 Example 3 15 5 5 5 70 Example 4 20 5 5 5 65 Example 5 30 5 5 5 55 Comparative Example 1 15 3 / 5 77 Comparative Example 2 15 / 3 5 77 Comparative Example 3 / 3 3 5 89 Comparative Example 4 / / 21 5 74

[0071] Performance Testing

[0072] According to the light industry standard QB / T2738-2012 of the People's Republic of China "Evaluation Method for Antibacterial and Antibacterial Effects of Daily Chemical Products", the antibacterial test was carried out. The test bacteria were Staphylococcus aureus ATCC6538, Escherichia coli 8099, Candida albicans ATCC10231 and Pseudomonas aeruginosa ATCC15442. The antibacterial agents prepared in each embodiment and each comparative example were tested for their antibacterial rates, and the results were recorded in Table 2 below.

[0073] Table 2 Antibacterial rate results of the antibacterial agents obtained in each embodiment and each comparative example project Staphylococcus aureus (%) Escherichia coli (%) Candida albicans (%) Pseudomonas aeruginosa (%) Example 1 68.3 81.2 72.8 55.1 Example 2 69.2 82.9 73.2 60.6 Example 3 71.6 83.6 75.1 62.4 Example 4 74.8 85.1 78.4 66.7 Example 5 78.6 89.7 81.3 70.5 Comparative Example 1 62.7 74.2 68.5 50.2 Comparative Example 2 60.4 68.6 63.7 45.9 Comparative Example 3 45.1 55.8 50.3 38.6 Comparative Example 4 12.6 14.7 13.5 10.1

[0074] Analyzing the performance test results of Table 2, the antibacterial agent prepared in the embodiment of the present application has a good inhibitory effect on Staphylococcus aureus, Escherichia coli, Candida albicans and Pseudomonas aeruginosa, among which the inhibition rate of Escherichia coli is more than 80%. It can be used in daily toiletries to inhibit the proliferation of antibacterial agents, form effective protection, and protect human health.

[0075] Analysis of the antibacterial rates of Example 1 and Comparative Examples 1 to 4 shows that adding only 18-crown-6 to the solvent and surfactant cannot obtain antibacterial properties, while when triclocarban and 2,4-dichlorobenzyl alcohol lack 18-crown-6, their antibacterial properties are not as good as when the three components are used simultaneously. Therefore, although 18-crown-6 has no antibacterial properties, its use in the formula of triclocarban and 2,4-dichlorobenzyl alcohol can further enhance the antibacterial effect of the antibacterial agent.

[0076] Considering the formulation, the ratio of 2,4-dichlorobenzyl alcohol to 18-crown-6 was changed in Examples 1 to 3. When 2,4-dichlorobenzyl alcohol and 18-crown-6 were in a ratio of 1:1, the antibacterial agent could obtain a better antibacterial effect.

[0077] According to the light industry standard QB / T2738-2012 of the People's Republic of China "Evaluation method for antibacterial and antimicrobial effects of daily chemical products", the antibacterial effect stability test was carried out, and an accelerated test was carried out in a constant temperature box at 54-57°C for 14 days to measure the antibacterial rate, and the results are recorded in Table 3 below.

[0078] Table 3 Antibacterial effect stability test results of each embodiment and each comparative example

[0079] Analyzing the antibacterial effect stability test results in Table 3, the antibacterial agents prepared in the examples of the present application can still maintain good antibacterial properties after the accelerated test, and the reduction in the antibacterial rate is maintained within 10%, and they have good antibacterial stability. However, the antibacterial agents prepared in Comparative Examples 1 to 4 have a significant decrease in antibacterial effect after the accelerated test, and the decrease in the inhibition rate of most microorganisms exceeds 10%.

[0080] The stability of the antibacterial effect of Example 1 and Comparative Examples 1 to 4 was analyzed, and it was found that the antibacterial stability of the compound formula of triclocarban, 2,4-dichlorobenzyl alcohol and 18-crown-6 could be well maintained. It is speculated that the reason is that 18-crown-6 plays a greater role. 18-crown-6 is composed of 12 carbon atoms and 6 oxygen atoms, each of which is connected to two carbon atoms to form a large ring structure. The cavity of 18-crown-6 can accommodate triclocarban and 2,4-dichlorobenzyl alcohol with antibacterial effect, thereby prolonging the duration of its antibacterial effect.

[0081] The antibacterial agent of the present application can have a good inhibitory effect on Staphylococcus aureus, Escherichia coli, Candida albicans and Pseudomonas aeruginosa, and can maintain good antibacterial stability. Its application in daily toiletries can effectively inhibit bacterial proliferation and form effective protection.

[0082] The antibacterial agent of the present application can be added to toiletries such as laundry detergent, hand soap, etc. to inhibit bacterial proliferation, provide protection for users, and improve the hygiene of the toiletries.

[0083] The above describes the basic principles, main features and advantages of the present application. Those skilled in the art should understand that the present application is not limited by the above embodiments, and the above embodiments and the specification only describe the principles of the present application. The present application may have various changes and improvements without departing from the spirit and scope of the present application, and these changes and improvements fall within the scope of the present application for which protection is sought. The scope of protection claimed by the present application is defined by the attached claims and their equivalents.

Claims

1. An antibacterial agent, characterized in that The invention comprises the following components: triclocarban, 2,4-dichlorobenzyl alcohol, 18-crown-6, a surfactant and a solvent.

2. The antibacterial agent according to claim 1, characterized in that The mass ratio of the 2,4-dichlorobenzyl alcohol to the 18-crown-6 is (3:5) to (1:1).

3. The antibacterial agent according to claim 2, characterized in that The mass ratio of the 2,4-dichlorobenzyl alcohol to the 18-crown-6 is 1:

1.

4. The antibacterial agent according to claim 1, characterized in that Calculated by mass fraction, it includes 15% to 30% triclocarban, 3% to 5% 2,4-dichlorobenzyl alcohol, 3% to 5% 18-crown-6, 5% to 10% surfactant and the balance solvent.

5. The antibacterial agent according to claim 1, characterized in that The solvent is polyoxyethylene ether.

6. The antibacterial agent according to claim 1, characterized in that The surfactant is an amphoteric surfactant.

7. The antibacterial agent according to claim 6, characterized in that The amphoteric surfactant is any one or more combinations of betaine type amphoteric surfactant, amino acid type amphoteric surfactant, phosphate betaine, and imidazoline type amphoteric surfactant.

8. The antibacterial agent according to claim 7, characterized in that The amphoteric surfactant is BS-12 dodecyl betaine.

9. A method for preparing an antibacterial agent, characterized in that: The following steps are involved: S1: mixing and heating the surfactant and the solvent in a reaction vessel, followed by dehydration and desalination; S2: Control the reaction temperature, add triclocarban, 2,4-dichlorobenzyl alcohol and 18-crown-6 into the reaction container, stir the reaction for a period of time and then cool to room temperature, filter the product and obtain the antibacterial agent.

10. The method for preparing the antibacterial agent according to claim 9, characterized in that: The reaction temperature is 50-80°C.

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