A long-acting antibacterial compound, a long-acting bactericide, and preparation method and application thereof

Abstract

The present invention relates to a long-acting antibacterial compound, a long-acting bactericide, a preparation method, and applications. The preparation method comprises the following steps: S1. mixing chitin and water, then adding acid to obtain a first mixture; S2. adding an Atractylodes lancea extract to the first mixture, then adding a precipitant and a nonionic stabilizer, stirring, allowing the mixture to stand, removing the supernatant, and freeze-drying to obtain a modified chitin freeze-dried powder; S3. mixing the modified chitin freeze-dried powder with a mixture of an acrylate monomer and water, adding an initiator, and heating to obtain the long-acting antibacterial compound. The long-acting antibacterial compound obtained by this preparation method not only has broad-spectrum antibacterial properties but also exhibits a long-lasting antibacterial effect.

Description

Technical Field

[0001] The present invention relates to the technical field of long-acting antibacterial skin care products, and more specifically, to a long-acting antibacterial compound, a long-acting bactericide, a preparation method and applications thereof. Background Art

[0002] With the improvement of living standards, people are paying more and more attention to their health. However, life is almost everywhere, filled with various microorganisms and bacteria, which seriously affect people's health. Currently, common disinfection and sterilization products on the market include ethanol disinfectants and quaternary ammonium disinfectants. However, the bactericidal effect of these disinfectants is short-lived and cannot achieve long-term antibacterial effect. Disinfection requires frequent operations, increasing disinfection costs and daily disinfection time. Therefore, there is an urgent need to develop disinfectants with long-term antibacterial function, so that they can achieve long-term antibacterial effect and reduce the disinfection workload.

[0003] A Chinese patent entitled "A Spray-Type Long-Acting Fungicide and Its Preparation Method" provides a spray-type long-acting fungicide, but the sterilization time of the spray-type long-acting fungicide is still relatively short. Summary of the Invention

[0004] The primary purpose of the present invention is to overcome the problem of short antibacterial time of current bactericides and provide a method for preparing a long-acting antibacterial compound. The long-acting antibacterial compound obtained by this preparation method not only has broad-spectrum antibacterial properties but also has a long-lasting antibacterial effect.

[0005] A further object of the present invention is to provide a long-acting antibacterial compound.

[0006] A further object of the present invention is to provide the use of the long-acting antibacterial compound in the preparation of a bactericide.

[0007] A further object of the present invention is to provide a long-acting antibacterial agent.

[0008] A further object of the present invention is to provide a method for preparing the long-acting antibacterial agent.

[0009] The above-mentioned purpose of the present invention is achieved through the following technical solutions:

[0010] A method for preparing a long-acting antibacterial compound comprises the following steps:

[0011] S1. Mixing chitosan and water, and then adding acid to obtain a first mixture;

[0012] S2. The Atractylodes lancea extract was added to the first mixture, and then a precipitant and a non-ionic stabilizer were added, stirred, allowed to stand, the supernatant was removed, and lyophilized to obtain a modified chitin lyophilized powder;

[0013] S3. Mixing the modified chitin freeze-dried powder with a mixture of acrylate monomer and water, adding an initiator, and heating to obtain the long-acting antibacterial complex.

[0014] The present invention first combines chitin with an Atractylodes lancea extract to produce modified chitin. The modified chitin is then mixed with acrylic acid esters, and the resulting long-lasting antibacterial compound has a core-shell structure with the acrylic acid ester as the shell and the modified chitin as the core. When the long-lasting antibacterial compound is applied to the surface of human skin, the shell portion exhibits excellent film-forming properties and stability, allowing for long-term adsorption on the skin surface. On this basis, the modified chitin in the core portion allows for sustained release and maintains a highly effective bactericidal effect. The Atractylodes lancea extract has broad-spectrum antibacterial properties, thus achieving a long-lasting antibacterial effect.

[0015] The long-acting antibacterial compound obtained by the preparation method of the present invention not only has broad-spectrum antibacterial properties, but also has a long-acting antibacterial effect.

[0016] Preferably, the purity of the chitosan in step S1 is 85-99.9%.

[0017] When the purity of chitosan is within this range, the long-acting antibacterial compound has a longer antibacterial effect.

[0018] Preferably, the Atractylodes lancea extract in step S2 is a water extract of Atractylodes lancea.

[0019] Preferably, the acid in step S1 is glacial acetic acid.

[0020] Typically, the amount of acid added in step S1 is: 0.1 to 0.5 g of acid per gram of chitosan.

[0021] Preferably, the nonionic stabilizer in step S2 is at least one of propylene glycol alginate or polyglycerol fatty acid ester.

[0022] More preferably, the nonionic stabilizer in step S2 is propylene glycol alginate.

[0023] In the present invention, the amount of the nonionic stabilizer added is: based on the mass of chitosan, 1.5 mL of a nonionic stabilizer solution with a concentration of 10-15 wt% is added to each 1 g of chitosan.

[0024] By selecting propylene glycol alginate as a non-ionic stabilizer, the obtained long-lasting antibacterial compound has a higher antibacterial rate against Escherichia coli, Staphylococcus aureus and Candida albicans, and has a longer antibacterial effect.

[0025] Preferably, the precipitant in step S2 is at least one of a phosphate aqueous solution, a citrate aqueous solution or a phytic acid aqueous solution.

[0026] In the present invention, the amount of the precipitant added is: based on the mass of chitosan, 15 mL of the precipitant with a concentration of 25-35 wt% is added to each gram of chitosan.

[0027] Specifically, the specific process of heating in step S3 is: first heating at 65-75° C. for 4-6 minutes, and then heating at 80-90° C. for 55-65 minutes.

[0028] Typically, in the mixed solution of the acrylic acid ester monomer and water in step S3, the mass ratio of water to the acrylic acid ester monomer is 1:(0.17-0.67).

[0029] Typically, the acrylate monomer in step S3 is at least one of butyl acrylate or methyl methacrylate.

[0030] Typically, the initiator in step S3 is at least one of ammonium persulfate or potassium persulfate.

[0031] Typically, the amount of the initiator added in step S3 is: 0.08 to 0.125 g of initiator per gram of acrylate monomer.

[0032] Preferably, the mass ratio of the chitin in step S1, the Atractylodes lancea extract in step S2, and the acrylate monomer in step S3 is (20-25):(11-16):(15-18).

[0033] A long-acting antibacterial compound is prepared by the above preparation method.

[0034] The use of the above-mentioned long-acting antibacterial compound in the preparation of a bactericide is also within the scope of protection of the present invention.

[0035] A long-acting fungicide comprising the following components in percentage by mass:

[0036] 1-10% of the above-mentioned long-acting antibacterial compound,

[0037] Functional additives 2.55~7.2%,

[0038] Water 82.8~96.45%.

[0039] Preferably, the functional auxiliary agent is at least one of a moisturizer, a surfactant or a pH regulator.

[0040] Moisturizers, surfactants and pH adjusters commonly used in the art can be used in the present invention.

[0041] Optionally, the moisturizing agent is at least one of glycerol, polymerized glycerol, xylitol glucoside, avocado oil or propylene glycol.

[0042] Preferably, the moisturizing agent is a composite moisturizing agent composed of glycerin and avocado oil in a mass ratio of 1:(0.2-0.4).

[0043] Optionally, the surfactant is at least one of decyl glucoside, polysorbate 20 or cocamidopropyl betaine.

[0044] Preferably, the surfactant is a composite surfactant composed of decyl glucoside and cocamidopropyl betaine in a mass ratio of 1:(0.4-0.7).

[0045] Preferably, the pH adjuster is triethanolamine.

[0046] The preparation method of the above-mentioned long-acting fungicide comprises the following steps:

[0047] S4. Mix and stir the components to obtain the long-acting fungicide.

[0048] Specifically, the preparation method of the long-acting fungicide of the present invention is as follows: mixing a pH regulator and water to form a regulating solution; mixing a moisturizer, a surfactant and water, stirring, and then adding a long-acting antibacterial complex and stirring to obtain a mixed material; mixing the regulating solution and the mixed material and stirring to obtain the long-acting fungicide.

[0049] Compared with the prior art, the present invention has the following beneficial effects:

[0050] The present invention first combines chitin with an Atractylodes lancea extract to produce modified chitin. The modified chitin is then mixed with acrylic acid esters, and the resulting long-lasting antibacterial compound has a core-shell structure with the acrylic acid ester as the shell and the modified chitin as the core. When the long-lasting antibacterial compound is applied to the surface of human skin, the shell portion exhibits excellent film-forming properties and stability, allowing for long-term adsorption on the skin surface. On this basis, the modified chitin in the core portion allows for sustained release and maintains a highly effective bactericidal effect. The Atractylodes lancea extract has broad-spectrum antibacterial properties, thus achieving a long-lasting antibacterial effect. DETAILED DESCRIPTION

[0051] In order to more clearly and completely describe the technical solution of the present invention, the present invention is further described in detail through specific embodiments below. 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. Various changes can be made within the scope of the rights of the present invention.

[0052] Some of the reagents selected in the embodiments and comparative examples of the present invention are described as follows:

[0053] Chitosan 1#: purity 99%, brand: HS-1150, purchased from Xi'an Heshun Biotechnology Co., Ltd.

[0054] Chitosan 2#: purity 95%, brand: tk-055, purchased from Peptide Kang (Shaanxi) Health Industry Co., Ltd.

[0055] Chitosan 3#: purity 90%, brand: 453543, purchased from Shanghai Gaoming Chemical Co., Ltd.

[0056] Chitosan 4#: purity of 85%, brand: AL-563309214360, purchased from Shandong Xuanyang Biotechnology Co., Ltd.

[0057] Atractylodes lancea extract: Atractylodes lancea water extract, brand: RGCZ, solid powder, purchased from Shaanxi Ruilin Panier Biotechnology Co., Ltd.;

[0058] Acrylate monomer: butyl acrylate, purity: 99%, brand: Wanhua;

[0059] Acid: anhydrous glacial acetic acid, commercially available;

[0060] Precipitating salt: sodium citrate, purity 99%, commercially available;

[0061] Initiator: ammonium persulfate, 99% purity, commercially available;

[0062] Nonionic stabilizer 1#: propylene glycol alginate, brand: 102, purchased from Jiangsu Fushengde Bioengineering Co., Ltd.;

[0063] Nonionic stabilizer 2#: polyglycerol fatty acid ester, brand: jgyzfsz, purchased from Zhejiang Qinuo Food Ingredients Co., Ltd.

[0064] Moisturizer: glycerin and avocado oil mixed in a mass ratio of 18:5, commercially available;

[0065] Surfactant: Decyl glucoside and cocamidopropyl betaine mixed in a mass ratio of 3:2, commercially available;

[0066] pH adjuster: triethanolamine, commercially available;

[0067] Unless otherwise specified, the components (eg, moisturizers, surfactants) used in the parallel embodiments, comparative examples, application examples, and application comparative examples are all the same commercially available products.

[0068] Example 1

[0069] This embodiment provides a method for preparing a long-acting antibacterial compound, comprising the following steps:

[0070] S1. 20g of chitosan 1# was added to 280mL of water, mixed, and then 5g of anhydrous glacial acetic acid was added to obtain a first mixture;

[0071] S2. The Atractylodes lancea extract was added to the first mixture and mixed uniformly, and then 300 mL of a 25 wt% sodium citrate solution (precipitant) and 30 mL of a 10 wt% aqueous solution of propylene glycol alginate (non-ionic stabilizer 1#) were added at a rate of 3 mL / min, stirred for 40 min, allowed to stand, the supernatant removed, frozen, and freeze-dried to obtain a modified chitin freeze-dried powder;

[0072] S3. The modified chitin freeze-dried powder obtained in S2 was mixed with a mixture of acrylate monomer and water (the mass ratio of acrylate monomer to water was 1:3) and 1.5 g of ammonium persulfate. The mixture was heated at 75°C for 5 minutes, then at 80°C for 60 minutes, and cooled to obtain a long-acting antibacterial compound 1#.

[0073] Wherein, the mass ratio of the chitin in step S1, the Atractylodes lancea extract in step S2, and the acrylate monomer in step S3 is 22:13:17;

[0074] Finally, the long-acting antibacterial compound 1# was obtained in this embodiment.

[0075] Example 2

[0076] This embodiment provides a method for preparing a long-acting antibacterial compound, which differs from Example 1 in that:

[0077] The mass ratio of the chitin in step S1, the Atractylodes lancea extract in step S2, and the acrylate monomer in step S3 is 25:11:15.

[0078] Finally, the long-acting antibacterial compound 2# was obtained in this example.

[0079] Example 3

[0080] This embodiment provides a method for preparing a long-acting antibacterial compound, which differs from Example 1 in that:

[0081] The mass ratio of the chitin in step S1, the Atractylodes lancea extract in step S2, and the acrylate monomer in step S3 is 20:16:18.

[0082] Finally, the long-acting antibacterial compound 3# was obtained in this example.

[0083] Example 4

[0084] This embodiment provides a method for preparing a long-acting antibacterial compound, which differs from Example 1 in that:

[0085] S1. 20g of chitosan 1# was added to 280mL of water, mixed, and then 5g of anhydrous glacial acetic acid was added to obtain a first mixture;

[0086] S2. The Atractylodes lancea extract was added to the first mixture and mixed uniformly, and then 300 mL of a 35 wt% sodium citrate solution (precipitant) and 30 mL of a 15 wt% aqueous solution of propylene glycol alginate (non-ionic stabilizer 1#) were added at a rate of 10 mL / min, stirred for 40 min, allowed to stand, the supernatant removed, frozen, and freeze-dried to obtain a modified chitin freeze-dried powder;

[0087] S3. The modified chitin freeze-dried powder obtained in S2 was mixed with a mixture of acrylate monomer and water (the mass ratio of acrylate monomer to water was 1:3) and 1.5 g of ammonium persulfate. The mixture was heated at 65°C for 4 min, then at 80°C for 55 min, and cooled to obtain a long-acting antibacterial compound 4#.

[0088] Wherein, the mass ratio of the chitin in step S1, the Atractylodes lancea extract in step S2, and the acrylate monomer in step S3 is 22:13:17;

[0089] Finally, the long-acting antibacterial compound 4# was obtained in this example.

[0090] Example 5

[0091] This embodiment provides a method for preparing a long-acting antibacterial compound, which differs from Example 1 in that:

[0092] S1. 20g of chitosan 1# was added to 280mL of water, mixed, and then 5g of anhydrous glacial acetic acid was added to obtain a first mixture;

[0093] S2. The Atractylodes lancea extract was added to the first mixture and mixed uniformly, and then 300 mL of a 25 wt% sodium citrate solution (precipitant) and 30 mL of a 10 wt% aqueous solution of propylene glycol alginate (non-ionic stabilizer 1#) were added at a rate of 3 mL / min, stirred for 40 min, allowed to stand, the supernatant removed, frozen, and freeze-dried to obtain a modified chitin freeze-dried powder;

[0094] S3. The modified chitin freeze-dried powder obtained in S2 was mixed with a mixture of acrylate monomer and water (the mass ratio of acrylate monomer to water was 1:3) and 1.5 g of ammonium persulfate. The mixture was heated at 75°C for 6 min, then at 90°C for 65 min, and cooled to obtain a long-acting antibacterial compound 5#.

[0095] The mass ratio of the chitin in step S1, the atractylodes extract in step S2, and the acrylate monomer in step S3 is 22:13:17.

[0096] Finally, the long-acting antibacterial compound 5# was obtained in this example.

[0097] Example 6

[0098] This embodiment provides a method for preparing a long-acting antibacterial compound, which differs from embodiment 1 in that chitosan 1# in embodiment 1 is replaced with chitosan 2#. This embodiment finally obtains a long-acting antibacterial compound 6#.

[0099] Example 7

[0100] This embodiment provides a method for preparing a long-acting antibacterial compound, which differs from embodiment 1 in that chitosan 1# in embodiment 1 is replaced with chitosan 3#. This embodiment finally obtains a long-acting antibacterial compound 7#.

[0101] Example 8

[0102] This embodiment provides a method for preparing a long-acting antibacterial compound, which differs from embodiment 1 in that chitosan 1# in embodiment 1 is replaced with chitosan 4#. This embodiment finally obtains a long-acting antibacterial compound 8#.

[0103] Example 9

[0104] This example provides a method for preparing a long-acting antibacterial compound, which differs from Example 1 in that the nonionic stabilizer 1# in Example 1 is replaced with nonionic stabilizer 2#. This example ultimately produces a long-acting antibacterial compound 9#.

[0105] Comparative Example 1

[0106] This comparative example provides a method for preparing an antibacterial compound, which differs from Example 1 in that step S3 is not performed. This comparative example ultimately yields an antibacterial compound 1#.

[0107] Comparative Example 2

[0108] This comparative example provides a method for preparing an antibacterial composite, which differs from Example 1 in that no nonionic stabilizer 1# is added in step S2. This comparative example ultimately yields an antibacterial composite 2#.

[0109] Comparative Example 3

[0110] This comparative example provides a method for preparing an antibacterial composite, comprising the following steps: mixing an Atractylodes lancea extract with a mixture of an acrylate monomer and water (the mass ratio of the acrylate monomer to the water is 1:3) and ammonium persulfate (the mass ratio of the acrylate monomer to the ammonium persulfate is 1:0.097), heating at 75°C for 5 minutes, then heating at 80°C for 60 minutes, and cooling to obtain an antibacterial composite;

[0111] The mass ratio of the Atractylodes lancea extract to the acrylate monomer is 13:17.

[0112] This comparative example finally obtained antibacterial compound 3#.

[0113] Comparative Example 4

[0114] This comparative example provides a method for preparing an antibacterial composite, comprising the following steps: chitin 1#, atractylodes lancea extract, a mixture of acrylate monomer and water, and ammonium persulfate are used in the same amount as in Example 1, the four are directly mixed, heated at 75°C for 5 minutes, then heated at 80°C for 60 minutes, and cooled to obtain the composite.

[0115] This comparative example finally obtained antibacterial compound 4#.

[0116] Application Examples 1-11

[0117] Application Examples 1 to 11 provide a series of long-acting fungicides, the formulations of which are shown in Table 1. The preparation method of the long-acting fungicides in each application example comprises the following steps:

[0118] (1) At room temperature, stir the pH adjuster and water for 5 minutes to form a pH adjustment solution;

[0119] (2) the moisturizer, surfactant, and water were sealed and stirred for 8 minutes, and then the long-acting antibacterial composition was added, and the mixture was sealed and stirred for 25 minutes to obtain a mixed material;

[0120] (3) Mix the adjusted solution with the mixed material, add enough water, seal and stir for 20 minutes to obtain a long-acting fungicide.

[0121] Table 1 Formulations of Application Examples 1 to 11 (mass percentage, %)

[0122]

[0123] Comparative Application Example 1

[0124] This comparative example provides a fungicide, which differs from Application Example 1 in that the long-acting antibacterial compound 1# is replaced with the antibacterial compound 1#.

[0125] Application Comparative Example 2

[0126] This comparative example provides a fungicide, which differs from Application Example 1 in that the long-acting antibacterial compound 1# is replaced with the antibacterial compound 2#.

[0127] Application Comparative Example 3

[0128] This comparative example provides a fungicide, which differs from Application Example 1 in that the long-acting antibacterial compound 1# is replaced with the antibacterial compound 3#.

[0129] Comparative Application Example 4

[0130] This comparative example provides a fungicide, which differs from Application Example 1 in that the long-acting antibacterial compound 1# is replaced with the antibacterial compound 4#.

[0131] Application Comparative Example 5

[0132] This comparative example provides a fungicide, which differs from Application Example 1 in that the long-acting antibacterial compound 1# is replaced with an Atractylodes lancea extract.

[0133] Performance Testing

[0134] The performance of the long-lasting fungicide of each application example and the fungicide of each comparative application example was tested. The specific test items and test methods are as follows:

[0135] (1) Sterilization test: According to the requirements of the 2002 edition of the "Technical Specifications for Disinfection" issued by the Ministry of Health, the sterilization tests were carried out on Staphylococcus aureus, Escherichia coli, and Candida albicans, and the sterilization rates of Staphylococcus aureus, Escherichia coli, and Candida albicans were calculated.

[0136] (2) Antibacterial effective action time test: The sustained antibacterial effective action time test was carried out according to the sustained antibacterial test operation method in the standard WS / T 650-2019.

[0137] The test results are shown in Table 2.

[0138] Table 2 Performance test results of various application examples and comparative application examples

[0139]

[0140]

[0141] From Table 2 we can see that:

[0142] The long-acting bactericides of Application Examples 1 to 11 have excellent bactericidal effects on Escherichia coli, Staphylococcus aureus and Candida albicans. Specifically, the bactericidal rate against Escherichia coli reaches more than 94.92%, the bactericidal rate against Staphylococcus aureus reaches more than 94.96%, and the bactericidal rate against Candida albicans reaches more than 85.74%, and the effective antibacterial effect time reaches more than 175 days, indicating that the long-acting antibacterial composite obtained by the preparation method of the present invention not only has broad-spectrum antibacterial properties, but also has a long-lasting antibacterial effect.

[0143] The antibacterial compound 1# added in Comparative Example 1 is a modified chitin, rather than a long-acting antibacterial compound with a core-shell structure. The bactericidal rate of its bactericide against Escherichia coli, Staphylococcus aureus and Candida albicans is low, and the antibacterial time is very short. In Comparative Example 2, antibacterial compound 2# is added. No nonionic stabilizer is added during the preparation of antibacterial compound 2#. The bactericidal rate of its bactericide against Escherichia coli, Staphylococcus aureus and Candida albicans is low, and the antibacterial time is short. In Comparative Example 3, antibacterial compound 3# is added. No chitin is added during the preparation of antibacterial compound 3#. The bactericidal rate of its bactericide against Escherichia coli, Staphylococcus aureus and Candida albicans is low, and the antibacterial time is short. In Comparative Example 4, antibacterial compound 4# was added. Antibacterial compound 4# was obtained by directly mixing chitin, atractylodes extract, and a mixture of acrylate monomer and water. It was unable to form a long-lasting antibacterial compound with a stable core-shell structure. The bactericidal rate of its bactericide against Escherichia coli, Staphylococcus aureus, and Candida albicans was low, and the antibacterial effect was short. In Comparative Example 5, the atractylodes extract was directly added. The bactericidal rate of its bactericide against Escherichia coli, Staphylococcus aureus, and Candida albicans was low, and the antibacterial effect was short.

[0144] Obviously, the above embodiments of the present invention are merely examples for the purpose of clearly illustrating the present invention, and are not intended to limit the embodiments of the present invention. Those skilled in the art will appreciate that other variations or modifications can be made based on the above description. It is not necessary and impossible to enumerate all embodiments here. Any modifications, equivalent substitutions, and improvements made within the spirit and principles of the present invention shall be included within the scope of protection of the claims of the present invention.

Claims

1. A method for preparing a long-acting antibacterial compound, characterized in that: The steps include: S1. Mixing chitosan and water, and then adding acid to obtain a first mixture; S2. The Atractylodes lancea extract was added to the first mixture, followed by addition of a citrate aqueous solution and a nonionic stabilizer, stirred, allowed to stand, the supernatant removed, and lyophilized to obtain a modified chitin freeze-dried powder; S3. The modified chitin freeze-dried powder was mixed with a mixture of acrylate monomer and water, an initiator was added, and heated to obtain the long-lasting antibacterial complex; Wherein, the nonionic stabilizer in step S2 is at least one of propylene glycol alginate or polyglycerol fatty acid ester.

2. The preparation method according to claim 1, characterized in that The purity of the chitosan in step S1 is 85-99.9%.

3. The preparation method according to claim 1, characterized in that: The Atractylodes lancea extract in step S2 is a water extract of Atractylodes lancea.

4. The preparation method according to claim 1, characterized in that The mass ratio of the chitin in step S1, the Atractylodes lancea extract in step S2 and the acrylate monomer in step S3 is (20-25):(11-16):(15-18).

5. A long-acting antibacterial compound, characterized in that: It is prepared by the preparation method according to any one of claims 1 to 4.

6. Use of the long-acting antibacterial compound according to claim 5 in the preparation of a bactericide.

7. A long-acting fungicide, characterized in that: The following components are included in mass percentage: 1-10% of the long-acting antibacterial compound according to claim 5, Functional additives 2.55~7.2%, Water 82.8~96.45%.

8. The long-acting fungicide according to claim 7, characterized in that: The functional auxiliary agent is at least one of a moisturizing agent, a surfactant or a pH regulator.

9. The method for preparing the long-acting fungicide according to any one of claims 7 to 8, characterized in that: The steps include: S4. Mix and stir the components to obtain the long-acting fungicide.

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