Polyquaternary ammonium salt bacteriostatic agent, preparation method thereof and antibacterial liquid detergent applied to polyquaternary ammonium salt bacteriostatic agent
By introducing carboxylic acid groups into the polyquaternary ammonium salt structure, its compatibility and stability in anionic surfactant systems are improved, solving the problem of poor antifungal effect of existing detergents and achieving highly efficient antibacterial activity in hard water environments.
Patent Information
- Application Number
- CN202511750964.2
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2025-11-26
- Publication Date
- 2026-02-24
AI Technical Summary
Existing detergents are ineffective at inhibiting fungi, especially Candida albicans, and quaternary ammonium salt antibacterial agents have poor compatibility in anionic surfactant systems, resulting in decreased bactericidal performance in hard water environments.
To develop a novel anhydride-modified polyquaternary ammonium salt antibacterial agent, the introduction of carboxylic acid groups to improve its compatibility and stability in anionic surfactant systems, enhance hydrophilicity, reduce cytotoxicity, and improve antifungal efficacy.
In systems containing high concentrations of anionic surfactants, polyquaternary ammonium salt antibacterial agents exhibit excellent antifungal activity, solving the compatibility and stability issues of quaternary ammonium salt antibacterial agents and improving the sterilization effect of antibacterial liquid detergents.
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Figure CN121554733A_ABST
Abstract
Description
Technical Field
[0001] This invention relates to the field of daily chemical products technology, to a polyquaternary ammonium salt antibacterial agent and its preparation method, and particularly to a novel polyquaternary ammonium salt, its synthesis, and its application in antibacterial liquid detergents. Background Technology
[0002] As people's living standards improve, their demands for hygiene in their living environment are also increasing. Therefore, in the daily chemical cleaning industry, in addition to existing conventional detergents, products with antibacterial effects on fabrics and hard surfaces are receiving more and more attention from consumers.
[0003] In the daily detergent industry, fungal inhibition has always been a challenging issue, especially against Candida albicans. Due to its unique cell wall structure and physiological characteristics, Candida albicans exhibits strong resistance to conventional antibacterial agents. These fungi can survive in various environments and form biofilms, further increasing their tolerance to antimicrobial agents. Most daily detergents on the market currently target bacteria, with relatively limited effectiveness against fungi, particularly Candida albicans. This is because traditional antibacterial ingredients, such as quaternary ammonium salts and phenolic compounds, lack sufficient penetration into fungal cell membranes, making it difficult to effectively inhibit their growth and reproduction. Research on antibacterial ingredients, especially cationic antibacterial materials, has become a current research hotspot. These antibacterial agents interact strongly with negatively charged pathogenic microorganisms through contact charge action, without damaging electrically neutral mammalian cells, thus effectively reducing the toxicity of antibacterial agents to mammals during use. Quaternary ammonium salt antibacterial agents, as a class of cationic surfactant-type antibacterial agents, have low antibacterial concentrations, stable chemical properties, no corrosive or bleaching effects, and low skin and tissue irritation, making them suitable for use in home environments. However, as typical cationic surfactants, the application of quaternary ammonium salt bactericides is subject to many limitations due to ingredient compatibility and usage conditions. For example, quaternary ammonium salt bactericides are incompatible with anionic surfactants, while current liquid detergent formulations typically use anionic surfactants as the main component. Furthermore, in hard water environments, the bactericidal performance of quaternary ammonium salt bactericides decreases significantly. These limitations severely restrict their widespread application in household antibacterial products. For example, CN201610307397.8 discloses an antibacterial fabric detergent and its preparation method, which uses quaternary ammonium salt bactericides, nonionic surfactants, amphoteric surfactants, and other components to prepare a detergent with dual detergency and bactericidal effects; this detergent does not contain anionic surfactants. CN113854295A discloses an antibacterial composition that uses polyquaternary ammonium salts and quaternary ammonium salt compositions as antibacterial agents, maintaining a certain antibacterial function even in the presence of small amounts of anionic surfactants and hard water. However, the washing composition used in this patent has an anionic surfactant content controlled at 2%-3%, and the data for the anionic surfactant system only includes data against Staphylococcus aureus, indicating a narrow antibacterial spectrum.
[0004] Therefore, developing novel polyquaternary ammonium salt antibacterial agents that can effectively inhibit these stubborn fungi will bring significant breakthroughs to the laundry industry, not only improving product performance but also providing consumers with more comprehensive hygiene protection. Summary of the Invention
[0005] The purpose of this invention is to provide a novel polyquaternary ammonium salt compound and its synthesis method, as well as a liquid detergent using this polyquaternary ammonium salt compound as an antibacterial agent. This liquid detergent can contain a high concentration of anionic surfactants, and the polyquaternary ammonium salt antibacterial agent provided by this invention still exhibits excellent antifungal growth effects in systems containing high concentrations of anionic surfactants.
[0006] The objective of this invention is achieved through the following technical solutions.
[0007] A polyquaternary ammonium salt antibacterial agent is provided, which is a polyquaternary ammonium salt having repeating units of the following formula I; Formula I; Where R is or X is CH3SO4, CH3CH2SO4 or a halogen.
[0008] Preferably, the molecular weight of the repeating unit accounts for more than 70% of the molecular weight of the polyquaternary ammonium salt.
[0009] Preferably, the weight-average molecular weight of the polyquaternary ammonium salt is 2,000-400,000.
[0010] The preparation method of the polyquaternary ammonium salt antibacterial agent of the present invention includes the following steps: dissolving polyhexamethylene biguanide salt in the solvent N,N-dimethylformamide, adding triethylamine to adjust the solution system to alkalinity; then adding 1-1.5 times the equivalent of the amino anhydride in the polyhexamethylene biguanide salt, heating to 35-40℃ and stirring for 14-18h; then adding acid to quench the reaction and neutralize the reaction solution; finally adding acetonitrile to the reaction solution to precipitate the product, collecting the precipitate to obtain the polyquaternary ammonium salt antibacterial agent; the anion in the polyhexamethylene biguanide salt is one of halide anion, methanesulfonic acid anion, ethylsulfonic acid anion, and sulfate anion; the anhydride is selected from succinic anhydride or phthalic anhydride.
[0011] Preferably, the acid solution is selected from hydrochloric acid, sulfuric acid, methanesulfonic acid, and ethylsulfonic acid solutions. In specific implementations, the choice of acid solution corresponds to the anion in the polyhexamethylene biguanide salt. For example, if the anion in the polyhexamethylene biguanide salt is a methanesulfonic acid anion, then the acid solution is methanesulfonic acid.
[0012] In some specific embodiments (as described in the examples below), the preparation method of the polyquaternary ammonium salt antibacterial agent is as follows: 2.5 g of polyhexamethylene biguanide hydrochloride is weighed and dissolved in the solvent N,N-dimethylformamide, and 3.5 g of triethylamine is added to adjust the solution system to alkalinity; then, 1.25 times the equivalent of the amino anhydride in polyhexamethylene biguanide hydrochloride is added, and the mixture is heated to 38°C and stirred for 16 h; then, hydrochloric acid is added to quench the reaction and neutralize the reaction solution; finally, acetonitrile is added to the reaction solution to precipitate the product, and the precipitate is collected to obtain the polyquaternary ammonium salt antibacterial agent.
[0013] The polyquaternary ammonium salt antibacterial agent of this invention is a novel polyquaternary ammonium salt modified with acid anhydride. A carboxylic acid group is introduced into the molecular structure of polyhexamethylene biguanide. Compared with the known polyquaternary ammonium salt antibacterial agent polyhexamethylene biguanide, it has the following advantages: 1) The carboxylic acid group ionizes into a negative charge (-COO) in solution. - ), which forms an intramolecular electrostatic balance with the positive charge of the quaternary ammonium salt group, reducing the overall positive charge; 2) Improve solubility and stability: Reduce precipitation tendency caused by strong cationicity and enhance compatibility in electrolyte solutions (such as hard water); 3) Enhanced hydrophilicity: The strong polarity of the carboxyl group significantly enhances the hydrophilicity of the molecule and improves water solubility; 4) Reduce cytotoxicity: weaken the damaging effect of strong cations on cell membranes and improve biocompatibility; 5) Synergistic effect of compounding: When combined with anionic surfactants, intramolecular charge neutralization reduces precipitation and improves system stability.
[0014] This invention also provides an antibacterial liquid detergent, comprising the polyquaternary ammonium salt antibacterial agent as described above. The antibacterial liquid detergent of this invention features bactericidal effects and strong resistance to hard water and anionic surfactants. Compared to other quaternary ammonium salt bactericides that deactivate upon contact with anionic surfactants, the polyquaternary ammonium salt antibacterial agent of this invention can exert excellent antibacterial effects in systems containing high concentrations of anionic surfactants, with particularly outstanding inhibitory ability against fungi (Candida albicans), and is compatible with the anionic surfactant formulations of most laundry detergents on the market.
[0015] Preferably, the antibacterial liquid detergent comprises, by weight percentage, the following components: 1-5% of the polyquaternary ammonium salt antibacterial agent, 15-17% of the surfactant, 0.2-10% of the detergent additive, and the balance being water.
[0016] Preferably, the surfactant is selected from at least one of nonionic surfactants, anionic surfactants, and amphoteric surfactants.
[0017] Preferably, the anionic surfactant is a non-soap anionic surfactant; specifically, the anionic surfactant is selected from linear alkylbenzene sulfonates, fatty alcohol polyoxyethylene ether sulfates, fatty alcohol polyoxyethylene ether carboxylates, α-alkenyl sulfonates, and fatty acid methyl ester sulfonates; the fatty alcohol polyoxyethylene ether sulfate contains 2 or 3 EO chains; the fatty alcohol polyoxyethylene ether carboxylate contains 7 or 9 EO chains. More preferably, the anionic surfactant content in the antibacterial liquid detergent is 10-12%. The polyquaternary ammonium salt antibacterial agent of the present invention significantly improves the resistance to hard water and surfactant interference. Therefore, in the present invention, the antibacterial liquid detergent may also contain anionic surfactants, nonionic surfactants, and amphoteric surfactants. The amount of surfactant can be specifically set according to the washing requirements, and it still has a bactericidal effect when containing an appropriate amount of anionic surfactant.
[0018] The nonionic surfactant is selected from one or more of fatty alcohol ethoxylates, fatty acid methyl ester ethoxylates, alkyl polysaccharides, alkyl alcohol amides, and ethoxylated sorbitan fatty acid esters.
[0019] The zwitterionic surfactant comprises one or more of the following: betaine-type surfactants, imidazoline-type surfactants, amino acid-type surfactants, and amine oxide-type surfactants, including but not limited to: alkyl betaine, fatty amide betaine, fatty amide propyl betaine, fatty amide propyl hydroxypropyl sulfonated betaine, sodium alkyl acetate imidazoline, fatty acid imidazoline, sulfonic acid imidazoline, aminopropionic acid derivatives, glycine derivatives, alkyl dimethyl amine oxide, fatty amide propyl dimethyl amine oxide, etc.
[0020] Preferably, the detergent additives refer to other auxiliary materials in detergents besides surfactants and water, including one or more of fillers, excipients, anti-redeposition agents, chelating agents, enzymes, pH adjusters, viscosity adjusters, preservatives, pigments, optical brighteners, and fragrances. The selection of detergent additives varies greatly among different types of detergents; these are well known to those skilled in the art and can be rationally formulated using conventional methods.
[0021] Quaternary ammonium salt antibacterial agents adsorb onto bacterial surfaces using their positively charged bodies, forming micro-clusters. These micro-clusters then insert into the bacterial lipid layer via hydrophobic groups, altering cell membrane permeability, disrupting cell structure, affecting bacterial metabolism, and ultimately leading to bacterial death. Because quaternary ammonium salt antibacterial agents are cationic surfactants, they generally cannot be mixed with anionic surfactants, and their effectiveness decreases significantly under hard water conditions, limiting their application in household disinfection products. It is widely believed in the industry that quaternary ammonium salt antibacterial agents cannot be combined with anionic surfactants, primarily due to their chemical interactions. When these two components are mixed, ionic bonds form, leading to insoluble precipitates or reduced activity, thus affecting the efficacy of the quaternary ammonium salt antibacterial agent. Sulfonic acid anionic surfactants exhibit even worse compatibility with quaternary ammonium salt compounds. This is because sulfonic acid groups have strong hydrophilicity and electronegativity, making it easier for them to combine with the cationic portion of quaternary ammonium salts to form stable complexes or precipitates, further weakening the antibacterial agent's function. Therefore, in formulation design, if these two ingredients need to be used simultaneously, special attention should be paid to optimizing their ratio and compatibility to avoid performance degradation.
[0022] In the daily detergent industry, inhibiting fungi, especially Candida albicans, is a challenge. Candida albicans exhibits strong resistance to conventional antibacterial agents due to its unique cell wall and physiological characteristics. This type of fungus can not only survive in various environments but also form biofilms, enhancing its tolerance. Currently, detergents on the market primarily target bacteria, with limited effectiveness against Candida albicans because traditional antibacterial ingredients such as quaternary ammonium salts and phenolic compounds struggle to effectively penetrate the fungal cell membrane and prevent its growth and reproduction. However, the antibacterial liquid detergent of this invention, in a surfactant system with sulfonic acid anionic surfactants as the main active ingredient, achieves an inhibition rate of over 90% against both fungi (Candida albicans) and bacteria (Staphylococcus aureus), and the system remains stable even when the sulfonic acid anionic surfactant content reaches 12 wt%.
[0023] Compared with the prior art, the beneficial effects of the present invention are: 1) The polyquaternary ammonium salt antibacterial agent of the present invention has excellent antibacterial ability against a variety of microorganisms, especially fungi such as Candida albicans.
[0024] 2) Based on the structure of common polyquaternary ammonium salt cationic antibacterial agents, this invention has chemically modified and synthesized a novel polyquaternary ammonium salt antibacterial agent. The physicochemical properties of polyquaternary ammonium salt have been improved, enabling it to be well-combined with common anionic surfactants on the market. It still has excellent bactericidal effects at low concentrations, strong resistance to interference from hard water and surfactants, and can maintain activity in systems containing high concentrations of sulfonic acid-type anionic surfactants. Under the same system, it exhibits better antibacterial performance than quaternary ammonium salt antibacterial agents and unmodified polyquaternary ammonium salts. This invention overcomes the limitations of existing quaternary ammonium salt antibacterial agents, promotes the development of new antibacterial and bactericidal products, meets people's health and hygiene needs, and has important scientific significance and application value. Attached Figure Description
[0025] To more clearly illustrate the technical solutions of the embodiments of the present invention, the drawings used in the following description of the embodiments will be briefly introduced. Obviously, the drawings described below are some embodiments of the present invention. For those skilled in the art, other drawings can be obtained based on these drawings without creative effort.
[0026] Figure 1 The sample of antibacterial liquid detergent from Example 8 is after ultrasonic treatment.
[0027] Figure 2 The sample of antibacterial liquid detergent in Comparative Example 8 is after ultrasonic treatment.
[0028] Figure 3 The image shows the infrared spectrum of antibacterial agent B. Detailed Implementation
[0029] To make the objectives, technical solutions, and advantages of the embodiments of the present invention clearer, the technical solutions of the embodiments of the present invention will be clearly and completely described below with reference to the accompanying drawings. Obviously, the described embodiments are only some embodiments of the present invention, and not all embodiments. The components of the embodiments of the present invention described and shown in the accompanying drawings can generally be arranged and designed in various different configurations.
[0030] Therefore, the following detailed description of the embodiments of the invention provided in the accompanying drawings is not intended to limit the scope of the claimed invention, but merely to illustrate selected embodiments of the invention. All other embodiments obtained by those skilled in the art based on the embodiments of the invention without inventive effort are within the scope of protection of the invention.
[0031] It should be noted that similar labels and letters in the following figures indicate similar items. Therefore, once an item is defined in one figure, it does not need to be further defined and explained in subsequent figures.
[0032] In the following examples, unless otherwise specified, all contents are weight percentages, and the contents of the listed ingredients are converted contents of active substances.
[0033] In the embodiments described, the following abbreviations will be used and will have the indicated functions.
[0034] Polyquaternary ammonium salt antibacterial agent A (antibacterial agent A): a polyquaternary ammonium salt containing the following formula II repeating structure; Formula II.
[0035] Polyquaternary ammonium salt antibacterial agent B (antibacterial agent B): a polyquaternary ammonium salt containing the following formula III repeating structure; Formula III.
[0036] AE09: Ethoxylated fatty alcohol, with an average degree of ethoxylation of 9, a nonionic surfactant.
[0037] AES: Ethoxylated fatty alcohol sulfate, fatty alcohol with 12-14 carbon atoms, average degree of ethoxylation of 2, anionic surfactant.
[0038] LAS: Sodium linear alkylbenzene sulfonate, with 10-13 carbon atoms, anionic surfactant.
[0039] TW80: Polysorbate 80, usually formed by esterification of sorbitol and oleate, is a nonionic surfactant.
[0040] TX10: Octylphenoxy polyethoxyl, cyclic structure, containing 10 ethoxy units, nonionic surfactant.
[0041] PHMB: Polyhexamethylene biguanide, a polymeric cationic surfactant and antibacterial agent with broad-spectrum antibacterial properties.
[0042] 1227: Dodecyl dimethyl benzyl ammonium chloride, with 12 carbon atoms, a cationic surfactant and antibacterial agent.
[0043] According to the raw material components of Examples 1-8 shown in Table 1, the components were mixed evenly to prepare the antibacterial liquid detergents of Examples 1-8 respectively.
[0044] Table 1 Raw material components of antibacterial liquid detergents in Examples 1-8 According to the raw material components of Comparative Examples 1-9 shown in Table 2, the components were mixed evenly to prepare antibacterial liquid detergents for Comparative Examples 1-9 respectively.
[0045] Table 2 Raw material components of antibacterial liquid detergents in Comparative Examples 1-9 Antibacterial effect test In this invention, the antibacterial and bacteriostatic performance testing was conducted in accordance with QB / T 2738-2012 "Evaluation Method for Antibacterial and Bacteriostatic Effects of Daily Chemical Products". The effective concentration was 0.2%; the effective time was 20 minutes; and the effective bacterial species were Candida albicans ATCC10231 and Staphylococcus aureus. For comparison, the test was conducted under standard hard water conditions with a hardness of 342 mg / L.
[0046] Antibacterial performance is expressed as inhibition rate. The inhibition rate of the sample is calculated using the following formula: Inhibition rate (%) = (number of viable bacteria in control sample - number of viable bacteria in test sample) / number of viable bacteria in control sample × 100%.
[0047] The antibacterial performance is rated according to the antibacterial rate: >99.9% is A+ (almost completely antibacterial), less than 99.9% but greater than 90% is A (good antibacterial ability), less than 90% but greater than 80% is B (some antibacterial ability), and less than 80% is C (poor antibacterial ability).
[0048] Table 3 shows the results of the antibacterial liquid detergents of Examples 1-8 and Comparative Examples 1-9, which showed the antibacterial rate and antibacterial performance rating of Candida albicans.
[0049] Table 3. Results of Candida albicans inhibition rate and antibacterial performance rating in Examples 1-8 and Comparative Examples 1-9 As can be seen from the results in Table 3, when using a system containing 10%-12% sulfonic acid anionic surfactants, the quaternary ammonium salt bactericides and the comparative examples 1-8 (unmodified polyquaternary ammonium salt bactericides) exhibited low antibacterial rates, losing most of their antibacterial ability. However, when using the polyquaternary ammonium salt antibacterial agents (antibacterial agent A or antibacterial agent B) of this invention, a high antibacterial rate was still maintained in the anionic surfactant system, with the antibacterial rate against Candida albicans remaining above 90%, and the antibacterial rate in Example 1 even reaching >99.9%.
[0050] Antibacterial liquid detergent samples from Examples 1-8 and Comparative Examples 1-9 were placed in test tubes and sonicated at 40 kHz for 10 min. The properties of the samples after sonication were observed. The results showed that: The antibacterial liquid detergent samples from Examples 1-8 were all clear after ultrasonic treatment, indicating that the polyquaternary ammonium salt antibacterial agent of the present invention is compatible with systems containing high levels of sulfonic acid anionic surfactants; samples from Comparative Examples 4, 5, and 8 all showed insoluble flocculent precipitates. The sample from Example 8 after ultrasonic treatment is as follows... Figure 1 As shown; the sample of Comparative Example 8 after ultrasonic treatment is shown. Figure 2 As shown.
[0051] The results of the Staphylococcus aureus inhibition rate and antibacterial performance rating of the antibacterial liquid detergents in Examples 1-6 are shown in Table 4.
[0052] Table 4. Results of antibacterial rate and antibacterial performance rating of Candida albicans in Examples 1-6 As can be seen from the results in Table 4, the antibacterial liquid detergent of the present invention has excellent antibacterial effect against Staphylococcus aureus.
[0053] Infrared absorption spectroscopy characterization Attenuated total reflection Fourier transform infrared spectroscopy (ATR-FTIR) was used for testing. This method eliminates the need for complex pretreatment such as sample compression or dissolution, making it particularly suitable for direct, rapid, and non-destructive analysis of various daily chemical products, including solids, pastes, and liquids.
[0054] Place the antibacterial agent B sample on the surface of the ATR crystal, ensuring good contact between the sample and the crystal without air bubbles; use a Fourier transform infrared spectrometer (Perkin Elmer spectrum 100) at 4000-650 cm⁻¹. -1 64 scans within the range (2cm resolution) -1 After background subtraction, the infrared spectrum is obtained as follows: Figure 3 As shown.
[0055] Characteristic absorption peaks show: 2931cm -1 2858cm -1 (-CH2- stretching vibration); 1651cm -1 (C=O stretching vibration of amides); 1711cm -1 (Carboxylic acid group C=O stretching vibration); The above infrared absorption peaks prove that the carboxylic acid group was successfully introduced into the polyquaternary ammonium salt backbone.
[0056] Zeta potential test Zeta potential testing is an experimental method used to measure the electrophoretic mobility of particles moving in a liquid, thereby calculating the surface charge properties of the particles. It is primarily used to evaluate the stability of colloidal dispersions, the surface charge characteristics of particles, and to predict particle behavior in an electric field.
[0057] The zeta potential test results of antibacterial agents A, B, and PHMB are shown in Table 5.
[0058] Table 5. Zeta potential test results of antibacterial agents A, B, and PHMB As can be seen from the test results in Table 5 above, the Zeta potential values of antibacterial agents A and B (around 23 mV) are significantly higher than those of PHMB (16.9 mV), indicating stronger electrostatic repulsion, less likelihood of particle aggregation or sedimentation, and better dispersion uniformity. The peak area ratio of antibacterial agents A and B is 100%, indicating that all particles have highly consistent surface charge characteristics. The high and uniform Zeta potential helps to improve the dispersion stability of the active ingredient (antibacterial agent) in antibacterial liquid detergent, avoid local concentration fluctuations, enhance the binding efficiency with negatively charged bacterial cell membranes (positive charge is conducive to adsorption), and reduce the risk of stratification or inactivation during storage or use.
[0059] The above description is merely a specific embodiment of the present invention, but the scope of protection of the present invention is not limited thereto. Any person skilled in the art can easily conceive of various equivalent modifications or substitutions within the technical scope disclosed in the present invention, and these modifications or substitutions should all be covered within the scope of protection of the present invention. Therefore, the scope of protection of the present invention should be determined by the scope of the claims.
Claims
1. A polyquaternary ammonium salt antibacterial agent, characterized in that, It is a polyquaternary ammonium salt having repeating units of the following formula I; Equation I; where R is or X is CH3SO4, CH3CH2SO4 or a halogen.
2. The polyquaternary ammonium salt antibacterial agent according to claim 1, characterized in that, The molecular weight of the repeating unit is greater than 70% of the molecular weight of the polyquaternary ammonium salt.
3. The polyquaternary ammonium salt antibacterial agent according to claim 1, characterized in that, The weight-average molecular weight of the polyquaternary ammonium salt is 2,000-400,000.
4. The method for preparing the polyquaternary ammonium salt antibacterial agent according to any one of claims 1-3, characterized in that, Includes the following steps: Polyhexamethylene biguanide salt was dissolved in N,N-dimethylformamide, and triethylamine was added to adjust the solution to alkalinity. Then, 1-1.5 times the equivalent of the amino group in the polyhexamethylene biguanide salt was added, and the mixture was heated to 35-40°C and stirred for 14-18 hours. Acid was then added to quench the reaction and neutralize the reaction solution. Finally, acetonitrile was added to the reaction solution to precipitate the product, and the precipitate was collected to obtain the polyquaternary ammonium salt antibacterial agent. The anion in the polyhexamethylene biguanide salt is one of a halide anion, a methanesulfonic acid anion, an ethylsulfonic acid anion, or a sulfate anion; the acid anhydride is selected from succinic anhydride or phthalic anhydride.
5. The preparation method according to claim 4, characterized in that, The acid solution is selected from one of hydrochloric acid, sulfuric acid, methanesulfonic acid, and ethylsulfonic acid solutions.
6. An antibacterial liquid detergent, characterized in that, Includes the polyquaternary ammonium salt antibacterial agent as described in any one of claims 1-3.
7. The antibacterial liquid detergent according to claim 6, characterized in that, By weight percentage, it comprises the following components: 1-5% of the polyquaternary ammonium salt antibacterial agent, 15-17% of the surfactant, 0.2-10% of the detergent additive, and the balance being water.
8. The antibacterial liquid detergent according to claim 7, characterized in that, The surfactant is selected from at least one of nonionic surfactants, anionic surfactants, and amphoteric surfactants.
9. The antibacterial liquid detergent according to claim 8, characterized in that, The anionic surfactant is selected from linear alkylbenzene sulfonates, fatty alcohol polyoxyethylene ether sulfates, fatty alcohol polyoxyethylene ether carboxylates, α-alkenyl sulfonates, and fatty acid methyl ester sulfonates.
10. The antibacterial liquid detergent according to claim 7, characterized in that, The detergent additives include one or more of the following: fillers, excipients, anti-redeposition agents, chelating agents, enzyme preparations, pH adjusters, viscosity adjusters, preservatives, pigments, optical brighteners, and fragrances.
Citation Information
Patent Citations
Antibacterial fabric detergent and preparation method thereof
CN105754753A
Antibacterial composition
CN113854295A