Disinfectant and preparation method thereof

Abstract

The invention relates to an antibacterial and antiviral formula and a preparation method thereof. The formulations can be used as disinfectants and nebulized disinfectants for various hard surfaces. The disinfectant formula specifically contains DDAC and copper, and has antibacterial and antiviral activity. After the disinfectant is diluted by 130 times and 225 times with water, 100% of Escherichia coli (ATCC 8739) and 98% of Escherichia coli (ATCC 8739) can be killed within 10 min respectively. When the dilution ratio of the disinfectant reaches 10 times or above, erythema, edema, inflammation and skin allergy cannot be caused.

Description

Technical Field

[0001] The present invention relates to a disinfectant and a preparation method thereof, in particular to a unique disinfectant comprising didecyldimethylammonium chloride and a preparation method thereof, wherein the ionic liquid of the disinfectant contains a metal ion structure, the disinfectant has antibacterial and antiviral properties, and can be used for air and surface disinfection. Background Art

[0002] Misuse of antibiotics is the leading cause of new resistance mechanisms in drug-resistant pathogens. Multidrug-resistant bacteria are common in healthcare-associated infections and cause high mortality rates. According to a study, about 20% of the reported pathogens show multidrug resistance patterns. For example, methicillin-resistant Staphylococcus aureus, vancomycin-resistant enterococci (VRE), and multidrug-resistant Pseudomonas aeruginosa.

[0003] In general, pathogens are transmitted through direct or indirect contact. Microorganisms observed to be transmitted through contact are multidrug-resistant bacteria such as MRSA, ESBL-producing Gram-negative bacteria, Clostridium difficile, and rotavirus. Clostridium difficile is the most commonly reported pathogen in U.S. hospitals.

[0004] Droplet transmission is possible / occurs when microorganisms are transmitted through the respiratory tract via large droplets (larger than 5 μm) and the transmission distance is less than 3 feet. Airborne transmission is when pathogens are transmitted through the respiratory tract via smaller droplets (smaller than 5 μm) over long distances. Varicella virus, tuberculosis, measles, and the new SARS-CoV-2 virus can be transmitted through the air.

[0005] It is well known that metal ions can inactivate viruses or bacteria by interacting directly or indirectly with cells. The binding mechanism of metal ions to biomacromolecules can be explained by the site-specific Fenton mechanism. Secondary free radicals are also formed near their targets. A large number of hydroxyl radicals are generated in repeated cyclic redox reactions, and these generated free radicals cause multiple hits and damage to the target. When the protein structure is changed so that it cannot perform its normal function, it may also cause cell death or viral dysfunction.

[0006] Copper was chosen as the preferred metal ion because it is more receptive and can donate electrons. Due to this property, Cu(II) has received much attention in disinfection applications. According to literature reports, Cu(II) can effectively transfer iron from iron-sulfur clusters and play an important role in protein binding sites. It is known to target Escherichia coli respiratory enzymes in the cell membrane. Therefore, copper binding to sulfhydryl groups on proteins changes the structure and function of the enzyme. The chelation of metal ions changes the molecular structure and further hinders the decarboxylation of carboxylic acids. Compared with traditional antibiotics, the possibility of bacterial resistance to metal ions is quite low because metals can act on a variety of microbial targets, and multiple mutations are required to resist the antimicrobial activity of metal ions. At present, copper has been used for surface disinfection in the form of copper alloys, which can eliminate 99.9% of pathogenic bacteria within 2 hours of exposure to copper alloys at room temperature, including methicillin-resistant Staphylococcus aureus, Pseudomonas aeruginosa, Campylobacter jejuni, Listeria monocytogenes, Legionella pneumophila, Escherichia coli, Mycobacterium tuberculosis, and Salmonella enterica. It has been observed that these bacteria are the most dangerous pathogens, capable of causing severe and recurrent lethal infections.

[0007] In early 2021, the U.S. Environmental Protection Agency (EPA) reported that sufficient amounts of copper alloys can provide long-term effectiveness against viruses, including SARS-CoV-2.

[0008] However, copper-based aqueous solutions have poor stability, making it difficult to scale up the production of copper-based preparations at an industrial level.

[0009] Therefore, in order to overcome the above shortcomings, in combination with other antibacterial agents, the present invention discloses a novel disinfectant containing copper ions and a formula thereof, wherein the disinfectant has higher stability and stronger antimicrobial ability. Summary of the invention

[0010] The invention discloses a disinfectant, comprising:

[0011] i. Sodium chloride (0.01%-0.05%);

[0012] ii. Ethanol (0.50%-2.0%);

[0013] iii. Sodium dodecyl sulfate (0.13%-0.17%);

[0014] iv. Hydroxybenzaldehyde (0.10%-0.14%);

[0015] v. Ionic liquids (1.15%-1.25%);

[0016] vi. Copper salt (0.20%-0.60%);

[0017] vii. didecyldimethylammonium chloride (4.80%-5.02%); and

[0018] viii. Water (91.0%-94.0%)

[0019] The preparation method of the disinfectant is as follows:

[0020] Solution A: Aqueous solution of quaternary ammonium compounds (2-12%).

[0021] Solution B: copper salt solution (dissolved in solvent).

[0022] Solution C: sodium hydroxide + different amounts (5-75 g) of p-hydroxybenzaldehyde / m-hydroxybenzaldehyde / salicylaldehyde / or their combination.

[0023] Prepare solution D by taking 4.89% solution A, 10-30 mL solution C and 1.5 g surfactant aqueous solution. Add 5-20 mL solution B to solution D to obtain a uniform solution. Add 5-23 g ionic liquid / or its composition. Dilute the contents with water to a total solution volume of 1 L.

[0024] Description of the Figures and Tables

[0025] The above and other features and advantages of the present invention will be more fully understood by reading the following description and by referring to the following drawings.

[0026] Figure 1 The time-kill test results for HP08-04 (disinfectant formula diluted 100 times), HP08-08 (disinfectant formula diluted 130 times), and HP08-09 (disinfectant formula diluted 225 times) are listed. HP08-04 is 100% effective within 30 seconds, HP08-08 is 100% effective within 10 minutes, and HP08-09 is 98% effective within 10 minutes.

[0027] Figure 2 The residual effectiveness of HP08-01, HP08-02, HP08-03, HP08-05, HP08-06, HP08-07, and HP08-04 is shown.

[0028] Table 1 shows the skin irritation test standards.

[0029] Table 2 shows the rabbit skin irritation test of HP08 10× and 20× at different time intervals.

[0030] The above and other features and advantages of the present invention may be incorporated into some embodiments of the present invention, and in combination with the following description or with the practice of the present invention described below, the above and other features and advantages of the present invention will be clearer and easier to understand. The present invention does not require that all the advantageous features and all the advantages described herein be incorporated into every embodiment of the present invention. DETAILED DESCRIPTION

[0031] The following content is a simplified description of the present invention, which is only intended to provide a basic understanding of certain aspects of the present invention and should not be regarded as a comprehensive overview of the present invention. The following description is not intended to identify the key / important elements of the present invention or to define the scope of the present invention. Its sole purpose is to introduce certain concepts of the present invention in a simplified form. Therefore, those of ordinary skill in the art will recognize that various changes and modifications can be made to the embodiments described herein without departing from the scope of the present invention. In addition, for the sake of brevity and clarity, well-known functions and structures are not repeated in this specification.

[0032] Features described and / or shown for one embodiment may be used in one or more other embodiments in the same or similar manner and / or used together with or in place of features of other embodiments. The terms and words used in the following description and claims are not limited to their bibliographic meanings, but are used only by the inventor for the purpose of a clear and consistent understanding of the present invention. Therefore, it should be understood by those skilled in the art that the following description of exemplary embodiments of the present invention is for illustrative purposes only and should not be regarded as limiting the present invention, and the scope of the present invention is defined by the claims and their equivalents.

[0033] The terms "a", "an" and "the" used in this specification to express a singular concept include plural references unless the context clearly dictates otherwise.

[0034] The term "substantially" as used in this specification means that the characteristics, parameters or values ​​described need not be achieved precisely, but deviations or changes are allowed, including, for example, tolerances, measurement errors, measurement precision limitations and other factors known to those skilled in the art, but their amounts will not hinder the effect of the expected achievement of the characteristics.

[0035] The term “comprising” used in this specification is used to indicate the existence of stated features, integers, steps or components, but does not exclude the existence or addition of one or more other features, integers, steps, components or groups thereof.

[0036] The term "HP08" as used in this specification refers to the disinfectant formulation.

[0037] The term "MBPC" as used in this specification refers to Minimum Biofilm Prevention Concentration.

[0038] The term "MBIC" as used in this specification refers to minimum biofilm inhibition concentration.

[0039] The following is a detailed description of an embodiment of the present invention. The same or similar elements / components and elements / components with the same or similar functions are denoted by reference numerals herein.

[0040] The embodiments described herein with reference to the accompanying drawings are merely exemplary illustrations, which are useful for general understanding of the contents of the present invention and should not be regarded as limiting the present invention.

[0041] The present invention provides a disinfectant having antibacterial and antiviral properties.

[0042] According to an embodiment of the present invention, an antibacterial and antiviral formulation for surface disinfection is provided.

[0043] The disinfectant comprises:

[0044] ix. Sodium chloride (0.01%-0.05%);

[0045] x. Ethanol (0.50%-2.0%);

[0046] xi. Sodium dodecyl sulfate (0.13%-0.17%);

[0047] xii. Hydroxybenzaldehyde (0.10%-0.14%);

[0048] xiii. Ionic liquids (1.15%-1.25%);

[0049] xiv. Copper salt (0.20%-0.60%);

[0050] xv. didecyldimethylammonium chloride (4.80% -5.02%); and

[0051] xvi. Water (91.0%-94.0%).

[0052] According to an embodiment of the present invention, the disinfectant formulation comprises a quaternary ammonium compound and a copper salt as its active ingredients. According to an embodiment of the present invention, the copper salt is selected from cupric chloride, cupric sulfate, cupric nitrate, cupric acetate, cupric perchlorate, cupric iodide and / or a combination thereof, but is not limited to the compounds.

[0053] In a preferred embodiment, the copper salt is copper sulfate.

[0054] According to an embodiment of the present invention, the ionic liquid is selected from the halide of 1-(carboxymethyl)pyridin-1-ium; the halide of 1,3-bis(carboxymethyl)-1H-benzo[d]imidazol-3-ium; the halide of 3-(carboxymethyl)-1-methyl-1H-imidazol-3-ium; the halide of 1,3-bis(carboxymethyl)-1H-imidazol-3-ium and / or a combination thereof.

[0055] According to an embodiment of the present invention, the hydroxybenzaldehyde is selected from p-hydroxybenzaldehyde, m-hydroxybenzaldehyde and salicylaldehyde or a combination thereof.

[0056] According to an embodiment of the present invention, the quaternary ammonium compound is DDAC.

[0057] According to an embodiment, the disinfectant solution of the present invention comprises the quaternary ammonium compound DDAC as an active entity.

[0058] In a preferred embodiment, the disinfectant comprises:

[0059] i. Sodium chloride (0.02%);

[0060] ii. Ethanol (1.03%);

[0061] iii. Sodium dodecyl sulfate (0.162%);

[0062] iv. Hydroxybenzaldehyde (0.113%);

[0063] v. Ionic liquid (1.21%);

[0064] vi. Copper salt (0.42%);

[0065] vii. didecyldimethylammonium chloride (4.89%); and

[0066] viii. Water (93.15%)

[0067] In a preferred embodiment, the disinfectant comprises:

[0068] ix. Sodium chloride (0.02%);

[0069] x. Ethanol (1.03%);

[0070] xi. Sodium dodecyl sulfate (0.162%);

[0071] xii. Hydroxybenzaldehyde (0.113%);

[0072] xiii. 1-(Carboxymethyl)pyridin-1-ium; 1,3-bis(carboxymethyl)-1H-benzo[d]imidazol-3-ium (1.21%);

[0073] xiv. Copper salt (0.42%);

[0074] xv. Didecyldimethylammonium chloride (4.89%); and

[0075] xvi. Water (93.15%)

[0076] In one embodiment, the method for preparing the disinfectant comprises:

[0077] Solution A: Aqueous solution of quaternary ammonium compounds (2-12%).

[0078] Solution B: copper salt solution (dissolved in solvent).

[0079] Solution C: sodium hydroxide + different amounts (5-75 g) of p-hydroxybenzaldehyde / m-hydroxybenzaldehyde / salicylaldehyde / or their combination.

[0080] In one embodiment, 4.89% solution A, 10-30 mL solution C and 1.5 g of any one surfactant aqueous solution are taken to prepare solution D. 5-20 mL solution B is added to solution D to obtain a uniform solution. 5-23 g of ionic liquid / or its composition is added. The contents are diluted with water to a total solution volume of 1 L.

[0081] In a preferred embodiment, the method for preparing the disinfectant comprises:

[0082] Solution A: Aqueous solution of quaternary ammonium compound (4%).

[0083] Solution B: 0.42% copper salt solution (dissolved in solvent).

[0084] Solution C: sodium hydroxide-p-hydroxybenzaldehyde (25 g) solution.

[0085] In one embodiment, 40% solution A, 20 mL solution C and 1.5 g of any one surfactant aqueous solution are taken to prepare solution D. 10 mL solution B is added to solution D to obtain a uniform solution. 15 g of ionic liquid / or its composition is added. The contents are diluted with water to a total solution volume of 1 L.

[0086] In one embodiment, the disinfectant is prepared in the presence of an ionic liquid.

[0087] According to an embodiment of the present invention, the ionic liquid may be selected from 1-(carboxymethyl)pyridin-1-ium halides; 1,3-bis(carboxymethyl)-1H-benzo[d]imidazol-3-ium halides; 3-(carboxymethyl)-1-methyl-1H-imidazol-3-ium halides; 1,3-bis(carboxymethyl)-1H-imidazol-3-ium halides and / or combinations thereof.

[0088] The prepared disinfectant was fully characterized and confirmed by UV-Vis and Fourier transform infrared spectroscopy (FT-IR) techniques.

[0089] The disinfectant formulation or disinfectant solution of the present invention is mainly used to develop a material that can prevent the spread of microbial infection. The sterilization efficacy of the present invention is determined by the following examples:

[0090] Example 1: Efficacy Test: Time-kill Test

[0091] Time-kill kinetics tests are used to evaluate the bactericidal or bacteriostatic activity of antimicrobial agents over time. Bactericidal activity is defined as a >3 log10 10-fold reduction in colony forming units (viable bacteria), which is equivalent to a 99.9% kill of the inoculum.

[0092] The antimicrobial effectiveness of three dilutions of disinfectants with batch numbers HP08-04 (100×), HP08-08 (130×) and HP08-09 (225×) against Escherichia coli strains (ATCC 8739) was determined by time-killing test at different time intervals (30s, 1min, 2min, 5min and 10min). In this test, the disinfectant formula (HP08) was diluted 100 times, 130 times and 225 times respectively. 5 cfu / mL of the target microorganism. To do this, a cell suspension was prepared by dissolving an 18-24 h culture of E. coli in 9 mL of 0.9% saline. Serial dilutions were prepared to obtain known cell counts and 0.1 mL containing no more than 10 7 Add a dilution of 10 cells to a test tube containing 1 mL of the product. After adding the culture to the product, maintain contact time intervals of 30s, 1min, 2min, 5min and 10min. After each time interval, transfer all 1mL of the product to 9mL Dey Engley neutralizing broth. Prepare serial dilutions and culture on plates using SCDA medium. Incubate the plates at 32.5°C for 18-24h. After incubation, observe the recovery rate of the test bacteria in the plates. Store the positive control together with the sample. Compare the recovery rate of the test bacteria at different time intervals with the positive control, and calculate the log10 reduction value.

[0093] The disinfectant with batch number HP08-04 (100×) can completely kill pathogens or reduce the value by more than 6 log10 (>99.9999%) within a time interval of 30 seconds.

[0094] The disinfectant batch number HP08-08 (130×) observed a reduction of 3 log10 (>99.9%) at a 10 min time interval, followed by a reduction of 3 log10 (99.9%) at a 5 min time interval, and a reduction of 2 log10 (90%) at a 1 min time interval.

[0095] For the disinfectant batch HP08-09 (225×), the maximum log10 reduction was observed, ie a reduction of >3 log10 (<99%) at a 10 min time interval.

[0096] Example 2: Residual Effectiveness

[0097] According to the quality standards provided by USP-1072 Disinfectants and Antimicrobial Agents and ISO 14698 (1-3), the residual effectiveness test scheme of HP08 was adopted. The effectiveness of HP08 in inhibiting the growth of Escherichia coli, Staphylococcus aureus and Candida albicans was examined at different dilutions. The results showed that after HP08 was diluted 75 times, there was no sterile growth for up to 10 days. The microbial growth limit of the test was not less than 95.0%.

[0098] Evaluation of anti-biofilm activity

[0099] The antibiofilm activity of the test articles against S. aureus ATCC 29213 biofilms was determined in 96-well flat-bottom microtiter plates by XTT dye reduction assay. In the prevention study, 200 μL of microbial suspension (5.a11re11s″″107 cfu / mL) was incubated in nutrient medium [S. aureus, Mueller Hinton broth (MHB)] containing 2-fold serial dilutions of the test articles [HP08-02, 1:2 to 1:4096 dilutions] at 37°C for 24 h to allow biofilm formation.

[0100] The untreated control was set as a parallel sample. After incubation, the formed biofilm was washed twice with saline and exposed to XTT-menadione solution (XTT, 0.5 mg / mL; menadione, 10 μM) for 1 h at 37°C in the dark. The absorbance of the supernatant was measured at 450 nm. Similarly, to determine the effectiveness of the test article in eliminating the original biofilm, 24h biofilms of Staphylococcus aureus ATCC 29213 were treated with 2-fold serial dilutions of the test article at 37°C and quantified by XTT dye reduction test. MBPC 50 、MBPC 90 and MBPC 100 Defined as the test article concentration that results in a 50%, 90%, and 100% reduction in biofilm formation, respectively, compared to the untreated control. 50、MBPC 90 and MBPC 100 Defined as the test article concentration that results in a 50%, 90% and 100% reduction in pre-formed biofilm biomass, respectively, compared to the untreated control.

[0101] MBPC was observed at dilutions of 1:512, 1:256, and 1:256 50 、MBPC 90 and MBPC 100 .

[0102] Skin irritation of HP08 (concentration 10X, 20X)

[0103] In order to observe the skin compatibility of the product of the present invention, a skin irritation test was performed according to the OECD guidelines. For this reason, an acute single skin irritation test was performed, with rabbits in the control group receiving a placebo patch and rabbits in the treatment group receiving a transdermal patch containing HP08. To carry out the experiment, the hair of the rabbit trunk of about 5cm×5cm in size was shaved. Afterwards, the product of the present invention was attached to a complete part of each rabbit, covered with 2.5cm×2.5cm gauze, and wrapped with a closed dressing. The test product was attached to the skin for 4h, and then all patches and dressings were removed. Afterwards, the test site was cleaned with warm water to remove the remaining test product on the skin. No skin reaction was observed within 4h after removing the patch.

[0104] Subsequently, according to the guidelines, erythema and edema were scored on a 0-4 scale, where 0 means no effect and 4 means severe symptoms. After removing the patch, the skin reactions of each animal were scored at 1h, 24h, 48h and 72h. The obtained score was divided by 3 to obtain the average irritation score at each time point. The results of the two groups (placebo group and test group) were compared. Table 1 shows the average score, and the primary irritation index was obtained by averaging.

[0105] Table 1 - Skin irritation test standards

[0106]

[0107]

[0108] Table 2—Rabbit skin irritation test of HP08 10× and 20× at different time intervals

[0109]

[0110] Skin irritation classification

[0111] · Non-irritating - the average value of the skin irritation caused by the compound (primary irritation index) is 0; · Mildly irritating - the average value of the skin irritation caused by the compound is less than 2;

[0112] Moderate irritation - the average value of the skin irritation caused by the compound is between 2 and 5;

[0113] Severe or primary irritant - the compound causes a composite mean skin irritation greater than 5 or causes extensive eschar formation.

[0114] No erythema, edema, inflammation or skin allergy was observed. Therefore, the compound was classified as a non-irritating compound.

[0115] Although various specific implementation schemes are used to describe the embodiments herein, it is obvious to those skilled in the art that certain modifications may be made when practicing the invention, and the modifications made by those skilled in the art are deemed to be within the scope of protection of the invention.

[0116] Industrial Applicability

[0117] The invention relates to a unique disinfectant comprising didecyldimethylammonium chloride and a preparation method thereof. The ionic liquid of the disinfectant contains a metal ion structure.

[0118] The present invention provides a disinfectant having antibacterial and antiviral properties.

[0119] The formulation process can be scaled up to industrial scale.

[0120] The disinfectant is more stable and has a better killing effect on any surface microorganisms.

[0121] The disinfectant can kill 100% of Escherichia coli strains (ATCC 8739) within 30 seconds and 10 minutes respectively after being diluted 100 times and 130 times (with water).

[0122] After the disinfectant is diluted 75 times, there is no Escherichia coli, Staphylococcus aureus or / and

[0123] and Candida albicans growth.

[0124] After 10-fold dilution, no erythema, edema, inflammation or skin allergy was observed.

[0125] References

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Claims

1. A disinfectant comprising: i. Sodium chloride (0.01%-0.05%); ii. Ethanol (0.50%-2.0%); iii. Sodium dodecyl sulfate (0.13%-0.17%); iv. Hydroxybenzaldehyde (0.10%-0.14%); v. Ionic liquids (1.15%-1.25%); vi. Copper salt (0.20%-0.60%); vii. didecyldimethylammonium chloride (4.80%-5.02%); viii. Water (91.0%-94.0%).

2. The disinfectant according to claim 1, wherein the copper salt is selected from copper chloride, copper sulfate, copper nitrate, copper acetate, copper perchlorate, copper iodide and / or a combination thereof, but is not limited to the compounds.

3. The disinfectant according to claim 1, wherein the ionic liquid is selected from the group consisting of 1-(carboxymethyl)pyridin-1-ium halides; 1,3-bis(carboxymethyl)-1H-benzo[d]imidazol-3-ium halides; 3-(carboxymethyl)-1-methyl-1H-imidazol-3-ium halides; 1,3-bis(carboxymethyl)-1H-imidazol-3-ium halides and / or combinations thereof.

4. The disinfectant according to claim 1, wherein the hydroxybenzaldehyde is selected from p-hydroxybenzaldehyde, m-hydroxybenzaldehyde and salicylaldehyde or a combination thereof.

5. The disinfectant according to claim 1, wherein the preparation method comprises: i. Mix 30-60% solution A, 10-30mL solution C and 1.5g aqueous surfactant solution to prepare solution D; ii. Add 5-20 mL of solution B to solution D to obtain a uniform solution; iii. adding 5-23g of ionic liquid; iv. dilute the contents with water to 100% total solution volume; in: Solution A: aqueous solution of quaternary ammonium compound; Solution B: copper salt-ethanol aqueous solution; Solution C: sodium hydroxide-hydroxybenzaldehyde solution.

6. The disinfectant according to claim 1, after being diluted 100 times and 130 times (with water), the disinfectant can kill 100% of Escherichia coli strains (ATCC8739) within 30 seconds and 10 minutes respectively.

7. The disinfectant according to claim 1, after being diluted 75 times, the solution has no growth of Escherichia coli, Staphylococcus aureus or / and Candida albicans for up to 10 days.

8. The disinfectant according to claim 1, in the anti-biofilm activity test, MBPC was observed at dilutions of 1:512, 1:256, and 1:256, respectively. 50 、MBPC 90 and MBPC 100 .

9. The disinfectant according to claim 1, after being diluted 10 times, the disinfectant does not cause erythema, edema, inflammation and skin allergy.

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