Virus and microbial control agents, resin additives, and methods for controlling viruses and microorganisms

Abstract

To provide a virus / microbe control agent that features superior stability at low temperatures, a resin additive, and a virus / microbe control method.SOLUTION: A virus / microbe control agent comprises N,N'-alkylene-bis(4-carbamoyl-1-alkylpyridinium salt), and C2-4 alkylene glycol monophenyl ether. N,N'-alkylene-bis(4-carbamoyl-1-alkylpyridinium salt) is less than 40 mass%. According to the present invention, a resin additive comprises the virus / microbe control agent. According to the present invention, a virus / microbe control method uses the virus / microbe control agent.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a virus and microbial control agent, a resin additive, and a method for controlling viruses and microorganisms, more specifically, to a virus and microbial control agent used as a control agent for viruses, bacteria, molds, yeasts, and algae, a resin additive containing the virus and microbial control agent, and a method for controlling viruses and microorganisms using the virus and microbial control agent. [Background technology]

[0002] Traditionally, various industrial products have been susceptible to the proliferation of harmful microorganisms such as bacteria, mold, yeast, and algae, leading to decreased productivity and quality, as well as the generation of unpleasant odors. Therefore, it is widely known that various microbial control agents exhibiting antibacterial, antifungal, antiseptic, and anti-algal effects are added to industrial products to prevent the growth of such harmful microorganisms.

[0003] As such a microbial control agent, for example, bisquaternary ammonium salt compounds have been reported to have a broad antimicrobial spectrum and exhibit excellent control effects (see, for example, Patent Document 1). [Prior art documents] [Patent Documents]

[0004] [Patent Document 1] Japanese Patent Publication No. 2004-196670 [Overview of the project] [Problems that the invention aims to solve]

[0005] However, the microbial control agent described in Patent Document 1 may have insufficient low-temperature stability.

[0006] The present invention relates to a virus and microbial control agent that can improve low-temperature stability, a resin additive containing the virus and microbial control agent, and a method for controlling viruses and microorganisms using the virus and microbial control agent. [Means for solving the problem]

[0007] The present invention [1] relates to N,N'-alkylene-bis(4-carbamoyl-1-alkylpyridinium salt) and C 2-4 The present invention contains a virus and microbial control agent that contains alkylene glycol monophenyl ether, wherein the N,N'-alkylene-bis(4-carbamoyl-1-alkylpyridinium salt) is present in an amount of less than 40% by mass.

[0008] The present invention [2] relates to the C 2-4 The virus and microbial control agent described in [1] above is provided, wherein alkylene glycol monophenyl ether is ethylene glycol monophenyl ether.

[0009] The present invention [3] contains the virus and microbial control agent described in [1] or [2] above, wherein the N,N'-alkylene-bis(4-carbamoyl-1-alkylpyridinium salt) is present in an amount of 30% by mass or less.

[0010] The present invention [4] includes a resin additive containing a virus / microbial control agent described in any of [1] to [3] above.

[0011] The present invention [5] includes a method for controlling viruses and microorganisms using a virus and microorganism control agent described in any of [1] to [3] above. [Effects of the Invention]

[0012] The virus and microbial control agent of the present invention comprises N,N'-alkylene-bis(4-carbamoyl-1-alkylpyridinium salt) and C 2-4 It contains alkylene glycol monophenyl ether, and the amount of N,N'-alkylene-bis(4-carbamoyl-1-alkylpyridinium salt) is less than 40% by mass. Therefore, such a virus and microbial control agent has excellent low-temperature stability.

[0013] In addition, the resin additive of the present invention contains the above virus / microorganism control agent. Therefore, such a resin additive has excellent low-temperature stability.

[0014] The method for controlling viruses / microorganisms of the present invention uses the above virus / microorganism control agent. Therefore, according to such a method for controlling viruses / microorganisms, since the above virus / microorganism control agent has excellent low-temperature stability, the virus / microorganism control agent can be stably stored at low temperature until use, and viruses / microorganisms can be controlled.

Mode for Carrying Out the Invention

[0015] The virus / microorganism control agent of the present invention contains N,N'-alkylene-bis(4-carbamoyl-1-alkylpyridinium salt) as an active ingredient.

[0016] Examples of the alkylene group of N,N'-alkylene-bis(4-carbamoyl-1-alkylpyridinium salt) include alkylene groups having 1 to 18 carbon atoms.

[0017] Examples of the alkylene group having 1 to 18 carbon atoms include methylene, ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene, isodecylene, dodecylene, tetradecylene, hexadecylene, and octadecylene.

[0018] The alkylene group of N,N'-alkylene-bis(4-carbamoyl-1-alkylpyridinium salt) preferably includes an alkylene group having 4 to 12 carbon atoms, more preferably an alkylene group having 6 to 8 carbon atoms, and even more preferably hexylene. Hexylene is preferably hexamethylene.

[0019] Examples of the alkyl group of N,N'-alkylene-bis(4-carbamoyl-1-alkylpyridinium salt) include alkyl groups having 1 to 18 carbon atoms.

[0020] Examples of the alkyl group having 1 to 18 carbon atoms include methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, n-pentyl, iso-pentyl, n-hexyl, iso-hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, and octadecyl.

[0021] As the alkyl group having 1 to 18 carbon atoms, preferably, an alkyl group having 8 to 12 carbon atoms, more preferably, decyl is exemplified.

[0022] Examples of the pyridinium salt of N,N'-alkylene-bis(4-carbamoyl-1-alkylpyridinium salt) include bromide (pyridinium bromide), iodide (pyridinium iodide), and acetate (pyridinium acetate).

[0023] As the pyridinium salt of N,N'-alkylene-bis(4-carbamoyl-1-alkylpyridinium salt), preferably, bromide (pyridinium bromide), and acetate (pyridinium acetate), more preferably, bromide (pyridinium bromide) is exemplified.

[0024] Specific examples of N,N'-alkylene-bis(4-carbamoyl-1-alkylpyridinium salt) include, for example, N,N'-hexamethylenebis(4-carbamoyl-1-decylpyridinium salt).

[0025] Examples of N,N'-hexamethylenebis(4-carbamoyl-1-decylpyridinium salt) include N,N'-hexamethylenebis(4-carbamoyl-1-decylpyridinium bromide), N,N'-hexamethylenebis(4-carbamoyl-1-decylpyridinium iodide), and N,N'-hexamethylenebis(4-carbamoyl-1-decylpyridinium acetate).

[0026] As N,N'-hexamethylenebis(4-carbamoyl-1-decylpyridinium salt), N,N'-hexamethylenebis(4-carbamoyl-1-decylpyridinium bromide) is a preferred example.

[0027] These N,N'-alkylene-bis(4-carbamoyl-1-alkylpyridinium salts) may be used alone or in combination of two or more.

[0028] Furthermore, commercially available N,N'-alkylene-bis(4-carbamoyl-1-alkylpyridinium salts) used in the present invention can also be used, for example, N,N'-hexamethylenebis(4-carbamoyl-1-decylpyridinium bromide) (Dimer 38, manufactured by Inui Co., Ltd.) and N,N'-hexamethylenebis(4-carbamoyl-1-decylpyridinium acetate) (Dimer 38A, manufactured by Inui Co., Ltd.).

[0029] The content of N,N'-alkylene-bis(4-carbamoyl-1-alkylpyridinium salt) is, for example, 0.1% by mass or more, preferably 1% by mass or more, more preferably 4% by mass or more, even more preferably 5% by mass or more, particularly preferably 10% by mass or more, most preferably 15% by mass or more, and less than 40% by mass, preferably 30% by mass or less, more preferably 25% by mass or less, and even more preferably 20% by mass or less. If it is above the above upper limit, N,N'-alkylene-bis(4-carbamoyl-1-alkylpyridinium salt) is C 2-4 It cannot be completely dissolved in alkylene glycol monophenyl ether. Furthermore, the virus and microbial control agent of the present invention contains N,N'-alkylene-bis(4-carbamoyl-1-alkylpyridinium salt), even at high concentrations (e.g., 5% by mass or more), C 2-4 It is soluble in alkylene glycol monophenyl ether and exhibits excellent low-temperature stability thereafter. As a result, it can be stored stably until use and can be diluted before use.

[0030] In the virus and microorganism control agent of the present invention, in order to improve the low-temperature stability, as a solvent, C 2-4 contains alkylene glycol monophenyl ether.

[0031] C 2-4 Examples of the alkylene glycol monophenyl ether include ethylene glycol monophenyl ether (2-phenoxyethanol), propylene glycol monophenyl ether (1-phenoxy-2-propanol and 3-phenoxy-1-propanol), and butylene glycol monophenyl ether (4-phenoxy-1-butanol).

[0032] C 2-4 Preferably, the alkylene glycol monophenyl ether includes ethylene glycol monophenyl ether and propylene glycol monophenyl ether (preferably 1-phenoxy-2-propanol), and more preferably ethylene glycol monophenyl ether.

[0033] C 2-4 The alkylene glycol monophenyl ether may be used alone or in combination of two or more.

[0034] C 2-4 The content ratio of the alkylene glycol monophenyl ether is, for example, preferably more than 60% by mass, more preferably 70% by mass or more, still more preferably 75% by mass or more, particularly preferably 80% by mass or more, and also, for example, 99.9% by mass or less, more preferably 99% by mass or less, still more preferably 96% by mass or less, particularly preferably 90% by mass or less, and most preferably 85% by mass or less, based on the total amount of the virus and microorganism control agent.

[0035] C 2-4The content of alkylene glycol monophenyl ether is, for example, more than 150 parts by mass, more preferably 230 parts by mass or more, even more preferably 300 parts by mass or more, particularly preferably 400 parts by mass or more, or, for example, 99,900 parts by mass or less, preferably 9,900 parts by mass or less, more preferably 2,400 parts by mass or less, even more preferably 900 parts by mass or less, particularly preferably 560 parts by mass or less, per 100 parts by mass of N,N'-alkylene-bis(4-carbamoyl-1-alkylpyridinium salt).

[0036] Also, C 2-4 The proportion of alkylene glycol monophenyl ether in the virus and microbial control agent is the remainder of N,N'-alkylene-bis(4-carbamoyl-1-alkylpyridinium salt) and any additional additives (described below) as needed.

[0037] Depending on its purpose and application, the virus and microbial control agent of the present invention may contain known additives, such as surfactants, other algal and / or fungicides, antioxidants, and light stabilizers.

[0038] Examples of surfactants include nonionic surfactants, cationic surfactants, and anionic surfactants. Nonionic surfactants are preferred as surfactants. Examples of nonionic surfactants include ether-type nonionic surfactants. Examples of ether-type nonionic surfactants include polyoxyethylene lauryl ether, polyoxyethylene cetyl ether, polyoxyethylene stearyl ether, polyoxyethylene oleyl ether, polyoxyethylene alkyl ether, polyoxyethylene myristyl ether, polyoxyalkylene alkyl ether, polyoxyethylene distyrenated phenyl ether, polyoxyethylene tripenzylphenyl ether, and polyoxyethylene polyoxypropylene. Preferred polyoxyethylene derivatives include polyoxyalkylene alkyl ether and polyoxyethylene tripenzylphenyl ether.

[0039] These surfactants may be used individually or in combination of two or more.

[0040] These surfactants are available commercially, and more specifically, as polyoxyethylene distyrenated phenyl ethers, examples include Emulgen (manufactured by Kao Corporation, hereinafter the same) A-60, Emulgen A-90, and Emulgen A-500.

[0041] Examples of polyoxyethylene alkyl ethers include Emulgen 705, Emulgen 707, and Emulgen 709.

[0042] Examples of polyoxyalkylene alkyl ethers include Emulgen LS-110 and Emulgen LS-114.

[0043] An example of polyoxyethylene tribenzylphenyl ether is Emulgen B-66.

[0044] The surfactant content is, for example, 0.1% by mass or more, preferably 0.5% by mass or more, more preferably 1.0% by mass or more, even more preferably 1.5% by mass or more, and most preferably 1.75% by mass or more, relative to the virus and microbial control agent. Alternatively, it may be, for example, 20% by mass or less, preferably 10% by mass or less, more preferably 7.5% by mass or less, even more preferably 5% by mass or less, most preferably 4% by mass or less, and most preferably 3% by mass or less.

[0045] The surfactant content is, for example, 0.5 parts by mass or more, preferably 2.5 parts by mass or more, more preferably 5.0 parts by mass or more, even more preferably 7.5 parts by mass or more, particularly preferably 8.75 parts by mass or more, per 100 parts by mass of N,N'-alkylene-bis(4-carbamoyl-1-alkylpyridinium salt), and also, for example, 100 parts by mass or less, preferably 50 parts by mass or less, more preferably 37.5 parts by mass or less, even more preferably 25 parts by mass or less, particularly preferably 20 parts by mass or less, and most preferably 15 parts by mass or less.

[0046] The virus and microbial control agent of the present invention is N,N'-alkylene-bis(4-carbamoyl-1-alkylpyridinium salt), C 2-4 It can be obtained as a liquid by compounding alkylene glycol monophenyl ether and, if necessary, additives.

[0047] The virus and microbial control agent of the present invention exhibits excellent antiviral, antibacterial, antifungal, antiseptic, and anti-algal activity, and can be used as a control agent against viruses, bacteria, molds, yeasts, algae, etc. Moreover, the virus and microbial control agent of the present invention is C 2-4 Because it contains alkylene glycol monophenyl ether, it exhibits excellent low-temperature stability. In particular, the virus and microbial control agent of the present invention exhibits excellent low-temperature stability even when N,N'-alkylene-bis(4-carbamoyl-1-alkylpyridinium salt) is present at a high concentration (5% by mass or more).

[0048] The virus and microbial control agent of the present invention is suitably used as a resin additive added to resins in various industrial products. That is, the resin additive contains the virus and microbial control agent.

[0049] Examples of resins to which the resin additive of the present invention is added include casein, starch paste, animal glue, coated paper, paper coating liquid, surface sizing agents, adhesives, synthetic rubber latex, inks, polyvinyl alcohol films, vinyl chloride films, cement admixtures, sealants, joint fillers, resin emulsions, and paints.

[0050] The amount of the virus / microbial control agent or resin additive of the present invention can be appropriately determined depending on the target application. When used as a microbial control agent, the virus / microbial control agent or resin additive of the present invention can be used at a concentration of, for example, 1 mg (total active ingredient) / kg (product) or more, preferably 5 mg (total active ingredient) / kg (product) or more, and also at a concentration of, for example, 50,000 mg (total active ingredient) / kg (product) or less, preferably 10,000 mg (total active ingredient) / kg (product) or less. When used as a virus control agent (antiviral agent), the virus / microbial control agent or resin additive of the present invention can be used at a concentration of, for example, 1 mg (total active ingredient) / kg (product) or more, preferably 5 mg (total active ingredient) / kg (product) or more, and also at a concentration of, for example, 500,000 mg (total active ingredient) / kg (product) or less, preferably 100,000 mg (total active ingredient) / kg (product) or less. If the virus / microbial control agent or resin additive is at a high concentration (5% by mass or more), it can be used after being appropriately diluted.

[0051] The present invention provides a method for controlling viruses and microorganisms using the above-mentioned virus and microorganism control agent.

[0052] In the method for controlling viruses and microorganisms of the present invention, the amount of the above-mentioned virus and microbial control agent to be added can be appropriately determined according to the target of application. When using the above-mentioned virus and microbial control agent in the method for controlling viruses and microorganisms of the present invention, the ratio of the total active ingredient to the product ((total active ingredient) / kg(product)) can be used, for example, in the ratio described above. [Examples]

[0053] The present invention will be further described with reference to the following examples, but the present invention is not limited thereto. Specific numerical values ​​such as blending ratios (content), physical properties, and parameters used in the following description may be replaced with the corresponding upper limits (numerical values ​​defined as "less than or equal to" or "less than") or lower limits (numerical values ​​defined as "greater than or equal to" or "greater than or equal to" or "greater than or equal to") of the blending ratios (content), physical properties, and parameters described in the "Modes for Carrying Out the Invention" above. Note that "parts" and "%" refer to mass unless otherwise specified.

[0054] Example 1 4.0 g of dimer 38 (99% by weight, manufactured by Inui) and 16.0 g of ethylene glycol monophenyl ether were weighed into a 6K glass bottle. The mixture was stirred and dissolved at room temperature (25°C) to obtain 20 g of liquid.

[0055] Example 2 6.0 g of dimer 38 (99% by weight, manufactured by Inui) and 14.0 g of ethylene glycol monophenyl ether were weighed into a 6K glass bottle. The mixture was stirred and dissolved at room temperature (25°C) to obtain 20 g of the solution.

[0056] Example 3 4.0 g of dimer 38 (99% by weight, manufactured by Inui Co., Ltd.) and 16.0 g of propylene glycol-1-monophenyl ether (1-phenoxy-2-propanol) were weighed into a 6K glass bottle. The mixture was stirred and dissolved at room temperature (25°C) to obtain 20 g of the solution.

[0057] Example 4 4.0 g of Dimer 38 (99% by weight, manufactured by Inui Co.), 15.6 g of ethylene glycol monophenyl ether, and 0.4 g of Emulgen LS-110 (polyoxyalkylene alkyl ether, manufactured by Kao Corporation) were weighed into a 6K glass bottle. The mixture was stirred and dissolved at room temperature (25°C) to obtain 20 g of the solution.

[0058] Example 5 4.0 g of Dimer 38 (99% by weight, manufactured by Inui Co.), 15.6 g of ethylene glycol monophenyl ether, and 0.4 g of Emulgen LS-114 (polyoxyalkylene alkyl ether, manufactured by Kao Corporation) were weighed into a 6K glass bottle. The mixture was stirred and dissolved at room temperature (25°C) to obtain 20 g of the solution.

[0059] Example 6 4.0 g of Dimer 38 (99% by weight, manufactured by Inui Co.), 15.2 g of ethylene glycol monophenyl ether, and 0.8 g of Emulgen LS-114 (polyoxyalkylene alkyl ether, manufactured by Kao Corporation) were weighed into a 6K glass bottle. The mixture was stirred and dissolved at room temperature (25°C) to obtain 20 g of the solution.

[0060] Example 7 4.0 g of Dimer 38 (99% by weight, manufactured by Inui Co.), 15.6 g of ethylene glycol monophenyl ether, and 0.4 g of Emulgen B-66 (polyoxyethylene tripenzylphenyl ether, manufactured by Kao Corporation) were weighed into a 6K glass bottle. The mixture was stirred and dissolved at room temperature (25°C) to obtain 20 g of the solution.

[0061] Comparative Example 1 8.0 g of dimer 38 (99% by weight, manufactured by Inui) and 12.0 g of ethylene glycol monophenyl ether were weighed into a 6K glass bottle. The mixture was stirred at room temperature (25°C), but the dimer 38 did not completely dissolve.

[0062] Comparative Example 2 4.0 g of dimer 38 (99% by weight, manufactured by Inui) and 16.0 g of propylene glycol were weighed into a 6K glass bottle. The mixture was stirred and dissolved at room temperature (25°C) to obtain 20 g of liquid.

[0063] Comparative Example 3 4.0 g of Dimer 38 (99% by weight, manufactured by Inui Co.), 15.6 g of propylene glycol, and 0.4 g of Emulgen LS-114 (polyoxyalkylene alkyl ether, manufactured by Kao Corporation) were weighed into a 6K glass bottle. The mixture was stirred and dissolved at room temperature (25°C) to obtain 20 g of liquid.

[0064] (Method for measuring low-temperature stability) The prepared solution was placed in a glass container with a lid (2K glass bottle) and stored in a refrigerator at 5°C for 4 days. After low-temperature storage, the transparency of the solution was evaluated by visual observation under natural light. Furthermore, the fluidity of the solution was evaluated by tilting the container. Note that in Comparative Example 1, dimer 38 was insoluble and therefore could not be measured.

[0065] (Criteria for evaluating low-temperature stability) Low-temperature stability was evaluated according to the following criteria. ○: Maintains a clear solution after low-temperature storage. △: Precipitates are present after low-temperature storage, but the product remains fluid. ×: Solidified and non-fluid due to low-temperature storage.

[0066] [Table 1]

[0067] The details of the abbreviations used in the table are as follows. Dimer 38: N,N'-Hexamethylenebis(4-Carbamoyl-1-decylpyridinium bromide) Emulgen LS-110: Polyoxyalkylene alkyl ether Emulgen LS-114: Polyoxyalkylene alkyl ether Emulgen B-66: Polyoxyethylene tribenzylphenyl ether

Claims

1. N,N'-alkylene-bis(4-carbamoyl-1-alkylpyridinium salt), C ２－４ Alkylene glycol monophenyl ether and Contains, A virus and microbial control agent in which the N,N'-alkylene-bis(4-carbamoyl-1-alkylpyridinium salt) is present in an amount of less than 40% by mass.

2. Said C ２－４ The virus and microbial control agent according to claim 1, wherein the alkylene glycol monophenyl ether is ethylene glycol monophenyl ether.

3. The virus and microbial control agent according to claim 1, wherein the amount of N,N'-alkylene-bis(4-carbamoyl-1-alkylpyridinium salt) is 30% by mass or less.

4. A resin additive comprising a virus / microbial control agent according to any one of claims 1 to 3.

5. A method for controlling viruses and microorganisms using a virus and microorganism control agent described in any one of claims 1 to 3.

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