Anti-biofilm composition or resin member or resin product containing the same

Abstract

To provide an anti-biofilm composition and a resin member or resin product that contains the composition.SOLUTION: Provided is an anti-biofilm composition that comprises an organic phosphorus compound having an aromatic hydrocarbon group (preferably one directly bonded to a phosphorus atom), and also provided is a resin member or resin product containing the composition, which enables continuous manifestation of anti-biofilm performance.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to an anti-biofilm composition or a resin part or resin product containing the composition. [Background technology]

[0002] Biofilms, which are complexes of microorganisms such as bacteria and mold and their metabolic products such as proteins and polymeric polysaccharides, form on solid surfaces that come into contact with water. When biofilms form on pipes in drainage systems or cooling equipment, they can cause problems such as pipe blockages, reduced efficiency of heat exchange equipment, and poor hygiene.

[0003] Although the microorganisms that make up biofilms are themselves sensitive to chemicals such as antibacterial agents and disinfectants, it is known that biofilms become resistant to chemicals once they are formed. Therefore, biofilms are generally removed physically using brushes or chemically using strong acids, strong alkalis, chlorine-based oxidizers, etc. However, physical removal requires regular implementation, which is time-consuming and costly, and chemical removal has limited applicability due to safety and the chemical sensitivity of the target substance.

[0004] Therefore, methods for inhibiting the formation of biofilms on solid surfaces have been investigated, including, for example, a method of physically adsorbing biofilm-inhibiting components onto solid surfaces (e.g., Patent Document 1) or a method of dissolving the components in the circulating water of the equipment (e.g., Patent Document 2). However, the effectiveness of the former is lost when the processed surface is subjected to physical actions such as scraping or abrasion, and the effectiveness of the latter is lost when the circulating water containing the biofilm-inhibiting components is replaced, so there was a demand for improvement in order to achieve a sustained anti-biofilm effect. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Patent No. 7212436 [Patent Document 2] Patent Publication No. 2016-188262 Summary of the Invention [Problem to be solved by the invention]

[0006] After extensive research, the inventors have come to the conclusion that by incorporating an anti-biofilm composition into the resin components that make up the equipment in advance, a sustained anti-biofilm effect can be obtained even if physical effects such as scraping occur on the surface of the resin components.Based on this idea, the inventors have set out to provide an anti-biofilm composition that can be incorporated primarily into resin components and that is capable of exerting this effect, and further to provide resin components and the like that contain this composition. [Means for solving the problem]

[0007] The present inventors have conducted extensive research to solve the above problems and have arrived at the present invention. [1] An anti-biofilm composition containing an organophosphorus compound having an aromatic hydrocarbon group. [2] The anti-biofilm composition described above, which contains an organophosphorus compound having an aromatic hydrocarbon group directly bonded to a phosphorus atom. [3] The above anti-biofilm composition, wherein the organophosphorus compound having an aromatic hydrocarbon group directly bonded to a phosphorus atom is an organophosphorus compound having a structure represented by general formula (1) or general formula (2). TIFF2025156044000001.tif6246 [4] The organic phosphorus compound is an organic phosphorus compound represented by general formula (3), TIFF2025156044000002.tif3445 (wherein X1 to X6 represent hydrogen or a methyl group), An organic phosphorus compound represented by general formula (4) TIFF2025156044000003.tif3445 (wherein X1 to X6 represent hydrogen or a methyl group, and R 2 represents oxygen or a linear or branched hydrocarbon group having 1 to 6 carbon atoms which may have an ester group or a ketone group. and An organophosphorus compound represented by general formula (5) TIFF2025156044000004.tif3446 (wherein X1 to X6 represent hydrogen or a methyl group, and R 1 is a linear, branched or cyclic hydrocarbon group having 1 to 6 carbon atoms which may have an ether group, a carbonyl group or an ester group, and Y represents a halogen. The anti-biofilm composition is an organophosphorus compound selected from the group consisting of: [5] The organic phosphorus compound is an organic phosphorus compound represented by the general formula (3): TIFF2025156044000005.tif3445 (wherein X1 to X6 represent hydrogen or a methyl group), and An organophosphorus compound represented by general formula (5) TIFF2025156044000006.tif3446 (wherein X1 to X6 represent hydrogen or a methyl group, and R 1 is a linear, branched or cyclic hydrocarbon group having 1 to 6 carbon atoms which may have an ether group, a carbonyl group or an ester group, and Y represents a halogen. The anti-biofilm composition is one or more selected from the group consisting of: [6] An anti-biofilm resin member or resin product comprising the above-mentioned anti-biofilm composition. to provide. [Effects of the Invention]

[0008] According to the present invention, an anti-biofilm composition that is compatible with a resin component is formulated, so that anti-biofilm performance can be sustained even if physical action is applied to the surface of the resin component. BEST MODE FOR CARRYING OUT THE INVENTION

[0009] The anti-biofilm composition of the present invention contains an organophosphorus compound having an aromatic hydrocarbon group. Examples of the organophosphorus compound include an organophosphorus compound having an aromatic hydrocarbon group that is not directly bonded to a phosphorus atom, and an organophosphorus compound having an aromatic hydrocarbon group that is directly bonded to a phosphorus atom. Of these, an organophosphorus compound having an aromatic hydrocarbon group that is directly bonded to a phosphorus atom is preferred.

[0010] The organic phosphorus compounds having an aromatic hydrocarbon group directly bonded to the phosphorus atom are particularly those represented by the following general formula (1) or (2): An example is an organophosphorus compound having a structure represented by TIFF2025156044000007.tif6246.

[0011] The organic phosphorus compound having the structure represented by the general formula (1) includes: An organic phosphorus compound represented by general formula (3) TIFF2025156044000008.tif3445 (wherein X1 to X6 represent hydrogen or a methyl group) or An organophosphorus compound represented by the following general formula (4) in which oxygen or the like is bonded to the phosphorus atom of an organophosphorus compound having a structure represented by general formula (1): TIFF2025156044000009.tif3445 (wherein X1 to X6 represent hydrogen or a methyl group, and R 2 represents oxygen or a linear or branched hydrocarbon group having 1 to 6 carbon atoms which may have an ester group or a ketone group. Examples include:

[0012] In addition, the organic phosphorus compound having a structure represented by the general formula (2) is an organic phosphorus compound represented by the following general formula (5): TIFF2025156044000010.tif3446 (wherein X1 to X6 represent hydrogen or a methyl group, and R 1 is a linear, branched or cyclic hydrocarbon group having 1 to 6 carbon atoms which may have an ether group, a carbonyl group or an ester group, and Y represents a halogen. Examples include:

[0013] Examples of the organophosphorus compound represented by the general formula (3) include: Examples include TIFF2025156044000011.tif32139.

[0014] Examples of the organophosphorus compound represented by the general formula (4) include: Examples include TIFF2025156044000012.tif66127.

[0015] Examples of the organophosphorus compound represented by the general formula (5) include: In addition to TIFF2025156044000013.tif9292, Examples include compounds such as TIFF2025156044000014.tif95103.

[0016] Of these, the organic phosphorus compounds represented by the general formula (3) or the organic phosphorus compounds represented by the general formula (5) are preferred.

[0017] The anti-biofilm composition of the present invention can be added directly to the resin component described below, or can be formulated by adding a solvent or the like and then added to the resin component. Examples of the formulation include oil solutions, emulsions, solubilized preparations, wettable powders, dusts, flowable preparations (suspensions in water, emulsions in water, etc.), suspoemulsions, etc.

[0018] Solvents used in such formulations include water, monohydric alcohols such as ethanol, isopropanol, phenoxyethanol, and benzyl alcohol, ethylene glycol, diethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, butylene glycol, diethylene glycol monomethyl ether, diethylene glycol monobutyl ether, dipropylene glycol monomethyl ether, and tripropylene glycol monomethyl ether. Examples of suitable solvents include glycol-based solvents and derivatives thereof, glycerin-based solvents such as glycerin and diglycerin and derivatives thereof, cyclic organic solvents such as dimethyl sulfoxide, N-methylpyrrolidone, N-ethylpyrrolidone, and γ-butyrolactone, ester-based solvents such as phthalates, adipates, and sebacates, aromatic solvents such as methylnaphthalene, phenylxylylethane, and alkylbenzene, aliphatic hydrocarbon solvents such as normal paraffin and isoparaffin, rapeseed oil, cottonseed oil, soybean oil, and castor oil. These solvents may be used alone or in combination of two or more.

[0019] When preparing the formulation, surfactants, pH adjusters, antifoaming agents, rust inhibitors, viscosity adjusters, light stabilizers, ultraviolet absorbers, dispersants, emulsifiers, buffers, antioxidants, other antibacterial components, and the like may be added.

[0020] The anti-biofilm composition of the present invention is mainly blended with a resin component and processed into an anti-biofilm resin member. The resin member exhibits a sustained anti-biofilm effect when used, for example, in piping for cooling equipment or drainage equipment, heat exchange equipment, drain pans for air conditioning systems, etc. The anti-biofilm composition of the present invention can also be incorporated into resin products such as fibers, nonwoven fabrics, paints, surface treatment agents, coating agents, adhesives, films, and plastics.

[0021] The resin component used in the resin member or resin product is not particularly limited and may be any of natural resin, synthetic resin, or semi-synthetic resin, and may also be any of thermoplastic resin or thermosetting resin. Specific resin components include phenol resin, urea resin, melamine resin, epoxy resin, nylon, vinyl chloride resin, polystyrene, AS resin, ABS resin, methacrylic resin, polyethylene resin, polypropylene resin, fluororesin, polyamide resin, polyacetal resin, polycarbonate resin, polysulfone resin, vinyl acetate resin, polyvinyl alcohol resin, polyvinyl acetal resin, etc.

[0022] The blending ratio of the anti-biofilm composition of the present invention to the anti-biofilm resin member or resin product of the present invention is preferably 0.1 to 50 parts by weight, more preferably 0.3 to 20 parts by weight, and more preferably 0.5 to 15 parts by weight, per 100 parts by weight of the resin composition.

[0023] Furthermore, the anti-biofilm resin member or resin product of the present invention may be blended with additives such as stabilizers such as antioxidants and ultraviolet absorption inhibitors, plasticizers, softeners, viscosity regulators, antifouling agents, pigments, dyes, deodorizers, air fresheners, fragrances, spreading agents, rust inhibitors, lubricants, antiblocking agents, surfactants, antistatic agents, vulcanizing agents, vulcanization accelerators, crosslinking agents, foaming agents, fillers, antibacterial agents, antifungal agents, and antiviral agents, as needed.

[0024] A resin member according to one embodiment of the present invention can be produced, for example, by kneading the anti-biofilm composition of the present invention into a thermoplastic resin and molding the resultant mixture.

[0025] For example, the anti-biofilm composition of the present invention, the thermoplastic composition, and other components such as an inorganic filler are melted and kneaded in an extruder such as a single-screw extruder or a twin-screw extruder adjusted to a temperature of typically 60 to 250° C. to prepare a resin composition, and then the resin composition is molded into a predetermined shape by injection molding or the like at a temperature of typically 60 to 220° C. In addition to injection molding, other molding methods such as extrusion molding, press molding, and vacuum molding can also be used.

[0026] Microorganisms targeted by the anti-biofilm composition of the present invention include, for example, Gram-positive bacteria such as Staphylococcus epidermidis and Listeria monocytogenes, and Gram-negative bacteria such as Escherichia coli, Pseudomonas aeruginosa, and Klebsiella pneumoniae. Among these, the composition exhibits excellent anti-biofilm effects against Gram-positive bacteria such as Staphylococcus epidermidis and Listeria monocytogenes, and particularly against Staphylococcus epidermidis. Here, the term "anti-biofilm effect" refers to the inhibition of adhesion of microorganisms to solid surfaces, the inhibition of microbial growth, and the reduction of biofilm formation by killing microorganisms. [Example]

[0027] The present invention will be specifically explained below with reference to examples, but the present invention is not limited to these examples.

[0028] Representative of organophosphorus compounds having aromatic hydrocarbon groups that are not directly bonded to phosphorus atoms TIFF2025156044000015.tif2646, Among the organic phosphorus compounds having an aromatic hydrocarbon group directly bonded to a phosphorus atom, the organic phosphorus compounds represented by the general formula (3) are: TIFF2025156044000016.tif4948, Representative organic phosphorus compounds represented by general formula (4) TIFF2025156044000017.tif4150, Representative organic phosphorus compounds represented by general formula (5) TIFF2025156044000018.tif3647 was used to prepare various anti-biofilm compositions (referred to as Examples 1 to 4, respectively).

[0029] Three parts by weight of each of the antibiofilm compositions of Examples 1 to 4 and 100 parts by weight of polyethylene (PE, Sumikathene FV405, manufactured by Sumitomo Chemical) were kneaded using a kneader (LABOPLASTOMILL 4C150-01, manufactured by Toyo Seiki Seisakusho) at 140°C and 50 rpm for 5 minutes to obtain a resin composition. The resin composition was sandwiched between aluminum plates and pressed at 160°C and 100 kg / cm using a press (model number: AYSR-5, manufactured by Shinto Metal Industries Co., Ltd.). 2 The mixture was pressed at a pressure of 0.5 mm for 180 seconds to form a sheet (thickness 0.5 mm), which was then cut into pieces measuring 3 x 3 cm to prepare resin members (referred to as resin members 1 to 4, respectively).

[0030] (Measurement of anti-biofilm effect) The test bacteria used was Staphylococcus epidermidis ATCC35984 (Staphylococcus epidermidis). SCD liquid medium was manufactured by Nissui Pharmaceutical Co., Ltd., the water-soluble nonwoven fabric was Cross Cook (manufactured by Ozeki Co., Ltd.), and sodium dodecyl sulfate was manufactured by Fujifilm Wako Pure Chemical Industries, Ltd. The test bacteria were cultured overnight with shaking at 37°C in SCD liquid medium, and then diluted to 10% with 1 / 5 concentration of SCD liquid medium. 3 ~10 4 The concentration of CFU / mL was adjusted. Each resin element was heated at 80°C for 3 hours, placed in a sterilized cup, and then immersed and cultured in 20 mL of the bacterial solution at 37°C for 48 hours. After incubation, the resin element was washed with water and then immersed in 20 mL of 0.1% crystal violet solution for 30 minutes to stain the resulting biofilm. After staining, the resin element was washed with water, and the biofilm was wiped off with a water-soluble nonwoven fabric. The collected biofilm was dissolved in 5 mL of 1% sodium dodecyl sulfate solution. The absorbance (590 nm) of the resulting solution was measured using a microplate spectrophotometer (Tecan Japan). The antibiofilm effect was evaluated using the absorbance of the solutions obtained from the drug-added and drug-unadded resin elements (hereinafter referred to as the drug-added and drug-unadded solutions, respectively) using the following equation. Note that a higher activity value indicates a stronger antibiofilm effect.

[0031] Antibiofilm effect value = (1 - "absorbance of drug-added solution" / "absorbance of drug-free solution") x 100

[0032] The above test was repeated three times, and the average value of the antibiofilm effect was calculated. The measurement results are shown in Table 2.

[0033] [Table 2]

Claims

1. An anti-biofilm composition comprising an organophosphorus compound having an aromatic hydrocarbon group.

2. The anti-biofilm composition according to claim 1, which contains an organophosphorus compound having an aromatic hydrocarbon group directly bonded to a phosphorus atom.

3. The anti-biofilm composition according to claim 2, wherein the organophosphorus compound having an aromatic hydrocarbon group directly bonded to a phosphorus atom is an organophosphorus compound having a structure represented by general formula (1) or general formula (2).

4. The organic phosphorus compound according to claim 3 is an organic phosphorus compound represented by general formula (3): (X in the formula １ From X ６ represents hydrogen or a methyl group), An organic phosphorus compound represented by general formula (4) (X in the formula １ From X ６ represents hydrogen or a methyl group, R ２ represents oxygen or a linear or branched hydrocarbon group having 1 to 6 carbon atoms which may have an ester group or a ketone group. and An organic phosphorus compound represented by general formula (5): (X in the formula １ From X ６ represents hydrogen or a methyl group, R １ represents a linear, branched or cyclic hydrocarbon group having 1 to 6 carbon atoms which may have an ether group, a carbonyl group or an ester group, and Y represents a halogen. The anti-biofilm composition is an organophosphorus compound selected from the group consisting of:

5. The organic phosphorus compound according to claim 3 is an organic phosphorus compound represented by general formula (3): (X in the formula １ From X ６ represents hydrogen or a methyl group) and An organic phosphorus compound represented by general formula (5): (X in the formula １ From X ６ represents hydrogen or a methyl group, R １ represents a linear, branched or cyclic hydrocarbon group having 1 to 6 carbon atoms which may have an ether group, a carbonyl group or an ester group, and Y represents a halogen. The anti-biofilm composition is one or more selected from the group consisting of:

6. An anti-biofilm resin member or resin product comprising the anti-biofilm composition according to any one of claims 1 to 5.

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