WO2024024648A1 - 有機色素組成物及びそれを含むスプレー剤 - Google Patents

有機色素組成物及びそれを含むスプレー剤 Download PDF

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Publication number
WO2024024648A1
WO2024024648A1 PCT/JP2023/026696 JP2023026696W WO2024024648A1 WO 2024024648 A1 WO2024024648 A1 WO 2024024648A1 JP 2023026696 W JP2023026696 W JP 2023026696W WO 2024024648 A1 WO2024024648 A1 WO 2024024648A1
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Prior art keywords
organic dye
dye composition
microorganisms
composition according
alcohol
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PCT/JP2023/026696
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English (en)
French (fr)
Japanese (ja)
Inventor
真里 上田
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Panasonic Intellectual Property Management Co Ltd
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Panasonic Intellectual Property Management Co Ltd
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Priority to CN202380056073.XA priority Critical patent/CN119604588A/zh
Priority to JP2024537658A priority patent/JPWO2024024648A1/ja
Publication of WO2024024648A1 publication Critical patent/WO2024024648A1/ja
Priority to US19/021,611 priority patent/US20250154358A1/en
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B19/00—Oxazine dyes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
    • C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
    • C07D265/38—[b, e]-condensed with two six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/10—Spiro-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/06—Hydroxy derivatives of triarylmethanes in which at least one OH group is bound to an aryl nucleus and their ethers or esters
    • C09B11/08—Phthaleins; Phenolphthaleins; Fluorescein
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/28—Pyronines ; Xanthon, thioxanthon, selenoxanthan, telluroxanthon dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0083—Solutions of dyes
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
    • G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
    • G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
    • G01N21/64—Fluorescence; Phosphorescence
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
    • G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
    • G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
    • G01N21/64—Fluorescence; Phosphorescence
    • G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
    • G01N21/75—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated
    • G01N21/77—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
    • G01N21/75—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated
    • G01N21/77—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator
    • G01N21/78—Systems in which material is subjected to a chemical reaction, the progress or the result of the reaction being investigated by observing the effect on a chemical indicator producing a change of colour
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
    • G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
    • G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
    • G01N21/64—Fluorescence; Phosphorescence
    • G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
    • G01N2021/6439—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" with indicators, stains, dyes, tags, labels, marks

Definitions

  • the present invention relates to an organic pigment composition and a spray containing the same.
  • Patent Document 1 adenosine phosphate esters in the sample are caused to emit light by the interaction of a sample wiped from the measurement target with a luminescent reagent, and by measuring the amount of luminescence, the degree of contamination of the measurement target can be determined. Measuring cleanliness and evaluating the cleanliness is disclosed. Further, Patent Document 2 describes a method for detecting the presence of bacterial spores of microorganisms by culturing a sample and measuring the metabolic activity of microorganisms in the sample using a metabolic dye or the like.
  • Patent Document 3 reports a method for detecting viable bacteria, which involves bringing a microbial cell sample into contact with a fluorescent indicator, etc., which is an indicator of intracellular esterase activity, and detecting a light spot generated by irradiating excitation light. has been done.
  • Patent Document 3 requires a step of collecting microbial cells using a membrane filter, and it takes time to prepare the specimen.
  • the present invention was made in view of these circumstances, and its main purpose is to provide a practical tool that can easily check the disinfection effect and the presence of microorganisms over a wide area in a short time.
  • the organic dye composition according to one aspect of the present invention includes an organic dye (A) that changes color upon hydrolysis and emits fluorescence when excited by excitation light with a wavelength of 400 nm or more and 550 nm or less, alcohol (B), and water (C ), the content of the organic dye (A) is 1 ⁇ mol/L or more, and the viscosity is 5 mPa ⁇ s or more and 45 mPa ⁇ s or less.
  • a spray agent according to another aspect of the present invention is characterized by containing the organic pigment composition.
  • FIG. 1 is a block diagram showing an example of a microorganism visualization system using the organic dye composition of this embodiment.
  • FIG. 2 is a block diagram showing another example of a microorganism visualization system using the organic dye composition of this embodiment.
  • FIG. 3 is a block diagram showing yet another example of a microorganism visualization system using the organic dye composition of this embodiment.
  • the organic dye composition of this embodiment contains an organic dye (A), an alcohol (B), and water (C).
  • the content of the organic dye (A) is 1 ⁇ mol/L or more, and the viscosity is 5 mPa ⁇ s or more and 45 mPa ⁇ s or less.
  • the organic dye (A) changes color due to hydrolysis and emits fluorescence when excited by excitation light with a wavelength of 400 nm or more and 550 nm or less.
  • Such an organic pigment composition is useful as a spray agent because it has a viscosity within the above range, and can be sprayed over a wide range. Furthermore, since the organic dye composition of the present embodiment contains 1 ⁇ mol/L or more of the organic dye (A), when the organic dye composition comes into contact with microorganisms, it undergoes hydrolysis and discolors, causing wavelengths of 400 nm to 550 nm. It emits fluorescence with the following excitation light. First, the presence or absence of microorganisms can also be confirmed by visually observing the discoloration caused by the hydrolysis.
  • organic pigments (A) usually emit light within 1 to 15 minutes after being sprayed, depending on the concentration of microorganisms, so for example, by shining a green or red LED light on the spraying area, it can be used over a wide area.
  • the presence or absence of microorganisms can be quickly and easily visually confirmed. Therefore, with the organic dye composition of the present embodiment, it is possible to easily check the disinfection effect over a wide range and the presence of microorganisms in a short time. Furthermore, since detection by light irradiation has very high sensitivity, microorganisms can be detected even in low microorganism concentration areas where the discoloration cannot be visually confirmed.
  • an organic pigment composition and a spray using the same which can be used as a practical tool that can easily check the disinfection effect over a wide range and the presence of microorganisms in a short time.
  • the viscosity of the organic pigment composition is further set to 8 mPa ⁇ s or more and 45 mPa. - It is preferable that it is s or less.
  • the organic dye (A) of this embodiment is an organic dye that changes color due to hydrolysis and emits fluorescence when excited by excitation light with a wavelength of 400 nm or more and 550 nm or less.
  • “Changes color due to hydrolysis” means that when the organic dye (A) comes into contact with microorganisms, it is hydrolyzed by an enzymatic reaction within the cells of the microorganisms, resulting in a color different from that of the dye molecules before being hydrolyzed.
  • the molecular structure is as follows. In other words, when the organic dye (A) comes into contact with microorganisms, its molecular structure changes and its absorption spectrum in the visible light region changes.
  • emits fluorescence with excitation light having a wavelength of 400 nm or more and 550 nm or less means exhibiting red fluorescence or a red color at an excitation wavelength of approximately 400 to 500 nm, or exhibiting green fluorescence or a green color at an excitation wavelength of approximately 450 to 550 nm. It means that.
  • any organic dye may be used as long as it has the above-mentioned characteristics, and for example, an organic dye for staining living cells can be used. More specifically, it is preferably at least one compound selected from the following formulas (1) to (5).
  • the organic dyes described above exhibit esterase activity and are not toxic, so they can be used safely.
  • the organic dye (A) can be used alone or in combination of two or more.
  • the content of the organic dye (A) is 1 ⁇ mol/L or more.
  • the content of the organic dye (A) is within the above range, microorganisms and the like can be detected more reliably. More preferably, the content of the organic dye (A) is 10 ⁇ mol/L or more. Further, although there is no particular need to set an upper limit to the content, from the viewpoint of further suppressing cytotoxicity, it is preferably 100 ⁇ mol/L or less.
  • the organic dye composition of this embodiment contains alcohol (B) in order to impart moisturizing properties and thickening properties to the composition.
  • alcohol (B) By containing alcohol (B), the viscosity of the organic dye composition of this embodiment can be set to 5 mPa ⁇ s or more and 45 mPa ⁇ s or less.
  • the alcohol (B) also plays the role of fixing the composition to the object and preventing evaporation.
  • the alcohol (B) is not particularly limited as long as it is an alcohol that can adjust the viscosity of the organic dye composition to 5 mPa-s or more and 45 mPa-s or less; Preferably.
  • the alcohol (B) of this embodiment contains an alcohol with a boiling point of 180°C or higher.
  • the contact angle of the organic dye composition of this embodiment with respect to the above-mentioned object can be made 90 degrees or less, and the wettability of the organic dye composition can be improved.
  • the boiling point is 180° C. or higher, it is considered that the volatility of the organic dye composition can be suppressed and the composition can be prevented from drying out quickly.
  • alcohol (B) examples include glycerin, propanediol, butanediol, pentanediol, hexanediol, heptanediol, butanetriol, pentanetriol, hexanetriol, heptanetriol, etc.
  • glycerin propanediol, butanediol, pentanediol, hexanediol, heptanediol, butanetriol, pentanetriol, hexanetriol, heptanetriol, etc.
  • the content of alcohol (B) is preferably 50% by mass or more based on the entire organic dye composition. It is thought that this makes it possible to more reliably set the viscosity, contact angle, wettability, etc. in a suitable range as described above.
  • a more preferable content of alcohol (B) is 60% by mass or more, more preferably 80% by mass or more.
  • the upper limit of the content is not particularly limited, but is preferably 90% by mass or less from the viewpoint of suppressing nozzle clogging during spraying, which is characteristic of high viscosity.
  • the organic dye composition of this embodiment further contains water (C).
  • the role of water (C) in this embodiment is a biocompatible solvent.
  • water (C) ordinary purified water, distilled water, ion exchange water, sterilized water, etc. can be used.
  • the content of water (C) in the organic dye composition of this embodiment is preferably 5% by mass or more and 50% by mass or less based on the entire resin composition. This has the advantage of uniformly dissolving the components in the organic dye composition. A more preferable content is 5% by mass or more and 40% by mass or less.
  • the organic dye composition of the present embodiment may contain various additives and the like within a range that does not impair the effects of the present invention.
  • additives that do not have bactericidal activity are preferred. This is because, when the organic dye composition has a bactericidal effect, when it acts on microorganisms, it may inactivate or kill the living cells of the microorganisms before they are sufficiently dyed.
  • additives include binder resins, surfactants, pH adjusters, thickeners, ultraviolet absorbers, ultraviolet scattering agents, oxygen scavengers, antioxidants, fragrances, alcohols, and solvents other than water.
  • the binder resin functions to improve the fixability and wetting spread of droplets on the spray target when the organic dye composition is sprayed.
  • the binder resin that can be used in this embodiment is not particularly limited as long as it does not cause skin irritation and can be stably and uniformly dispersed in water or alcohol. From the viewpoint of skin irritation, it is preferable to select ingredients listed in the list of ingredient labeling names for cosmetics based on the Pharmaceutical Affairs Law.
  • the organic dye composition of this embodiment contains a surfactant
  • the surfactant functions to uniformly disperse and dissolve the composition in the solution.
  • the surfactant is not particularly limited as long as it does not irritate the skin and can be stably and uniformly dispersed in water or alcohol, but it is preferable to use a surfactant that does not have a bactericidal effect. This is because, when the organic dye composition has a bactericidal effect, when it acts on microorganisms, it may inactivate or kill the living cells of the microorganisms before they are sufficiently dyed.
  • surfactants that do not have a bactericidal effect include anionic surfactants, amphoteric surfactants, and nonionic surfactants.
  • anionic surfactants include carboxylates, sulfonates, sulfate ester salts, and the like.
  • amphoteric surfactants include amino acid type or betaine type carboxylates.
  • nonionic surfactants include glycerin fatty acid ester, sorbitan fatty acid ester, sucrose fatty acid ester, polyoxyethylene alkyl ether, polyoxyethylene alkyl phenyl ether, polyoxyethylene polyoxypropylene glycol, and the like.
  • the HLB value of the surfactant used in this embodiment is preferably 8 or more, and more preferably 8 to 19.
  • the HLB value of the surfactant is 8 or more, the surfactant is easily dispersed or dissolved uniformly in higher alcohol, purified water, and the like.
  • the HLB value is an index representing the ratio of relative affinities for both liquids in an oil-water system, and generally speaking, the higher the HLB value, the higher the affinity for water. Note that the HLB value in this specification is a value calculated by the Griffin method.
  • the method for preparing the organic dye composition of this embodiment is not particularly limited.
  • it can be prepared by adding the organic dye (A) and alcohol (B) to a predetermined amount of water (C) and stirring.
  • organic dye composition of this embodiment can visualize the presence or absence of microorganisms, and therefore can be used for applications such as detection of microorganisms and confirmation of disinfection effects. Therefore, it is preferable to use it as a spray agent that can be sprayed and distributed over a wide range. By using a spray agent, microorganisms can be detected quickly and easily in the object to which it is applied.
  • the organic dye composition of the present embodiment has a contact angle of 90° or less with respect to stainless steel, artificial marble, quartz, resin, enamel, wood, etc. that constitute these objects.
  • the contact angle is 90° or less, the wettability of the organic dye composition to the object increases.
  • a more preferable contact angle is 80° or less, more preferably 70° or less.
  • the spray of this embodiment is not particularly limited as long as it contains the above-mentioned organic pigment composition.
  • a spray can be obtained by filling a spray container with the organic dye composition of this embodiment.
  • a sealable light-shielding container of 0.1 to 20 L is preferable because it is convenient to carry.
  • the material for the container include polyethylene terephthalate (PET), polypropylene (PP), polyethylene (PE), glass, and the like.
  • PET polyethylene terephthalate
  • PP polypropylene
  • PE polyethylene
  • glass glass
  • the container needs to be shielded from light.
  • a colored light-shielding container may be used as the container, or the surface of the light-transmitting container may be coated with a light-shielding film or thin film (such as aluminum foil).
  • the spray container is preferably a container with a trigger nozzle so that spraying and dispersion can be easily performed.
  • the disinfection effect and presence of microorganisms can be easily checked in a short time over a wide area.
  • the organic dye composition and spray of this embodiment are useful in various uses.
  • the organic dye composition and spray of this embodiment can be incorporated into a system that visualizes the presence or absence of microorganisms, and such a visualization system can be applied, for example, to cleaning houses.
  • FIG. 1 is a block diagram showing a schematic configuration example of a microorganism visualization system (microorganism visualization method) using an organic dye composition according to the present embodiment.
  • the organic dye composition 1 according to the present embodiment is applied to the object 2 on which the presence or absence of microorganisms is to be detected by spraying or the like.
  • the organic dye composition 1 of this embodiment reacts with the microorganisms to produce a hydrolyzate, causing discoloration. By visually checking the presence or absence of discoloration, the presence or absence of microorganisms in the object can be easily investigated.
  • FIG. 2(A) is a block diagram showing another configuration example of the microorganism visualization system (microorganism visualization method) using the organic dye composition according to the present embodiment.
  • this microorganism visualization system after attaching the organic dye composition 1 according to the present embodiment to an object 2 whose presence or absence of microorganisms is to be detected by spraying or the like, Light is irradiated using a light source 3 that emits light.
  • the hydrolyzate of the organic dye (A) emits fluorescence upon irradiation of the light, and the attached location changes color, making it possible to visually recognize the location where the microorganism is present. .
  • the microorganism visualization system may further include a filter, as shown in FIG. 2(B).
  • a filter As shown in FIG. 2(B), after light is irradiated onto the object 2 from the light source 3, the location where the microorganism is present is visually recognized through the filter 4.
  • the filter 4 is capable of filtering the wavelength of the light source 3. Visibility can be improved by cutting off reflected light from the light source 3 using the filter 4.
  • the filter 4 may have a function of filtering ultraviolet light or blue light. This filters out harmful wavelengths of light, protecting your eyes and improving visibility.
  • the microorganism visualization system may have a system configuration including a camera, as shown in the block diagram shown in FIG. 3. By using a camera, the presence or absence of microorganisms can be confirmed from the captured images.
  • the system further includes an imaging unit 5 that images the object 2, a signal processing unit 6 that processes the signal obtained from the imaging unit 5, a storage unit 9 that holds brightness information related to microorganisms, and an image capturing unit 5 that images the object 2. It includes an image generation section 7 that generates an image, and a display section 8 that displays the generated image.
  • the signal processing unit 6 determines the presence or absence of microorganisms based on the brightness information obtained from the imaging unit and the brightness information related to microorganisms held in the storage unit (microorganism determination unit 10).
  • the image generation unit 7 generates an image based on the processing results in the signal processing unit 6. At this time, based on the microorganism determination information, an image may be generated that emphasizes a region determined to contain microorganisms. Specifically, it is conceivable to change the color tone and contrast of areas determined to contain microorganisms to be more easily recognized.
  • the location where the microorganism is present can be easily identified.
  • the present embodiment also includes the following aspects (microorganism visualization method and microorganism visualization system).
  • First application example Contains an organic dye (A) that changes color due to hydrolysis and emits fluorescence when excited by excitation light with a wavelength of 400 nm or more and 550 nm or less, alcohol (B), and water (C),
  • the content of the organic dye (A) is 1 ⁇ mol/L or more
  • the viscosity is 5 mPa ⁇ s or more and 45 mPa ⁇ s or less, attaching an organic dye composition to an object; irradiating the object with light having a wavelength of 400 nm or more and 550 nm or less from a light source; Microbial visualization method.
  • a microorganism visualization system that visualizes microorganisms by attaching an organic dye composition to a target object, a light source that irradiates light onto a target object; an imaging unit that images the target object and obtains first brightness information; a storage unit that holds second brightness information related to microorganisms;
  • a microorganism visualization system comprising: a signal processing unit that compares the luminance information with second luminance information to determine the presence or absence of microorganisms; an image generation unit that generates an image from the signal; and a display unit that displays the generated image;
  • the organic dye composition according to the first aspect of the present invention includes an organic dye (A) that changes color upon hydrolysis and emits fluorescence when excited by excitation light with a wavelength of 400 nm or more and 550 nm or less, alcohol (B), and water ( C), the content of the organic dye (A) is 1 ⁇ mol/L or more, and the viscosity is 5 mPa ⁇ s or more and 45 mPa ⁇ s or less.
  • the organic pigment composition according to the second embodiment further has a contact angle of 90° or less with respect to at least one selected from stainless steel, artificial marble, quartz, resin, and enamel. be.
  • the organic dye composition according to the third aspect is the organic dye composition according to the first and second aspects, wherein the organic dye (A) is selected from the compounds represented by formulas (1) to (5) above. At least one of the organic dye (A) is selected from the compounds represented by formulas (1) to (5) above. At least one of the organic dye (A) is selected from the compounds represented by formulas (1) to (5) above. At least one of the organic dye (A) is selected from the compounds represented by formulas (1) to (5) above. At least one of the organic dye (A) is selected from the compounds represented by formulas (1) to (5) above. At least one of the organic dye (A) is selected from the compounds represented by formulas (1) to (5) above. At least one of the organic dye (A) is selected from the compounds represented by formulas (1) to (5) above. At least one of the organic dye (A) is selected from the compounds represented by formulas (1) to (5) above. At least one of the organic dye (A) is selected from the compounds represented by formulas (1) to (5) above. At least one of the organic dye (A
  • the alcohol (B) contains an alcohol having a boiling point of 180° C. or higher.
  • the organic dye composition according to the fifth aspect is the organic dye composition according to the fourth aspect, in which the alcohol is at least one selected from glycerin and propanediol.
  • the organic dye composition according to the sixth aspect is the organic dye composition according to the fourth and fifth aspects, in which the content of alcohol (B) is 50% by mass or more based on the entire organic dye composition. .
  • the spray according to the seventh aspect of the present invention contains the organic pigment composition according to any one of the first to sixth aspects.
  • a microorganism visualization method includes attaching the organic dye composition according to any one of the first to sixth aspects to an object, and emitting light with a wavelength of 400 nm or more and 550 nm or less to the object. It is characterized by being irradiated with a light source.
  • the microorganism visualization method according to the ninth aspect of the present invention is the microorganism visualization method according to the eighth aspect, further comprising observing the target object through a filter after irradiating the light.
  • a microorganism visualization system is a microorganism visualization system that visualizes microorganisms by attaching the organic dye composition of any one of the first to sixth aspects to an object, a light source that irradiates light onto a target object; an imaging unit that images the target object and obtains first brightness information; a storage unit that holds second brightness information related to microorganisms; It is characterized by comprising a signal processing unit that compares the second brightness information and determines the presence or absence of microorganisms, an image generation unit that generates an image from the signal, and a display unit that displays the generated image.
  • the evaluation criteria were as follows: ⁇ : The luminescence of the solution can be clearly recognized with the naked eye. ⁇ : The luminescence of the solution can be visually recognized, but it is very weak. ⁇ : The luminescence of the solution cannot be visually recognized. - Color change Visually observe the color change, Evaluated using the following criteria: ⁇ : The color change of the solution can be clearly recognized with the naked eye. ⁇ : The color change of the solution can be visually recognized, but it is extremely weak. ⁇ : The color change of the solution cannot be visually recognized, or there is no color change.
  • Viscosity The viscosity (mPa ⁇ s) of the sample solutions (organic dye compositions) of each Example and Comparative Example was measured using a rheometer (cone-plate viscometer). The measurement conditions were a shear rate of 1000 [1/s] and 25°C.
  • the evaluation criteria were as follows: ⁇ : The organic dye was not decomposed in the solution and was stable for more than 2 hours (fluorescence could not be visually recognized after 2 hours) ⁇ : The organic dye was decomposed over time in the solution, and fluorescence was visible after 2 hours.
  • the dye shown by formula (4) shows a clearer color change upon irradiation with light in the detection of both E. coli and Staphylococcus aureus than the dye shown by formula (2). I was able to see it. Further, as for the alcohol (B), it was found that fluorescence emission and color change upon irradiation of light could be more clearly confirmed with glycerin than with propanediol.
  • the disinfection effect and the presence of microorganisms can be easily checked over a wide area in a short time. availability.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
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JPH07135996A (ja) * 1993-11-19 1995-05-30 Mitsubishi Chem Corp 生細胞の検出方法
JP2006029793A (ja) * 2004-07-12 2006-02-02 Matsushita Electric Ind Co Ltd 生菌検出方法および生菌計数装置
JP2006238779A (ja) * 2005-03-03 2006-09-14 Matsushita Electric Ind Co Ltd 微生物細胞検出方法
JP2012187101A (ja) * 2011-02-25 2012-10-04 Kao Corp 尿臭発生部の視覚的判定方法
JP2017062238A (ja) * 2010-11-30 2017-03-30 コンバテック・テクノロジーズ・インコーポレイテッドＣｏｎｖａｔｅｃ Ｔｅｃｈｎｏｌｏｇｉｅｓ Ｉｎｃ 生組織におけるバイオフィルムを検出するための組成物
JP2018011544A (ja) * 2016-07-20 2018-01-25 パナソニックＩｐマネジメント株式会社 微生物検出方法及び微生物検出装置
CN108047135A (zh) * 2017-12-29 2018-05-18 苏州宇恒生物科技有限公司 一种荧光染料及其制备方法与在细菌检测中的应用
JP2021054084A (ja) * 2016-01-15 2021-04-08 東洋インキＳｃホールディングス株式会社 前処理液、インキセット、及び印刷物の製造方法
JP2021161391A (ja) * 2020-03-30 2021-10-11 ユニチカ株式会社 水性塗剤、塗膜、および積層体
JP2021192594A (ja) * 2020-06-08 2021-12-23 住友ベークライト株式会社 被検試料中に微生物が存在するか否かを判定する方法及び微生物検出剤

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH07135996A (ja) * 1993-11-19 1995-05-30 Mitsubishi Chem Corp 生細胞の検出方法
JP2006029793A (ja) * 2004-07-12 2006-02-02 Matsushita Electric Ind Co Ltd 生菌検出方法および生菌計数装置
JP2006238779A (ja) * 2005-03-03 2006-09-14 Matsushita Electric Ind Co Ltd 微生物細胞検出方法
JP2017062238A (ja) * 2010-11-30 2017-03-30 コンバテック・テクノロジーズ・インコーポレイテッドＣｏｎｖａｔｅｃ Ｔｅｃｈｎｏｌｏｇｉｅｓ Ｉｎｃ 生組織におけるバイオフィルムを検出するための組成物
JP2012187101A (ja) * 2011-02-25 2012-10-04 Kao Corp 尿臭発生部の視覚的判定方法
JP2021054084A (ja) * 2016-01-15 2021-04-08 東洋インキＳｃホールディングス株式会社 前処理液、インキセット、及び印刷物の製造方法
JP2018011544A (ja) * 2016-07-20 2018-01-25 パナソニックＩｐマネジメント株式会社 微生物検出方法及び微生物検出装置
CN108047135A (zh) * 2017-12-29 2018-05-18 苏州宇恒生物科技有限公司 一种荧光染料及其制备方法与在细菌检测中的应用
JP2021161391A (ja) * 2020-03-30 2021-10-11 ユニチカ株式会社 水性塗剤、塗膜、および積層体
JP2021192594A (ja) * 2020-06-08 2021-12-23 住友ベークライト株式会社 被検試料中に微生物が存在するか否かを判定する方法及び微生物検出剤

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