Organic pigment composition and spray comprising same

Abstract

One aspect of the present invention relates to an organic dye composition containing: an organic dye (A) that changes color by hydrolysis and emits fluorescence by excitation light having a wavelength of 400-550 nm (inclusive); an alcohol (B); and water (C), in which the content of the organic dye (A) is 1 [mu] mol / L or more, and the viscosity is 5-45 mPa.s (inclusive).

Description

Technical Field

[0001] The present invention relates to an organic pigment composition and a spray containing the same. Background Art

[0002] Currently, the premise of public health has changed from "safe" to "dangerous", and the threat of invisible microorganisms has increased to an unprecedented level. Although the hands and all parts that the hands touch are disinfected, the scale of the disinfection effect is not visible to the naked eye, so there is a problem that it is difficult to distinguish the appropriate level of disinfection measures. The fear of invisible microorganisms varies from person to person, and some people do not take sufficient disinfection measures, or those who are more anxious will take excessive measures beyond necessity. For this reason, a practical tool that can easily display the effect of disinfection measures is needed.

[0003] So far, methods using luminescent reagents or fluorescent indicators are known as methods for measuring cleanliness and detecting microorganisms. For example, Patent Document 1 discloses the following: by reacting a sample wiped from a measurement object with a luminescent reagent, adenosine phosphates in the sample emit light, and the amount of light emitted is measured, thereby measuring the contamination and cleanliness of the object and evaluating the cleanliness. In addition, Patent Document 2 describes a method for the following purpose: culturing a sample, and using metabolic pigments to measure the metabolic activity of microorganisms in the sample, thereby detecting the presence of bacterial spores of microorganisms. In addition, Patent Document 3 reports a method for detecting live bacteria, which includes the step of detecting a light spot generated by contacting a microbial cell sample with a fluorescent indicator of intracellular esterase activity and irradiating it with excitation light.

[0004] However, in the technique described in Patent Document 1, since the sample is obtained by wiping from the measurement object, the microbial concentration can be grasped only in the wiped area. Therefore, the applicability of the disinfection effect in a wide range cannot be expected.

[0005] Furthermore, the technology described in Patent Document 2 has the limitation that the concentration of microorganisms can be determined only in the area where the sample is collected, and further requires a step of culturing the microorganisms contained in the specimen, which takes time to obtain the results, and is therefore not practical.

[0006] Furthermore, the technique described in Patent Document 3 requires a step of capturing microbial cells using a membrane filter, and thus requires a lot of time to prepare a specimen.

[0007] The present invention has been made in view of this actual situation, and its main object is to provide a practical tool that can easily check the disinfection effect and the presence of microorganisms in a wide range in a short time.

[0008] Prior art literature

[0009] Patent Literature

[0010] Patent Document 1: Japanese Patent Publication No. 2003-35673

[0011] Patent Document 2: Japanese Patent Publication No. 2020-530286

[0012] Patent Document 3: Japanese Patent Publication No. 2006-238779 Summary of the invention

[0013] As a result of intensive studies, the present inventors have found that the above-mentioned problems can be solved by an organic dye composition having the following structure. Based on this finding, the present inventors have conducted further studies and have completed the present invention.

[0014] That is, one aspect of the present invention relates to an organic pigment composition, which contains: an organic pigment (A) that changes color by hydrolysis and emits fluorescence by excitation light with a wavelength of greater than 400 nm and less than 550 nm; an alcohol (B); and water (C), wherein the content of the organic pigment (A) is greater than 1 μmol / L and the viscosity is greater than 5 mPa·s and less than 45 mPa·s.

[0015] In addition, another aspect of the present invention relates to a spray containing the above-mentioned organic pigment composition. BRIEF DESCRIPTION OF THE DRAWINGS

[0016] Figure 1 This is a block diagram showing an example of a microorganism visualization system using the organic pigment composition according to the present embodiment.

[0017] Figure 2 This is a block diagram showing another example of the microorganism visualization system using the organic pigment composition according to the present embodiment.

[0018] Figure 3 This is a block diagram showing another example of the microorganism visualization system using the organic pigment composition according to the present embodiment. DETAILED DESCRIPTION

[0019] Hereinafter, embodiments of the present invention will be described in detail, but the present invention is not limited to these embodiments.

[0020] (Organic pigment composition)

[0021] The organic pigment composition of the present embodiment contains an organic pigment (A), an alcohol (B) and water (C). In the above-mentioned organic pigment composition, the content of the organic pigment (A) is 1 μmol / L or more, and the viscosity is 5 mPa·s or more and 45 mPa·s or less. The organic pigment (A) changes color by hydrolysis and emits fluorescence by excitation light with a wavelength of 400 nm or more and 550 nm or less.

[0022] This organic pigment composition is useful as a spray because of the viscosity with the above-mentioned range, and can be sprayed in a wide range. In addition, owing to include the organic pigment (A) above 1 μ mol / L in the organic pigment composition of the present embodiment, when the organic pigment composition contacts with the microorganism, hydrolysis occurs and changes color, and emits fluorescence under the excitation light of more than 400nm and less than 550nm of wavelength. First, by visually recognizing the color change caused by the above-mentioned hydrolysis, it is possible to confirm the presence or absence of microorganisms. And, although the organic pigment (A) also depends on the concentration of the microorganism, it will usually emit light about 1 to 15 minutes after spraying, so for example, by irradiating the spraying place with green or red LED lights, etc., it is possible to quickly and easily visually recognize the presence or absence of microorganisms in a wide range. Therefore, by the organic pigment composition of the present embodiment, it is possible to easily check the disinfection effect and the presence or absence of microorganisms in a wide range in a short time. In addition, since the detection sensitivity based on light irradiation is very high, even if the microorganism low concentration area of ​​the above-mentioned color change cannot be confirmed visually, microorganisms can be detected.

[0023] Therefore, according to the present embodiment, an organic pigment composition and a spray using the same can be provided, wherein the organic pigment composition can be used as a practical tool that can easily check the disinfection effect and the presence of microorganisms in a wide range in a short time.

[0024] From the viewpoint of reducing the rebound and rolling of droplets from the spray target when the organic dye composition is sprayed and improving the fixation, the viscosity of the organic dye composition is more preferably 8 mPa·s or more and 45 mPa·s or less.

[0025] Hereinafter, each component contained in the organic dye composition will be described.

[0026] Organic pigment (A)

[0027] As described above, the organic pigment (A) of the present embodiment is an organic pigment that changes color by hydrolysis and emits fluorescence by excitation light with a wavelength of more than 400nm and less than 550nm. "Change color by hydrolysis" means that when the organic pigment (A) contacts with a microorganism, it is hydrolyzed by an enzyme reaction in the microbial cell, and the result is: a molecular structure showing a different color from the pigment molecule before being hydrolyzed. That is, the organic pigment (A) is a pigment whose molecular structure changes when it contacts with a microorganism, and whose absorption spectrum in the visible light region changes.

[0028] In this specification, "emitting fluorescence due to excitation light with a wavelength of 400 nm to 550 nm" means: generating red fluorescence and / or appearing red at an excitation wavelength of about 400 to 500 nm, or generating green fluorescence and / or appearing green at an excitation wavelength of about 450 to 550 nm.

[0029] As the organic dye (A), any organic dye can be used as long as it has the above-mentioned properties, and for example, an organic dye for staining living cells can be used. More specifically, for example, at least one selected from the compounds represented by the following formulae (1) to (5) is preferred.

[0030]

[0031] Compound name: 5-(6)-Carboxyfluorescein diacetate (CFDA)

[0032]

[0033] Compound name: 3',6'-di(O-acetyl)-4',5'-bis[N,N-bis(carboxymethyl)aminomethyl]fluorescein tetraacetoxymethyl ester (Calcein-AM)

[0034]

[0035] Compound name: 5- or 6-(N-succinimidyloxycarbonyl)fluorescein 3',6'-diacetate (CFSE)

[0036]

[0037] Compound name: 7-isobutoxycarbonyloxy-3H-phenoxazine-3-one (CytoRed)

[0038]

[0039] Compound Name: Fluorescein diacetate (FDA)

[0040] The organic pigments described above show esterase activity and are non-toxic, and therefore can be used safely.

[0041] The organic dye (A) may be used alone or in combination of two or more.

[0042] In the organic pigment composition of the present embodiment, the content of organic pigment (A) is more than 1 μmol / L. By making the content of organic pigment (A) be the above-mentioned scope, the detection of microorganisms etc. can be more reliably carried out. The content of organic pigment (A) is more preferably more than 10 μmol / L. In addition, for the above-mentioned content, it is not necessary to set the upper limit in particular, but from the viewpoint of further suppressing cytotoxicity, it is preferably below 100 μmol / L.

[0043] Alcohol (B)

[0044] In order to impart moisture retention and viscosity enhancement to the composition, the organic pigment composition of the present embodiment contains alcohol (B). By containing alcohol (B), the viscosity of the organic pigment composition of the present embodiment can be made to be 5 mPa·s or more and 45 mPa·s or less. In addition, when the organic pigment composition is spread on an object, the alcohol (B) also serves to fix the composition to the object and prevent evaporation.

[0045] In the present embodiment, the alcohol (B) is not particularly limited as long as it can adjust the viscosity of the organic dye composition to 5 mPa·s or more and 45 mPa·s or less, but a biocompatible alcohol is preferred from the viewpoint of safety.

[0046] It is preferred that the alcohol (B) of the present embodiment contains an alcohol having a boiling point of 180° or more. Thus, the contact angle of the organic pigment composition of the present embodiment relative to the above-mentioned object can be made below 90°, and the wettability of the organic pigment composition can be improved. In addition, it is believed that if the above-mentioned boiling point is above 180°, the volatility of the organic pigment composition can be suppressed, and the composition can be suppressed from drying immediately, etc.

[0047] Suitable specific examples of alcohol (B) include glycerol, propylene glycol, butylene glycol, pentanediol, hexanediol, heptanediol, butanetriol, pentanetriol, hexanetriol, heptanetriol, etc. Among them, glycerol and / or propylene glycol are preferably used from the viewpoint of safety. In addition, glycerol is preferably used from the viewpoint of more reliable detection of microorganisms, etc.

[0048] With respect to the organic pigment composition as a whole, the content of alcohol (B) is preferably more than 50 quality %.Thus, think: aforesaid viscosity, contact angle, wettability etc. can be set to suitable scope more reliably.The more preferred content of alcohol (B) is more than 60 quality %, further preferably more than 80 quality %.In addition, for the upper limit of content, there is no particular limitation, but from the viewpoint that nozzle clogging when distinctive spraying is suppressed in the time of high viscosity, is preferably below 90 quality %.

[0049] Water (C)

[0050] The organic dye composition of the present embodiment further contains water (C). The water (C) of the present embodiment functions as a biocompatible solvent.

[0051] As water (C), ordinary purified water, distilled water, ion-exchanged water, sterilized water, etc. can be used.

[0052] Relative to the whole resin composition, the content of the water (C) in the organic pigment composition of the present embodiment is preferably more than 5 mass % and below 50 mass %.Thus, there is the advantage that the component in the organic pigment composition is uniformly dissolved.Preferred content is more than 5 mass % and below 40 mass %.

[0053] ·other

[0054] The organic pigment composition of present embodiment can also contain various additives etc. in the scope that does not damage effect of the present invention except above-mentioned composition.Particularly, as additive, preferably do not have the additive of bactericidal effect.The reason is: under the situation of having bactericidal effect, when making the organic pigment composition act on microorganism, the living cell of microorganism might be inactivated or dead before fully dyeing.As additive, can enumerate binder resin, surfactant, pH adjusting agent, thickening agent, ultraviolet light absorber, ultraviolet light scattering agent, deoxidant, antioxidant, spices, solvent etc. except alcohol and dewatering.

[0055] For example, when the organic pigment composition of the present embodiment comprises a binder resin, the binder resin plays a role in improving the fixity and wet expansibility of droplets to the spray object when spraying the organic pigment composition. As the binder resin that can be used in the present embodiment, there is no particular restriction as long as there is no skin irritation, in water and in alcohol, the binder resin that can be stably and uniformly dispersed. From the viewpoint of skin irritation, it is preferred to select from the ingredients listed in the list of ingredient names of cosmetics based on the Pharmaceutical Affairs Law, preferably: known acrylic resins suitable for cosmetics, such as acrylic acid, methyl acrylate, ethyl acrylate, acrylamide, n-propyl acrylate, n-butyl acrylate, isobutyl acrylate, octyl acrylate, 2-ethylhexyl acrylate, N,N-dimethylaminoethyl acrylate, acrylonitrile, methacrylic acid, ethyl methacrylate, methacrylamide, n-propyl methacrylate, n-butyl methacrylate, isobutyl methacrylate, 2-ethylhexyl methacrylate, octyl methacrylate, hydroxyethyl methacrylate, N,N-dimethylaminoethyl methacrylate; and styrene, vinyl acetate, silicone macromonomers, fluorine-based monomers, alkoxysilane unsaturated monomers, etc.

[0056] In addition, when the organic pigment composition of the present embodiment includes a surfactant, the surfactant serves to uniformly disperse and dissolve the composition in the solution. For the surfactant, as long as it is a surfactant that is not irritating to the skin and can be stably and uniformly dispersed in water and in alcohol, there is no particular restriction, but it is preferred to use a surfactant that does not have a bactericidal effect. The reason is that when the organic pigment composition is acted on a microorganism, the living cells of the microorganism may be inactivated or killed before sufficient dyeing. As a surfactant that does not have a bactericidal effect, anionic surfactants, amphoteric surfactants, and nonionic surfactants can be listed. As examples of anionic surfactants, carboxylates, sulfonates, and sulfates can be listed. As examples of amphoteric surfactants, amino acid-type or betaine-type carboxylates can be listed. As examples of nonionic surfactants, glycerol fatty acid esters, sorbitan fatty acid esters, sucrose fatty acid esters, polyoxyethylene alkyl ethers, polyoxyethylene alkylphenyl ethers, polyoxyethylene polyoxypropylene glycols, etc. can be listed. In addition, the HLB value of the surfactant used in the present embodiment is preferably 8 or more, more preferably 8 to 19. When the HLB value of the surfactant is 8 or more, the surfactant is easily dispersed or dissolved in higher alcohols, purified water, etc. The HLB value is an index representing the ratio of the relative affinity of the two liquids in an oil-water system. Generally, a surfactant with a large HLB value has a high affinity for water. It should be noted that the HLB value in this specification is a value calculated using the Griffin method.

[0057] Preparation of organic pigment compositions

[0058] The method for preparing the organic dye composition of the present embodiment is not particularly limited, and can be prepared, for example, by adding an organic dye (A) and an alcohol (B) to a predetermined amount of water (C) and stirring the mixture.

[0059] ·Application of organic pigment composition

[0060] The organic pigment composition of the present embodiment can make the visualization of microorganisms, therefore can be used for purposes such as the detection of microorganisms, the confirmation of disinfection effect.Therefore, it is preferably used as the spray that can spray and / or scatter in a wide range.By making the spray, thus can quickly and easily carry out the microbial detection in the object to be inspected.

[0061] As concrete object, for example can enumerate the storage place, door handle, washstand, bathtub, tile, production line, shoes, floor, toilet, table, infant product (nursing bottle, tableware, chair, toy etc.) of the sink, cooking utensils, cooking table, food in the kitchen, and the position or people's finger, body etc. that unspecified majority people contact in public places.Therefore, the organic pigment composition of present embodiment is preferably below 90 ° with respect to the contact angle of the stainless steel, artificial marble, quartz, resin, enamel, timber etc. that constitute these objects.By making the above-mentioned contact angle be set at below 90 °, thereby can improve the wettability of the organic pigment composition to the above-mentioned object.As a result, think: can make the above-mentioned organic pigment composition rest in the object to be tested, can more reliably carry out microbial detection.Preferred contact angle is below 80 °, further preferably below 70 °.

[0062] (Spray)

[0063] The spray of the present embodiment is not particularly limited as long as it contains the above-mentioned organic pigment composition. For example, the spray can be obtained by filling the organic pigment composition of the present embodiment in a spray container.

[0064] As the container for packing into the organic pigment composition, from the aspect of convenient carrying, a light-shielding container of 0.1 to 20 L that can be sealed is preferably used. As the material of the container, polyethylene terephthalate (PET), polypropylene (PP), polyethylene (PE), glass, etc. can be listed. In order to prevent the organic pigment contained in the organic pigment composition of the present invention from degrading by light decomposition, it is necessary to adopt a light-shielding container. In addition, as the container, a colored light-shielding container can be used, or the surface of the light-transmitting container can be covered with a light-shielding film or a thin film (aluminum foil, etc.).

[0065] In addition, in order to facilitate spraying and / or spreading, the spray container is preferably a container with a trigger nozzle.

[0066] According to the spray of this embodiment, the disinfection effect and the presence of microorganisms in a wide range can be easily checked in a short time.

[0067] (Application example)

[0068] The organic pigment composition and spray of the present embodiment are useful in various applications. For example, the organic pigment composition and spray of the present embodiment can be assembled into a system for visualizing the presence or absence of microorganisms, and the visualization system can be applied to cleaning of a house, for example.

[0069] Figure 1 It is a block diagram showing a brief configuration example of a microorganism visualization system (microorganism visualization method) using an organic pigment composition according to the present embodiment. In the microorganism visualization system, first, the organic pigment composition 1 according to the present embodiment is attached to an object 2 for detecting the presence or absence of microorganisms by spraying or the like. When microorganisms are present in the object, the organic pigment composition 1 according to the present embodiment reacts with the microorganisms to generate a hydrolyzate and discolor. The presence or absence of the discoloration is confirmed by visual recognition, thereby making it easy to investigate whether there are microorganisms in the object.

[0070] Figure 2 (A) is a block diagram showing another configuration example of a microorganism visualization system (microorganism visualization method) using the organic pigment composition involved in the present embodiment. In the microorganism visualization system, the organic pigment composition 1 involved in the present embodiment is attached to the object 2 for which the presence or absence of microorganisms is to be detected by spraying, etc., and then, a light source 3 emitting light with a wavelength of 400 nm or more and 550 nm or less is used to irradiate the object 2 with light. By irradiation with this light, when the object contains microorganisms, the hydrolyzate of the organic pigment (A) emits fluorescence under light irradiation, and the attachment site changes color, so that the presence site of the microorganism can be visually recognized.

[0071] In addition, if Figure 2 As shown in (B), the above-mentioned microorganism visualization system may further include a filter. In this case, in the above-mentioned microorganism visualization system, after the light source 3 irradiates the object 2 with light, the existence position of the microorganism is visually recognized through the filter 4. The filter 4 is preferably a filter that can filter out the wavelength of the light source 3. By using the filter 4 to remove the reflected light of the light source 3, etc., the visibility can be improved. In addition, the filter 4 can also be a filter with the function of filtering out ultraviolet light and / or blue light. In this way, light of wavelengths that are harmful to the eyes can be filtered out to protect the eyes, and the visibility can be improved.

[0072] In addition, if Figure 3 As shown in the block diagram, the microorganism visualization system may be a system structure including a camera. By using the camera, the presence or absence of microorganisms can be confirmed in the captured image.

[0073] In this case, the system further includes: an imaging unit 5 for photographing the object 2; a signal processing unit 6 for processing the signal obtained from the imaging unit 5; a storage unit 9 for storing luminance information related to the microorganism; an image generating unit 7 for generating an image based on the signal; and a display unit 8 for displaying the generated image.

[0074] 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 on the microorganisms stored in the storage unit (microorganism determination unit 10 ).

[0075] The image generation unit 7 generates an image based on the processing result of the signal processing unit 6. At this time, based on the microorganism determination information, an image that emphasizes the area determined to contain microorganisms can be generated. Specifically, for the area determined to contain microorganisms, it is considered to change the color tone and / or contrast to be easy to recognize.

[0076] By displaying the image obtained in this way on the display unit 8, the location where the microorganisms exist can be easily identified.

[0077] In summary, the present embodiment also includes the following technical solutions (microorganism visualization method and microorganism visualization system) and the like.

[0078] (First Application Example)

[0079] A method for visualizing microorganisms, comprising attaching an organic pigment composition to an object, and irradiating the object with light having a wavelength of 400 nm to 550 nm using a light source.

[0080] The organic pigment composition comprises: an organic pigment (A) that changes color by hydrolysis and emits fluorescence by excitation light having a wavelength of 400 nm to 550 nm; an alcohol (B); and water (C).

[0081] The content of organic pigment (A) is 1 μmol / L or more,

[0082] The viscosity is 5 mPa·s or more and 45 mPa·s or less.

[0083] (Second application example)

[0084] According to the microorganism visualization method of the first application example, the object is observed through a filter after irradiation with light.

[0085] (Third Application Example)

[0086] A microorganism visualization system is a microorganism visualization system that allows an organic pigment composition to be attached to an object and allows visualization of microorganisms, wherein the organic pigment composition contains: an organic pigment (A) that changes color by hydrolysis and emits fluorescence by excitation light with a wavelength of 400 nm to 550 nm; an alcohol (B); and water (C),

[0087] The content of organic pigment (A) is 1 μmol / L or more,

[0088] The viscosity is 5 mPa·s or more and 45 mPa·s or less,

[0089] The microorganism visualization system comprises: a light source for irradiating light to the object; an imaging unit for photographing the object and obtaining first brightness information; a storage unit for storing second brightness information related to the microorganism; a signal processing unit for comparing the first brightness information with the second brightness information and determining the presence or absence of the microorganism; an image generating unit for generating an image based on a signal; and a display unit for displaying the generated image.

[0090] A microorganism visualization method uses the above microorganism visualization system.

[0091] This specification discloses the technical solutions of various implementations as described above, and its main technologies are summarized as follows.

[0092] The organic pigment composition involved in the first technical solution of the present invention comprises: an organic pigment (A) that changes color by hydrolysis and emits fluorescence by excitation light with a wavelength of not less than 400 nm and not more than 550 nm; an alcohol (B); and water (C), wherein the content of the organic pigment (A) is not less than 1 μmol / L and the viscosity is not less than 5 mPa·s and not more than 45 mPa·s.

[0093] The organic dye composition according to the second invention is the organic dye composition according to the first invention, wherein the contact angle with at least one selected from the group consisting of stainless steel, artificial marble, quartz, resin, and enamel is 90° or less.

[0094] The organic dye composition according to the third invention is the organic dye composition according to the first and second inventions, wherein the organic dye (A) is at least one selected from the compounds represented by the above formula (1) to formula (5).

[0095] The organic dye composition according to a fourth aspect is the organic dye composition according to any one of the first to third aspects, wherein the alcohol (B) contains an alcohol having a boiling point of 180° C. or higher.

[0096] The organic pigment composition according to the fifth aspect is the organic pigment composition according to the fourth aspect, wherein the alcohol is at least one selected from glycerin and propylene glycol.

[0097] The organic dye composition according to the sixth invention is the organic dye composition according to the fourth and fifth inventions, wherein the content of the alcohol (B) is 50% by mass or more based on the entire organic dye composition.

[0098] A spray according to a seventh aspect of the present invention contains the organic dye composition according to any one of the first to sixth aspects.

[0099] The microorganism visualization method involved in the eighth technical solution of the present invention comprises: attaching the organic pigment composition of any one of the first to sixth technical solutions to an object; and irradiating the object with light having a wavelength of greater than 400nm and less than 550nm using a light source.

[0100] A microorganism visualization method according to a ninth aspect of the present invention is the microorganism visualization method according to the eighth aspect, comprising the step of observing the object through a filter after irradiating the light.

[0101] A microorganism visualization system according to a tenth aspect of the present invention is a microorganism visualization system that allows the organic pigment composition of any one of the first to sixth aspects to be attached to an object and visualizes the microorganisms, the microorganism visualization system comprising:

[0102] A light source irradiates light to the object; an imaging unit photographs the object and obtains first brightness information; a storage unit stores second brightness information related to the microorganism; a signal processing unit compares the first brightness information and the second brightness information and determines the presence or absence of the microorganism; an image generating unit generates an image based on a signal; and a display unit displays the generated image.

[0103] Hereinafter, the present invention will be described in more detail with reference to Examples; however, the scope of the present invention is not limited to these Examples.

[0104] Example

[0105] <Test Example 1>

[0106] (Preparation of organic pigment composition)

[0107] As an organic pigment (A), a DMSO solution of an organic pigment shown in the above formula (4) (excitation wavelength: 530 nm, pigment stock solution concentration: 0.03 wt % (1 mmol / L in DMSO) was used, as an alcohol (B), glycerol (boiling point: 290° C.) was used, and as water (C), pure water obtained from a Merck water manufacturing device "milliQ" was used, and each component was mixed and stirred according to the amount (mass %) shown in Table 1, thereby preparing the organic pigment compositions of Examples 1-1 to 1-5 and Comparative Examples 1-1 to 1-6.

[0108] (Evaluation method)

[0109] (1) Fluorescence emission when exposed to light

[0110] Bacterial solution (Escherichia coli, 10 6 cfu / mL) 100 μL. Then, the sample solution (organic pigment composition) of each embodiment and comparative example was placed in a spray bottle (φ39×147 mm, capacity 100 ml), and the above bacterial solution on the slide was sprayed (pressed once). Then, after leaving it for 15 minutes, the following fluorescence observation and color change observation were performed.

[0111] ·Fluorescence observation (visual visibility)

[0112] Regarding the fluorescence observation, the sprayed portion was irradiated with an LED lamp (output wavelength 530 nm, color: green) and visually observed through a red filter. The evaluation criteria were as follows:

[0113] ○: The luminescence of the solution can be clearly identified visually

[0114] △: The luminescence of the solution can be seen, but it is very weak

[0115] ×: The luminescence of the solution cannot be seen

[0116] Color change

[0117] The color change was observed visually and evaluated according to the following criteria:

[0118] ○: The color change of the solution can be clearly identified visually

[0119] △: The color change of the solution can be seen, but it is very weak

[0120] ×: The color change of the solution cannot be visually recognized, or no color change occurs

[0121] (2) Viscosity

[0122] The viscosity (mPa·s) of the sample solution (organic dye composition) of each Example and Comparative Example was measured using a rheometer (cone-plate viscometer) under the conditions of a shear rate of 1000 [1 / s] and 25°C.

[0123] (3) Contact angle

[0124] 100 μL of the sample solution (organic pigment composition) of each example and comparative example was dropped onto a substrate formed of polyethylene, polypropylene, and stainless steel, and the contact angle of the droplet on the substrate was measured using the droplet method (images were taken from a horizontal plane with a camera to measure the contact angle).

[0125] (4) Fixation of droplets on objects

[0126] The sample solution (organic pigment composition) was placed in a spray bottle (φ39×147mm, capacity 100ml) and sprayed (pressed once) onto polyethylene, polypropylene and stainless steel substrates. Then, the evaluation was performed by visual observation according to the following criteria. It should be noted that in each embodiment and comparative example, since it is impossible to exhaustively list all evaluation results based on the substrate material, the results are summarized as one and recorded.

[0127] ○: The contact angle with respect to the spray target substrate is 90° or less, and the spray solution can be fixed without being greatly scattered outside the spray area.

[0128] ×: The contact angle with respect to the spray target substrate is greater than 90°, and when the solution is sprayed, the droplets bounce back and roll off the spray target greatly, and scatter outside the spray area.

[0129] (5) Pigment stability

[0130] Whether the organic pigment (A) in the organic pigment composition undergoes natural decomposition (hydrolysis) has been confirmed, and the stability (durability) of the pigment has been confirmed. First, 1 mL of the sample solution (organic pigment composition) of each embodiment and comparative example was enclosed in a colorless and transparent microtube. Then, after being placed for 2 hours, the solution portion was irradiated with an LED lamp (output wavelength 530 nm, color: green), and visual observation was carried out through a red filter to confirm whether fluorescence was emitted at a level that could be visually observed. The evaluation criteria are as shown below:

[0131] ○: The organic pigment is not decomposed in the solution and is stable for more than 2 hours (no fluorescence can be seen after 2 hours)

[0132] ×: The organic pigment was decomposed over time in the solution, and fluorescence was visible after 2 hours.

[0133] The above results are summarized in Table 1.

[0134]

[0135] <Test Example 2>

[0136] (Preparation of organic pigment composition)

[0137] As an organic pigment (A), a DMSO solution of an organic pigment represented by the above formula (2) (excitation wavelength: 490 nm, pigment stock solution concentration: 0.1 wt% (1 mg / mL in DMSO) was used, as an alcohol (B), glycerol (boiling point: 290° C.) was used, and as water (C), pure water obtained by a Merck water manufacturing device “milliQ” was used, and each component was blended and stirred according to the amount (mass %) shown in Table 2, thereby preparing organic pigment compositions of Examples 2-1 to 2-5 and Comparative Examples 2-1 to 2-6.

[0138] Using each of the obtained organic dye compositions, the above-mentioned evaluation tests (1) to (5) were carried out in the same manner as in Test Example 1. The results are summarized in Table 2.

[0139]

[0140] <Test Example 3>

[0141] (Preparation of organic pigment composition)

[0142] As the organic pigment (A), a DMSO solution of the organic pigment shown in the above formula (4) (excitation wavelength: 530 nm, pigment stock solution concentration: 0.03 wt % (1 mmol / L in DMSO) was used, as the alcohol (B), glycerol (boiling point: 290° C.) was used, and as the water (C), pure water obtained by Merck's water manufacturing device "milliQ" was used, and each component was matched and stirred according to the amount (mass %) shown in Table 3, thereby preparing the organic pigment compositions of Examples 3-1 to 3-5 and Comparative Examples 3-1 to 3-6.

[0143] Using each of the obtained organic pigment compositions, Staphylococcus aureus (10 5 cfu / mL), the above-mentioned evaluation tests (1) to (5) were carried out in the same manner as in Test Example 1. The results are summarized in Table 3.

[0144]

[0145] <Test Example 4>

[0146] (Preparation of organic pigment composition)

[0147] As organic pigment (A), a DMSO solution of the organic pigment shown in the above formula (2) (excitation wavelength: 490nm, pigment stock solution concentration: 0.1wt% (1mg / mL in DMSO) was used, as alcohol (B), glycerol (boiling point: 290°C) was used, and as water (C), pure water obtained by Merck water manufacturing device "milliQ" was used, and each component was matched and stirred according to the amount (mass %) shown in Table 4, thereby preparing the organic pigment composition of Examples 4-1 to 4-5 and Comparative Examples 4-1 to 4-6.

[0148] Using each of the obtained organic pigment compositions, Staphylococcus aureus (10 5 cfu / mL), the above-mentioned evaluation tests (1) to (5) were carried out in the same manner as in Test Example 1. The results are summarized in Table 4.

[0149]

[0150] <Test Example 5>

[0151] (Preparation of organic pigment composition)

[0152] As the organic pigment (A), a DMSO solution of the organic pigment shown in the above formula (4) (excitation wavelength: 530 nm, pigment stock solution concentration: 0.03 wt % (1 mmol / Lin DMSO) was used, as the alcohol (B), 1,3-propylene glycol (boiling point: 213 ° C) was used, and as the water (C), pure water obtained by Merck's water manufacturing device "milliQ" was used, and each component was matched and stirred according to the amount (mass %) shown in Table 5, thereby preparing the organic pigment compositions of Examples 5-1 to 5-6 and Comparative Examples 5-1 to 5-5.

[0153] Using each of the obtained organic dye compositions, the above-mentioned evaluation tests (1) to (5) were carried out in the same manner as in Test Example 1. The results are summarized in Table 5.

[0154]

[0155] <Test Example 6>

[0156] (Preparation of organic pigment composition)

[0157] As an organic pigment (A), a DMSO solution of an organic pigment shown in the above formula (2) (excitation wavelength: 490 nm, pigment stock solution concentration: 0.1 wt % (1 mg / mL in DMSO) was used, as an alcohol (B), 1,3-propylene glycol (boiling point: 213° C.) was used, and as water (C), pure water obtained by a Merck water manufacturing device "milliQ" was used, and each component was matched and stirred according to the amount (mass %) shown in Table 6, thereby preparing the organic pigment compositions of Examples 6-1 to 6-6 and Comparative Examples 6-1 to 6-5.

[0158] Using each of the obtained organic dye compositions, the above-mentioned evaluation tests (1) to (5) were carried out in the same manner as in Test Example 1. The results are summarized in Table 6.

[0159]

[0160] <Test Example 7>

[0161] (Preparation of organic pigment composition)

[0162] As the organic pigment (A), a DMSO solution of the organic pigment shown in the above formula (4) (excitation wavelength: 530 nm, pigment stock solution concentration: 0.03 wt % (1 mmol / L in DMSO) was used, as the alcohol (B), 1,3-propylene glycol (boiling point: 213° C.) was used, and as the water (C), pure water obtained by Merck's water manufacturing device "milliQ" was used, and each component was matched and stirred according to the amount (mass %) shown in Table 7, thereby preparing the organic pigment compositions of Examples 7-1 to 7-6 and Comparative Examples 7-1 to 7-5.

[0163] Using each of the obtained organic pigment compositions, Staphylococcus aureus (10 5 cfu / mL), the above-mentioned evaluation tests (1) to (5) were carried out in the same manner as in Test Example 1. The results are summarized in Table 7.

[0164]

[0165] <Test Example 8>

[0166] (Preparation of organic pigment composition)

[0167] As an organic pigment (A), a DMSO solution of an organic pigment shown in the above formula (2) (excitation wavelength: 490 nm, pigment stock solution concentration: 0.1 wt % (1 mg / mL in DMSO) was used, as an alcohol (B), 1,3-propylene glycol (boiling point: 213° C.) was used, and as water (C), pure water obtained by a Merck water manufacturing device "milliQ" was used, and each component was mixed and stirred in an amount (mass %) as shown in Table 8, thereby preparing the organic pigment compositions of Examples 8-1 to 8-6 and Comparative Examples 8-1 to 8-5.

[0168] Using each of the obtained organic pigment compositions, Staphylococcus aureus (10 5 cfu / mL), the above-mentioned evaluation tests (1) to (5) were carried out in the same manner as in Test Example 1. The results are summarized in Table 8.

[0169]

[0170] <Inspection>

[0171] The results of Tables 1 to 8 show that the organic pigment composition of any embodiment can confirm the fluorescence and color change caused by the presence of Escherichia coli and Staphylococcus aureus, so it is considered to be effective for the detection of microorganisms. In addition, the fixation of the droplet on the object (spray object) formed by each material of polyethylene, polypropylene and stainless steel is also good, and the contact angle is also below 90 °. In addition, for the organic pigment in the organic pigment composition, sufficient storage stability (pigment stability) can also be confirmed.

[0172] As the organic pigment (A), the pigment represented by formula (4) can more clearly recognize the color change when irradiated with light in the detection of both Escherichia coli and Staphylococcus aureus than the pigment represented by formula (2). In addition, as the alcohol (B), glycerol can more clearly confirm the fluorescence and color change when irradiated with light than propylene glycol.

[0173] On the other hand, in the organic pigment composition of the comparative example (Comparative Example 1-1, 1-2 etc.) whose concentration of organic pigment (A) is too low, the detection of microorganisms cannot be carried out. In the comparative example (Comparative Example 1-3 etc.) that does not contain alcohol (B), the comparative example (Comparative Example 1-4, 1-5 etc.) whose viscosity is too low, the fixation of droplet in object is insufficient, or the result that the pigment stability is poor is presented. In addition, the organic pigment composition of the comparative example (Comparative Example 1-6 etc.) whose viscosity is too high of composition cannot be sprayed with atomizer because viscosity is too high.

[0174] This application is based on Japanese patent application No. 2022-121783 filed on July 29, 2022, and the contents are included in this application.

[0175] In order to express the present invention, the present invention has been appropriately and fully described above by referring to specific examples and the like through embodiments, but it should be recognized that those skilled in the art can easily change and / or improve the above embodiments. Therefore, as long as the modified embodiments or improved embodiments implemented by those skilled in the art do not deviate from the protection scope of the claims recorded in the claims, the modified embodiments or the improved embodiments can be interpreted as being included in the protection scope of the claims.

[0176] Industrial Applicability

[0177] According to the present invention, the disinfection effect and the presence of microorganisms in a wide range can be easily checked in a short time, so the present invention has wide industrial applicability in various technical fields such as the environment field, the medical field, the inspection field, and the sanitation field.

Claims

1. An organic pigment composition, characterized in that contain: The organic pigment (A) changes color by hydrolysis and emits fluorescence by excitation light having a wavelength of not less than 400 nm and not more than 550 nm; alcohol (B); and Water (C), where The content of the organic pigment (A) is 1 μmol / L or more, The viscosity is 5 mPa·s or more and 45 mPa·s or less.

2. The organic pigment composition according to claim 1, characterized in that The contact angle with respect to at least one selected from the group consisting of stainless steel, artificial marble, quartz, resin, and enamel is 90° or less.

3. The organic pigment composition according to claim 1, characterized in that The organic pigment (A) is at least one selected from the compounds represented by the following formula (1) to formula (5), 4. The organic pigment composition according to claim 1, characterized in that The alcohol (B) contains an alcohol having a boiling point of 180° C. or higher.

5. The organic pigment composition according to claim 4, characterized in that The alcohol is at least one selected from glycerol and propylene glycol.

6. The organic pigment composition according to claim 4, characterized in that The content of the alcohol (B) is 50% by mass or more based on the entire organic dye composition.

7. A spray, characterized in that contain: The organic pigment composition according to any one of claims 1 to 6.

8. A method for visualizing microorganisms, characterized in that: causing the organic pigment composition according to claim 1 to adhere to an object; and Whether or not the object has changed color is checked.

9. A method for visualizing microorganisms, characterized in that: causing the organic pigment composition according to claim 1 to adhere to an object; and The object is irradiated with light having a wavelength of not less than 400 nm and not more than 550 nm by a light source.

10. The microorganism visualization method according to claim 9, characterized in that: After irradiation with light, the object is observed through a filter.

11. A microbial visualization system, characterized in that A microorganism visualization system for making the organic pigment composition according to claim 1 adhere to an object and visualize the microorganisms, The microbial visualization system comprises: a light source for irradiating light to the object; An imaging unit, which captures the object and obtains first brightness information; a storage unit for storing second brightness information related to the microorganism; a signal processing unit, which compares the first brightness information and the second brightness information, and determines whether the microorganism exists; An image generating unit, generating an image according to the signal; as well as The display unit displays the generated image.

Images