WO2022209858A1 - 紫外線感知部材、紫外線感知キット - Google Patents
紫外線感知部材、紫外線感知キット Download PDFInfo
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- WO2022209858A1 WO2022209858A1 PCT/JP2022/011657 JP2022011657W WO2022209858A1 WO 2022209858 A1 WO2022209858 A1 WO 2022209858A1 JP 2022011657 W JP2022011657 W JP 2022011657W WO 2022209858 A1 WO2022209858 A1 WO 2022209858A1
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- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
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- AYNNSCRYTDRFCP-UHFFFAOYSA-N triazene Chemical compound NN=N AYNNSCRYTDRFCP-UHFFFAOYSA-N 0.000 description 1
- IMXXWWGWTMVZBZ-UHFFFAOYSA-N tribromo(tribromomethylsulfinyl)methane Chemical compound BrC(Br)(Br)S(=O)C(Br)(Br)Br IMXXWWGWTMVZBZ-UHFFFAOYSA-N 0.000 description 1
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- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ZZJNLOGMYQURDL-UHFFFAOYSA-M trifluoromethanesulfonate;tris(4-methylphenyl)sulfanium Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC(C)=CC=C1[S+](C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZZJNLOGMYQURDL-UHFFFAOYSA-M 0.000 description 1
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- 239000002023 wood Substances 0.000 description 1
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Images
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2/00—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor
- A61L2/26—Accessories or devices or components used for biocidal treatment
- A61L2/28—Devices for testing the effectiveness or completeness of sterilisation, e.g. indicators which change colour
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01J—MEASUREMENT OF INTENSITY, VELOCITY, SPECTRAL CONTENT, POLARISATION, PHASE OR PULSE CHARACTERISTICS OF INFRARED, VISIBLE OR ULTRAVIOLET LIGHT; COLORIMETRY; RADIATION PYROMETRY
- G01J1/00—Photometry, e.g. photographic exposure meter
- G01J1/48—Photometry, e.g. photographic exposure meter using chemical effects
- G01J1/50—Photometry, e.g. photographic exposure meter using chemical effects using change in colour of an indicator, e.g. actinometer
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N31/00—Investigating or analysing non-biological materials by the use of the chemical methods specified in the subgroup; Apparatus specially adapted for such methods
- G01N31/22—Investigating or analysing non-biological materials by the use of the chemical methods specified in the subgroup; Apparatus specially adapted for such methods using chemical indicators
- G01N31/226—Investigating or analysing non-biological materials by the use of the chemical methods specified in the subgroup; Apparatus specially adapted for such methods using chemical indicators for investigating the degree of sterilisation
Definitions
- the present invention relates to an ultraviolet sensing member and an ultraviolet sensing kit.
- Measurement of ultraviolet irradiation dose is carried out in various fields. Specific examples include measurement of the amount of ultraviolet irradiation to an object to be irradiated in the curing reaction of an ultraviolet curable resin, and measurement of the amount of ultraviolet irradiation to an object to be irradiated in ultraviolet sterilization of foods and the like.
- a method using "UV label” UV-H manufactured by NOF Giken Kogyo Co., Ltd.
- Patent Document 2 "UV scale” (manufactured by Fuji Film Co., Ltd. ) is disclosed.
- Non-Patent Document 1 reports the effect of inactivating the novel coronavirus using ultraviolet rays with a wavelength of 222 nm. More specifically, Non-Patent Document 1 reports that 99.7% inactivation of the new coronavirus is achieved by irradiating ultraviolet rays with a wavelength of 222 nm and an illuminance of 0.1 mW/cm 2 for 30 seconds. It is
- ultraviolet rays with a wavelength of 222 nm are effective in inactivating the new coronavirus, so for example, ultraviolet rays with a wavelength of 222 nm are applied to members that are touched by an unspecified number of people, such as doorknobs and touch panels.
- By irradiating it is possible to prevent infection with the new coronavirus.
- the present inventors used a conventionally known UV label and UV scale to measure whether the amount of light with a wavelength of 222 nm that inactivates the new coronavirus infection was irradiated. And on the UV scale, almost no change in color was observed, and the irradiation amount could not be determined. More specifically, even when the UV label and the UV scale were irradiated with ultraviolet light having a wavelength of 222 nm at an integrated illuminance of 3 mJ/cm 2 , almost no color change was observed.
- the first embodiment of the present invention aims to provide an ultraviolet sensing member that facilitates determination of whether or not the amount of irradiation that inactivates the new coronavirus has been applied.
- a second embodiment of the present invention provides an ultraviolet sensing member that makes it easy to determine whether or not the amount of radiation that inactivates the new coronavirus has been applied, and that can stably store the grounds for determination over a certain period of time. is the subject.
- Another object of the present invention is to provide an ultraviolet sensing kit.
- An ultraviolet sensing member comprising a sensitizer having a maximum absorption wavelength in the range of 200 to 230 nm, a photoactive agent, and a coloring agent.
- a sensitizer having a maximum absorption wavelength in the range of 200 to 230 nm
- a photoactive agent having a coloring agent.
- the sensitizer has a naphthalene structure.
- the photoactive agent has a halomethyl-s-triazine structure.
- X represents an oxygen atom, a sulfur atom or -NR19-
- R19 represents a hydrogen atom, an alkyl group or an aryl group.
- Each R independently represents a hydrogen atom or a monovalent substituent.
- An ultraviolet sensing member Using a KrCl excimer lamp as a light source, the ultraviolet sensing member is irradiated with light through a filter that substantially blocks light with a wavelength of 230 to 300 nm until the irradiation amount of light with a wavelength of 222 nm reaches 3 mJ/cm 2 , Using a spectrophotometer X-light (manufactured by X-Rite), the values of the yellow optical density, magenta optical density, and cyan optical density of the ultraviolet sensing member before light irradiation and the ultraviolet light sensing member after light irradiation.
- C1 is the cyan optical density value of the UV sensing member before light irradiation
- C2 is the cyan optical density value of the UV sensing member after 2 hours of light irradiation
- C2 is the UV sensing member after 24 hours of light irradiation.
- C3 is the cyan optical density value of C3
- Y1 is the yellow optical density value of the UV sensing member before light irradiation
- Y2 is the yellow optical density value of the UV sensing member after 2 hours of light irradiation, and 24 hours of light irradiation.
- Y3 is the yellow optical density value of the UV sensing member after irradiation
- M1 is the magenta optical density value of the UV sensing member before light irradiation
- M2 is the magenta optical density value of the UV sensing member after two hours of light irradiation.
- One is 0.20 or more, and is represented by the following formula (II) of the color that gives the maximum difference among the difference between C1 and C2, the difference between Y1 and Y2, and the difference between M1 and M2
- An ultraviolet sensing member having an optical density change rate of -50% or more and 50% or less.
- Optical density change rate (%) [(optical density after 24 hours of irradiation) - (optical density after 2 hours of irradiation)] / [(optical density after 2 hours of irradiation) - (optical density before irradiation)] x 100 ⁇ 6> UV sensing according to any one of ⁇ 1> to ⁇ 4>, wherein the difference between C1 and C2, the difference between Y1 and Y2, the difference between M1 and M2, and the optical density change rate satisfy the requirements of ⁇ 5>.
- An ultraviolet sensing kit comprising the ultraviolet sensing member according to any one of ⁇ 1> to ⁇ 7>.
- the UV sensing member includes the UV sensing member according to any one of ⁇ 1> to ⁇ 7>, and after irradiating the UV sensing member with light until the irradiation amount of light with a wavelength of 313 nm reaches 9 mJ/cm 2 , the spectrophotometer X-light (manufactured by X-Rite Co., Ltd.), the yellow optical density, magenta optical density, and cyan optical density of the ultraviolet sensing member before light irradiation and the ultraviolet sensing member after light irradiation are measured, respectively.
- C4 is the cyan optical density value of the ultraviolet sensing member before irradiation
- C5 is the cyan optical density value of the ultraviolet sensing member after two hours of light irradiation
- C5 is the yellow optical density value of the ultraviolet sensing member before light irradiation.
- Y4 is the yellow optical density value of the UV sensing member after 2 hours of light irradiation
- Y5 is the magenta optical density value of the UV sensing member before light irradiation
- M4 is the magenta optical density value of the UV sensing member after 2 hours of light irradiation.
- An ultraviolet sensing kit wherein the difference between C4 and C5, the difference between Y4 and Y5, and the difference between M4 and M5 are all 0.15 or less, where M5 is the optical density value.
- an ultraviolet sensing member that facilitates determination of whether or not the amount of irradiation that inactivates the novel coronavirus has been applied.
- an ultraviolet sensing member that can easily determine whether the amount of radiation that inactivates the new coronavirus has been irradiated and can stably store the basis for determination over a certain period of time.
- an ultraviolet sensing kit can be provided.
- a numerical range represented by "to” means a range including the numerical values before and after "to” as lower and upper limits.
- the upper limit or lower limit described in a certain numerical range may be replaced with the upper limit or lower limit of the numerical range described in other steps. good.
- the upper limit or lower limit described in a certain numerical range may be replaced with the values shown in the examples.
- the solid content means a component that forms a composition layer formed using the composition, and when the composition contains a solvent (for example, an organic solvent, water, etc.), the solvent is means all ingredients except
- a liquid component is also regarded as a solid content.
- ultraviolet light means light with a wavelength range of 10 to 400 nm.
- (meth)acryl means "at least one of acryl and methacryl”.
- the "boiling point” means the boiling point at standard atmospheric pressure.
- a first embodiment of the ultraviolet sensing member of the present invention comprises a sensitizer having a maximum absorption wavelength in the range of 200 to 230 nm, a photoactive agent, and a color former.
- the UV-sensing member preferably has a support and a UV-sensitive layer. It preferably contains an activator and a color former. Each material included in the ultraviolet sensing member (or the ultraviolet sensing layer) will be described in detail below.
- a first embodiment of the UV sensitive member comprises a color former.
- the ultraviolet sensitive member preferably includes an ultraviolet sensitive layer containing a coloring agent.
- a specific configuration of the ultraviolet sensing member will be described in detail later.
- the term "color former” refers to a compound that develops a color from a substantially colorless state (a colorless or weakly colored state) by the action of an acid, oxidation, light irradiation, or the like. Point.
- the type of color former is not particularly limited, and examples thereof include a color former that develops color upon oxidation, a color former that develops color by the action of acid, and a color former that develops color by action of light.
- a color former that develops color by oxidation or a color former that develops color by the action of acid is preferable, and a color former that develops color by the action of acid is more preferred.
- the coloring agent leuco dyes or photochromic dyes are preferable, and leuco dyes are more preferable.
- Known photochromic dyes include compounds that isomerize and develop color under the action of light, compounds that develop color due to the progress of ring-closing reaction under the action of light, and compounds that develop color due to the progress of ring-opening reaction under the action of light. and known photochromic dyes can be used.
- the photochromic dye those in which color development and decoloring reactions reversibly proceed with energy are preferred.
- the leuco dye is a compound that develops color when it is oxidized from a substantially colorless state (hereinafter also referred to as "oxidative coloring leuco dye"), or a compound that develops color from a substantially colorless state by the action of an acid. (hereinafter also referred to as "acid-color-forming leuco dye").
- leuco dyes examples include triarylmethanephthalide-based compounds, fluoran-based compounds, phenothiazine-based compounds, indolylphthalide-based compounds, azaindolylphthalide-based compounds, leuco auramine-based compounds, rhodamine lactam-based compounds, triarylmethanephthalide-based compounds, Examples include arylmethane-based compounds, diarylmethane-based compounds, triazene-based compounds, spiropyran-based compounds, thiazine compounds, and fluorene-based compounds. For details of the above compounds, reference can be made to the descriptions in US Pat.
- the coloring agents may be used singly or in combination of two or more.
- Oxidative Color-Forming Leuco Dye One embodiment of the oxidation color-forming leuco dye is preferably a compound having one or two hydrogen atoms that develops color by removing electrons.
- Such oxidative chromogenic leuco dyes include, for example, (a) aminotriarylmethane, (b) aminoxanthine, (c) aminothioxanthine, and (d) as described in US Pat. No. 3,445,234.
- aminoarylmethanes are preferred, and aminotriarylmethanes are more preferred.
- Aminotriarylmethane is preferably a compound represented by the following formula (L) or an acid salt thereof.
- Ar 1 represents a phenyl group with R 1 R 2 N-substituents para to the bond to the methane carbon atom specified in formula (A1).
- Ar 2 is a phenyl group having an R 1 R 2 N-substituent para to the bond to the methane carbon atom specified in formula (A1), or a phenyl group specified in formula (A2) ortho-position to the methane carbon atom, an alkyl group (preferably an alkyl group having 1 to 4 carbon atoms), an alkoxy group (preferably an alkoxy group having 1 to 4 carbon atoms), a fluorine atom, a chlorine atom, and, It represents a phenyl group having a substituent selected from the group consisting of bromine atoms.
- R 1 and R 2 each independently represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a 2-hydroxyethyl group, a 2-cyanoethyl group or a benzyl group.
- Ar 3 represents the same group as at least one of Ar 1 and Ar 2 , or represents a group different from Ar 1 and Ar 2 .
- Ar 3 represents a group different from Ar 1 and Ar 2
- Ar 3 is (B1) a lower alkyl group (preferably an alkyl group having 1 to 4 carbon atoms), a lower alkoxy group (preferably 4 alkoxy groups), chlorine atom, diphenylamino group, cyano group, nitro group, hydroxy group, fluorine atom, bromine atom, alkylthio group, arylthio group, thioester group, alkylsulfonic acid group, arylsulfonic acid group, sulfonic acid a phenyl group optionally substituted with a substituent selected from the group consisting of a group consisting of a sulfonamide group, an alkylamide group, and an arylamide group; (B2) an amine group, a di-lower alkylamino group, and an alkylamino group; a naphthyl group optionally substituted with a substituent selected from the group consisting of (B3)
- R 1 and R 2 are each independently preferably a hydrogen atom or alkyl having 1 to 4 carbon atoms.
- Ar 1 , Ar 2 and Ar 3 are all R 1 R 2 N para to the bond to the methane carbon atom specified in formula (A1). It preferably represents a phenyl group having a -substituent, and more preferably the same group.
- oxidation chromogenic leuco dyes include tris(4-dimethylaminophenyl)methane, tris(4-diethylaminophenyl)methane, bis(4-diethylaminophenyl)-(4-diethylamino-2-methylphenyl)methane, Bis(4-diethylamino-2-methylphenyl)-(4-diethylaminophenyl)methane, bis(1-ethyl-2-methylindol-3-yl)-phenylmethane, 2-N-(3-trifluoromethylphenyl )-N-ethylamino-6-diethylamino-9-(2-methoxycarbonylphenyl)xanthene, 2-(2-chlorophenyl)amino-6-dibutylamino-9-(2-methoxycarbonylphenyl)xanthene, 2-di Benzylamino-6
- Acid-color-forming leuco dye As one aspect of the acid-color-forming leuco dye, it is preferably a compound that develops color by donating electrons or accepting protons such as acids. Specific examples include compounds having partial skeletons such as lactones, lactams, sultones, spiropyrans, esters, and amides, and these partial skeletons are ring-opened or cleaved upon contact with acids or protons.
- Leuco dyes that develop color under the action of acid include, for example, 3,3-bis(2-methyl-1-octyl-3-indolyl)phthalide and 6′-(dibutylamino)-2′.
- a spirolactone compound represented by the following formula (I) is preferable as the acid color former of the present invention from the viewpoint of color development.
- X represents an oxygen atom, a sulfur atom or -NR19-
- R19 represents a hydrogen atom, an alkyl group or an aryl group.
- Each R independently represents a hydrogen atom or a monovalent substituent.
- the alkyl group represented by R19 is preferably an alkyl group having 1 to 30 carbon atoms, more preferably an alkyl group having 1 to 15 carbon atoms, and even more preferably an alkyl group having 1 to 10 carbon atoms.
- the alkyl group may be linear, branched, or have a cyclic structure.
- alkyl groups methyl, ethyl, propyl or butyl groups are preferred.
- the above alkyl group may have a substituent.
- substituents include alkoxy groups, aryloxy groups, amino groups, alkylthio groups, arylthio groups, halogen atoms, carboxy groups, carboxylate groups, sulfo groups, sulfonate groups, alkyloxycarbonyl groups, aryloxycarbonyl groups, and Groups in which these are combined, and the like are included.
- the aryl group represented by R19 is preferably an aryl group having 6 to 30 carbon atoms, more preferably an aryl group having 6 to 20 carbon atoms, and even more preferably an aryl group having 6 to 12 carbon atoms.
- the aryl group may have a substituent. Examples of substituents include alkyl groups, alkoxy groups, aryloxy groups, amino groups, alkylthio groups, arylthio groups, halogen atoms, carboxy groups, carboxylate groups, sulfo groups, sulfonate groups, alkyloxycarbonyl groups, and aryloxycarbonyl groups. , and groups obtained by combining these.
- phenyl group, naphthyl group, p-tolyl group, p-chlorophenyl group, p-fluorophenyl group, p-methoxyphenyl group, p-dimethylaminophenyl group, p-methylthiophenyl group, p- A phenylthiophenyl group and the like can be mentioned.
- aryl groups phenyl, p-methoxyphenyl, p-dimethylaminophenyl or naphthyl groups are preferred.
- Examples of monovalent substituents represented by R include alkyl groups, alkoxy groups, aryl groups, aryloxy groups, amino groups, alkylthio groups, arylthio groups, halogen atoms, carboxyl groups, carboxylate groups, sulfo groups, sulfonate groups, An alkyloxycarbonyl group and an aryloxycarbonyl group are preferred.
- X is preferably an oxygen atom from the viewpoint of color development efficiency. Specific examples of compounds that function as acid color formers are shown below, but the present invention is not limited thereto.
- the molecular weight of the compound represented by general formula (I) is not particularly limited, it is preferably 300 or more, more preferably 350 or more. Although the upper limit is not particularly limited, it is preferably 2000 or less, more preferably 1000 or less.
- the content of the coloring agent in the ultraviolet-sensitive layer is not particularly limited, but it is easier to determine whether the amount of irradiation that inactivates the new coronavirus is irradiated (hereinafter simply referred to as "the effect of the present invention It is also referred to as "a point where the UV-sensitive layer is more excellent.”), it is preferably 0.500 g/m 2 or less, more preferably 0.300 g/m 2 or less, and 0.140 g/m 2 or less per unit area (m 2 ) of the ultraviolet sensitive layer. More preferred. Although the lower limit is not particularly limited, it is preferably 0.010 g/m 2 or more, more preferably 0.030 g/m 2 or more.
- the content of the color former in the ultraviolet-sensitive layer By setting the content of the color former in the ultraviolet-sensitive layer within the above range, excessive absorption of 222 nm by the color former is suppressed, so the minimum amount of the color former necessary for the color-developing reaction can be obtained, which will be described later. It is presumed that the optical density difference in the second embodiment can be made 0.20 or more.
- the content of the coloring agent is obtained by cutting out an area having a large amount of the ultraviolet sensitive layer from the ultraviolet sensitive member, immersing the ultraviolet sensitive layer in acetonitrile for two days, and then analyzing the obtained solvent by liquid chromatography. can be calculated. Acetonitrile should not volatilize during the immersion.
- a calibration curve for the content of the color former to be detected may be prepared before the liquid chromatography measurement.
- the measurement conditions for liquid chromatography are as follows. Apparatus: Nexera manufactured by Shimadzu Corporation Column: Capcell pak C18 UG-120 Eluent: water/acetonitrile Oven: 40°C Injection: 5 ⁇ L Detection: Maximum absorption wavelength of color former to be detected Flow rate: 0.2 mL/min
- the content of the coloring agent in the ultraviolet sensitive layer is preferably 0.1 to 20 parts by weight, more preferably 0.3 to 10 parts by weight, more preferably 0.5 to 0.5 parts by weight, based on 100 parts by weight of the ultraviolet sensitive layer. 3 is more preferred.
- a first embodiment of the UV sensitive member comprises a photoactive agent.
- the ultraviolet sensitive layer included in the ultraviolet sensitive member contains a photoactive agent.
- the photoactive agent is not particularly limited as long as the photoactive agent itself absorbs light or is a compound that is activated by receiving electrons, holes, or energy from another compound that has absorbed light.
- the photoactive agent activated by light preferably acts on the coloring agent to develop color, and is preferably a compound activated by ultraviolet rays.
- the photoactive agent is preferably one or more of a photooxidizing agent and a photoacid generator.
- the photoactive agent preferably contains a photooxidizing agent.
- the agent comprises a photoacid generator.
- the mass ratio of the content of the photoactive agent to the content of the color former is preferably more than 1.00, more preferably 3.00, in terms of more excellent effects of the present invention. The above is more preferable. Although the upper limit is not particularly limited, it is preferably 40.00 or less, more preferably 30.00 or less, still more preferably 25.00 or less, particularly preferably 20.00 or less, and most preferably 10.00 or less.
- the mass ratio of the content of the photoactive agent to the content of the coloring agent can be measured by liquid chromatography after extraction with methanol in the same manner as the content of the coloring agent described above.
- the photoactive agent is detected at the maximum absorption wavelength of the photoactive agent to be detected, and the coloring agent is detected at the maximum absorption wavelength of the coloring agent to be detected, and the mass ratio is determined.
- the photo-oxidizing agent is a compound that can be activated by ultraviolet rays to generate radicals and/or extract the hydrogen atoms of the coloring agent to color the coloring agent.
- the photo-oxidizing agent is preferably one or more of radical generators and organic halogen compounds.
- a mode in which a radical generator and an organic halogen compound are used in combination as a photoacid generator is also preferred.
- the ratio of the content of the radical generator to the organic halogen compound is such that the gradation of the color-developing portion is more excellent. , preferably 0.1 to 10, more preferably 0.5 to 5.
- the radical generator is not particularly limited as long as it is a compound that is activated by ultraviolet rays to generate radicals.
- a hydrogen abstraction type radical generator is preferred.
- the hydrogen abstraction type radical generator has the effect of abstracting hydrogen atoms from the color former to promote oxidation of the color former.
- Radical generators include, for example, the azide polymer described on page 55 of the 1968 Spring Research Presentation Meeting of the Photographic Society of Japan; 2-azidobenzoxazole, benzoylazide, and 2- Azide compounds such as azidobenzimidazole; 3′-ethyl-1-methoxy-2-pyridothiacyanine perchlorate and 1-methoxy-2-methylpyridinium p-toluene as described in US Pat. No.
- lophine dimer compounds such as 2,4,5-triarylimidazole dimers described in JP-B-62-039728; benzophenones; p-aminophenyl ketones; polynuclear quinones; Among them, one or more selected from lophine dimers and benzophenones are preferable, and lophine dimers are more preferable.
- Rophine dimers include, for example, hexaarylbiimidazole compounds. As the hexaarylbiimidazole-based compound, the compounds described in paragraph 0047 of International Publication No. 2016/017701 can be considered, and the contents thereof are incorporated herein.
- 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenyl-1,2'-biimidazole is preferred.
- 2,2′-bis(2-chlorophenyl)-4,4′,5,5′-tetraphenyl-1,2′-biimidazole include “B-IMD” (manufactured by Kurogane Kasei Co., Ltd.), And "B-CIM” (manufactured by Hodogaya Chemical Industry Co., Ltd.) can be used.
- lophine dimers compounds represented by the following general formula (1) are also preferred.
- A, B, and D are each independently a carbocyclic or heteroaryl group that is unsubstituted or substituted with a substituent that does not inhibit dissociation of the dimer to imidazolyl group or oxidation of the color former; represents B and D are each independently preferably unsubstituted or have 1 to 3 substituents, and A is unsubstituted or has 1 to 4 substituents is preferred.
- Knowledge known as lophine dimers and the like can be used for the compounds represented by the general formula (1) and methods for producing them. See, for example, US Pat. No. 3,552,973 at column 4, line 22 and column 6, line 3, the contents of which are incorporated herein.
- One type of radical generator may be used alone, or two or more types may be mixed and used.
- the organic halogen compound can accelerate the oxidation of the coloring agent.
- a compound in which the number of halogen atoms in the molecule is 3 or more is preferable because the gradation of the color-developing portion is more excellent.
- the upper limit of the number of halogen atoms is preferably 9 or less.
- the organic halogen compounds are compounds other than lophine dimers and benzophenones.
- An organic halogen compound may be used individually by 1 type, and may be used in mixture of 2 or more types. Examples of organic halogen compounds include compounds represented by the following general formulas (2) to (7).
- P 0 represents a hydrogen atom, a halogen atom, an optionally substituted alkyl group, or an optionally substituted aryl group.
- Each X independently represents a halogen atom.
- Halogen atoms represented by P 0 and X include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, preferably a chlorine atom or a bromine atom.
- substituents that the alkyl group and aryl group represented by P 0 may have include a hydroxy group, a halogen atom, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, an acetyl group, and , an alkoxy group having 1 to 6 carbon atoms, and the like.
- Examples of compounds represented by the general formula (2) include trichloromethane, tribromomethane, carbon tetrachloride, carbon tetrabromide, p-nitrobenzotribromide, bromotrichloromethane, pensitrichloride, hexabromoethane, iodoform, 1,1,1-tribromo-2-methyl-2-propanol, 1,1,2,2-tetrabromoethane, 2,2,2-tribromoethanol, and 1,1,1-trichloro- 2-methyl-2-propanol can be mentioned.
- R represents a substituent.
- x represents an integer of 0 to 5;
- substituents represented by R include a nitro group, a halogen atom, an alkyl group having 1 to 3 carbon atoms, a haloalkyl group having 1 to 3 carbon atoms, an acetyl group, a haloacetyl group, and a group having 1 to 3 carbon atoms.
- An alkoxy group is mentioned.
- R may mutually be same or different.
- Examples of compounds represented by general formula (3) include o-nitro- ⁇ , ⁇ , ⁇ -tribromoacetophenone, m-nitro- ⁇ , ⁇ , ⁇ -tribromoacetophenone, p-nitro- ⁇ , ⁇ , ⁇ -tribromoacetophenone, ⁇ , ⁇ , ⁇ -tribromoacetophenone, and ⁇ , ⁇ , ⁇ -tribromo-3,4-cycloacetophenone.
- R 1 represents an optionally substituted alkyl group or an optionally substituted aryl group.
- X 1 represents a halogen atom.
- the alkyl group represented by R 1 is preferably an alkyl group having 1 to 20 carbon atoms, more preferably an alkyl group having 1 to 10 carbon atoms, and even more preferably an alkyl group having 1 to 6 carbon atoms.
- the aryl group represented by R 1 is preferably an aryl group having 6 to 20 carbon atoms, more preferably an aryl group having 6 to 14 carbon atoms, and even more preferably an aryl group having 6 to 10 carbon atoms.
- substituents that the alkyl group and aryl group represented by R 1 may have include a nitro group, a halogen atom, an alkyl group having 1 to 3 carbon atoms, a haloalkyl group having 1 to 3 carbon atoms, an acetyl group, and a haloacetyl. and alkoxy groups having 1 to 3 carbon atoms.
- the halogen atom represented by X 1 includes a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, preferably a chlorine atom, a bromine atom or an iodine atom, more preferably a chlorine atom or a bromine atom.
- Examples of compounds represented by general formula (4) include 2,4-dinitrobenzenesulfonyl chloride, o-nitrobenzenesulfonyl chloride, m-nitrobenzenesulfonyl chloride, 3,3′-diphenylsulfonedisulfonyl chloride, and ethanesulfonyl chloride.
- R 2 represents an optionally substituted alkyl group or an optionally substituted aryl group.
- X2 represents a halogen atom.
- the alkyl group optionally having substituent(s) and the aryl group optionally having substituent(s) represented by R 2 are the same as R 1 in general formula (4), and the preferred embodiments are also the same. be.
- the halogen atom represented by X2 includes a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, preferably a chlorine atom, a bromine atom or an iodine atom, more preferably a chlorine atom or a bromine atom.
- Examples of compounds represented by general formula (5) include 2,4-dinitrobenzenesulfenyl chloride and o-nitrobenzenesulfenyl chloride.
- R 3 represents an optionally substituted aryl group or an optionally substituted heteroaryl group.
- L 1 represents -SO- or SO 2 -.
- X 3 , X 4 and X 5 each independently represent a hydrogen atom or a halogen atom. However, not all of X 3 , X 4 and X 5 are hydrogen atoms.
- the aryl group represented by R 3 is preferably an aryl group having 6 to 20 carbon atoms, more preferably an aryl group having 6 to 14 carbon atoms, and even more preferably an aryl group having 6 to 10 carbon atoms.
- the heteroaryl group represented by R 3 is preferably a heteroaryl group having 4 to 20 carbon atoms, more preferably a heteroaryl group having 4 to 13 carbon atoms, and even more preferably a heteroaryl group having 4 to 9 carbon atoms.
- substituents that the aryl group and heteroaryl group represented by R 3 may have include a nitro group, a halogen atom, an alkyl group having 1 to 3 carbon atoms, a haloalkyl group having 1 to 3 carbon atoms, an acetyl group, A haloacetyl group and an alkoxy group having 1 to 3 carbon atoms can be mentioned.
- the halogen atoms represented by X 3 , X 4 and X 5 include, for example, a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, preferably a chlorine atom, a bromine atom or an iodine atom. , a chlorine atom or a bromine atom are more preferred.
- Examples of compounds represented by general formula (6) include hexabromodimethylsulfoxide, pentabromodimethylsulfoxide, hexabromodimethylsulfone, trichloromethylphenylsulfone, tribromomethylphenylsulfone (BMPS), trichloro-p- Chlorophenylsulfone, Tribromomethyl-p-nitrophenylsulfone, 2-Trichloromethylbenzothiazolesulfone, 4,6-Cymethylpyrimidine-2-tribromomethylsulfone, Tetrabromodimethylsulfone, 2,4-Dichlorophenyl-trichloromethylsulfone sulfone, 2-methyl-4-chlorophenyltrichloromethylsulfone, 2,5-dimethyl-4-chlorophenyltrichloromethylsulfone, 2,4-dichlorophenyltrimethylsulfone, and tri-p-to
- R4 represents an optionally substituted heteroaryl group.
- X 6 , X 7 and X 8 each independently represent a hydrogen atom or a halogen atom. However, not all of X 6 , X 7 and X 8 are hydrogen atoms.
- the heteroaryl group represented by R 4 is preferably a heteroaryl group having 4 to 20 carbon atoms, more preferably a heteroaryl group having 4 to 13 carbon atoms, and still more preferably a heteroaryl group having 4 to 9 carbon atoms.
- substituents that the heteroaryl group represented by R 4 may have include a nitro group, a halogen atom, an alkyl group having 1 to 3 carbon atoms, a haloalkyl group having 1 to 3 carbon atoms, an acetyl group, a haloacetyl group, An alkoxy group having 1 to 3 carbon atoms can be mentioned.
- the halogen atoms represented by X 6 , X 7 and X 8 include, for example, a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, preferably a chlorine atom, a bromine atom or an iodine atom. , a chlorine atom or a bromine atom are more preferred.
- Examples of the compound represented by the general formula (7) include tribromoquinaldine, 2-tribromomethyl-4-methylquinoline, 4-tribromomethylpyrimidine, 4-phenyl-6-tribromomethylpyrimidine, 2 -trichloromethyl-6-nitrobenzothiazole, 1-phenyl-3-trichloromethylpyrazole, 2,5-ditribromomethyl-3,4-dibromothiophene, and 2-trichloromethyl-3-(p-butoxystyryl) -1,3,4-oxadiazoles.
- Halomethyl-s-triazine compounds are also preferred as compounds represented by general formula (7).
- Examples include 2,4-bis(trichloromethyl)-6-p-methoxystyryl-s-triazine, 2,6-bis(trichloromethyl)-4-(3,4-methylenedioxyphenyl)-1 ,3,5-triazine, 2,6-bis(trichloromethyl)-4-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(1-p -dimethylaminophenyl-1,3-butadienyl)-s-triazine, 2-trichloromethyl-4-amino-6-p-methoxystyryl-s-triazine, 2-(naphth-1-yl)-4,6- Bis-trichloromethyl-s-triazine, 2-(4-methoxy-naphth-1-yl)-4,6-bis-trichloromethyl-s-triazine, 2-(4-ethoxy-
- the organic halogen compound the compound represented by the general formula (3), the compound represented by the general formula (6), or the compound represented by the general formula (7) is preferable, and the effect of the present invention is obtained. is more excellent, the compound represented by the general formula (7) is more preferable, and the halomethyl-s-triazine compound is particularly preferable.
- the photoactive agent has a halomethyl-s-triazine structure.
- the organic halogen compounds may be used singly or in combination of two or more.
- the photo-acid generator is preferably a compound that is cleaved by ultraviolet rays to generate an acid, and that can color the color former by the action of the acid.
- the photoacid generator include nonionic photoacid generators and ionic photoacid generators, and nonionic photoacid generators are preferred because the effects of the present invention are more excellent.
- nonionic photoacid generators include organic halogen compounds and oxime compounds. Among them, organic halogen compounds are preferred in that the effects of the present invention are more excellent, and compounds represented by the above-described general formula (7). is more preferred.
- the organic halogen compound a compound having 3 or more halogen atoms in the molecule is preferable because the gradation of the color-developing portion is more excellent.
- the upper limit of the number of halogen atoms is preferably 9 or less.
- An organic halogen compound may be used individually by 1 type, and may be used in mixture of 2 or more types. Specific examples of the organic halogen compound include the same organic halogen compounds mentioned as the photo-oxidizing agent in the upper section.
- Ionic photoacid generators include diazonium salts, iodonium salts, and sulfonium salts, with iodonium salts or sulfonium salts being preferred.
- Examples of the ionic photoacid color former include compounds described in JP-A-62-161860, JP-A-61-067034, and JP-A-62-050382. is incorporated herein.
- the photoacid generator is not particularly limited as long as it is a compound that generates an acid upon exposure to light. Photoacid generators that generate inorganic acids such as hydrogen halide (e.g., hydrochloric acid), sulfuric acid, and nitric acid can be used.
- a photo-acid generator that generates an inorganic acid is preferable, and a photo-acid generator that generates a hydrogen halide is more preferable, from the viewpoint that the effects of the present invention are more excellent.
- photoacid generators include triarylsulfonium hexafluorophosphate, triarylsulfonium arsenate, triarylsulfonium antimonate, diaryliodonium hexafluorophosphate, diaryliodonium arsenate, diaryliodonium antimonate, and dialkylphenacyl.
- a first embodiment of the UV sensitive member contains a sensitizer having a maximum absorption wavelength in the range of 200-230 nm.
- the sensitizer of the present invention absorbs light having a wavelength of 200 to 230 nm to be excited, and has the function of generating radicals or acids from the photoactive agent by giving electrons, holes, or energy from the excited state to the photoactive agent. have.
- the sensitizer of the present invention has a maximum absorption wavelength in the wavelength range of 200 to 230 nm from the viewpoint of detecting with high sensitivity the irradiation amount of light with a wavelength of 222 nm that inactivates the novel coronavirus infection.
- the sensitizer of the present invention is a compound that generates a radical or acid from a photoactivator by donating electrons from an excited state to the photoactivator (hereinafter referred to as an electron-donating sensitizer), the following formula ( It is preferable that the change in free energy represented by III) is negative from the viewpoint of efficient electron transfer from the sensitizer to the photoactive agent.
- the sensitizer of the present invention various compounds can be used as long as they absorb light with a wavelength of 200 to 230 nm, but condensed aromatic compounds are preferable from the viewpoint of making ⁇ G negative, and naphthalenes.
- anthracenes, pyrenes, carbazoles, dibenzofurans, dibenzothiophenes, and the like can be preferably used.
- naphthalenes are preferable because they have a large absorption coefficient at a wavelength of 200 to 230 nm. That is, the sensitizer preferably has a naphthalene structure.
- One type of sensitizer may be used alone, or two or more types may be mixed and used.
- the amount of the sensitizer of the present invention to be added is preferably 0.01 to 50 parts by mass, more preferably 0.1 to 20 parts by mass, per 100 parts by mass of the UV-sensitive layer.
- the molar ratio of the sensitizer of the present invention to the photo-oxidant of the present invention is preferably 0.1 or more and 50 or less, more preferably 1.0 or more and 30 or less.
- the molar ratio of the sensitizer of the present invention to the color former of the present invention is preferably 0.1 or more, and 1 or more, because the sensitizer of the present invention can efficiently absorb light with a wavelength of 200 to 230 nm. more preferred.
- 50 or less is realistic, 30 or less is preferable, 10 or less is more preferable, and 5 or less is even more preferable.
- the ultraviolet sensing member will be described in detail below with specific aspects.
- an ultraviolet sensitive layer containing a sensitizer having a maximum absorption wavelength in the range of 200 to 230 nm, a photoactive agent, a coloring agent, and a binder resin is provided. It is an ultraviolet sensing member provided.
- FIG. 1 is a schematic cross-sectional view of an example of a first embodiment of an ultraviolet sensing member.
- the ultraviolet sensing member 10 includes a support 12, and a sensitizer having a maximum absorption wavelength in the range of 200 to 230 nm, a photoactive agent, a color former, and a binder resin disposed on one surface of the support 12. and a UV-sensitive layer 14 comprising:
- a colored portion (not shown) is formed with a coloring density corresponding to the amount of ultraviolet irradiation.
- FIG. 1 shows a mode in which the ultraviolet sensing member is sheet-shaped, but the present invention is not limited to this mode.
- the ultraviolet sensitive member 10 may have the ultraviolet sensitive layer 14 and may not have the support 12 .
- the ultraviolet sensing member 10 shown in FIG. 1 has a two-layer structure of the support 12 and the ultraviolet sensing layer 14, it is not limited to this aspect, and as described later, other layers than the support 12 and the ultraviolet sensing layer 14 are formed. Other layers (eg, reflective layer, gloss layer, filter layer, etc.) may be provided.
- the UV-irradiated region changes depending on the UV dose (for example, integrated illuminance).
- a colored portion is formed with the color-developed density. Developing a color with a color density corresponding to the amount of ultraviolet irradiation means that the colored image has gradation according to the amount of ultraviolet irradiation.
- the coloring agent present in the UV-irradiated area usually develops color.
- a sensitizer or photoactive agent having a maximum absorption wavelength in the range of 200 to 230 nm absorbs ultraviolet rays and is activated to generate an acid and/or radical
- the color former is the acid and/or It develops color by reacting with radicals and the like.
- the amount of acid and/or radicals generated from the photoactive agent varies depending on the amount of UV irradiation. The amount of is also different.
- the color density varies depending on the amount of ultraviolet irradiation, and a colored portion is formed with a color-developing density corresponding to the amount of ultraviolet irradiation.
- the lower limit of the thickness of the ultraviolet sensing member 10 is preferably 0.1 ⁇ m or more, more preferably 0.5 ⁇ m or more. Also, the upper limit is preferably 1 cm or less, more preferably 2 mm or less.
- a support is a member for supporting the ultraviolet sensitive layer. If the ultraviolet sensitive layer itself can be handled, the ultraviolet sensitive member may not have a support.
- the support examples include resin sheets, paper (including synthetic paper), cloth (including woven fabric and non-woven fabric), glass, wood, and metal.
- the support is preferably a resin sheet or paper, more preferably a resin sheet or synthetic paper, and still more preferably a resin sheet.
- Materials for the resin sheet include polyethylene-based resin, polypropylene-based resin, cyclic polyolefin-based resin, polystyrene-based resin, acrylonitrile-styrene copolymer, acrylonitrile-butadiene-styrene copolymer, polyvinyl chloride-based resin, fluorine-based resin, Poly(meth)acrylic resins, polycarbonate resins, polyester resins (polyethylene terephthalate, polyethylene naphthalate, etc.), polyamide resins such as nylon, polyimide resins, polyamideimide resins, polyarylphthalate resins, silicone resins, polysulfone-based resins, polyphenylene sulfide-based resins, polyethersulfone-based resins, polyurethane-based resins, acetal-based resins, and cellulose-based resins.
- polyethylene-based resin polypropylene-based resin, cyclic polyolefin-based
- Synthetic papers include biaxially stretched polypropylene or polyethylene terephthalate or the like to form a large number of microvoids (Yupo, etc.), polyethylene, polypropylene, polyethylene terephthalate, and polyamide, and other synthetic fibers. Examples include a part of paper, a product laminated on one side or both sides of the paper, and the like.
- the resin sheet is a white resin sheet in which a white pigment is dispersed in a resin.
- the material of the resin in the white resin sheet include the same materials as those of the resin sheet described above.
- the white resin sheet has ultraviolet reflectivity. Therefore, when the support is a white resin sheet, the ultraviolet rays irradiated to the ultraviolet sensing member are reflected by the support, so that scattering of the ultraviolet rays inside the ultraviolet sensing member can be suppressed. As a result, the detection accuracy of the ultraviolet irradiation amount of the ultraviolet sensing member can be further improved.
- the white resin sheet is preferably, for example, a white polyester sheet, more preferably a white polyethylene terephthalate sheet.
- white resin sheets include Yupo (manufactured by Yupo Corporation), Lumirror (manufactured by Toray Industries, Inc.), and Crisper (manufactured by Toyobo Co., Ltd.).
- the lower limit of the thickness of the support is preferably 5 ⁇ m or more, more preferably 25 ⁇ m or more, and even more preferably 50 ⁇ m or more.
- the upper limit is preferably 1 cm or less, more preferably 2 mm or less, and even more preferably 500 ⁇ m.
- the UV-sensitive layer contains a sensitizer having a maximum absorption wavelength in the range of 200-230 nm, a photoactive agent, a color former, and a binder resin.
- the various components that may be included in the UV sensitive layer are detailed below. The aspects of the sensitizer, photoactive agent, and color former are as described above.
- the UV sensitive layer contains a binder resin.
- Various resins can be used as the binder resin of the present invention, but aliphatic resins are preferable because they have a high transmittance for ultraviolet rays with a wavelength of 200 to 230 nm, such as polyvinyl acetal resin, polyvinyl butyral resin, cellulose ester resin, Cellulose ester resins, acrylic resins, polycycloolefin resins, ethylene/vinyl acetate copolymer resins, polyamide resins, polyurethane resins, polyethylene resins, polypropylene resins, or polyester resins are preferred.
- polyvinyl acetal resin, polyvinyl butyral resin, and cellulose ether resin are particularly preferable from the viewpoint of color development of the color former.
- Preferred polyvinyl acetal resins and polyvinyl butyral resins of the present invention include S-LEC (manufactured by Sekisui Chemical Co., Ltd.), Mobital (manufactured by Kuraray Co., Ltd.), and Vinylec (manufactured by JNC), etc.
- S-LEC manufactured by Sekisui Chemical Co., Ltd.
- Mobital manufactured by Kuraray Co., Ltd.
- Vinylec manufactured by JNC
- Preferred cellulose ether resins of the present invention include methyl cellulose, ethyl cellulose, hydroxypropylmethyl cellulose, and hydroxyethyl methyl cellulose.
- the Marporose series, Dow Chemical Ethocel series, etc. can be obtained from the market.
- the binder resin may be used alone or in combination of two or more.
- the UV-sensitive layer of the present invention preferably contains 5% by mass or more, more preferably 20% by mass or more, and even more preferably 50% by mass or more of the above resin based on the total mass of the UV-sensitive layer. Although the upper limit is not particularly limited, it may be 90% by mass or less.
- the mass (solid content coating amount) per unit area of the UV-sensitive layer is not particularly limited, but is preferably 0.1 to 30 g/m 2 , more preferably 0.5 to 25 g/m 2 , more preferably 1 to 10 g/m 2 . More preferred is m2 .
- the thickness of the ultraviolet sensitive layer is preferably 0.1-30 ⁇ m, more preferably 0.5-25 ⁇ m, and even more preferably 1-10 ⁇ m.
- a method for forming the ultraviolet sensitive layer is not particularly limited, and known methods may be used. For example, there is a method of forming an ultraviolet sensitive layer by applying an ultraviolet sensitive layer forming liquid.
- the method of applying the ultraviolet-sensitive layer-forming liquid is not particularly limited, and examples of coating machines used for coating include air knife coaters, rod coaters, bar coaters, curtain coaters, gravure coaters, extrusion coaters, Die coaters, slide bead coaters, and blade coaters are included.
- the coating film may be dried, if necessary.
- drying treatment include heat treatment.
- a UV sensitive member may be formed comprising a UV sensitive layer.
- the temporary support is not particularly limited as long as it is a peelable support.
- the UV sensitive member may have layers other than the support and UV sensitive layer described above.
- Other layers include, for example, a reflective layer, a gloss layer, a filter layer, and a sensitivity adjustment layer.
- the UV sensitive member may further comprise a reflective layer.
- the ultraviolet sensitive layer includes a reflective layer
- the ultraviolet ray irradiated to the ultraviolet ray sensitive member can be reflected by the layer having ultraviolet reflective properties, so that scattering of the ultraviolet ray inside the ultraviolet ray sensitive member can be suppressed, and the detection accuracy of the ultraviolet irradiation amount can be improved.
- the reflective layer preferably has a reflectance of 10% or more, more preferably 50% or more, for light with a wavelength of 200 to 380 nm. The reflectance can be measured, for example, by diffuse reflectance measurement using an ultraviolet-visible spectrophotometer (UV-2700/Shimadzu Corporation).
- an adhesion layer may be provided between the support and the reflective layer.
- the reflective layer, the adhesion layer, and the production method thereof, the reflective layer, the adhesion layer, and the production method thereof described in paragraphs 0082 to 0091 of WO 2016/017701 can be referred to. The contents of which are incorporated herein.
- the UV sensitive member may further comprise a glossy layer.
- the UV-sensitive layer has a glossy layer, the front and back visibility can be improved.
- the glossy layer and its manufacturing method the glossy layer and its manufacturing method described in paragraphs 0092 to 0094 of WO 2016/017701 can be referred to, and the contents thereof are incorporated herein.
- the UV sensitive member further comprises a filter layer.
- a filter layer is a layer that selectively transmits light of a specific wavelength.
- "selectively transmit light of a specific wavelength” means to transmit light of a specific wavelength and block other light.
- the transmittance of light having a wavelength to be transmitted is, for example, preferably 70% or more, more preferably 80% or more, and even more preferably 90% or more.
- the transmittance of light having a wavelength to be blocked is preferably 30% or less, more preferably 20% or less, and even more preferably 10% or less.
- the filter layer is preferably a filter layer that blocks light with a wavelength of 300 nm or more, and more preferably a filter layer that blocks light with a wavelength of over 230 nm.
- An ultraviolet bandpass filter, a filter containing a dielectric, or the like is preferably used.
- the spectral characteristics of the filter layer and the sensitivity adjustment layer described later can be measured using, for example, an ultraviolet-visible spectrophotometer (UV-2700/Shimadzu Corporation).
- the filter layer preferably contains an ultraviolet absorber in order to block light of wavelengths other than the specific wavelength.
- a known ultraviolet absorber can be used as the ultraviolet absorber.
- the filter layer and its manufacturing method As for the filter layer and its manufacturing method, the filter layer and its manufacturing method described in paragraphs 0016 to 0026 of International Publication No. 2016/017701 can be considered, and the contents thereof are incorporated herein.
- the ultraviolet sensing member When the ultraviolet sensing member has a filter layer, it may further have a sensitivity adjusting layer on the surface of the filter layer.
- a sensitivity adjusting layer and its manufacturing method reference can be made to the sensitivity adjusting layer and its manufacturing method described in paragraphs 0095 to 0109 of WO 2016/017701, and the contents thereof are incorporated herein.
- a KrCl (krypton chloride) excimer lamp is used as a light source, and an irradiation amount of light with a wavelength of 222 nm is emitted through a filter that substantially blocks light with a wavelength of 230 to 300 nm.
- the cyan of the ultraviolet sensing member before light irradiation and the ultraviolet sensing member after light irradiation using a spectrophotometer X Light manufactured by X-Rite
- the optical density of magenta, and the optical density of yellow are respectively measured
- the value of the cyan optical density of the ultraviolet sensing member before light irradiation is C1
- the cyan optical density of the ultraviolet sensing member after light irradiation is measured.
- C2 is the density value
- Y1 is the yellow optical density value of the UV sensing member before light irradiation
- Y2 is the yellow optical density value of the UV sensing member after light irradiation
- Y2 is the magenta value of the UV sensing member before light irradiation.
- the ultraviolet sensing member has an optical density change rate represented by -50% or more and 50% or less.
- the second embodiment of the ultraviolet sensing member of the present invention when irradiated with ultraviolet rays having a wavelength of 222 nm at an integrated illuminance (irradiation amount) of 3 mJ/cm 2 , the color changes, so the new coronavirus is inactive. It is easy to determine whether or not the irradiation dose to be converted has been irradiated. Further, it was found that the second embodiment of the ultraviolet sensing member of the present invention has a small change in optical density when stored at room temperature after being irradiated with light. Below, first, the above characteristics of the ultraviolet sensing member will be described in detail.
- the ultraviolet sensing member is irradiated with light through a filter that substantially blocks light with a wavelength of 230 to 300 nm until the irradiation amount of light with a wavelength of 222 nm reaches 3 mJ/cm 2 .
- the size of the ultraviolet sensing member to be irradiated with light is preferably 5 mm to 10 mm in the vertical direction and 5 mm to 300 mm in the horizontal direction from the viewpoint of ease of handling.
- a filter that substantially blocks light with a wavelength of 230 to 300 nm means a filter that blocks 70 to 100% of light with a wavelength of 230 to 300 nm.
- the filter has a maximum transmittance of 30% or less in the wavelength range of 230 to 300 nm.
- Chemical filters or filters containing dielectrics are often used as such filters.
- An ultraviolet irradiation device Care222 (registered trademark) sold by Ushio Inc. was used as an ultraviolet irradiation device having a KrCl excimer lamp as a light source and provided with a filter that substantially blocks light with a wavelength of 230 to 300 nm. good too.
- Care222 (registered trademark) combines a lamp whose main wavelength is ultraviolet light with a wavelength of 222 nm, which is suitable for sterilization, and a filter that limits the wavelength range (200 to 230 nm wavelength) that is harmless to the human body.
- the illuminance and irradiation time during irradiation are not particularly limited, and the irradiation amount can be set to 3 mJ/cm 2 by adjusting the distance between the light source and the ultraviolet sensing member and the irradiation time. As an example, it is preferable to set the dose to 3 mJ/cm 2 for about 10 seconds (preferably 9 seconds).
- a predetermined amount of irradiation may be applied to the ultraviolet sensing member using a known ultraviolet measuring instrument (for example, a handheld photometer UIT2400 (manufactured by Ushio Inc.)).
- a known ultraviolet measuring instrument for example, a handheld photometer UIT2400 (manufactured by Ushio Inc.)
- the cyan optical density, the magenta optical density, and the yellow optical density of the ultraviolet sensing member before light irradiation and the ultraviolet sensing member after light irradiation Measure each concentration value.
- the ultraviolet sensing member before light irradiation and the ultraviolet sensing member after light irradiation are measured, and when measuring, the optical density (OD) is measured in each mode of C (Cyan), M (Magenta), and Y (Yellow).
- a cyan optical density value (Y value), a magenta optical density value (M value), and a yellow optical density value (Y value) are measured.
- the value of the cyan optical density of the ultraviolet sensing member before light irradiation is C1
- the value of the cyan optical density of the ultraviolet sensing member two hours after light irradiation is C2
- the yellow value of the ultraviolet sensing member before light irradiation is Y1 is the optical density value
- Y2 is the yellow optical density value of the UV-sensing member two hours after the irradiation
- M1 is the magenta optical density value of the UV-sensing member before the irradiation, and two hours after the irradiation.
- the difference between C1 and C2 is the value obtained by subtracting the smaller one from the larger one of C1 and C2. If the values of C1 and C2 are the same, the difference between them is zero.
- the difference between Y1 and Y2 is the value obtained by subtracting the smaller one from the larger one of Y1 and Y2. If the values of Y1 and Y2 are the same, the difference between them is zero.
- the difference between M1 and M2 is the value obtained by subtracting the smaller one from the larger one of M1 and M2.
- the difference between them is zero.
- Any one of the difference between C1 and C2, the difference between Y1 and Y2, and the difference between M1 and M2 obtained by the above procedure is 0.20 or more, preferably 0.2 to 1.5. , 0.26 to 1.1 are more preferred.
- it is preferable that either one of the difference between C1 and C2 or the difference between M1 and M2 is 0.20 or more from the point of view that the effect of the present invention is more excellent.
- the difference between C1 and C2 is preferably 0.20 or more, more preferably 0.20 to 1.50, even more preferably 0.26 to 1.10.
- the value of C1 is often 0.00 to 0.10, preferably 0.00 to 0.05.
- the value of C2 is preferably 0.20 or more, more preferably 0.20 to 1.50.
- the difference between M1 and M2 is preferably 0.20 or more, more preferably 0.20 to 1.50, even more preferably 0.26 to 1.10.
- the value of M1 is often 0.00 to 0.1, preferably 0.00 to 0.05.
- the value of M2 is preferably 0.20 or more, more preferably 0.20 to 1.50.
- the difference between Y1 and Y2 is preferably 0.20 or more, more preferably 0.20 to 1.50, even more preferably 0.26 to 1.10.
- the value of Y1 is often 0.00 to 0.10, more preferably 0.00 to 0.05.
- the value of Y2 is preferably 0.20 or more, more preferably 0.20 to 1.50.
- the value of the cyan optical density of the ultraviolet sensing member 24 hours after the light irradiation is C3, the yellow optical density of the ultraviolet sensing member 24 hours after the light irradiation is Y3, and the value of the yellow optical density 24 hours after the light irradiation.
- the value of the magenta optical density of the ultraviolet sensing member is M3, from C2 and C3, Y2 and Y3, and M2 and M3, the optical density change rate of yellow, magenta, and cyan is obtained by the following formula (II). are calculated respectively.
- Optical density change rate (%) [(optical density after 24 hours of irradiation) - (optical density after 2 hours of irradiation)] / [(optical density after 2 hours of irradiation) - (optical density before irradiation)] x 100
- the above optical density change of the color that gives the largest difference among the difference between C1 and C2, the difference between Y1 and Y2, and the difference between M1 and M2 The rate is -50% or more and 50% or less.
- the optical density change rate is preferably ⁇ 50% or more and 50% or less, more preferably ⁇ 40% or more and 40% or less, and ⁇ 30% or more and 30% or less for all of yellow, magenta, and cyan. It is particularly preferred to have When the optical density change rate satisfies the above range, it becomes possible to stably store evidence for determining whether or not the amount of irradiation that inactivates the novel coronavirus has been applied for a certain period of time.
- the second embodiment of the ultraviolet sensing member of the present invention its configuration is not particularly limited as long as it satisfies the above characteristics.
- the included materials are preferably included. That is, the second embodiment of the ultraviolet sensing member of the present invention preferably contains a sensitizer having a maximum absorption wavelength in the range of 200 to 230 nm, a photoactive agent, and a coloring agent.
- the above-described first embodiment of the ultraviolet sensing member of the present invention includes the difference between C1 and C2, the difference between Y1 and Y2, and the difference between M1 and M2, which are measured by the method described in the second embodiment.
- any one of the differences between and is 0.20 or more, and out of the difference between C1 and C2, the difference between Y1 and Y2, and the difference between M1 and M2, the above-mentioned formula for the color that gives the maximum difference
- the optical density change rate represented by (II) is preferably -50% or more and 50% or less.
- the shape of the ultraviolet sensing member is not particularly limited, and may be a sheet shape, or various shapes such as a block shape such as a rectangular parallelepiped and a cylindrical shape can be used. Among them, a sheet-like ultraviolet sensing member, that is, an ultraviolet sensing sheet is preferably used. Further, as the shape of the sheet-shaped ultraviolet sensing member, various shapes such as square, rectangle, circle, ellipse, polygon other than quadrangle such as hexagon, and irregular shape can be used. Further, the sheet-shaped ultraviolet sensing member may be elongated. The UV sensitive member may be applied over other members.
- the ultraviolet sensing member When applied on another member, the ultraviolet sensing member may be attached via an adhesion layer such as a pressure sensitive adhesive or an adhesive, or may be manufactured as a part of another member.
- adhesion layer such as a pressure sensitive adhesive or an adhesive
- Other members are not particularly limited, and examples thereof include business cards, name tags, masks, cloth products (eg, shirts), cases (eg, smartphone cases, etc.), and paper products (eg, notebooks, calendars, etc.).
- the present invention also relates to an ultraviolet sensing kit including the ultraviolet sensing member (first embodiment and second embodiment) described above.
- the ultraviolet sensing kit includes at least the ultraviolet sensing member described above.
- the specific configuration of the UV sensing kit is not particularly limited. sheet, more preferably a filter sheet that blocks light with a wavelength of more than 230 nm), a light shielding bag (ultraviolet cut bag), a judgment sample, a limit sample (calibration sheet), a condensing jig such as a lens and a concave mirror, and an ultraviolet sensing member and another element selected from the group consisting of a holding member that holds a.
- the holding member may have an opening for irradiating the ultraviolet sensing member held with ultraviolet rays, or the holding member and the judgment sample may be integrated.
- the ultraviolet sensing member included in the ultraviolet kit of the present invention after irradiating the ultraviolet sensing member with light until the irradiation amount of light with a wavelength of 313 nm reaches 9 mJ/cm 2 , company), the yellow optical density, the magenta optical density, and the cyan optical density of the ultraviolet sensing member before light irradiation and the ultraviolet light sensing member after light irradiation are measured, respectively.
- the value of the cyan optical density of the ultraviolet sensing member is C4, the value of the cyan optical density of the ultraviolet sensing member after two hours of light irradiation is C5, the value of the yellow optical density of the ultraviolet sensing member before light irradiation is Y4, and the light Y5 is the yellow optical density value of the UV sensing member after 2 hours of irradiation, M4 is the magenta optical density value of the UV sensing member before light irradiation, and M4 is the magenta optical density value of the UV sensing member after 2 hours of light irradiation.
- the difference between C4 and C5 the difference between Y4 and Y5, and the difference between M4 and M5 are all preferably 0.15 or less.
- Photoactivator 1 2-methyl-4,6-bis(trichloromethyl)-1,3,5-triazine: manufactured by Tokyo Kasei Co., Ltd.
- Color former 1 Rhodamine B base: manufactured by Sigma-Aldrich Co., Ltd.
- leveling agent A polymer surfactant composed of the following components was used as the leveling agent 1.
- the ratio of each component is a molar ratio
- t-Bu means a tert-butyl group.
- Base material 1 A white polyethylene terephthalate sheet (trade name “Crisper K1212” manufactured by Toyobo Co., Ltd.) was used as the substrate 1 .
- the obtained ultraviolet sensitive layer forming liquid Ba-1 was filtered using a filter paper (#63, manufactured by Toyo Roshi Kaisha, Ltd.) with an absolute filtration accuracy of 10 ⁇ m, and then a metal sintered filter with an absolute filtration accuracy of 2.5 ⁇ m.
- a filter paper #63, manufactured by Toyo Roshi Kaisha, Ltd.
- a metal sintered filter with an absolute filtration accuracy of 2.5 ⁇ m.
- UV Sensing Sheet The UV sensing layer forming liquid Ba-1 after the filtration treatment was applied onto the substrate 1 using a bar coater so that the film thickness after drying was 2.5 ⁇ m. After drying at 120° C., the ultraviolet sensitive sheet No. 1 of the present invention was obtained. 101 was made.
- Ultraviolet Sensing Sheet No. 101 of the present invention was produced in the same manner as for No. 101. 102-103 were produced.
- the compounding amount of the coloring agent means parts by mass with respect to 100 parts by mass of the ultraviolet sensitive layer.
- the compounding amount of the photoactive agent means parts by weight with respect to 100 parts by weight of the ultraviolet sensitive layer.
- the compounding amount of the sensitizer means parts by mass with respect to 100 parts by mass of the ultraviolet sensitive layer.
- a molar ratio refers to the molar amount of photogenerator or sensitizer combined with one mole of color former.
- the coloring agent 1 corresponds to a coloring agent that develops color by the action of acid, and exhibits magenta color by the action of acid.
- the yellow optical density, the magenta optical density, and the C1 is the cyan optical density of the UV sensing member before light irradiation
- C2 is the cyan optical density of the UV sensing member after two hours of light irradiation
- Y1 is the yellow optical density value of the UV sensing member before light irradiation
- Y2 is the yellow optical density value of the UV sensing member after two hours
- Y2 is the magenta optical density value of the UV sensing member before light irradiation.
- the difference between C1 and C2, the difference between Y1 and Y2, and the difference between M1 and M2 were measured, where M1 and M2 were the magenta optical densities of the ultraviolet sensing member after 2 hours.
- the largest value among the difference between C1 and C2, the difference between Y1 and Y2, and the difference between M1 and M2 is shown in the "optical density difference" column of Table 2.
- the color (cyan, yellow, or magenta) that gave the largest optical density difference was measured after ultraviolet irradiation.
- Optical Density Change Rate [(optical density after 24 hours of irradiation) - (optical density after 2 hours of irradiation)] / [(optical density after 2 hours of irradiation) - (optical density before irradiation)] x 100
- Examples 1 to 3 of the present invention have a small difference between the color density after 2 hours from irradiation and the color density after 24 hours from irradiation. Recognize.
- Example 4 The ultraviolet inspection sensing member of Example 1 was irradiated with ultraviolet rays through a 313 nm band-pass filter using a Heraeus high-pressure mercury lamp so that the irradiation amount of light with a wavelength of 313 nm was 9 mJ/cm 2 .
- a spectrophotometer X-light manufactured by X-light Co., Ltd.
- the values of yellow optical density, magenta optical density, and cyan optical density are measured, and the cyan optical density of the ultraviolet sensing member before light irradiation is measured.
- C4 is the density value
- C5 is the cyan optical density value of the UV sensing member after 2 hours of light irradiation
- Y4 is the yellow optical density value of the UV sensing member before light irradiation
- 2 hours after light irradiation is UV sensing.
- Y5 was the yellow optical density value of the member
- M4 was the magenta optical density value of the UV sensing member before light irradiation
- M5 was the magenta optical density value of the UV sensing member after two hours of light irradiation.
- UV Sensing Member 12 Support 14 UV Sensing Layer
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Abstract
Description
紫外線照射量の測定において、例えば、特許文献1では、「UVラベル」(日油技研工業社製UV-H)を使用する方法、及び、特許文献2では、「UVスケール」(富士フイルム社製)を使用する方法が開示されている。
このような状況において、非特許文献1においては、波長222nmの紫外線を用いた新型コロナウイルスの不活性化効果が報告されている。より具体的には、非特許文献1では、照度0.1mW/cm2の波長222nmの紫外線を30秒間照射することで99.7%の新型コロナウイルスの不活性化が達成されることが報告されている。
本発明者らは、従来公知のUVラベル及びUVスケールを用いて、新型コロナウイルス感染症の不活性化される波長222nmの光の照射量が照射されたかどうかの計測を行ったところ、UVラベル及びUVスケールでは色味の変化がほとんど見られず、照射量の判定ができなかった。より具体的には、UVラベル及びUVスケールに、積算照度3mJ/cm2にて波長222nmの紫外線を照射しても、色味の変化がほとんど見られなかった。
本発明の第2実施態様は、新型コロナウイルスが不活性化される照射量が照射されたかどうかの判定が容易で、一定期間にわたって判定の根拠を安定に保存できる、紫外線感知部材を提供することを課題とする。
本発明は、紫外線感知キットを提供することも課題とする。
吸収極大波長を200~230nmの範囲に有する増感剤と、光活性剤と、発色剤とを含む紫外線感知部材。
<2>
増感剤がナフタレン構造を有する、<1>の紫外線感知部材。
<3>
光活性剤がハロメチル-s-トリアジン構造を有する、<1>又は<2>の紫外線感知部材。
<4>
発色剤が下記式(I)で表されるスピロラクトン構造を有する、<1>~<3>のいずれかに記載の紫外線感知部材。
<5>
紫外線感知部材であって、
KrClエキシマランプを光源として用い、波長230~300nmの光を実質的に遮光するフィルタを介して、波長222nmの光の照射量が3mJ/cm2となるまで紫外線感知部材に光を照射した後、分光測色計Xライト(エックスライト社製)を用いて、光照射前の紫外線感知部材及び光照射後の紫外線感知部材のイエローの光学濃度、マゼンタの光学濃度、及び、シアンの光学濃度の値をそれぞれ測定し、光照射前の紫外線感知部材のシアンの光学濃度の値をC1、光照射2時間後の紫外線感知部材のシアンの光学濃度の値をC2、光照射24時間後の紫外線感知部材のシアンの光学濃度の値をC3、光照射前の紫外線感知部材のイエローの光学濃度の値をY1、光照射2時間後の紫外線感知部材のイエローの光学濃度の値をY2、光照射24時間後の紫外線感知部材のイエローの光学濃度の値をY3、光照射前の紫外線感知部材のマゼンタの光学濃度の値をM1、光照射2時間後の紫外線感知部材のマゼンタの光学濃度の値をM2、光照射24時間後の紫外線感知部材のマゼンタの光学濃度の値をM3、とした際に、C1とC2との差、Y1とY2との差、及び、M1とM2との差のいずれか一つが0.20以上であり、C1とC2との差、Y1とY2との差、及び、M1とM2との差のうち、最大の差を与える色の下記式(II)で表される光学濃度変化率が-50%以上50%以下である紫外線感知部材。
式(II)
光学濃度変化率(%)=[(照射24時間後の光学濃度)-(照射2時間後の光学濃度)]/[(照射2時間後の光学濃度)-(照射前の光学濃度)]×100
<6>
C1とC2との差、Y1とY2との差、M1とM2との差、及び光学濃度変化率が<5>の要件を満たす、<1>~<4>のいずれかに記載の紫外線感知部材。
<7>
シート状である、<1>~<6>のいずれかに記載の紫外線感知部材。
<8>
<1>~<7>のいずれかに記載の紫外線感知部材を含む、紫外線感知キット。
<9>
<1>~<7>のいずれかに記載の紫外線感知部材を含み、波長313nmの光の照射量が9mJ/cm2となるまで紫外線感知部材に光を照射した後、分光測色計Xライト(エックスライト社製)を用いて、光照射前の紫外線感知部材及び光照射後の紫外線感知部材のイエローの光学濃度、マゼンタの光学濃度、及び、シアンの光学濃度の値をそれぞれ測定し、光照射前の紫外線感知部材のシアンの光学濃度の値をC4、光照射2時間後の紫外線感知部材のシアンの光学濃度の値をC5、光照射前の紫外線感知部材のイエローの光学濃度の値をY4、光照射2時間後の紫外線感知部材のイエローの光学濃度の値をY5、光照射前の紫外線感知部材のマゼンタの光学濃度の値をM4、光照射2時間後の紫外線感知部材のマゼンタの光学濃度の値をM5、とした際に、C4とC5との差、Y4とY5との差、及び、M4とM5との差のすべてが0.15以下である、紫外線感知キット。
本発明の第2実施態様によれば、新型コロナウイルスが不活性化される照射量が照射されたかどうかの判定が容易で、一定期間にわたって判定の根拠を安定に保存できる、紫外線感知部材を提供できる。
本発明によれば、紫外線感知キットを提供できる。
なお、以下に記載する構成要件の説明は、本発明の代表的な実施態様に基づいてなされることがあるが、本発明はそのような実施態様に制限されるものではない。
本明細書において、「~」を用いて表される数値範囲は、「~」の前後に記載される数値を下限値及び上限値として含む範囲を意味する。
また、本明細書に段階的に記載されている数値範囲において、ある数値範囲で記載された上限値又は下限値は、他の段階的な記載の数値範囲の上限値又は下限値に置き換えてもよい。また、本明細書に記載されている数値範囲において、ある数値範囲で記載された上限値又は下限値は、実施例に示されている値に置き換えてもよい。
また、本明細書において、固形分とは、組成物を用いて形成される組成物層を形成する成分を意味し、組成物が溶媒(例えば、有機溶媒及び水等)を含む場合、溶媒を除いた全ての成分を意味する。また、組成物層を形成する成分であれば、液体状の成分も固形分とみなす。
また、本明細書において、紫外線とは、波長領域が10~400nmの光を意味する。
また、本明細書において、(メタ)アクリルとは、「アクリル及びメタクリルの少なくとも一方」を意味する。
また、本明細書において、「沸点」とは標準大気圧における沸点を意味する。
本発明の紫外線感知部材の第1実施態様は、吸収極大波長を200~230nmの範囲に有する増感剤と、光活性剤と、発色剤とを含む。
紫外線感知部材は、後述するように、支持体と、紫外線感知層とを有する態様が好ましく、このような場合、紫外線感知層が吸収極大波長を200~230nmの範囲に有する増感剤と、光活性剤と、発色剤とを含むことが好ましい。
以下、紫外線感知部材(または、紫外線感知層)に含まれる各材料について詳述する。
紫外線感知部材の第1実施態様は、発色剤を含む。なかでも、紫外線感知部材は、発色剤を含む紫外線感知層を含むことが好ましい。紫外線感知部材の具体的な構成は、後段で詳述する。
ここで、「発色剤」とは、実質的に無色である状態(無色であるか又は弱い色を呈している状態)から、酸の作用、酸化、及び、光照射等によって、発色する化合物を指す。
発色剤の種類は特に制限されず、例えば、酸化されて発色する発色剤、酸の作用により発色する発色剤、及び、光の作用により発色する発色剤が挙げられる。なかでも、酸化されて発色する発色剤、又は、酸の作用により発色する発色剤が好ましく、酸の作用により発色する発色剤がより好ましい。
発色剤としては、ロイコ色素又はフォトクロミック色素が好ましく、ロイコ色素がより好ましい。
フォトクロミック色素としては、光の作用により異性化して発色する化合物、光の作用により閉環反応が進行して発色する化合物、及び、光の作用により開環反応が進行して発色する化合物等が知られており、公知のフォトクロミック色素を使用できる。フォトクロミック色素としては、エネルギーにより発色消色反応が可逆的に進行するものが好ましい。
ロイコ色素としては、例えば、トリアリールメタンフタリド系化合物、フルオラン系化合物、フェノチアジン系化合物、インドリルフタリド系化合物、アザインドリルフタリド系化合物、ロイコオーラミン系化合物、ローダミンラクタム系化合物、トリアリールメタン系化合物、ジアリールメタン系化合物、トリアゼン系化合物、スピロピラン系化合物、チアジン化合物、及び、フルオレン系化合物が挙げられる。
上記の化合物の詳細については、米国特許第3445234号、特開平5-257272号公報、及び、国際公開第2009/008248号の段落0029~0034の記載を参照できる。
発色剤は、1種類を単独で用いてもよいし、2種類以上を混合して用いてもよい。
酸化発色性ロイコ色素の一態様としては、電子を除去することによって発色する、1個又は2個の水素原子を有している化合物であるのが好ましい。このような酸化発色性ロイコ色素としては、例えば、米国特許3445234号明細書に記載されているような、(a)アミノトリアリールメタン、(b)アミノキサンチン、(c)アミノチオキサンチン、(d)アミノ-9,10-ジヒドロアクリジン、(e)アミノフェノキサジン、(f)アミノフェノチアジン、(g)アミノジヒドロフェナジン、(h)アミノジフェニルメタン、(i)ロイコインダミン、(j)アミノヒドロシンナミック酸(シアンエタン、ロイコメチン)、(k)ヒドラジン、(l)ロイコインジゴイド染料、(m)アミノ-2,3-ジヒドロアントラキノン、(n)テトラハロ-p,p’-ビフェノール、(o)2-(p-ヒドロキシフェニル)-4,5-ジフェニルイミダゾール、及び、(p)フェネチルアニリン等が挙げられる。上述の(a)~(p)のうち、(a)~(i)は、1つの水素原子を失うことにより発色し、(j)~(p)のものは2つの水素原子を失うことにより発色する。
アミノトリアリールメタンとしては、下記式(L)で表される化合物又はその酸塩が好ましい。
Ar3は、Ar1及びAr2のうち少なくとも一方と同一の基を表すか、又は、Ar1及びAr2とは異なる基を表す。Ar3がAr1及びAr2とは異なる基を表す場合、Ar3は、(B1)低級アルキル基(好ましくは、炭素数1~4のアルキル基)、低級アルコキシ基(好ましくは、炭素数1~4のアルコキシ基)、塩素原子、ジフェニルアミノ基、シアノ基、ニトロ基、ヒドロキシ基、フッ素原子、臭素原子、アルキルチオ基、アリールチオ基、チオエステル基、アルキルスルフォン酸基、アリールスルフォン酸基、スルフォン酸基、スルフォンアミド基、アルキルアミド基、及びアリールアミド基からなる群から選ばれる置換基で置換されていてもよいフェニル基、(B2)アミン基、ジ-低級アルキルアミノ基、及びアルキルアミノ基からなる群から選ばれる置換基で置換されていてもよいナフチル基、(B3)アルキル基で置換されていてもよいピリジル基、(B4)キノリル基、又は、(B5)アルキル基で置換されていてもよいインドリニリデン基を表す。
また、上記式(L)において、Ar1、Ar2、及び、Ar3は、いずれも(A1)式中に明示されるメタン炭素原子への結合に対してパラ位にあるR1R2N-置換基を有するフェニル基を表すのが好ましく、なかでも、同一の基であるのが好ましい。
酸発色性ロイコ色素の一態様としては、電子を供与して、又は酸等のプロトンを受容して発色する化合物であるのが好ましい。具体的には、ラクトン、ラクタム、サルトン、スピロピラン、エステル、及び、アミド等の部分骨格を有し、酸又はプロトンと接触してこれらの部分骨格が開環若しくは開裂する化合物が挙げられる。
酸の作用により発色するロイコ色素(酸発色性ロイコ色素)としては、例えば、3,3-ビス(2-メチル-1-オクチル-3-インドリル)フタリド、6’-(ジブチルアミノ)-2’-ブロモ-3’-メチルスピロ[フタリド-3,9’-キサンテン]、3-(4-ジエチルアミノ-2-エトキシフェニル)-3-(1-エチル-2-メチルインドール-3-イル)-4-アザフタリド、3-(4-ジエチルアミノ-2-エトキシフェニル)-3-(1-n-オクチル-2-メチルインドール-3-イル)フタリド、3-[2,2-ビス(1-エチル-2-メチルインドール-3-イル)ビニル]-3-(4-ジエチルアミノフェニル)-フタリド、2-アニリノ-6-ジブチルアミノ-3-メチルフルオラン、6-ジエチルアミノ-3-メチル-2-(2,6-キシリジノ)-フルオラン、2-(2-クロロアニリノ)-6-ジブチルアミノフルオラン、3,3-ビス(4-ジメチルアミノフェニル)-6-ジメチルアミノフタリド、2-アニリノ-6-ジエチルアミノ-3-メチルフルオラン、9-[エチル(3-メチルブチル)アミノ]スピロ[12H-ベンゾ[a]キサンテン-12,1’(3’H)イソベンゾフラン]-3’-オン、2’-メチル-6’-(N-p-トリル-N-エチルアミノ)スピロ[イソベンゾフラン-1(3H),9’-[9H]キサンテン]-3-オン、3’,6’-ビス(ジエチルアミノ)-2-(4-ニトロフェニル)スピロ[イソインドール-1,9’-キサンテン]-3-オン、9-(N-エチル-N-イソペンチルアミノ)スピロ[ベンゾ[a]キサンテン-12,3’-フタリド]、2’-アニリノ-6’-(N-エチル-N-イソペンチルアミノ)-3’-メチルスピロ[フタリド-3,9’-[9H]キサンテン]、及び、6’-(ジエチルアミノ)-1’,3’-ジメチルフルオランが挙げられる。
式(I)において、R19で表されるアルキル基は、炭素数1~30のアルキル基が好ましく、炭素数1~15のアルキル基がより好ましく、炭素数1~10のアルキル基が更に好ましい。上記アルキル基は、直鎖状であっても、分岐を有していても、環構造を有していてもよい。具体的には、例えば、メチル基、エチル基、プロピル基、ブチル基、ペンチル基、ヘキシル基、ヘプチル基、オクチル基、ノニル基、デシル基、ウンデシル基、ドデシル基、トリデシル基、ヘキサデシル基、オクタデシル基、エイコシル基、イソプロピル基、イソブチル基、s-ブチル基、tert-ブチル基、イソペンチル基、ネオペンチル基、1-メチルブチル基、イソヘキシル基、2-エチルヘキシル基、2-メチルヘキシル基、シクロヘキシル基、シクロペンチル基、及び、2-ノルボルニル基が挙げられる。アルキル基の中で、メチル基、エチル基、プロピル基又はブチル基が好ましい。
上記アルキル基は、置換基を有していてもよい。置換基の例としては、アルコキシ基、アリーロキシ基、アミノ基、アルキルチオ基、アリールチオ基、ハロゲン原子、カルボキシ基、カルボキシレート基、スルホ基、スルホネート基、アルキルオキシカルボニル基、アリールオキシカルボニル基、及び、これらを組み合わせた基等が挙げられる。
R19で表されるアリール基は、炭素数6~30のアリール基が好ましく、炭素数6~20のアリール基がより好ましく、炭素数6~12のアリール基が更に好ましい。
上記アリール基は、置換基を有していてもよい。置換基の例としては、アルキル基、アルコキシ基、アリーロキシ基、アミノ基、アルキルチオ基、アリールチオ基、ハロゲン原子、カルボキシ基、カルボキシレート基、スルホ基、スルホネート基、アルキルオキシカルボニル基、アリールオキシカルボニル基、及び、これらを組み合わせた基等が挙げられる。
具体的には、例えば、フェニル基、ナフチル基、p-トリル基、p-クロロフェニル基、p-フルオロフェニル基、p-メトキシフェニル基、p-ジメチルアミノフェニル基、p-メチルチオフェニル基、p-フェニルチオフェニル基等が挙げられる。
アリール基の中で、フェニル基、p-メトキシフェニル基、p-ジメチルアミノフェニル基又はナフチル基が好ましい。
Rで表される1価の置換基としては、アルキル基、アルコキシ基、アリール基、アリーロキシ基、アミノ基、アルキルチオ基、アリールチオ基、ハロゲン原子、カルボキシル基、カルボキシレート基、スルホ基、スルホネート基、アルキルオキシカルボニル基、アリールオキシカルボニル基が好ましい。ここで、1価の置換基に含まれるアルキル基及びアリール基は、上記R19におけるアルキル基及びアリール基の記載を援用することができる。
式(I)において、Xは酸素原子であることが発色効率の観点で好ましい。
酸発色剤として機能する化合物の具体例を以下に示すが、本発明はこれらに限定されるものではない。
上記発色剤の含有量は、紫外線感知部材から紫外線感知層を多く有する面積を切り出して、紫外線感知層をアセトニトリルに2日間浸漬させた後、得られた溶剤を液体クロマトグラフィーで分析することにより、算出できる。なお、浸漬させている間はアセトニトリルが揮発しないようにする。なお、必要に応じて、液体クロマトグラフィーの測定の前に、検出する発色剤の含有量の検量線を作成してもよい。
液体クロマトグラフィーの測定条件は以下の通りである。
装置:島津製作所製Nexera
カラム:Capcell pak C18 UG-120
溶離液:水/アセトニトリル
オーブン:40℃
注入:5μL
検出:検出する発色剤の最大吸収波長
流速:0.2mL/min
紫外線感知部材の第1実施態様は、光活性剤を含む。なかでも、紫外線感知部材に含まれる紫外線感知層は、光活性剤を含むことが好ましい。
光活性剤は、光活性剤自身が光を吸収するか、又は、光を吸収した他の化合物から電子、正孔、もしくはエネルギーを受け取ることにより活性化される化合物であれば特に制限されないが、光により活性化された光活性剤が、発色剤に作用して発色することが好ましく、紫外線により活性化される化合物であることが好ましい。光活性剤としては、光酸化剤及び光酸発生剤のいずれか1種以上であることが好ましい。紫外線感知部材が酸化されて発色する発色剤を含む場合には、光活性剤は光酸化剤を含むことが好ましく、紫外線感知部材が酸の作用により発色する発色剤を含む場合には、光活性剤は光酸発生剤を含むことが好ましい。
発色剤の含有量に対する光活性剤の含有量の質量比(光活性剤/発色剤(質量比))としては、本発明の効果がより優れる点で、1.00超が好ましく、3.00以上がより好ましい。上限は特に制限されないが、40.00以下が好ましく、30.00以下がより好ましく、25.00以下が更に好ましく、20.00以下が特に好ましうく、10.00以下が最も好ましい。発色剤の含有量に対する光活性剤の含有量の質量比を上記範囲にすることで、発色剤による過剰な222nmの吸収が抑制され、光活性剤または増感剤が効率よく222nmを吸収することで、発色反応が効率よく進行し、後述する第2実施形態での光学濃度差を0.20以上にできるものと推察している。
上記発色剤の含有量に対する光活性剤の含有量の質量比は、上述した発色剤の含有量と同様に、メタノール抽出して液体クロマトグラフィーにて測定できる。なお、光活性剤は検出する光活性剤の最大吸収波長にて検出し、発色剤は検出する発色剤の最大吸収波長にて検出し、その質量比を求める。
光酸化剤としては、紫外線により活性化されて、ラジカルを発生する、及び/又は、発色剤の水素原子を引き抜く作用を示すことにより発色剤を呈色し得る化合物であるのが好ましい。
光酸化剤としては、なかでも、ラジカル発生剤及び有機ハロゲン化合物の1種以上であるのが好ましい。光酸発生剤として、ラジカル発生剤及び有機ハロゲン化合物を併用する態様も好ましい。ラジカル発生剤及び有機ハロゲン化合物を併用する場合、有機ハロゲン化合物に対するラジカル発生剤の含有量比(ラジカル発生剤/有機ハロゲン化合物(質量比))としては、発色部の階調性がより優れる点で、0.1~10であるが好ましく、0.5~5であるのがより好ましい。
ラジカル発生剤としては、紫外線により活性化されてラジカルを発生する化合物であれば特に制限されない。
ラジカル発生剤としては、水素引抜型ラジカル発生剤が好ましい。水素引抜型ラジカル発生剤は、発色剤から水素原子を引き抜いて発色剤の酸化を促進する作用を示す。
ラジカル発生剤としては、例えば、日本写真学会1968年春季研究発表会講演要旨55頁記載のアジドポリマー;米国特許第3,282,693号記載の2-アジドベンゾオキサゾール、ベンゾイルアジド、及び、2-アジドベンズイミダゾール等のアジド化合物;米国特許第3,615,568号記載の3’-エチル-1-メトキシ-2-ピリドチアシアニンパークロレート、及び、1-メトキシ-2-メチルピリジニウムp-トルエンスルホネート等;特公昭62-039728号記載の2,4,5-トリアリールイミダゾール二量体等のロフィンダイマー化合物;ベンゾフェノン;p-アミノフェニルケトン;多核キノン;チオキサンテノン;等が挙げられる。
なかでも、ロフィンダイマー及びベンゾフェノンから選択される1種以上が好ましく、ロフィンダイマーがより好ましい。
ロフィンダイマーとしては、例えば、ヘキサアリールビイミダゾール化合物が挙げられる。ヘキサアリールビイミダゾール系化合物としては、国際公開第2016/017701号の段落0047に記載された化合物を参酌でき、これらの内容は本明細書に組み込まれる。
なかでも、2,2’-ビス(2-クロロフェニル)-4,4’,5,5’-テトラフェニル-1,2’-ビイミダゾールが好ましい。2,2’-ビス(2-クロロフェニル)-4,4’,5,5’-テトラフェニル-1,2’-ビイミダゾールとしては、例えば、「B-IMD」(黒金化成社製)、及び、「B-CIM」(保土ヶ谷化学工業社製)を使用できる。
B及びDは、各々独立に、無置換であるか、又は、1~3個の置換基を有するのが好ましく、Aは、無置換であるか、又は、1~4個の置換基を有するのが好ましい。
一般式(1)で表される化合物及びそれらの製法は、ロフィンダイマー等として知られる知見を利用できる。例えば、米国特許第3552973号明細書の第4欄第22行及び第6欄第3行の記載が挙げられ、これらの内容は本明細書に組み込まれる。
有機ハロゲン化合物は、発色剤の酸化を促進し得る。
有機ハロゲン化合物としては、発色部の階調性がより優れる点で、分子内のハロゲン原子の個数が3個以上である化合物が好ましい。ハロゲン原子の個数の上限値としては、9個以下であるのが好ましい。なお、有機ハロゲン化合物は、ロフィンダイマー及びベンゾフェノン以外の化合物である。
有機ハロゲン化合物は、1種類を単独で用いてもよいし、2種類以上を混合して用いてもよい。
有機ハロゲン化合物としては、例えば、下記一般式(2)~(7)で表される化合物が挙げられる。
式中、P0は、水素原子、ハロゲン原子、置換基を有していてもよいアルキル基、又は、置換基を有していてもよいアリール基を表す。Xは、各々独立に、ハロゲン原子を表す。
P0及びXで表されるハロゲン原子としては、フッ素原子、塩素原子、臭素原子、及び、ヨウ素原子が挙げられ、塩素原子又は臭素原子が好ましい。
P0で表されるアルキル基及びアリール基が有し得る置換基としては、例えば、ヒドロキシ基、ハロゲン原子、炭素数1~6のアルキル基、炭素数1~6のハロアルキル基、アセチル基、及び、炭素数1~6のアルコキシ基等が挙げられる。
なお、式中にRが複数個存在する場合、R同士は互いに同一であっても異なっていてもよい。
R1で表されるアリール基としては、炭素数6~20のアリール基が好ましく、炭素数6~14のアリール基がより好ましく、炭素数6~10のアリール基が更に好ましい。
R1で表されるアルキル基及びアリール基が有し得る置換基としては、例えば、ニトロ基、ハロゲン原子、炭素数1~3のアルキル基、炭素数1~3のハロアルキル基、アセチル基、ハロアセチル基、及び、炭素数1~3のアルコキシ基が挙げられる。
X1で表されるハロゲン原子としては、フッ素原子、塩素原子、臭素原子、及び、ヨウ素原子が挙げられ、塩素原子、臭素原子、又は、ヨウ素原子が好ましく、塩素原子又は臭素原子がより好ましい。
X2で表されるハロゲン原子としては、フッ素原子、塩素原子、臭素原子、及び、ヨウ素原子が挙げられ、塩素原子、臭素原子、又は、ヨウ素原子が好ましく、塩素原子又は臭素原子がより好ましい。
R3で表されるヘテロアリール基としては、炭素数4~20のヘテロアリール基が好ましく、炭素数4~13のヘテロアリール基がより好ましく、炭素数4~9のヘテロアリール基が更に好ましい。
R3で表されるアリール基及びヘテロアリール基が有し得る置換基としては、例えば、ニトロ基、ハロゲン原子、炭素数1~3のアルキル基、炭素数1~3のハロアルキル基、アセチル基、ハロアセチル基、及び、炭素数1~3のアルコキシ基が挙げられる。
R4で表されるヘテロアリール基が有し得る置換基としては、例えば、ニトロ基、ハロゲン原子、炭素数1~3のアルキル基、炭素数1~3のハロアルキル基、アセチル基、ハロアセチル基、炭素数1~3のアルコキシ基が挙げられる。
X6、X7、及び、X8で表されるハロゲン原子としては、例えば、フッ素原子、塩素原子、臭素原子、及び、ヨウ素原子が挙げられ、塩素原子、臭素原子、又は、ヨウ素原子が好ましく、塩素原子又は臭素原子がより好ましい。
光酸発生剤としては、紫外線により開裂して酸を発生し、上記酸の作用によって発色剤を呈色し得る化合物であるのが好ましい。
光酸発生剤としては、ノニオン性光酸発生剤及びイオン性光酸発生剤が挙げられ、本発明の効果がより優れる点で、ノニオン性光酸発生剤が好ましい。ノニオン性光酸発生剤としては、有機ハロゲン化合物及びオキシム化合物が挙げられ、なかでも、本発明の効果がより優れる点で、有機ハロゲン化合物が好ましく、上述した一般式(7)で表される化合物がより好ましい。
有機ハロゲン化合物としては、発色部の階調性がより優れる点で、分子中のハロゲン原子の個数が3個以上である化合物が好ましい。ハロゲン原子の個数の上限値としては、9個以下であるのが好ましい。
有機ハロゲン化合物は、1種類を単独で用いてもよいし、2種類以上を混合して用いてもよい。
有機ハロゲン化合物の具体例としては、上段部において光酸化剤として挙げた有機ハロゲン化合物と同じものが挙げられる。
また、光酸発生剤としては、光により酸を発生する化合物であれば、特に制限はなく、ハロゲン化水素(例えば塩酸)、硫酸、及び、硝酸等の無機酸を発生する光酸発生剤であってもよく、カルボン酸及びスルホン酸等の有機酸を発生する光酸発生剤であってもよい。本発明の効果がより優れる点では、なかでも、無機酸を発生する光酸発生剤であるのが好ましく、ハロゲン化水素を発生する光酸発生剤であるのがより好ましい。
また、前述のハロメチル-s-トリアジン系化合物は本発明の光酸化剤としても特に好ましい。
紫外線感知部材の第1実施態様は、吸収極大波長を200~230nmの範囲に有する増感剤を含む。
本発明の増感剤は波長200~230nmの光を吸収して励起し、励起状態から電子、正孔、またはエネルギーを光活性剤に与えることにより光活性剤からラジカルあるいは酸を発生させる機能を有する。
また、新型コロナウイルス感染症が不活性化される波長222nmの光の照射量を高感度で検出する点から、本発明の増感剤は波長200~230nmの範囲に吸収極大波長を有する。
式(III)
ΔG=F×ED-F×EA-E* D-NA×e2/(4π×ε×ε0×r)
ここで
ΔG:反応の自由エネルギー変化
F:ファラデー定数
ED:増感剤の酸化電位
EA:光開始剤の還元電位
E* D:増感剤の励起エネルギー
NA:アボガドロ定数
e:電子の電荷
ε:バインダー樹脂の誘電率
ε0:真空の誘電率
r:二つの電荷間の距離
を表す。
本発明の増感剤としては波長200~230nmの光を吸収するものであれば様々の化合物を用いることができるが、ΔGをマイナスにする点から縮環式の芳香族化合物が好ましく、ナフタレン類、アントラセン類、ピレン類、カルバゾール類、ジベンゾフラン類、及び、ジベンゾチオフェン類等を好ましく用いることができる。これらのなかでもナフタレン類は波長200~230nmにおける吸光係数が大きい点から好ましい。つまり、増感剤がナフタレン構造を有することが好ましい。
増感剤は、1種類を単独で用いてもよいし、2種類以上を混合して用いてもよい。
また、本発明の光酸化剤に対する本発明の増感剤のモル比率は、0.1以上50以下が好ましく、1.0以上30以下がより好ましい。
さらに、本発明の発色剤に対する本発明の増感剤のモル比率は、本発明の増感剤が効率よく波長200~230nmの光を吸収できる点から、0.1以上が好ましく、1以上がより好ましい。上限は特にないが、50以下が現実的であり、30以下が好ましく、10以下がより好ましく、5以下が更に好ましい。
上記構成とすることで、後述する第2実施形態でのC1とC2との差、Y1とY2との差、及び、M1とM2との差のいずれか一つを0.20以上に制御しやすい。
紫外線感知部材10は、支持体12、及び、支持体12の一方の表面に配置された、吸収極大波長を200~230nmの範囲に有する増感剤、光活性剤と、発色剤と、バインダー樹脂とを含む紫外線感知層14を備える。紫外線の照射を受けた紫外線感知層14では、紫外線照射量に応じた発色濃度で発色した発色部(不図示)が形成される。
上述したように、図1においては、紫外線感知部材がシート状である態様について示しているが、この態様に限定されない。
更に、図1に示す紫外線感知部材10は、支持体12と紫外線感知層14との2層構成であるが、この態様に制限されず、後述するように、支持体12及び紫外線感知層14以外のその他の層(例えば、反射層、光沢層及びフィルタ層等)を備えていてもよい。
支持体は、紫外線感知層を支持するための部材である。
なお、紫外線感知層自体で取り扱いが可能な場合には、紫外線感知部材は支持体を有していなくてもよい。
樹脂シートの材料としては、ポリエチレン系樹脂、ポリプロピレン系樹脂、環状ポリオレフィン系樹脂、ポリスチレン系樹脂、アクリロニトリル-スチレン共重合体、アクリロニトリル-ブタジエン-スチレン共重合体、ポリ塩化ビニル系樹脂、フッ素系樹脂、ポリ(メタ)アクリル系樹脂、ポリカーボネート系樹脂、ポリエステル系樹脂(ポリエチレンテレフタレート及びポリエチレンナフタレート等)、各種のナイロン等のポリアミド系樹脂、ポリイミド系樹脂、ポリアミドイミド系樹脂、ポリアリールフタレート系樹脂、シリコーン系樹脂、ポリスルホン系樹脂、ポリフェニレンスルフィド系樹脂、ポリエーテルスルホン系樹脂、ポリウレタン系樹脂、アセタール系樹脂、及び、セルロース系樹脂等が挙げられる。
合成紙としては、ポリプロピレン又はポリエチレンテレフタレート等を二軸延伸してミクロボイドを多数形成したもの(ユポ等)、ポリエチレン、ポリプロピレン、ポリエチレンテレフタレート、及び、ポリアミド等の合成繊維を用いて作製したもの、並びに、これらを紙の一部、片面又は両面に積層したもの、等が挙げられる。
白色樹脂シートは、紫外線反射性を有する。このため、支持体が白色樹脂シートである場合、紫外線感知部材に照射された紫外線は支持体で反射するため、紫外線の紫外線感知部材内部における散乱を抑制できる。この結果として、紫外線感知部材の紫外線照射量の検出精度がより向上し得る。
白色樹脂シートは、例えば、白色ポリエステルシートが好ましく、白色ポリエチレンテレフタレートシートがより好ましい。
白色樹脂シートの市販品としては、ユポ(ユポコーポレーション社製)、ルミラー(東レ社製)、及び、クリスパー(東洋紡社製)等が挙げられる。
紫外線感知層は、吸収極大波長を200~230nmの範囲に有する増感剤、光活性剤と、発色剤と、バインダー樹脂を含む。
以下において、紫外線感知層に含まれ得る各種成分について詳述する。
なお、増感剤、光活性剤、及び、発色剤の態様は、上述した通りである。
紫外線感知層は、バインダー樹脂を含む。
本発明のバインダー樹脂としては、様々な樹脂が使用できるが、波長200~230nmの紫外線の透過率が高い点から、脂肪族系の樹脂が好ましく、ポリビニルアセタール樹脂、ポリビニルブチラール樹脂、セルロースエステル樹脂、セルロースエステル樹脂、アクリル樹脂、ポリシクロオレフィン樹脂、エチレン・酢酸ビニル共重合樹脂、ポリアミド樹脂、ポリウレタン樹脂、ポリエチレン樹脂、ポリプロピレン樹脂、又は、ポリエステル樹脂が好ましい。このなかでも、ポリビニルアセタール樹脂、ポリビニルブチラール樹脂、及びセルロースエーテル樹脂は発色剤の発色の点から特に好ましい。
具体的には、ポバールPVA403、PVA-624、PVA-706、PVA102、PVA203、PVA505、PVAHC、L-8、PVA-CST、L-9-78、LL-02、C-506、KL-05、KL-506や、エスレックBL-1、エスレックBL-1H、エスレックBL-2、エスレックBL-2H、エスレックBL-5、エスレックBL-10、エスレックBL-S、エスレックBX-L、エスレックBM-1、エスレックBM-S、エスレックBH-3、エスレックBX-1、エスレックKS-1、エスレックKS-10、エスレックKS-3や、モビタールB16H、モビタールB60HH、モビタール30T、モビタール30HH、モビタール60Tや、ビニレックK、ビニレックL、ビニレックH、ビニレックE等が挙げられるが、これらに限定されるものではない。
本発明の紫外線感知層は、紫外線感知層全質量に対して、上記樹脂を5質量%以上含むことが好ましく、20質量%以上含むことがより好ましく、50質量%以上含むことがさらに好ましい。上限は特に制限されないが、90質量%以下が挙げられる。
上記紫外線感知層の形成方法は特に制限されず、公知の方法が挙げられる。
例えば、紫外線感知層形成液を塗布して、紫外線感知層を形成する方法が挙げられる。
仮支持体としては、剥離性の支持体であれば特に制限されない。
紫外線感知部材は上述した支持体及び紫外線感知層以外のその他の層を有していてもよい。
その他の層としては、例えば、反射層、光沢層、フィルタ層、及び、感度調整層が挙げられる。
紫外線感知部材は、更に反射層を備えていてもよい。
紫外線感知層が反射層を備える場合、紫外線感知部材に照射された紫外線を、紫外線反射性を有する層にて反射できるので、紫外線の紫外線感知部材内部における散乱を抑制でき、紫外線照射量の検出精度をより向上できる。
反射層は、波長200~380nmの光に対する反射率は、10%以上が好ましく、50%以上がより好ましい。なお、反射率は、例えば、紫外可視分光光度計(UV-2700/島津製作所)を使用した拡散反射測定によって測定できる。
なお、支持体を反射層に隣接して配置する場合、支持体と反射層の間に密着層を設けてもよい。
反射層及び密着層並びにそれらの製造方法としては、国際公開第2016/017701号の段落0082~0091に記載された反射層及び密着層並びにそれらの製造方法を参酌できる。これらの内容は本明細書に組み込まれる。
紫外線感知部材は、更に光沢層を備えていてもよい。
紫外線感知層が光沢層を備える場合、表裏の視認性が向上し得る。
光沢層及びその製造方法としては、国際公開第2016/017701号の段落0092~0094に記載された光沢層及びその製造方法を参酌でき、これらの内容は本明細書に組み込まれる。
紫外線感知部材は、更にフィルタ層を備えていることが好ましい。
フィルタ層は、特定波長の光を選択的に透過する層である。ここで、「特定波長の光を選択的に透過」するとは、特定波長の光を透過させ、それ以外の光を遮光させることを意味する。透過させる波長の光の透過率は、例えば、70%以上が好ましく、80%以上がより好ましく、90%以上が更に好ましい。遮光させる波長の光の透過率は、例えば、30%以下が好ましく、20%以下がより好ましく、10%以下が更に好ましい。
フィルタ層は、波長300nm以上の光を遮光するフィルタ層であることが好ましく、波長230nm超の光を遮光するフィルタ層であることがより好ましい。紫外線バンドパスフィルタや誘電体を含むフィルタ等が好ましく用いられる。
なお、フィルタ層及び後述する感度調整層の分光特性は、例えば、紫外可視分光光度計(UV-2700/島津製作所)を用いて、測定できる。
フィルタ層は特定波長以外を遮光する点で、紫外線吸収剤を有することが好ましい。紫外線吸収剤としては、公知の紫外線吸収剤を使用できる。
紫外線感知部材がフィルタ層を備える場合、フィルタ層の表面に、更に感度調整層を備えていてもよい。
感度調整層及びその製造方法としては、国際公開第2016/017701号の段落0095~0109に記載された感度調整層及びその製造方法を参酌でき、これらの内容は本明細書に組み込まれる。
本発明の紫外線感知部材の第2実施態様は、KrCl(塩化クリプトン)エキシマランプを光源として用い、波長230~300nmの光を実質的に遮光するフィルタを介して、波長222nmの光の照射量が3mJ/cm2となるまで紫外線感知部材に光を照射した後、分光測色計Xライト(エックスライト社製)を用いて、光照射前の紫外線感知部材及び光照射後の紫外線感知部材のシアンの光学濃度、マゼンタの光学濃度、及び、イエローの光学濃度の値をそれぞれ測定し、光照射前の紫外線感知部材のシアンの光学濃度の値をC1、光照射後の紫外線感知部材のシアンの光学濃度の値をC2、光照射前の紫外線感知部材のイエローの光学濃度の値をY1、光照射後の紫外線感知部材のイエローの光学濃度の値をY2、光照射前の紫外線感知部材のマゼンタの光学濃度の値をM1、光照射後の紫外線感知部材のマゼンタの光学濃度の値をM2とした際に、C1とC2との差、Y1とY2との差、及び、M1とM2との差のいずれか一つが0.20以上であり、C1とC2との差、Y1とY2との差、及び、M1とM2との差のうち、最大の差を与える色の後述する式(II)で表される光学濃度変化率が-50%以上50%以下である、紫外線感知部材である。
また、本発明の紫外線感知部材の第2実施態様は、更に、光照射後室温で保管した際の光学濃度の変化が小さいことがわかった。
以下では、まず、紫外線感知部材の上記特性について詳述する。
波長230~300nmの光を実質的に遮光するフィルタとは、波長230~300nmの光を70~100%を遮光するフィルタを意味する。言い換えれば、上記フィルタは、波長230~300nmの範囲における最大透過率が30%以下であるフィルタである。このようなフィルタとしては、ケミカルフィルタ、又は、誘電体を含むフィルタが用いられることが多い。
KrClエキシマランプを光源とし、かつ、波長230~300nmの光を実質的に遮光するフィルタが設けられた紫外線照射装置として、ウシオ電機株式会社より販売される紫外線照射装置Care222(登録商標)を用いてもよい。Care222(登録商標)においては、殺菌に適した波長222nmの紫外線を主な波長とするランプと、人体に無害な波長域(波長200~230nm)に制限するフィルタとが組み合わされている。そのため、Care222(登録商標)を用いて光照射を行うと、主に、波長222nmの光が照射される。
照射の際の照度及び照射時間は特に制限されず、光源と紫外線感知部材との距離や照射時間を調節することで照射量を3mJ/cm2に設定できる。なお、一例としては、10秒程度(好ましくは、9秒)で照射量3mJ/cm2とすることが好ましい。
また、公知の紫外線計測器(例えば、ハンドヘルド光度計 UIT2400(ウシオ電機株式会社製)を用いて、所定量の照射量が紫外線感知部材に照射されたかどうかを計測してもよい。
次に、光照射前の紫外線感知部材のシアンの光学濃度の値をC1、光照射から2時間後の紫外線感知部材のシアンの光学濃度の値をC2、光照射前の紫外線感知部材のイエローの光学濃度の値をY1、光照射から2時間後の紫外線感知部材のイエローの光学濃度の値をY2、光照射前の紫外線感知部材のマゼンタの光学濃度の値をM1、光照射から2時間後の紫外線感知部材のマゼンタの光学濃度の値をM2とした際に、C1とC2との差、Y1とY2との差、及び、M1とM2との差を算出する。
C1とC2との差とは、C1及びC2のうち大きいほうから小さいほうを引いた値である。C1とC2との値が同じ場合は、両者の差は0である。
Y1とY2との差とは、Y1及びY2のうち大きいほうから小さいほうを引いた値である。Y1とY2との値が同じ場合は、両者の差は0である。
M1とM2との差とは、M1及びM2のうち大きいほうから小さいほうを引いた値である。M1とM2との値が同じ場合は、両者の差は0である。
上記手順によって、得られたC1とC2との差、Y1とY2との差、及び、M1とM2との差のいずれか一つが0.20以上であり、0.2~1.5が好ましく、0.26~1.1がより好ましい。
なかでも、本発明の効果がより優れる点から、C1とC2との差、又は、M1とM2との差のいずれか一つが0.20以上であることが好ましい。
C1とC2との差は、0.20以上が好ましく、0.20~1.50がより好ましく、0.26~1.10が更に好ましい。
C1の値は、0.00~0.10であることが多く、0.00~0.05が好ましい。
C2の値は、0.20以上が好ましく、0.20~1.50がより好ましい。
M1とM2との差は、0.20以上が好ましく、0.20~1.50がより好ましく、0.26~1.10が更に好ましい。
M1の値は、0.00~0.1であることが多く、0.00~0.05が好ましい。
M2の値は、0.20以上が好ましく、0.20~1.50がより好ましい。
Y1とY2との差は、0.20以上が好ましく、0.20~1.50がより好ましく、0.26~1.10が更に好ましい。
Y1の値は、0.00~0.10であることが多く、0.00~0.05がより好ましい。
Y2の値は、0.20以上が好ましく、0.20~1.50がより好ましい。
式(II)
光学濃度変化率(%)=[(照射24時間後の光学濃度)-(照射2時間後の光学濃度)]/[(照射2時間後の光学濃度)-(照射前の光学濃度)]×100
光学濃度変化率は、イエロー、マゼンタ、及びシアンいずれも、-50%以上50%以下であることが好ましく、-40%以上40%以下であることがより好ましく、-30%以上30%以下であることが特に好ましい。光学濃度変化率が上記範囲を満たすことにより、新型コロナウイルスが不活性化される照射量が照射されたかどうかの判定の証拠を一定期間にわたって安定に保管することが可能となる。
また、シート状の紫外線感知部材の形状としては、正方形、長方形、円形、楕円形、六角形等の四角形以外の多角形、及び、不定形等、各種の形状が利用可能である。また、シート状の紫外線感知部材は、長尺状であってもよい。
紫外線感知部材は、他の部材上に適用してもよい。他の部材上に適用する場合、粘着剤及び接着剤等の密着層を介して紫外線感知部材を貼り合わせてもよいし、他の部材の一部として製造してもよい。他の部材は特に制限されず、例えば、名刺、名札、マスク、布製品(例えば、シャツ)、ケース(例えば、スマートフォンケース等)、及び、紙製品(例えば、ノート、カレンダー等)が挙げられる。
また、本発明は、上述した紫外線感知部材(第1実施態様及び第2実施態様)を含む紫外線感知キットにも関する。
紫外線感知キットは、上述した紫外線感知部材を少なくとも含む。
紫外線感知キットの具体的な構成としては特に制限されず、例えば、紫外線感知部材と、特定波長の光を選択的に透過するフィルタ層を有する部材(好ましくは、波長300nm以上の光を遮光するフィルタシート、より好ましくは波長230nm超の光を遮光するフィルタシート)、遮光袋(紫外線カット袋)、判断見本、限度見本(キャリブレーションシート)、レンズ及び凹面鏡等の集光治具、並びに、紫外線感知部材を保持する保持部材からなる群から選ばれる他の要素と、を含む態様が挙げられる。
なお、上記保持部材は、保持した紫外線感知部材に紫外線が照射されるための開口部を有していてもよいし、保持部材と判断見本が一体となっていてもよい。
なお、以下の実施例において組成を表す「部」及び「%」は、特に断らない限り質量基準である。
なお、紫外線感知層形成液の調製工程から、紫外線感知層形成液を用いた紫外線感知部材の作製工程及び紫外線照射試験に用いるまでの工程は、いずれも、紫外線が照射されないよう、黄色灯下で行った。
[紫外線感知層の作製]
紫外線感知層の作製に用いた材料を次に示す。
<バインダー樹脂>
(樹脂1)
ポリブチラール樹脂(積水化学(株)製、エスレックKS-10(商品名)
増感剤2:1-メトキシナフタレン:東京化成(株)製;アセトニリル溶液における吸収極大波長=211nm
増感剤3:ナフタレン:東京化成(株)製;アセトニリル溶液における吸収極大波長=217nm
光活性剤1:2-メチル-4,6-ビス(トリクロロメチル)-1,3,5-トリアジン:東京化成(株)製
発色剤1:ローダミンBベース:シグマアルドリッチ(株)製
下記構成成分で構成されるポリマー界面活性剤をレベリング剤1として用いた。下記構造式中、各構成成分の割合はモル比であり、t-Buはtert-ブチル基を意味する。
白色ポリエチレンテレフタレートシート(商品名「クリスパーK1212」、東洋紡社製)を基材1として用いた。
<紫外線感知シートNo.101の作製>
各成分を下記に示す組成で混合し、紫外線感知層形成液(組成物)Ba-1を調製した。
―――――――――――――――――――――――――――――――――
紫外線感知層形成液Ba-1の組成
―――――――――――――――――――――――――――――――――
樹脂1 93.2質量部
増感剤1 1.18質量部
光活性剤1 4.54質量部
発色剤1 1.10質量部
レベリング剤1 0.08質量部
メチルエチルケトン(溶媒) 176.5質量部
エタノール(溶媒) 294.1質量部
―――――――――――――――――――――――――――――――――
上記濾過処理後の紫外線感知層形成液Ba-1を、基材1上に、乾燥後の膜厚が2.5μmとなるようにバーコーターを用いて塗布し、120℃で乾燥し、本発明の紫外線感知シートNo.101を作製した。
<紫外線感知シートNo.102~103の作製>
増感剤の種類と配合量、光活性剤の種類と配合量、及び発色剤の種類と配合量を、表1に記載の内容に変更した以外は紫外線感知シートNo.101の作製と同様にして、本発明の紫外線感知シートNo.102~103を作製した。
増感剤の種類と配合量、光活性剤の種類と配合量、及び発色剤の種類と配合量を、表1に記載の内容に変更した以外は紫外線感知シートNo.101の作製と同様にして、比較例の紫外線感知シートNo.201Cを作製した。
〔比較例1〕
市販のUVラベル(Sタイプ、日油技研工業(株)製)を用いた。
発色剤の配合量は、それぞれ紫外線感知層100質量部に対する質量部を意味する。光活性剤の配合量は、紫外線感知層100質量部に対する質量部を意味する。増感剤の配合量は紫外線感知層100質量部に対する質量部を意味する。
モル比率は、発色剤1モルに対する光発生剤、または増感剤の配合モル量を意味する。
また、発色剤1は、酸の作用により発色する発色剤に相当し、酸の作用によりマゼンタ色を呈する。
(波長222nmにおける光学濃度差)
Care222(登録商標)を用いて、波長222nmの光の照射量が3mJ/cm2となるまで各実施例で作製された紫外線感知部材に対して光を照射した。
光照射後2時間経過後に、分光測色計Xライト(エックスライト社製)を用いて、光照射前の紫外線感知部材及び光照射後の紫外線感知部材のイエローの光学濃度、マゼンタの光学濃度、及び、シアンの光学濃度の値をそれぞれ測定し、光照射前の紫外線感知部材のシアンの光学濃度の値をC1、光照射2時間経過後の紫外線感知部材のシアンの光学濃度の値をC2、光照射前の紫外線感知部材のイエローの光学濃度の値をY1、2時間経過後の紫外線感知部材のイエローの光学濃度の値をY2、光照射前の紫外線感知部材のマゼンタの光学濃度の値をM1、2時間経過後の紫外線感知部材のマゼンタの光学濃度の値をM2とした際に、C1とC2との差、Y1とY2との差、及び、M1とM2との差を測定した。C1とC2との差、Y1とY2との差、及び、M1とM2との差光学濃度差のうち、最も大きい値を表2の「光学濃度差」欄に示す。
さらに、C1とC2との差、Y1とY2との差、及び、M1とM2との差光学濃度差のうち、最も大きい値を与えた色(シアン、イエロー又はマゼンタ)、について、紫外線照射後24時間経過後にも分光測色計Xライト(エックスライト社製)を用いて、光照射後の紫外線感知部材の光学濃度を測定し、以下の式により算出した光学濃度変化率を表2の「光学濃度変化率」欄に示す。
式(II)
光学濃度変化率(%)=[(照射24時間後の光学濃度)-(照射2時間後の光学濃度)]/[(照射2時間後の光学濃度)-(照射前の光学濃度)]×100
各実施例で作製された紫外線感知部材に対して、積算照度3mJ/cm2になるように距離と時間を調整して光を照射した際に、紫外線感知部材の色味の変化により判定できるか否かを評価した。
AA:非常に容易に判定できる
A :容易に判定できる
B :容易に判定できない
実施例と比較例1及び参考例1との対比から、紫外線感知部材が増感剤を有する場合、判定が容易にできることが確認された。
さらに、実施例1~3と比較例1の比較から、本発明の実施例1~3は照射から2時間経過後の発色濃度と照射から24時間経過後の発色濃度の差が小さく好ましいことがわかる。
実施例1の紫外線検査感知部材をヘレウス(株)社製高圧水銀灯を用いて、313nmのバンドパスフィルタを介し、波長313nmの光の照射量が9mJ/cm2となるように紫外線を照射した。分光測色計Xライト(エックスライト社製)を用いて、イエローの光学濃度、マゼンタの光学濃度、及び、シアンの光学濃度の値をそれぞれ測定し、光照射前の紫外線感知部材のシアンの光学濃度の値をC4、光照射2時間後の紫外線感知部材のシアンの光学濃度の値をC5、光照射前の紫外線感知部材のイエローの光学濃度の値をY4、光照射2時間後の紫外線感知部材のイエローの光学濃度の値をY5、光照射前の紫外線感知部材のマゼンタの光学濃度の値をM4、光照射2時間後の紫外線感知部材のマゼンタの光学濃度の値をM5、を測定したところ、C4とC5との差、Y4とY5との差、及び、M4とM5との差のすべてが0.15以下であった。
12 支持体
14 紫外線感知層
Claims (9)
- 吸収極大波長を200~230nmの範囲に有する増感剤と、光活性剤と、発色剤とを含む紫外線感知部材。
- 前記増感剤がナフタレン構造を有する、請求項1に記載の紫外線感知部材。
- 前記光活性剤がハロメチル-s-トリアジン構造を有する、請求項1又は2に記載の紫外線感知部材。
- 紫外線感知部材であって、
KrClエキシマランプを光源として用い、波長230~300nmの光を実質的に遮光するフィルタを介して、波長222nmの光の照射量が3mJ/cm2となるまで前記紫外線感知部材に光を照射した後、分光測色計Xライト(エックスライト社製)を用いて、光照射前の前記紫外線感知部材及び光照射後の前記紫外線感知部材のイエローの光学濃度、マゼンタの光学濃度、及び、シアンの光学濃度の値をそれぞれ測定し、光照射前の前記紫外線感知部材のシアンの光学濃度の値をC1、光照射2時間後の前記紫外線感知部材のシアンの光学濃度の値をC2、光照射24時間後の前記紫外線感知部材のシアンの光学濃度の値をC3、光照射前の前記紫外線感知部材のイエローの光学濃度の値をY1、光照射2時間後の前記紫外線感知部材のイエローの光学濃度の値をY2、光照射24時間後の前記紫外線感知部材のイエローの光学濃度の値をY3、光照射前の前記紫外線感知部材のマゼンタの光学濃度の値をM1、光照射2時間後の前記紫外線感知部材のマゼンタの光学濃度の値をM2、光照射24時間後の前記紫外線感知部材のマゼンタの光学濃度の値をM3、とした際に、C1とC2との差、Y1とY2との差、及び、M1とM2との差のいずれか一つが0.20以上であり、前記C1とC2との差、前記Y1とY2との差、及び、前記M1とM2との差のうち、最大の差を与える色の下記式(II)で表される光学濃度変化率が-50%以上50%以下である、紫外線感知部材。
式(II)
光学濃度変化率(%)=[(照射24時間後の光学濃度)-(照射2時間後の光学濃度)]/[(照射2時間後の光学濃度)-(照射前の光学濃度)]×100 - 前記C1とC2との差、前記Y1とY2との差、前記M1とM2との差、及び前記光学濃度変化率が請求項5の要件を満たす、請求項1~4のいずれか1項に記載の紫外線感知部材。
- シート状である、請求項1~6のいずれか1項に記載の紫外線感知部材。
- 請求項1~7のいずれか1項に記載の紫外線感知部材を含む、紫外線感知キット。
- 請求項1~7のいずれか1項に記載の紫外線感知部材を含み、
波長313nmの光の照射量が9mJ/cm2となるまで前記紫外線感知部材に光を照射した後、分光測色計Xライト(エックスライト社製)を用いて、光照射前の前記紫外線感知部材及び光照射後の前記紫外線感知部材のイエローの光学濃度、マゼンタの光学濃度、及び、シアンの光学濃度の値をそれぞれ測定し、光照射前の前記紫外線感知部材のシアンの光学濃度の値をC4、光照射2時間後の前記紫外線感知部材のシアンの光学濃度の値をC5、光照射前の前記紫外線感知部材のイエローの光学濃度の値をY4、光照射2時間後の前記紫外線感知部材のイエローの光学濃度の値をY5、光照射前の前記紫外線感知部材のマゼンタの光学濃度の値をM4、光照射2時間後の前記紫外線感知部材のマゼンタの光学濃度の値をM5、とした際に、C4とC5との差、Y4とY5との差、及び、M4とM5との差のすべてが0.15以下である、紫外線感知キット。
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JPS6089352A (ja) * | 1983-10-24 | 1985-05-20 | 三井東圧化学株式会社 | 紫外線変色シ−ト |
JP2004045037A (ja) * | 2001-03-05 | 2004-02-12 | Masahiro Irie | カラー線量計及びフォトクロミック化合物 |
JP2008506826A (ja) * | 2004-07-21 | 2008-03-06 | チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド | 光活性化方法及び逆転した2段階工程による触媒の使用 |
JP2010501655A (ja) * | 2006-08-24 | 2010-01-21 | チバ ホールディング インコーポレーテッド | Uv線量インジケータ |
JP2011519411A (ja) * | 2008-02-21 | 2011-07-07 | ビーエーエスエフ ソシエタス・ヨーロピア | Uv線量インジケータフィルム |
WO2016017701A1 (ja) * | 2014-07-31 | 2016-02-04 | 富士フイルム株式会社 | 紫外線感知シート、紫外線感知セットおよび紫外線感知方法 |
JP2018517488A (ja) * | 2015-06-03 | 2018-07-05 | ザ トラスティーズ オブ コロンビア ユニバーシティ イン ザ シティ オブ ニューヨーク | 選択的にウイルスに影響を及ぼすかおよび/またはそれを死滅させるための装置、方法およびシステム |
JP2019187727A (ja) * | 2018-04-24 | 2019-10-31 | ウシオ電機株式会社 | 乾燥殺菌装置および乾燥殺菌方法 |
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