Active hydrogen-containing organic compound scavengers, compositions thereof and their uses

Abstract

This invention provides a material for efficiently capturing active hydrogen-containing organic compounds such as alcohols. It utilizes an active hydrogen-containing organic compound capture agent comprising an isocyanate compound (which may be a single compound or a mixture of multiple compounds, where n represents the average value of the mixture) represented by formula (1) below, with a bromine content of 38 wt% to 78 wt%. In formula (1), R... 1 and R 2 Each can be independently represented by either a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. R 3 Each of the following can be independently represented: a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a bromine atom. m represents at least one atom selected from 0, 1, 2, and 3. n represents a real number greater than 0.

Description

Technical Field

[0001] This invention relates to scavenging agents, compositions, and uses thereof for capturing organic compounds containing active hydrogen. Background Technology

[0002] Volatile organic compound (VOC) capture agents and technologies are widely used in various aspects of daily life. For example, technologies for capturing amine compounds and aromatic hydrocarbons, which are VOCs contributing to Sick House syndrome, include techniques utilizing the inclusion effect of cyclodextrin compounds and techniques utilizing the neutralization effect of amino acids. In these capture technologies, the agent is sprayed into the space to capture VOCs floating in the air, thereby purifying the indoor space. Furthermore, porous inorganic materials are known to adsorb various VOCs; for example, deodorizing filters containing activated carbon have been developed as capture agents.

[0003] On the other hand, with increased awareness of chemical safety, alcohol-based VOCs have recently received new attention. For example, in Japan, two alcohol chemicals (2-ethyl-1-hexanol and Texanol ester alcohol) have been added to the list of new causes of musty odors. These alcohol compounds are known to be generated by the deterioration of building material resins and water-based paint components, but effective capture technologies have not been established. In addition, during the proliferation and metabolism of microorganisms, alcohol-based VOCs such as 2-methyl-1-butanol and 1-pentanol are sometimes produced, becoming a cause of so-called musty odors (Non-Patent Literature 1).

[0004] Existing technical documents

[0005] Non-patent literature

[0006] Non-patent literature 1: Journal of the Environmental Society for Odor and Fragrance, 2003, Vol. 43, pp. 184-190 Summary of the Invention

[0007] The technical problem that the invention aims to solve

[0008] The object of the present invention is to provide a capture agent for active hydrogen-containing organic compounds such as alcohols that are difficult to capture in the prior art.

[0009] Means for solving technical problems

[0010] In order to solve the above-mentioned problems, the inventors conducted in-depth research and found that the following capturing agent or the following composition can capture organic compounds containing active hydrogen, such as alcohols, which were previously difficult to capture, thereby completing the present invention.

[0011] That is, the present invention contains the following [1] to

[18] . [1]

[0013] An active hydrogen-containing organic compound scavenger, comprising: an isocyanate compound represented by the following formula (1) with a bromine content of 38wt% to 78wt% (which may be a single compound or a mixture of multiple compounds; in the case of a mixture, n represents the average value of the mixture):

[0014] [Chemistry 1]

[0015]

[0016] In equation (1), R 1 and R 2 Each can be independently represented by either a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; R 3 Each of the following can be independently represented: a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a bromine atom; m represents at least one of the following: 0, 1, 2, and 3; n represents a real number greater than 0. [2]

[0018] According to the active hydrogen-containing organic compound scavenger described above [1], the isocyanate compound represented by the above formula (1) (which may be a single compound or a mixture of multiple compounds; in the case of a mixture, n represents the average value of the mixture) is the isocyanate compound represented by the following formula (1a) (which may be a single compound or a mixture of multiple compounds; in the case of a mixture, n represents the average value of the mixture):

[0019] [Chemistry 2]

[0020]

[0021] In equation (1a), R 1 and R 2 Each can be independently represented by either a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; R 3 Each of the following can be independently represented: a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a bromine atom; m represents at least one of the following: 0, 1, 2, and 3; n represents a real number greater than 0. [3]

[0023] According to the active hydrogen-containing organic compound scavenger described above [1], the isocyanate compound represented by the above formula (1) (which may be a single compound or a mixture of multiple compounds; in the case of a mixture, n represents the average value of the mixture) is the isocyanate compound represented by the following formula (1b) (which may be a single compound or a mixture of multiple compounds; in the case of a mixture, n represents the average value of the mixture):

[0024] [Chemistry 3]

[0025]

[0026] In equation (1b), R 1 and R 2 Each can be independently represented by either a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; R 3 Each of the following can be used to independently represent a hydrogen atom, an alkyl group with 1 to 4 carbon atoms, or a bromine atom; n represents a real number greater than 0. [4]

[0028] The active hydrogen-containing organic compound scavenger according to any one of [1] to [3] above, wherein the bromine content is 50wt% to 78wt%. [5]

[0030] According to any one of the above [1] to [4], the active hydrogen-containing organic compound scavenger, wherein the above R 1 and R 2 Each can be a hydrogen atom or a methyl group, independently. [6]

[0032] According to any one of the above [1] to [5], the active hydrogen-containing organic compound scavenger, wherein the above R 1 and R 2 It is a hydrogen atom. [7]

[0034] According to any one of [1] to [6] above, the active hydrogen-containing organic compound scavenger, wherein, in the above formula (1), R 3 Each can be a hydrogen atom or a bromine atom, independently. [8]

[0036] According to any one of [1] to [7] above, the active hydrogen-containing organic compound scavenger, wherein n is a real number from 0 to 3. [9]

[0038] A method for capturing a compound, wherein the compound is contacted with an active hydrogen-containing organic compound capturing agent as described in any one of [1] to [8] above to capture the compound; wherein the compound is at least one compound selected from alcohol compounds, thiols, amine compounds, phenolic compounds and carboxylic acid compounds.

[10]

[0040] A composition comprising: an isocyanate compound (which may be a single compound or a mixture of multiple compounds; in the case of a mixture, n represents the average value of the mixture) represented by formula (1) in an bromine content of 38 wt% to 78 wt%, and a support:

[0041] [Chemistry 4]

[0042]

[0043] In equation (1), R 1 and R 2 Each can be independently represented by either a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; R 3 Each of the following can be independently represented: a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a bromine atom; m represents at least one of the following: 0, 1, 2, and 3; n represents a real number greater than 0.

[11]

[0045] According to the composition described above

[10] , wherein the isocyanate compound represented by the above formula (1) (which may be a single compound or a mixture of multiple compounds; in the case of a mixture, n represents the average value of the mixture) is the isocyanate compound represented by the following formula (1a) (which may be a single compound or a mixture of multiple compounds; in the case of a mixture, n represents the average value of the mixture):

[0046] [Chemistry 5]

[0047]

[0048] In equation (1a), R 1 and R 2 Each can be independently represented by either a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; R 3 Each of the following can be independently represented: a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a bromine atom; m represents at least one of the following: 0, 1, 2, and 3; n represents a real number greater than 0.

[12]

[0050] According to the composition described in

[10] , wherein the isocyanate compound represented by the above formula (1) (which may be a single compound or a mixture of multiple compounds; in the case of a mixture, n represents the average value of the mixture) is the isocyanate compound represented by the following formula (1b) (which may be a single compound or a mixture of multiple compounds; in the case of a mixture, n represents the average value of the mixture):

[0051] [Chemistry 6]

[0052]

[0053] In equation (1b), R 1 and R 2 Each can be independently represented by either a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; R 3Each of the following can be represented independently: a hydrogen atom, an alkyl group with 1 to 4 carbon atoms, or a bromine atom; each of the following can be represented independently: n represents a real number greater than 0.

[13]

[0055] The composition according to any one of

[10] to

[12] above, wherein the above R 3 Each can be a hydrogen atom or a bromine atom, independently.

[14]

[0057] The composition according to any one of

[10] to

[13] , wherein the above-mentioned isocyanate compound is loaded on the carrier.

[15]

[0059] The composition according to any one of

[10] to

[14] above, wherein the loading of the isocyanate compound is 0.1 parts by weight to 60 parts by weight relative to 100 parts by weight of the carrier.

[16]

[0061] The composition according to any one of

[10] to

[15] above, wherein the carrier is one or more carriers selected from activated carbon, activated clay, diatomaceous earth, porous resin, nonwoven fabric, mesoporous silica, silica gel, aluminosilicate, hydrotalcite, zeolite, activated alumina, titanium dioxide, magnesium oxide and zirconium oxide.

[17]

[0063] An active hydrogen organic compound scavenger comprising any one of the compositions described in

[10] to

[16] above.

[18]

[0065] A method for capturing the compound, wherein the compound is brought into contact with the composition described in any one of

[10] to

[16] above to capture the compound; the compound is at least one compound selected from alcohol compounds, thiols, amine compounds, phenolic compounds and carboxylic acid compounds.

[0066] Invention Effects

[0067] Compared with conventionally known capture technologies, the capture agents or compositions of the present invention can capture active hydrogen-containing organic compounds such as alcohols with high selectivity.

[0068] The trapping agent or composition of the present invention captures active hydrogen-containing organic compounds through a chemical reaction with isocyanate groups. Therefore, the temporarily captured active hydrogen-containing organic compounds are almost never released again, eliminating concerns about re-polluting the environment. Furthermore, due to its high water resistance, it continuously maintains its ability to capture active hydrogen-containing organic compounds in the living environment. Detailed Implementation

[0069] The present invention will now be described in detail.

[0070] This invention relates to the above-mentioned trapping agents or compositions, and their uses. It should be noted that wt% refers to weight percentage, and A to B refers to A or more and B or less (the same applies hereinafter).

[0071] In equations (1), (1a), and (1b) above, R 3 Each can be independently represented by a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a bromine atom.

[0072] As R 3 The alkyl group having 1 to 4 carbon atoms is not particularly limited, and examples include methyl, ethyl, propyl, isopropyl, cyclopropyl, butyl, isobutyl, sec-butyl or tert-butyl.

[0073] From the viewpoint that the isocyanate compounds represented by the above formulas (1), (1a) or (1b) have excellent production rates, R 3 Preferably, each is independently composed of a hydrogen atom, a methyl atom, or a bromine atom; more preferably, each is independently composed of a hydrogen atom or a bromine atom.

[0074] It should be noted that R 3 When the atoms are hydrogen atoms or bromine atoms, respectively, the above formula (1) can be replaced by the following formula (1').

[0075] [Chemistry 7]

[0076]

[0077] In the above formula (1'), R 1 and R 2 Each of the following can be independently represented as an alkyl group having 1 to 4 hydrogen atoms or carbon atoms. m represents at least one of the following: 0, 1, 2, and 3. n represents a real number greater than or equal to 0. -Br represents a bromine atom, and k represents a real number in the range of 1 to [5–m+m×(3×n+1)] (i.e., a real number in the range of 1 to [5+3×m×n]), representing the state in which bromine atoms equivalent to wt% (k) of Y are bonded to aromatic ring carbon atoms.

[0078] In the above formula (1′), -Br represents a bromine atom bonded to an aromatic ring, but this does not mean there is only one bromine atom, but rather refers to the number of bromine atoms bonded to satisfy Y wt% as described later. Y wt% represents the bromine content in the isocyanate compound (which may be a single compound or a mixture of multiple compounds) represented by the above formula (1′), and as mentioned above, it is preferably 38wt% to 78wt%.

[0079] Furthermore, from the perspective of excellent capture performance of active hydrogen-containing organic compounds, the isocyanate compound represented by the above formula (1) (which may be a single compound or a mixture of multiple compounds, and in the case of a mixture, n represents the average value of the mixture) is preferably the isocyanate compound represented by the above formula (1a) (which may be a single compound or a mixture of multiple compounds, and in the case of a mixture, n represents the average value of the mixture), and more preferably the isocyanate compound represented by the above formula (1b) (which may be a single compound or a mixture of multiple compounds, and in the case of a mixture, n represents the average value of the mixture).

[0080] In the above equations (1), (1'), (1a) and (1b), R 1 and R 2 Each can be independently represented as an alkyl group having 1 to 4 hydrogen atoms or carbon atoms.

[0081] As R 1 and R 2 The alkyl group having 1 to 4 carbon atoms is not particularly limited, and examples include methyl, ethyl, propyl, isopropyl, cyclopropyl, butyl, isobutyl, sec-butyl or tert-butyl.

[0082] From the perspective of the superior productivity of the aforementioned isocyanate compounds, R 1 and R 2 Preferably, each is a hydrogen atom or a methyl group, and more preferably, a hydrogen atom.

[0083] In formulas (1), (1'), (1a), and (1b), n represents a real number greater than or equal to 0. Regarding this n, from the viewpoint of achieving excellent productivity of the isocyanate compounds represented by formulas (1), (1'), (1a), or (1b), it is preferably a real number greater than 0, more preferably a real number greater than 0.1, and even more preferably a real number greater than 0.3. Furthermore, regarding this n, from the viewpoint of achieving excellent productivity of the isocyanate compounds shown by formulas (1), (1'), (1a), or (1b), it is preferably a real number less than or equal to 10, more preferably a real number less than or equal to 6, even more preferably a real number less than or equal to 3, and even more preferably a real number less than or equal to 2.

[0084] Regarding n, from the perspective of the excellent capture performance of the active hydrogen-containing organic compounds in the capture agent or composition of the present invention, it is preferably a real number of 0 to 10, more preferably a real number of 0 to 6, more preferably a real number of more than 0 and less than 6, more preferably a real number of 0.1 to 3, and even more preferably a real number of more than 0.3 and less than 2. Furthermore, from the perspective of the excellent productivity of the isocyanate compounds represented by formula (1), (1'), (1a) or (1b), it is more preferably a real number of 0 to 3, and even more preferably a real number of 0 to 2.

[0085] It should be noted that when n is 0, it means that the group enclosed by [ ]n in equations (1), (1'), (1a) or (1b) does not exist.

[0086] In formulas (1), (1') and (1a), m represents at least one selected from 0, 1, 2 and 3. That is, the isocyanate represented by the above formulas (1), (1') or (1a) can be, for example, a single substance with m=0, or a mixture of components containing m=0, m=1, m=2 and m=3.

[0087] Regarding m, from the viewpoint of the superior productivity of the isocyanate compound represented by formula (1), (1') or (1a), it is preferably selected from at least one of 0, 1 and 2, more preferably selected from at least one of 0 and 1, and even more preferably 0 or 1.

[0088] It should be noted that when m is 0, it means that the group surrounded by [ ]m in formula (1), (1') or (1a) does not exist. When m is 3, it means that there are 3 groups surrounded by [ ]m and each is bonded to the benzene ring of the basic group.

[0089] When m is 2 or 3, there are two or three n in the general formula, but the range of n can be clearly expressed by specifying its average value.

[0090] Here, for example, isocyanates with m=0 (i.e., n=0) can be referred to as mononuclear, isocyanates with m=1 and n=1 can be referred to as binuclear, isocyanates with m=1 and n=2 can be referred to as trinuclear, isocyanates with m=1 and n=3 or isocyanates with m=3 and three n=1 (average) can be referred to as tetranuclear, and isocyanates with m=1 and n=4 or isocyanates with m=3 and n=1.33 (average value represented by 4 / 3) can be referred to as pentanuclear.

[0091] There are no particular limitations on the general formulas from mononuclear to pentanuclear included in formula (1), as illustrated below.

[0092] [Chemistry 8]

[0093]

[0094] In the above formulas, R 1 R 2 and R 3 The definition and preferred range are as described above.

[0095] It should be noted that the isocyanate compounds of the present invention can be a single compound or a mixture of isocyanate compounds represented by formulas (1), (1'), (1a), or (1b) with different combinations of m and n. It should also be noted that when the isocyanate compounds represented by formulas (1), (1'), (1a), or (1b) are mixtures, n is sometimes not an integer but a real number because it is treated as an average value derived from the components of the mixture.

[0096] That is, the isocyanate compound of the present invention may be a mononuclear compound, a binuclear compound, a trinuclear compound, a mixture of mononuclear and binuclear compounds, a mixture of mononuclear, binuclear and trinuclear compounds, a mixture of mononuclear, binuclear and tetranuclear compounds, or a mixture of more than four nuclei, and is not limited thereto.

[0097] It should be noted that when the isocyanate compound represented by the above formulas (1), (1'), (1a), or (1b) is a mixture of multiple nuclei, the bromine content (equivalent to Y wt% in formula (1')) is preferably such that each of the multiple nuclei meets a specified range, but it is not necessary for each of the multiple nuclei to meet the specified range individually; it is sufficient that the mixture as a whole meets the specified range. That is, for example, the compound of the present invention can be manufactured by mixing a binary nucleus with a bromine content below a specified lower limit and a trinucleus with a bromine content above a specified upper limit at a ratio in which the bromine content falls within a specified range.

[0098] It should be noted that the isocyanate compounds represented by the above formulas (1), (1'), (1a) or (1b) are preferably mononuclear, dinuclear, trinuclear, tetranuclear, or mixtures of multiple nucleosomes, which have excellent supply stability. There is no particular limitation on the presence ratio of each nucleosome in the case of a mixture of multiple nucleosomes, but it is preferred that the mononuclear content is 0% to 20%, the dinuclear content is 10% to 99%, the trinuclear content is 5% to 60%, and the tetranuclear content or above is 0% to 30%.

[0099] Here, the presence ratio [%] of each of the above nuclei represents the GPC area %. The conditions for determining the GPC area % are as follows.

[0100] A GPC assay apparatus, HLC-8320GPC, manufactured by Tosoh Corporation, was used. Columns equipped with Tosoh Corporation's TSKgel guardcolumn SuperAW-H, TSKgel SuperAW2500, TSKgel SuperAW2500, TSKgel SuperAW3000, and TSKgel SuperAW3000 columns were used in series at a temperature of 40°C. Tetrahydrofuran (THF) was used as the eluent at a flow rate of 0.6 mL / min, and a UV-Vis spectrophotometer set to 254 nm was used. Data processing was performed using a Tosoh Corporation GPC-8020 model II version 4.10. The sample was prepared by dissolving 0.1 g of the sample in 10 mL of THF and filtering it through a microfilter. μ L sample. From the obtained chromatogram, the content of mononuclear, dinuclear, trinuclear, tetranuclear, and pentanuclear or higher nuclei can be calculated.

[0101] When the isocyanate compound represented by the above formulas (1), (1'), (1a) or (1b) is a mixture of multiple compounds (a mixture of multiple nuclei), the above n represents the average value (real number) of the mixture, which can be calculated using the value of the presence ratio of each nuclei [GPC area %].

[0102] For example, when the presence rate of binary nuclei (m=1, n=1) is 50 [GPC area%] and the presence rate of trinuclei (m=1, n=2) is 50 [GPC area%], the average value of n is calculated as (1×0.5+2×0.5)=1.5.

[0103] In equation (1′), k represents a real number in the range of 1 to [5-m+m×(3×n+1)] (i.e., a real number in the range of 1 to [5+3×m×n]). For example, when m=0 (i.e. n=0), k represents a real number in the range of 1 to 5; when m=1 and n=1, k represents a real number in the range of 1 to 8; and when m=1 and n=2, k represents a real number in the range of 1 to 11.

[0104] The value of k represents a real number because n is a real number, and the number of bromine atoms added during the manufacture of the isocyanate compounds represented by equations (1), (1'), (1a), or (1b) is not necessarily uniform throughout the molecule. For example, in the case where m = n = 0 and there is one bromine atom added, and m = n = 0 and there are two bromine atoms added, in a 50:50 molar ratio, k represents a real number of approximately 1.5.

[0105] The bromine content (Y wt% in formula (1')) in the isocyanate compounds represented by formulas (1), (1'), (1a), or (1b) is characterized by 38 wt% to 78 wt%. Regarding this bromine content, from the viewpoint of improving the capture selectivity of active hydrogen-containing organic compounds such as alcohols, it is preferably 45 wt% to 78 wt%, more preferably 50 wt% to 78 wt%, and even more preferably 55 wt% to 78 wt%. It should be noted that the bromine content (Y wt% in formula (1')) in the isocyanate compounds represented by formulas (1), (1'), (1a), or (1b) represents the result determined by the oxygen flask combustion-IC method.

[0106] There is a certain correlation between the bromine content (Y wt% in formula (1') and the real number k mentioned above. It should be noted that the range of k mentioned above represents the maximum range of bromine atoms that can be used by the isocyanate compound represented by formula (1').

[0107] The isocyanate compounds represented by formulas (1), (1'), (1a), or (1b) can be manufactured by isocyanating the corresponding amine compound. For example, the manufacture of aromatic isocyanate compounds containing bromine atoms is disclosed in patent document (GB971168).

[0108] There are no particular limitations on the isocyanate compound represented by formula (1), (1a) or (1b) (which may be a single compound or a mixture of multiple compounds), for example, it can be manufactured by converting the amino group of the amine compound into an isocyanate group by using an amine compound represented by formula (2), (2a) or (2b) below as a precursor (which may be a single compound or a mixture of multiple compounds, where n represents the average value of the mixture).

[0109] [Chemistry 9]

[0110]

[0111] In equation (2), R 1 and R 2 Each can be independently represented by either a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. R 3 Each of the following can be independently represented: a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a bromine atom. m represents at least one atom selected from 0, 1, 2, and 3. n represents a real number greater than 0.

[0112] [Chemistry 10]

[0113]

[0114] In equation (2a), R 1 and R2 Each can be independently represented by either a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. R 3 Each of the following can be independently represented: a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a bromine atom. m represents at least one atom selected from 0, 1, 2, and 3. n represents a real number greater than 0.

[0115] [Chemistry 11]

[0116]

[0117] In equation (2b), R 1 and R 2 Each can be independently represented by either a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. R 3 Each of the following can be used independently to represent a hydrogen atom, an alkyl group with 1 to 4 carbon atoms, or a bromine atom. n represents a real number greater than 0.

[0118] Regarding R in equations (2), (2a), or (2b) above... 1 R 2 R 3 The definitions of , n, and m, and the preferred ranges, are related to R in the above equation (1). 1 R 2 R 3 The definitions of n and m, as well as the meaning of the preferred range, are the same.

[0119] It is difficult to generalize about the bromine content (wt%) in general formulas (2), (2a) or (2b), but it is preferred that they theoretically meet the requirements of the bromine content (wt%) in formulas (1), (1a) or (1b).

[0120] The amine compounds represented by formulas (2), (2a) or (2b) above are not particularly limited, and examples include bromides of aniline, bromides of 4,4'-methylenediphenylamine, bromides of 2,2'-bis(4-aminophenyl)propane, bromides of polymers of aniline and formalin, or bromides of polymers of aniline and acetone.

[0121] Regarding the amine compounds represented by formulas (2), (2a), or (2b) above, commercially available products can be used directly, or they can be manufactured by brominating aniline, 4,4'-methylenediphenylamine, 2,2'-bis(4-aminophenyl)propane, polymers of aniline and formalin, or polymers of aniline and acetone using generally known methods. Alternatively, polymers of brominated aniline and formalin, or polymers of brominated aniline and acetone, can also be manufactured.

[0122] Next, an active hydrogen-containing organic compound scavenger or composition containing an isocyanate compound represented by formula (1), (1'), (1a) or (1b) will be described.

[0123] Isocyanate compounds such as diphenylmethane diisocyanate (MDI) and toluene diisocyanate (TDI) (isocyanate compounds different from those represented by formulas (1), (1'), (1a), or (1b) above) are typically used as raw materials for the manufacture of polyurethane. They utilize the fundamental property of isocyanate groups reacting with nucleophilic functional groups (groups with active hydrogen, such as hydroxyl and amino groups). Conventional isocyanate compounds are highly reactive, reacting with moisture in the air even at temperatures near room temperature (15°C–40°C), resulting in low atmospheric storage stability.

[0124] Compared to existing technologies, the isocyanate compounds represented by formulas (1), (1'), (1a), or (1b) exhibit high water resistance and react very slowly with water in a temperature environment near room temperature (15°C to 40°C). On the other hand, they react with active hydrogen-containing organic compounds such as alcohols in a temperature environment near room temperature (15°C to 40°C). That is, the isocyanate compounds represented by formulas (1), (1'), (1a), or (1b) react with active hydrogen-containing organic compounds such as alcohols in a highly selective manner in the presence of water and active hydrogen-containing organic compounds such as alcohols. By making good use of this feature, an active hydrogen organic compound scavenger containing an isocyanate compound represented by formula (1), (1'), (1a) or (1b) above, or a composition containing an isocyanate compound and a carrier represented by formula (1), (1'), (1a) or (1b) above, can be used as a scavenger for active hydrogen organic compounds such as alcohol compounds that have a sustained effect in the living environment.

[0125] The aforementioned active hydrogen-containing organic compounds that are the targets of capture are not particularly limited, and examples include alcohols, thiols, amines, phenols, or carboxylic acids. More specifically, examples include methanol, ethanol, 1-propanol, 2-methyl-1-propanol, 1-butanol, 2-methyl-1-butanol, 1-pentanol, 1-hexanol, 2-ethyl-1-hexanol, 1-heptanol, 1-octanol, 1-nonanol, 1-decanol, 1-undecanol, 1-dodecanol, 2-methoxyethanol, 2-ethoxyethanol, and other primary alcohols; 2-propanol, 2-butanol, 2-pentanol, etc. Secondary alcohols such as 3-pentanol, 2-hexanol, cyclohexanol, and 2,2,4-trimethylpentane-1,3-diol monoisobutyrate; tertiary alcohols such as tert-butanol, 2-methyl-2-pentanol, 3-methyl-3-pentanol, terpineol, and linalool; polyols such as 1,2-ethylene glycol, 1,4-butanediol, and glycerol; amines such as methylamine, dimethylamine, ethylamine, diethylamine, butylamine, hexylamine, octylamine, ethanolamine, diethanolamine, ethylenediamine, diethylenetriamine, and hexamethylenediamine; thiols such as methylthiol, ethylthiol, propylthiol, butylthiol, hexylthiol, and thiophenol; carboxylic acids such as formic acid, acetic acid, and propionic acid; and phenolic compounds such as phenol and salicylic acid.

[0126] Considering the difficulty in capturing these organic compounds in the prior art and the ability to obtain the significant heterogeneous effects of the present invention, alcohol compounds or carboxylic acid compounds are preferred among these active hydrogen-containing organic compounds.

[0127] The active hydrogen-containing organic compound that is the target of capture can be in any of the following states: solid, liquid, or gas. However, in order to efficiently capture the active hydrogen-containing organic compound, it is necessary to increase the contact frequency with the isocyanate compound represented by the above formulas (1), (1'), (1a), or (1b). Therefore, a liquid or gaseous state is preferred. The active hydrogen-containing organic compound that is the target of capture can be dissolved in a solvent. There are no particular limitations on the applicable solvent, and examples include aqueous solvents, hydrocarbon solvents, halogen solvents, aromatic solvents, and ether solvents.

[0128] The isocyanate compounds represented by formulas (1), (1'), (1a), or (1b) are liquid or solid at room temperature. The isocyanate compounds represented by formulas (1), (1'), (1a), or (1b) can be used as scavenging agents in a liquid or solid state, or the solid isocyanate compounds represented by formulas (1), (1'), (1a), or (1b) can be pulverized into powder using a mortar and pestle, and used in powder form, or the powder can be compacted into a block form for use. These substances are all active hydrogen-containing organic compound scavenging agents of the present invention.

[0129] The composition (hereinafter also referred to as "the composition of the present invention") containing an isocyanate compound with a bromine content of 38 wt% to 78 wt% and a support, as represented by formula (1) above, also functions as an active hydrogen-containing organic compound scavenger for the purposes of the present invention. In this case, the isocyanate compound represented by formula (1) above is preferably loaded onto the support described above.

[0130] Regarding the composition of the present invention described above, the isocyanate compound with a bromine content of 38wt% to 78wt% as represented by formula (1) is preferably an isocyanate compound with a bromine content (Y wt%) of 38wt% to 78wt% as represented by formula (1'), more preferably an isocyanate compound with a bromine content of 38wt% to 78wt% as represented by formula (1a), and even more preferably an isocyanate compound with a bromine content of 38wt% to 78wt% as represented by formula (1b).

[0131] It should be noted that, in the compositions of the present invention described above, from the viewpoint of improving the capture selectivity of active hydrogen-containing organic compounds such as alcohols, the bromine content in the isocyanate compounds represented by formulas (1), (1'), (1a), or (1b) is preferably 45 wt% to 78 wt%, preferably 50 wt% to 78 wt%, and more preferably 55 wt% to 78 wt%. It should be noted that the bromine content (Y wt% in formula (1')) in the present invention is determined by the oxygen flask combustion-IC method.

[0132] Furthermore, there are no particular limitations on the aforementioned carriers; examples include activated carbon, activated clay, diatomaceous earth, porous resin, nonwoven fabric, mesoporous silica, silica gel, aluminosilicate, hydrotalcite, zeolite, activated alumina, titanium dioxide, magnesium oxide, or zirconium oxide. Among these carriers, considering the superior performance of the capture agent, activated carbon, nonwoven fabric, silica gel, or hydrotalcite are preferred, with silica gel or hydrotalcite being more preferred.

[0133] When an isocyanate compound represented by formula (1), (1'), (1a), or (1b) is loaded onto a support, the mixture is prepared by dissolving the corresponding isocyanate compound in an organic solvent, mixing it with the support, and then performing an organic solvent removal operation. In this case, an organic solvent free of active hydrogen is preferably used as the organic solvent, and there are no particular limitations; examples include hexane, dichloromethane, chloroform, acetone, tetrahydrofuran, dioxane, benzene, chlorobenzene, toluene, or xylene.

[0134] The compositions of the present invention described above may further contain styrene-butadiene rubber, polyvinylidene fluoride, polytetrafluoroethylene, sepiolite, attapulgite and other clays, sodium silicate, silica sol and other binders.

[0135] There is no particular limitation on the loading amount when the isocyanate compound represented by formula (1), (1'), (1a) or (1b) above is loaded on the support. For example, it is preferable to be 0.1 parts to 60 parts by weight relative to 100 parts by weight of the support, more preferably 0.5 parts to 40 parts by weight relative to 100 parts by weight of the support, and even more preferably 1 part to 25 parts by weight relative to 100 parts by weight of the support.

[0136] As described above, the isocyanate compounds represented by formulas (1), (1'), (1a), or (1b) can be used as scavengers in powder or block form, or in a state containing a support or loaded on a support. From the viewpoint of improving the scavenging effect of organic compounds containing active hydrogen, it is preferable to use them as scavengers loaded on supports such as silica gel, zeolite, alumina, hydrotalcite, or activated carbon.

[0137] In this invention, the temperature at which the active hydrogen-containing organic compound capture agent or the composition of this invention captures active hydrogen-containing organic compounds is not particularly limited, as long as it is in the range of 0°C to 150°C. From the viewpoint of selectively capturing active hydrogen-containing organic compounds such as alcohols, the range of 10°C to 100°C is preferred, and the range of 20°C to 70°C is more preferred.

[0138] The active hydrogen-containing organic compound scavenger or the composition of the present invention described above can be used in a method for capturing active hydrogen-containing organic compounds. Specifically, the active hydrogen-containing organic compound scavenger or the composition of the present invention described above can be contacted with at least one compound selected from alcohols, thiols, amines, phenols, and carboxylic acids to capture the compound.

[0139] It should be noted that these target compounds (including active hydrogen organic compounds) are preferably substances generated in the natural or living environment, and their formation can be either anthropogenic or non-anthropogenic.

[0140] From the viewpoint that the capture of these target compounds (organic compounds containing active hydrogen) is difficult in the prior art and can achieve the significant heterogeneous effect of the present invention, alcohol compounds or carboxylic acid compounds are preferred among these target compounds. Attached Figure Description

[0141] Figure 1 : A schematic diagram of the device for evaluating the capture of active hydrogen-containing organic compounds used in the examples. Example

[0142] The present invention will now be described in detail through examples. However, the present invention is not limited thereto.

[0143] [GCMS Analysis]

[0144] Measurement device: HERACLES II electronic olfactory system manufactured by Alpha MOS Japan Co., Ltd.

[0145] Measurement conditions: Column = Agilent J&W GC column DB-5

[0146] Vaporization chamber temperature = 220℃

[0147] Temperature of the detection section = 260℃

[0148] Column temperature = 250℃

[0149] Heating rate = 1.5℃ / second

[0150] [FT-IR analysis]

[0151] Measurement apparatus: PerkinElmer, Frontier MIR / NIR

[0152] Measurement conditions: ATR method MIR mode

[0153] [Quantitative determination of bromine content]

[0154] Combustion method: Oxygen cylinder combustion method (based on ISO 7725-2020)

[0155] Measurement device: IC-2001 manufactured by Tosoh Corporation

[0156] Synthesis example 1

[0157] [Chemistry 12]

[0158]

[0159] 100 g of a 4,4'-methylenediphenylamine composition (nuclear distribution: 65% dimerization, 23% trinuclearization, 8% tetranuclearization, and 4% pentanuclearization or higher), 5.00 g of ferric chloride, and 700 mL of 1,2-dichloroethane were added to a 2 L separable flask. Next, 338 g of bromine was diluted with 300 mL of 1,2-dichloroethane and added dropwise to the flask over 1 hour with stirring. After the addition was complete, the internal temperature was raised to 50 °C, and the flask was allowed to cool naturally at room temperature while stirring for 1 hour. Unreacted bromine was then removed with a hydrazine aqueous solution, and the pH was confirmed to be alkaline. The mixture was then separated into a 1,2-dichloroethane layer and an aqueous layer. The 1,2-dichloroethane layer was added dropwise to methanol, resulting in the precipitation of a pale red solid. The solid was filtered, washed with methanol, and then dried to obtain 153 g of a pale red solid (brominated 4,4'-methylenediphenylamine composition). The bromine content of the solid was quantified using the oxygen flask combustion-IC method, and the result was 59.6% by weight.

[0160] Synthesis example 2

[0161] [Chemistry 13]

[0162]

[0163] Under a nitrogen atmosphere, 12.5 g of the pale red solid (brominated 4,4'-methylenediphenylamine composition) obtained in Synthesis Example 1 and 987.5 g of chlorobenzene were added to a 2 L separable flask equipped with a stirrer and heated to 130 °C. 13.4 g of hydrochloric acid gas was blown into the solution over 90 minutes to initiate a salt formation reaction. Then, 44 g of carbonyl chloride gas was blown in over 2 hours. The mixture was then aged at 125 °C for 2 hours, followed by bubbling with nitrogen to remove carbonyl chloride from the system. After confirming that no carbonyl chloride remained, the reaction solution was brought to room temperature, and insoluble components were removed by filtration. The filtrate was concentrated using an evaporator, and the concentrate was dried under forced air at 45°C to obtain 12.4 g of 4,4'-methylenebis(2,6-dibromo-isocyanate phenylene) (dinuclear) and a mixture of oligomers of the compound (including trinuclear, tetranuclear, and pentanuclear forms or more; hereinafter referred to as Compound of Synthetic Example 2) as a brown powder (yield 79%). The NCO content (mass of isocyanate groups relative to the total mass) was 14.5% by mass, and the bromine content was 54.3% by weight. As described later, Compound of Synthetic Example 2 can be used as a scavenger of active hydrogen-containing organic compounds of the present invention.

[0164] Synthesis example 3

[0165] Under a nitrogen atmosphere, 30.0 g of 4,4'-methylenebis(2-bromoaniline) (nucleoside distribution: dinuclear = 100%) and 1470.0 g of chlorobenzene were added to a two-part separable flask equipped with a stirrer, and the mixture was heated to 130 °C. A salt-forming reaction was initiated by bubbling 12.3 g of hydrochloric acid gas into the solution over 120 minutes. Then, 109.6 g of carbonyl chloride gas was bubbled over 6 hours. The carbonyl chloride in the system was then removed by bubbling with nitrogen. After confirming that no carbonyl chloride remained, the reaction solution was brought to room temperature, and insoluble components were removed by filtration. The filtrate was concentrated using an evaporator, and the concentrate was dried under forced-air drying at 45 °C to obtain 33.0 g of 4,4'-methylenebis(2-bromo-isocyanate phenylene) as a white powder (yield 96%) (hereinafter referred to as the compound of Synthesis Example 3). The NCO content (mass of isocyanate groups relative to the total mass) is 21.0% by mass, and the bromine content is 39.1% by weight. This compound of Synthetic Example 3, as described below, can be used as a hydrogen-containing organic compound scavenger of the present invention.

[0166] Synthesis example 4

[0167] 5.00 g of a 4,4'-methylenediphenylamine composition (nucleoside distribution: dimeric = 65%, trinucleic = 23%, tetranucleic = 8%, pentanucleic or higher = 4%), 0.25 g of ferric chloride, and 100 mL of methanol were added to a 300 mL three-necked flask. Next, 19.5 g of bromine was diluted with 25 mL of methanol and added dropwise to the previously prepared 300 mL three-necked flask over 1 hour with stirring. Subsequently, following the same procedure as in Synthesis Example 1, 12.0 g of a reddish-brown solid (brominated 4,4'-methylenediphenylamine composition) (hereinafter referred to as the compound of Synthesis Example 4) was obtained. The bromine content of the solid was quantified using the oxygen flask combustion-IC method, yielding 58.5% by weight.

[0168] Synthesis example 5

[0169] 10.0 g of 4,4'-methylenediphenylamine (nuclear distribution: dimerization = 100%), 0.50 g of ferric chloride, and 200 mL of methanol were added to a 300 mL three-necked flask. Next, 19.5 g of bromine was diluted with 25 mL of methanol and added dropwise to the 300 mL three-necked flask over 1 hour with stirring. Subsequently, following the same procedure as in Synthesis Example 1, 25.5 g of a beige solid (brominated 4,4'-methylenediphenylamine) (hereinafter referred to as the compound of Synthesis Example 5) was obtained. The bromine content of the solid was quantified using the oxygen flask combustion-IC method, yielding a result of 59.4% by weight.

[0170] Synthesis example 6

[0171] Under a nitrogen atmosphere, 39.8 g of Compound 5 (nucleosome distribution: dimerization = 100%) and 1150.0 g of o-chlorobenzene were added to a 2 L separable flask equipped with a stirrer, and the mixture was heated to 140 °C. 11.3 g of hydrochloric acid gas was blown into the solution over 120 minutes to initiate a salt formation reaction. Then, 61.3 g of carbonyl chloride gas was blown in over 4 hours. Nitrogen gas was then bubbled to remove the carbonyl chloride from the system. After confirming that no carbonyl chloride remained, the reaction solution was brought to room temperature, concentrated using an evaporator, and the concentrate was dried under forced air at 45 °C to obtain 42.7 g of 4,4'-methylenebis(2,6-dibromo-isocyanate phenylene) as a brown powder (hereinafter referred to as Compound 6). The NCO content (mass of isocyanate groups relative to the total mass) was 14.3% by mass, and the bromine content was 56.0% by weight. This Compound 6 can be used as a scavenger for active hydrogen-containing organic compounds according to the present invention.

[0172] Synthesis Example 7

[0173] Under a nitrogen atmosphere, 50.0 g of 4,4'-methylenebis(3-bromoaniline) (nucleoside distribution: binucleate = 45%, triucleate = 18%, tetraucleate = 17%, pentaucleate and above = 20%) and 1400.0 g of chlorobenzene were added to a 2 L separable flask equipped with a stirrer, and the mixture was heated to 130 °C. 20.0 g of hydrochloric acid gas was blown into the solution over 120 minutes to initiate a salt formation reaction. Then, 110.0 g of carbonyl chloride gas was blown into the solution over 6 hours. Nitrogen gas was then bubbled to remove the carbonyl chloride from the system. After confirming that no carbonyl chloride remained, the reaction solution was brought to room temperature and concentrated using an evaporator. The concentrate was washed with a small amount of toluene and tetrahydrofuran, and the resulting powder was dried under forced air at 45 °C to obtain 40.7 g of 4,4'-methylenebis(3-bromo-isocyanate phenylene) as a brown powder (hereinafter referred to as the compound of Synthesis Example 7). The bromine content is 38.3% by weight. As described later, this compound of Synthetic Example 7 can be used as a scavenger of active hydrogen-containing organic compounds according to the present invention.

[0174] The table below shows the synthesized isocyanate compounds and the isocyanate compound (2,4,6-tribromoisocyanate phenyl) used in Example 5.

[0175] [Table 1]

[0176]

[0177] Example 1

[0178] A stir bar, 1.0 g of Compound Example 2, 9.0 g of activated carbon GranularShirasagi KL (manufactured by Osaka Gas Chemical Co., Ltd.), and 40 mL of tetrahydrofuran were added to a 200 mL eggplant-shaped flask and stirred at room temperature for 30 minutes. After removing the stir bar, the solvent was removed by filtration. The resulting solid was dried under vacuum at 100 °C for 8 hours to obtain 10.0 g of activated carbon-supported Compound Example 2 (the composition of the present invention, the active hydrogen-containing organic compound scavenger of the present invention).

[0179] Example 2

[0180] A stir bar, 1.0 g of Compound 2 (Synthetic Example 2), 9.0 g of GranularShirasagi WH2C8 / 32 activated carbon (manufactured by Osaka Gas Chemical Co., Ltd.), and 40 mL of tetrahydrofuran were added to a 200 mL eggplant-shaped flask and stirred at room temperature for 30 minutes. After removing the stir bar, the mixture was filtered to remove the solvent. The resulting solid was heated and dried under vacuum at 100 °C for 8 hours to obtain 10.0 g of activated carbon-supported Compound 2 (the composition of the present invention, the active hydrogen-containing organic compound scavenger of the present invention).

[0181] Example 3

[0182] A stir bar, 1.0 g of Compound Example 2, 9.0 g of activated carbon GranularShirasagi X7100H-3DRY (manufactured by Osaka Gas Chemical Co., Ltd.), and 40 mL of tetrahydrofuran were added to a 200 mL eggplant-shaped flask and stirred at room temperature for 30 minutes. After removing the stir bar, the mixture was filtered to remove the solvent. The resulting solid was heated and vacuum dried at 100 °C for 8 hours to obtain 10.0 g of activated carbon-supported Compound Example 2 as a black powder (the composition of the present invention, the active hydrogen-containing organic compound scavenger of the present invention).

[0183] Example 4

[0184] 20 mg of the compound of Synthetic Example 2 (the active hydrogen-containing organic compound scavenger of the present invention), pulverized into a fine powder, was placed in a 20 mL glass vial. The vial was then filled with a gas containing 10 ppm of 2-ethyl-1-hexanol (the remainder being nitrogen), and allowed to stand at room temperature for 3 hours. After standing, the concentration of 2-ethyl-1-hexanol in the gas within the vial was quantitatively analyzed using GC-MS (HERACLES II electronic olfaction system manufactured by Alpha MOS Japan). The results showed that 81% of the 2-ethyl-1-hexanol was captured and removed. Next, the inside of the vial was purged with nitrogen, and after heating at 60°C for 30 minutes, the 2-ethyl-1-hexanol was quantitatively analyzed using GC-MS. The results showed that the re-release rate of the captured 2-ethyl-1-hexanol was 0%.

[0185] Example 5

[0186] 20 mg (micro-powder form, the active hydrogen-containing organic compound capturing agent of this invention) of 2,4,6-tribromoisocyanate benzene (synthesized from 2,4,6-tribromoaniline (manufactured by Fujifilm and Koujun Pharmaceutical) via isocyanate esterification, with a bromine content of 67.1% by weight) was placed in a 20 mL glass vial. The vial was then filled with a gas containing 10 ppm of 2-ethyl-1-hexanol and allowed to stand at room temperature for 3 hours. After standing, the concentration of 2-ethyl-1-hexanol in the gas inside the vial was quantitatively analyzed by GCMS (HERACLESII electronic olfaction system manufactured by Alpha MOS Japan). The results showed that 90% of the 2-ethyl-1-hexanol was captured and removed. Next, the inside of the vial was purged with nitrogen, and after heating at 60°C for 30 minutes, the 2-ethyl-1-hexanol was quantitatively analyzed by GCMS. The results showed that the re-release rate of the captured 2-ethyl-1-hexanol was 0%.

[0187] Example 6

[0188] In Example 4, instead of using a gas containing 10 ppm of 2-ethyl-1-hexanol (the remainder being nitrogen), a gas containing 10 ppm of 2-methyl-1-butanol (the remainder being nitrogen) was used. Otherwise, the same operation as in Example 4 was performed, and the capture and re-release evaluation was conducted. The results showed that the capture and removal rate of 2-methyl-1-butanol was 89%, and the re-release rate was 0%.

[0189] Example 7

[0190] In Example 4, instead of using a gas containing 10 ppm of 2-ethyl-1-hexanol (the remainder being nitrogen), a gas containing 10 ppm of 2-methyl-1-propanol (the remainder being nitrogen) was used. Otherwise, the same operation as in Example 4 was performed, and the capture and re-release evaluation was conducted. The results showed that the capture removal rate of 2-methyl-1-propanol was 48%, and the re-release rate was 0%.

[0191] Comparative Example 1

[0192] In Example 4, except that 20 mg of the compound from Synthetic Example 2 was not added, the same operation as in Example 4 was performed (the empty small glass bottle was filled with a gas containing 10 ppm of 2-ethyl-1-hexanol (the remainder was nitrogen)) and the capture evaluation was carried out. The result showed that the capture removal rate of 2-ethyl-1-hexanol was 0%.

[0193] Comparative Example 2

[0194] In Example 4, 20 mg was used. β - Cyclodextrin (manufactured by Tokyo Chemical Industry Co., Ltd.) was used instead of 20 mg to synthesize Compound 2. Otherwise, the same procedure as in Example 4 was performed, and the capture evaluation was conducted. The result showed that the capture removal rate of 2-ethyl-1-hexanol was 0%.

[0195] Comparative Example 3

[0196] In Example 4, instead of 20 mg of the compound from Synthetic Example 2, 5 mg of activated carbon (premium powder manufactured by Fujifilm and Koichi Chemical Co., Ltd.) was used. Otherwise, the same operation as in Example 4 was performed, and the capture and re-release evaluation was conducted. The results showed that the capture removal rate of 2-ethyl-1-hexanol was 99%, and the re-release rate was 13%.

[0197] Comparative Example 4

[0198] In Example 4, 5 mg of activated carbon (premium powder manufactured by Fujifilm and Kojun Pharmaceutical Co., Ltd.) was used instead of 20 mg of the compound from Example 2. A gas containing 10 ppm of 2-methyl-1-butanol (the remainder being nitrogen) was used instead of a gas containing 10 ppm of 2-ethyl-1-hexanol (the remainder being nitrogen). Otherwise, the same procedures as in Example 4 were performed, and the capture and re-release evaluation was conducted. The results showed that the capture and removal rate of 2-methyl-1-butanol was 92%, and the re-release rate was 6%.

[0199] Comparative Example 5

[0200] In Example 4, 5 mg of activated carbon (premium powder manufactured by Fujifilm and Kojun Pharmaceutical Co., Ltd.) was used instead of 20 mg of the compound from Example 2. A gas containing 10 ppm of 2-methyl-1-propanol (the remainder being nitrogen) was used instead of a gas containing 10 ppm of 2-ethyl-1-hexanol (the remainder being nitrogen). Otherwise, the same procedures as in Example 4 were performed, and the capture and re-release evaluation was conducted. The results showed that the capture and removal rate of 2-methyl-1-propanol was 95%, and the re-release rate was 12%.

[0201] Comparative Example 6

[0202] In Example 4, 5 mg of CARiACT Q-50 (manufactured by Fuji Silysia Chemical Co., Ltd.) was used instead of 20 mg of the compound from Example 2. Otherwise, the same operation as in Example 4 was performed, and the capture and re-release evaluation was conducted. The results showed that the capture removal rate of 2-ethyl-1-hexanol was 86%, and the re-release rate was 25%.

[0203] Comparative Example 7

[0204] In Example 4, 5 mg of silica gel NIPGEL AY-001 (manufactured by Tosoh Silica Co., Ltd.) was used instead of 20 mg of the compound from Synthetic Example 2. Otherwise, the same operation as in Example 4 was performed, and the capture and re-release evaluation was conducted. The results showed that the capture removal rate of 2-ethyl-1-hexanol was 92%, and the re-release rate was 21%.

[0205] [Table 2]

[0206]

[0207] Example 8

[0208] A stir bar, 30 mg of the compound from Synthetic Example 2 (the active hydrogen-containing organic compound scavenger of this invention), and 10 mL of water were added to a 20 mL vial. The vial was then sealed and stirred at room temperature for 3 months. After filtering to remove the water, the resulting brown powder was subjected to FT-IR analysis. The analysis showed no change in peak intensity or pattern compared to before the experiment, indicating no long-term water decomposition. The results are shown in Table 3.

[0209] Example 9

[0210] A stir bar and 100 mg of Compound 2 (the active hydrogen-containing organic compound scavenger of the present invention) were added to a 20 mL vial. The vial was left uncovered and stirred at 60 °C for 2 hours in air. The resulting brown powder was then subjected to FT-IR analysis. The analysis showed no change in peak intensity or pattern compared to before the experiment, and no hydrolysis of isocyanate groups caused by trace amounts of moisture in the air was observed even under prolonged heating. The results are shown in Table 3.

[0211] Example 10

[0212] A stir bar, 30 mg of Compound Example 2 (the active hydrogen-containing organic compound scavenger of this invention), and 10 mL of 30% ethanol aqueous solution were added to a 20 mL vial. The vial was sealed and stirred at 45°C for 3 days. After filtering to remove the solvent, the resulting brown powder was analyzed by FT-IR. The analysis showed that, compared to before the experiment, the isocyanate group peak disappeared, and in its place, a carbonyl group peak originating from the reaction product of ethanol and the isocyanate group was observed. No peak change originating from hydrolysis was observed. That is, the isocyanate group of Compound Example 2 does not react with water but selectively reacts with ethanol. The results are shown in Table 3.

[0213] Example 11

[0214] A stir bar, 30 mg of Compound 2 (the active hydrogen-containing organic compound scavenger of this invention), 5 mL of toluene, and 5 mL of 5% ethanol aqueous solution were added to a 20 mL vial. The vial was sealed and stirred at 45°C for 3 days. The toluene layer was then concentrated into a dry solid, and the resulting brown powder was analyzed by FT-IR. The analysis showed that, compared to before the experiment, the isocyanate group peak disappeared, and in its place, a carbonyl group peak originating from the reaction product of ethanol and the isocyanate group was observed. No peak originating from hydrolysis was observed. That is, the isocyanate group of Compound 2 does not react with water but selectively reacts with ethanol. The results are shown in Table 3.

[0215] Example 12

[0216] A stir bar, 30 mg of Compound 3 (the active hydrogen-containing organic compound scavenger of the present invention), and a 30% aqueous ethanol solution were added to a 20 mL vial. The vial was sealed and stirred at 45°C for 3 days. After filtering to remove the solvent, the resulting powder was subjected to FT-IR analysis. The analysis showed that the isocyanate group peak disappeared, replaced by a carbonyl group peak. This indicates that the isocyanate group reacted with and captured the ethanol. Furthermore, no peak changes originating from hydrolysis were observed. That is, the isocyanate group of Compound 3 does not react with water but selectively reacts with ethanol. The results are shown in Table 3.

[0217] Example 27

[0218] A stir bar, 30 mg of Compound Example 6 (the active hydrogen-containing organic compound scavenger of this invention), and 10 mL of water were added to a 20 mL vial. The vial was sealed and stirred at room temperature for 3 months. After filtering to remove the water, the resulting brown powder was subjected to FT-IR analysis. The analysis showed no change in peak intensity or pattern compared to before the experiment, indicating no long-term water decomposition. The results are shown in Table 3.

[0219] Example 28

[0220] A stir bar and 100 mg of Compound 6 (the active hydrogen-containing organic compound scavenger of the present invention) were added to a 20 mL vial. The vial was left uncovered and stirred at 60 °C for 2 hours in air. The resulting brown powder was then subjected to FT-IR analysis. The analysis showed no change in peak intensity or pattern compared to before the experiment, and no hydrolysis of isocyanate groups caused by trace amounts of moisture in the air was observed even under prolonged heating. The results are shown in Table 3.

[0221] Example 2

[0222] A stir bar, 30 mg of Compound Example 6 (the active hydrogen-containing organic compound scavenger of the present invention), and 10 mL of 30% ethanol aqueous solution were added to a 20 mL vial. The vial was sealed and stirred at 45°C for 3 days. After filtering to remove the solvent, the resulting brown powder was analyzed by FT-IR. The analysis showed that, compared to before the experiment, the isocyanate group peak disappeared, and in its place, a carbonyl group peak originating from the reaction product of ethanol and the isocyanate group was observed. No peak change originating from hydrolysis was observed. That is, the isocyanate group of Compound Example 6 does not react with water but selectively reacts with ethanol. The results are shown in Table 3.

[0223] Example 30

[0224] A stir bar, 30 mg of Compound Example 6 (the active hydrogen-containing organic compound scavenger of the present invention), 5 mL of toluene, and 5 mL of 5% ethanol aqueous solution were added to a 20 mL vial. The vial was sealed and stirred at 45°C for 3 days. The toluene layer was then concentrated into a dry solid, and the resulting brown powder was analyzed by FT-IR. The analysis showed that, compared to before the experiment, the isocyanate group peak disappeared, and in its place, a carbonyl group peak originating from the reaction product of ethanol and the isocyanate group was observed. No peak originating from hydrolysis was observed. That is, the isocyanate group of Compound Example 6 does not react with water but selectively reacts with ethanol. The results are shown in Table 3.

[0225] Comparative Example 8

[0226] A stir bar, 30 mg of polymeric MDI (manufactured by Tosoh Corporation; Millionate MR-200), and 10 mL of water were added to a 20 mL vial. The vial was sealed and stirred at room temperature for one month. After filtering to remove the water, the resulting solid was subjected to FT-IR analysis. The analysis showed significant changes in peak intensity and pattern compared to before the experiment, indicating that the polymeric MDI was decomposed by water. The results are shown in Table 3.

[0227] Comparative Example 9

[0228] A stir bar and 100 mg of polymeric MDI (manufactured by Tosoh Corporation; Millionate MR-200) were added to a 20 mL vial. The vial was left uncovered and stirred at 60 °C for 14 days in air. The resulting solid was then subjected to FT-IR analysis. The analysis revealed significant changes in peak intensity and pattern compared to the initial values. This indicates that the polymeric MDI was decomposed by trace amounts of moisture in the air under heating conditions. The results are shown in Table 3.

[0229] Comparative Example 10

[0230] A stir bar, 30 mg of polymeric MDI (manufactured by Tosoh Corporation; Millionate MR-200), and a 30% aqueous ethanol solution were added to a 20 mL vial. The vial was sealed and stirred at 45°C for 3 days. After filtering to remove the solvent, the resulting solid was analyzed by FT-IR. The analysis showed that, compared to before the experiment, the isocyanate group peak disappeared, replaced by carbonyl group peaks originating from the reaction product of ethanol and polymeric MDI, and peaks originating from the hydrolysis of polymeric MDI. That is, polymeric MDI causes a lack of selectivity in the reaction between water and ethanol. The results are shown in Table 3.

[0231] Comparative Example 11

[0232] A stir bar, 30 mg of 2,4,6-tri-tert-butyl isocyanate phenylene oxide, and a 30% aqueous ethanol solution were added to a 20 mL vial. The vial was sealed and stirred at 45 °C for 3 days. After filtering to remove the solvent, the resulting solid was subjected to FT-IR analysis. The analysis showed that the isocyanate group peak remained unchanged compared to the initial value, and the shapes of other peaks were also completely unchanged. That is, 2,4,6-tri-tert-butyl isocyanate phenylene oxide prevents any reaction with water or ethanol. The results are shown in Table 3.

[0233] According to Table 3, materials containing isocyanate compounds represented by formula (1) are resistant to moisture in the environment and have the ability to capture alcohol compounds.

[0234] [Table 3]

[0235]

[0236] Example 13 (Silicone Loading Product 1 CARiACT Q-10)

[0237] A stir bar, 1.0 g of the compound from Synthetic Example 2, 9.0 g of silica gel CARiACT Q-10 (manufactured by Fuji Silysia Chemical Co., Ltd.), and 200 mL of dichloromethane were added to a 500 mL pear-shaped flask and stirred at room temperature for 30 minutes. After removing the stir bar, the solvent was slowly removed under reduced pressure using an evaporator. The resulting solid was dried at 60°C under a nitrogen stream for 3 hours, and then further dried at room temperature under a nitrogen stream for 24 hours. This yielded the silica gel-supported product of the compound from Synthetic Example 2 (the composition of the present invention, the active hydrogen-containing organic compound scavenger of the present invention).

[0238] Example 14 (Silicone-supported product 2 CARiACT G-10)

[0239] A stir bar, 0.5 g of the compound from Synthetic Example 2, 9.5 g of silica gel CARiACT G-10 (manufactured by Fuji Silysia Chemical Co., Ltd.), and 200 mL of dichloromethane were added to a 500 mL pear-shaped flask and stirred at room temperature for 30 minutes. After removing the stir bar, the solvent was slowly removed under reduced pressure using an evaporator. The resulting solid was dried at 60°C under a nitrogen stream for 3 hours, and then further dried at room temperature under a nitrogen stream for 24 hours. This yielded the silica gel-supported product of the compound from Synthetic Example 2 (the composition of the present invention, the active hydrogen-containing organic compound scavenger of the present invention).

[0240] Example 15 (Silicone Loading Material 3 NIPGEL AY-001)

[0241] A stir bar, 0.5 g of the compound from Synthetic Example 2, 9.5 g of silica gel NIPGEL AY-001 (manufactured by Tosoh Silica Co., Ltd.), and 200 mL of dichloromethane were added to a 500 mL piezoelectric flask and stirred at room temperature for 30 minutes. After removing the stir bar, the solvent was slowly removed under reduced pressure using an evaporator. The resulting solid was dried at 60°C under a nitrogen stream for 3 hours, and then further dried at room temperature under a nitrogen stream for 24 hours. This yielded the silica gel-supported product of the compound from Synthetic Example 2 (the composition of the present invention, the active hydrogen-containing organic compound scavenger of the present invention).

[0242] Example 16 (Silicone Loading Material 4 NIPGEL AY-220D)

[0243] A stir bar, 0.5 g of the compound from Synthetic Example 2, 9.5 g of silica gel NIPGEL AY-220D (manufactured by Tosoh Silica Co., Ltd.), and 200 mL of dichloromethane were added to a 500 mL pear-shaped flask and stirred at room temperature for 30 minutes. After removing the stir bar, the solvent was slowly removed under reduced pressure using an evaporator. The resulting solid was dried at 60°C under a nitrogen stream for 3 hours, and then further dried at room temperature under a nitrogen stream for 24 hours. This yielded the silica gel-supported product of the compound from Synthetic Example 2 (the composition of the present invention, the active hydrogen-containing organic compound scavenger of the present invention).

[0244] Example 17 (Silicone Loading Material 4' NIPGEL CX-200)

[0245] A stir bar, 0.5 g of Compound Example 2, 9.5 g of NIPGEL CX-200 silica gel (manufactured by Tosoh Silica Co., Ltd.), and 200 mL of dichloromethane were added to a 500 mL pear-shaped flask and stirred at room temperature for 30 minutes. After removing the stir bar, the solvent was slowly removed under reduced pressure using an evaporator. The resulting solid was dried at 60°C under a nitrogen stream for 3 hours, and then further dried at room temperature under a nitrogen stream for 24 hours. This yielded a silica gel-supported product of Compound Example 2 (the composition of the present invention, the active hydrogen-containing organic compound scavenger of the present invention).

[0246] Example 18 (Cellulose-loaded Viscopearl A)

[0247] A stir bar, 0.5 g of the compound from Synthetic Example 2, 9.5 g of cellulose Viscopearl A (manufactured by Rengo Co., Ltd.), and 200 mL of dichloromethane were added to a 500 mL pear-shaped flask and stirred at room temperature for 30 minutes. After removing the stir bar, the solvent was slowly removed under reduced pressure using an evaporator. The resulting solid was dried at 60°C under a nitrogen stream for 3 hours, and then further dried at room temperature under a nitrogen stream for 24 hours. This process yielded a cellulose-supported product of the compound from Synthetic Example 2 (the composition of the present invention, the active hydrogen-containing organic compound scavenger of the present invention).

[0248] Example 19 (Silicone Loading Material 5 CARiACT Q-50)

[0249] A stir bar, 0.5 g of the compound from Synthetic Example 3, 9.5 g of silica gel CARiACT Q-50 (manufactured by Fuji Silysia Chemical Co., Ltd.), and 200 mL of dichloromethane were added to a 500 mL pear-shaped flask and stirred at room temperature for 30 minutes. After removing the stir bar, the solvent was slowly removed under reduced pressure using an evaporator. The resulting solid was dried at 60°C under a nitrogen stream for 3 hours, and then further dried at room temperature under a nitrogen stream for 24 hours. This yielded the silica gel-supported product of the compound from Synthetic Example 3 (the composition of the present invention, the active hydrogen-containing organic compound scavenger of the present invention).

[0250] Example 20 (Silicone Loading Material 6 NIPGEL AY-001)

[0251] A stir bar, 0.5 g of the compound from Synthetic Example 3, 9.5 g of silica gel NIPGEL AY-001 (manufactured by Tosoh Silica Co., Ltd.), and 200 mL of dichloromethane were added to a 500 mL pear-shaped flask and stirred at room temperature for 30 minutes. After removing the stir bar, the solvent was slowly removed under reduced pressure using an evaporator. The resulting solid was dried at 60°C under a nitrogen stream for 3 hours, and then further dried at room temperature under a nitrogen stream for 24 hours. This yielded the silica gel-supported product of the compound from Synthetic Example 3 (the composition of the present invention, the active hydrogen-containing organic compound scavenger of the present invention).

[0252] Example 31 (Silicone Loading Material 7 NIPGEL CX-200)

[0253] A stir bar, 0.5 g of Compound Example 6, 9.5 g of silica gel NIPGEL CX-200 (manufactured by Tosoh Silica Co., Ltd.), and 200 mL of dichloromethane were added to a 500 mL pear-shaped flask and stirred at room temperature for 30 minutes. After removing the stir bar, the solvent was slowly removed under reduced pressure using an evaporator. The resulting solid was dried at 60°C under a nitrogen stream for 3 hours, and then further dried at room temperature under a nitrogen stream for 24 hours. This yielded the silica gel-supported product of Compound Example 6 (the composition of the present invention, the active hydrogen-containing organic compound scavenger of the present invention).

[0254] Example 32 (hydrotalcite-loaded product KYOWAAD500)

[0255] A stir bar, 0.5 g of Compound Example 2, 9.5 g of KYOWAAD500 (hydrotalcite manufactured by Kyowa Chemical Industry Co., Ltd.), and 200 mL of dichloromethane were added to a 500 mL pear-shaped flask and stirred at room temperature for 30 minutes. After removing the stir bar, the solvent was slowly removed under reduced pressure using an evaporator. The resulting solid was dried at 60°C under a nitrogen stream for 3 hours, and then further dried at room temperature under a nitrogen stream for 24 hours. This yielded the hydrotalcite-supported product of Compound Example 2 (the composition of the present invention, the active hydrogen-containing organic compound scavenger of the present invention).

[0256] [Gas Capture Evaluation]

[0257] For the scavenging agent of the present invention containing active hydrogen organic compounds, the following is used: Figure 1 An evaluation device for capturing active hydrogen organic compound gases, as shown in the schematic diagram, was used. This active hydrogen organic compound gas adsorption device includes a storage tank (a 20L container manufactured by SUS), a gas circulation pump, a column filled with a capturing agent (a 0.1L glass container), and a heater. The storage tank is filled with a gas containing active hydrogen organic compounds (ethanol, isopropanol, or acetic acid) to create a circulating gas atmosphere (with the remainder being nitrogen) of a specified concentration. 5g of the capturing agent of this invention is filled into the column, and the temperature is adjusted to 25°C. Using the circulation pump, circulating gas, also heated to 25°C in the heater, is passed through the column at a rate of 10L / min for 3 hours, and the concentration of active hydrogen organic compounds in the circulating gas in the storage tank after 3 hours is measured. Next, the column filled with the capturing agent is heated to 60°C using the heater. Using a circulating pump, circulating gas, also heated to 60°C in the heater, is passed through the column at a rate of 10 L / min over 30 minutes. The concentration of active hydrogen-containing organic compounds in the gas in the storage tank is then measured after 30 minutes.

[0258] Example 21 (Ethanol Gas Capture Evaluation)

[0259] The active hydrogen-containing organic compound gas capture capacity evaluation device was set to a 500 ppm ethanol atmosphere (with the remainder being nitrogen). Next, the column of the active hydrogen-containing organic compound gas capture capacity evaluation device was filled with the silica gel support of Example 13 (the composition of the present invention, the active hydrogen-containing organic compound capture agent of the present invention), and the evaluation was performed. After cycling at 25°C for 3 hours, the ethanol gas concentration in the device was 145 ppm. After cycling at 60°C for 30 minutes, the ethanol gas concentration in the device was 285 ppm. The amount of ethanol equivalent to the deducted 215 ppm (=500 ppm - 285 ppm) was captured and not released back onto the silica gel support of Example 13. The results are shown in Table 4.

[0260] Example 22 (Ethanol Gas Capture Evaluation)

[0261] The active hydrogen-containing organic compound gas capture capacity evaluation device was set to a 500 ppm ethanol atmosphere (with the remainder being nitrogen). Next, the silica gel support of Example 14 (the composition of the present invention, the active hydrogen-containing organic compound capture agent of the present invention) was filled into the column of the active hydrogen-containing organic compound gas capture capacity evaluation device, and the evaluation was performed. After cycling at 25°C for 3 hours, the ethanol gas concentration in the device was 15 ppm. After cycling at 60°C for 30 minutes, the ethanol gas concentration in the device was 160 ppm. The amount of ethanol equivalent to the deducted 340 ppm (=500 ppm - 160 ppm) was captured and not released back onto the silica gel support of Example 14. The results are shown in Table 4.

[0262] Example 23 (Ethanol Gas Capture Evaluation)

[0263] The active hydrogen-containing organic compound gas capture capacity evaluation device was set to a 500 ppm ethanol atmosphere (with the remainder being nitrogen). Next, the column of the active hydrogen-containing organic compound gas capture capacity evaluation device was filled with the silica gel support of Example 15 (the composition of the present invention, the active hydrogen-containing organic compound capture agent of the present invention), and the evaluation was performed. After cycling at 25°C for 3 hours, the ethanol gas concentration in the device was less than 5 ppm. After cycling at 60°C for 30 minutes, the ethanol gas concentration in the device was 55 ppm. The equivalent of a deducted amount of 445 ppm (=500 ppm - 55 ppm) of ethanol was captured without being released back onto the silica gel support of Example 15. The results are shown in Table 4.

[0264] Example 24 (Ethanol Gas Capture Evaluation)

[0265] The active hydrogen-containing organic compound gas capture capacity evaluation device was set to a 500 ppm ethanol atmosphere (with the remainder being nitrogen). Next, the column of the active hydrogen-containing organic compound gas capture capacity evaluation device was filled with the silica gel support of Example 16 (the composition of the present invention, the active hydrogen-containing organic compound capture agent of the present invention), and the evaluation was performed. After cycling at 25°C for 3 hours, the ethanol gas concentration in the device was 10 ppm. After cycling at 60°C for 30 minutes, the ethanol gas concentration in the device was 70 ppm. The amount of ethanol equivalent to the deducted 430 ppm (=500 ppm - 70 ppm) was irreversibly captured by the silica gel support of Example 16. The results are shown in Table 4.

[0266] Example 25 (Ethanol Gas Capture Evaluation)

[0267] The active hydrogen-containing organic compound gas capture capacity evaluation device was set to a 500 ppm ethanol atmosphere (with the remainder being nitrogen). Next, the column of the active hydrogen-containing organic compound gas capture capacity evaluation device was filled with the silica gel support of Example 17 (the composition of the present invention, the active hydrogen-containing organic compound capture agent of the present invention), and the evaluation was performed. After cycling at 25°C for 3 hours, the ethanol gas concentration in the device was less than 5 ppm. After cycling at 60°C for 30 minutes, the ethanol gas concentration in the device was 15 ppm. The equivalent of a deducted amount of 485 ppm (=500 ppm - 15 ppm) of ethanol was captured without being released back onto the silica gel support of Example 17. The results are shown in Table 4.

[0268] Example 26 (Evaluation of Ethanol Gas Capture)

[0269] The active hydrogen-containing organic compound gas capture capacity evaluation device was set to a 500 ppm ethanol atmosphere (the remainder being nitrogen). Next, the silica gel support of Example 20 (the composition of the present invention, the active hydrogen-containing organic compound capture agent of the present invention) was filled into the column of the active hydrogen-containing organic compound gas capture capacity evaluation device, and the evaluation was performed. After cycling at 25°C for 3 hours, the ethanol gas concentration in the device was 10 ppm. After cycling at 60°C for 30 minutes, the ethanol gas concentration in the device was 50 ppm. The amount of ethanol equivalent to the deducted 450 ppm (=500 ppm - 50 ppm) was captured and not released back onto the silica gel support of Example 20. The results are shown in Table 4.

[0270] Example 33 (Ethanol Gas Capture Evaluation)

[0271] The active hydrogen organic compound gas capture capacity evaluation device was set to a 500 ppm ethanol atmosphere (with the remainder being nitrogen). Next, the silica gel support of Example 31 (the composition of the present invention, the active hydrogen organic compound capture agent of the present invention) was filled into the column of the active hydrogen organic compound gas capture capacity evaluation device, and the evaluation was performed. After cycling at 25°C for 3 hours, the ethanol gas concentration in the device was 5 ppm. After cycling at 60°C for 30 minutes, the ethanol gas concentration in the device was 15 ppm. The equivalent of a deducted amount of 485 ppm (=500 ppm - 15 ppm) of ethanol was captured without being released back onto the silica gel support of Example 31. The results are shown in Table 4.

[0272] Example 34 (Evaluation of Isopropanol Gas Capture)

[0273] In Example 33, the gas type (the active hydrogen-containing organic compound to be captured) was changed from ethanol to isopropanol; otherwise, the same procedures as in Example 33 were performed. The isopropanol gas concentration in the apparatus after 3 hours of circulation at 25°C was 10 ppm. The isopropanol gas concentration in the apparatus after 30 minutes of circulation at 60°C was 30 ppm. The equivalent of a deducted amount of 470 ppm (=500 ppm - 30 ppm) of isopropanol was captured and not released back onto the silica gel support of Example 31. The results are shown in Table 4.

[0274] Example 35 (Evaluation of Acetic Acid Gas Capture)

[0275] In Example 33, the gas used (the active hydrogen-containing organic compound to be captured) was changed from ethanol to acetic acid, and the initial acetic acid gas concentration was changed to 15.0 ppm. Otherwise, the same procedures as in Example 33 were followed. After 3 hours of circulation at 25°C, the acetic acid gas concentration in the apparatus was 0.2 ppm. After 30 minutes of circulation at 60°C, the acetic acid gas concentration in the apparatus was 0.4 ppm. The equivalent of a deducted amount of 14.7 ppm (=15.0 ppm - 0.4 ppm) of acetic acid was captured and not released back onto the silica gel support of Example 31. The results are shown in Table 4.

[0276] Example 36 (Evaluation of Ethanol Gas Capture)

[0277] The active hydrogen-containing organic compound gas capture capacity evaluation device was set to a 500 ppm ethanol atmosphere (with the remainder being nitrogen). Next, the column of the active hydrogen-containing organic compound gas capture capacity evaluation device was filled with the hydrotalcite loading material of Example 32 (the composition of the present invention, the active hydrogen-containing organic compound capture agent of the present invention), and the evaluation was performed. After cycling at 25°C for 3 hours, the ethanol gas concentration in the device was 55 ppm. After cycling at 60°C for 30 minutes, the ethanol gas concentration in the device was 80 ppm. The amount of ethanol equivalent to the deducted 420 ppm (=500 ppm - 80 ppm) was captured and not released back onto the hydrotalcite loading material of Example 32. The results are shown in Table 4.

[0278] Comparative Example 12

[0279] The active hydrogen organic compound gas capture capacity evaluation device was set to a 500 ppm ethanol atmosphere (with the remainder in nitrogen). Then, the column of the device was left empty (remaining empty) and the evaluation was performed. After 3 hours of circulation at 25°C, the ethanol gas concentration in the device was 500 ppm. After 30 minutes of circulation at 60°C, the ethanol gas concentration in the device was also 500 ppm. There was no change in the ethanol concentration in the gas. The results are shown in Table 4.

[0280] Comparative Example 13

[0281] The active hydrogen organic compound gas capture capacity evaluation device was set to a 15.0 ppm acetic acid atmosphere (the remainder being nitrogen). Next, the column of the active hydrogen organic compound gas capture capacity evaluation device was left empty (remaining empty) and the evaluation was performed. After 3 hours of circulation at 25°C, the acetic acid gas concentration in the device was 15.0 ppm. After 30 minutes of circulation at 60°C, the acetic acid gas concentration in the device was also 15.0 ppm. There was no change in the acetic acid concentration in the gas. The results are shown in Table 4.

[0282] [Table 4]

[0283]

[0284] Although the present invention has been described in detail with reference to specific embodiments, it will be apparent to those skilled in the art that various changes and modifications can be made without departing from the spirit and scope of the invention.

[0285] Furthermore, the entire contents of the description, claims, drawings, and abstracts of Japanese Patent Application No. 2020-200086, filed on December 2, 2020, and Japanese Patent Application No. 2021-125610, filed on July 30, 2021, are incorporated herein by reference and are included as disclosure in this specification.

[0286] Explanation of reference numerals in the attached figures

[0287] 10. Storage tank (20L container manufactured by SUS)

[0288] 11. Thermometer and hygrometer

[0289] 12. Gas flow meter

[0290] 13. Gas circulation pump

[0291] 14. Heater

[0292] 15. Thermometer

[0293] 16. Pressure gauge

[0294] 17. Column filled with trapping agent

[0295] 18. Heater

[0296] 19. Valve

[0297] 20. Flow direction of circulating gas

[0298] Industrial availability

[0299] According to the present invention, it is possible to efficiently capture active hydrogen-containing organic compounds such as alcohols, which are difficult to capture in previous technologies. Furthermore, due to its irreversible capture capability, it maintains a continuous capture effect even in environments with moisture, and therefore can be used as a capture agent for active hydrogen-containing organic compounds in various scenarios such as the environmental, energy, medical, and life science fields.

Claims

1. The application of active hydrogen-containing organic compound scavengers in the capture of active hydrogen-containing organic compounds, wherein, The active hydrogen-containing organic compound is brought into contact with the active hydrogen-containing organic compound scavenging agent to capture the active hydrogen-containing organic compound. The active hydrogen-containing organic compound is at least one compound selected from alcohols, thiols, amines, phenols, and carboxylic acids. The active hydrogen-containing organic compound scavenger comprises: Isocyanate compounds of the following formula (1) with a bromine content of 38 wt% to 78 wt%: ; In equation (1), R 1 and R 2 Each can independently represent either a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; R 3 Each of the following can independently represent a hydrogen atom, an alkyl group with 1 to 4 carbon atoms, or a bromine atom; m represents at least one atom selected from 0, 1, 2, and 3; n represents a real number greater than 0. The isocyanate compound is a single compound or a mixture of multiple compounds; in the case of a mixture, n represents the average value of the mixture.

2. The use according to claim 1, wherein, The isocyanate compound represented by formula (1) is the isocyanate compound represented by formula (1a) below: ; In equation (1a), R 1 and R 2 Each can independently represent either a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; R 3 Each of the following can independently represent a hydrogen atom, an alkyl group with 1 to 4 carbon atoms, or a bromine atom; m represents at least one atom selected from 0, 1, 2, and 3; n represents a real number greater than 0. The isocyanate compound is a single compound or a mixture of multiple compounds; in the case of a mixture, n represents the average value of the mixture.

3. The use according to claim 1, wherein, The isocyanate compound represented by formula (1) is the isocyanate compound represented by formula (1b) below: ; In equation (1b), R 1 and R 2 Each can independently represent either a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; R 3 Each of the following can be used independently to represent a hydrogen atom, an alkyl group with 1 to 4 carbon atoms, or a bromine atom; n represents a real number greater than 0. The isocyanate compound is a single compound or a mixture of multiple compounds; in the case of a mixture, n represents the average value of the mixture.

4. The use according to any one of claims 1 to 3, wherein, The bromine content is 50wt% to 78wt%.

5. The use according to any one of claims 1 to 3, wherein, The R 1 and R 2 Each can be a hydrogen atom or a methyl group, independently.

6. The use according to any one of claims 1 to 3, wherein, The R 1 and R 2 It is a hydrogen atom.

7. The use according to any one of claims 1 to 3, wherein, In the above equation (1), R 3 Each can be a hydrogen atom or a bromine atom, independently.

8. The use according to any one of claims 1 to 3, wherein, The n is a real number between 0 and 3.

9. The use according to any one of claims 1 to 3, wherein, The active hydrogen-containing organic compound scavenger is a mixture of multiple nucleosome compounds, which includes: 0%–20% mononuclear compounds, 10%–99% dinuclear compounds, 5%–60% trinuclear compounds, and 0%–30% tetranuclear compounds or more. The total percentage of mononuclear compounds, dinuclear compounds, trinuclear compounds, and tetranuclear compounds or more is 100%.

10. A composition comprising: Isocyanate compounds and supports of the following formula (1) with a bromine content of 38 wt% to 78 wt%: ; In equation (1), R 1 and R 2 Each can independently represent either a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; R 3 Each of the following can independently represent a hydrogen atom, an alkyl group with 1 to 4 carbon atoms, or a bromine atom; m represents at least one atom selected from 0, 1, 2, and 3; n represents a real number greater than 0. The isocyanate compound is a single compound or a mixture of multiple compounds; in the case of a mixture, n represents the average value of the mixture. The isocyanate compound is loaded onto the support.

11. The composition according to claim 10, wherein, The isocyanate compound represented by formula (1) is the isocyanate compound represented by formula (1a) below: ; In equation (1a), R 1 and R 2 Each can independently represent either a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; R 3 Each of the following can be independently represented: a hydrogen atom, an alkyl group with 1 to 4 carbon atoms, or a bromine atom; m represents at least one of the following: 0, 1, 2, and 3; n represents a real number greater than 0. The isocyanate compound is a single compound or a mixture of multiple compounds; in the case of a mixture, n represents the average value of the mixture.

12. The composition according to claim 10, wherein, The isocyanate compound represented by formula (1) is the isocyanate compound represented by formula (1b) below: ; In equation (1b), R 1 and R 2 Each can independently represent either a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; R 3 Each of the following can independently represent a hydrogen atom, an alkyl group with 1 to 4 carbon atoms, or a bromine atom; n can independently represent a real number greater than 0. The isocyanate compound is a single compound or a mixture of multiple compounds; in the case of a mixture, n represents the average value of the mixture.

13. The composition according to any one of claims 10 to 12, wherein, The R 3 Each can be a hydrogen atom or a bromine atom, independently.

14. The composition according to any one of claims 10 to 12, wherein, The loading of the isocyanate compound is 0.1 to 60 parts by weight relative to 100 parts by weight of the carrier.

15. The composition according to any one of claims 10 to 12, wherein, The carrier is selected from one or more of the following: activated carbon, activated clay, diatomaceous earth, porous resin, nonwoven fabric, mesoporous silica, silica gel, aluminosilicate, hydrotalcite, zeolite, activated alumina, titanium dioxide, magnesium oxide, and zirconium oxide.

16. An active hydrogen-containing organic compound scavenger comprising the composition of any one of claims 10 to 15.

17. A method for capturing organic compounds containing active hydrogen, characterized in that, Contacting the composition according to any one of claims 10-15 with the active hydrogen-containing organic compound allows for the capture of the active hydrogen-containing organic compound. The active hydrogen-containing organic compound is selected from at least one compound selected from alcohols, thiols, amines, phenols, and carboxylic acids.

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