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

Abstract

To provide a material for efficiently capturing an active hydrogen-containing organic compound such as an alcohol compound.SOLUTION: An active hydrogen-containing organic compound scavenger is used, the scavenger contains an isocyanate compound represented by the following general formula (1) and having a bromine content of 38 to 78 wt% (in the above general formula, R1 and R2 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and R3 is each, independently, represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a bromine atom. m represents at least one selected from the group consisting of 0, 1, 2, and 3. n represents an actual number of 0 or more) (may be a single compound, a mixture of a plurality of compounds, in the case of mixture, n represents an average value of the mixture).SELECTED DRAWING: None

Description

[Technical Field]

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

[0002] Volatile organic compound (VOC) scavenging agents and technologies are used in various aspects of daily life. For example, technologies for scavenging amine compounds and aromatic hydrocarbon compounds, which are known to be the cause of sick building syndrome, include technologies that utilize the inclusion action of cyclodextrin compounds and technologies that utilize the neutralization action of amino acids. In both of these scavenging technologies, the agent is sprayed into the air to capture VOCs floating in the air, thereby purifying the indoor space. In addition, porous inorganic materials are known to adsorb various VOCs, and for example, scavenging agents such as activated carbon deodorizing filters have been developed.

[0003] Meanwhile, against the backdrop of growing safety awareness regarding chemical substances, alcohol-based VOCs have recently attracted attention. For example, in Japan, the addition of two alcohol-based chemical substances (2-ethyl-1-hexanol and texanol) as new causes of sick building syndrome is being discussed. These alcohol compounds are known to be generated from the deterioration of building material resins and water-based paint components, but effective capture technologies have not yet been established. In addition, alcohol-based VOCs such as 2-methyl-1-butanol and 1-pentanol can also be generated during the growth and metabolic processes of microorganisms, and are a contributing factor to the so-called musty odor (Non-Patent Literature 1). [Prior art documents] [Non-patent literature]

[0004] [Non-Patent Document 1] Journal of the Japanese Society for Odor and Fragrance Environment, 2012, Vol. 43, pp. 184-190. [Overview of the project]

Problems to be Solved by the Invention

[0005] An object of the present invention is to provide a scavenger for active hydrogen-containing organic compounds such as alcohol compounds that are difficult to capture by conventional techniques.

Means for Solving the Problems

[0006] As a result of intensive studies to solve the above problems, the present inventors have found that the following scavenger or the following composition can capture active hydrogen-containing organic compounds such as alcohol compounds that have been difficult to capture conventionally, and have completed the present invention.

[0007] That is, one aspect of the present invention relates to a scavenger or composition as shown below, and their uses.

[0008] [1] An isocyanate compound represented by the following general formula (1) having a bromine content of 38 to 78 wt%

[0009]

Chemical Formula

[0010] (In the above general formula, R 1 and R 2 each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. R 3 each independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a bromine atom. m represents at least one selected from the group consisting of 0, 1, 2, and 3. n represents a real number of 0 or more.) An active hydrogen-containing organic compound scavenger containing an isocyanate compound represented by (which may be a single compound or a mixture of a plurality of compounds, and in the case of a mixture, n represents the average value of the mixture).

[0011] [2] The isocyanate compound represented by the above general formula (1) (which may be a single compound or a mixture of a plurality of compounds; in the case of a mixture, n represents the average value of the mixture) is represented by the following general formula (1a)

[0012]

Chemical formula

[0013] (In the above general formula, R 1 and R 2 each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. R 3 each independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a bromine atom. m represents at least one selected from the group consisting of 0, 1, 2, and 3. n represents a real number of 0 or more.) The active hydrogen-containing organic compound scavenger according to [1] above, characterized in that it is an isocyanate compound represented by the following general formula (1) (which may be a single compound or a mixture of a plurality of compounds; in the case of a mixture, n represents the average value of the mixture).

[0014] [3] The isocyanate compound represented by the above general formula (1) (which may be a single compound or a mixture of a plurality of compounds; in the case of a mixture, n represents the average value of the mixture) is represented by the following general formula (1b)

[0015]

Chemical formula

[0016] (In the above general formula, R 1 and R 2 each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. R 3 each independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a bromine atom. n represents a real number of 0 or more.) The active hydrogen-containing organic compound scavenger according to [1] above, characterized in that it is an isocyanate compound represented by (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).

[0017] [4] An active hydrogen-containing organic compound scavenger according to any one of [1] to [3], characterized in that the bromine content is 50 to 78 wt%.

[0018] [5] The aforementioned R 1 and R 2 The active hydrogen-containing organic compound scavenger according to any one of [1] to [4] above, characterized in that each is independently a hydrogen atom or a methyl group.

[0019] [6] The aforementioned R 1 and R 2 The active hydrogen-containing organic compound scavenger according to any one of [1] to [5] above, characterized in that the hydrogen atom is a hydrogen atom.

[0020] [7] In the general formula (1) above, R 3 The active hydrogen-containing organic compound scavenger according to any one of [1] to [6] above, characterized in that each is independently a hydrogen atom or a bromine atom.

[0021] [8] An active hydrogen-containing organic compound scavenger according to any one of [1] to [7] above, wherein n is a real number from 0 to 3.

[0022] [9] A method for capturing a compound, characterized by contacting an active hydrogen-containing organic compound scavenger described in any of [1] to [8] above with at least one compound selected from the group consisting of alcohol compounds, thiol compounds, amine compounds, phenol compounds, and carboxylic acid compounds, and capturing the compound.

[0023]

[10] The following general formula (1) has a bromine content of 38-78 wt%

[0024] [ka]

[0025] (In the above general formula, R 1 and R 2 Each of these independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. 3 Each of the following independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a bromine atom. m represents at least one selected from the group consisting of 0, 1, 2, and 3. n independently represents a real number greater than or equal to 0. A composition comprising an isocyanate compound represented by (which may be a single compound or a mixture of multiple compounds, in the case of a mixture, where n represents the average value of the mixture) and a carrier.

[0026]

[11] The isocyanate compound represented by the above general 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 given by the following general formula (1a)

[0027] [ka]

[0028] (In the above general formula, R 1 and R 2 Each of these independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. 3 Each of the following independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a bromine atom. m represents at least one selected from the group consisting of 0, 1, 2, and 3. n independently represents a real number greater than or equal to 0. The composition according to

[10] , characterized in that it is an isocyanate compound represented by (which may be a single compound or a mixture of multiple compounds, in the case of a mixture, where n represents the average value of the mixture).

[0029]

[12] The isocyanate compound represented by the above general 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 given by the following general formula (1b)

[0030] [ka]

[0031] (In the above general formula, R 1 and R 2 Each of these independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. 3 Each of these independently represents a hydrogen atom, an alkyl group with 1 to 4 carbon atoms, or a bromine atom. Each of these independently represents a real number greater than or equal to 0. The composition according to

[10] , characterized in that it is an isocyanate compound represented by (which may be a single compound or a mixture of multiple compounds, in the case of a mixture, where n represents the average value of the mixture).

[0032]

[13] The aforementioned R 3 The composition according to any one of

[10] to

[12] , characterized in that each is independently a hydrogen atom or a bromine atom.

[0033]

[14] A composition according to any one of the above

[10] to

[13] , characterized in that the isocyanate compound is supported on the carrier.

[0034]

[15] The composition according to any one of

[10] to

[14] , wherein the amount of the isocyanate compound supported is 0.1 to 60 parts by weight per 100 parts by weight of the carrier.

[0035]

[16] The composition according to any one of

[10] to

[15] , wherein the carrier is one or more carriers selected from the group consisting of activated carbon, activated clay, diatomaceous earth, porous resin, nonwoven fabric, mesoporous silica, silica gel, aluminosilicate, hydrotalcite, zeolite, activated alumina, titania, magnesia, and zirconia.

[0036]

[17] An active hydrogen-containing organic compound scavenger comprising the composition described in any of the above

[10] to

[16] .

[0037]

[18] A method for capturing a compound, characterized by contacting the composition described in any of

[10] to

[16] above with at least one compound selected from the group consisting of alcohol compounds, thiol compounds, amine compounds, phenol compounds, and carboxylic acid compounds, and capturing the compound. [Effects of the Invention]

[0038] The scavenger or composition of the present invention can capture active hydrogen-containing organic compounds, such as alcohol compounds, with higher selectivity compared to conventionally known scavenging techniques.

[0039] The scavenger or composition of the present invention captures active hydrogen-containing organic compounds through a chemical reaction with isocyanate groups. As a result, once captured, the active hydrogen-containing organic compounds are hardly re-released, eliminating concerns about re-contamination of the space. Furthermore, due to its high water resistance, it exhibits the effect of sustained active hydrogen-containing organic compound scavenging ability in living environments. [Modes for carrying out the invention]

[0040] The present invention will be described in detail below.

[0041] The present invention relates to the above-described scavenging agents or compositions, and their uses. Note that wt% means weight percent, and A to B means A or more and B or less (the same applies hereinafter).

[0042] In the above general formulas (1), (1a), and (1b), R 3 Each of these independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a bromine atom.

[0043] R 3 The alkyl group having 1 to 4 carbon atoms in this compound is not particularly limited, but examples include methyl, ethyl, propyl, isopropyl, cyclopropyl, butyl, isobutyl, sec-butyl, or tert-butyl groups.

[0044] From the viewpoint of excellent productivity of isocyanate compounds represented by the above general formula (1), (1a), or (1b), R 3 Each of these is preferably independently a hydrogen atom, a methyl group, or a bromine atom, and more preferably independently a hydrogen atom or a bromine atom.

[0045] Note, R 3 However, if each atom is independently a hydrogen atom or a bromine atom, then the above general formula (1) can be rewritten as the following general formula (1').

[0046] [ka]

[0047] (In the above general formula, R 1 and R 2Each of the following independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. m represents at least one selected from the group consisting of 0, 1, 2, and 3. n independently represents a real number of 0 or greater. -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 a state where a real number (k) of bromine atoms corresponding to Ywt% is bonded to the aromatic ring carbon atom. In the above general formula (1'), -Br represents a bromine atom bonded to the aromatic ring, but this does not mean that there is one bromine atom; rather, it means that there are a number of bromine atoms bonded that satisfy the Ywt% described later. Ywt% represents the bromine content in the isocyanate compound represented by the above general formula (1') (which may be a single compound or a mixture of multiple compounds), and as described above, it is preferably 38 to 78 wt%.

[0048] Furthermore, with respect to the isocyanate compound represented by the above general 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), it is preferable that the isocyanate compound represented by the above general 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) is preferable in terms of its excellent ability to capture active hydrogen-containing organic compounds, and it is more preferable that the isocyanate compound represented by the above general 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) is preferable.

[0049] In the above general formulas (1), (1'), (1a), and (1b), R 1 and R 2 Each of these independently represents either a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

[0050] R 1 and R 2The alkyl group having 1 to 4 carbon atoms in this compound is not particularly limited, but examples include methyl, ethyl, propyl, isopropyl, cyclopropyl, butyl, isobutyl, sec-butyl, or tert-butyl groups.

[0051] From the viewpoint of superior productivity of the above-mentioned isocyanate compounds, R 1 and R 2 Each of these is preferably a hydrogen atom or a methyl group, and more preferably a hydrogen atom.

[0052] In general formulas (1), (1'), (1a), and (1b), n represents a real number greater than or equal to 0. From the viewpoint of excellent productivity of the isocyanate compound represented by general formulas (1), (1'), (1a), or (1b), n is preferably a real number greater than 0, more preferably a real number greater than 0.1, and more preferably a real number greater than 0.3. Furthermore, from the viewpoint of excellent productivity of the isocyanate compound represented by general formulas (1), (1'), (1a), or (1b), n is preferably a real number of 10 or less, more preferably a real number of 6 or less, more preferably a real number of 3 or less, and more preferably a real number of 2 or less.

[0053] With respect to n, it is preferably a real number between 0 and 10, more preferably a real number between 0 and 6, more preferably a real number greater than 0 and 6 or less, more preferably a real number greater than 0.1 and 3, more preferably a real number greater than 0.3 and 2 or less, and it is even more preferably a real number between 0 and 3, and more preferably a real number between 0 and 2, with respect to excellent productivity of isocyanate compounds represented by general formulas (1), (1'), (1a), or (1b).

[0054] Note that when n is 0, it means that the base enclosed by [ ]n in general formulas (1), (1'), (1a), or (1b) no longer exists.

[0055] In general formulas (1), (1'), and (1a), m represents at least one selected from the group consisting of 0, 1, 2, and 3. That is, the isocyanates represented by the above general formulas (1), (1'), or (1a) may be, for example, a single isocyanate with m=0, or a mixture containing the components m=0, m=1, m=2, and m=3.

[0056] With respect to m, from the viewpoint of excellent productivity of isocyanate compounds represented by general formula (1), (1'), or (1a), it is preferable that m be at least one selected from the group consisting of 0, 1, and 2, more preferably at least one selected from the group consisting of 0 and 1, and more preferably 0 or 1.

[0057] When m is 0, it means that there are no groups enclosed in [ ]m in general formulas (1), (1'), or (1a). When m is 3, it means that there are three groups enclosed in [ ]m, each bonded to the fundamental benzene ring.

[0058] When m is 2 or 3, the general formula implies that there are two or three n values, but the range of n can be clearly expressed by defining its average value.

[0059] Here, for example, an isocyanate with m=0 (i.e., n=0) can be described as a mononuclear body, an isocyanate with m=1 and n=1 can be described as a dinuclear body, an isocyanate with m=1 and n=2 can be described as a trinuclear body, an isocyanate with m=1 and n=3 or an isocyanate with m=3 and three n=1 (average value) can be described as a tetranuclear body, and an isocyanate with m=1 and n=4 or an isocyanate with m=3 and n=1.33 (average value represented by 4 / 3) can be described as a pentanuclear body.

[0060] The general formulas for mononuclear to pentanuclear structures included in general formula (1), etc., are not particularly limited, but examples are given below.

[0061] [ka]

[0062] In each of the above general formulas, R 1 , R 2 , and R 3 The definition and preferred range are as stated above.

[0063] The isocyanate compound of the present invention may be a single compound, or it may be a mixture of isocyanate compounds represented by general formulas (1), (1'), (1a), or (1b) having different combinations of m and n. In the case of a mixture of isocyanate compounds represented by general formulas (1), (1'), (1a), or (1b), n is treated as the average value derived from each component of the mixture, and therefore may be a real number rather than an integer.

[0064] In other words, the isocyanate compound of the present invention may be mononuclear only, dinuclear only, trinuclear only, a mixture of mononuclear and dinuclear, a mixture of mononuclear, dinuclear and trinuclear, a mixture of mononuclear, dinuclear and tetranuclear, or a mixture of tetranuclear or more, and is not limited to these.

[0065] Furthermore, when the isocyanate compound represented by the above general formulas (1), (1'), (1a), or (1b) is a mixture of multiple nuclei, it is preferable that each of the nuclei satisfies the specified range for its bromine content (corresponding to Ywt%) in general formula (1'). However, it is not necessarily required that each of the nuclei satisfies the specified range; it is sufficient that the mixture as a whole satisfies the specified range. That is, for example, the compound of the present invention can be produced by mixing a dinuclear compound with a bromine content below the specified lower limit and a trinuclear compound with a bromine content above the specified upper limit in a ratio such that the bromine content falls within the specified range.

[0066] Furthermore, the isocyanate compounds represented by the above general formulas (1), (1'), (1a), or (1b) are preferably mononuclear, dinuclear, trinuclear, tetranuclear, or mixtures of multiple nuclear compounds, in terms of excellent supply stability. In the case of a mixture of multiple nuclear compounds, the relative abundance of each nucleus is not particularly limited, but it is preferable that mononuclear compounds make up 0-20%, dinuclear compounds 10-99%, trinuclear compounds 5-60%, and tetranuclear compounds or more make up 0-30%.

[0067] Here, the abundance ratio [%] of each nucleus mentioned above represents the GPC area %. The measurement conditions for the GPC area % are as follows.

[0068] A Tosoh Corporation HLC-8320GPC GPC analyzer was used. Tosoh Corporation columns TSKgel guardcolumn SuperAW-H, TSKgel SuperAW2500, TSKgel SuperAW2500, TSKgel SuperAW3000, and TSKgel SuperAW3000 were used in series in that order, with the column temperature set to 40°C. Tetrahydrofuran (THF) was used as the eluent at a flow rate of 0.6 mL / min, and a UV-Vis absorbance detector set to 254 nm was used. Data processing was performed using Tosoh Corporation GPC-8020 Model II version 4.10. For the measurement sample, 0.1 g of the sample was dissolved in 10 mL of THF, filtered through a microfilter, and 10 μL of the resulting sample was used. The obtained chromatogram allows for the calculation of the content of mononuclear, dinuclear, trinuclear, tetranuclear, and pentanuclear or more nuclei.

[0069] When the isocyanate compound represented by the above general formula (1), (1'), (1a), or (1b) is a mixture of multiple compounds (a mixture of multiple nuclei), the above n is expressed as the average value (real number) of the mixture, and this average value can be calculated using the abundance ratio [GPC area %] of each nucleus mentioned above.

[0070] For example, if the abundance ratio of dinuclear cells (m=1, n=1) is 50 [GPC area %] and the abundance ratio of trinuclear cells (m=1, n=2) is 50 [GPC area %], the average value of n is calculated as (1 × 0.5 + 2 × 0.5) = 1.5.

[0071] In general formula (1'), k represents a real number in the range 1 to [5-m+m×(3×n+1)] (i.e., a real number in the range 1 to [5+3×m×n]). For example, when m=0 (i.e., n=0), k represents a real number from 1 to 5; when m=1 and n=1, k represents a real number from 1 to 8; and when m=1 and n=2, k represents a real number from 1 to 11.

[0072] The value of k represents a real number because n is a real number, and because the number of bromine atoms added when producing the isocyanate compounds represented by the general formulas (1), (1'), (1a), or (1b) above is not necessarily uniform across all molecules. For example, if there are 50 / 50 molecules with m=n=0 and one added bromine atom, and 50 / 50 molecules with m=n=0 and two added bromine atoms, then k will be a real number of approximately 1.5.

[0073] The bromine content (Ywt%) in the isocyanate compound represented by general formula (1), (1'),(1a), or (1b) is characterized by being 38 to 78 wt%. From the viewpoint of increasing the capture selectivity of active hydrogen-containing organic compounds such as alcohol compounds, the bromine content is preferably 45 to 78 wt%, more preferably 50 to 78 wt%, and even more preferably 55 to 78 wt%. The bromine content (Ywt%) in the isocyanate compound represented by general formula (1), (1'),(1a), or (1b) is the result of measurement by the oxygen flask combustion-IC method.

[0074] There is a certain correlation between the bromine content (Ywt%) in general formula (1') and the real number k mentioned above. The range of k above represents the maximum number of bromine atoms that the isocyanate compound represented by general formula (1') can take.

[0075] Isocyanate compounds represented by general formulas (1), (1'), (1a), or (1b) can be produced by isocyanating the corresponding amine compounds. For example, patent document (GB971168) discloses the production of aromatic isocyanate compounds containing a bromine atom.

[0076] The isocyanate compound represented by general formula (1), (1a), or (1b) (which may be a single compound or a mixture of multiple compounds) is not particularly limited, but for example, it can be produced by using an amine compound represented by the following general formula (2), (2a), or (2b) as a precursor (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) and converting the amino group of the amine compound to an isocyanate group.

[0077] [ka]

[0078] (In the above general formula, R 1 and R 2 Each of these independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. 3 Each of these independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a bromine atom. m represents at least one selected from the group consisting of 0, 1, 2, and 3. n represents a real number greater than or equal to 0.

[0079] [ka]

[0080] (In the above general formula, R 1 and R 2 Each of these independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. 3Each of these independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a bromine atom. m represents at least one selected from the group consisting of 0, 1, 2, and 3. n represents a real number greater than or equal to 0.

[0081] [ka]

[0082] (In the above general formula, R 1 and R 2 Each of these independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. 3 Each of these independently represents a hydrogen atom, an alkyl group with 1 to 4 carbon atoms, or a bromine atom. n represents a real number greater than or equal to 0. In the above general formulas (2), (2a), or (2b), R 1 , R 2 , R 3 The definitions and preferred ranges of , n, and m are as follows: R in the general formula (1) above. 1 , R 2 , R 3 This is synonymous with the definitions and preferred ranges of n and m.

[0083] While it is difficult to specify a general bromine content (wt%) for general formulas (2), (2a), or (2b), it is preferable that each theoretically satisfies the requirements for the bromine content (wt%) in general formulas (1), (1a), or (2b).

[0084] The amine compounds represented by the above general formulas (2), (2a), or (2b) are not particularly limited, but examples include brominated aniline, brominated 4,4'-methylenedianiline, brominated 2,2'-bis(4-aminophenyl)propane, brominated polymer products of aniline and formalin, or brominated polymer products of aniline and acetone.

[0085] The amine compounds represented by the above general formulas (2), (2a), or (2b) can be used as commercially available products, or they can be produced by brominating aniline, 4,4'-methylenedianiline, 2,2'-bis(4-aminophenyl)propane, polymerization products of aniline and formalin, or polymerization products of aniline and acetone using generally known methods. They can also be produced as polymerization products of brominated aniline and formalin, or brominated aniline and acetone.

[0086] Next, we will describe active hydrogen-containing organic compound scavengers or compositions containing isocyanate compounds represented by the above general formulas (1), (1'), (1a), or (1b).

[0087] Generally, isocyanate compounds such as diphenylmethane diisocyanate (MDI) and tolylene diisocyanate (TDI) (isocyanate compounds different from those represented by the general formulas (1), (1'), (1a), or (1b) above) are used as raw materials for the manufacture of polyurethanes. This utilizes the fundamental property that isocyanate groups react with nucleophilic functional groups (so-called groups having active hydrogen, such as hydroxyl groups and amino groups). Conventional isocyanate compounds are highly reactive and react with moisture in the air even at temperatures around room temperature (15°C to 40°C), resulting in low storage stability under atmospheric conditions.

[0088] In contrast to such conventional technologies, the isocyanate compounds represented by the above general formulas (1), (1'), (1a), or (1b) have high water resistance and are characterized by extremely slow reaction with water in a temperature environment around room temperature (15°C to 40°C). On the other hand, they are characterized by reacting with active hydrogen-containing organic compounds such as alcohol compounds in a temperature environment around room temperature (15°C to 40°C). In other words, the isocyanate compounds represented by the above general formulas (1), (1'), (1a), or (1b) react with high selectivity with active hydrogen-containing organic compounds such as alcohol compounds in the presence of water and such active hydrogen-containing organic compounds. By making good use of this characteristic, an active hydrogen-containing organic compound scavenger containing an isocyanate compound represented by the above general formula (1), (1'), (1a), or (1b), or a composition containing an isocyanate compound represented by the above general formula (1), (1'), (1a), or (1b) and a carrier, can be used as a scavenger for active hydrogen-containing organic compounds such as alcohol compounds that have a sustained effect in the living environment.

[0089] The organic compounds containing active hydrogen that are to be captured are not particularly limited, but include, for example, alcohol compounds, thiol compounds, amine compounds, phenol compounds, or carboxylic acid compounds. More specific examples, not particularly limited, include, for example, primary alcohols such as 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, 2-propanol, 2-butanol, 2-pentanol, 3-pentanol, 2-hexanol, cyclohexanol, and 2,2,4-trimethylphenyl Examples include secondary alcohols such as tan-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 glycerin, amines such as methylamine, dimethylamine, ethylamine, diethylamine, butylamine, hexylamine, octylamine, ethanolamine, diethanolamine, ethylenediamine, diethylenetriamine, and hexamethylenediamine, thiol compounds such as methyl mercaptan, ethyl mercaptan, propyl mercaptan, butyl mercaptan, hexyl mercaptan, and thiophenol, carboxylic acids such as formic acid, acetic acid, and propionic acid, and phenolic compounds such as phenol and salicylic acid.

[0090] Among these active hydrogen-containing organic compounds, alcohol compounds or carboxylic acid compounds are preferred because they are difficult to capture using conventional techniques and provide the remarkably unique effects of the present invention.

[0091] The state of the active hydrogen-containing organic compound to be captured can be solid, liquid, or gaseous. However, to efficiently capture the active hydrogen-containing organic compound, it is necessary to increase the frequency of contact with the isocyanate compound represented by the general formulas (1), (1'), (1a), or (1b) above, so it is preferable that it be in a liquid or gaseous state. The active hydrogen-containing organic compound to be captured may also be dissolved in a solvent. There are no particular limitations on the solvents that can be used, but examples include aqueous solvents, hydrocarbon solvents, halogenated solvents, aromatic solvents, ether solvents, etc.

[0092] The isocyanate compounds represented by general formulas (1), (1'), (1a), or (1b) are liquid or solid at room temperature. The isocyanate compounds represented by general formulas (1), (1'), (1a), or (1b) themselves can be used as scavengers in liquid or solid form, or the solid isocyanate compounds represented by general formulas (1), (1'), (1a), or (1b) can be ground into a powder using a mortar and pestle or similar device and used in powder form, or the powder can be further compressed into a mass and used in that form. All of these are active hydrogen-containing organic compound scavengers of the present invention.

[0093] A composition comprising an isocyanate compound represented by the above general formula (1) having a bromine content of 38-78 wt% and a carrier (hereinafter also referred to as "the composition of the present invention") also exhibits the effect of an active hydrogen-containing organic compound scavenger as targeted by the present invention. In this case, it is preferable that the isocyanate compound represented by the above general formula (1) is supported on the carrier.

[0094] In the compositions of the present invention described above, the isocyanate compound represented by the above general formula (1) having a bromine content of 38 to 78 wt% is preferably an isocyanate compound represented by the above general formula (1') having a bromine content (Y wt%) of 38 to 78 wt%, more preferably an isocyanate compound represented by the above general formula (1a) having a bromine content of 38 to 78 wt%, and even more preferably an isocyanate compound represented by the above general formula (1b) having a bromine content of 38 to 78 wt%.

[0095] In the compositions of the present invention described above, the bromine content in the isocyanate compound represented by the general formula (1), (1'), (1a), or (1b) is preferably 45 to 78 wt%, more preferably 50 to 78 wt%, and more preferably 55 to 78 wt%, from the viewpoint of increasing the capture selectivity of active hydrogen-containing organic compounds such as alcohol compounds. The bromine content in the present invention (Y wt%) in general formula (1') is measured by the oxygen flask combustion-IC method.

[0096] Furthermore, the aforementioned carriers are not particularly limited, but examples include activated carbon, activated clay, diatomaceous earth, porous resin, nonwoven fabric, mesoporous silica, silica gel, aluminosilicate, hydrotalcite, zeolite, activated alumina, titania, magnesia, or zirconia. Among these carriers, activated carbon, nonwoven fabric, silica gel, or hydrotalcite are preferred in terms of their excellent scavenging performance, with silica gel or hydrotalcite being more preferred.

[0097] When an isocyanate compound represented by general formula (1), (1'), (1a), or (1b) is supported on a carrier, the relevant isocyanate compound can be dissolved in an organic solvent, mixed with the carrier, and then subjected to an organic solvent removal procedure. In this case, it is preferable to use an organic solvent that does not contain active hydrogen, and although not particularly limited, examples include hexane, dichloromethane, chloroform, acetone, tetrahydrofuran, dioxane, benzene, chlorobenzene, toluene, or xylene.

[0098] The compositions of the present invention described above may further contain clays such as styrene-butadiene rubber, polyvinylidene fluoride, polytetrafluoroethylene, sepiolite, and attapulgite, as well as binders such as sodium silicate and silica sol.

[0099] The amount of isocyanate compound represented by the above general formula (1), (1'), (1a), or (1b) to be supported on a carrier is not particularly limited, but for example, each is preferably 0.1 to 60 parts by weight per 100 parts by weight of the carrier, more preferably 0.5 to 40 parts by weight per 100 parts by weight of the carrier, and more preferably 1 to 25 parts by weight per 100 parts by weight of the carrier.

[0100] As described above, the isocyanate compounds represented by the above general formulas (1), (1'), (1a), or (1b) can be used as scavenging agents in powder or lump form, or they can be used as scavenging agents containing a carrier or supported on a carrier. From the viewpoint of improving the scavenging effect of active hydrogen-containing organic compounds, it is preferable to use them as scavenging agents supported on a carrier such as silica gel, zeolite, alumina, hydrotalcite, or activated carbon.

[0101] In the present invention, the temperature at which an active hydrogen-containing organic compound is captured using the active hydrogen-containing organic compound scavenger or composition of the present invention described above is not particularly limited, but any temperature in the range of 0 to 150°C is acceptable. From the viewpoint of selectively capturing active hydrogen-containing organic compounds such as alcohol compounds, a temperature range of 10 to 100°C is preferred, and a temperature range of 20 to 70°C is more preferred.

[0102] The active hydrogen-containing organic compound scavenger or 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 composition of the present invention can be captured by contacting at least one compound selected from the group consisting of alcohol compounds, thiol compounds, amine compounds, phenol compounds, and carboxylic acid compounds with the active hydrogen-containing organic compound scavenger or composition of the present invention described above.

[0103] Furthermore, these target compounds (active hydrogen-containing organic compounds) are preferably generated in the natural or living environment, and the factors causing their generation may be anthropogenic or non-anthropogenic.

[0104] Among these target compounds (active hydrogen-containing organic compounds), alcohol compounds or carboxylic acid compounds are preferred because they are difficult to capture using conventional techniques, and the distinctive effects of the present invention can be obtained. [Brief explanation of the drawing]

[0105] [Figure 1] A schematic diagram of the apparatus used in the example to evaluate the amount of active hydrogen-containing organic compounds captured is shown. [Examples]

[0106] The present invention will be described in detail below with reference to examples. However, the present invention is not limited thereto. [GCMS analysis] Measurement device: HERACLES II electronic olfactory system manufactured by AlphaMos Japan Co., Ltd. Measurement conditions: Column = Agilent J&W GC column DB-5 Evaporation chamber temperature = 220℃ Detection unit temperature = 260℃ Column temperature = 250°C Heating rate = 1.5°C / second [FT-IR analysis] Measurement device: PerkinElmer Frontier MIR / NIR Measurement conditions: ATR method, MIR mode [Quantitative determination of bromine content] Combustion method: Oxygen flask combustion method (according to ISO 7725-2020) Measuring device: Tosoh Corporation IC-2001 Synthesis Example 1

[0107] [ka]

[0108] 100 g of a 4,4'-methylenedianiline composition (nuclear distribution: dinuclear = 65%, trinuclear = 23%, tetranuclear = 8%, pentanuclear or more = 4%) obtained by the condensation reaction of aniline and formalin, 5.00 g of iron trichloride, 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 2 L separable flask over 1 hour with stirring. After the addition was complete, the internal temperature rose to 50°C, and the mixture was stirred for 1 hour while cooling at room temperature. Then, unreacted bromine was removed with an aqueous hydrazine solution, and the pH was confirmed to be basic. Next, the mixture was separated into a 1,2-dichloroethane layer and an aqueous layer, and a pale red solid was precipitated by adding the 1,2-dichloroethane layer dropwise to methanol. This solid was filtered, washed with methanol, and finally dried to obtain 153 g of a pale red solid (brominated 4,4'-methylenedianiline composition). The bromine content of this solid was quantified by oxygen flask combustion-IC method and found to be 59.6% by weight.

[0109] Synthesis Example 2

[0110] [ka]

[0111] Under a nitrogen atmosphere, 12.5 g of the pale red solid obtained in Synthesis Example 1 (brominated 4,4'-methylenedianiline composition) and 987.5 g of chlorobenzene were added to a 2 L separable flask equipped with a stirrer, and the mixture was heated to 130°C. 13.4 g of hydrochloric acid gas was blown into this solution over 90 minutes to carry out the salt formation reaction. Next, 44 g of phosgene gas was blown in over 2 hours. The mixture was then aged at 125°C for 2 hours, followed by phosgene removal from the system by bubbling with nitrogen gas. After confirming that no phosgene residue remained, the reaction mixture was returned to room temperature, and insoluble matter was removed by filtration. The filtrate was concentrated using an evaporator, and the concentrate was air-dried at 45°C to obtain 12.4 g (79% yield) of 4,4'-methylenebis(2,6-dibromo-isocyanatobenzene) (dinuclear) and an oligomer mixture of the same compound (including trinuclear, tetranuclear, and pentanuclear or more; hereinafter abbreviated as Synthesis Example 2 compound) as a brown powder. 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. This Synthesis Example 2 compound can be used as an active hydrogen-containing organic compound scavenger of the present invention, as described below.

[0112] Synthesis Example 3 Under a nitrogen atmosphere, 30.0 g of 4,4'-methylenebis(2-bromoaniline) (nuclear distribution: dinuclear = 100%) and 1470.0 g of chlorobenzene were added to a 2 L separable flask equipped with a stirrer, and the mixture was heated to 130°C. 12.3 g of hydrochloric acid gas was blown into this solution over 120 minutes to carry out the salt formation reaction. Next, 109.6 g of phosgene gas was blown in over 6 hours. Afterward, phosgene was removed from the system by bubbling with nitrogen gas. After confirming that no phosgene residue remained, the reaction mixture was returned to room temperature, and insoluble matter was removed by filtration. The filtrate was concentrated using an evaporator, and the concentrate was air-dried at 45°C to obtain 33.0 g of 4,4'-methylenebis(2-bromo-isocyanatobenzene) as a white powder (yield 96%) (hereinafter abbreviated as Synthesis Example 3 compound). The NCO content (mass of isocyanate groups relative to the total mass) was 21.0% by mass, and the bromine content was 39.1% by weight. As described below, the compound in this synthesis example 3 can be used as an active hydrogen-containing organic compound scavenger of the present invention.

[0113] Synthesis Example 4 5.00 g of a 4,4'-methylenedianiline composition (nuclear distribution: dinuclear = 65%, trinuclear = 23%, tetranuclear = 8%, pentanuclear or more = 4%), 0.25 g of ferric trichloride, 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 200 mL separable flask over 1 hour with stirring. From this point onward, the same procedure as in Synthesis Example 1 was followed to obtain 12.0 g of a reddish-brown solid (brominated 4,4-methylenedianiline composition) (hereinafter abbreviated as Synthesis Example 4 compound). The bromine content of this solid was quantified by oxygen flask combustion-IC method and found to be 58.5% by weight.

[0114] Synthesis Example 5 10.0 g of 4,4'-methylenedianiline (nuclear distribution: dinuclear = 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 200 mL separable flask over 1 hour with stirring. From this point onward, the same procedure as in Synthesis Example 1 was followed to obtain 25.5 g of a beige solid (brominated 4,4-methylenedianiline) (hereinafter abbreviated as Synthesis Example 5 compound). The bromine content of this solid was quantified by oxygen flask combustion-IC method and found to be 59.4% by weight.

[0115] Synthesis Example 6 Under a nitrogen atmosphere, 39.8 g of Synthesis Example 5 compound (nuclear distribution: dinuclear = 100%) and 1150.0 g of orthochlorobenzene 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 this solution over 120 minutes to carry out the salt formation reaction. Next, 61.3 g of phosgene gas was blown in over 4 hours. Afterward, nitrogen gas was bubbled to remove phosgene from the system. After confirming that no phosgene residue remained, the reaction mixture was returned to room temperature, concentrated using an evaporator, and the concentrate was air-dried at 45°C to obtain 42.7 g of 4,4'-methylenebis(2,6-dibromo-isocyanatobenzene) as a brown powder (hereinafter abbreviated as Synthesis Example 6 compound). 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. The compound in the six synthesis examples can be used as an active hydrogen-containing organic compound scavenger according to the present invention.

[0116] Synthesis Example 7 Under a nitrogen atmosphere, 50.0 g of 4,4'-methylenebis(3-bromoaniline) (nuclear distribution: dinuclear = 45%, trinuclear = 18%, tetranuclear = 17%, pentanuclear or more = 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 bubbled into this solution over 120 minutes to carry out the salt formation reaction. Next, 110.0 g of phosgene gas was bubbled in over 6 hours. Afterward, phosgene was removed from the system by bubbling with nitrogen gas. After confirming that no phosgene residue remained, the reaction mixture was allowed to return 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 air-dried at 45°C to obtain 40.7 g of 4,4'-methylenebis(3-bromo-isocyanatobenzene) as a brown powder (hereinafter abbreviated as Synthesis Example 7 compound). The bromine content was 38.3% by weight. Synthesis Example 7 compound can be used as an active hydrogen-containing organic compound scavenger of the present invention, as described below.

[0117] The synthesized isocyanate compounds and the isocyanate compound (2,4,6-tribromoisocyanatobenzene) used in Example 5 are shown in the table below.

[0118] [Table 1]

[0119] Example 1 In a 200 mL round-bottom flask, a stirring bar, 1.0 g of Compound 2 (Synthesis Example 2), 9.0 g of activated carbon granular Shirasagi KL (manufactured by Osaka Gas Chemical Co., Ltd.), and 40 mL of tetrahydrofuran were added and stirred at room temperature for 30 minutes. After removing the stirring bar, the solvent was removed by filtration. The resulting solid was heated and vacuum-dried at 100 °C for 8 hours to obtain 10.0 g of the activated carbon-supported product of Compound 2 (the composition of the present invention and the active hydrogen-containing organic compound scavenger of the present invention).

[0120] Example 2 In a 200 mL round-bottom flask, a stirring bar, 1.0 g of Compound 2 (Synthesis Example 2), 9.0 g of granular activated carbon Shirasagi WH2C8 / 32 (manufactured by Osaka Gas Chemical Co., Ltd.), and 40 mL of tetrahydrofuran were added and stirred at room temperature for 30 minutes. After removing the stirring bar, the solvent was removed by filtration. The resulting solid was heated and vacuum-dried at 100 °C for 8 hours to obtain 10.0 g of the activated carbon-supported product of Compound 2 (the composition of the present invention and the active hydrogen-containing organic compound scavenger of the present invention).

[0121] Example 3 In a 200 mL round-bottom flask, a stirring bar, 1.0 g of Compound Example 2, 9.0 g of activated carbon granular Shirasagi X7100H-3DRY (manufactured by Osaka Gas Chemical Co., Ltd.), and 40 mL of tetrahydrofuran were added and stirred at room temperature for 30 minutes. After removing the stirring bar, the solvent was removed by filtration. 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 (the composition of the present invention and the active hydrogen-containing organic compound scavenger of the present invention) as a black powder.

[0122] Example 4 20 mg of the two compound examples (active hydrogen-containing organic compound scavenger of the present invention), which had been ground 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 gas), and left 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 (HERACLES II electronic olfactory system, AlphaMoss Japan), and it was found that 81% of the 2-ethyl-1-hexanol had been captured and removed. Subsequently, the inside of the vial was replaced with nitrogen gas, heated at 60°C for 30 minutes, and then quantitatively analyzed for 2-ethyl-1-hexanol by GCMS. The re-release rate of the captured 2-ethyl-1-hexanol was 0%.

[0123] Example 5 20 mg of 2,4,6-tribromoisocyanatobenzene (synthesized by isocyanation of 2,4,6-tribromoaniline (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), bromine content 67.1% by weight) (fine powder form, the active hydrogen-containing organic compound scavenger of the present invention) 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 left 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 (electronic olfactory system HERACLES II, manufactured by AlphaMoss Japan Co., Ltd.), and it was found that 90% of the 2-ethyl-1-hexanol had been captured and removed. Next, the inside of the vial, after standing, was replaced with nitrogen gas and heated at 60°C for 30 minutes. Quantitative analysis of 2-ethyl-1-hexanol was then performed by GC-MS, and the re-release rate of the captured 2-ethyl-1-hexanol was found to be 0%.

[0124] Example 6 In Example 4, the same procedure as in Example 4 was performed, except that instead of using a gas containing 10 ppm of 2-ethyl-1-hexanol (the remainder being nitrogen gas), a gas containing 10 ppm of 2-methyl-1-butanol (the remainder being nitrogen gas) was used. When the capture and re-release evaluation was performed, the capture and removal rate of 2-methyl-1-butanol was 89%, and the re-release rate was 0%.

[0125] Example 7 In Example 4, the same procedure as in Example 4 was performed, except that instead of using a gas containing 10 ppm of 2-ethyl-1-hexanol (the remainder being nitrogen gas), a gas containing 10 ppm of 2-methyl-1-propanol (the remainder being nitrogen gas) was used. When the capture and re-release evaluation was performed, the capture and removal rate of 2-methyl-1-propanol was 48%, and the re-release rate was 0%.

[0126] Comparative Example 1 In Example 4, the same procedure as in Example 4 was performed except that 20 mg of the compound from Synthesis Example 2 was not added (an empty glass vial was filled with a gas containing 10 ppm of 2-ethyl-1-hexanol (the remainder being nitrogen gas)), and when a capture evaluation was performed, the capture and removal rate of 2-ethyl-1-hexanol was 0%.

[0127] Comparative Example 2 In Example 4, the same procedure as in Example 4 was performed, except that 20 mg of β-cyclodextrin (manufactured by Tokyo Chemical Industry Co., Ltd.) was used instead of 20 mg of the compound from Synthesis Example 2. When the capture evaluation was performed, the capture and removal rate of 2-ethyl-1-hexanol was 0%.

[0128] Comparative Example 3 In Example 4, the same procedure as in Example 4 was performed, except that 5 mg of activated carbon (special grade powder product manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) was used instead of 20 mg of the compound from Synthesis Example 2. When the capture and re-release evaluation was performed, the capture and removal rate of 2-ethyl-1-hexanol was 99%, and the re-release rate was 13%.

[0129] Comparative Example 4 In Example 4, the same procedure as in Example 4 was followed, except that 5 mg of activated carbon (special grade powder product manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) was used instead of 20 mg of the compound from Synthesis Example 2, and 10 ppm of 2-methyl-1-butanol (the remainder being nitrogen gas) was used instead of a gas containing 10 ppm of 2-ethyl-1-hexanol (the remainder being nitrogen gas). When the capture and re-release evaluation was performed, the capture and removal rate of 2-methyl-1-butanol was 92%, and the re-release rate was 6%.

[0130] Comparative Example 5 In Example 4, the same procedure as in Example 4 was performed, except that 5 mg of activated carbon (special grade powder product manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) was used instead of 20 mg of the compound from Synthesis Example 2, and a gas containing 10 ppm of 2-methyl-1-propanol (the remainder being nitrogen gas) was used instead of a gas containing 10 ppm of 2-ethyl-1-hexanol (the remainder being nitrogen gas). When the capture and re-release evaluation was performed, the capture and removal rate of 2-methyl-1-propanol was 95%, and the re-release rate was 12%.

[0131] Comparative Example 6 In Example 4, the same procedure as in Example 4 was performed, except that 5 mg of CARiACT Q-50 (manufactured by Fuji Silysia Chemical Co., Ltd.) was used instead of 20 mg of the compound from Synthesis Example 2. When the capture and re-release evaluation was performed, the capture and removal rate of 2-ethyl-1-hexanol was 86%, and the re-release rate was 25%.

[0132] Comparative Example 7 In Example 4, the same procedure as in Example 4 was performed, except that 5 mg of silica gel NIPGEL AY-001 (manufactured by Tosoh Silica Co., Ltd.) was used instead of 20 mg of the compound from Synthesis Example 2. When the capture and re-release evaluation was performed, the capture and removal rate of 2-ethyl-1-hexanol was 92%, and the re-release rate was 21%.

[0133] [Table 2]

[0134] Example 8 A stirring bar, 30 mg of Compound 2 (the active hydrogen-containing organic compound scavenger of the present invention), and 10 mL of water were added to a 20 mL vial. The vial was sealed with the lid closed and stirred at room temperature for 3 months. After that, the water was removed by filtration, and the resulting brown powder was subjected to FT-IR analysis. According to the analysis, there was no change in peak intensity or pattern compared to before the test, indicating that there was no degradation by water over the long term. The results are shown in Table 3.

[0135] Example 9 A stirring bar and 100 mg of Synthesis Example 2 compound (the active hydrogen-containing organic compound scavenger of the present invention) were added to a 20 mL vial. The mixture was stirred at 60°C for 2 months in an air atmosphere without closing the lid. Subsequently, the resulting brown powder was subjected to FT-IR analysis. The analysis showed no change in peak intensity or pattern compared to before the test, indicating that hydrolysis of the isocyanate group by trace amounts of moisture in the air did not occur over a long period, even under heated conditions. The results are shown in Table 3.

[0136] Example 10 A stirring bar, 30 mg of Synthesis Example 2 compound (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 with the lid closed and stirred at 45°C for 3 days. After that, the solvent was removed by filtration, and the resulting brown powder was subjected to FT-IR analysis. According to the analysis, compared to before the test, the isocyanate group peak disappeared, and instead, a carbonyl group peak derived from the reaction product of ethanol and the isocyanate group was observed. No peak changes due to hydrolysis were observed. That is, the isocyanate group of Synthesis Example 2 compound did not react with water but reacted selectively with ethanol. The results are shown in Table 3.

[0137] Example 11 A stirring bar, 30 mg of Compound Example 2 (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 with the lid closed and stirred at 45°C for 3 days. The toluene layer was then concentrated to dryness, and the resulting brown powder was subjected to FT-IR analysis. The analysis showed that, compared to before the test, the isocyanate group peak disappeared, and instead, a carbonyl group peak derived from the reaction product of ethanol and the isocyanate group was observed. No peaks derived from hydrolysis were observed. That is, the isocyanate group of Compound Example 2 did not react with water but reacted selectively with ethanol. The results are shown in Table 3.

[0138] Example 12 A stirring bar, 30 mg of the compound from Synthesis Example 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 with the lid closed 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 revealed that the isocyanate group peak disappeared, and instead, the carbonyl group peak was observed. This suggests that the isocyanate group reacted with ethanol and scavenged it. Furthermore, no peak changes due to hydrolysis were observed. That is, the isocyanate group of the compound from Synthesis Example 3 did not react with water but reacted selectively with ethanol. The results are shown in Table 3.

[0139] Example 27 A stirring bar, 30 mg of compound 6 (the active hydrogen-containing organic compound scavenger of the present invention), and 10 mL of water were added to a 20 mL vial. The vial was sealed with the lid closed and stirred at room temperature for 3 months. After that, the water was removed by filtration, and the resulting brown powder was subjected to FT-IR analysis. According to the analysis, there was no change in peak intensity or pattern compared to before the test, indicating that there was no degradation by water over the long term. The results are shown in Table 3.

[0140] Example 28 A stirring bar and 100 mg of Synthesis Example 6 compound (the active hydrogen-containing organic compound scavenger of the present invention) were added to a 20 mL vial. The mixture was stirred at 60°C for 2 months in an air atmosphere without closing the lid. Subsequently, the resulting brown powder was subjected to FT-IR analysis. The analysis showed no change in peak intensity or pattern compared to before the test, indicating that hydrolysis of the isocyanate group by trace amounts of moisture in the air did not occur over a long period, even under heated conditions. The results are shown in Table 3.

[0141] Example 29 A stirring bar, 30 mg of Synthesis Example 6 compound (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 with the lid closed and stirred at 45°C for 3 days. After that, the solvent was removed by filtration, and the resulting brown powder was subjected to FT-IR analysis. According to the analysis, compared to before the test, the isocyanate group peak disappeared, and instead, a carbonyl group peak derived from the reaction product of ethanol and the isocyanate group was observed. No peak changes due to hydrolysis were observed. That is, the isocyanate group of Synthesis Example 6 compound did not react with water but reacted selectively with ethanol. The results are shown in Table 3.

[0142] Example 30 A stirring bar, 30 mg of Synthesis Example 6 compound (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 with the lid closed and stirred at 45°C for 3 days. The toluene layer was then concentrated to dryness, and the resulting brown powder was subjected to FT-IR analysis. The analysis showed that, compared to before the test, the isocyanate group peak disappeared, and instead, a carbonyl group peak derived from the reaction product of ethanol and the isocyanate group was observed. No peaks derived from hydrolysis were observed. That is, the isocyanate group of Synthesis Example 6 compound did not react with water but reacted selectively with ethanol. The results are shown in Table 3.

[0143] Comparative Example 8 A stirring 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 revealed significant changes in peak intensity and pattern compared to before the test. Specifically, the polymeric MDI was decomposed by water. The results are shown in Table 3.

[0144] Comparative Example 9 A stirring 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 open and stirred at 60°C for 14 days in an air atmosphere. The resulting solid was then subjected to FT-IR analysis. The analysis revealed significant changes in peak intensity and pattern compared to before the test. Specifically, the polymeric MDI decomposed due to trace amounts of moisture in the air under heating conditions. The results are shown in Table 3.

[0145] Comparative Example 10 A stirring bar, 30 mg of polymeric MDI (manufactured by Tosoh Corporation; Millionate MR-200), and a 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 solid was subjected to FT-IR analysis. The analysis revealed that, compared to before the test, the isocyanate group peak disappeared, and instead, a carbonyl group peak derived from the reaction product of ethanol and polymeric MDI, and a peak derived from the hydrolysis of polymeric MDI were observed. In other words, polymeric MDI showed poor reaction selectivity between water and ethanol. The results are shown in Table 3.

[0146] Comparative Example 11 A stirring bar, 30 mg of 2,4,6-triterminate butylisocyanatobenzene, 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 did not disappear compared to before the test, and the shape of the other peaks remained unchanged. In other words, 2,4,6-triterminate butylisocyanatobenzene did not react with either water or ethanol. The results are shown in Table 3.

[0147] Table 3 shows that materials containing isocyanate compounds represented by general formula (1) are resistant to moisture in the environment and have the ability to capture alcohol compounds.

[0148] [Table 3]

[0149] Example 13 (Silica gel supported product 1 CARiACT Q-10) In a 500 mL round-bottom flask, a stirring bar, 1.0 g of the compound from Synthesis 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 and stirred at room temperature for 30 minutes. After removing the stirring bar, the solvent was slowly removed under reduced pressure using an evaporator. The resulting solid was dried at 60°C for 3 hours under a nitrogen gas flow, and then further dried at room temperature under a nitrogen gas flow for 24 hours. In this way, a silica gel-supported product of the compound from Synthesis Example 2 (the composition of the present invention, and the active hydrogen-containing organic compound scavenger of the present invention) was obtained.

[0150] Example 14 (Silica gel supported product 2 CARiACT G-10) In a 500 mL round-bottom flask, a stirring bar, 0.5 g of the compound from Synthesis 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 and the mixture was stirred at room temperature for 30 minutes. After removing the stirring bar, the solvent was slowly removed under reduced pressure using an evaporator. The resulting solid was dried at 60°C for 3 hours under a nitrogen gas flow, and then further dried at room temperature under a nitrogen gas flow for 24 hours. In this way, a silica gel-supported product of the compound from Synthesis Example 2 (the composition of the present invention, and the active hydrogen-containing organic compound scavenger of the present invention) was obtained.

[0151] Example 15 (Silica gel supported product 3 NIPGEL AY-001) In a 500 mL round-bottom flask, a stirring bar, 0.5 g of the compound from Synthesis Example 2, 9.5 g of silica gel NIPGEL AY-001 (manufactured by Tosoh Silica Co., Ltd.), and 200 mL of dichloromethane were added and the mixture was stirred at room temperature for 30 minutes. After removing the stirring bar, the solvent was slowly removed under reduced pressure using an evaporator. The resulting solid was dried at 60°C for 3 hours under a nitrogen gas flow, and then further dried at room temperature under a nitrogen gas flow for 24 hours. In this way, a silica gel-supported product of the compound from Synthesis Example 2 (the composition of the present invention, and the active hydrogen-containing organic compound scavenger of the present invention) was obtained.

[0152] Example 16 (Silica gel supported product 4 NIPGEL AY-220D) In a 500 mL round-bottom flask, a stirring bar, 0.5 g of the compound from Synthesis Example 2, 9.5 g of silica gel NIPGEL AY-220D (manufactured by Tosoh Silica Co., Ltd.), and 200 mL of dichloromethane were added and the mixture was stirred at room temperature for 30 minutes. After removing the stirring bar, the solvent was slowly removed under reduced pressure using an evaporator. The resulting solid was dried at 60°C for 3 hours under a nitrogen gas flow, and then further dried at room temperature under a nitrogen gas flow for 24 hours. In this way, a silica gel-supported product of the compound from Synthesis Example 2 (the composition of the present invention, and the active hydrogen-containing organic compound scavenger of the present invention) was obtained.

[0153] Example 17 (Silica gel supported product 4 NIPGEL CX-200) In a 500 mL round-bottom flask, a stirring bar, 0.5 g of the compound from Synthesis Example 2, 9.5 g of silica gel NIPGEL CX-200 (manufactured by Tosoh Silica Co., Ltd.), and 200 mL of dichloromethane were added and stirred at room temperature for 30 minutes. After removing the stirring bar, the solvent was slowly removed under reduced pressure using an evaporator. The resulting solid was dried at 60°C for 3 hours under a nitrogen gas flow, and then further dried at room temperature under a nitrogen gas flow for 24 hours. In this way, a silica gel-supported product of the compound from Synthesis Example 2 (the composition of the present invention, and the active hydrogen-containing organic compound scavenger of the present invention) was obtained.

[0154] Example 18 (Cellulose-supported product, Viscoparl A) In a 500 mL round-bottom flask, a stirring bar, 0.5 g of Compound 2 (Synthesis Example 2), 9.5 g of cellulose viscopar A (manufactured by Rengo Co., Ltd.), and 200 mL of dichloromethane were added and stirred at room temperature for 30 minutes. After removing the stirring bar, the solvent was slowly removed under reduced pressure using an evaporator. The resulting solid was dried at 60°C for 3 hours under a nitrogen gas flow, and then further dried at room temperature under a nitrogen gas flow for 24 hours. In this way, a cellulose-supported product of Compound 2 (the composition of the present invention, and the active hydrogen-containing organic compound scavenger of the present invention) was obtained.

[0155] Example 19 (Silica gel supported product 5 CARiACT Q-50) In a 500 mL round-bottom flask, a stirring bar, 0.5 g of the compound from Synthesis 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 and stirred at room temperature for 30 minutes. After removing the stirring bar, the solvent was slowly removed under reduced pressure using an evaporator. The resulting solid was dried at 60°C for 3 hours under a nitrogen gas flow, and then further dried at room temperature under a nitrogen gas flow for 24 hours. In this way, a silica gel-supported product of the compound from Synthesis Example 3 (the composition of the present invention, and the active hydrogen-containing organic compound scavenger of the present invention) was obtained.

[0156] Example 20 (Silica gel supported product 6 NIPGEL AY-001) In a 500 mL round-bottom flask, a stirring bar, 0.5 g of the compound from Synthesis Example 3, 9.5 g of silica gel NIPGEL AY-001 (manufactured by Tosoh Silica Co., Ltd.), and 200 mL of dichloromethane were added and stirred at room temperature for 30 minutes. After removing the stirring bar, the solvent was slowly removed under reduced pressure using an evaporator. The resulting solid was dried at 60°C for 3 hours under a nitrogen gas flow, and then further dried at room temperature under a nitrogen gas flow for 24 hours. In this way, a silica gel-supported product of the compound from Synthesis Example 3 (the composition of the present invention, and the active hydrogen-containing organic compound scavenger of the present invention) was obtained.

[0157] Example 31 (Silica gel supported product 7 NIPGEL CX-200) In a 500 mL round-bottom flask, a stirring bar, 0.5 g of compound 6 from synthesis example, 9.5 g of silica gel NIPGEL CX-200 (manufactured by Tosoh Silica Co., Ltd.), and 200 mL of dichloromethane were added and the mixture was stirred at room temperature for 30 minutes. After removing the stirring bar, the solvent was slowly removed under reduced pressure using an evaporator. The resulting solid was dried at 60°C for 3 hours under a nitrogen gas flow, and then further dried at room temperature under a nitrogen gas flow for 24 hours. In this way, a silica gel-supported product of compound 6 from synthesis example (the composition of the present invention, and the active hydrogen-containing organic compound scavenger of the present invention) was obtained.

[0158] Example 32 (Hydrotalcite-supported product Kyoward 500) In a 500 mL round-bottom flask, a stirring bar, 0.5 g of Compound 2 (Synthesis Example 2), 9.5 g of Kyoward 500 (hydrotalcite manufactured by Kyowa Chemical Industry Co., Ltd.), and 200 mL of dichloromethane were added and the mixture was stirred at room temperature for 30 minutes. After removing the stirring bar, the solvent was slowly removed under reduced pressure using an evaporator. The resulting solid was dried at 60°C for 3 hours under a nitrogen gas flow, and then further dried at room temperature under a nitrogen gas flow for 24 hours. In this way, a hydrotalcite-supported product of Compound 2 (the composition of the present invention, and the active hydrogen-containing organic compound scavenger of the present invention) was obtained.

[0159] [Gas capture evaluation] The active hydrogen-containing organic compound scavenger of the present invention was evaluated using an active hydrogen-containing organic compound gas capture amount evaluation apparatus schematically shown in Figure 1. The active hydrogen-containing organic compound gas adsorption apparatus comprises a reservoir tank (20L container made of stainless steel), a gas circulation pump, a column filled with the scavenger (0.1L container made of glass), a heater, etc. The reservoir tank was filled with gas of an active hydrogen-containing organic compound (ethanol, isopropanol, or acetic acid), and the inside of the apparatus was made into an atmosphere of active hydrogen-containing organic compound gas (the remainder being nitrogen gas) at a predetermined concentration (circulating gas). 5g of the scavenger of the present invention was packed into the column and the temperature was adjusted to 25°C. The circulating gas, also adjusted to 25°C using a heater, was passed through the column at a rate of 10L / min for 3 hours using a circulation pump, and the concentration of the active hydrogen-containing organic compound in the circulating gas in the reservoir tank after 3 hours was measured. Subsequently, the column filled with the scavenger was adjusted to 60°C using a heater. A circulating gas, also heated to 60°C in a heater, was passed through a column at a rate of 10 L / min for 30 minutes using a circulation pump. After 30 minutes, the concentration of active hydrogen-containing organic compounds in the gas in the reservoir tank was measured.

[0160] Example 21 (Ethanol gas capture evaluation) The active hydrogen-containing organic compound gas capture amount evaluation apparatus was subjected to a 500 ppm ethanol gas atmosphere (with the remainder being nitrogen gas). Next, the silica gel-supported product of Example 13 (the composition of the present invention and the active hydrogen-containing organic compound capture agent of the present invention) was packed into the column of the active hydrogen-containing organic compound gas capture amount evaluation apparatus and evaluated. After circulating at 25°C for 3 hours, the ethanol gas concentration in the apparatus was 145 ppm. After circulating at 60°C for 30 minutes, the ethanol gas concentration in the apparatus was 285 ppm. An amount of ethanol equivalent to the difference of 215 ppm (= 500 ppm - 285 ppm) was captured by the silica gel-supported product of Example 13 without being re-released. The results are shown in Table 4.

[0161] Example 22 (Ethanol gas capture evaluation) The active hydrogen-containing organic compound gas capture amount evaluation apparatus was subjected to a 500 ppm ethanol gas atmosphere (with the remainder being nitrogen gas). Next, the silica gel support of Example 14 (the composition of the present invention and the active hydrogen-containing organic compound capture agent of the present invention) was packed into the column of the active hydrogen-containing organic compound gas capture amount evaluation apparatus and evaluated. After circulating at 25°C for 3 hours, the ethanol gas concentration in the apparatus was 15 ppm. After circulating at 60°C for 30 minutes, the ethanol gas concentration in the apparatus was 160 ppm. An amount of ethanol equivalent to the difference of 340 ppm (= 500 ppm - 160 ppm) was captured by the silica gel support of Example 14 without being re-released. The results are shown in Table 4.

[0162] Example 23 (Ethanol gas capture evaluation) The active hydrogen-containing organic compound gas capture amount evaluation apparatus was subjected to a 500 ppm ethanol gas atmosphere (with the remainder being nitrogen gas). Next, the silica gel support of Example 15 (the composition of the present invention and the active hydrogen-containing organic compound capture agent of the present invention) was packed into the column of the active hydrogen-containing organic compound gas capture amount evaluation apparatus and evaluated. After circulating at 25°C for 3 hours, the ethanol gas concentration in the apparatus was less than 5 ppm. After circulating at 60°C for 30 minutes, the ethanol gas concentration in the apparatus was 55 ppm. An amount of ethanol equivalent to the difference of 445 ppm (= 500 ppm - 55 ppm) was captured by the silica gel support of Example 15 without being re-released. The results are shown in Table 4.

[0163] Example 24 (Ethanol gas capture evaluation) The active hydrogen-containing organic compound gas capture amount evaluation apparatus was subjected to a 500 ppm ethanol gas atmosphere (with the remainder being nitrogen gas). Next, the silica gel-supported product of Example 16 (the composition of the present invention and the active hydrogen-containing organic compound capture agent of the present invention) was packed into the column of the active hydrogen-containing organic compound gas capture amount evaluation apparatus and evaluated. After circulating at 25°C for 3 hours, the ethanol gas concentration in the apparatus was 10 ppm. After circulating at 60°C for 30 minutes, the ethanol gas concentration in the apparatus was 70 ppm. An amount of ethanol equivalent to the difference of 430 ppm (= 500 ppm - 70 ppm) was irreversibly captured by the silica gel-supported product of Example 16. The results are shown in Table 4.

[0164] Example 25 (Ethanol gas capture evaluation) The active hydrogen-containing organic compound gas capture amount evaluation apparatus was subjected to a 500 ppm ethanol gas atmosphere (with the remainder being nitrogen gas). Next, the silica gel support of Example 17 (the composition of the present invention and the active hydrogen-containing organic compound capture agent of the present invention) was packed into the column of the active hydrogen-containing organic compound gas capture amount evaluation apparatus and evaluated. After circulating at 25°C for 3 hours, the ethanol gas concentration in the apparatus was less than 5 ppm. After circulating at 60°C for 30 minutes, the ethanol gas concentration in the apparatus was 15 ppm. An amount of ethanol equivalent to the difference of 485 ppm (= 500 ppm - 15 ppm) was captured by the silica gel support of Example 17 without being re-released. The results are shown in Table 4.

[0165] Example 26 (Evaluation of ethanol gas capture) The active hydrogen-containing organic compound gas capture amount evaluation apparatus was subjected to a 500 ppm ethanol gas atmosphere (with the remainder being nitrogen gas). Next, the silica gel support of Example 20 (the composition of the present invention and the active hydrogen-containing organic compound capture agent of the present invention) was packed into the column of the active hydrogen-containing organic compound gas capture amount evaluation apparatus and evaluated. After circulating at 25°C for 3 hours, the ethanol gas concentration in the apparatus was 10 ppm. After circulating at 60°C for 30 minutes, the ethanol gas concentration in the apparatus was 50 ppm. An amount of ethanol equivalent to the difference of 450 ppm (= 500 ppm - 50 ppm) was captured by the silica gel support of Example 20 without being re-released. The results are shown in Table 4.

[0166] Example 33 (Ethanol gas capture evaluation) The active hydrogen-containing organic compound gas capture amount evaluation apparatus was subjected to a 500 ppm ethanol gas atmosphere (with the remainder being nitrogen gas). Next, the silica gel-supported product of Example 31 (the composition of the present invention and the active hydrogen-containing organic compound capture agent of the present invention) was packed into the column of the active hydrogen-containing organic compound gas capture amount evaluation apparatus and evaluated. After circulating at 25°C for 3 hours, the ethanol gas concentration in the apparatus was 5 ppm. After circulating at 60°C for 30 minutes, the ethanol gas concentration in the apparatus was 15 ppm. An amount of ethanol equivalent to the difference of 485 ppm (= 500 ppm - 15 ppm) was captured by the silica gel-supported product of Example 31 without being re-released. The results are shown in Table 4.

[0167] Example 34 (Isopropanol gas capture evaluation) In Example 33, the same procedure as in Example 33 was followed, except that the gas species (active hydrogen-containing organic compound to be captured) was changed from ethanol to isopropanol. After circulating at 25°C for 3 hours, the isopropanol gas concentration in the apparatus was 10 ppm. After circulating at 60°C for 30 minutes, the isopropanol gas concentration in the apparatus was 30 ppm. A net amount of isopropanol equivalent to 470 ppm (= 500 ppm - 30 ppm) was captured without being re-released onto the silica gel supported in Example 31. The results are shown in Table 4.

[0168] Example 35 (Evaluation of Acetic Acid Gas Capture) In Example 33, the procedure was the same as in Example 33, except that the gas species used (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. After circulating at 25°C for 3 hours, the acetic acid gas concentration in the apparatus was 0.2 ppm. After circulating at 60°C for 30 minutes, the acetic acid gas concentration in the apparatus was 0.4 ppm. An amount of acetic acid equivalent to the difference of 14.7 ppm (= 15.0 ppm - 0.4 ppm) was captured without being released back onto the silica gel supported in Example 31. The results are shown in Table 4.

[0169] Example 36 (Ethanol gas capture evaluation) The active hydrogen-containing organic compound gas capture amount evaluation apparatus was subjected to a 500 ppm ethanol gas atmosphere (with the remainder being nitrogen gas). Next, the hydrotalcite-supported product of Example 32 (the composition of the present invention and the active hydrogen-containing organic compound capture agent of the present invention) was packed into the column of the active hydrogen-containing organic compound gas capture amount evaluation apparatus and evaluated. After circulating at 25°C for 3 hours, the ethanol gas concentration in the apparatus was 55 ppm. After circulating at 60°C for 30 minutes, the ethanol gas concentration in the apparatus was 80 ppm. An amount of ethanol equivalent to the difference of 420 ppm (= 500 ppm - 80 ppm) was captured by the hydrotalcite-supported product of Example 32 without being re-released. The results are shown in Table 4.

[0170] Comparative Example 12 The active hydrogen-containing organic compound gas capture amount evaluation apparatus was subjected to a 500 ppm ethanol gas atmosphere (with the remainder being nitrogen gas). Next, the column of the active hydrogen-containing organic compound gas capture amount evaluation apparatus was left empty and evaluated. After 3 hours of circulation at 25°C, the ethanol gas concentration in the apparatus was 500 ppm. After 30 minutes of circulation at 60°C, the ethanol gas concentration in the apparatus was also 500 ppm. The ethanol concentration in the gas remained unchanged. The results are shown in Table 4.

[0171] Comparative Example 13 The active hydrogen-containing organic compound gas capture amount evaluation apparatus was subjected to a 15.0 ppm acetic acid gas atmosphere (with the remainder being nitrogen gas). Next, the column of the active hydrogen-containing organic compound gas capture amount evaluation apparatus was left empty and evaluated. After circulating at 25°C for 3 hours, the acetic acid gas concentration in the apparatus was 15.0 ppm. After circulating at 60°C for 30 minutes, the acetic acid gas concentration in the apparatus was also 15.0 ppm. The acetic acid concentration in the gas remained unchanged. The results are shown in Table 4.

[0172] [Table 4] [Explanation of Symbols]

[0173] 10. Reservoir tank (20L stainless steel container) 11. Thermohygrometer 12. Gas flow meter 13. Gas circulation pump 14. Warmer 15. Thermometer 16. Pressure gauge 17. Column packed with scavenging agent. 18. Warmer 19. Valve 20. Direction of circulating gas flow [Industrial applicability]

[0174] According to the present invention, organic compounds containing active hydrogen, such as alcohol compounds, which were difficult to capture with conventional techniques, can be efficiently captured. Furthermore, because it has irreversible capture capabilities and the capture effect persists even in humid environments, it can be used as an active hydrogen-containing organic compound scavenger in various fields such as environment and energy, and medical and life sciences.

Claims

1. The following general formula (1) has a bromine content of 38 to 78 wt% 【Chemistry 1】 (In the above general formula, R １ and R ２ Each of these is independently a hydrogen atom or an aluminum atom having 1 to 4 carbon atoms. Represents the kill group. R ３ Each of these independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a bromine atom. m represents at least one selected from the group consisting of 0, 1, 2, and 3. n represents a real number greater than or equal to 0. An active hydrogen-containing organic compound scavenger comprising an isocyanate compound represented by (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).

2. The isocyanate compound represented by the above general 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 given by the following general formula (1a) 【Chemistry 2】 (In the above general formula, R １ and R ２ Each of these independently represents either a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. ３ Each of these independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a bromine atom. m represents at least one selected from the group consisting of 0, 1, 2, and 3. n represents a real number greater than or equal to 0. The active hydrogen-containing organic compound scavenger according to claim 1, characterized in that it is an isocyanate compound represented by (which may be a single compound or a mixture of multiple compounds, in the case of a mixture, where n represents the average value of the mixture).

3. The isocyanate compound represented by the above general 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 given by the following general formula (1b) 【Transformation 3】 (In the above general formula, R １ and R ２ each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. R ３ each independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a bromine atom. n represents a real number of 0 or more.) The active hydrogen-containing organic compound scavenger according to claim 1, characterized in that it is an isocyanate compound represented by (which may be a single compound or a mixture of multiple compounds, in the case of a mixture, where n represents the average value of the mixture).

4. The active hydrogen-containing organic compound scavenger according to any one of claims 1 to 3, characterized in that the bromine content is 50 to 78 wt%.

5. The aforementioned R １ and R ２ The active hydrogen-containing organic compound scavenger according to any one of claims 1 to 4, characterized in that each is independently a hydrogen atom or a methyl group.

6. The aforementioned R １ and R ２ The active hydrogen-containing organic compound scavenger according to any one of claims 1 to 5, characterized in that the atom is a hydrogen atom.

7. In the above general formula (1), R ３ The active hydrogen-containing organic compound scavenger according to any one of claims 1 to 6, characterized in that each atom is independently a hydrogen atom or a bromine atom.

8. The active hydrogen-containing organic compound scavenger according to any one of claims 1 to 7, wherein n is a real number from 0 to 3.

9. A method for capturing a compound, characterized by contacting an active hydrogen-containing organic compound scavenger according to any one of claims 1 to 8 with at least one compound selected from the group consisting of alcohol compounds, thiol compounds, amine compounds, phenol compounds, and carboxylic acid compounds, and capturing the compound.

10. The following general formula (1) has a bromine content of 38 to 78 wt% 【Chemistry 4】 (In the above general formula, R １ and R ２ Each of these independently represents either a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. ３ Each of these independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a bromine atom. m represents at least one selected from the group consisting of 0, 1, 2, and 3. n independently represents a real number greater than or equal to 0. An active hydrogen-containing organic compound scavenger comprising an isocyanate compound represented by (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) and a carrier.

11. The isocyanate compound represented by the above general 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 given by the following general formula (1a) 【Transformation 5】 (In the above general formula, R １ and R ２ Each of these independently represents either a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. ３ Each of these independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a bromine atom. m represents at least one selected from the group consisting of 0, 1, 2, and 3. n independently represents a real number greater than or equal to 0. The active hydrogen-containing organic compound scavenger according to claim 10, characterized in that it is an isocyanate compound represented by (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).

12. The isocyanate compound represented by the above general 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 given by the following general formula (1b) 【Transformation 6】 (In the above general formula, R １ and R ２ Each of these independently represents either a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. ３ Each of these independently represents a hydrogen atom, an alkyl group with 1 to 4 carbon atoms, or a bromine atom. Each of these independently represents a real number greater than or equal to 0. The active hydrogen-containing organic compound scavenger according to claim 10, characterized in that it is an isocyanate compound represented by (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).

13. The aforementioned R ３ The active hydrogen-containing organic compound scavenger according to any one of claims 10 to 12, characterized in that each atom is independently a hydrogen atom or a bromine atom.

14. An active hydrogen-containing organic compound scavenger according to any one of claims 10 to 13, characterized in that the isocyanate compound is supported on the carrier.

15. The active hydrogen-containing organic compound scavenger according to any one of claims 10 to 14, wherein the amount of the isocyanate compound supported is 0.1 to 60 parts by weight per 100 parts by weight of the carrier.

16. The activated hydrogen-containing organic compound scavenger according to any one of claims 10 to 15, wherein the carrier is one or more carriers selected from the group consisting of activated carbon, activated clay, diatomaceous earth, porous resin, nonwoven fabric, mesoporous silica, silica gel, aluminosilicate, hydrotalcite, zeolite, activated alumina, titania, magnesia, and zirconia.

17. A method for capturing a compound, characterized by contacting an active hydrogen-containing organic compound scavenger according to any one of claims 10 to 16 with at least one compound selected from the group consisting of alcohol compounds, thiol compounds, amine compounds, phenol compounds, and carboxylic acid compounds, and capturing the compound.

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