Scavenger for carbonyl compounds

Abstract

To provide a scavenger that can efficiently capture carbonyl compounds and has water resistance and heat resistance.SOLUTION: A scavenger for carbonyl compounds is used, which includes a support carrying, via chemical bonding, an aminooxyalkyl group-containing polysiloxane having a structural unit represented by the general formula (1) in the figure, where R represents an alkyl group or the like, Q represents -CH2- or the like, and M represents an aluminum atom, a silicon atom, or a titanium atom.SELECTED DRAWING: None

Description

Technical Field

[0001] The present disclosure relates to a scavenger for carbonyl compounds.

Background Art

[0002] In living spaces for people such as inside houses and cars, there are various gaseous pollutant compounds that cause bad odors. There has been an increasing interest in removing these gaseous pollutant compounds to obtain a comfortable environment. For example, carbonyl compounds such as aldehydes and ketones are included in various odors such as tobacco smoke, body odor, pet odor, mold odor, paint odor, and printing odor. Carbonyl compounds not only give people discomfort due to the odor, but also are suspected of being carcinogenic depending on the type of compound, and there are concerns about their effects on the human body. Therefore, a method for efficiently removing carbonyl compounds is required, and scavengers composed of hydrazine derivatives, amines, amino acids, urea derivatives, silica gel, etc. have been proposed (see, for example, Patent Documents 1 to 3).

[0003] The methods described in Patent Documents 1 to 3 above have problems such as the capture efficiency not being necessarily sufficient and the water resistance not being sufficient, so that the scavenger elutes by washing with water and the performance deteriorates. Also, since the heat resistance is not sufficient, there are problems such as the performance deteriorating due to operations including heating such as drying and kneading into resin.

[0004] In addition, a scavenger in which the surface of silica gel is modified with a monomer of a silane coupling agent has been proposed (see, for example, Patent Document 4). However, the monomer of the silane coupling agent has problems such that the alkoxysilyl moiety is unstable to water and easily decomposes, or the alkoxysilyl moiety is stable and the immobilization reaction on silica gel does not proceed efficiently, or the monomer of the silane coupling agent is insoluble in water and cannot be uniformly added to silica gel.

Prior Art Documents

Patent Documents

[0005]

Patent Document 1

Patent Document 2

Patent Document 3

Patent Document 4

Summary of the Invention

Problems to be Solved by the Invention

[0006] The present invention has been made in view of the background of the related art, and an object of the present invention is to provide a scavenger that exhibits a scavenging effect of a carbonyl compound superior to that of the related art even when washed with water or heated.

Means for Solving the Problems

[0007] As a result of intensive studies to solve the above problems, the present inventors have found that a carrier carrying a specific polysiloxane or a composition containing the same can solve the above problems, and have completed the present invention.

[0008] That is, the present disclosure includes the following embodiments.

[0009] [1] The following general formula (1)

[0010]

Chemical Formula

[0011] [In formula (1), each R independently represents an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a hydroxyl group, and the alkyl group may be substituted with a primary amino group or a ureido group at an arbitrary position.

[0012] Q each independently represents -CH 2 -, -CH 2 CH 2 -, and -CH2 -Ra-CH 2 represents one or more groups selected from the group consisting of, Ra represents an alkylene group having 1 to 18 carbon atoms, and two or more non-adjacent -CH in the alkylene group 2 - may each independently be replaced by -O-, -(C=O)O-, -O(C=O)-, -O(C=O)-O-, -C(=O)-NH-, -NH-(C=O)-, -CH=CH-, or -C≡C-, and the hydrogen atom of the alkylene group may be replaced by an alkyl group having 1 to 3 carbon atoms.

[0013] M represents an aluminum atom, a silicon atom, or a titanium atom.

[0014] m represents an integer of 1 or 2.

[0015] When M is an aluminum atom, m is 1, and when M is a silicon atom or a titanium atom, m is 2. When m is 1, one R is bonded to M. When m is 2, two Rs are bonded to M.

[0016] n represents a real number from 0 to 1000. A scavenger for carbonyl compounds comprising a carrier on which an aminooxyalkyl group-containing polysiloxane having a structural unit represented by the formula is supported by a chemical bond.

[0017] [2] In the general formula (1) above, the scavenger for carbonyl compounds according to [1] above, wherein each R is independently a methyl group, a 3-aminopropyl group, a 3-ureidopropyl group, a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, or a hydroxyl group.

[0018] [3] In the general formula (1) above, the scavenger for carbonyl compounds according to [1] or [2] above, wherein n is 0.

[0019] [4] The aminooxyalkyl group-containing polysiloxane represented by the general formula (1) above is the following general formula (1a)

[0020] [Chemical formula]

[0021] [In formula (1a), R, Q, and n have the same meanings as R, Q, and n in the general formula (1).] The scavenger for a carbonyl compound according to any one of [1] to [3] above, which is an aminooxyalkyl group-containing polysiloxane represented by the following formula:

[0022] [5] The scavenger for a carbonyl compound according to any one of [1] to [4] above, wherein the carrier is at least one selected from the group consisting of silica gel, alumina, zeolite, magnesia, titania, zirconia, zinc oxide, zinc hydroxide, zinc silicate, ceria, diatomaceous earth, activated carbon, and hydroxyapatite.

[0023] [6] The scavenger for a carbonyl compound according to any one of [1] to [4] above, wherein the carrier is silica gel.

[0024] [7] A method for removing a carbonyl compound, which comprises bringing the scavenger according to any one of [1] to [6] into contact with a carbonyl compound.

[0025] [8] The method for removing a carbonyl compound according to [7] above, wherein the carbonyl compound is at least one selected from the group consisting of aldehydes and ketones. [Advantages of the Invention]

[0026] The scavenger for a carbonyl compound according to one aspect of the present disclosure can rapidly and continuously capture a carbonyl compound. As a result, it is effective in reducing carbonyl compounds harmful to the human body and has the effect of improving the living environment. [Embodiments for Carrying Out the Invention]

[0027] Hereinafter, the present invention will be described in detail. In this specification, "~" means a numerical range including the numerical values at both ends thereof.

[0028] The carbonyl compound scavenger according to one aspect of the present disclosure includes a carrier (hereinafter simply referred to as "supported carrier") on which an aminooxyalkyl group-containing polysiloxane having a structural unit represented by the above general formula (1) is supported by a chemical bond.

[0029] The above-mentioned supported carrier is preferably a reaction product obtained by reacting an aminooxyalkyl group-containing polysiloxane having a structural unit represented by the above general formula (1) with a carrier having hydroxyl groups on its surface (hereinafter, the above reaction is also referred to as a "silane coupling reaction"). That is, the above-mentioned supported carrier can be produced by reacting the above-mentioned aminooxyalkyl group-containing polysiloxane with a carrier having hydroxyl groups on its surface.

[0030] In the above general formula (1), each R independently represents an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a hydroxyl group.

[0031] The alkyl group having 1 to 4 carbon atoms is not particularly limited, and examples thereof include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a 2-methylpropyl group, a 1-methylpropyl group, and a tert-butyl group.

[0032] The alkoxy group having 1 to 4 carbon atoms is not particularly limited, and examples thereof include a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, a 2-methylpropyloxy group, a 1-methylpropyloxy group, and a tert-butoxy group.

[0033] Among these, as R, a methyl group, a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, or a hydroxyl group is preferable in terms of excellent capture of carbonyl compounds.

[0034] In the above general formula (1), each Q independently represents -CH 2 -, -CH 2 CH 2 -, and -CH2 -Ra-CH 2 represents one or more groups selected from the group consisting of. Ra represents an alkylene group having 1 to 18 carbon atoms, and two or more non-adjacent -CH in the alkylene group 2 - may each independently be replaced by -O-, -(C=O)O-, -O(C=O)-, -O(C=O)-O-, -C(=O)-NH-, -NH-(C=O)-, -CH=CH-, or -C≡C-, and the hydrogen atom of the alkylene group may be replaced by an alkyl group having 1 to 3 carbon atoms.

[0035] In the above general formula (1), M represents an aluminum atom, a silicon atom, or a titanium atom.

[0036] In the above general formula (1), m represents an integer of 1 or 2.

[0037] When M is an aluminum atom, m is 1, and when M is a silicon atom or a titanium atom, m is 2. When m is 1, one R is bonded to M. When m is 2, two Rs are bonded to M.

[0038] In the above general formula (1), n represents a real number from 0 to 1000.

[0039] As the aminooxyalkyl group-containing polysiloxane having the structural unit represented by the above general formula (1), an aminooxyalkyl group-containing polysiloxane in which M is a silicon atom and m is 2, that is, represented by the above general formula (1a), is preferable.

[0040] In the present disclosure, the aminooxyalkyl group-containing polysiloxane is, as described above, a polymer of a monomer having an aminooxyalkyl group, or a copolymer containing a monomer having an aminooxyalkyl group and a monomer not having an aminooxyalkyl group. The above general formula (1) means that the ratio of the monomer having an aminooxyalkyl group to the monomer not having an aminooxyalkyl group is 1 to 0 to 1000 in terms of molar ratio.

[0041] The monomer having the aminooxyalkyl group may be purchased as a commercial product and used. However, for example, it can also be synthesized according to the methods described in Organic Preparations and Procedures International, vol.26, 1994, 111-113, JP-A-7-233132, Tetrahedron Letters, Vol.46(14), 2005, 7973-7975, etc.

[0042] The molecular shape of the aminooxyalkyl group-containing polysiloxane having the structural unit represented by the above general formula (1) is not particularly limited, and for example, it can take any molecular shape such as linear, branched, cyclic, cage-like, etc.

[0043] In the present disclosure, the loading amount of the aminooxyalkyl group-containing polysiloxane on the supporting carrier can be arbitrarily adjusted according to the purpose and is not particularly limited. However, based on the unit weight of the carrier on which the aminooxyalkyl group-containing polysiloxane is supported by chemical bonding, a range of 0.1 to 50% by weight is preferable.

[0044] The above-mentioned carrier is not particularly limited, and examples thereof include a polymer carrier or an inorganic carrier.

[0045] Examples of the above-mentioned polymer carrier include, but are not particularly limited to, styrene-based polymers (for example, polystyrene, crosslinked polystyrene, etc.), polyolefins (for example, polyethylene, polypropylene, etc.), poly(halogenated olefins) (for example, polyvinyl chloride, polytetrafluoroethylene, etc.), nitrile-based polymers (for example, polyacrylonitrile, etc.), (meth)acrylic-based polymers (for example, polymethyl methacrylate, polyethyl acrylate, etc.), high molecular weight polysaccharides (for example, cellulose, agarose, dextran, etc.).

[0046] The inorganic carrier mentioned above is not particularly limited. For example, silica gel, alumina, zeolite, magnesia, titania, zirconia, zinc oxide, zinc hydroxide, zinc silicate, ceria, diatomaceous earth, activated carbon, hydroxyapatite, etc. can be mentioned.

[0047] Among these, as the carrier mentioned above, in terms of the efficiency of the above silane coupling reaction, it is preferably an inorganic carrier, more preferably silica gel, alumina, zeolite, magnesia, titania, zirconia, zinc oxide, zinc hydroxide, zinc silicate, ceria, diatomaceous earth, activated carbon, or hydroxyapatite, and even more preferably silica gel.

[0048] In addition, as the carrier mentioned above, it is preferably a carrier having hydroxyl groups on its surface.

[0049] The shape of the carrier mentioned above is not particularly limited. For example, spherical, granular, fibrous, particulate, monolithic column, hollow fiber, membranous, etc. can be mentioned. Regarding the above shape, in terms of excellent carbonyl compound capturing effect, it is preferably spherical, membranous, granular, particulate, or fibrous, and more preferably spherical, granular, or particulate.

[0050] The particle size of the spherical, granular, or particulate carrier is preferably in the range of an average particle diameter of 0.1 μm to 10 mm, and more preferably an average particle diameter of 1 μm to 100 μm in terms of good dispersibility in the liquid.

[0051] The carrier mentioned above may be porous or non-porous, but in terms of excellent carbonyl compound capturing effect, it is preferably porous.

[0052] When the carrier mentioned above is a porous carrier, the average pore diameter of the porous carrier is preferably 1 nm to 1 μm, and more preferably 1 nm to 300 nm in terms of excellent carbonyl compound capturing effect.

[0053] The above-mentioned scavenger for carbonyl compounds exhibits a particularly excellent scavenging effect on aldehydes and ketones among carbonyl compounds.

[0054] The aldehydes that can be scavenged by the above-mentioned scavenger for carbonyl compounds are not particularly limited. For example, formaldehyde, acetaldehyde, propionaldehyde, normal butyraldehyde, isobutyraldehyde, normal valeraldehyde, isovaleraldehyde, etc. can be mentioned.

[0055] The ketones that can be scavenged by the above-mentioned scavenger for carbonyl compounds are not particularly limited. For example, dimethyl ketone (acetone), methyl ethyl ketone, diethyl ketone, methyl propyl ketone, methyl isobutyl ketone, methyl amyl ketone, cyclopropanone, cyclobutanone, cyclopentanone, cyclohexanone, isophorone, acetophenone, benzophenone, etc. can be mentioned.

[0056] The method of using the above-mentioned scavenger for carbonyl compounds is not particularly limited. For example, by bringing the above-mentioned scavenger for carbonyl compounds into contact with a gas or liquid containing the carbonyl compound and reacting the carbonyl compound in the gas or liquid with the above-mentioned scavenger for carbonyl compounds, the concentration of the carbonyl compound in the gas or liquid can be reduced. The gas is not particularly limited. For example, air, nitrogen, etc. can be mentioned. The liquid is not particularly limited. For example, water, alcohol, etc. can be mentioned.

[0057] Another method of using the above-mentioned scavenger for carbonyl compounds is not particularly limited. For example, a method of using the scavenger in a state where it is attached to a substrate, and a method of using the scavenger in a state where it is kneaded into a resin can be mentioned. The substrate to which the scavenger is attached and the resin in which the scavenger is kneaded are hereinafter referred to as "scavenging structures".

[0058] The above-mentioned capture structure can be manufactured by applying or spraying the above-mentioned capture agent onto a substrate. The capture agent can also be mixed with a binder resin and then applied or sprayed onto a substrate to form a capture structure. The binder resin is not particularly limited, and examples thereof include acrylic ester resin, silicone resin, urethane resin, polyester resin, melamine resin, polypropylene resin, and fluororesin.

[0059] When the above-mentioned capture structure is exposed to a gas containing an odor-causing substance that causes a bad odor, the odor-causing substance in the gas can be captured, and the bad odor of the gas can be reduced.

[0060] The substrate is not particularly limited, and examples thereof include fiber, sheet, wallpaper, sponge, beads, wood, plywood, and gypsum board.

[0061] The materials of the above-mentioned fiber, sheet, wallpaper, or sponge are not particularly limited, and examples thereof include polyester, polyamide, polyacrylonitrile, polypropylene, polyethylene, polyvinyl chloride, fluororesin, aramid resin, sulfone resin, rayon, acetate, cotton, wool, silk, hemp, glass, carbon, ceramics, silicone resin, polyimide resin, natural rubber, and polyurethane.

[0062] The capture structure is not particularly limited, and examples thereof include clothing, curtains, carpets, wall coverings, automotive interior materials, and furniture.

[0063] The amount of the capture agent immobilized on the substrate can be arbitrarily adjusted according to the purpose and is not particularly limited. However, based on the unit area of the substrate, the capture agent is preferably in the range of 0.1 to 200 g / m 2 and more preferably in the range of 0.5 to 75 g / m 2 of the range.

[0064] The above-mentioned capture structure can also be manufactured by dispersing and mixing a resin and the above-mentioned capture agent.

[0065] The resin is not particularly limited, and examples thereof include low-density polyethylene by high-pressure method, high-density polyethylene, ethylene-1-butene copolymer, ethylene-1-hexene copolymer, ethylene-1-octene copolymer, ethylene-4-methyl-1-pentene copolymer, ethylene-vinyl acetate copolymer, ethylene-methyl acrylate copolymer, ethylene-methyl methacrylate copolymer, polypropylene, propylene-ethylene copolymer, propylene-1-butene copolymer, poly-1-butene, poly-1-hexene, poly-4-methyl-1-pentene, and the like.

[0066] The above-mentioned dispersion mixing can be carried out by a commonly used resin kneading apparatus. The kneading apparatus is not particularly limited, and examples thereof include a single-screw extruder, a twin-screw extruder, a multi-screw extruder, a Banbury mixer, a pressure kneader, a rotating roll, an internal mixer, and the like.

[0067] The mixing amount of the capture agent of the carbonyl compound in the resin can be arbitrarily adjusted according to the purpose and is not particularly limited. However, based on the unit weight of the resin, a range of 0.01 to 50% by weight is preferable, and a range of 0.01 to 10% by weight is more preferable.

Example

[0068] Hereinafter, one aspect of the present disclosure will be described in more detail with reference to examples, but the present invention should not be construed as being limited by these examples. Unless otherwise specified, commercially available products were used for the reagents and the like used.

[0069] The analytical instruments and evaluation methods used in this example are listed below.

[0070] <Aldehyde capture test> After enclosing 20 mg of the carbonyl compound scavenger in a 5 L Tedlar bag, 3 L of nitrogen gas with an acetaldehyde concentration of approximately 350 ppm was added. After standing at room temperature for 24 hours, 0.1 L of the gas in the Tedlar bag was adsorbed onto a cartridge (manufactured by Fuji Film Wako Pure Chemical Corporation, Presep-C DNPH) loaded with 2,4-dinitrophenylhydrazine (DNPH). This cartridge was treated with acetonitrile to elute the DNPH-aldehyde condensate. Subsequently, the eluate was quantified for the DNPH-aldehyde condensate using a liquid chromatograph (manufactured by Shimadzu Corporation, LC-2030C Plus), and the residual acetaldehyde concentration inside the Tedlar bag was calculated. From the difference between the added acetaldehyde and the residual acetaldehyde, the aldehyde capture capacity [mg / g] was calculated.

[0071] <Water resistance test> 0.5 g of the carbonyl compound scavenger and 50 g of water were mixed and loosened with an ultrasonic cleaner (manufactured by AS ONE Corporation, ASU-M) for 5 minutes to form a suspension. The obtained suspension was filtered, and the residue was dried at 120 °C for 1 hour to obtain the carbonyl compound scavenger after washing with water. Aldehyde capture tests were performed on the carbonyl compound scavenger before washing with water and the carbonyl compound scavenger after washing with water, respectively, to calculate the aldehyde capture capacity. Furthermore, the water resistance rate was calculated using the following formula.

[0072] Water resistance rate [%] = [(aldehyde capture capacity of the carbonyl compound scavenger after washing with water) / (aldehyde capture capacity of the carbonyl compound scavenger before washing with water)] × 100.

[0073] <Heat resistance test> 1 g of the carbonyl compound scavenger was left standing in an oven heated to 200 °C for 30 minutes to obtain the carbonyl compound scavenger after heating. Aldehyde capture tests were performed on the carbonyl compound scavenger before heating and the aldehyde scavenger after heating, respectively, to calculate the aldehyde capture capacity. Furthermore, the heat resistance rate was calculated using the following formula.

[0074] Heat resistance rate [%] = [(Aldehyde capture capacity of the carbonyl compound scavenger after heating) / (Aldehyde capture capacity of the carbonyl compound scavenger before heating)] × 100.

[0075] In addition, the following abbreviations were used for the compounds used in the examples.

[0076] O-[3-(Triethoxysilyl)propyl]hydroxylamine = Si-1 Tetraethoxysilane = TEOS 3-(Triethoxysilyl)propylamine = APTES 3-(Trimethoxysilyl)propylurea = UPTMS

[0077] [Chemical formula]

[0078] Synthesis Example 1 Si-1 (0.78 g, 3.29 mmol) and water (9.22 g) were mixed and stirred under reflux conditions (oil bath temperature 110 °C) for 20 hours to obtain a transparent solution containing an aminooxyalkyl group-containing polysiloxane. As a result of measuring the molecular weight of the obtained aminooxyalkyl group-containing polysiloxane by gel permeation chromatography (manufactured by Shimadzu Corporation, Prominence), the number average molecular weight (Mn) = 930, the weight average molecular weight (Mw) = 1100, and the dispersity (Mw / Mn) = 1.18.

[0079] Synthesis Example 2 Si-1 (0.78 g, 3.29 mmol), TEOS (0.21 g, 1.00 mmol) and water (9.01 g) were mixed and stirred under reflux conditions (oil bath temperature 110 °C) for 20 hours to obtain a transparent solution containing an aminooxyalkyl group-containing polysiloxane. As a result of measuring the molecular weight of the obtained aminooxyalkyl group-containing polysiloxane by gel permeation chromatography (manufactured by Shimadzu Corporation, Prominence), the number average molecular weight (Mn) = 1000, the weight average molecular weight (Mw) = 1200, and the dispersity (Mw / Mn) = 1.20.

[0080] Synthesis Example 3 Si-1 (0.78 g, 3.29 mmol), APTES (0.22 g, 0.99 mmol), and water (9.00 g) were mixed and stirred under reflux conditions (oil bath temperature 110 °C) for 20 hours to obtain a transparent solution containing an aminooxyalkyl group-containing polysiloxane. As a result of measuring the molecular weight of the obtained aminooxyalkyl group-containing polysiloxane by gel permeation chromatography (manufactured by Shimadzu Corporation, Prominence), the number average molecular weight (Mn) = 890, the weight average molecular weight (Mw) = 910, and the dispersity (Mw / Mn) = 1.02.

[0081] Synthesis Example 4 Si-1 (0.78 g, 3.29 mmol), UPTMS (0.73 g, 3.28 mmol), and water (8.49 g) were mixed and stirred under reflux conditions (oil bath temperature 110 °C) for 20 hours to obtain a transparent solution containing an aminooxyalkyl group-containing polysiloxane. As a result of measuring the molecular weight of the obtained aminooxyalkyl group-containing polysiloxane by gel permeation chromatography (manufactured by Shimadzu Corporation, Prominence), the number average molecular weight (Mn) = 870, the weight average molecular weight (Mw) = 1200, and the dispersity (Mw / Mn) = 1.38.

[0082] Example 1 6.0 g of the solution containing the polysiloxane obtained in Synthesis Example 1 was added to 3.4 g of silica gel (manufactured by Tosoh Silica Corporation, NIPGEL CX400), mixed with a spatula until homogeneous, and dried under reduced pressure in an oven at 120 °C for 2 hours to obtain a scavenger for carbonyl compounds. When an aldehyde scavenging test was conducted on the obtained scavenger for carbonyl compounds, the aldehyde scavenging capacity was 26 mg / g. Furthermore, a water resistance test was conducted. The results are shown in Table 1.

[0083] Example 2 6.0 g of the solution containing the polysiloxane obtained in Synthesis Example 2 was added to 3.4 g of silica gel (manufactured by Tosoh Silica Corporation, NIPGEL CX400), and the mixture was stirred with a spatula until homogeneous, and then dried under reduced pressure in an oven at 120 °C for 2 hours to obtain a scavenger for carbonyl compounds. An aldehyde scavenging test was conducted on the obtained scavenger for carbonyl compounds, and the aldehyde scavenging capacity was 26 mg / g. Further, a water resistance test was conducted. The results are shown in Table 1.

[0084] Example 3 6.0 g of the solution containing the polysiloxane obtained in Synthesis Example 3 was added to 3.4 g of silica gel (manufactured by Tosoh Silica Corporation, NIPGEL CX400), and the mixture was stirred with a spatula until homogeneous, and then dried under reduced pressure in an oven at 120 °C for 2 hours to obtain a scavenger for carbonyl compounds. An aldehyde scavenging test was conducted on the obtained scavenger for carbonyl compounds, and the aldehyde scavenging capacity was 34 mg / g. Further, a water resistance test was conducted. The results are shown in Table 1.

[0085] Example 4 6.0 g of the solution containing the polysiloxane obtained in Synthesis Example 4 was added to 3.4 g of silica gel (manufactured by Tosoh Silica Corporation, NIPGEL CX400), and the mixture was stirred with a spatula until homogeneous, and then dried under reduced pressure in an oven at 120 °C for 2 hours to obtain a scavenger for carbonyl compounds. An aldehyde scavenging test was conducted on the obtained scavenger for carbonyl compounds, and the aldehyde scavenging capacity was 18 mg / g. Further, a water resistance test was conducted. The results are shown in Table 1.

[0086] Comparative Example 1 1.0 g of a 5 wt% aqueous solution of aminooxyacetic acid was added to 1.0 g of silica gel (manufactured by Tosoh Silica Corporation, NIPGEL CX-400), and the mixture was stirred with a spatula until homogeneous, and then dried under reduced pressure in an oven at 55 °C for 12 hours to obtain a scavenger for carbonyl compounds. An aldehyde scavenging test was conducted on the obtained scavenger for carbonyl compounds, and the aldehyde scavenging capacity was 15 mg / g. Further, a water resistance test was conducted. The results are shown in Table 1.

[0087] As is clear from Table 1, the carbonyl compound scavenger of the present invention showed high water resistance as compared with existing scavengers.

[0088]

Table 1

[0089] Example 5 A heat resistance test was conducted on the carbonyl compound scavenger obtained in Example 1. The results are shown in Table 2.

[0090] Example 6 A heat resistance test was conducted on the carbonyl compound scavenger obtained in Example 2. The results are shown in Table 2.

[0091] Example 7 A heat resistance test was conducted on the carbonyl compound scavenger obtained in Example 3. The results are shown in Table 2.

[0092] Example 8 A heat resistance test was conducted on the carbonyl compound scavenger obtained in Example 4. The results are shown in Table 2.

[0093] Comparative Example 2 A heat resistance test was conducted on the carbonyl compound scavenger obtained in Comparative Example 1. The results are shown in Table 2.

[0094] As is clear from Table 2, the carbonyl compound scavenger of the present invention showed high heat resistance as compared with existing scavengers.

[0095]

Table 2

[0096] Example 9 When the following acetone capture test was conducted on the carbonyl compound scavenger obtained in Example 1, the ketone capture rate was 95%.

[0097] Comparative Example 3 An acetone capture test was conducted using silica gel (manufactured by Tosoh Silica Corporation, NIPGEL CX-400) as a scavenger for carbonyl compounds, and the ketone capture rate was 13%.

[0098] <Acetone capture test> 1.0 g of a scavenger for carbonyl compounds and 20 g of a 0.5 wt% aqueous acetone solution were mixed, and aggregation was loosened for 5 minutes using an ultrasonic cleaner (manufactured by AS ONE Corporation, ASU-M) to obtain a suspension. Then, the suspension was passed through a syringe filter with a pore size of 0.45 μm (manufactured by Advantec, DISMIC13HP) to remove the aminooxy group-supported carrier, and an aqueous solution was obtained. 1 μL of the obtained aqueous solution was analyzed using a gas chromatograph (manufactured by Shimadzu Corporation, GC-2030), and the area value of acetone was recorded. An autosampler (manufactured by Shimadzu Corporation, AOC-30i) was used for sample injection into the gas chromatograph. Using the recorded area value of acetone and the calibration curve, the acetone concentration after the capture test was calculated. Furthermore, the acetone capture rate [%] was calculated from the following formula.

[0099] Acetone capture rate [%] = [(initial acetone concentration - acetone concentration after capture test) ÷ initial acetone concentration] × 100.

[0100] Example 10 Hereinafter, 4-nitrobenzaldehyde is abbreviated as NBA. For the scavenger for carbonyl compounds obtained in Example 1, the following NBA capture test was conducted, and the NBA capture capacity was 83 mg / g.

[0101] <NBA capture test> 60 mg of NBA (manufactured by Tokyo Chemical Industry Co., Ltd.) and 10 g of p-xylene (manufactured by Fujifilm Wako Pure Chemical Corporation) were mixed in a glass container to form a solution. Subsequently, 0.1 g of a carbonyl compound scavenger and 10 g of water were added to the glass container, and the mixture was stirred at 80 °C for 1 hour. After stopping the stirring, the mixture was allowed to stand for 15 minutes, and the supernatant organic layer was passed through a syringe filter with a pore size of 0.45 μm (DISMIC13HP, manufactured by Advantec) to obtain an NBA solution after filtration. The NBA solution after filtration was analyzed using a liquid chromatograph (LC2050, manufactured by Shimadzu Corporation), and the remaining amount of NBA [mg] was calculated. The NBA capture capacity [mg / g] was calculated using the following formula.

[0102] NBA capture capacity [mg / g] = (amount of NBA charged [mg] - remaining amount of NBA [mg]) ÷ amount of carbonyl compound scavenger charged [g].

Claims

1. The following general formula (1) 【Chemistry 1】 In formula (1), each R independently represents an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a hydroxyl group, and the alkyl group may be substituted at any position with a primary amino group or a ureido group. Each Q is independently -CH ２ --, --CH ２ CH ２ - and -CH ２ -Ra-CH ２ -, Ra represents an alkylene group having 1 to 18 carbon atoms, and in the alkylene group, two or more -CH ２ Each - may be independently replaced by -O-, -(C=O)O-, -O(C=O)-, -O(C=O)-O-, -C(=O)-NH-, -NH-(C=O)-, -CH=CH-, or -C≡C-, and a hydrogen atom of the alkylene group may be substituted by an alkyl group having 1 to 3 carbon atoms. M represents an aluminum atom, a silicon atom, or a titanium atom. m represents an integer of 1 or 2. When M is an aluminum atom, m is 1, and when M is a silicon atom or a titanium atom, m is 2. When m is 1, one R is bonded to M. When m is 2, two R are bonded to M. n represents a real number from 0 to 1000. The carbonyl compound scavenger comprises a carrier having an aminooxyalkyl group-containing polysiloxane having a structural unit represented by the following formula supported thereon by chemical bonding.

2. 2. The scavenger according to claim 1, wherein in the general formula (1), each R is independently a methyl group, a 3-aminopropyl group, a 3-ureidopropyl group, a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, or a hydroxyl group.

3. The scavenger according to claim 1 , wherein n is 0 in the general formula (1).

4. The aminooxyalkyl group-containing polysiloxane represented by the above general formula (1) is represented by the following general formula (1a): 【Chemistry 2】 [In formula (1a), R, Q, and n have the same meanings as R, Q, and n in general formula (1).] 2. The scavenger according to claim 1, which is an aminooxyalkyl group-containing polysiloxane represented by the formula:

5. 2. The scavenger according to claim 1, wherein the carrier is at least one selected from the group consisting of silica gel, alumina, zeolite, magnesia, titania, zirconia, zinc oxide, zinc hydroxide, zinc silicate, ceria, diatomaceous earth, activated carbon, and hydroxyapatite.

6. 2. The capture agent according to claim 1, wherein the carrier is silica gel.

7. A method for removing carbonyl compounds, comprising contacting the scavenger according to any one of claims 1 to 6 with the carbonyl compounds.

8. 8. The method for removing carbonyl compounds according to claim 7, wherein the carbonyl compound is at least one selected from the group consisting of aldehydes and ketones.

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