Polysiloxane, production method for same, and deodorizing agent containing same

Abstract

The present invention provides a deodorizing agent that has excellent capture efficiency and water resistance.　An aminooxyalkyl group-containing polysiloxane having a structural unit represented by general formula (1) is used.

Description

Polysiloxane, its manufacturing method, and deodorant containing same

[0001] The present invention relates to a polysiloxane, a method for producing the same, and a deodorant containing the same.

[0002] Aldehydes, such as acetaldehyde and formaldehyde, are typical odorants in living environments. Because their odor threshold is extremely low, even low concentrations can cause unpleasant odors. These aldehydes are generated indoors and in automobiles from synthetic resins, plywood, cigarette smoke, and other sources, and are known to cause sick building syndrome and sick car syndrome. Furthermore, these aldehydes are suspected of being carcinogenic, and daily exposure to them poses a health risk. Therefore, the Ministry of Health, Labor, and Welfare has set indoor concentration guidelines of 0.03 ppm for acetaldehyde and 0.08 ppm for formaldehyde. Therefore, there is a need for a means to rapidly and sustainably remove aldehydes.

[0003] Lower aldehydes such as acetaldehyde and formaldehyde have low boiling points, and therefore, inorganic porous materials commonly used as deodorizers, such as silica gel and activated carbon, have low trapping efficiency. Therefore, methods for trapping aldehydes by chemically reacting the aldehydes with aldehyde trapping agents such as hydrazine derivatives, amines, amino acids, or urea derivatives have been disclosed (see, for example, Patent Documents 1 to 3).

[0004] Japanese Patent Application Publication No. 11-299878 Japanese Patent Application Publication No. 2000-300652 Japanese Patent Application Publication No. 2007-215818

[0005] However, the methods described in these patent documents have problems such as insufficient trapping efficiency and insufficient water resistance, causing the trapping agent applied to a substrate such as a resin or fiber to dissolve when washed with water or laundered, resulting in a decrease in performance. In view of the background of the prior art, the present invention aims to provide a polysiloxane that exhibits a superior aldehyde trapping effect compared to conventionally known trapping techniques, even after washing with water or laundering, a method for producing the same, and a deodorant containing the same.

[0006] As a result of extensive research aimed at solving the above problems, the present inventors have found that the following polysiloxane can solve the above problems, and have thus completed the present invention.

[0007] That is, the present invention includes the following embodiments.

[0008] [1] The following general formula (1)

[0009]

[0010] (In the formula, 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. Each Q independently represents —CH ２ -, -CH ２ CH ２ - and -CH ２ -Ra-CH ２ - (wherein Ra represents an alkylene group having 1 to 18 carbon atoms, and the alkylene group has two or more non-adjacent -CH ２wherein 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. n represents an integer of 1 or 2. When M is an aluminum atom, n is 1, and when M is a silicon atom or a titanium atom, n is 2. An aminooxyalkyl group-containing polysiloxane having a structural unit represented by the following formula: [2] The aminooxyalkyl group-containing polysiloxane according to [1], wherein each R is independently a methyl group, a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, or a hydroxyl group. [3] The aminooxyalkyl group-containing polysiloxane according to [1] or [2], wherein M is a silicon atom and n is 2. [4] The aminooxyalkyl group-containing polysiloxane according to any one of [1] to [3], wherein the volume median diameter is 300 nm or less. [5] A method for producing the aminooxyalkyl group-containing polysiloxane according to [1], characterized by copolymerizing a compound represented by the following general formula (2) with a compound represented by the following general formula (4) and / or (5) in the presence of water:

[0011]

[0012] (In the formula, R １ each independently represents an alkyl group having 1 to 4 carbon atoms; R ２ each independently represents an alkoxy group having 1 to 4 carbon atoms; Q has the same meaning as above; and m represents an integer of 0 to 2.

[0013]

[0014] (In the formula, R １ , R ２ , and m have the same meanings as above.)

[0015]

[0016] (In the formula, R １ and R ２has the same meaning as above. M' represents a silicon atom or a titanium atom. m' represents an integer of 0 to 3.) [6] A method for producing the aminooxyalkyl group-containing polysiloxane according to [1], characterized by copolymerizing a compound represented by the following general formula (2) and a compound represented by the following general formula (3) in the presence of water:

[0017]

[0018] (In the formula, R １ each independently represents an alkyl group having 1 to 4 carbon atoms; R ２ each independently represents an alkoxy group having 1 to 4 carbon atoms; Q has the same meaning as above; and m represents an integer of 0 to 2.

[0019]

[0020] (In the formula, R １ and R ２has the same meaning as above. m' represents an integer of 0 to 3.) [7] The method for producing an aminooxyalkyl group-containing polysiloxane according to [5], wherein the ratio (molar ratio) of the molar amount of the compound represented by general formula (2) to the total molar amount of the compound represented by general formula (4) and the compound represented by general formula (5) is in the range of 0.001 to 1000 per mole of the compound represented by general formula (2). [8] The method for producing an aminooxyalkyl group-containing polysiloxane according to [6], wherein the ratio (molar ratio) of the molar amount of the compound represented by general formula (2) to the molar amount of the compound represented by general formula (3) is in the range of 0.001 to 1000 per mole of the compound represented by general formula (2). [9] A deodorant comprising the aminooxyalkyl group-containing polysiloxane according to [1] or [2].

[10] A deodorizing structure, characterized in that the aminooxyalkyl group-containing polysiloxane according to [1] or [2] is supported on a substrate.

[11] The deodorizing structure according to

[10] , wherein the substrate is a fibrous material, a sheet material, a bead material, a sponge material, or a board material.

[12] A method for removing aldehyde, characterized in that the deodorizing structure according to

[10] is brought into contact with an aldehyde-containing gas.

[0021] The deodorant containing the aminooxyalkyl group-containing polysiloxane of the present invention can rapidly and continuously capture aldehydes, thereby effectively reducing aldehydes harmful to the human body and improving the living environment.

[0022] The present invention is described in detail below. In this specification, the symbol "to" means a numerical range inclusive of both ends. The aminooxyalkyl group-containing polysiloxane of the present invention is characterized by having a structural unit represented by the above general formula (1).

[0023] In 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.

[0024] Examples of the alkyl group having 1 to 4 carbon atoms include, but are not limited to, 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. Examples of the alkoxy group having 1 to 4 carbon atoms include, but are not limited to, 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.

[0025] Among these, R is preferably a methyl group, a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, or a hydroxyl group, because of its excellent aldehyde capturing ability.

[0026] Each Q is independently —CH ２ -, -CH ２ CH ２ - and -CH ２ -Ra-CH ２ - (wherein Ra represents an alkylene group having 1 to 18 carbon atoms, and the alkylene group has two or more non-adjacent -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.) Q is not particularly limited, but specific examples include structures represented by the following chemical formulas (Q-1) to (Q-95).

[0027]

[0028]

[0029] [In the chemical formulas (Q-1) to (Q-95), a hydrogen atom on the alkylene group may be substituted with an alkyl group having 1 to 3 carbon atoms. * represents the bonding position in the general formula (1).] Examples of the alkyl group having 1 to 3 carbon atoms include a methyl group, an ethyl group, a propyl group, and an isopropyl group.

[0030] In general formula (1), M represents an aluminum atom, a silicon atom, or a titanium atom. n represents an integer of 1 or 2. When M is an aluminum atom, n is 1, and when M is a silicon atom or a titanium atom, n is 2. When n is 1, one R is bonded to M. When n is 2, two R are bonded to M. With regard to the above general formula (1), it is preferable that M is a silicon atom and n is 2, i.e., an aminooxyalkyl group-containing polysiloxane represented by the following general formula (1a) is preferred.

[0031]

[0032] (In the formula, R and Q have the same meanings as R and Q in the general formula (1).) The aminooxyalkyl group-containing polysiloxane represented by the general formula (1) is preferably an aminooxyalkyl group-containing polysiloxane represented by the following general formula (1'):

[0033]

[0034] (In the formula, R, Q, M, and n have the same meanings as R, Q, M, and n in the general formula (1).) Furthermore, the aminooxyalkyl group-containing polysiloxane represented by the general formula (1a) is preferably an aminooxyalkyl group-containing polysiloxane represented by the following general formula (1a'):

[0035]

[0036] (In the formula, R and Qn have the same meanings as R and Q in the general formula (1).) As described above, the aminooxyalkyl group-containing polysiloxane of the present invention is a copolymer containing a monomer having an aminooxyalkyl group and a monomer not having an aminooxyalkyl group. With regard to the general formula (1') or (1a') above, this means that the ratio of the monomer having an aminooxyalkyl group to the monomer not having an aminooxyalkyl group, expressed as a molar ratio, is 1 to 0.001 to 1000.

[0037] Regarding the ratio (molar ratio) of the monomer having an aminooxyalkyl group to the monomer not having an aminooxyalkyl group, in terms of excellent aldehyde scavenging ability and ease of production, the "molar amount of the monomer having an aminooxyalkyl group" to the "molar amount of the monomer not having an aminooxyalkyl group" is preferably 1:0.001 to 1000, more preferably 1:0.01 to 100, still more preferably 1:0.01 to 10, still more preferably 1:0.01 to 4, and still more preferably 1:0.01 to 2.

[0038] From the viewpoint of processability, the volume median diameter of the aminooxyalkyl group-containing polysiloxane of the present invention is preferably 1000 nm or less, more preferably 500 nm or less, more preferably 300 nm or less, and even more preferably 200 nm or less. The average particle diameter is the volume average diameter measured by dynamic light scattering. From the viewpoint of aldehyde capture ability, the volume median diameter is preferably 1 to 1000 nm, more preferably 5 to 500 nm, more preferably 10 to 300 nm, and even more preferably 10 to 200 nm.

[0039] The method for producing the aminooxyalkyl group-containing polysiloxane of the present invention is not particularly limited, and examples thereof include a method of copolymerizing a compound represented by the above general formula (2) with a compound represented by the above general formula (4) and / or (5), or a compound represented by the above general formula (2) with a compound represented by the above general formula (3), in the presence of water. Note that, for each of the compounds represented by general formulas (2) to (5), a mixture of multiple compounds in any ratio may be used.

[0040] In the compounds represented by the general formulas (2) to (5), R １ represents an alkyl group having 1 to 4 carbon atoms, and R ２represents an alkoxy group having 1 to 4 carbon atoms. The alkyl group having 1 to 4 carbon atoms is not particularly limited, but 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. The alkoxy group having 1 to 4 carbon atoms is not particularly limited, but 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.

[0041] In the compounds represented by general formula (2) and general formula (4), m represents an integer of 0 to 2. In the compound represented by general formula (5), M' represents a silicon atom or a titanium atom, and m' represents an integer of 0 to 3. In the compound represented by general formula (3), m' represents an integer of 0 to 3.

[0042] Among these, from the viewpoint of copolymerization reaction efficiency, R １ is preferably a methyl group, and R ２ is preferably a methoxy group, an ethoxy group, a propyloxy group, or an isopropyloxy group; m is preferably 0 or 1; and m′ is preferably 0, 1, or 2.

[0043] The copolymerization reaction is carried out in the presence of water, and proceeds by first hydrolyzing the metal alkoxide moiety of the compound represented by general formulas (2) to (5) to generate a metal hydroxide, and then causing intermolecular dehydration condensation.

[0044] The amount of water is not particularly limited, but from the viewpoint of the efficiency of the copolymerization reaction, it is preferably 1 molar equivalent or more relative to the amount of the compound represented by general formula (2), more preferably 1 to 10 molar equivalents relative to the amount of the compound represented by general formula (2), and even more preferably 1 to 5 molar equivalents relative to the amount of the compound represented by general formula (2).

[0045] The copolymerization reaction may be carried out using water as a reaction promoter and solvent, or may be carried out by adding a solvent other than water as necessary.

[0046] The solvent other than water is not particularly limited, but is preferably a solvent that is highly compatible with water, and specific examples include methanol, ethanol, propanol (all of which are alcohol solvents), tetrahydrofuran, dioxane (all of which are ether solvents), acetonitrile, dimethylformamide, dimethyl sulfoxide, and hexamethylphosphotriamide.

[0047] The solvent other than water may be a single solvent or a mixed solvent. The amount of the solvent other than water used is not particularly limited, but is usually 1 to 100 parts by weight per part by weight of the compound represented by general formula (2).

[0048] The molar ratio of the compound represented by general formula (2) to the compound represented by general formula (4) and / or (5) in the copolymerization reaction can be arbitrarily adjusted depending on the purpose and is not particularly limited. However, the total molar amount of the compound represented by general formula (4) and / or (5) relative to 1 mole of the compound represented by general formula (2) is preferably in the range of 0.001 to 1,000, more preferably in the range of 0.01 to 100, more preferably in the range of 0.01 to 10, more preferably in the range of 0.01 to 4, and more preferably in the range of 0.01 to 2.

[0049] The molar ratio of the compound represented by general formula (2) to the compound represented by general formula (3) in the copolymerization reaction can be arbitrarily adjusted depending on the purpose and is not particularly limited. However, the molar amount of the compound represented by general formula (3) relative to 1 mole of the compound represented by general formula (2) is preferably in the range of 0.001 to 1,000, more preferably in the range of 0.01 to 100, more preferably in the range of 0.01 to 10, more preferably in the range of 0.01 to 4, and more preferably in the range of 0.01 to 2.

[0050] The copolymerization reaction is usually carried out in a temperature range of −20 to 200° C., and from the viewpoint of production equipment, a temperature range of 0 to 150° C. is more preferable. The reaction time of the copolymerization reaction is not particularly limited because it varies depending on the concentrations of the compounds represented by general formula (2) and general formulas (3) to (5), the amount of water used, the reaction temperature, etc., but is, for example, several minutes to 14 days.

[0051] The copolymerization mode of the copolymerization reaction is not particularly limited, but examples include random copolymerization, alternating copolymerization, block copolymerization, and graft copolymerization. The molecular shape of the aminooxy group-containing polysiloxane of the present invention is not particularly limited, and it can be any molecular shape, such as linear, branched, or cyclic. After the copolymerization reaction, a mixture containing the aminooxyalkyl group-containing polysiloxane of the present invention is obtained. This mixture may be used as is, or, if necessary, may be purified by distillation, reprecipitation, liquid separation, filtration, column chromatography, or other procedures before use.

[0052] The deodorant of the present invention is characterized by containing the aminooxyalkyl group-containing polysiloxane of the present invention. In addition to the aminooxyalkyl group-containing polysiloxane, the deodorant of the present invention may further contain a solvent, an acid, a base, a binder, a thickener, an antifoaming agent, a surfactant, an antibacterial agent, an antiseptic, or the like.

[0053] The solvent is not particularly limited, but examples thereof include water, methanol, ethanol, propanol, acetonitrile, etc. Among these, water or ethanol is preferred from the viewpoint of safety for the human body (hereinafter, the mixture of the deodorant and the solvent is referred to as a deodorant solution).

[0054] The concentration of the aminooxyalkyl group-containing polysiloxane contained in the deodorant of the present invention is not particularly limited, but is preferably in the range of 0.1 to 50% by weight, more preferably 1 to 30% by weight.

[0055] When the deodorant of the present invention contains the above-mentioned acid or base, the content of the acid or base is not particularly limited, but may be, for example, -ONH ２ The amount is preferably in the range of 0.001 to 10 molar equivalents, more preferably in the range of 0.005 to 5 molar equivalents, and still more preferably in the range of 0.01 to 2 molar equivalents, relative to 1 mole of the group represented by the formula:

[0056] When the deodorant of the present invention contains the binder, thickener, antifoaming agent, surfactant, antibacterial agent, or preservative, the concentrations of the binder, thickener, antifoaming agent, surfactant, antibacterial agent, or preservative are not particularly limited, but are each independently preferably in the range of 0.1 to 30% by weight, more preferably in the range of 0.2 to 25% by weight, and even more preferably in the range of 0.2 to 10% by weight, where the total amount of the deodorant solution of the present invention is 100% by weight.

[0057] The method for obtaining the deodorant of the present invention is not particularly limited, but an example thereof is a method in which the aminooxyalkyl group-containing polysiloxane of the present invention and a solvent are mixed and stirred.

[0058] The method of using the deodorant of the present invention is not particularly limited, but examples thereof include a method of applying or spraying the deodorant onto a substrate, a method of spraying it onto an odor source, etc. The deodorant structure of the present invention refers to one in which the above-mentioned aminooxyalkyl group-containing polysiloxane is supported on a substrate.

[0059] The substrate of the deodorizing structure of the present invention is not particularly limited, but examples thereof include fibrous materials, sheet-like materials, bead-like materials, sponge-like materials, and board-like materials.

[0060] More specifically, examples include polyester fibers, polyamide fibers, polyacrylonitrile fibers, polypropylene fibers, polyethylene fibers, polyvinyl chloride fibers, fluorine-based fibers, aramid fibers, sulfone fibers, rayon, acetate, cotton, wool, silk, hemp, glass fibers, carbon fibers, ceramic fibers, mixed fibers thereof, woven fabrics made of these fibers, knitted fabrics made of these fibers, nonwoven fabrics made of these fibers, threads made of these fibers, ropes made of these fibers, strings made of these fibers, and sheet-like, bead-like, or sponge-like materials made of a material selected from the group consisting of polyester resins, polyamide resins, polyethylene resins, polypropylene resins, fluorine-based resins, silicone resins, polyimide resins, polyvinyl chloride resins, natural rubber, and synthetic rubber, as well as wood, plywood, and gypsum board.

[0061] The deodorizing structure of the present invention can be used for any purpose depending on the purpose and use. The use is not particularly limited, but it can be used for, for example, clothing, curtains, carpets, wall coverings, automobile interior materials, furniture, etc.

[0062] The method for producing the deodorizing structure of the present invention is not particularly limited, but examples thereof include a method in which the aminooxyalkyl group-containing polysiloxane of the present invention or the deodorizing agent is supported on a substrate.

[0063] The method for supporting the aminooxyalkyl group-containing polysiloxane or the deodorant on a substrate is not particularly limited, but examples thereof include a method of applying the deodorant solution to the substrate and a method of immersing the substrate in the deodorant solution.

[0064] The amount of the aminooxyalkyl group-containing polysiloxane carried on the substrate can be adjusted as desired depending on the purpose, and is not particularly limited. However, the amount of the aminooxyalkyl group-containing polysiloxane carried on the substrate is preferably 0.1 to 100 g / m. ２ The range is preferably 0.5 to 50 g / m ２ The range is more preferable.

[0065] After the aminooxyalkyl group-containing polysiloxane or the deodorant is supported on the substrate, the obtained deodorant structure may be dried as needed. The drying conditions can be adjusted as desired depending on the purpose and are not particularly limited, but for example, the temperature is in the range of 0 to 200°C and the time is in the range of several minutes to 48 hours.

[0066] 1 shows mass spectrometry data for the aminooxyalkyl group-containing polysiloxane obtained in Example 1.

[0067] The present invention will be described in more detail below with reference to examples, but these examples are provided to aid in the understanding of the present invention and are not intended to limit the scope of the present invention in any way. Unless otherwise specified, commercially available reagents and the like were used.

[0068] The following abbreviations are used for the compounds used in the examples.

[0069] O-[3-(triethoxysilyl)propyl]hydroxylamine = Si-1 O-[3-(trimethoxysilyl)propyl]hydroxylamine = Si-2 O-[3-[diethoxy(methyl)silyl]propyl]hydroxylamine = Si-3 O-[3-[dimethoxy(methyl)silyl]propyl]hydroxylamine = Si-4 1-[2-(aminooxy)ethyl]-3-[3-(trimethoxysilyl)propyl]urea = Si-5 1-[2-(aminooxy)ethyl]-N-[3-(trimethoxysilyl)propyl]carbamate = Si-6 2-aminooxy-N-[3-(trimethoxysilyl)propyl]acetamide = Si-7 2-aminooxy-N-[3-(trimethoxysilyl)propyl]propanamide = Si-8 Tetraethoxysilane = TEOS Methyltriethoxysilane = MTEOS

[0070]

[0071] Example 1 <Preparation of Deodorant> Si-1 (1.62 g, 8.28 mmol), TEOS (0.513 g, 2.46 mmol), and water (21.2 g) were placed in a graduated centrifuge tube and stirred at room temperature for 7 days to obtain a translucent solution-like dispersion containing the aminooxyalkyl group-containing polysiloxane of the present invention. The reaction system was initially two-phase, but became homogeneous over time, suggesting that the copolymerization reaction had progressed. The molecular weight of the obtained aminooxyalkyl group-containing polysiloxane was measured using a mass spectrometer (Bruker Daltonics, microTOF), resulting in the spectral data shown in Figure 1, confirming the formation of a polymer. The volume median diameter of this aminooxyalkyl group-containing polysiloxane was measured by dynamic light scattering using a measuring device (model: ELSZ-2000) manufactured by Otsuka Electronics Co., Ltd., and was found to be 5 nm.

[0072] <Preparation of Deodorizing Structure> 0.1 g of the translucent solution-like dispersion obtained in the above reaction was applied to a 100% cotton fabric measuring 5 cm in length and 10 cm in width, and dried at 60°C for 1 hour using a hot air dryer (DRJ433DA, manufactured by Advantec Co., Ltd.) to obtain a deodorizing structure in which the aminooxyalkyl group-containing polysiloxane was immobilized (amount of immobilized aminooxy group=35 μmol).

[0073] <Acetaldehyde Capture Test> The deodorizing structure was sealed in a 10 L Tedlar bag, and then 5 L of nitrogen gas with an acetaldehyde concentration of 10 ppm was added to the Tedlar bag. After standing at room temperature for 2 hours, the gas in the Tedlar bag was adsorbed onto a cartridge (Presep-C DNPH, manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) carrying 2,4-dinitrophenylhydrazine (DNPH). This cartridge was treated with acetonitrile to elute the DNPH-aldehyde condensate. Subsequently, the acetaldehyde concentration of the eluate was quantified using a liquid chromatograph (LC-2030C Plus, manufactured by Shimadzu Corporation). Furthermore, the acetaldehyde capture rate was calculated using the following formula.

[0074] Acetaldehyde capture rate [%] = [(initial acetaldehyde concentration - residual acetaldehyde concentration) ÷ initial acetaldehyde concentration] × 100 Examples 2 to 35, Reference Examples 1 to 6 Examples 2 to 35 and Reference Examples 1 to 6 were carried out in the same manner as Example 1, except that the raw material composition or preparation conditions were changed to those shown in Table 1 when preparing the deodorant. In preparing the deodorant structure, the amount of aminooxy groups immobilized relative to the fiber was 35 μmol, the same as in Example 1. In Table 1, the compound represented by general formula (2) was referred to as monomer A, and the compounds represented by general formulas (3) to (5) were referred to as monomer B. The measurement results of the volume median diameter and the aldehyde capture rate are shown in Table 2.

[0075] Comparative Example 1 A deodorizing structure was prepared in the same manner as in Example 1, except that, instead of applying 0.1 g of the translucent solution dispersion to a piece of 100% cotton fabric measuring 5 cm in length and 10 cm in width, 0.1 g of a 5% aqueous solution of adipic acid dihydrazide was applied to a piece of 100% cotton fabric measuring 5 cm in length and 10 cm in width, and the aldehyde capture rate thereof was measured.

[0076] Comparative Example 2 An odor eliminating structure was prepared in the same manner as in Example 1, except that, instead of applying 0.1 g of the translucent solution dispersion to a piece of 100% cotton fabric measuring 5 cm in length and 10 cm in width, 0.2 g of a 5% aqueous solution of adipic acid dihydrazide was applied to a piece of 100% cotton fabric measuring 5 cm in length and 10 cm in width, and the aldehyde capture rate thereof was measured.

[0077] The results of Examples 1 to 35, Reference Examples 1 to 6, and Comparative Examples 1 and 2 are shown in Table 2. As is clear from Table 2, the deodorants of the present invention exhibited superior aldehyde capturing ability compared to existing deodorants.

[0078]

[0079]

[0080] Example 36 The deodorizing structure obtained in Example 1 was washed once or five times in accordance with the testing method for washing durability (JIS L 0217 103). The deodorizing structure after one wash and the deodorizing structure after five washes were subjected to an acetaldehyde capture test in the same manner as in Example 1.

[0081] Example 37 A deodorizing structure was prepared in the same manner as in Example 1, except that drying at 110°C for 40 minutes was performed instead of drying at 60°C for 1 hour, and an acetaldehyde capture test was performed. The deodorizing structure was washed once or five times in accordance with the washing durability test method (JIS L 0217 103). The deodorizing structure after one wash and the deodorizing structure after five washes were subjected to an acetaldehyde capture test in the same manner as in Example 1.

[0082] Example 38 The deodorizing structure obtained in Example 6 was washed once or five times in accordance with the testing method for washing durability (JIS L 0217 103). The deodorizing structure after one wash and the deodorizing structure after five washes were subjected to an acetaldehyde capture test in the same manner as in Example 1.

[0083] Example 39 A deodorizing structure was prepared in the same manner as in Example 6, except that drying at 60°C for 1 hour in Example 6 was changed to drying at 110°C for 40 minutes, and an acetaldehyde capture test was carried out. The deodorizing structure was washed once or five times in accordance with the washing durability test method (JIS L 0217 103 method). The deodorizing structure after one wash and the deodorizing structure after five washes were subjected to an acetaldehyde capture test in the same manner as in Example 1.

[0084] The deodorizing structure obtained in Comparative Example 1 was washed once or five times in accordance with the testing method for washing durability (JIS L 0217 103). The deodorizing structure after one wash and the deodorizing structure after five washes were subjected to an acetaldehyde capture test in the same manner as in Comparative Example 1.

[0085] Comparative Example 4 A deodorizing structure was produced in the same manner as in Comparative Example 1, except that drying at 110°C for 40 minutes was performed instead of drying at 60°C for 1 hour, and an acetaldehyde capture test was performed. The deodorizing structure was washed once or five times in accordance with the washing durability test method (JIS L 0217 103 method). The deodorizing structure after one wash and the deodorizing structure after five washes were subjected to an acetaldehyde capture test in the same manner as in Comparative Example 1.

[0086] The results of Examples 36 to 39 and Comparative Examples 3 and 4 are shown in Table 3. As is clear from Table 3, the deodorants of the present invention exhibited superior water resistance compared to existing deodorants.

[0087]

[0088] The entire contents of the specifications, claims, drawings and abstracts of Japanese Patent Application No. 2022-117668 filed on July 25, 2022 and Japanese Patent Application No. 2023-018847 filed on February 10, 2023 are hereby cited and incorporated as the disclosure of the specification of the present invention.

[0089] The aminooxyalkyl group-containing polysiloxane of the present invention quickly and continuously captures aldehydes, thereby reducing odors caused by aldehydes and improving the human living environment.

Claims

1. The following general formula (1) 【Chemistry 1】 (In the formula, 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. Q independently represents -CH ２ -ien-CH ２ CH ２ -, and -CH ２ -Ra-CH ２ A group selected from the group consisting of (where Ra represents an alkylene group having 1 to 18 carbon atoms, and the alkylene group has two or more non-adjacent groups) ２ Each of the hyphens may 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 atoms of the alkylene group may be substituted with alkyl groups having 1 to 3 carbon atoms. M represents an aluminum atom, a silicon atom, or a titanium atom. n represents an integer of 1 or 2. When M is an aluminum atom, n is 1, and when M is a silicon atom or a titanium atom, n is 2. A polysiloxane containing an aminooxyalkyl group having a structural unit represented by [the given symbol].

2. The aminooxyalkyl group-containing polysiloxane according to claim 1, wherein R is independently a methyl group, a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, or a hydroxyl group.

3. The aminooxyalkyl group-containing polysiloxane according to claim 1, wherein M is a silicon atom and n is 2.

4. The aminooxyalkyl group-containing polysiloxane according to claim 1, wherein the volume median diameter is 300 nm or less.

5. A method for producing an aminooxyalkyl group-containing polysiloxane according to claim 1, characterized by copolymerizing a compound represented by the following general formula (2) with a compound represented by the following general formula (4) and / or (5) in the presence of water. 【Chemistry 2】 (In the formula, R １ Each of these independently represents an alkyl group having 1 to 4 carbon atoms, R ２ Each of these independently represents an alkoxy group having 1 to 4 carbon atoms. Q has the same meaning as above. m represents an integer from 0 to 2. 【Transformation 3】 (wherein, R １ , R ２ , and m represent the same meanings as described above.) 【Chemistry 4】 (In the formula, R １ and R ２ The above has the same meaning. M' represents a silicon atom or a titanium atom. m' represents an integer from 0 to 3.

6. A method for producing an aminooxyalkyl group-containing polysiloxane according to claim 1, characterized by copolymerizing a compound represented by the following general formula (2) with a compound represented by the following general formula (3) in the presence of water. 【Transformation 5】 (In the formula, R １ Each of these independently represents an alkyl group having 1 to 4 carbon atoms, R ２ Each of these independently represents an alkoxy group having 1 to 4 carbon atoms. Q has the same meaning as above. m represents an integer from 0 to 2. 【Transformation 6】 (In the formula, R １ and R ２ (This has the same meaning as above. m' represents an integer from 0 to 3.)

7. A method for producing an aminooxyalkyl group-containing polysiloxane according to claim 5, wherein the ratio (molar ratio) of the molar amount of the compound represented by the general formula (2) to the total molar amount of the compound represented by the general formula (4) and the compound represented by the general formula (5) is in the range of 0.001 to 1000 for every 1 mole of the compound represented by the general formula (2).

8. A method for producing an aminooxyalkyl group-containing polysiloxane according to claim 6, wherein the ratio (molar ratio) of the molar amount of the compound represented by the general formula (2) to the molar amount of the compound represented by the general formula (3) is in the range of 0.001 to 1000 for every 1 mole of the compound represented by the general formula (2).

9. A deodorant comprising the aminooxyalkyl group-containing polysiloxane described in claim 1.

10. A deodorizing structure characterized in that the aminooxyalkyl group-containing polysiloxane described in claim 1 is supported on a substrate.

11. The deodorizing structure according to claim 10, wherein the base material is a fibrous material, a sheet material, a bead material, a sponge material, or a board material.

12. A method for removing aldehydes, characterized by bringing the deodorizing structure described in claim 10 into contact with an aldehyde-containing gas.

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