Polysiloxane, method for producing same, and deodorant containing same

Abstract

Provided is a deodorant having excellent trapping efficiency and water resistance. An aminooxyalkyl group-containing polysiloxane having a structural unit represented by general formula (1) is used. # imgabs0 #

Description

Technical Field

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

[0002] Aldehydes such as acetaldehyde and formaldehyde are representative odor substances in the living environment. Since the odor threshold is extremely low, even low concentrations can cause unpleasant odors. These aldehydes are known to be produced by synthetic resins, plywood, cigarette smoke, etc. indoors and in cars, and are the cause of sick building syndrome and new car syndrome. In addition, these aldehydes are also suspected to be carcinogenic, and when people are exposed to these aldehydes on a daily basis, there is a risk of health damage. Therefore, the Ministry of Health, Labor and Welfare of Japan stipulates that as indoor concentration guide values, acetaldehyde is 0.03ppm and formaldehyde is 0.08ppm. Therefore, a means of quickly and continuously removing aldehydes is sought.

[0003] Since low-level aldehydes such as acetaldehyde and formaldehyde have low boiling points, the capture efficiency is low when using inorganic porous materials such as silica gel and activated carbon, which are commonly used as deodorants. Therefore, a method of capturing aldehydes by chemically reacting aldehyde capture agents including hydrazine derivatives, amines, amino acids, or urea derivatives with aldehydes has been disclosed (for example, see Patent Documents 1 to 3).

[0004] Prior art literature

[0005] Patent Literature

[0006] Patent Document 1: Japanese Patent Application Laid-Open No. 11-299878

[0007] Patent Document 2: Japanese Patent Application Publication No. 2000-300652

[0008] Patent Document 3: Japanese Patent Application Laid-Open No. 2007-215818 Summary of the invention

[0009] Problem that the invention aims to solve

[0010] However, the methods described in these patent documents have problems such as insufficient capture efficiency and insufficient water resistance, so the capture agent applied to a substrate such as a resin or fiber is eluted by washing or cleaning, resulting in reduced performance.

[0011] In view of the above-mentioned background of the prior art, an object of the present invention is to provide a polysiloxane which exhibits a superior aldehyde capturing effect compared with conventionally known capturing technologies even when washed with water or cleansed, a method for producing the same, and a deodorant containing the same.

[0012] Solutions for solving problems

[0013] The present inventors have conducted intensive studies to solve the above-mentioned problems and, as a result, have found that the following polysiloxane can solve the above-mentioned problems, thereby completing the present invention.

[0014] That is, the present invention includes the following embodiments.

[0015] [1] An aminooxyalkyl group-containing polysiloxane having a structural unit represented by the following general formula (1).

[0016]

[0017] (In the formula, R each 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 each independently represents a group selected from the group consisting of -CH2-, -CH2CH2-, and -CH2-Ra-CH2- (wherein Ra represents an alkylene group having 1 to 18 carbon atoms, and two or more non-adjacent -CH2- in the aforementioned alkylene group are each independently optionally replaced by -O-, -(C=O)O-, -O(C=O)-, -O(C=O)-O-, -C(=O)-NH-, -NH-(C=O)-, -CH=CH-, -C≡C-, and the hydrogen atom of the aforementioned alkylene group is optionally replaced 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.) [2]

[0019] The aminooxyalkyl group-containing polysiloxane according to [1], wherein each R is independently a methyl group, a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group or a hydroxyl group. [3]

[0021] The aminooxyalkyl group-containing polysiloxane according to [1] or [2], wherein M is a silicon atom and n is 2. [4]

[0023] The aminooxyalkyl group-containing polysiloxane according to any one of [1] to [3], wherein the volume median particle size is 300 nm or less. [5]

[0025] A method for producing an aminooxyalkyl group-containing polysiloxane according to [1], characterized in that a compound represented by the following general formula (2) and a compound represented by the following general formula (4) and / or general formula (5) are copolymerized in the presence of water.

[0026]

[0027] (Where R 1 Each independently represents an alkyl group having 1 to 4 carbon atoms, and R 2Each independently represents an alkoxy group having 1 to 4 carbon atoms. Q has the same meaning as above. m represents an integer of 0 to 2.

[0028] R 1 m -Al-R 2 3-m (4)

[0029] (Where R 1 , R 2 and m have the same meanings as above.)

[0030] R 1 m′ -M′-R 2 4-m′ (5)

[0031] (Where R 1 and R 2 represents the same meaning as above. M' represents a silicon atom or a titanium atom. m' represents an integer of 0 to 3. [6]

[0033] A method for producing an aminooxyalkyl group-containing polysiloxane according to [1], characterized in that a compound represented by the following general formula (2) and a compound represented by the following general formula (3) are copolymerized in the presence of water.

[0034]

[0035] (Where R 1 Each independently represents an alkyl group having 1 to 4 carbon atoms, and R 2 Each independently represents an alkoxy group having 1 to 4 carbon atoms. Q has the same meaning as above. m represents an integer of 0 to 2.

[0036] R 1 m′ -Si-R 2 4-m′ (3)

[0037] (Where R 1 and R 2 represents the same meaning as above. m' represents an integer of 0 to 3.) [7]

[0039] The method for producing an aminooxyalkyl group-containing polysiloxane according to [5], wherein the ratio of the total molar amount of the compound represented by the general formula (4) and the compound represented by the general formula (5) to the molar amount of the compound represented by the general formula (2) (molar ratio) is such that 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 per 1 mole of the compound represented by the general formula (2). [8]

[0041] 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 the general formula (3) to the molar amount of the compound represented by the general formula (2) is in the range of 0.001 to 1000 per 1 mole of the compound represented by the general formula (2). [9]

[0043] A deodorant comprising the aminooxyalkyl group-containing polysiloxane according to [1] or [2].

[10]

[0045] A deodorant structure, characterized in that the aminooxyalkyl-containing polysiloxane described in [1] or [2] is supported on a substrate.

[11]

[0047] The deodorant structure according to

[10] , wherein the substrate is a fiber-like object, a sheet-like object, a bead-like object, a sponge-like object or a plate-like object.

[12]

[0049] A method for removing aldehydes, characterized in that the deodorizing structure described in

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

[0050] Effects of the Invention

[0051] The deodorant containing the aminooxyalkyl group-containing polysiloxane of the present invention can rapidly and continuously capture aldehydes. As a result, it is effective in reducing aldehydes that are harmful to the human body and has the effect of improving the living environment. DETAILED DESCRIPTION

[0052] Hereinafter, the present invention will be described in detail. It should be noted that, in the present specification, "to" means a numerical range of above or below including both numerical values.

[0053] The aminooxyalkyl group-containing polysiloxane of the present invention is characterized by having a structural unit represented by the above general formula (1).

[0054] In the general formula (1), R each independently represents an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a hydroxy group.

[0055] The alkyl group having 1 to 4 carbon atoms is not particularly limited, and examples thereof include methyl group, ethyl group, propyl group, isopropyl group, butyl group, 2-methylpropyl group, 1-methylpropyl group, and tert-butyl group.

[0056] The alkoxy group having 1 to 4 carbon atoms is not particularly limited, and examples thereof include methoxy, ethoxy, propoxy, isopropoxy, butoxy, 2-methylpropoxy, 1-methylpropoxy, and tert-butoxy groups.

[0057] Among these, R is preferably a methyl group, a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group or a hydroxyl group in terms of excellent aldehyde capture.

[0058] Q each independently represents a group selected from the group consisting of -CH2-, -CH2CH2- and -CH2-Ra-CH2- (wherein Ra represents an alkylene group having 1 to 18 carbon atoms, and two or more non-adjacent -CH2- in the aforementioned alkylene group are each independently optionally replaced by -O-, -(C=O)O-, -O(C=O)-, -O(C=O)-O-, -C(=O)-NH-, -NH-(C=O)-, -CH=CH-, -C≡C-, and the hydrogen atom of the aforementioned alkylene group is optionally substituted by an alkyl group having 1 to 3 carbon atoms.).

[0059] Q is not particularly limited, and specific examples thereof include structures represented by the following chemical formulae (Q-1) to (Q-95).

[0060]

[0061]

[0062] [In the above chemical formulas (Q-1) to (Q-95)), the hydrogen atoms on the alkylene group may be substituted by an alkyl group having 1 to 3 carbon atoms. * represents the bonding position in the above general formula (1).]

[0063] 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.

[0064] In the 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 Rs are bonded to M.

[0065] In the above general formula (1), preferably, M is a silicon atom, n is 2, that is, an aminooxyalkyl group-containing polysiloxane represented by the following general formula (1a).

[0066]

[0067] (In the formula, R and Q have the same meanings as R and Q in the aforementioned general formula (1).)

[0068] The aminooxyalkyl group-containing polysiloxane represented by the above general formula (1) is preferably an aminooxyalkyl group-containing polysiloxane represented by the following general formula (1′).

[0069]

[0070] (In the formula, R, Q, M and n have the same meanings as those in the aforementioned general formula (1).)

[0071] 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′).

[0072]

[0073] (In the formula, R and Qn have the same meanings as R and Q in the aforementioned general formula (1).)

[0074] As described above, the aminooxyalkyl-containing polysiloxane of the present invention is a copolymer containing a monomer having an aminooxyalkyl group and a monomer not having an aminooxyalkyl group. Regarding the above general formula (1') or (1a'), if the ratio of the monomer having an aminooxyalkyl group to the monomer not having an aminooxyalkyl group is expressed by a molar ratio, it is expressed as 1 to 0.001 to 1000.

[0075] Regarding the ratio (molar ratio) of the monomer having an aminooxyalkyl group to the monomer not having an aminooxyalkyl group, from the perspective of excellent aldehyde capturing ability and ease of manufacturing, 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 to 0.001 to 1000, more preferably 1 to 0.01 to 100, more preferably 1 to 0.01 to 10, more preferably 1 to 0.01 to 4, and more preferably 1 to 0.01 to 2.

[0076] From the viewpoint of processability, the volume median particle size 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 further preferably 200 nm or less. It should be noted that the average particle size is a volume average diameter measured by a dynamic light scattering method.

[0077] The volume median particle size 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, from the viewpoint of aldehyde capturing ability.

[0078] 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 the compound represented by the general formula (2) and the compound represented by the general formula (4) and / or (5), or a method of copolymerizing the compound represented by the general formula (2) and the compound represented by the general formula (3) in the presence of water.

[0079] In addition, regarding the compounds represented by general formulae (2) to (5), a mixture of a plurality of compounds at an arbitrary ratio may be used.

[0080] In the compounds represented by general formulas (2) to (5), R 1 represents an alkyl group having 1 to 4 carbon atoms, R 2 It represents an alkoxy group having 1 to 4 carbon atoms.

[0081] The alkyl group having 1 to 4 carbon atoms is not particularly limited, and examples thereof include methyl group, ethyl group, propyl group, isopropyl group, butyl group, 2-methylpropyl group, 1-methylpropyl group, and tert-butyl group.

[0082] The alkoxy group having 1 to 4 carbon atoms is not particularly limited, and examples thereof include methoxy, ethoxy, propoxy, isopropoxy, butoxy, 2-methylpropoxy, 1-methylpropoxy, and tert-butoxy groups.

[0083] In the compounds represented by the general formula (2) and the general formula (4), m represents an integer of 0-2.

[0084] In the compound represented by the general formula (5), M' represents a silicon atom or a titanium atom, and m' represents an integer of 0-3.

[0085] In the compound represented by the general formula (3), m' represents an integer of 0-3.

[0086] Among them, from the viewpoint of the efficiency of the copolymerization reaction, R 1 Preferably, methyl, R 2 It is preferably a methoxy group, an ethoxy group, a propoxy group or an isopropoxy group, m is preferably 0 or 1, and m' is preferably 0, 1 or 2.

[0087] The copolymerization reaction is carried out in the presence of water. First, the metal alkoxide sites of the compounds represented by the general formulae (2) to (5) are hydrolyzed to generate metal hydroxides, and then dehydration condensation occurs between the molecules, thereby advancing the copolymerization reaction.

[0088] The amount of the water is not particularly limited. 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 the general formula (2), more preferably 1 to 10 molar equivalents relative to the amount of the compound represented by the general formula (2), and more preferably 1 to 5 molar equivalents relative to the amount of the compound represented by the general formula (2).

[0089] The copolymerization reaction may be carried out using water as a reaction accelerator and solvent, or may be carried out by adding a solvent other than water as necessary.

[0090] The solvent other than the aforementioned water is not particularly limited, but preferably a solvent having high compatibility with water. Specific examples include methanol, ethanol, propanol (the above are alcohol solvents), tetrahydrofuran, dioxane (the above are ether solvents), acetonitrile, dimethylformamide, dimethyl sulfoxide or hexamethylphosphoric triamide.

[0091] The solvent other than water may be a single solvent or a mixed solvent.

[0092] The amount of the solvent other than water used is not particularly limited, but is usually 1 to 100 parts by weight based on 1 part by weight of the compound represented by the general formula (2).

[0093] The molar ratio of the compound represented by the general formula (4) and / or (5) to the compound represented by the general formula (2) in the copolymerization reaction can be arbitrarily adjusted according to the purpose and is not particularly limited. The total molar amount of the compound represented by the general formula (4) and / or (5) relative to 1 mole of the compound represented by the general formula (2) is preferably in the range of 0.001 to 1000, 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.

[0094] The molar ratio of the compound represented by the general formula (3) to the compound represented by the general formula (2) in the copolymerization reaction can be arbitrarily adjusted according to the purpose and is not particularly limited. The molar amount of the compound represented by the general formula (3) relative to 1 mole of the compound represented by the general formula (2) is preferably in the range of 0.001 to 1000, 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.

[0095] The copolymerization reaction is usually carried out at a temperature ranging from 20 to 200°C, and more preferably at a temperature ranging from 0 to 150°C from the viewpoint of production equipment.

[0096] The reaction time of the copolymerization reaction varies depending on the concentrations of the compounds represented by the general formula (2) and general formulae (3) to (5), the amount of water used, the reaction temperature, etc., and is not particularly limited, but is, for example, several minutes to 14 days.

[0097] The copolymerization method of the copolymerization reaction is not particularly limited, and examples thereof include random copolymerization, alternating copolymerization, block copolymerization, and graft copolymerization.

[0098] The molecular shape of the aminooxy group-containing polysiloxane of the present invention is not particularly limited, and any molecular shape such as a linear, branched, or cyclic shape may be adopted.

[0099] After the copolymerization reaction, a mixture containing the aminooxyalkyl group-containing polysiloxane of the present invention can be obtained, which can be used as it is or can be used after being purified by distillation, reprecipitation, liquid separation, filtration or column chromatography as required.

[0100] The deodorant of the present invention is characterized by comprising the aminooxyalkyl group-containing polysiloxane of the present invention.

[0101] The deodorant of the present invention may contain, in addition to the aforementioned aminooxyalkyl group-containing polysiloxane, a solvent, an acid, an alkali, a binder, a thickener, a defoaming agent, a surfactant, an antibacterial agent, an antiseptic, or the like.

[0102] The solvent is not particularly limited, and examples thereof include water, methanol, ethanol, propanol, acetonitrile, etc. Among them, water or ethanol is preferred from the viewpoint of safety to the human body (hereinafter, a mixture of a deodorant and a solvent is referred to as a deodorant solution).

[0103] 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, and more preferably in the range of 1 to 30% by weight.

[0104] When the deodorant of the present invention contains the aforementioned acid or base, the content of the acid or base is not particularly limited, but 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 even more preferably in the range of 0.01 to 2 molar equivalents, relative to 1 mole of the group represented by -ONH2.

[0105] When the deodorant of the present invention contains the aforementioned binder, thickener, defoamer, surfactant, antibacterial agent or preservative, the concentration of the aforementioned binder, thickener, defoamer, surfactant, antibacterial agent or preservative is not particularly limited. Taking the total amount of the deodorant solution of the present invention as 100 weight %, each independently preferably ranges from 0.1 to 30 weight %, more preferably ranges from 0.2 to 25 weight %, and more preferably ranges from 0.2 to 10 weight %.

[0106] The method for obtaining the deodorant of the present invention is not particularly limited, and examples thereof include a method of mixing the aminooxyalkyl group-containing polysiloxane of the present invention and a solvent and stirring the mixture.

[0107] The method of using the deodorant of the present invention is not particularly limited, and examples thereof include a method of applying or spraying the deodorant onto a substrate and a method of spraying the deodorant onto an odor generation source.

[0108] The deodorant structure of the present invention refers to a structure in which the above-mentioned aminooxyalkyl group-containing polysiloxane is supported on a substrate.

[0109] The substrate of the deodorant structure of the present invention is not particularly limited, and examples thereof include fibrous materials, sheet materials, beads, sponges, and plates.

[0110] More specifically, examples include polyester fibers, polyamide fibers, polyacrylonitrile fibers, polypropylene fibers, polyethylene fibers, polyvinyl chloride fibers, fluorine fibers, aramid fibers, sulfone fibers, rayon, acetate, cotton, wool, silk, linen, glass fibers, carbon fibers, ceramic fibers, mixed fibers thereof, woven fabrics containing these fibers, knitted fabrics containing these fibers, nonwoven fabrics containing these fibers, yarns containing these fibers, ropes containing these fibers, belts containing these fibers, or sheets formed from raw materials selected from the group consisting of polyester resins, polyamide resins, polyethylene resins, polypropylene resins, fluorine resins, silicone resins, polyimide resins, polyvinyl chloride resins, natural rubber and synthetic rubber, beads formed from these raw materials, sponges formed from these raw materials, wood, plywood, or gypsum boards.

[0111] The deodorant structure of the present invention can be used for any purpose according to the purpose and application. The application is not particularly limited, and it can be used for clothing, curtains, carpets, wall decoration materials, automobile interior materials, furniture, etc.

[0112] The method for producing the deodorant structure of the present invention is not particularly limited, and examples thereof include a method in which the aminooxyalkyl group-containing polysiloxane of the present invention or the above-mentioned deodorant is supported on a substrate.

[0113] The method for supporting the aminooxyalkyl group-containing polysiloxane or the deodorant on the substrate is not particularly limited, and examples thereof include a method of applying the deodorant solution on the substrate and a method of immersing the substrate in the deodorant solution.

[0114] The amount of the aminooxyalkyl-containing polysiloxane loaded on the substrate can be adjusted arbitrarily according to the purpose and is not particularly limited. The amount of the aminooxyalkyl-containing polysiloxane loaded on the substrate is preferably 0.1 to 100 g / m 2 The range is more preferably 0.5 to 50 g / m 2 range.

[0115] After the aminooxyalkyl-containing polysiloxane or the above-mentioned deodorant is loaded on the substrate, the obtained deodorant structure can be dried as needed. The drying conditions can be arbitrarily adjusted according to the purpose and are not particularly limited, 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. BRIEF DESCRIPTION OF THE DRAWINGS

[0116] Figure 1 This is the mass spectrum data of the aminooxyalkyl group-containing polysiloxane obtained in Example 1.

[0117] Example

[0118] The present invention will be described in further detail below based on examples, but these are examples for helping to understand the present invention, and the present invention is not limited to these examples. It should be noted that the reagents used were commercially available unless otherwise specified.

[0119] In addition, the following abbreviations are used for the compounds used in Examples.

[0120] O-[3-(Triethoxysilyl)propyl]hydroxylamine=Si-1

[0121] O-[3-(Trimethoxysilyl)propyl]hydroxylamine=Si-2

[0122] O-[3-[diethoxy(methyl)silyl]propyl]hydroxylamine=Si-3

[0123] O-[3-[dimethoxy(methyl)silyl]propyl]hydroxylamine=Si-4

[0124] 1-[2-(aminooxy)ethyl]-3-[3-(trimethoxysilyl)propyl]urea=Si-5

[0125] 1-[2-(aminooxy)ethyl]-N-[3-(trimethoxysilyl)propyl]carbamate=Si-6

[0126] 2-aminooxy-N-[3-(trimethoxysilyl)propyl]acetamide=Si-7

[0127] 2-aminooxy-N-[3-(trimethoxysilyl)propyl]propionamide=Si-8

[0128] Tetraethoxysilane = TEOS

[0129] Methyltriethoxysilane=MTEOS

[0130]

[0131] Example 1

[0132] <Preparation of Deodorant>

[0133] Si-1 (1.62 g, 8.28 mmol), TEOS (0.513 g, 2.46 mmol) and water (21.2 g) were added to a graduated centrifuge tube and stirred at room temperature for 7 days to obtain a semi-transparent solution dispersion containing the aminooxyalkyl-containing polysiloxane of the present invention. The reaction system was initially a two-phase system, but became a uniform system over time, suggesting that the copolymerization reaction proceeded. The molecular weight of the obtained aminooxyalkyl-containing polysiloxane was measured using a mass spectrometer (Bruker Daltonics, microTOF), and the result was Figure 1 The spectral data shown above confirmed the formation of a polymer. The volume median particle size of the aminooxyalkyl group-containing polysiloxane was measured by a dynamic light scattering method using a measuring device (model: ELSZ-2000) manufactured by Otsuka Electronics Co., Ltd. and was found to be 5 nm.

[0134] <Preparation of Deodorant Structure>

[0135] 0.1 g of the translucent liquid dispersion obtained in the above reaction was applied to 100% cotton fibers of 5 cm in length and 10 cm in width, and dried at 60°C for 1 hour using a hot air dryer (manufactured by ADVANTEC.CO.LTD., DRJ433DA), thereby obtaining a deodorant structure having an aminooxyalkyl-containing polysiloxane fixed thereto (aminooxy group fixed amount = 35 μmol).

[0136] <Acetaldehyde capture test>

[0137] The deodorant structure is sealed in a 10L Tedlar bag, and then 5L of nitrogen gas with an acetaldehyde concentration of 10ppm is added to the Tedlar bag. After standing at room temperature for 2 hours, the gas in the Tedlar bag is adsorbed on a cylinder (manufactured by FUJIFILM Wako Pure Chemical Corporation, Presep-C DNPH) loaded with 2,4-dinitrophenylhydrazine (DNPH). The cylinder is treated with acetonitrile to dissolve the DNPH-aldehyde condensate. Then, for the eluent, the acetaldehyde concentration is quantified using a liquid chromatography (manufactured by Shimadzu Corporation, LC-2030C Plus). Furthermore, the acetaldehyde capture rate is calculated according to the following formula.

[0138] Acetaldehyde capture rate [%] = [(initial acetaldehyde concentration - residual acetaldehyde concentration) ÷ initial acetaldehyde concentration] × 100

[0139] Examples 2 to 35, Reference Examples 1 to 6

[0140] 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 the preparation of the deodorizing structure, the amount of aminooxy group fixed to the fiber was set to 35 μmol, the same as in Example 1. It should be noted that in Table 1, the compound represented by the general formula (2) is referred to as monomer A, and the compounds represented by the general formulas (3) to (5) are referred to as monomer B. The measurement results of the volume median particle size and the aldehyde capture rate are shown in Table 2.

[0141] Comparative Example 1

[0142] In Example 1, instead of applying 0.1 g of the translucent liquid dispersion on 100% cotton fibers of 5 cm in length and 10 cm in width, 0.1 g of a 5% adipic acid dihydrazide aqueous solution was applied to 100% cotton fibers of 5 cm in length and 10 cm in width. The same operation as in Example 1 was carried out to prepare a deodorizing structure, and its aldehyde capture rate was measured.

[0143] Comparative Example 2

[0144] In Example 1, instead of applying 0.1 g of the translucent liquid dispersion on 100% cotton fibers of 5 cm in length and 10 cm in width, 0.2 g of a 5% adipic acid dihydrazide aqueous solution was applied on 100% cotton fibers of 5 cm in length and 10 cm in width. The same operation as in Example 1 was carried out to prepare a deodorizing structure, and its aldehyde capture rate was measured.

[0145] The results of Examples 1 to 35, Reference Examples 1 to 6, and Comparative Examples 1 and 2 are shown in Table 2. As can be seen from Table 2, the deodorant of the present invention exhibits superior aldehyde capturing ability compared to conventional deodorants.

[0146] [Table 1]

[0147]

[0148] [Table 2]

[0149]

[0150] Embodiment 36

[0151] The deodorant structure obtained in Example 1 was washed once or five times according to the test method for washing durability (JIS L0217 103 method).

[0152] The acetaldehyde capture test was carried out in the same manner as in Example 1 with respect to the deodorant structure after washing once and the deodorant structure after washing five times.

[0153] Embodiment 37

[0154] A deodorizing structure was prepared in the same manner as in Example 1, except that the drying at 60° C. for 1 hour was changed to the drying at 110° C. for 40 minutes, and an acetaldehyde capturing test was conducted.

[0155] The deodorizing structure was washed once or five times according to the test method for washing durability (JIS L 0217 103 method).

[0156] The acetaldehyde capture test was carried out in the same manner as in Example 1 with respect to the deodorant structure after washing once and the deodorant structure after washing five times.

[0157] Embodiment 38

[0158] The deodorant structure obtained in Example 6 was washed once or five times according to the test method for washing durability (JIS L0217 103 method).

[0159] The acetaldehyde capture test was carried out in the same manner as in Example 1 with respect to the deodorant structure after washing once and the deodorant structure after washing five times.

[0160] Embodiment 39

[0161] A deodorizing structure was prepared in the same manner as in Example 6, except that the drying at 60° C. for 1 hour was changed to the drying at 110° C. for 40 minutes, and an acetaldehyde capturing test was conducted.

[0162] The deodorizing structure was washed once or five times according to the test method for washing durability (JIS L 0217 103 method).

[0163] The acetaldehyde capture test was carried out in the same manner as in Example 1 with respect to the deodorant structure after washing once and the deodorant structure after washing five times.

[0164] Comparative Example 3

[0165] The deodorant structure obtained in Comparative Example 1 was washed once or five times according to the test method for washing durability (JIS L0217 103 method).

[0166] The acetaldehyde capture test was carried out in the same manner as in Comparative Example 1 about the deodorant structure after washing once and the deodorant structure after washing five times.

[0167] Comparative Example 4

[0168] A deodorizing structure was prepared in the same manner as in Comparative Example 1, except that the drying at 60° C. for 1 hour was changed to the drying at 110° C. for 40 minutes, and an acetaldehyde capturing test was conducted.

[0169] The deodorizing structure was washed once or five times according to the test method for washing durability (JIS L 0217 103 method).

[0170] The acetaldehyde capture test was carried out in the same manner as in Comparative Example 1 about the deodorant structure after washing once and the deodorant structure after washing five times.

[0171] The results of Examples 36 to 39 and Comparative Examples 3 to 4 are shown in Table 3. As can be seen from Table 3, the deodorant of the present invention exhibits superior water resistance compared to conventional deodorants.

[0172] [Table 3]

[0173]

[0174] It should be noted that the entire contents of the specification, claims, drawings, and abstract 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 cited herein and introduced as a disclosure of the specification of the present invention.

[0175] Industrial Applicability

[0176] The aminooxyalkyl group-containing polysiloxane of the present invention captures aldehydes rapidly and continuously, thereby reducing odors derived from aldehydes and improving the living environment of people.

Claims

1. An aminooxyalkyl-containing polysiloxane having a structural unit represented by the following general formula (1): In formula (1), R each 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 Q each independently represents a group selected from the group consisting of -CH2-, -CH2CH2-, and -CH2-Ra-CH2-, wherein: Ra represents an alkylene group having 1 to 18 carbon atoms, and two or more non-adjacent -CH2- in the alkylene group are each 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 the hydrogen atoms of the alkylene group are optionally replaced by an alkyl group having 1 to 3 carbon atoms, M represents an aluminum atom, a silicon atom or a titanium atom, and n represents an integer of 1 or 2, and when M is an aluminum atom, n is 1, and when M is a silicon atom or a titanium atom, n is 2.

2. The aminooxyalkyl-containing polysiloxane according to claim 1, wherein Each R is independently methyl, methoxy, ethoxy, propoxy, isopropoxy or hydroxy.

3. The aminooxyalkyl-containing polysiloxane according to claim 1, wherein M is a silicon atom, and n is 2. The aminooxyalkyl group-containing polysiloxane according to claim 1 , which has a volume median particle size of 300 nm or less.

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

6. A method for producing an aminooxyalkyl-containing polysiloxane according to claim 1, characterized in that: The compound represented by the following general formula (2) and the compound represented by the following general formula (3) are copolymerized in the presence of water, In formula (2), R 1 Each independently represents an alkyl group having 1 to 4 carbon atoms, and R 2 Each independently represents an alkoxy group having 1 to 4 carbon atoms, Q has the same meaning as described above, and m represents an integer of 0 to 2. R 1 m' -Si-R 2 4-m' (3) In formula (3), R 1 and R 2 represents the same meaning as above, and m' represents an integer of 0-3.

7. The method for producing an aminooxyalkyl-containing polysiloxane according to claim 5, wherein Regarding the ratio of the total molar amount of the compound represented by the general formula (4) and the compound represented by the general formula (5) to the molar amount of the compound represented by the general formula (2) (molar ratio), 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 relative to 1 mole of the compound represented by the general formula (2).

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

9. A deodorant comprising the aminooxyalkyl group-containing polysiloxane according to claim 1.

10. A deodorizing structure, characterized in that: The aminooxyalkyl-containing polysiloxane according to claim 1 is supported on a substrate.

11. The deodorant structure according to claim 10, wherein The substrate is a fiber-like object, a sheet-like object, a bead-like object, a sponge-like object or a plate-like object.

12. A method for removing aldehydes, characterized in that: The deodorizing structure according to claim 10 is brought into contact with an aldehyde-containing gas.

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