JPH0956800A - Deodorant and deodorizing method - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a deodorant which can effectively remove aldehyde, etc., which are a bad-small substance, and a deodorizing method with the said deodorant. SOLUTION: The deodorant is a deodorant containing heterocyclic compounds, in which amino groups of first class are bonded with aromatic heterorings having at least one nitrogen atom as a constituent element. The heterocyclic compounds are preferably acid salts. An example of deodorizing methods with the above deodorant is a method in which a bad-smell substance, mainly of aldehyde, is deodorized by making it touch the said deodorant.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a deodorant, and more particularly to a deodorant capable of removing an odor which is a malodorous substance, and
The present invention relates to a deodorizing method using the deodorant.

[0002]

2. Description of the Related Art Among many malodorous substances, aldehydes such as acetaldehyde are one of the substances that are difficult to remove only by physical adsorption by a porous material such as activated carbon. On the other hand, there is a high level of social awareness regarding the elimination of tobacco and exhaust gas odors, which are the main causes of aldehyde odors. For this reason,
There is a demand for a deodorant having a high-performance aldehyde removing ability. As such a deodorant, for example, a deodorant containing an acid salt of sulfanilamide (Japanese Patent Laid-Open No. 6-2259) is disclosed.
No. 27) is known.

[0003]

[Problems to be Solved] The aldehyde removing ability of the above deodorant involves an unshared electron pair (not in --NH ₃ ⁺ ) possessed by nitrogen in the amino group (--NH ₂ ) of sulfanilamide, It is considered that the more NH ₂ is, the more effective it is. However, when sulfanilamide is used as an acidic salt,
NH ₂ becomes --NH ₃ ⁺ , and --NH ₂ amount decreases. Therefore, it is necessary to balance the ratio of the --NH ₂ amount and the --NH ₃ ⁺ amount by controlling the amount of acid for forming an acidic salt or the basicity of sulfanilamide.

The present invention is intended to provide a deodorant capable of effectively removing a malodorous substance, particularly an aldehyde, and a deodorizing method using the deodorant.

[0005]

The deodorant of the present invention is a deodorant containing a heterocyclic compound, wherein the heterocyclic compound is a heterocyclic ring having aromaticity having at least one nitrogen atom as a constituent element. It is characterized in that a primary amino group is bonded.

The deodorizing method of the present invention is a method for deodorizing a malodorous substance by bringing it into contact with a heterocyclic compound to remove the malodorous substance, wherein the heterocyclic compound has at least one nitrogen atom. It is characterized in that a primary amino group is bonded to a heterocycle having aromaticity as a constituent element.

Next, the operation of the present invention will be described. The deodorant of the present invention contains a heterocyclic compound. In this heterocyclic compound, a primary amino group is bonded to a heterocyclic ring containing a nitrogen atom as a constituent element and having aromaticity.
Therefore, according to the deodorant of the present invention, the malodorous substance can be efficiently removed. It is especially effective in removing aldehydes. Although the details of the reaction are not clear, the following reactions are presumed as an example.

The above-mentioned heterocyclic compound contains a primary amino group. The nitrogen atom in the amino group has an unshared electron pair. This unshared electron pair initiates a nucleophilic addition reaction on the carbonyl carbon of the aldehyde. Therefore, the presence of amino groups with enhanced nucleophilicity facilitates the initiation of the reaction. As a result, the aldehyde is dehydrated and condensed with the amino group. The two molecules of aldehyde are dehydrated and condensed between the methine group and amino group of the heterocycle to form a condensed pyridine ring, whereby the aldehyde is fixed and effective deodorization is possible. This action is exhibited by the primary amino group.

The nitrogen atom in the heterocycle acts on the nitrogen atom in the amino group to promote the unshared electron pair of the nitrogen atom in the amino group to initiate the nucleophilic addition reaction. it is conceivable that. In addition, even when an aromatic heterocycle is used as an acid salt, the unshared electron pair on the nitrogen atom in the amino group does not disappear. Therefore, as described above, the deodorizing ability of the nitrogen atom in the amino group can be maximized.

Next, according to the deodorizing method of the present invention, since the above-mentioned heterocyclic compound is used, a malodorous substance can be reacted and converted into a different substance to be removed, and in particular, aldehyde can be effectively removed. be able to.

[0011]

BEST MODE FOR CARRYING OUT THE INVENTION In the deodorant and deodorizing method of the present invention, the heterocyclic compound has at least one nitrogen atom as a constituent element, and a primary amino group is bonded to a heterocyclic ring having aromaticity. It is a thing. A heterocyclic compound is
Among the organic compounds having a cyclic structure, the elements constituting the ring include not only carbon atoms but also oxygen, sulfur, nitrogen, phosphorus, arsenic, etc. in the ring.

The heterocyclic compound of the present invention has at least one nitrogen as an element constituting the above ring (heterocycle). Further, the above heterocycle has aromaticity. The heterocycle having aromaticity is a heterocycle having physical and chemical properties peculiar to aromatic compounds.
For example, in terms of chemical properties, the ring is stable, the addition reaction is unlikely to occur, and the substitution reaction is likely to occur. Also,
The ring is stable by having 4n + 2 π electrons in the ring. Thus, due to the stability of the ring,
A malodorous substance can be removed stably.

The aromatic heterocycle (hereinafter referred to as aromatic heterocycle) contains at least one nitrogen atom as a constituent element. That is, at least one of the ring atoms of the aromatic heterocycle is a nitrogen atom. Examples of such aromatic heterocycles include, but are not limited to, pyridine, pyrrole, isoxazole, and oxazole. The aromatic heterocycle may be monocyclic or polycyclic. Further, the number of elements forming the heterocycle is not limited.

The aromatic heterocycle is preferably a basic heterocycle. An acid is one that acts as a catalyst in a reaction with a malodorous substance such as an aldehyde to improve the deodorizing property. If it is a basic heterocycle, it can form a salt (acid salt) with this acid to improve the deodorizing property.

A primary amino group (--NH ₂ ) is bonded to the aromatic heterocycle. The bonding position may be any position on the aromatic heterocycle. Further, the primary amino group may be directly bonded to the heterocycle, or may be bonded to the heterocycle via another atom or group R as illustrated in "Chemical Formula 1". The other atom or group R may be any atom or group. In addition, the primary amino group may have a primary amino group bonded to the ring having N in the polycyclic heterocycle as illustrated in "Chemical Formula 2", or "Chemical Formula 3"
As illustrated in, a primary amino group may be bonded to the ring having no N.

[0016]

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[0017]

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[0018]

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Among the above, the binding position of the primary amino group is preferably a position at which the electron withdrawing effect of the nitrogen atom constituting the aromatic heterocycle is avoided. This is because the deodorizing action of amino groups may be reduced due to the electron withdrawing effect. For example, in the case of a 6-membered ring, it is preferably in the meta position with respect to the nitrogen atom which is one of the ring atoms.

Examples of the heterocyclic compound in which the amino group is bonded to the aromatic heterocycle include, but are not limited to, aminopyridine or its derivative, aminoisoxazole or its derivative, aminopyrrole or its derivative, and the like. . Among these, for example, 3-aminopyridine or its derivative, 5-aminopyridine or its derivative, 3-aminoisoxazole or its derivative, 3-aminopyrrole or its derivative, 4-aminopyrrole or its derivative are preferable. . The reason for this is that these have an amino group at a position that avoids the electron-withdrawing effect of the nitrogen that constitutes the heterocycle, so the nucleophilicity of the nitrogen in the amino group is maintained, and the reactivity with malodorous substances such as aldehydes is improved. Because.

Further, the aromatic heterocycle preferably has an electron-donating functional group for enhancing the nucleophilicity of the amino group bonded as its side chain. Such functional groups include, for example, a methyl group (CH _3), alkyl groups represented by a methoxy group (-OCH _3), and the like alkoxy groups.

Further, at least one of the carbon atoms constituting the ring to which the amino group is bound is adjacent to a methine group (CH).
It is preferred that This is because when an odor that is a malodorous substance reacts with a heterocyclic compound, aldehyde (-CH
This is because the hydrogen and oxygen in O) react with the hydrogen of the methine group to cause dehydration condensation and improve the aldehyde removal performance.

The heterocyclic compound is preferably an acid salt. The reason is that the acid activates the aldehyde when the amino group reacts with the aldehyde and acts as a catalyst for the dehydration condensation reaction between the amino group and the aldehyde. Therefore, the reactivity with the aldehyde is further improved. In addition, the presence of acid can also remove the basic odor at the same time.

Further, the nitrogen ionized by making the heterocyclic compound an acidic salt is only the nitrogen in the heterocycle,
The nitrogen in the amino group is not ionized. for that reason,
There is no reduction in the aldehyde removal ability due to the reduction of unshared electron pairs of nitrogen in the amino group. Therefore, the aldehyde removal performance is further improved by effectively activating the nucleophilicity of the amino group, which is a primary amine, and by activating the aldehyde with an acid.

Examples of the acid salt of the above heterocyclic compound include phosphate of the heterocyclic compound, sulfate of the heterocyclic compound,
Heterocyclic compound hydrochlorides include, but are not limited to.

The deodorant is preferably used by being carried on a carrier. This is because the carrier has a large specific surface area so that aldehyde molecules can be physically adsorbed, the concentration of aldehyde near the deodorant present on the carrier surface can be increased, and the reaction with the aldehyde can be efficiently performed. . As the carrier, for example, a general porous material such as activated carbon, activated carbon fiber, porous clay mineral, or porous silica can be used. The form of the carrier may be honeycomb, granule, sheet or the like, but is not particularly limited.

The amount of the deodorant loaded on the carrier is 0.1 when the total weight of the deodorant and the carrier is 100% by weight.
It is preferably ˜20% by weight. If the amount is less than 0.1% by weight, even if physical adsorption of the aldehyde occurs, the deodorizing agent is small in amount, and therefore the aldehyde removing ability may not be enhanced. On the other hand, if it exceeds 20% by weight, the surface of the carrier is covered with the deodorant, so that the specific surface area of the carrier becomes small and the effect of physical adsorption may be difficult to be obtained. The above deodorant is not loaded on the carrier,
It can be used alone.

In the deodorizing method of the present invention, the method of contacting the above deodorant with an aldehyde is, for example,
On the carrier having the deodorant supported on the carrier as described above,
Alternatively, there is a method of bringing an aldehyde-containing gas into contact with a single deodorant.

[0029]

【Example】

Example 1 A deodorant according to an example of the present invention will be described with reference to Table 1. The deodorant of this example contains a phosphoric acid salt of 5-amino-2-methoxypyridine shown in "Chemical Formula 4" as an acidic salt of a heterocyclic compound. This phosphate is impregnated in activated carbon fiber paper. The supported amount of the heterocyclic compound is the total weight of the heterocyclic compound and the activated carbon fiber paper 1
It is 2.5% by weight with respect to 00% by weight.

[0030]

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In evaluating the deodorizing performance of the above deodorant, first, 0.1 g of the above deodorant (heterocyclic compound + activated carbon fiber paper) was put in a gas impermeable bag. On the other hand, the acetaldehyde aqueous solution as a malodor source was heated and vaporized. 5 liters (room temperature) of this vaporized mixture of gas and air as an offensive odor was placed in the bag containing the deodorant and sealed. At this time, four kinds of different gas concentrations were prepared by changing the amount of acetaldehyde aqueous solution.

The bag was allowed to stand in a room, and 24 hours later, the concentration of acetaldehyde gas remaining in the bag was measured by gas chromatography. The adsorbed amount of acetaldehyde was determined from the results and an adsorption isotherm was created. Based on the adsorption isotherm, the amount of adsorption when the residual concentration was 1, 10, 100 ppm was obtained, and the deodorizing performance of the deodorant was evaluated. The results are shown in Table 1.

Example 2 In the deodorant of this example, the phosphoric acid salt of 3-amino-5-methylisoxazole shown in Chemical formula 5 was used as the acidic salt of the heterocyclic compound. Others are the same as the deodorant of Example 1.
With respect to the deodorant of this example, the deodorizing performance was evaluated in the same manner as in Example 1 and shown in Table 1.

[0034]

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Comparative Example 1 The deodorant of this comparative example is obtained by impregnating activated carbon fiber with 2.5% by weight of an acidic salt of an aromatic amino acid. The acidic salt of the aromatic amino acid is a phosphate of paraaminobenzoic acid. Others are the same as the deodorant of Example 1. With respect to the deodorant of this example, the deodorizing performance was evaluated in the same manner as in Example 1 and shown in Table 1.

Comparative Example 2 The deodorant of this Comparative Example was an acidic salt of an aromatic amino acid.
The phosphate of sulfanilamide was used. The others are the same as in Comparative Example 1. Regarding the deodorant of this example, Example 1
The deodorizing performance was evaluated in the same manner as in Table 1 and shown in Table 1.

[0037]

[Table 1]

Next, the deodorants according to Examples 1 and 2 and Comparative Examples 1 and 2 will be comparatively evaluated. As is known from Table 1, the deodorants according to Examples 1 and 2 were superior in acetaldehyde removal performance to the deodorants according to Comparative Examples. Particularly, in Example 1, the removal performance was high in the low residual concentration range. In addition, in Example 2, the removal performance was relatively high in the relatively high residual concentration range. From the above, it is understood that the deodorant of the present invention can effectively remove odor which is a malodorous substance.

[0039]

According to the present invention, it is possible to provide a deodorant capable of effectively removing a malodorous substance, particularly an aldehyde, and a deodorizing method using the deodorant.

 ─────────────────────────────────────────────────── ─── Continuation of front page (72) Inventor Kazuhiro Fukumoto Aichi Prefecture, Nagakute Town, Aichi Prefecture, Nagacho, 1 1st side street, Yokoshiro Central Research Institute Co., Ltd. No. 41 Nagamichi Yokomichi 1 Toyota Central Research Institute Co., Ltd.

Claims (4)

[Claims] 1. A deodorant containing a heterocyclic compound, wherein the heterocyclic compound has a heterocyclic ring having aromaticity having at least one nitrogen atom as a constituent element and a primary amino group bonded to the heterocyclic ring. Deodorant characterized by being present. 2. The deodorant according to claim 1, wherein the heterocyclic compound is an acid salt. 3. Contacting a malodorous substance with a heterocyclic compound,
A method for deodorizing by removing the malodorous substance, wherein the heterocyclic compound has a primary amino group bonded to an aromatic heterocycle having at least one nitrogen atom as a constituent element. A deodorizing method characterized by being. 4. The deodorizing method according to claim 3, wherein the heterocyclic compound is an acid salt.