JPH0857029A - Deodorant and deodorizing method - Google Patents

Abstract

PURPOSE: To strongly deodorize a malodor such as a hydrogen sulfide odor by using one or more effective constituents of a specific compound such as N-hydroxymethylaminothanol in a deodorant for rotten odors of industrial products such as various latexes and a cutting lubricant. CONSTITUTION: One or more effective constituents of the compound expressed by the formula are used for a deodorant effective for a reducing odor, where R indicates the hydrogen atom or hydroxyl group, R<1> indicates the hydroxyl group or monovalent chemical bond R<2> indicates the hydrogen atom or monovalent chemical bond, and (n) indicates an integer of l-3. When n=1; R, R<1> =OH, and R<2> =H. When n=3; R<1> , R<2> indicate chemical bond and form S-triazine rings. N-hydroxymethylaminoethanol, hexahydro-1, 3, 5-triethyl-S-triazine, and hexahydro-1, 3, 5-tris(2-hydroxylethyl)-S-triazine are used for this compound.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention mainly relates to a deodorant for deodorizing hydrogen sulfide and the like and a deodorizing method. Specifically, the present invention relates to an industrial product such as various latexes, coating colors, cutting oils, etc., and a deodorant and a deodorant method for decomposing odor of various industrial wastes.

[0002]

BACKGROUND OF THE INVENTION When various latexes, coating colors and cutting oils rot, a bad odor is generated. The bad odor due to putrefaction is usually a mixture of various odors, and the main components of the odor are hydrogen sulfide, ammonia, and methyl sulfide, but the hydrogen sulfide odor is strongly felt in the various industrial products. The olfactory threshold of hydrogen sulfide is 0.0047 ppm (deodorant / deodorant / antibacterial business, page 17, Table 2 (1992 1
(October 30th), published by CMC Co., Ltd.). When such a bad odor as hydrogen sulfide is generated, it causes a number of problems in environmental hygiene, and when it occurs indoors such as in a factory, it reduces the work efficiency of the worker and further adversely affects the health of the worker. May be affected.

Generally, as a method for eliminating a malodor, 1) masking is a method in which a strong aroma is emitted so that the malodor is not sensed, 2) a chemical reaction, a malodorous substance is odorized by a chemical reaction such as oxidation or reduction. There is a method of changing to a non-existent substance, 3) Adsorption, a method of adsorbing a bad odor using activated carbon, etc., 4) Others, etc.

The alkaline cleaning method is used in combination with the water cleaning method for deodorizing and deodorizing the hydrogen sulfide odor. The alkaline cleaning method is a method of absorbing hydrogen sulfide into sodium hydroxide or sodium carbonate, and is said to be based on the following chemical reaction (latest deodorant and deodorant technology, page 7 (1)
January 989), published by Japan Society of Industrial Technology). H ₂ S + NaOH → NaSH + H ₂ OH ₂ S + Na ₂ CO ₃ → NaSH + NaHCO ₃ However, since the above target system is alkaline, the deodorizing effect by sodium hydroxide was hardly obtained (Examples, Comparative Examples See D).

Further, on page 21 of the same book, there is a method of deodorizing the odor of hydrogen sulfide with formalin, which proceeds as the following reaction.

[0006]

Embedded image

Under the test conditions of the present invention, almost no deodorizing effect was obtained by this method as well (see Example section, Comparative Example C). In addition, deodorant by various fungicides (resorcinols, hexachlorophenes, dichlorophenes, cresols, etc.) is used to kill the bacteria that cause the decay of various industrial products and stop the decay to eliminate the odor. prevent. In short, sterilization suppresses the generation of a new spoiled odor, and does not eliminate the spoiled odor that has already occurred.

Further, an oxidizing agent such as sodium hypochlorite is generally used as a deodorant for reducing odor such as hydrogen sulfide. That is, it is a method of chemically deodorizing by a redox reaction. In this method, the oxidant was reduced and the oxidant was consumed, the deodorant was effective only for a short time, and the addition of the oxidant was required. Further, excessive addition causes a new chlorine odor to be generated, which is disadvantageous in that it is difficult to handle.

The methods used up to now require a large amount of chemicals to deodorize the smell of hydrogen sulfide, etc., and since the chemicals are consumed along with the deodorization, they are effective only for a short time and for a long time. It was necessary to add more chemicals to deodorize. This time, the present inventors have found that the compound represented by the formula (I) deodorizes putrid odors such as hydrogen sulfide odor in a short time so that it can be said to be instantaneous, and the effect lasts for a long time. With this in mind, the present invention has been completed.

[0010]

Thus, according to the present invention, the general formula (I):

[0011]

[Chemical 3]

(Wherein R is a hydrogen atom or a hydroxyl group; R ¹ is a hydroxyl group or a monovalent chemical bond; R ² is a hydrogen atom or a monovalent chemical bond; n is an integer of 1 to 3, provided that
When n = 1, R, R ¹ = OH, R ² = H, and n = 3
At this time, R ¹ and R ² both represent a chemical bond to form an S-triazine ring. The deodorant which contains one or more types of compounds represented by these as an active ingredient is provided.

2-hydroxymethylamiethanol, hexahydro-1,3,5-triethyl-S-triazine and hexahydro-1,3.5-tris (2-) as the compound of formula (I) which is the active ingredient of the present invention. Hydroxyethyl) -S-triazine and the like. These are all known antibacterial agents. However, it is not known to have a deodorant ability.

(1) When the active ingredient of the present invention is used as a deodorant When the active ingredient of the present invention is used in a target system for the purpose of deodorizing,
The amount of compound added is 250 to 7,000 p with respect to the deodorant object
It is pm, preferably 500 to 5000 ppm, and is added directly to the target system as soon as it feels a rotten odor. Immediately after the addition, a deodorizing effect appears, and this effect lasts for a long time (it has been confirmed in Examples that it lasts for 1 week). (2) When the active ingredient of the present invention is used as an antibacterial agent Since the active ingredient of the present invention has a mild action on bacteria, it is usually used as an antibacterial agent. When the active ingredient of the present invention is used in a target system for antibacterial purposes, the addition amount is 500 to 3
It has an active ingredient concentration of 000 ppm, and is added directly to the liquid for cutting oil, or to the circulation line when new cutting oil is replenished, and to the mixing tank for coating color. About 24 hours after the addition, an antibacterial effect appears (see Example, Table 3).

As described above, the amount added and the time of effect development are completely different between the case of using for deodorizing purpose and the case of using for antibacterial purpose. Therefore, like the mechanism of deodorant action of the above-mentioned resorcinols and other germicides, it is completely different from the mechanism of action of suppressing the generation of newly spoiled odor by killing the bacterium that causes the spoilage of the target system. . For the purpose of deodorizing, when the active ingredient of the present invention is used in a target system, the deodorizing effect appears immediately after addition, but at this point, the antibacterial effect of the active ingredient of the present invention has not yet appeared (Example section,
See Table 3).

Therefore, the deodorizing effect of the active ingredient of the present invention is not due to the antibacterial effect of the active ingredient,
It can be said that this is a completely different effect. The active ingredient of this invention is
It is a substance having the effect of lowering the redox potential by its addition, and is considered to be a reducing agent rather than an oxidizing agent. It is a surprising fact that such a substance can deodorize a putrid odor such as hydrogen sulfide odor which is a reducing odor substance. Furthermore, when cutting oil, latex, etc. rot, the color of the liquid turns dark, so there was no alternative but to discard the rot and replace it with a new one. As it recovers, it can be used continuously. This deodorizing effect is not due to the addition of alkali, nor is it due to formalin generated by the decomposition of the active ingredient of the present invention (see Examples, Table 1).

The deodorizing mechanism of the active ingredient of the present invention is unknown, and is probably a kind of acid-alkali reaction.
The deodorizing effect is immediate and long-lasting, there is no need to add a drug again, and the target system for deodorizing is not contaminated.
It is a very ideal deodorant. However, the active ingredient of the present invention is decomposed to generate formalin when the pH of the target system is lowered, that is, when the system tends to be acidic, and the deodorizing effect is almost lost.
Therefore, in order that the active ingredient of the present invention is not decomposed and the deodorizing effect is exhibited, it is necessary that the target system has a pH of 7.5 or more in an alkaline range.

In using the active ingredient of the present invention as a deodorant, a form which can be taken by a general deodorant, that is, the active ingredient of the present invention as it is, dissolved in a suitable solvent or a suitable solid carrier is used. It is mixed or adsorbed with and used in dosage forms such as liquids, powders and sprays. Although the content ratio of the active ingredient in the deodorant varies depending on the object of use, about 10 to 90% by weight is suitable for the liquid agent and the like, and about 0.1 to 10% by weight is suitable for the powder agent and the like. Depending on the object of use, these concentrations may be changed appropriately.

The solvent used may be water or a hydrophilic organic solvent. Examples of the hydrophilic organic solvent include amides such as dimethylformamide; glycols such as ethylene glycol, propylene glycol, diethylene glycol and dipropylene glycol; methyl cellosolve, phenyl cellosolve, diethylene glycol monomethyl ether, dipropylene glycol monomethyl ether,
Glycol ethers such as tripropylene glycol monomethyl ether; alcohols having up to 8 carbon atoms or methyl acetate, ethyl acetate, 3-methoxybutyl acetate, 2-ethoxymethyl acetate, 2
-Ethoxyethyl acetate, propylene carbonate, esters such as dimethyl glutarate and the like can be mentioned.

The amount of the deodorant of the present invention added is 250 to 7,000 ppm, preferably 500 to 7,000 ppm, relative to the object to be deodorized.
The working concentration is 5000 ppm. The deodorant of the present invention has a pH of 7.5 or more as a target system as described above, for example,
It is applied to industrial products such as various latexes, coating colors, cutting oils, etc., and industrial wastes that have a rotten odor.

As an embodiment of the present invention, the compound of the present invention is added to the object to be deodorized in an amount of 250 to 7,000 ppm,
There is provided a deodorizing method characterized in that it is added at a working concentration of preferably 500 to 5000 ppm at once or in several portions to deodorize. According to the deodorizing method using the active ingredient of the present invention, the deodorizing effect is exhibited immediately after addition, and the deodorizing effect lasts for a long time.

[0022]

【Example】

Test Example 1 [Test for confirming deodorizing effect of hydrogen sulfide odor] (Test method) A 100 ppm S ² -solution (pH 7.1) is prepared and dispensed in 100 ml portions into a screw bottle. Each reagent agent was added here, and an odor sensor test (using "Portable odor sensor XP-329" manufactured by New Cosmos Electric Co., Ltd.) and a sensory test were conducted at each concentration.
For sodium hydroxide (reagent D), the pH was adjusted to 8,8.5,9 and the same test was conducted. Table 1 shows the test results.

[0023]

[Table 1]

Reagent A: 2-hydroxymethylaminoethanol Reagent B: Hexahydro-1,3,5-tris (2-
Hydroxyethyl) -S-triazine Reagent C: Formaldehyde Reagent D: Sodium hydroxide Test Example 2 [Confirmation test for persistent deodorant effect of hydrogen sulfide odor] (Test method) 100 ppm S ² -solution (pH 7. Prepare 1) and dispense 100 ml aliquots into screw bottles. Hexahydro-1,3,5-triethyl-S-triazine was added here at 3000 ppm and 5000 ppm each, and after a lapse of a predetermined time, an odor sensor test ("Portable odor sensor XP-32 manufactured by New Cosmos Electric Co., Ltd."
9 ”use) and a sensory test. The test results are shown in Table 2.

[0025]

[Table 2]

Test Example 3 Effect on Spoiled Cutting Oil After being used for a long period of time and left at room temperature for 2 days, 50 g of emulsion type cutting oil having a decaying odor including hydrogen sulfide odor and a black discoloration was added in a volume of 100 ml. Dispensed into a glass screw tube. A reagent agent was added to each concentration to measure the odor sensory test, whether or not the black discoloration was improved to return to a white emulsion and the viable cell count. Table 3 shows the results.

The following reagents were used as test reagents. E: 5-Chloro-2-methyl-3-isothiazolone MgCl ₂ salt 11.3 parts by weight 2-Methyl-3-isothiazolone MgCl ₂ salt 3.6 parts by weight Water 85.1 parts by weight Composition comprising the above formulation F: Glutaraldehyde 50% aqueous solution G : 2-bromo-2-nitro-1,3-propanediol

[0028]

[Table 3]

Odor +++: Strong rotten odor Black discoloration +++: No change ++: Perishable odor ++: Improvement in color but black discoloration +: Weak rotten odor +: Slight black discoloration −: No rotten odor -: The black discoloration disappears and a white emulsion is obtained.

Test Example 4 Effect on Spoiled Latex 50 g of SBR latex (pH 8.3) having a spoiled smell containing hydrogen sulfide odor due to being stored in a long-term storage tank
Each was dispensed into a 100 ml glass screw tube. Reagents were added to each concentration to measure the odor sensory test and the viable cell count.

[0031]

[Table 4]

[0032]

EFFECTS OF THE INVENTION The deodorant of the present invention deodorizes the putrid odor mainly of the hydrogen sulfide of the target system, exhibits a remarkable deodorant effect immediately after addition, and this effect lasts for a long time. Moreover, it is not necessary to add a chemical again, and the deodorant target system is not contaminated.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification number Office reference number FI technical display location C07D 251/04 C10N 30:00 G 40:22

Claims (9)

[Claims] 1. A compound represented by the general formula (I): (In the formula, R is a hydrogen atom or a hydroxyl group; R ¹ is a hydroxyl group or a monovalent chemical bond; R ² is a hydrogen atom or 1
Valent chemical bond; n is an integer of 1 to 3, provided that when n = 1, R, R ¹ ═OH and R ² ═H, and when n = 3, R
¹ and R ² both represent a chemical bond and form an S-triazine ring. ) A deodorant comprising one or more compounds represented by the formula (1) as an active ingredient. 2. A compound according to claim 1, wherein the compound of formula (I) is 2-hydroxylmethylaminoethanol. 3. The compound of formula (I) is hexahydro-
The compound according to claim 1, which is 1,3,5-triethyl-S-triazine. 4. The compound of formula (I) is hexahydro-
The compound according to claim 1, which is 1,3,5-tris (2-hydroxyethyl) -S-triazine. 5. The deodorant according to claim 1, wherein the target system is a latex having a pH of 7.5 or more and having a putrid odor, a coating color and a cutting oil. 6. The deodorant according to claim 5, wherein the putrid odor is a hydrogen sulfide odor. 7. A rotten odor, characterized in that one or more compounds of the formula (I) are added to a target system so as to be 250 to 7,000 ppm with respect to the target substance to be deodorized. Deodorizing method. 8. The deodorizing method according to claim 7, wherein the target system is a latex having a pH of 7.5 or more and having a rancid odor, a coating color and a cutting oil. 9. The deodorizing method according to claim 8, wherein the putrid odor is a hydrogen sulfide odor.