JPH0129577B2 - - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION Field of the Invention The present invention relates to deodorizing fragrances. More specifically, the present invention relates to a deodorizing fragrance that eliminates bad or unpleasant odors such as human body odor, animal odor, and animal visceral odor, or masks house odor and hospital odor, and actively deodorizes it.

[Conventional technology]

Conventionally, glyoxal, for example, has been widely used as a remover for bad or unpleasant odors, but it has not been able to achieve sufficient effects. In other words, in order to maintain its stability, glyoxal is often used in an acidic environment, especially around PH2, and its acidity corrodes mortar, concrete, and metals, so they are not used in construction materials. It could not be used in an environment where
In addition, the container required some ingenuity, and there were also restrictions on how it could be mixed with other fragrances.

[Purpose of the invention]

Therefore, the present inventors conducted intensive research to develop a drug that does not have the above-mentioned drawbacks and has an excellent deodorant and aromatic effect, and as a result, it was found that saturated monoterpene hydroperoxide has an extremely excellent deodorant and aromatic effect. This discovery led to the present invention.

That is, an object of the present invention is to provide a novel deodorant fragrance containing a saturated monoterpene hydroperoxide as an active ingredient.

[Structure and effects of the invention]

The present invention has the following main configuration (1) and embodiment configurations (2) to (4).

(1) A deodorizing fragrance containing saturated monoterpene hydroperoxide as an active ingredient.

(2) The saturated monoterpene hydroperoxide is one or more bicyclic monoterpene hydroperoxides selected from pinane hydroperoxide, thuyan hydroperoxide, callan hydroperoxide, and bornane hydroperoxide. deodorant air freshener.

(3) The deodorizing fragrance according to item 1, wherein the saturated monoterpene hydroperoxide is one or more monoterpene hydroperoxides selected from paramenthane hydroperoxide and metamenthane hydroperoxide.

(4) The saturated monoterpene hydroperoxide is a mixture of two or more types selected from both bicyclic monoterpene hydroperoxides and monocyclic monoterpene hydroperoxides. Deodorizing fragrance.

Specific examples of saturated monoterpene hydroperoxides for use in the present invention include bicyclic compounds such as pinane hydroperoxide, thuyan hydroperoxide, callan hydroperoxide, and bornane hydroperoxide, and paramenthane hydroperoxide, metamenthane hydroperoxide, etc. Examples include monocyclic compounds such as hydroperoxides, and mixtures of any two or more thereof.

Hydroperoxides are generally produced by passing air or oxygen directly through pinane, tuyan, calan, bornane, paramenthane, metamenthane, mixtures thereof, or solutions thereof in the presence of metals such as nickel, iron, and copper. It will be done. The reaction rate can be tracked by iodometry, but it is not necessary to complete the reaction, but rather to keep the peroxide production rate below about 60%, preferably from 10 to 50%.
% is practical from the viewpoint of energy consumption. It is also possible to separate high-purity hydroperoxides if necessary, but even a mixture with raw materials can sufficiently satisfy the purpose as a deodorizing and aromatic agent. In this case, the raw saturated terpene is also useful as a peroxide dilution stabilizer.

The present deodorant fragrance can also be blended as a base with other physicochemical deodorants or other fragrances. The other physicochemical deodorant or the fragrance is not limited to any particular one. Physicochemical deodorants include active liquids, other fragrance absorbers, and dialdehydes. The fragrance may be either natural or synthetic. As a diluent for the deodorant fragrance of the present invention, organic solvents such as acetals, alcohols, or hydrous alcohols can be used. The present invention will be explained below with reference to Examples.

Example 1 0.5 part of nickel powder was added to 100 parts of pinane obtained by catalytic hydrogenation of α-pinene, and the mixture was heated at about 100°C.
After heating and raising the temperature, air was bubbled through the mixture while stirring.
The reaction is stopped when the amount of pinane hydroperoxide produced reaches 26% as determined by iodometry. A mixed liquid having a calm, mushy aroma was obtained, and this mixture was used as it was as a deodorizing fragrance.

The deodorizing effect of this mixture is as follows.

Using the pinane hydroperoxide (hereinafter referred to as sample) in Example 1, the removal effect of the odors described below was examined by sensory tests and instrumental tests. The target odors are as follows.

Garbage and organic dirt containing acid, hydrogen sulfide, and ammonia were subjected to sensory tests, and equipment tests were carried out.

(1) Test method Food waste and organic dirt: Put 100 to 200 g of food waste with a moisture content of approximately 95% and organic dirt into a glass container, and mix it with a mixture consisting of 45.1% pinan and 54.9% sample. 25 of
5 ml of % ethanol solution was evenly sprinkled on the container, the container was sealed tightly and allowed to stand. Thereafter, an odor sensory test was conducted over time.

Butyric acid: Dilute butyric acid as an odor source with nitrogen gas to an odor strength of approximately 3 in a Tedlar bag to obtain the original odor. A glass fiber paper impregnated with the sample is connected to this bag, and the odor after passing through the paper is inspected by a sensory test. did.

Hydrogen sulfide and ammonia: Create the original odor by diluting hydrogen sulfide or ammonia with air in a 60 Tedlar bag,
Glass fiber paper impregnated with the sample was connected to this bag, and the odor after passing through the paper was analyzed by gas chromatography for hydrogen sulfide and colorimetric analysis for ammonia using indophenol.

(2) Results It is as follows.

Food waste and organic dirt When the sample was not added, the putrid odor turned black significantly after 10 days, but with the sample additive, no putrid odor other than the sample odor was observed, and there was a slight Only browning was observed.

In the case of organic soil without the addition of the sample, it turned green with a marked putrid odor after 10 days, but with the addition of the sample, there was no putrid odor other than the sample odor, and there was no change in color tone.

In other words, the sample showed not only a deodorizing effect but also a remarkable masking effect against these sources of bad odors.

Butyric acid After passing through the paper, no butyric acid odor was detected other than the sample odor.

Hydrogen sulfate and ammonia The average removal rate for hydrogen sulfide was approximately 30%, but in the sensory test, no hydrogen sulfide odor could be detected in addition to the sample odor. Regarding ammonia, the average removal rate was extremely high at 95%, and in the sensory test, no ammonia odor was observed other than a slight sample odor.

That is, the sample has both deodorizing and masking effects on these odors.

Example 2 100 parts of pinane obtained by catalytic hydrogenation of β-pinene was operated in the same manner as in Example 1 to obtain a 25% solution of the corresponding hydroperoxide. The deodorizing effect of this mixture was tested in the same manner as in Example 1. Approximately the same effects as the mixture of Example 1 were observed with respect to food waste, organic dirt, lactic acid, hydrogen sulfide, and ammonia.

Example 3 Add 0.1 part of nickel powder to 20 parts of l-calan,
After heating to about 100°C, the mixture was aerated with stirring. When the amount of hydroperoxide produced reached 15%, the reaction was stopped, and the callan was distilled off under reduced pressure to give a hydroperoxide content of 30%. The thus obtained liquid mixture was used as a deodorizing fragrance as it was, and an effect substantially equivalent to that of the mixture of Example 1 was observed.

Example 4 0.2 parts of iron powder was added to 20 parts of Tsuyang, and the mixture was stirred and heated under ventilation to react at about 90°C. The reaction was stopped when the amount of hydroperoxide reached 20%.
Four parts of citronellol was added to the thus obtained mixture and used as a deodorizing aromatic agent, and an effect substantially equivalent to that of the mixture of Example 1 was observed.

Example 5 20 parts of bornane was dissolved in 50 parts of cyclohexane,
0.04 part of cobalt powder was added, and the mixture was heated with stirring and ventilation, and the reaction was continued at 80°C. The reaction was stopped when the amount of hydroperoxide produced reached 10%. Two parts of trans-2-hexenol was added to the mixture thus obtained and used as a deodorizing aromatic agent, and an effect substantially equivalent to that of the mixture of Example 1 was observed.

Example 6 Add 0.4 parts of nickel powder to 40 parts of paramenthane,
The mixture was heated to about 80°C and aerated with stirring. The reaction was stopped when the amount of hydroperoxide produced was adequate to 22%. The thus obtained liquid mixture was used as it was as a deodorizing aromatic agent, and almost the same effect as in Example 1 was observed.

Example 7 Add 0.4 parts of nickel powder to 40 parts of metamenthan,
The mixture was heated to about 70°C and aerated with stirring. The reaction was stopped when the amount of hydroperoxide produced reached 20%. A small amount of rose oil was added to the mixture thus obtained and used as a deodorizing aromatic agent, and almost the same effect as in Example 1 was observed.

Example 8 0.3 parts of nickel powder was added to a mixed solution consisting of 20 parts of paramenthane and 10 parts of metamenthane, and the mixture was heated to about 80°C and aerated with stirring. The reaction was stopped when the amount of hydroperoxide produced reached 20%. A small amount of orange blossom oil was added to the thus obtained mixture and used as a deodorizing fragrance, and almost the same effect as in Example 1 was observed.

Claims (1)

[Claims] 1. A deodorant fragrance containing a saturated monoterpene hydroperoxide as an active ingredient. 2. Claim 1, wherein the saturated monoterpene hydroperoxide is one or more bicyclic monoterpene hydroperoxides selected from pinane hydroperoxide, thuyan hydroperoxide, callan hydroperoxide, and bornane hydroperoxide. The deodorant air freshener listed. 3. The deodorant fragrance according to claim 1, wherein the saturated monoterpene hydroperoxide is one or more monocyclic monoterpene hydroperoxides selected from paramenthane hydroperoxide and metamenthane hydroperoxide. 4. Claim 1, wherein the saturated monoterpene hydroperoxide is a mixture of two or more selected from each of bicyclic monoterpene hydroperoxides and monocyclic monoterpene hydroperoxides. deodorant air freshener.