JP5339734B2 - Odor control agent - Google Patents

Description

  The present invention relates to a malodor control agent that suppresses malodor generated by microorganisms.

In general, malodorous odors generated from the drains of household kitchens, bathrooms, and other sewage are decomposed and metabolized by proteins such as Pseudomonas, known as spoilage bacteria, attached to the drains, etc., and then proliferating. It is known that this is caused by volatile thiols, amines, and the like (Non-Patent Document 1).
In order to suppress the generation of bad odors derived from these microorganisms, physical microorganism removal with a general cleaning agent and sterilization with a disinfectant are carried out, but these microorganisms form a biofilm that causes slimming. In general, it is resistant to stresses such as cleaning removal, chemicals, and heat, so that the usual odor and sterilization methods often cannot sufficiently exert the malodor control effect.
Alkyl glycosides are known to have the effect of suppressing and removing these biofilms (Patent Document 1).
However, it is not known what components have an effect of suppressing malodor derived from microorganisms.
JP 2006-347941 A "Biofilm" written by Hisao Morisaki, published by Science Forum, 1998, 119 pages

  Therefore, an object of the present invention is to provide a microorganism-derived malodor control agent that is highly safe and can be widely used in living spaces.

The inventors of the present invention have studied compounds that have a high malodor control effect, are highly safe, and can be widely used in living spaces. As a result, the alkylgalactosides represented by the following formula (1) have similar chemical structures. As a result, the present invention was completed.
That is, the present invention provides the following formula (1):

_{R- (OA) m -O- (G} 1) n -G 2 (1)

[Wherein, R represents a linear or branched aliphatic hydrocarbon group having 6 to 18 carbon atoms which may be substituted with a substituent, and A represents a linear or branched alkylene group having 2 to 3 carbon atoms. G ¹ represents a reducing sugar residue having 5 to 6 carbon atoms, G ² represents a residue derived from galactose, m represents a number from 0 to 200, and n represents a number from 0 to 30. . ]
The odor control agent derived from microorganisms which uses the compound represented by these as an active ingredient is provided.

  ADVANTAGE OF THE INVENTION According to this invention, the bad smell derived from microorganisms can be suppressed safely, simply and efficiently in various environments in a house and industrial. Moreover, since the effect of the malodor control agent of the present invention is remarkably superior to that of alkyl glycosides having similar chemical structures, it is considered that the effect is not based on a simple biofilm suppression effect.

In the compound represented by the formula (1) used in the present invention, the linear or branched aliphatic hydrocarbon group having 6 to 18 carbon atoms represented by R includes an alkyl group, an alkenyl group, an alkynyl group, and the like. Although an alkyl group can be mentioned, an alkyl group is preferable. Examples of the alkyl chain include n-hexyl group, n-heptyl group, n-octyl group, n-decyl group, n-dodecyl group, n-tetradecyl group, n-hexadecyl group, n-octadecyl group, isostearyl group, 2-ethylhexyl group etc. are mentioned. Among these, from the viewpoint of blending and effects, an alkyl group having 8 to 16 carbon atoms is preferable, and an alkyl group having 8 to 12 carbon atoms is more preferable.
The hydrogen atom of the aliphatic hydrocarbon group may be substituted with a substituent, and examples of the substituent include an alkoxy group having 1 to 6 carbon atoms and a hydroxyl group.

In formula (1), examples of the alkylene group of A include a linear ethylene group, a propylene group (trimethylene group), or an ethylene group having a methyl branch (glycerin group). A branched ethylene group is preferred.
Although m shows the number of 0-200, 0-12 are preferable from the surface of an effect, and 0 is still more preferable.

In Formula (1), G ¹ represents a reducing sugar residue having 5 to 6 carbon atoms, and examples of the reducing sugar include glucose, fructose, galactose, xylose, mannose, and arabinose. These reducing sugars may be either bilanose type or furanose type, or may be a mixture of the above sugars. The glycosidic bond between sugars may be either α or β, or a mixture thereof.
In formula (1), G ² represents a galactose residue, which may be either a pyranose type or a furanose type, or a mixture thereof, but the pyranose type is preferred from the viewpoint of effect. The glycosidic bond between sugars may be either α or β, or a mixture thereof.
Although n is a number from 0 to 30, 0 to 6 are preferable and 0 to 3 are more preferable from the viewpoints of effects and production. When n is not 0, the linkage mode of the sugar chain may be a 1-2, 1-3, 1-4, 1-6 bond, or a combination mode in which these are mixed.

  The compound represented by the formula (1) can be produced by, for example, the method of Hori et al. (Pharmaceutical Journal, vol. 79, No. 1, p80-83) or the method disclosed in Japanese Patent Application Laid-Open No. 2007-291083.

  The content of the compound represented by the formula (1) in the malodor suppressing agent of the present invention is preferably 0.01% by mass or more, particularly 0.1% by mass or more, and more preferably 0.5% by mass or more from the viewpoint of the effect. Moreover, 50 mass% or less is preferable from an economical surface.

  The malodor suppressant of the present invention can be added to various compositions such as oils by appropriately adding surfactants, emulsifiers, dispersants, wetting agents, stabilizers, propellants and the like that are generally used as necessary. It can be formulated in the form of emulsion, wettable powder, spray, aerosol, smoke, coating agent, cleaning agent, powder, granule. Here, the content of the general surfactant is not particularly limited. For example, it is preferably 5% by mass or less, more preferably 3% by mass or less, and particularly preferably 1% in the malodor control agent. It is below mass%. By spraying, spraying or applying these to various environments where malodors derived from microorganisms are generated, such as kitchens in homes, bathroom drains, sewage pipes, drains, pipes in factories, etc. be able to.

In the malodor suppressant of the present invention, a bactericidal agent, an antibacterial antifungal agent, an antiseptic / antifungal agent, an antibiotic, a penetration enhancer, a deodorant, a fragrance and the like can be blended as necessary.
Of these, the antibacterial agent or antibacterial antifungal agent is not particularly limited as long as it is generally used. , Natural antibacterial components such as mustard essential oil and wasabi essential oil.
Examples of antiseptic / antifungal agents include parabens, 2-phenoxyethanol, benzoic acid, salicylic acid, sorbic acid, dehydroacetic acid, p-toluenesulfonic acid and salts of these acids, alcohols such as ethanol and isopropanol, and benzalkonium chloride. Quaternary ammonium salts, polyhydric alcohols having antiseptic properties such as alkyl glyceryl ethers, medium chain fatty acids and esters thereof, and chelating agents such as EDTA.

Reference Example 1 Production of α, β-decylgalactoside D-galactose and a decanol isomer mixture (decanol, Kyowa Hakko Chemical Co., Ltd.) are dehydrated under heating and reduced pressure conditions in the presence of a catalytic amount of paratoluenesulfonic acid monohydrate. While reacting. After the reaction, an aqueous sodium hydroxide solution was added to neutralize the catalyst, and unreacted D-galactose was removed from the resulting mixture by filtration. Decyl galactoside was obtained by distilling off the unreacted alcohol from the filtrate under reduced pressure. As a result of analysis by gel permeation chromatography and ¹ H-NMR, the average condensation degree of the obtained galactoside was 1.15, and the composition of monogalactoside in the composition was pyranoside / furanoside = 46/54, α / β of pyranoside. The ratio was 67/33. This was used as the test substance of Examples 2 and 3 as α, β-decylgalactoside.

Reference Example 2 Production of α, β-octylgalactoside Octylgalactoside was obtained according to Reference Example 1 except that the starting alcohol was changed to octyl alcohol. As a result of analysis by gel permeation chromatography and ¹ H-NMR, the average condensation degree of the obtained galactoside was 1.18, and the composition of monogalactoside in the composition was pyranoside / furanoside = 43/57, α / β of pyranoside. The ratio was 67/33. This was used as the test substance of Example 1 as α, β-octylgalactoside.

Examples 1 to 3 and Comparative Examples 1 to 5 Microorganism-derived malodor control effect (1) Strain used Pseudomonas aeruginosa (Pseudomonas aeruginosa) NBRC12689,
Pseudomonas aeruginosa (Pseudomonas aeruginosa) NBRC13275,
It was used.

(2) Evaluation of bad odor suppression effect Evaluation of bad odor suppression effect is carried out by adding a culture medium in which bacteria are suspended and an evaluation sample to a lower tank of a container whose upper and lower sides are partitioned by a gas permeable membrane, and cultivating the generated thiol group. The generated volatile compounds were captured by the 5,5′-dithiobis- [2-nitrobenzene acid] (DTNB) solution added to the upper tank, and the amount of the generated volatile compound was measured by measuring the absorbance of the upper tank solution (Anal Chem. 1987, 59, 1509-1512). About the suppression effect, the case where a sample was not added was made into the relative amount of generation | occurrence | production of bad odor as 100%. Specific operations are shown below.

One colony of Pseudomonas aeruginosa stored in a standard agar medium at 0 ° C. was scraped with a 1 μL platinum loop, inoculated into 5 mL of LB liquid medium, and cultured under aerobic conditions at 37 ° C. for 20 hours. 2 μL of the liquid medium in which the bacteria were cultured was added to 10 mL of Mueller Hinton liquid medium, which was used as the bacterial suspension medium.
0.5 mL of a mixed solution having the composition shown in Table 1 or Table 2 is added to a lower tank of a 15 mL centrifuge vial whose upper and lower sides are separated by a gas permeable membrane, and a 0.25 M phosphate buffer (pH 7. 0.4 mL of the DTNB solution (2 mM) dissolved in 2) was added, sealed, and cultured for 18 hours. After completion of the culture, 0.1 mL of the DTNB solution in the upper tank is taken, 0.1 mL of 0.25M phosphate buffer (pH 7.2) is added, and the absorbance at 412 nm or 405 nm is measured to determine the thiol group. The amount of generated volatile compounds was measured. For comparison, the effects of adding polyoxyethylene (12) lauryl ether (Emulgen 120; manufactured by Kao Corporation) and lauryl glucoside (Mydol 12; manufactured by Kao Corporation) were also confirmed. The evaluation results are summarized in Tables 1 and 2.

  From the results of Tables 1 and 2, the malodor suppressor of the present invention effectively suppresses the generation of volatile compounds having a thiol group, and the effect is significantly superior to alkyl glucosides with similar chemical structures. I understand.

Claims (2)

Following formula:
_{R- (OA) m -O- (G} 1) n -G 2 (1)
[Wherein, R represents a linear or branched aliphatic hydrocarbon group having 10 carbon atoms which may be substituted with a substituent, and A represents a linear or branched alkylene group having 2 to 3 carbon atoms. G ¹ represents a reducing sugar residue having 5 to 6 carbon atoms, G ² represents a residue derived from galactose, m represents a number of 0, and n represents a number of 0. ]
The malodor control agent for suppressing generation | occurrence | production of the malodor by the bacteria of the genus Pseudomonas which uses the compound represented by these as an active ingredient. The malodor control agent for suppressing generation | occurrence | production of the malodor by the fungus of Pseudomonas of Claim 1 whose content of the compound represented by Formula (1) is 0.01 mass% or more and 50 mass% or less.