JP5339734B2 - Odor control agent - Google Patents

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JP5339734B2
JP5339734B2 JP2008022531A JP2008022531A JP5339734B2 JP 5339734 B2 JP5339734 B2 JP 5339734B2 JP 2008022531 A JP2008022531 A JP 2008022531A JP 2008022531 A JP2008022531 A JP 2008022531A JP 5339734 B2 JP5339734 B2 JP 5339734B2
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哲也 宮島
俊一 秋葉
克弥 上野
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Kao Corp
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Description

本発明は、微生物が発生する悪臭を抑制する悪臭抑制剤に関する。   The present invention relates to a malodor control agent that suppresses malodor generated by microorganisms.

一般に家庭の台所、浴室、その他下水等の排水口から発生する悪臭は、腐敗菌として知られるシュードモナス属などの菌が、排水口等に付着、増殖後、たんぱく質やアミノ酸等を、分解・代謝することにより生成する揮発性チオール類やアミン類などが原因であることが知られている(非特許文献1)。
この微生物由来の悪臭の発生抑制のために、一般的な洗浄剤による物理的な微生物除去や殺菌剤による殺菌等が行なわれているが、これら微生物はぬめりの原因であるバイオフィルムを形成することで洗浄除去や薬剤、熱などのストレスに対し抵抗性を有するため、通常の洗浄や殺菌方法では悪臭抑制効果が十分に発揮できない事が多い。
アルキルグリコシドに、これらのバイオフィルムの形成抑制、除去効果があることは知られている(特許文献1)。
しかしながら、どのような成分が微生物由来の悪臭の抑制効果があるかについては、知られていない。
特開2006−347941号公報 「バイオフィルム」森崎久雄著、サイエンスフォーラム社発行、1998年、119ページ
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

従って、本発明は、安全性が高く居住空間などに広く使用可能な、微生物由来の悪臭抑制剤を提供することを目的とする。   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.

本発明者らは、悪臭抑制効果が高く、かつ安全性が高く居住空間などに広く使用可能な化合物について検討したところ、下記式(1)で表されるアルキルガラクトシド類が化学構造が類似しているアルキルグリコシドに比べ顕著に優れた微生物由来の悪臭抑制効果を有することを見出し本発明を完成した。
すなわち本発明は、下記式(1):
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−(G1n−G2 (1) R- (OA) m -O- (G 1) n -G 2 (1)

〔式中、Rは置換基で置換されていても良い直鎖または分岐鎖の炭素数6〜18の脂肪族炭化水素基を示し、Aは直鎖または分岐鎖の炭素数2〜3のアルキレン基を示し、G1は炭素数5〜6の還元糖残基を示し、G2はガラクトース由来の残基を示し、mは0〜200の数を示し、nは0〜30の数を示す。〕
で表される化合物を有効成分とする微生物由来の悪臭抑制剤を提供するものである。
[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.

本発明によれば、住居内及び産業上の様々な環境において、微生物由来の悪臭を、安全、簡便、かつ効率的に抑制できる。また、本発明の悪臭抑制剤の効果は、化学構造が類似しているアルキルグリコシドに比べて顕著に優れていることから、単なるバイオフィルム抑制効果に基くものではないと考えられる。   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.

本発明に用いられる式(1)で表される化合物において、Rで示される直鎖または分岐鎖の炭素数6〜18の脂肪族炭化水素基としては、アルキル基、アルケニル基、アルキニル基などを挙げることができるが、アルキル基が好ましい。アルキル鎖としては、例えばn−ヘキシル基、n−ヘプチル基、n−オクチル基,n−デシル基,n−ドデシル基、n−テトラデシル基、n−ヘキサデシル基、n−オクタデシル基、イソステアリル基、2−エチルヘキシル基などが挙げられる。この内、配合上及び効果の面から、炭素数8〜16のアルキル基が好ましく、炭素数8〜12のアルキル基がより好ましい。
脂肪族炭化水素基の水素原子は、置換基で置換されていても良く、この置換基としては、炭素数1〜6のアルコキシ基、水酸基等が挙げられる。
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.

式(1)中、Aのアルキレン基としては例えば直鎖のエチレン基,プロピレン基(トリメチレン基)またはメチル分岐を有するエチレン基(グリセリン基)が挙げられるが、原料入手の都合からエチレン基及びメチル分岐を有するエチレン基が好ましい。
mは0〜200の数を示すが、効果の面から0〜12が好ましく、更に0がより好ましい。
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.

式(1)中、G1は炭素数5〜6の還元糖残基を示すが、還元糖としてはグルコース、フルクトース、ガラクトース、キシロース、マンノース、アラビノース等が挙げられる。これらの還元糖は、ビラノース型、フラノース型のどちらでも良く、また上記糖の混合物であっても良い。糖間のグリコシド結合は、α,βのどちらでも良く、またそれらの混合物であっても良い。
式(1)中、G2はガラクトース残基を示し、ピラノース型、フラノース型のどちらでも良く、またそれらの混合物であっても良いが、効果の点からピラノース型が好ましい。糖間のグリコシド結合は、α、βのどちらでも良く、またそれらの混合物であっても良い。
nは0〜30の数であるが、効果ならびに製造の面から0〜6が好ましく、0〜3がより好ましい。nが0でない場合、糖鎖の結合様式は、1−2,1−3,1−4,1−6結合、及びこれらが混合された結合様式であってもよい。
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.

式(1)で表される化合物は、例えば堀らの方法(薬学雑誌,vol.79,No.1,p80-83)や特開2007−291083に開示された方法によって製造することができる。   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.

本発明の悪臭抑制剤における式(1)に示した化合物の含有量としては、効果の面から0.01質量%以上が好ましく、特に0.1質量%以上、更に0.5質量%以上が好ましい。また、経済的な面から、50質量%以下が好ましい。   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.

本発明の悪臭抑制剤は、必要に応じて一般に使用されている界面活性剤、乳化剤、分散剤、湿潤剤、安定剤、噴射剤などを適宜添加することにより、各種の組成物、例えば油剤、乳剤、水和剤、噴霧剤、エアゾール剤、燻煙剤、塗布剤、洗浄剤、粉剤、粒剤の形態として製剤化することができる。ここで、一般的な界面活性剤の含有量は、特に限定されるものでないが、例えば、悪臭抑制剤中5質量%以下であることが好ましく、より好ましくは3質量%以下、特に好ましくは1質量%以下である。これらを微生物由来の悪臭が発生する種々の環境、例えば住居における台所、浴室の排水口、下水の配管、排水溝、工場等の配管などに散布、噴霧または塗布することにより、その効果を発現することができる。   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.

本発明の悪臭抑制剤には、必要に応じて殺菌剤、抗菌抗カビ剤、防腐防黴剤、抗生物質、浸透促進剤、消臭剤、芳香剤などを配合することができる。
このうち殺菌剤または抗菌抗カビ剤としては、一般に使用されているものであれば特に限定されないが、例えばチアベンダゾール、トリクロサン、クロルヘキシジン、ジンクピリチオン、クロルキシレノールなどや、キトサン、カテキン、チモール、ヒノキチオール、孟宗竹エキス、カラシ精油、ワサビ精油などの天然由来の抗菌成分などが挙げられる。
防腐防黴剤としては、例えばパラベン類、2−フェノキシエタノールや安息香酸、サリチル酸、ソルビン酸、デヒドロ酢酸、p−トルエンスルホン酸及びそれら酸の塩類、エタノールやイソプロパノールなどのアルコール類、塩化ベンザルコニウムなどの4級アンモニウム塩、アルキルグリセリルエーテル等の防腐力を有する多価アルコール、中鎖脂肪酸やそのエステル類、EDTAなどのキレート剤などが挙げられる。
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.

参考例1 α,β−デシルガラクトシドの製造
D−ガラクトースとデカノール異性体混合物(デカノール,協和発酵ケミカル(株))を触媒量のパラトルエンスルホン酸1水和物存在下、加熱、減圧条件で脱水しながら反応させた。反応後、水酸化ナトリウム水溶液を加えて触媒を中和し、得られた混合物からろ過により未反応のD−ガラクトースを除去した。ろ液から未反応のアルコールを減圧下で留去することでデシルガラクトシドを得た。ゲル浸透クロマトグラフィー並びに1H−NMRによる分析の結果、得られたガラクドシドの平均縮合度は1.15であり、組成中のモノガラクトシドの組成はピラノシド/フラノシド=46/54、ピラノシドのα/β比は67/33であった。これをα,β−デシルガラクトシドとして実施例2、3の試験物質として用いた。
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.

参考例2 α,β−オクチルガラクトシドの製造
原料アルコールをオクチルアルコールに変更した以外は参考例1に従い、オクチルガラクトシドを得た。ゲル浸透クロマトグラフィー並びに1H−NMRによる分析の結果、得られたガラクドシドの平均縮合度は1.18であり、組成中のモノガラクトシドの組成はピラノシド/フラノシド=43/57、ピラノシドのα/β比は67/33であった。これをα,β−オクチルガラクトシドとして実施例1の試験物質として用いた。
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.

実施例1〜3及び比較例1〜5 微生物由来の悪臭抑制効果
(1)使用菌株
流しの腐敗菌であるシュードモナス属の菌として
シュードモナス・アエルギノーザ[Pseudomonas aeruginosa(緑膿菌)]NBRC12689、
シュードモナス・アエルギノーザ[Pseudomonas aeruginosa(緑膿菌)]NBRC13275、
を使用した。
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)悪臭抑制効果の評価
悪臭抑制効果の評価は、上下をガス透過膜で仕切った容器の下槽に、菌を懸濁させた培地、評価サンプルを加えて培養し、発生するチオール基を有する揮発性化合物を、上槽に加えた5,5'-ジチオビス−[2−ニトロベンゼン酸](DTNB)溶液で捕捉し、更に上槽溶液の吸光度測定を行なうことで発生量を測定した(Anal.Chem.1987,59,1509-1512)。抑制効果については、サンプルを加えない場合を悪臭の発生量100%として、相対的な評価を行なった。具体的な操作を以下に示す。
(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.

標準寒天培地に0℃で保存した緑膿菌1コロニーを1μLの白金耳で掻きとり、5mLのLB液体培地に植菌後、37℃の好気性条件下で20時間培養した。菌を培養した液体培地2μLをミューラーヒントン液体培地10mLに添加し、これを菌懸濁培地とした。
上下をガス透過膜で仕切った15mLの遠心分離用バイアルの下槽に、表1または表2に示した組成の混合液0.5mLを加え、上槽に0.25Mリン酸緩衝液(pH7.2)に溶解したDTNB溶液(2mM)0.4mLを加えて密栓し、18時間培養した。培養終了後、上槽のDTNB溶液0.1mLを分取して、0.25Mリン酸緩衝液(pH7.2)0.1mLを加え、412nm又は405nmでの吸光度を測定して、チオール基を有する揮発性化合物の発生量の測定を行なった。また比較として、ポリオキシエチレン(12)ラウリルエーテル(エマルゲン120;花王(株)製),ラウリルグルコシド(マイドール 12;花王(株)製)の添加効果も確認した。評価結果をまとめて表1、2に示す。
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.

Figure 0005339734
Figure 0005339734

Figure 0005339734
Figure 0005339734

表1、2の結果から、本発明の悪臭抑制剤は、チオール基を有する揮発性化合物の発生を有効に抑制し、その効果は化学構造が類似するアルキルグルコシドに比べて顕著に優れていることが判る。   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)

下記式:
R−(OA)m−O−(G1n−G2 (1)
〔式中、Rは置換基で置換されていても良い直鎖または分岐鎖の炭素数10の脂肪族炭化水素基を示し、Aは直鎖または分岐鎖の炭素数2〜3のアルキレン基を示し、G1は炭素数5〜6の還元糖残基を示し、G2はガラクトース由来の残基を示し、mは0の数を示し、nは0の数を示す。〕
で表される化合物を有効成分とするシュードモナス属の菌による悪臭の発生を抑制するための悪臭抑制剤。
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.
式(1)で表される化合物の含有量が、0.01質量%以上50質量%以下である請求項1記載のシュードモナス属の菌による悪臭の発生を抑制するための悪臭抑制剤。 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.
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