JP2011229894A - Composition for suppressing emission of urine odor - Google Patents
Composition for suppressing emission of urine odor Download PDFInfo
- Publication number
- JP2011229894A JP2011229894A JP2010139002A JP2010139002A JP2011229894A JP 2011229894 A JP2011229894 A JP 2011229894A JP 2010139002 A JP2010139002 A JP 2010139002A JP 2010139002 A JP2010139002 A JP 2010139002A JP 2011229894 A JP2011229894 A JP 2011229894A
- Authority
- JP
- Japan
- Prior art keywords
- urine
- composition
- glucuronidase
- suppressing
- urine odor
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
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Abstract
Description
本発明は、β-グルクロニダーゼ阻害剤と0.01〜10重量%のアルキルグリコシド型非イオン界面活性剤とを含有する尿臭生成抑制用組成物に関する。 The present invention relates to a composition for suppressing urine odor production comprising a β-glucuronidase inhibitor and 0.01 to 10% by weight of an alkylglycoside type nonionic surfactant.
近年、消費者の衛生志向の高まりから、見た目の汚ればかりでなく汚れの存在を想起させる臭気についても除去することが強く望まれている。特に尿及び便に関しては存在を生活環境から切り離すことはできず、更に、その臭気は排泄物そのものを強く想起させることから、ヒトに与える不快感は生活環境悪臭の中でもとりわけ大きい。トイレにおいては、便は水洗により容易に屋外に排出することができるが、尿に関しては少量が飛沫として便器周辺部、又はトイレの床、内壁等に残り、その存在が目視で確認しづらいことから長期に渡ってその場に残り、悪臭の発生源となりやすい。また、下着やオムツ、生理用品などのサニタリー製品も、尿が付着した状態で生活環境中に一定期間存在する場面があり、尿を由来とした悪臭の発生源となりうる。 In recent years, it has been strongly desired to remove not only the appearance of dirt but also the odor reminiscent of the presence of dirt due to the increase in consumer hygiene. Especially for urine and feces, the existence cannot be separated from the living environment. Furthermore, since the odor strongly reminds the excrement itself, discomfort given to humans is particularly great among the bad odors of the living environment. In toilets, stool can be easily discharged outdoors by washing with water, but a small amount of urine remains as a splash on the toilet periphery, toilet floor, inner wall, etc., and its presence is difficult to check visually. Remains on the spot for a long time and tends to be a source of bad odor. In addition, sanitary products such as underwear, diapers, and sanitary products may exist in the living environment for a certain period of time with urine attached, and can be a source of malodor originating from urine.
一方、通常、排尿直後の尿の臭気は非常に弱く、尿に由来する悪臭成分の大部分は微生物由来の代謝酵素の作用によって時間の経過に伴い発生してくるものと考えられている。このため、尿からの悪臭成分の生成を元から持続的に抑制できる技術の開発が望まれている。 On the other hand, the odor of urine immediately after urination is very weak, and it is considered that most of the malodorous components derived from urine are generated with the passage of time due to the action of metabolic enzymes derived from microorganisms. For this reason, development of the technique which can suppress continuously the production | generation of the malodorous component from urine from the beginning is desired.
このような尿由来の悪臭成分としては、尿素からウレアーゼによって生じるアンモニアが挙げられ、その生成抑制技術として、ウレアーゼ活性阻害剤を用いたアンモニアの発生抑制技術が提案されている(例えば特許文献1〜4参照)。 Such urine-derived malodorous components include ammonia produced from urea by urease, and as its production suppression technology, ammonia generation suppression technology using a urease activity inhibitor has been proposed (for example, Patent Documents 1 to 3). 4).
しかしながら、アンモニアは悪臭成分としては閾値が高い(高濃度でないと臭いを感じない)ため、水洗式の普及により排泄物が即時的に屋外へ排出されるようになった現在においては、アンモニア臭が強く感じられる場面は非常に稀である。 However, because ammonia has a high threshold as a bad odor component (it does not feel odor unless it is high in concentration), nowadays the excrement is immediately discharged to the outdoors due to the widespread use of the flushing method. Scenes that feel strong are very rare.
また、特許文献5では微生物由来のβ-グルクロニダーゼによって尿より代謝生成されるフェノール化合物及びインドール類が尿臭に大きく寄与するとして、β-グルクロニダーゼ阻害剤を用いた尿臭気の生成抑制技術が提案されている。
特許文献5の技術は、微生物由来のβ-グルクロニダーゼが細胞外に放出されている場合に特に有効であると考えられる。しかしながら、尿臭発生の現場においてβ-グルクロニダーゼは細胞外だけでなく、細胞内や、グラム陰性菌におけるペリプラズム空間等の外部から剤が作用しづらい領域にも存在するものと考えられ、このような細胞構造によって保持されたβ-グルクロニダーゼ(以下、「細胞内β-グルクロニダーゼ」という)に対しても有効な技術については知られていない。特に微生物の細胞膜を破壊しない場合、例えば殺菌剤を含まない場合、細胞内β‐グルクロニダーゼにβ‐グルクロニダーゼ阻害剤を有効に作用させることは極めて困難であると考えられる。
The technique of
即ち、本発明の課題は、尿中に溶解又は分散したβ-グルクロニダーゼだけでなく、微生物の細胞内β-グルクロニダーゼに対してもβ-グルクロニダーゼ活性を効果的に阻害することによって、尿に由来する悪臭の生成を効果的に抑制できる組成物を提供することにある。 That is, the problem of the present invention is derived from urine by effectively inhibiting β-glucuronidase activity not only against β-glucuronidase dissolved or dispersed in urine but also against intracellular β-glucuronidase of microorganisms. It is providing the composition which can suppress the production | generation of a bad odor effectively.
本発明者らは、特定の界面活性剤は殺菌効果を発現しない、即ち細胞膜を破壊できない濃度であっても、驚くべきことに、β‐グルクロニダーゼ阻害剤と併用することによって、微生物の細胞内β-グルクロニダーゼに対するβ-グルクロニダーゼ阻害剤の効果を向上させることを見出した。また、これよりβ-グルクロニダーゼ阻害剤と特定の界面活性剤からなる組成物が不快な尿臭の発生を持続的に抑制し、該組成物を尿が関連する製品に使用することにより、これら製品に対して尿臭生成抑制効果を付与できることを見出した。 We have surprisingly found that certain surfactants do not exert a bactericidal effect, i.e. at concentrations that do not disrupt the cell membrane, but surprisingly, in combination with β-glucuronidase inhibitors, -We have found that the effect of β-glucuronidase inhibitors on glucuronidase is improved. In addition, a composition comprising a β-glucuronidase inhibitor and a specific surfactant continuously suppresses the generation of unpleasant urine odor, and the composition is used in products related to urine. It was found that a urine odor production inhibitory effect can be imparted to the above.
即ち本発明は、β-グルクロニダーゼ阻害剤と0.01〜10重量%のアルキルグリコシド型非イオン界面活性剤とを含有する尿臭生成抑制用組成物を提供するものである。 That is, the present invention provides a composition for suppressing urine odor production comprising a β-glucuronidase inhibitor and 0.01 to 10% by weight of an alkylglycoside nonionic surfactant.
更に本発明は、上記尿臭生成抑制用組成物を、吐出装置を備える容器に収容してなる吐出型製品を提供するものである。 Furthermore, this invention provides the discharge type product which accommodates the said composition for urine odor production | generation suppression in the container provided with a discharge device.
更に本発明は、上記尿臭生成抑制用組成物を、対象物に尿が付着する前又は尿が付着してから乾燥する前に適用する尿臭の生成抑制方法を提供するものである。 Furthermore, the present invention provides a method for suppressing the generation of urine odor, wherein the composition for suppressing urine odor generation is applied before urine adheres to an object or before drying after urine has adhered.
本発明の尿臭生成抑制用組成物は、尿から時間の経過に伴い生成する臭気を持続的に抑制できる。 The composition for suppressing urine odor production of the present invention can continuously suppress the odor generated from the urine over time.
本発明の尿臭生成抑制用組成物は、尿中に溶解又は分散したβ-グルクロニダーゼだけでなく、微生物、特に尿臭産生菌の細胞内β-グルクロニダーゼに対しても、その活性を効果的に抑制し、これによってトイレ環境、サニタリー製品、下着等の衣類又は肌、あるいは寝具等の尿が付着する恐れのあるあらゆる物品あるいは部位について、付着した尿から時間の経過に伴い生成する臭気を持続的に抑制する。このため本発明の尿臭生成抑制用組成物は優れた防臭効果を有する洗浄剤、消臭剤等の環境衛生製品、及びオムツ、生理用品、犬、猫等のペット用排泄物シート等の動物の排泄物関連品等のサニタリー製品において有用である。 The composition for suppressing urine odor production according to the present invention is effective not only for β-glucuronidase dissolved or dispersed in urine but also for microorganisms, particularly intracellular β-glucuronidase of urine odor producing bacteria. Suppressing the odor generated with the passage of time from the attached urine for any articles or parts that may be attached to the toilet environment, sanitary products, clothing such as underwear, skin, or bedding To suppress. For this reason, the composition for suppressing urine odor production of the present invention has excellent deodorizing effects, environmental hygiene products such as detergents and deodorants, and animals such as diapers, sanitary products, dog excrement sheets such as dogs and cats. It is useful in sanitary products such as excrement related products.
上記において尿臭産生菌とは、尿中又は尿に関連した環境に棲息する微生物の中でも特にβ-グルクロニダーゼ活性を有するものであり、ヒト等の動物の尿、便、若しくは尿と便の混合物、好ましくは便器やトイレ床等のトイレ環境内やサニタリー製品等の対象物に付着した尿、便、若しくは尿と便の混合物、又はこれらが付着若しくは接触した履歴を有する便器やトイレ床等のトイレ環境内やサニタリー製品等の付着物から抽出したβ−グルクロニダーゼ活性菌であり、例えばスタフィロコッカス属細菌、大腸菌等が挙げられる。 In the above, urine odor producing bacteria are those having β-glucuronidase activity among microorganisms that inhabit urine or the environment related to urine, urine of animals such as humans, feces, or a mixture of urine and feces, Preferably, urine, stool, or a mixture of urine and stool attached to a toilet environment such as a toilet bowl or toilet floor or a sanitary product, or a toilet environment such as a toilet bowl or toilet floor having a history of adhesion or contact thereof It is a β-glucuronidase active bacterium extracted from the inside or sanitary products, and examples thereof include Staphylococcus bacteria and Escherichia coli.
また本発明において細胞内β-グルクロニダーゼとは、細胞内、細胞膜又はグラム陰性菌におけるペリプラズム空間等に存在し、このような細胞構造によって保持されたβ-グルクロニダーゼと定義され、細胞質中に存在するβ-グルクロニダーゼには限定されない。本発明において尿臭産生菌の細胞内β-グルクロニダーゼは、例えば尿臭産生菌をβ-グルクロニダーゼが発現する条件で培養し、遠心操作によって培養上清中に溶解又は分散したβ-グルクロニダーゼを除いた菌体部分を好適に用いることができる。 Further, in the present invention, intracellular β-glucuronidase is defined as β-glucuronidase existing in the periplasmic space or the like in cells, cell membranes or gram-negative bacteria, and retained in such a cell structure, and present in the cytoplasm. -Not limited to glucuronidase. In the present invention, the intracellular β-glucuronidase of the urine odor producing bacteria was cultured, for example, under the conditions in which β-glucuronidase was expressed, and β-glucuronidase dissolved or dispersed in the culture supernatant was removed by centrifugation. The cell part can be preferably used.
また、本発明の尿臭生成抑制用組成物は、β-グルクロニダーゼ活性を効果的に抑制するものであることから、β-グルクロニダーゼの作用によって生じる尿臭以外の様々な課題を解決する手段にも用いることができ、例えば、揮発性ステロイドに由来する体臭の生成抑制剤、膀胱癌又は大腸癌の発生を低減させる薬剤又は食品としても用いることができる。 Further, since the composition for suppressing urine odor production of the present invention effectively suppresses β-glucuronidase activity, it is also a means for solving various problems other than urine odor caused by the action of β-glucuronidase. For example, it can be used as a body odor production inhibitor derived from volatile steroids, a drug or food that reduces the occurrence of bladder cancer or colon cancer.
〔β-グルクロニダーゼ阻害剤〕
β-グルクロニダーゼとは、各種のアルコール類、フェノール類、アミン類等がグルクロン酸抱合された化合物(グルクロニド)を加水分解する酵素であり、細菌、真菌、植物、動物など多くの生物に存在することが知られている。体外に排出された尿の分解には微生物の関与が大きいため、本発明においては、細菌及び真菌由来のβ-グルクロニダーゼが重要である。β-グルクロニダーゼを有することが知られる微生物としては、例えばEscherichia coli、Lactobacillus brevis、Propionibacterium acnes、Clostridium perfringens、Staphylococcus haemolyticus、Streptococcus agalactiae、Streptococcus pyogenes、Haemophilus somunus、Shigela sonnei、Aspergillus niger等が挙げられ、これら微生物に由来するβ-グルクロニダーゼはいずれも共通のドメインを有する酵素群に分類される。更にはヒト血漿由来のβ-グルクロニダーゼも同様のタンパク質群に分類される。
[Β-glucuronidase inhibitor]
β-glucuronidase is an enzyme that hydrolyzes glucuronide-conjugated compounds (glucuronides) with various alcohols, phenols, amines, etc., and exists in many organisms such as bacteria, fungi, plants, and animals. It has been known. In the present invention, β-glucuronidase derived from bacteria and fungi is important because microorganisms are greatly involved in the degradation of urine excreted outside the body. The microorganisms are known to have β- glucuronidase, for example Escherichia coli, Lactobacillus brevis, Propionibacterium acnes , Clostridium perfringens, Staphylococcus haemolyticus, Streptococcus agalactiae, Streptococcus pyogenes, Haemophilus somunus, Shigela sonnei, Aspergillus niger , and these microorganisms All β-glucuronidases derived from are classified into enzyme groups having a common domain. Furthermore, β-glucuronidase derived from human plasma is also classified into a similar protein group.
即ち本発明においてβ-グルクロニダーゼ阻害剤とは、β-グルクロニダーゼに作用することによってグルクロニドの加水分解反応を抑制するものであり、細菌又は真菌由来のβ-グルクロニダーゼを用いた試験において抑制効果が示されるものが好ましく、更には大腸菌由来のβ-グルクロニダーゼを用いた試験において抑制効果が示されるものがより好ましい。 That is, in the present invention, the β-glucuronidase inhibitor is a substance that suppresses the hydrolysis reaction of glucuronide by acting on β-glucuronidase, and exhibits an inhibitory effect in a test using β-glucuronidase derived from bacteria or fungi. In particular, those showing an inhibitory effect in a test using β-glucuronidase derived from E. coli are more preferred.
以下に、このようなβ-グルクロニダーゼ阻害剤を列記するが、本発明において用いられるβ-グルクロニダーゼ阻害剤は上記の作用を有するものであればよく、以下に記載するものに限定されるものではない。 Hereinafter, such β-glucuronidase inhibitors are listed, but the β-glucuronidase inhibitors used in the present invention are not limited to those described below as long as they have the above-described action. .
1.次の一般式(1)で表される大環状ケトン。 1. Macrocyclic ketone represented by the following general formula (1).
〔式中、n1は9〜13の整数を示し、m1は0〜2の整数を示し、破線部に一つの二重結合を含んでいてもよい。〕 Wherein, n 1 represents an integer of 9 to 13, m 1 represents an integer of 0 to 2, may contain one double bond broken line. ]
例えば、3-メチル-4(5)-シクロペンタデセン-1-オン(Firmenich社製品名;ムセノンデルタ)、3-メチルシクロペンタデカノン(Firmenich社製品名;ムスコン)、4-シクロペンタデセン-1-オン(Firmenich社製品名;エギザルテノン、IFF社製品名:ムスクZ-4)、5-シクロヘキサデセン-1-オン(曽田香料社製品名;ムスクTM2)、8-シクロヘキサデセン-1-オン(Symrise社製品名;グロバノン)、9-シクロヘプタデセン-1-オン(Firmenich社製品名;シベトン)、シクロペンタデカノン(Firmenich社製品名;エグザルトン)が挙げられる。 For example, 3-methyl-4 (5) -cyclopentadecene-1-one (Firmenich product name; Musenon Delta), 3-methylcyclopentadecanone (Firmenich product name; Muscon), 4-cyclopentadecene-1 -On (Firmenich product name; Egizartenon, IFF product name: Musk Z-4), 5-cyclohexadecen-1-one (Manda Scent Inc. product name: Musk TM2), 8-cyclohexadecen-1-one (Symrise) Company product name: Globanon), 9-cycloheptadecen-1-one (Firmenich product name: Civeton), cyclopentadecanone (Firmenich product name: Exalton).
一般式(1)で表される大環状ケトン化合物のうち、環状構造内に二重結合を一つ含むものが好ましく、例えば、3-メチル-4(5)-シクロペンタデセン-1-オン、4-シクロペンタデセン-1-オン、5-シクロヘキサデセン-1-オン、8-シクロヘキサデセン-1-オン、9-シクロヘプタデセン-1-オンが挙げられる。更に、この二重結合が、ケトンのカルボニル基から最も離れた位置の炭素−炭素結合、又はこれに隣接する炭素−炭素結合に存在することが好ましく、例えば、8-シクロヘキサデセン-1-オン、9-シクロヘプタデセン-1-オンが挙げられる。また、一般式(1)において、n1+m1は、9〜13であることが好ましく、n1は、11又は12であることが好ましい。 Among the macrocyclic ketone compounds represented by the general formula (1), those containing one double bond in the cyclic structure are preferable, for example, 3-methyl-4 (5) -cyclopentadecene-1-one, 4-cyclopentadecene-1-one, 5-cyclohexadecene-1-one, 8-cyclohexadecene-1-one, and 9-cycloheptadecene-1-one. Furthermore, the double bond is preferably present in the carbon-carbon bond located farthest from the carbonyl group of the ketone, or adjacent to the carbon-carbon bond, such as 8-cyclohexadecen-1-one, 9-cycloheptadecen-1-one. In the general formula (1), n 1 + m 1 is preferably 9 to 13, and n 1 is preferably 11 or 12.
2.次の一般式(2)で表される大環状ラクトン。 2. Macrocyclic lactone represented by the following general formula (2).
〔式中、n2は9〜13の整数を示し、m2は0〜3の整数を示し、破線部に一つの二重結合を含む。ただし、n2+m2=9〜14を満たすものとする。〕 Wherein, n 2 represents an integer of 9 to 13, m 2 represents an integer of 0 to 3, including one double bond broken line. However, it is assumed that satisfies n 2 + m 2 = 9~14. ]
例えば、4(5)-シクロペンタデセノライド(Firmenich社製品名:ハバノライド)、7-シクロヘキサデセノライド(アンブレットライド)が挙げられる。一般式(2)で表される大環状ラクトン化合物において、式中のn2が12であるものが好ましく、特に7-シクロヘキサデセノライドが好ましい。 Examples thereof include 4 (5) -cyclopentadecenolide (Firmenich product name: havanolide) and 7-cyclohexadecenolide (ambretride). In the macrocyclic lactone compound represented by the general formula (2), those in which n 2 is 12 are preferable, and 7-cyclohexadecenolide is particularly preferable.
3.次の一般式(3)で表される大環状オキサラクトン。 3. Macrocyclic oxalactone represented by the following general formula (3).
〔式中、Rは水素原子又は炭素数1〜3のアルキル基を示し、pは6〜11の整数を示し、qは2〜6の整数を示す。ただし、p+q=10〜14を満たすものとする。〕 [In formula, R shows a hydrogen atom or a C1-C3 alkyl group, p shows the integer of 6-11, q shows the integer of 2-6. However, p + q = 10-14 shall be satisfy | filled. ]
例えば、10-オキサ-16-ヘキサデカノライド(高砂香料工業社製品名;オキサライド)、11-オキサ-16-ヘキサデカノライド(Quest社製品名;ムスクR1)、12-オキサ-16-ヘキサデカノライド(Quest社製品名:セルボライド)が挙げられる。一般式(3)で表される大環状オキサラクトン化合物において、p+qが13であるものが好ましく、特に10-オキサ-16-ヘキサデカノライドが好ましい。 For example, 10-oxa-16-hexadecanolide (product name of Takasago International Corporation; oxalide), 11-oxa-16-hexadecanolide (product name of Quest; musk R1), 12-oxa-16-hexadecane Decanoride (Quest product name: Serboride). In the macrocyclic oxalactone compound represented by the general formula (3), those having p + q of 13 are preferable, and 10-oxa-16-hexadecanolide is particularly preferable.
4.以下に列記するケトン類。
シクロペンタデカノン(Firmenich社製品名;エグザルトン)、3-メチルシクロペンタデカノン(Firmenich社製品名;ムスコン)、3-メチル-4(5)-シクロペンタデセン-1-オン(Firmenich社製品名;ムセノンデルタ)、4-シクロペンタデセン-1-オン(Firmenich社製品名;エギザルテノン、IFF社製品名:ムスクZ-4)、5-シクロヘキサデセン-1-オン(曽田香料社製品名;ムスクTM2)、8-シクロヘキサデセン-1-オン(Symrise社製品名;グロバノン)、9-シクロヘプタデセン-1-オン(Firmenich社製品名;シベトン)、2-ペンチルシクロペンテノン、α-ダマスコン、β-ダマスコン、シス-ジャスモン、2-ヘプチルシクロペンタノン、α-イオノン、β-イオノン、α-メチルイオノン、γ-メチルイオノン、7-メチル-3,4-ジヒドロ-(2H)-1,5-ベンゾジオキセピン-3-オン(Danisco社製品名:カロン)、ヌートカトン、1,2,3,4,5,6,7,8-オクタヒドロ-2,3,8,8-テトラメチル-2-アセトナフトン(IFF社製品名:イソイースーパー)。
4). Ketones listed below.
Cyclopentadecanone (Firmenich product name; Exalton), 3-methylcyclopentadecanone (Firmenich product name; Muscon), 3-methyl-4 (5) -cyclopentadecen-1-one (Firmenich product name) ; Musenon Delta), 4-cyclopentadecen-1-one (Firmenich product name; Egizartenon, IFF product name: Musk Z-4), 5-cyclohexadecene-1-one (Iwata Inc. product name; Musk TM2) , 8-cyclohexadecen-1-one (Symrise product name: Globanone), 9-cycloheptadecen-1-one (Firmenich product name: Sibeton), 2-pentylcyclopentenone, α-damascone, β-damascone , Cis-jasmon, 2-heptylcyclopentanone, α-ionone, β-ionone, α-methylionone, γ-methylionone, 7-methyl-3,4-dihydro- (2H) -1,5-benzodioxepin -3-On (Danisco product name: Caro Nootkaton, 1,2,3,4,5,6,7,8-octahydro-2,3,8,8-tetramethyl-2-acetonaphthone (IFF product name: ISOE Super).
5.以下に列記するエステル類。
4(5)-シクロペンタデセノライド(Firmenich社製品名:ハバノライド)、7-シクロヘキサデセノライド(アンブレットライド)、10-オキサ-16-ヘキサデカノライド(高砂香料工業社製品名;オキサライド)、11-オキサ-16-ヘキサデカノライド(Quest社製品名;ムスクR1)、シトロネリルアセテート、リナリルアセテート、ターピニルアセテート、シンナミルアセテート、シス-3-ヘキセニルベンゾエート、メチル-2-ノニノエート(慣用名:メチルオクチンカーボネート)。
5). Esters listed below.
4 (5) -cyclopentadecenolide (Firmenich product name: havanolide), 7-cyclohexadecenolide (ambretride), 10-oxa-16-hexadecanolide (product name of Takasago International Corporation; Oxalide) ), 11-oxa-16-hexadecanolide (Quest product name: Musk R1), citronellyl acetate, linalyl acetate, terpinyl acetate, cinnamyl acetate, cis-3-hexenylbenzoate, methyl-2-noninoate (Common name: methyl octane carbonate).
6.以下に列記するアルデヒド類。
アニスアルデヒド、シンナミックアルデヒド、クミンアルデヒド、シクラメンアルデヒド、エチルバニリン、2-メチル-3-(3,4-メチレンジオキシフェニル)-プロパナール(IFF社製品名:ヘリオナール)、2-メチル-3-(4-tert-ブチルフェニル)-プロパナール
(Givaudan社製品名;リリアール)、フェニルアセトアルデヒド、3-フェニルプロパナール、バニリン、4-(トリシクロ[5.2.1.02,6]デシリデン-8)ブテナール(IFF社製品名:デュピカール)、ジメチル テトラヒドロベンズアルデヒド(IFF社製品名:トリプラール、Quest社製品名;リグストラール)、4-(4-ヒドロキシ-4-メチルペンチル)-3-シクロヘキセン-1-カルボキシアルデヒド(IFF社製品名:リラール)、4-(4-メチル-3-ペンテニル)-3-シクロヘキセン-1-カルボキシアルデヒド(IFF社製品名:マイラックアルデヒド)、2,6-ノナジエナール、2-メチルウンデカナール、ハイドロキシシトロネラール、シトラール。
6). Aldehydes listed below.
Anisaldehyde, synamic aldehyde, cumin aldehyde, cyclamenaldehyde, ethyl vanillin, 2-methyl-3- (3,4-methylenedioxyphenyl) -propanal (IFF product name: helional), 2-methyl-3- (4-tert-Butylphenyl) -propanal (Givaudan product name; Liliar), phenylacetaldehyde, 3-phenylpropanal, vanillin, 4- (tricyclo [5.2.1.0 2,6 ] decylidene-8) butenal (IFF Company name: Dupicar), dimethyl tetrahydrobenzaldehyde (IFF company name: tripral, Quest product name: Ligstral), 4- (4-hydroxy-4-methylpentyl) -3-cyclohexene-1-carboxaldehyde (IFF company) (Product name: Lyral), 4- (4-Methyl-3-pentenyl) -3-cyclohexene-1-carboxaldehyde (Product name: Mylac Aldehi) ), 2,6-nonadienal, 2-methyl undecanal, hydroxy citronellal, citral.
7.以下に列記するアルコール類。
シトロネロール、ゲラニオール、ネロール、リナロール、リナロールオキサイド、ターピネオール、シンナミックアルコール、オイゲノール、3-メチル-5-フェニル-1-ペンタノール(Firmenich社製品名;フェニルヘキサノール)、ベチベロール。
7). Alcohols listed below.
Citronellol, geraniol, nerol, linalool, linalool oxide, terpineol, cinnamic alcohol, eugenol, 3-methyl-5-phenyl-1-pentanol (Firmenich product name; phenylhexanol), vetiverol.
8.以下に列記するエーテル類。
エストラゴール、6,6,9α-トリメチル-3α-エチルドデカヒドロナフト[2,1-b]フラン(IFF社製品名:グリサルバ)、p-クレジルメチルエーテル、フェニルエチルイソアミルエーテル、1-メトキシシクロドデカン(Symrise社製品名;パリサンディン)、1-メチル-1-メトキシシクロドデカン(Givaudan社製品名;マドロックス)、4,8,12-トリメチル-13-オキサビシクロ[10.1.0]トリデカ-4,8-ジエン(Firmenich社製品名:セドロキサイド)。
8). Ethers listed below.
Estragole, 6,6,9α-trimethyl-3α-ethyldodecahydronaphtho [2,1-b] furan (IFF product name: glycalva), p-cresyl methyl ether, phenylethyl isoamyl ether, 1-methoxycyclo Dodecane (Symrise product name; Paris Sandin), 1-methyl-1-methoxycyclododecane (Givaudan product name; Madrox), 4,8,12-trimethyl-13-oxabicyclo [10.1.0] trideca-4 , 8-Diene (Firmenich product name: Cedroxide).
9.以下に列記するテルペン類。
α-フェランドレン、シトロネリルニトリル。
9. Terpenes listed below.
α-Ferlandolene, citronellylnitrile.
以上のβ-グルクロニダーゼ阻害剤は、動植物から単離したものを用いてもよいし、化学的に合成したものを用いてもよい。また、これらの化合物を含有する精油などの植物抽出物、例えば、ベチバー油、バジル油、クローブ油、シナモン油、グレープフルーツ油等をそのままβ-グルクロニダーゼ阻害剤として用いてもよい。 As the β-glucuronidase inhibitor, those isolated from animals and plants may be used, or those chemically synthesized may be used. In addition, plant extracts such as essential oils containing these compounds, for example, vetiver oil, basil oil, clove oil, cinnamon oil, grapefruit oil and the like may be used as they are as β-glucuronidase inhibitors.
また、グルクロン酸より誘導されるラクトン化合物であるD-グルカロ-1,4-ラクトンや、アセグラトン、D-グルクロン酸、D-ガラクツロン酸等のD-グルカロ-1,4-ラクトン類縁体;リゾホスファチジン酸、リゾホスファチジルコリン、リゾホスファチジルエタノールアミン、リゾホスファチジルグリセロール等のリゾリン脂質;バイカリン等の生薬成分より見出された天然のグルクロニド型阻害剤;タンニン類、カチオン性高分子等のタンパク質吸着剤も本発明のβ-グルクロニダーゼ阻害剤として用いることができる。 In addition, D-glucaro-1,4-lactone, which is a lactone compound derived from glucuronic acid, and D-glucaro-1,4-lactone analogs such as acegraton, D-glucuronic acid, and D-galacturonic acid; lysophosphatidine Lysophospholipids such as acid, lysophosphatidylcholine, lysophosphatidylethanolamine, and lysophosphatidylglycerol; natural glucuronide type inhibitors found from herbal ingredients such as baicalin; and protein adsorbents such as tannins and cationic polymers It can be used as a β-glucuronidase inhibitor.
更には、オウゴン、ゴバイシ、チョウジ、クチナシ、シコン、シャクヤク、エンメイソウ、カミツレ、ツボクサ、コンフリー、アマチャ、カンゾウ、センブリ、冬虫夏草、チンピ、イラクサ、ハマメリス、アケビ等の植物若しくは菌類又はその抽出物も本発明のβ-グルクロニダーゼ阻害剤として用いることができる。 Furthermore, plants or fungi such as urgon, gobishi, clove, gardenia, sicon, peonies, entomons, chamomiles, camellia, comfrey, flax, licorice, embers, cordyceps, chimpi, nettle, hamamelis, akebi, etc. It can be used as a β-glucuronidase inhibitor of the invention.
上記の植物及び菌類は、その植物の全草、葉、根、根茎、果実、種子及び花、並びに菌類のうち1以上をそのまま、又は粉砕して用いることができる。抽出物とする場合は、上記植物若しくは菌類又はその粉砕物を、常温又は加温下にて溶媒抽出することにより得ることができる。抽出に際しては、ソックスレー抽出器等の抽出器具を用いることもできる。 The above plants and fungi can be used as is or after pulverizing one or more of the whole plant, leaves, roots, rhizomes, fruits, seeds and flowers, and fungi of the plants. When it is set as an extract, it can obtain by solvent-extracting the said plant or fungi, or its ground material at normal temperature or a heating. In the extraction, an extraction device such as a Soxhlet extractor can be used.
抽出に用いる溶剤としては水;メタノール、エタノール、プロパノール等のアルコール類;プロピレングリコール、ブチレングリコール等の多価アルコール;アセトン、メチルエチルケトン等のケトン類;酢酸メチル、酢酸エチル等のエステル類;テトラヒドロフラン、ジメチルエーテル等の鎖状及び環状エーテル類;ジクロロメタン、クロロホルム、四塩化炭素等のハロゲン化水素類;ヘキサン、シクロヘキサン、石油エーテル等の炭化水素類;ベンゼン、トルエン等の芳香族炭化水素類;ポリエチレングリコール等のポリエーテル類;ピリジン類などが挙げられ、これらを単独又は混合物として用いることができる。また、二酸化炭素等の超臨界流体を用いることもできる。 Solvents used for extraction are water; alcohols such as methanol, ethanol and propanol; polyhydric alcohols such as propylene glycol and butylene glycol; ketones such as acetone and methyl ethyl ketone; esters such as methyl acetate and ethyl acetate; tetrahydrofuran and dimethyl ether Linear and cyclic ethers such as dichloromethane; hydrogen halides such as dichloromethane, chloroform and carbon tetrachloride; hydrocarbons such as hexane, cyclohexane and petroleum ether; aromatic hydrocarbons such as benzene and toluene; Polyethers; pyridines and the like can be mentioned, and these can be used alone or as a mixture. A supercritical fluid such as carbon dioxide can also be used.
得られた各種溶剤抽出液は、そのままで使用することもでき、その希釈液若しくは濃縮液として、又は濃縮若しくは凍結乾燥した後、粉末状又はペースト状として用いることもできる。また、液々分配等の技術により、上記抽出物から不活性な夾雑物を除去して用いることもでき、本発明においてはこのようなものを用いることが好ましい。これらは必要により公知の方法で脱臭、脱色等の処理を施してから用いてもよい。 The obtained various solvent extracts can be used as they are, and can also be used as a diluted solution or concentrated solution, or after being concentrated or lyophilized, in the form of powder or paste. Moreover, it is also possible to remove inactive impurities from the extract by a technique such as liquid-liquid distribution, and it is preferable to use such a material in the present invention. These may be used after performing treatments such as deodorization and decolorization by a known method, if necessary.
更に、本発明においてβ-グルクロニダーゼ阻害剤は、重量当りの阻害活性が高いものを選択して用いることがより好ましい。具体的には、反応液中0.1重量%の阻害剤が、1.6 units/mLの大腸菌由来β-グルクロニダーゼType VII-Aによるp-ニトロフェニル-β-D-グルクロニド(PNPG)の加水分解反応(400nm吸光度測定によって定量可能)を60%以上抑制するものが好ましく、更には反応中0.01重量%であっても上記反応を80%以上抑制するものがより好ましい。このような阻害剤として一般式(1)から(3)のいずれかで表される大環状化合物が挙げられ、これらを好適に用いることができる。更には一般式(1)で表される大環状ケトンが好ましく、この中でも8-シクロヘキサデセン-1-オン及び9-シクロヘプタデセン-1-オンがより好ましく、価格及び匂いの観点から8-シクロヘキサデセン-1-オンが特に好ましい。
また、以上に記載のβ-グルクロニダーゼ阻害剤は、2種類以上を組み合せて用いてもよい。
Furthermore, in the present invention, it is more preferable to select and use a β-glucuronidase inhibitor having a high inhibitory activity per weight. Specifically, 0.1% by weight of the inhibitor in the reaction solution was subjected to hydrolysis reaction of p-nitrophenyl-β-D-glucuronide (PNPG) with 1.6 units / mL β-glucuronidase Type VII-A derived from E. coli (400 nm It is preferable to suppress 60% or more (which can be quantified by measuring absorbance), and more preferable to suppress the above reaction by 80% or more even when the amount is 0.01% by weight during the reaction. Examples of such inhibitors include macrocyclic compounds represented by any one of the general formulas (1) to (3), and these can be suitably used. Further, a macrocyclic ketone represented by the general formula (1) is preferable, and among these, 8-cyclohexadecene-1-one and 9-cycloheptadecen-1-one are more preferable. Hexadecen-1-one is particularly preferred.
Moreover, the β-glucuronidase inhibitors described above may be used in combination of two or more.
〔界面活性剤〕
本発明の尿臭生成抑制用組成物は、β-グルクロニダーゼ阻害剤とアルキルグリコシド型非イオン界面活性剤を併用することによって、尿臭気の生成に関与する微生物の細胞内β-グルクロニダーゼに対してβ-グルクロニダーゼ阻害効果を向上させる。この効果はアルキルグリコシド型非イオン界面活性剤による殺菌効果発現の有無に依らず得られる。阻害効果向上の詳細な機構は不明であるが、当該界面活性剤が微生物の菌体膜に作用することによってβ-グルクロニダーゼ阻害剤の菌体内への浸透を促進させ、あるいは菌体の膜構造そのものを破壊することによって細胞内β-グルクロニダーゼを外部に露出させ、又は上記以外の何らかの作用若しくはこれらを含む複数の作用により、細胞内β-グルクロニダーゼに対するβ-グルクロニダーゼ阻害剤の効果を向上させる効果を有するものと推測する。
[Surfactant]
The composition for suppressing urine odor production according to the present invention comprises a β-glucuronidase inhibitor and an alkylglycoside-type nonionic surfactant in combination with β for the intracellular β-glucuronidase of microorganisms involved in urine odor production. -Improve glucuronidase inhibitory effect. This effect can be obtained regardless of the presence or absence of the bactericidal effect due to the alkylglycoside type nonionic surfactant. Although the detailed mechanism of the inhibitory effect improvement is unknown, the surfactant acts on the microbial cell membrane to promote the penetration of β-glucuronidase inhibitor into the microbial cell, or the cell membrane structure itself Has an effect of improving the effect of a β-glucuronidase inhibitor on intracellular β-glucuronidase by exposing the intracellular β-glucuronidase to the outside by destroying or by some action other than the above or a plurality of actions including these I guess it.
本発明で使用されるアルキルグリコシド型非イオン界面活性剤としては、下記一般式(Surf-1)で示されるものが挙げられる。 Examples of the alkylglycoside nonionic surfactant used in the present invention include those represented by the following general formula (Surf-1).
R1−(OR2)aGb (Surf-1) R 1 − (OR 2 ) a G b (Surf-1)
〔式中、R1は炭素数8〜16、好ましくは8〜14、より好ましくは8〜12、特に好ましくは10〜12のアルキル基を示し、R2は炭素数2〜4のアルキレン基を示し、好ましくはエチレン基又はプロピレン基、特に好ましくはエチレン基である。Gは還元糖に由来する残基を示し、好ましくはグルコース残基又はガラクトース残基であり、より好ましくはグルコース残基である。aはオキシアルキレン基の平均付加モル数を示す0〜6、特に好ましくは0〜1の数であり、a個のR2は同一でも異なっていても良い。bは還元糖の平均縮合度を示す1〜10、好ましくは1〜5、特に好ましくは1〜2の数である。〕 [Wherein R 1 represents an alkyl group having 8 to 16, preferably 8 to 14, more preferably 8 to 12, and particularly preferably 10 to 12 carbon atoms, and R 2 represents an alkylene group having 2 to 4 carbon atoms. Preferably ethylene group or propylene group, particularly preferably ethylene group. G represents a residue derived from a reducing sugar, preferably a glucose residue or a galactose residue, and more preferably a glucose residue. a is a number of 0 to 6, particularly preferably 0 to 1, which represents the average number of added moles of the oxyalkylene group, and a R 2 s may be the same or different. b is a number of 1 to 10, preferably 1 to 5, particularly preferably 1 or 2, indicating the average degree of condensation of the reducing sugar. ]
本発明の尿臭生成抑制用組成物には、上記のアルキルグリコシド型非イオン界面活性剤に加え、その他の界面活性剤を併用しても構わない。併用できる界面活性剤としては、アルキルグリコシド型非イオン界面活性剤以外の非イオン界面活性剤、両性界面活性剤、カチオン界面活性剤、アニオン界面活性剤が挙げられ、菌への効果の点から、両性界面活性剤、カチオン界面活性剤が好ましく、特にカチオン界面活性剤が好ましい。以下、本発明のアルキルグリコシド型非イオン界面活性剤と併用することが可能な界面活性剤について詳細に述べる。 In addition to the above alkylglycoside type nonionic surfactant, other surfactants may be used in combination with the composition for suppressing urine odor production of the present invention. Examples of surfactants that can be used in combination include nonionic surfactants other than alkylglycoside type nonionic surfactants, amphoteric surfactants, cationic surfactants, and anionic surfactants. Amphoteric surfactants and cationic surfactants are preferred, and cationic surfactants are particularly preferred. Hereinafter, the surfactant that can be used in combination with the alkyl glycoside type nonionic surfactant of the present invention will be described in detail.
・他の非イオン界面活性剤
非イオン界面活性剤としては、下記一般式(Surf-2)で示されるポリオキシアルキレンアルキルエーテル型非イオン界面活性剤、下記一般式(Surf-3)で示されるアミンオキシド型非イオン界面活性剤を挙げることができる。
Other nonionic surfactants Nonionic surfactants include polyoxyalkylene alkyl ether type nonionic surfactants represented by the following general formula (Surf-2), and represented by the following general formula (Surf-3) Mention may be made of amine oxide type nonionic surfactants.
R3−(OR4)c−OH (Surf-2) R 3 − (OR 4 ) c —OH (Surf-2)
〔式中、R3は炭素数8〜16、好ましくは10〜14の炭化水素基を示し、好ましくはアルキル基であり、R4は炭素数2又は3のアルキレン基を示し、好ましくはエチレン基であり、cはオキシアルキレン基の平均付加モル数を示す3〜20の数であり、c個のR4は同一でも異なっていても良い。〕 [Wherein R 3 represents a hydrocarbon group having 8 to 16 carbon atoms, preferably 10 to 14 carbon atoms, preferably an alkyl group, and R 4 represents an alkylene group having 2 or 3 carbon atoms, preferably an ethylene group. And c is a number of 3 to 20 indicating the average number of moles added of the oxyalkylene group, and the c R 4 groups may be the same or different. ]
〔式中、R5は炭素数8〜16、好ましくは10〜16、特に好ましくは10〜14の直鎖アルキル基を示し、R6は炭素数2〜4のアルキレン基を示し、好ましくはエチレン基又はプロピレン基であり、Xは−COO−又は−CONH−を示し、dは0又は1の数を示し、R7及びR8はそれぞれ独立に炭素数1〜3のアルキル基又はヒドロキシアルキル基を示し、好ましくはメチル基である。〕 [In the formula, R 5 represents a linear alkyl group having 8 to 16, preferably 16 to 16, particularly preferably 10 to 14 carbon atoms, R 6 represents an alkylene group having 2 to 4 carbon atoms, preferably ethylene. A group or a propylene group, X represents —COO— or —CONH—, d represents a number of 0 or 1, and R 7 and R 8 each independently represents an alkyl group or a hydroxyalkyl group having 1 to 3 carbon atoms. And preferably a methyl group. ]
・両性界面活性剤
両性界面活性剤としては、スルホベタイン型両性界面活性剤及びカルボベタイン型両性界面活性剤が好適であり、具体的には下記一般式(Surf-4)で示される化合物が好ましい。
-Amphoteric surfactants As amphoteric surfactants, sulfobetaine-type amphoteric surfactants and carbobetaine-type amphoteric surfactants are preferred, and specifically, compounds represented by the following general formula (Surf-4) are preferred. .
〔式中、R9は炭素数8〜16、好ましくは10〜16、特に好ましくは10〜14の直鎖アルキル基を示し、R10は炭素数2〜4のアルキレン基を示し、好ましくはエチレン基又はプロピレン基であり、Yは−COO−又は−CONH−を示し、eは0又は1の数を示し、R11及びR12はそれぞれ独立に炭素数1〜3のアルキル基又はヒドロキシアルキル基を示し、好ましくはメチル基であり、R13はヒドロキシ基で置換されていてもよい炭素数1〜3のアルキレン基を示し。Z-は−SO3 -又は−COO-を示す。〕 [Wherein R 9 represents a linear alkyl group having 8 to 16 carbon atoms, preferably 10 to 16 carbon atoms, particularly preferably 10 to 14 carbon atoms, and R 10 represents an alkylene group having 2 to 4 carbon atoms, preferably ethylene. A group or a propylene group, Y represents —COO— or —CONH—, e represents a number of 0 or 1, and R 11 and R 12 each independently represents an alkyl group or a hydroxyalkyl group having 1 to 3 carbon atoms. And preferably a methyl group, and R 13 represents an alkylene group having 1 to 3 carbon atoms which may be substituted with a hydroxy group. Z − represents —SO 3 — or —COO — . ]
・カチオン界面活性剤
カチオン界面活性剤としては、4級窒素原子に結合する4つの基のうち、1つ又は2つが炭素数8〜12のアルキル基であり、残りが炭素数1〜3のアルキル基若しくはヒドロキシアルキル基、又はベンジル基である4級アンモニウム塩型界面活性剤が好ましい。これら4級アンモニウム塩型界面活性剤の多くは抗菌活性を有する。このようなものとして、ジアルキル(好ましくは共に炭素数10)ジメチルアンモニウム塩や、モノアルキル(好ましくは炭素数12)ベンジルジメチルアンモニウム塩が好ましく、ジアルキル(好ましくは共に炭素数10)ジメチルアンモニウム塩がより好ましい。
-Cationic surfactant As the cationic surfactant, one or two of the four groups bonded to the quaternary nitrogen atom is an alkyl group having 8 to 12 carbon atoms, and the remaining is an alkyl group having 1 to 3 carbon atoms. A quaternary ammonium salt type surfactant which is a group, a hydroxyalkyl group or a benzyl group is preferred. Many of these quaternary ammonium salt type surfactants have antibacterial activity. As such, a dialkyl (preferably both having 10 carbon atoms) dimethylammonium salt or a monoalkyl (preferably 12 carbon atoms) benzyldimethylammonium salt is preferred, and a dialkyl (preferably both having 10 carbon atoms) dimethylammonium salt is more preferred. preferable.
・アニオン界面活性剤
アニオン界面活性剤としては、炭素数10〜18のアルキル基又はアルケニル基を有するアルキルベンゼンスルホン酸塩、ポリオキシアルキレンアルキルエーテル硫酸エステル塩、アルキル硫酸エステル塩、α-オレフィンスルホン酸塩、α-スルホ脂肪酸塩、α-スルホ脂肪酸低級アルキルエステル塩、脂肪酸塩を挙げることができる。
Anionic surfactants Anionic surfactants include alkylbenzene sulfonates, polyoxyalkylene alkyl ether sulfates, alkyl sulfates, α-olefin sulfonates having an alkyl or alkenyl group having 10 to 18 carbon atoms. , Α-sulfo fatty acid salts, α-sulfo fatty acid lower alkyl ester salts, and fatty acid salts.
〔尿臭生成抑制用組成物〕
本発明の尿臭生成抑制用組成物は、β-グルクロニダーゼ阻害剤と0.01〜10重量%のアルキルグリコシド型界面活性剤とを含有するものである。
[Composition for suppressing urine odor production]
The composition for suppressing urine odor production of the present invention comprises a β-glucuronidase inhibitor and 0.01 to 10% by weight of an alkyl glycoside surfactant.
本発明の尿臭生成抑制用組成物におけるβ-グルクロニダーゼ阻害剤の含有量は、0.001〜10重量%となるようにするのが好ましく、更には0.005〜1重量%、更には0.01〜0.5重量%とするのが好ましい。また、本発明の尿臭生成抑制用組成物は尿成分との混合状態においてβ-グルクロニダーゼ阻害剤の濃度が0.0005〜5重量%となるように用いるのが好ましく、更には0.0025〜0.5重量%、更には0.005〜0.25重量%となるように用いるのが好ましい。 The content of the β-glucuronidase inhibitor in the composition for suppressing urine odor production of the present invention is preferably 0.001 to 10% by weight, more preferably 0.005 to 1% by weight, and further 0.01 to 0.5% by weight. Is preferable. In addition, the composition for suppressing urine odor production of the present invention is preferably used so that the concentration of the β-glucuronidase inhibitor is 0.0005 to 5% by weight, more preferably 0.0025 to 0.5% by weight in a mixed state with urine components. Furthermore, it is preferable to use it so that it may become 0.005-0.25weight%.
本発明の尿臭生成抑制用組成物におけるアルキルグリコシド型非イオン界面活性剤の含有量は、細胞内β-グルクロニダーゼに対する阻害効果、尿臭生成抑制効果をより向上させると共に、良好な感触を有するものとする観点より、0.01〜10重量%であり、0.05〜2.5重量%であることが好ましい。また、アルキルグリコシド型非イオン界面活性剤に加え、その他の界面活性剤を併用する場合、本発明の尿臭生成抑制用組成物における界面活性剤の総含有量は、0.01〜10重量%が好ましく、更には0.1〜5重量%が好ましい。
アルキルグリコシド型非イオン界面活性剤とβ-グルクロニターゼ阻害剤の重量比は、500:1〜1:10が好ましく、更には50:1〜1:5、特に10:1〜1:2が好ましい。
The content of the alkylglycoside type nonionic surfactant in the composition for suppressing urine odor production of the present invention improves the inhibitory effect on intracellular β-glucuronidase and the urine odor production inhibitory effect, and has a good feel. In view of the above, it is 0.01 to 10% by weight, and preferably 0.05 to 2.5% by weight. Further, when other surfactants are used in combination with the alkylglycoside type nonionic surfactant, the total content of the surfactant in the composition for suppressing urine odor production of the present invention is preferably 0.01 to 10% by weight. Furthermore, 0.1 to 5% by weight is preferable.
The weight ratio of the alkylglycoside type nonionic surfactant and β-glucuronidase inhibitor is preferably 500: 1 to 1:10, more preferably 50: 1 to 1: 5, and particularly preferably 10: 1 to 1: 2.
(その他)
本発明の尿臭生成抑制用組成物には、更に、例えば抗菌剤、キレート剤、消臭基剤、有機溶剤、油分、アルコール類、pH調整剤、殺菌剤、防腐剤、増粘剤、色素類、香料、保湿剤、柔軟剤、角質保護剤、薬効剤、酸化防止剤、金属塩及び金属イオン類等の成分を、本発明の効果を阻害しない範囲で、任意に配合して製剤化することができる。
(Other)
The composition for suppressing urine odor production of the present invention further includes, for example, antibacterial agents, chelating agents, deodorant bases, organic solvents, oils, alcohols, pH adjusters, bactericides, preservatives, thickeners, dyes. Ingredients such as flavors, fragrances, moisturizers, softeners, keratin protective agents, medicinal agents, antioxidants, metal salts and metal ions are arbitrarily blended to the extent that they do not impair the effects of the present invention. be able to.
・抗菌剤
抗菌剤としては、本発明で用いる界面活性剤の1つであるカチオン界面活性剤以外に、木綿金巾#2003に該化合物1重量%を均一に付着させた布を用い、JIS L 1902「繊維製品の抗菌性試験法」の方法で抗菌性試験を行い、阻止帯が見られる化合物を用いることができる。このような化合物としては「香粧品、医薬品防腐・殺菌剤の科学」(吉村孝一、滝川博文著、フレグランスジャーナル社、1990年4月10日発行)の501頁〜564頁に記載されているものから選択することができる。
Antibacterial agent As the antibacterial agent, in addition to the cationic surfactant which is one of the surfactants used in the present invention, a cloth in which 1% by weight of the compound is uniformly attached to a cotton gold width # 2003 is used. JIS L 1902 An antibacterial test can be performed by the method of “Fiber product antibacterial test method”, and a compound having a blocking band can be used. Such compounds are described in pages 501 to 564 of “Science of cosmetics, pharmaceutical preservatives and fungicides” (by Koichi Yoshimura and Hirofumi Takikawa, published by Fragrance Journal, April 10, 1990). You can choose from.
好ましい抗菌性化合物としては、2-(4-チオシアノメチルチオ)ベンズイミダゾール、ポリリジン、ポリヘキサメチレンビグアニド及びグルクロン酸クロルヘキシジン、トリクロサン、ビス-(2-ピリジルチオ-1-オキシド)亜鉛、2,4,5,6-テトラクロロイソフタロニトリル、トリクロロカルバニリド、8-オキシキノリン、デヒドロ酢酸、安息香酸エステル類、クロロクレゾール類、クロロチモール、クロロフェン、ジクロロフェン、ブロモクロロフェン、ヘキサクロロフェンから選ばれる1種以上を挙げることができ、特にトリクロサンが抗菌効果の点で好ましい。また、特開平11-189975号公報に記載されているトリクロサン類自体も良好であり、具体的にはジクロロヒドロキシジフェニルエーテル、モノクロロヒドロキシジフェニルエーテルが好ましい。また、上記以外の銀、亜鉛等を含有する無機系抗菌剤も用いることができる。これらの抗菌剤は、単独で用いてもよく、2種以上を組み合わせて使うこともできる。 Preferred antibacterial compounds include 2- (4-thiocyanomethylthio) benzimidazole, polylysine, polyhexamethylene biguanide and chlorhexidine glucuronate, triclosan, bis- (2-pyridylthio-1-oxide) zinc, 2,4,5 1,6-tetrachloroisophthalonitrile, trichlorocarbanilide, 8-oxyquinoline, dehydroacetic acid, benzoates, chlorocresols, chlorothymol, chlorophene, dichlorophen, bromochlorophene, hexachlorophene 1 More than one species can be mentioned, and triclosan is particularly preferred from the viewpoint of antibacterial effect. Triclosans described in JP-A-11-189975 are also good, and specifically, dichlorohydroxydiphenyl ether and monochlorohydroxydiphenyl ether are preferable. In addition, inorganic antibacterial agents containing silver, zinc and the like other than those described above can also be used. These antibacterial agents may be used alone or in combination of two or more.
・キレート剤
キレート剤は、特に、本発明の尿臭生成抑制用組成物をトイレに対して用いる場合には、キレート剤によってトイレに付着する燐酸カルシウムなどの無機物質を除去することによって、尿臭生成抑制効果を向上させることができることから、好適に用いることができる。
Chelating agent When the composition for suppressing urine odor production according to the present invention is used for a toilet, the chelating agent removes an inorganic substance such as calcium phosphate adhering to the toilet by the chelating agent, thereby Since the production | generation suppression effect can be improved, it can use suitably.
キレート剤としては、例えば以下に示すような化合物が挙げられる。
(1)フィチン酸などのリン酸系化合物、又はこれらのアルカリ金属塩若しくはアルカノールアミン塩;
(2)エタン-1,1-ジホスホン酸、エタン-1,1,2-トリホスホン酸、エタン-1-ヒドロキシ-1,1-ジホスホン酸、エタンヒドロキシ-1,1,2-トリホスホン酸、エタン-1,2-ジカルボキシ-1,2-ジホスホン酸、メタンヒドロキシホスホン酸などのホスホン酸、又はこれらのアルカリ金属塩若しくはアルカノールアミン塩;
(3)2-ホスホノブタン-1,2-ジカルボン酸、1-ホスホノブタン-2,3,4-トリカルボン酸、α-メチルホスホノコハク酸などのホスホノカルボン酸、又はこれらのアルカリ金属塩若しくはアルカノールアミン塩;
(4)アスパラギン酸、グルタミン酸、グリシンなどのアミノ酸、又はこれらのアルカリ金属塩若しくはアルカノールアミン塩;
(5)ニトリロ三酢酸、イミノ二酢酸、エチレンジアミン四酢酸、ジエチレントリアミン五酢酸、グリコールエーテルジアミン四酢酸、ヒドロキシエチルイミノ二酢酸、トリエチレンテトラミン六酢酸、ジエンコル酸、アルキル(炭素数1〜3)グリシン-N,N-ジ酢酸、アスパラギン酸-N,N-ジ酢酸、セリン-N,N-ジ酢酸、グルタミン酸二酢酸、エチレンジアミンコハク酸などのアミノポリ酢酸、又はこれらの塩、好ましくはアルカリ金属塩、若しくはアルカノールアミン塩;
(6)ジグリコール酸、オキシジコハク酸、カルボキシメチルオキシコハク酸、クエン酸、乳酸、酒石酸、シュウ酸、リンゴ酸、オキシジコハク酸、グルコン酸、カルボキシメチルコハク酸、カルボキメチル酒石酸などの有機酸、又はこれらのアルカリ金属塩、若しくはアルカノールアミン塩;
(7)アミノポリ(メチレンホスホン酸)若しくはそのアルカリ金属塩若しくはアルカノールアミン塩、又はポリエチレンポリアミンポリ(メチレンホスホン酸)若しくはそのアルカリ金属塩若しくはアルカノールアミン塩。
Examples of the chelating agent include the following compounds.
(1) Phosphate compounds such as phytic acid, or alkali metal salts or alkanolamine salts thereof;
(2) Ethane-1,1-diphosphonic acid, ethane-1,1,2-triphosphonic acid, ethane-1-hydroxy-1,1-diphosphonic acid, ethanehydroxy-1,1,2-triphosphonic acid, ethane- Phosphonic acids such as 1,2-dicarboxy-1,2-diphosphonic acid, methanehydroxyphosphonic acid, or alkali metal salts or alkanolamine salts thereof;
(3) Phosphonocarboxylic acids such as 2-phosphonobutane-1,2-dicarboxylic acid, 1-phosphonobutane-2,3,4-tricarboxylic acid, α-methylphosphonosuccinic acid, or alkali metal salts or alkanolamines thereof salt;
(4) amino acids such as aspartic acid, glutamic acid and glycine, or alkali metal salts or alkanolamine salts thereof;
(5) Nitrilotriacetic acid, iminodiacetic acid, ethylenediaminetetraacetic acid, diethylenetriaminepentaacetic acid, glycol etherdiaminetetraacetic acid, hydroxyethyliminodiacetic acid, triethylenetetraminehexaacetic acid, diencoric acid, alkyl (1 to 3 carbon atoms) glycine- Aminopolyacetic acid such as N, N-diacetic acid, aspartic acid-N, N-diacetic acid, serine-N, N-diacetic acid, glutamic acid diacetic acid, ethylenediamine succinic acid, or a salt thereof, preferably an alkali metal salt, or Alkanolamine salts;
(6) Organic acids such as diglycolic acid, oxydisuccinic acid, carboxymethyloxysuccinic acid, citric acid, lactic acid, tartaric acid, oxalic acid, malic acid, oxydisuccinic acid, gluconic acid, carboxymethylsuccinic acid, carboxymethyltartaric acid, or these Alkali metal salts or alkanolamine salts of
(7) Aminopoly (methylenephosphonic acid) or an alkali metal salt or alkanolamine salt thereof, or polyethylenepolyaminepoly (methylenephosphonic acid) or an alkali metal salt or alkanolamine salt thereof.
これらの中で、上記(2)、(5)及び(6)からなる群より選ばれる少なくとも1種が好ましく、上記(5)及び(6)からなる群より選ばれる少なくとも1種が更に好ましい。最も好ましい成分は、エチレンジアミン四酢酸、メチルグリシン-N,N-ジ酢酸、クエン酸である。これらのキレート剤は、単独で用いてもよく、2種以上を組み合わせて使うこともできる。 Among these, at least one selected from the group consisting of (2), (5) and (6) is preferable, and at least one selected from the group consisting of (5) and (6) is more preferable. The most preferred components are ethylenediaminetetraacetic acid, methylglycine-N, N-diacetic acid and citric acid. These chelating agents may be used alone or in combination of two or more.
・消臭基剤
消臭基剤の例としては、
酸化鉄、硫酸鉄、塩化鉄、酸化亜鉛、硫酸亜鉛、塩化亜鉛、酸化銀、酸化銅等の金属化合物;
リン酸、クエン酸、コハク酸等の酸と、トリエタノールアミン、モノエタノールアミン、水酸化ナトリウム、水酸化カリウム、2-アミノ-2-ヒドロキシメチル-1,3-プロパンジオール(トリス(ヒドロキシメチル)アミノメタン)等の塩基との組み合わせからなるpH緩衝効果を有する酸ないしはその塩;
乳酸、コハク酸、リンゴ酸、クエン酸、マレイン酸、マロン酸等のカルボン酸類;
ウンデシレン酸亜鉛、2-エチルヘキサン酸亜鉛、リシノール亜鉛などの脂肪酸金属類;
カテキン、ポリフェノール、緑茶抽出物、マッシュルームエキス、木酢液、竹酢液等の植物抽出物系の消臭剤;
鉄、銅などの金属クロロフィリンナトリウム,鉄、銅、コバルトなどの金属フタロシアニン,鉄、銅、コバルト等のテトラスルホン酸フタロシアニン,二酸化チタン、可視光応答型二酸化チタン(窒素ドープ型など)などの触媒型消臭剤;
α-、β-、又はγ-シクロデキストリン、そのメチル誘導体、ヒドロキシプロピル誘導体、グルコシル誘導体、マルトシル誘導体等のシクロデキストリン類;
エチレングリコール、プロピレングリコール、ジエチレングリコール、ジプロピレングリコール等の悪臭の保留効果があるとされるアルキレングリコール類;
ミリスチン酸エステル類、パルミチン酸エステル類、フタル酸エステル類、アジピン酸エステル類、セバシン酸エステル類、クエン酸エステル類等の悪臭の保留効果があるとされるエステル油剤;
多孔メタクリル酸ポリマー、多孔アクリル酸ポリマー等のアクリル酸系ポリマー、多孔ジビニルベンゼンポリマー、多孔スチレン−ジビニルベンゼン−ビニルピリジンポリマー、多孔ジビニルベンゼン−ビニルピリジンポリマー等の芳香族系ポリマー、それらの共重合体等の合成の多孔質ポリマー;キチン、キトサン等の天然の多孔質ポリマー;
活性炭、シリカ、二酸化ケイ素(シリカゲル)、ケイ酸カルシウム、ハイシリカゼオライト(疎水性ゼオライト)、セピオライト、カンクリナイト、ゼオライト、水和酸化ジルコニウム等の無機多孔質物質;
銀担持ゼオライト、銀担持カンクリナイト、銀担持多孔スチレン−ジビニルベンゼン−ビニルピリジンポリマー等の金属担持多孔質
等が挙げられる。これらの消臭基剤は、単独で用いてもよく、2種以上を組み合わせて使うこともできる。
・ Deodorant base Examples of deodorant base include
Metal compounds such as iron oxide, iron sulfate, iron chloride, zinc oxide, zinc sulfate, zinc chloride, silver oxide, copper oxide;
Acids such as phosphoric acid, citric acid and succinic acid, and triethanolamine, monoethanolamine, sodium hydroxide, potassium hydroxide, 2-amino-2-hydroxymethyl-1,3-propanediol (tris (hydroxymethyl) An acid or a salt thereof having a pH buffering effect comprising a combination with a base such as aminomethane);
Carboxylic acids such as lactic acid, succinic acid, malic acid, citric acid, maleic acid, malonic acid;
Fatty acid metals such as zinc undecylenate, zinc 2-ethylhexanoate, zinc ricinol;
Plant extract-type deodorants such as catechin, polyphenol, green tea extract, mushroom extract, wood vinegar and bamboo vinegar
Metal type chlorophyllin sodium such as iron and copper, metal phthalocyanine such as iron, copper and cobalt, catalyst type such as tetraphthalic acid phthalocyanine such as iron, copper and cobalt, titanium dioxide, visible light responsive titanium dioxide (nitrogen doped type, etc.) Deodorants;
cyclodextrins such as α-, β-, or γ-cyclodextrin, its methyl derivatives, hydroxypropyl derivatives, glucosyl derivatives, maltosyl derivatives;
Alkylene glycols that are said to have a retention of malodor such as ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol;
Ester oil agent that is said to have an effect of retaining bad odor such as myristic acid esters, palmitic acid esters, phthalic acid esters, adipic acid esters, sebacic acid esters, citrate esters;
Acrylic acid polymer such as porous methacrylic acid polymer and porous acrylic acid polymer, porous divinylbenzene polymer, porous styrene-divinylbenzene-vinylpyridine polymer, aromatic polymer such as porous divinylbenzene-vinylpyridine polymer, and copolymers thereof Synthetic porous polymers such as chitin, chitosan and other natural porous polymers;
Inorganic porous materials such as activated carbon, silica, silicon dioxide (silica gel), calcium silicate, high silica zeolite (hydrophobic zeolite), sepiolite, cancrinite, zeolite, hydrated zirconium oxide;
Examples thereof include metal-supporting porous materials such as silver-supporting zeolite, silver-supporting cancrinite, and silver-supporting porous styrene-divinylbenzene-vinylpyridine polymer. These deodorant bases may be used alone or in combination of two or more.
・有機溶剤
有機溶剤としては、水溶性の有機溶剤が好ましく、例えば、
エタノール、1-プロパノール、2-プロパノール、ブチルアルコール等のアルコール類;
エチレングリコール、1,2-プロパンジオール、1,3-ブタンジオール、ヘキシレングリコール、2-エチル-1,3-ヘキサンジオール、グリセリン、トリエチレングリコール、ジプロピレングリコール、ジグリセリン、ポリエチレングリコール、ポリプロピレングリコール等の多価アルコール類;
エチレングリコールエチルエーテル、エチレングリコールメチルエーテル、エチレングリコールブチルエーテル、ジエチレングリコールエチルエーテル等のエーテル類
等が挙げられる。これらの有機溶剤は、単独で用いてもよく、2種以上を組み合わせて使うこともできる。
Organic solvent As the organic solvent, a water-soluble organic solvent is preferable, for example,
Alcohols such as ethanol, 1-propanol, 2-propanol, butyl alcohol;
Ethylene glycol, 1,2-propanediol, 1,3-butanediol, hexylene glycol, 2-ethyl-1,3-hexanediol, glycerin, triethylene glycol, dipropylene glycol, diglycerin, polyethylene glycol, polypropylene glycol Polyhydric alcohols such as
And ethers such as ethylene glycol ethyl ether, ethylene glycol methyl ether, ethylene glycol butyl ether, and diethylene glycol ethyl ether. These organic solvents may be used alone or in combination of two or more.
〔尿臭生成抑制方法、製品形態〕
本発明の尿臭生成抑制用組成物を、家庭用及び施設用などの製品中に有効量含有させ、あるいはそのまま用いることにより、尿に由来する悪臭の生成に対し高い抑制効果、防臭効果を奏することができる。また、本発明の尿臭生成抑制用組成物を、対象物(尿臭の発生を抑制しようとする物)に、尿が付着する前又は尿が付着してから付着した尿が乾燥する前に、好ましくは尿が付着してから1時間以内、更に好ましくは10分以内に適用することにより、尿臭の生成を効果的に抑制することができる。
[Urine odor production suppression method, product form]
By containing an effective amount of the composition for suppressing urine odor production of the present invention in products for household use and facilities, or using it as it is, it exhibits a high inhibitory effect and deodorizing effect on the production of malodor derived from urine. be able to. In addition, the composition for suppressing urine odor production according to the present invention is applied to an object (an object for which generation of urine odor is to be suppressed) before urine adheres or after the urine adhering to the urine is dried. The production of urine odor can be effectively suppressed by applying within 1 hour, more preferably within 10 minutes, preferably after urine adheres.
上記尿とは、ヒト由来のものに限定されるものではなく、犬や猫を代表とするペット等の動物由来の尿であっても良い。また、上記の尿に由来する悪臭とは、尿単独から発生する悪臭に限定されるものではなく、例えばオムツ内などにおいて尿と便が混合された状態から発生する悪臭であってもよい。 The urine is not limited to those derived from humans, and may be urine derived from animals such as pets such as dogs and cats. The malodor derived from urine is not limited to the malodor generated from urine alone, and may be a malodor generated from a state in which urine and feces are mixed in a diaper, for example.
本発明の尿臭生成抑制用組成物によって制御可能な悪臭成分は、フェノール系化合物及びインドール類であり、具体的にはフェノール、p-クレゾール、4-ビニル-2-メトキシ-フェノール、4-ビニルフェノール、2-メトキシ-1,3-ベンゼンジオール、1,4-ベンゼンジオール、1,3-ベンゼンジオール、インドール等が挙げられるが、これに限定されず、尿にβ-グルクロニダーゼが作用することによって生じる揮発性成分であればよい。 The malodorous components that can be controlled by the composition for suppressing urine odor production of the present invention are phenolic compounds and indoles, specifically phenol, p-cresol, 4-vinyl-2-methoxy-phenol, 4-vinyl. Examples include phenol, 2-methoxy-1,3-benzenediol, 1,4-benzenediol, 1,3-benzenediol, and indole, but are not limited to this, and β-glucuronidase acts on urine. Any volatile component may be generated.
(製品形態)
製品形態としては、吐出型製品、塗布製品、拭き取り製品等の対象物に直接本発明の尿臭生成抑制用組成物を適用して付着させる製品、又は尿が回収される部分に本発明の尿臭生成抑制用組成物を保持させる吸収性製品を挙げることができる。
(Product form)
As a product form, a product to which the composition for suppressing urine odor production of the present invention is applied directly to an object such as a discharge-type product, a coated product, a wiping product, or the urine of the present invention at a portion where urine is collected. An absorptive product that holds the composition for suppressing odor generation can be mentioned.
吐出型製品は、トリガー式スプレーヤーを備える容器、ボタン式スプレー容器、エアゾール容器、スクイズ容器等の霧状又は泡状に吐出する吐出装置を備える容器、又は滴下型製品用容器に本発明の尿臭生成抑制用組成物を収容し、吐出装置によって対象物に適用する製品である。このうち、トリガー式又はボタン式スプレーの吐出装置を用いた製品が好ましい。滴下による吐出型製品としては、トイレのタンク上、又は便器内に設置されて、トイレの便器内に流れて適用されるものも含まれる。
吐出型製品とする場合、用いられる尿臭生成抑制用組成物における水の含有量は、好ましくは50〜99重量%、より好ましくは70〜98重量%、更に好ましくは80〜95重量%である。また、吐出型製品に収容された尿臭生成抑制用組成物の20℃におけるpHは、好ましくは5〜9、より好ましくは6〜8であり、pH調整は通常用いられるpH調整剤で行われる。
The discharge type product is a container having a trigger sprayer, a button type spray container, an aerosol container, a squeeze container or the like, a container having a discharge device for discharging in a mist or foam form, or a container for a drop type product. It is a product that contains a composition for suppressing odor generation and is applied to an object by a discharge device. Among these, a product using a trigger type or button type spray discharge device is preferable. The discharge-type product by dripping includes a product installed on a toilet tank or in a toilet bowl and applied by flowing into the toilet toilet bowl.
In the case of a discharge-type product, the water content in the composition for suppressing urine odor production is preferably 50 to 99% by weight, more preferably 70 to 98% by weight, and still more preferably 80 to 95% by weight. . Moreover, the pH at 20 ° C. of the composition for suppressing urine odor production contained in the discharge-type product is preferably 5 to 9, more preferably 6 to 8, and pH adjustment is performed with a commonly used pH adjuster. .
塗布製品又は拭き取り製品は、多孔質部材又はシート材等の保持部材に本発明の尿臭生成抑制用組成物を含浸、又は保持させて対象物に塗布する製品であって、シート材に含浸させたシート製品が好ましい。 A coated product or a wiped product is a product that is applied to an object by impregnating or holding the composition for suppressing urine odor production of the present invention on a holding member such as a porous member or sheet material, and impregnating the sheet material. Sheet products are preferred.
吸収性製品は、尿等の排泄物が直接吸収される物品に、本発明の尿臭生成抑制用組成物を含浸又は保持させ、吸収された尿による尿臭生成を抑制する。吸収性製品においては、本発明の尿臭生成抑制用組成物がヒトの肌に直接ふれないが、吸収された尿に接触可能なものが好ましく、例えば、多層構造になったシート製品の中間層に用いられる吸水性ポリマー、パルプ、不織布及び/又は台紙に本発明の尿臭生成抑制用組成物を含浸又は保持させたものを挙げることができる。この中でも吸水性ポリマー及び/又はパルプに本発明の尿臭生成抑制用組成物を含浸又は保持させたものがより好ましく、更には吸水性ポリマーに含浸又は保持させたものが特に好ましい。 The absorbent product impregnates or holds the composition for suppressing urine odor production of the present invention in an article in which excrement such as urine is directly absorbed, thereby suppressing urine odor production by the absorbed urine. In the absorbent product, the composition for suppressing urine odor production of the present invention does not directly touch human skin, but is preferably capable of coming into contact with absorbed urine, for example, an intermediate layer of a sheet product having a multilayer structure. The water-absorbing polymer, pulp, non-woven fabric and / or backing paper used in the present invention are impregnated or retained with the composition for suppressing urine odor production of the present invention. Among these, a water-absorbing polymer and / or pulp impregnated or retained with the composition for suppressing urine odor production of the present invention is more preferable, and a water-absorbing polymer impregnated or retained is particularly preferable.
下記の参考例及び実施例では、除菌用のフィルターとして0.2μmのフィルター(ミリポア社製、マイレックスGV、又はナルゲン社製のフィルターユニット)を用いた。また、特記しない限りβ-グルクロニダーゼは、大腸菌由来のβ-グルクロニダーゼType VII-A(シグマ社より購入)を使用した。また、吸光度測定には吸光マイクロプレートリーダー(TECAN社製、サンライズレインボーサーモRC)を使用し、各波長におけるサンプルの吸光度は96穴マイクロウェルプレート(NUNC社製、Nunclon Delta Surface)のウェル中でのサンプル200μLに対する測定値を使用した。 In the following Reference Examples and Examples, a 0.2 μm filter (a filter unit manufactured by Millipore, Milex GV, or Nalgen) was used as a filter for sterilization. Unless otherwise specified, β-glucuronidase Type VII-A (purchased from Sigma) derived from E. coli was used as β-glucuronidase. In addition, an absorbance microplate reader (TECAN, Sunrise Rainbow Thermo RC) was used for absorbance measurement, and the absorbance of the sample at each wavelength was measured in a well of a 96-well microwell plate (NUNC, Nunclon Delta Surface). Measurements for 200 μL of sample were used.
参考例1 β-グルクロニダーゼ添加による尿からの揮発性化合物の生成
(1) 測定サンプルの調製
γ線滅菌済み容器中に、採取後すぐに0.2μmのフィルターにて除菌操作を行ったヒト尿サンプル(5人のヒト尿混合物)9.9mLを入れ、続いて250units/mLに調整したβ-グルクロニダーゼType VII-A水溶液0.1mLを添加混合し、25℃恒温槽に静置して22時間反応させた。酵素液の代わりに滅菌イオン交換水0.1mLを添加したものを初期尿サンプルとして同様に22時間恒温槽中に静置した。
反応終了後、反応液9mLに内部標準としてベンジルベンゾエート エタノール溶液を添加し、ジエチルエーテル10mLを用いて2回抽出を行った。抽出液は合わせて無水硫酸マグネシウムで乾燥を行った。乾燥後、固形物をろ別し、ろ液をロータリーエバポレーターで濃縮して測定サンプルとした。
Reference Example 1 Production of volatile compounds from urine by addition of β-glucuronidase
(1) Preparation of measurement sample In a γ-ray sterilized container, immediately after collection, 9.9 mL of a human urine sample (mixture of 5 human urine) that was sterilized with a 0.2 μm filter was placed, followed by 250 units. β-glucuronidase Type VII-A aqueous solution adjusted to 0.1 mL / mL was added and mixed, and the mixture was allowed to stand in a thermostatic bath at 25 ° C. and reacted for 22 hours. What added 0.1 mL of sterilized ion-exchange water instead of the enzyme solution was similarly left as an initial urine sample in a thermostat for 22 hours.
After completion of the reaction, benzyl benzoate ethanol solution was added as an internal standard to 9 mL of the reaction solution, and extracted twice with 10 mL of diethyl ether. The extracts were combined and dried over anhydrous magnesium sulfate. After drying, the solid matter was filtered off, and the filtrate was concentrated with a rotary evaporator to obtain a measurement sample.
(2) 揮発性化合物の測定
測定にはガスクロマトグラフ質量分析計を用いた。検出された揮発性化合物の生成量は内部標準に対するピークエリア比として算出した。この結果を表1に示す。
(2) Measurement of volatile compounds A gas chromatograph mass spectrometer was used for measurement. The production amount of the detected volatile compound was calculated as a peak area ratio with respect to the internal standard. The results are shown in Table 1.
この結果より、β-グルクロニダーゼの作用により尿から種々のフェノール系化合物及びインドールが生成することが確認された。 From these results, it was confirmed that various phenolic compounds and indole were produced from urine by the action of β-glucuronidase.
参考例2 特定化合物及び植物抽出物によるβ-グルクロニダーゼの活性阻害
γ線滅菌済み容器中にて2mM PNPG水溶液100μL、0.5Mリン酸緩衝液(pH6.8)40μL、イオン交換水38μL、各種化合物又は植物抽出物の10又は1重量%ジプロピレングリコール(DPG)溶液2μLを混合し、続いて16units/mLに調整したβ-グルクロニダーゼ水溶液20μLを加えて37℃恒温槽中で2時間酵素反応を行った。また一部の化合物については、更に0.1重量%DPG溶液についても同様の実験を行った。供した化合物及び植物抽出物の反応液中での濃度はそれぞれ、0.1、0.01、0.001重量%となる。また、上記化合物及び植物抽出物の代わりにDPGを加えたものをコントロールとし、各サンプル及びコントロールごとに酵素液の代わりにイオン交換水を加えたものをブランクとして、それぞれ同様に2時間反応を行った。
上記反応液を0.2Mグリシン-水酸化ナトリウム緩衝液(pH10.4)を用いて希釈し、波長400nmにおける吸光度を測定した。得られた測定値より、次式に従ってβ-グルクロニダーゼの相対活性阻害率を求め、表2a及び表2bに示した。
Reference Example 2 Inhibition of β-glucuronidase activity by specific compounds and plant extracts 100 μL of 2 mM PNPG aqueous solution, 40 μL of 0.5 M phosphate buffer (pH 6.8), 38 μL of ion exchange water, various compounds or 2 μL of 10 or 1 wt% dipropylene glycol (DPG) solution of plant extract was mixed, followed by addition of 20 μL of β-glucuronidase aqueous solution adjusted to 16 units / mL, and the enzyme reaction was performed in a 37 ° C. constant temperature bath for 2 hours. . For some compounds, the same experiment was conducted for a 0.1 wt% DPG solution. The concentrations of the supplied compound and plant extract in the reaction solution are 0.1, 0.01, and 0.001% by weight, respectively. In addition, the reaction was performed in the same manner for 2 hours using the above compound and plant extract with DPG added as a control, and each sample and control with ion exchange water added in place of the enzyme solution as a blank. It was.
The reaction solution was diluted with 0.2 M glycine-sodium hydroxide buffer (pH 10.4), and the absorbance at a wavelength of 400 nm was measured. From the obtained measured values, the relative activity inhibition rate of β-glucuronidase was determined according to the following formula, and is shown in Table 2a and Table 2b.
この結果より、供した化合物及び植物抽出物サンプルはβ-グルクロニダーゼ阻害活性を有することがわかる。 From this result, it can be seen that the provided compound and plant extract sample have β-glucuronidase inhibitory activity.
参考例3 β-グルクロニダーゼ阻害剤による尿由来揮発性化合物の生成抑制
(1) サンプルの調製
γ線滅菌済み容器中に、採取後すぐに0.2μmのフィルターにて除菌操作を行ったヒト尿サンプル9.9mL(5人のヒト尿の混合物)、10重量% 8-シクロヘキサデセン-1-オンDPG溶液10μLを加え、続いて250units/mLに調整したβ-グルクロニダーゼ水溶液 0.1mLを添加混合し、25℃恒温槽に静置して22時間反応させた。8-シクロヘキサデセン-1-オンの反応液中での濃度は0.01重量%となる。また、除菌尿サンプル9.9mLに酵素液 0.1mLを加えたものをコントロール、除菌尿サンプル9.9mLにイオン交換水0.1mLを加えたものをブランクとして、それぞれ同様に22時間反応させた。
反応終了後、反応液9mLに内部標準としてベンジルベンゾエート エタノール溶液を添加し、ジエチルエーテル10mLを用いて2回抽出を行った。抽出液は合わせて無水硫酸マグネシウムで乾燥を行った。乾燥後、固形物をろ別し、ろ液をロータリーエバポレーターで濃縮して測定サンプルとした。
Reference Example 3 Suppression of urine-derived volatile compounds by β-glucuronidase inhibitors
(1) Preparation of sample 9.9 mL of human urine sample (mixture of 5 human urine), 10% by weight 8- 10 μL of cyclohexadecen-1-one DPG solution was added, and then 0.1 mL of a β-glucuronidase aqueous solution adjusted to 250 units / mL was added and mixed, and the mixture was allowed to stand in a 25 ° C. constant temperature bath and reacted for 22 hours. The concentration of 8-cyclohexadecen-1-one in the reaction solution is 0.01% by weight. In addition, each of 9.9 mL of sterilized urine sample was added with 0.1 mL of enzyme solution as a control, and 9.9 mL of sterilized urine sample added with 0.1 mL of ion-exchanged water was used as a blank, and reacted for 22 hours in the same manner.
After completion of the reaction, benzyl benzoate ethanol solution was added as an internal standard to 9 mL of the reaction solution, and extracted twice with 10 mL of diethyl ether. The extracts were combined and dried over anhydrous magnesium sulfate. After drying, the solid matter was filtered off, and the filtrate was concentrated with a rotary evaporator to obtain a measurement sample.
(2) 揮発性化合物の生成抑制
測定にはガスクロマトグラフ質量分析計を用いた。検出された揮発性化合物の生成量は内部標準に対するピークエリア比として算出した。得られた値より、次式に従って揮発性成分ごとの生成抑制率を求め、表3に示した。
(2) Inhibition of volatile compound formation A gas chromatograph mass spectrometer was used for measurement. The production amount of the detected volatile compound was calculated as a peak area ratio with respect to the internal standard. From the obtained value, the production inhibition rate for each volatile component was determined according to the following formula and shown in Table 3.
この結果より、β-グルクロニダーゼの作用により尿より生成するフェノール系化合物及びインドールの全てについて、β-グルクロニダーゼ阻害剤(8-シクロヘキサデセン-1-オン)がその生成を抑制したことがわかる。 From this result, it can be seen that the β-glucuronidase inhibitor (8-cyclohexadecen-1-one) suppressed the production of all phenolic compounds and indoles produced from urine by the action of β-glucuronidase.
実施例1-1〜1-4、比較例1-1〜1-3 β-グルクロニダーゼ阻害剤と界面活性剤の併用による阻害効果の向上
(1)尿臭産生菌の採取
3名のパネラー宅のトイレ便器フチ裏からβ-グルクロニダーゼ活性検出試薬(5-ブロモ-4-クロロ-3-インドリル-β-D-グルクロニド)を添加したSCDLP寒天平板培地(日本製薬株式会社製)を用いてβ-グルクロニダーゼ活性菌の採取、分離を行った。これら菌株を除菌尿中で培養したところ臭気の発生が確認され、この中でも特に強い臭気を発生させた菌株を本実施例における尿臭産生菌として用いた。また本菌株は16S rDNA部分塩基配列解析によって大腸菌に帰属されるものであることを確認した。
Examples 1-1 to 1-4, Comparative Examples 1-1 to 1-3 Improvement of inhibitory effect by combined use of β-glucuronidase inhibitor and surfactant (1) Collection of urine odor producing bacteria Three panelists' homes Β-glucuronidase using SCDLP agar plate medium (manufactured by Nippon Pharmaceutical Co., Ltd.) supplemented with β-glucuronidase activity detection reagent (5-bromo-4-chloro-3-indolyl-β-D-glucuronide) from the back of toilet toilet Active bacteria were collected and separated. Occurrence of odor was confirmed when these strains were cultured in sterilized urine. Among them, a strain that generated particularly strong odor was used as a urine odor producing bacterium in this example. This strain was confirmed to be attributed to E. coli by 16S rDNA partial nucleotide sequence analysis.
(2)菌液の調製
上記の尿臭産生菌を3mMのPNPGを含むミュラーヒントン培地で培養し、遠心操作によって液部を除いた。残った菌体部分を生理食塩水に懸濁させ、再度、遠心操作によって液部を除き、この操作を2度行うことによって菌体部分の洗浄を行った。これをD-PBS(Dulbecco’s Phosphate Buffered Saline)を用いて適宜希釈し、波長600nmにおける吸光度が0.4となるように調整した。
(2) Preparation of Bacterial Solution The above urine odor producing bacteria were cultured in Mueller Hinton medium containing 3 mM PNPG, and the liquid part was removed by centrifugation. The remaining bacterial cell part was suspended in physiological saline, the liquid part was removed again by centrifugation, and this operation was performed twice to wash the bacterial cell part. This was appropriately diluted with D-PBS (Dulbecco's Phosphate Buffered Saline) and adjusted so that the absorbance at a wavelength of 600 nm was 0.4.
(3)尿臭産生菌細胞内β-グルクロニダーゼ活性の抑制効果測定
2mMのPNPGを含む200mM リン酸緩衝液(pH6.8)200μLに、実施例1-1〜1-4としてアルキルグリコシド型非イオン界面活性剤、比較例1-1としてポリオキシエチレンソルビタン脂肪酸エステル型非イオン界面活性剤、比較例1-2及び1-3として水溶性有機溶剤の各1w/v%水溶液を40μL添加混合し、1w/v%β-グルクロニダーゼ阻害剤(8-シクロヘキサデセン-1-オン)エタノール溶液を4μL添加混合して、更にイオン交換水を加えて380μLとした。また、比較例1-4(阻害剤のみ)として2mMのPNPGを含む200mM リン酸緩衝液(pH6.8)200μLに1w/v%β-グルクロニダーゼ阻害剤エタノール溶液を4μL添加混合して、更にイオン交換水を加えて380μLとした溶液を調製した。
これら溶液に対して本実施例(2)で調製した尿臭産生菌菌液20μLを添加混合し、37℃恒温槽中で1時間反応させた。反応液中での濃度はそれぞれ、β-グルクロニダーゼ阻害剤は0.01w/v%、界面活性剤及び水溶性有機溶剤は0.1w/v%又は「なし」(比較例1-4)となる。また、比較例1-4の組成について阻害剤溶液に代えてエタノールを添加混合したものをコントロールとして同様に反応を行った。更に、コントロールの組成について菌液をD-PBSに換えて同様の操作を行ったものをブランクとした。
反応終了後、反応液の一部を0.2Mグリシン-水酸化ナトリウム緩衝液(pH10.4)を用いて希釈し、10000rpmで2分間遠心操作を行い、遠心後の上清を用いて波長400nmにおける吸光度を測定した。得られた測定値より、次式に従って各サンプルにおける尿臭産生菌細胞内β-グルクロニダーゼの相対活性を求め、結果を表4に示した。
(3) Inhibitory effect measurement of β-glucuronidase activity in urine odor producing bacteria Into 200 μL of 200 mM phosphate buffer (pH 6.8) containing 2 mM PNPG, alkylglycoside type nonion as Examples 1-1 to 1-4 40 μL of a surfactant, a polyoxyethylene sorbitan fatty acid ester type nonionic surfactant as Comparative Example 1-1, and each 1 w / v% aqueous solution of a water-soluble organic solvent as Comparative Examples 1-2 and 1-3 were added and mixed. 4 μL of 1 w / v% β-glucuronidase inhibitor (8-cyclohexadecen-1-one) ethanol solution was added and mixed, and ion-exchanged water was further added to make 380 μL. Further, as Comparative Example 1-4 (inhibitor only), 200 μL of 200 mM phosphate buffer (pH 6.8) containing 2 mM PNPG was added and mixed with 4 μL of 1 w / v% β-glucuronidase inhibitor ethanol solution, and further ionized. A solution was prepared by adding exchange water to 380 μL.
20 μL of the urine odor producing bacterial solution prepared in this Example (2) was added to and mixed with these solutions and reacted in a 37 ° C. constant temperature bath for 1 hour. The concentrations in the reaction solution are 0.01 w / v% for the β-glucuronidase inhibitor, 0.1 w / v% for the surfactant and the water-soluble organic solvent, or “none” (Comparative Example 1-4). In addition, the composition of Comparative Example 1-4 was reacted in the same manner using as a control a mixture obtained by adding ethanol instead of the inhibitor solution. Furthermore, the control composition was changed to D-PBS and the same operation was performed to obtain a blank.
After completion of the reaction, a part of the reaction solution is diluted with 0.2 M glycine-sodium hydroxide buffer (pH 10.4), centrifuged at 10,000 rpm for 2 minutes, and the centrifuged supernatant is used at a wavelength of 400 nm. Absorbance was measured. From the obtained measured values, the relative activity of β-glucuronidase in urine odor producing bacteria in each sample was determined according to the following formula, and the results are shown in Table 4.
また、アルキルグリコシド型非イオン界面活性剤については、更に低濃度の領域についても評価を行うため、1w/v%水溶液の添加量を1/20(2μL)として同様の測定を行い、結果を表4に示した。なお、このとき反応液中での濃度はそれぞれ、β-グルクロニダーゼ阻害剤は0.01w/v%、活性剤は0.005w/v%となる。 In addition, for alkylglycoside type nonionic surfactants, in order to evaluate even lower concentrations, the same measurement was performed with the addition amount of 1 w / v% aqueous solution being 1/20 (2 μL), and the results are shown. This is shown in FIG. At this time, the concentrations in the reaction solution are 0.01 w / v% for the β-glucuronidase inhibitor and 0.005 w / v% for the active agent, respectively.
<添加成分>
ドデシルグルコシド:花王(株)製、マイドール12を使用
デシルグルコシド:花王(株)製、マイドール10を使用
イソデシルガラクトシド:特開2008-156271号公報に記載の手法に従い合成したものを使用
オクチルガラクトシド:特開2008-156271号公報に記載の手法に従い合成したものを使用
ポリオキシエチレンソルビタンモノオレエート:花王(株)製、レオドールスーパーTW-O120を使用
グリセロール:片山化学工業(株)より購入したものを使用
プロピレングリコール:旭硝子(株)より購入したものを使用
<Additive components>
Dodecyl glucoside: manufactured by Kao Corporation, using Mydol 12 Decyl glucoside: manufactured by Kao Corporation, using
以上の結果に示したとおり、アルキルグリコシド型非イオン界面活性剤はβ-グルクロニダーゼ阻害剤との併用により、阻害効果を向上させた。特に実施例1-1及び1-2に挙げたアルキルグルコシドは添加量を1/20とした場合(0.005w/v%)においても良好な阻害効果を発揮した。このような効果は他の非イオン界面活性剤であるポリオキシエチレンソルビタンモノオレエート及び一般の水溶性有機溶剤の添加では得られなかった。すなわち、酵素活性阻害効果の向上はアルキルグリコシド型非イオン界面活性剤の併用による特有の効果であり、単にβ‐グルクロニダーゼ阻害剤の水溶液中への可溶化能を向上させただけでは酵素活性阻害効果を向上しなかった。 As shown in the above results, the alkylglycoside type nonionic surfactant improved the inhibitory effect when used in combination with the β-glucuronidase inhibitor. In particular, the alkyl glucosides listed in Examples 1-1 and 1-2 exhibited a good inhibitory effect even when the addition amount was 1/20 (0.005 w / v%). Such an effect could not be obtained by adding other nonionic surfactants such as polyoxyethylene sorbitan monooleate and general water-soluble organic solvents. In other words, the improvement in enzyme activity inhibition effect is a unique effect due to the combined use of alkylglycoside type nonionic surfactants. Simply improving the solubilization ability of β-glucuronidase inhibitor in aqueous solution will inhibit the enzyme activity. Did not improve.
参考例4 界面活性剤によるβ-グルクロニダーゼ阻害剤の菌体浸透/付着量の増加
(1)菌液の調製
実施例1-1〜1-4及び比較例1-1〜1-3の(1)で得た尿臭産生菌をミュラーヒントン培地で培養し、遠心操作によって液部を除いた。残った菌体部分を生理食塩水に懸濁させ、再度、遠心操作によって液部を除き、この操作を2度行うことによって菌体部分の洗浄を行った。これをD-PBS(Dulbecco’s Phosphate Buffered Saline)を用いて適宜希釈し、波長600nmにおける吸光度が8となるように調製した。
Reference Example 4 Increasing cell penetration / attachment amount of β-glucuronidase inhibitor by surfactant (1) Preparation of bacterial solution Examples 1-1 to 1-4 and Comparative Examples 1-1 to 1-3 (1 The urine odor producing bacteria obtained in (1) were cultured in Mueller Hinton medium, and the liquid part was removed by centrifugation. The remaining bacterial cell part was suspended in physiological saline, the liquid part was removed again by centrifugation, and this operation was performed twice to wash the bacterial cell part. This was appropriately diluted with D-PBS (Dulbecco's Phosphate Buffered Saline) and prepared so that the absorbance at a wavelength of 600 nm was 8.
(2)β-グルクロニダーゼ阻害剤の菌体浸透/付着量の測定
表5に示す処方により、D-PBS中にβ-グルクロニダーゼ阻害剤(8-シクロヘキサデセン-1-オン)を0.01w/v%、実施例1-1で用いたドデシルグルコシドを0、0.01若しくは0.1w/v%、又は比較例1-1で用いたポリオキシエチレンソルビタンモノオレエートを0.1w/v%、菌体を波長600nmにおける反応液中での吸光度が0.4又は0.8となるように含んだ各溶液を調製した。
この溶液を37℃恒温槽中において2時間静置後、遠心操作によって菌体部分を回収し、塩化ナトリウム水溶液によって数回洗浄を行った。続いて、少量の生理食塩水を加えて内容物を再懸濁させ、ガラス容器に移して密栓し、超音波処理を行うことによって菌体の破砕を行った。ここへ内部標準としてベンジルベンゾエート エタノール溶液を添加した後、ジエチルエーテルで阻害剤の抽出を行った。抽出液は無水硫酸マグネシウムで乾燥させ、固形物をろ別後、ろ液を濃縮して測定サンプルとした。
測定にはガスクロマトグラフ質量分析計を用い、内部標準に対するピークエリア比として菌体からの阻害剤検出量を算出した。結果を図1に示す。
(2) Measurement of cell penetration / attachment amount of β-glucuronidase inhibitor 0.01 w / v% of β-glucuronidase inhibitor (8-cyclohexadecen-1-one) in D-PBS according to the formulation shown in Table 5 The dodecyl glucoside used in Example 1-1 was 0, 0.01, or 0.1 w / v%, or the polyoxyethylene sorbitan monooleate used in Comparative Example 1-1 was 0.1 w / v%, and the cells were at a wavelength of 600 nm. Each solution was prepared so that the absorbance in the reaction solution was 0.4 or 0.8.
This solution was allowed to stand in a 37 ° C. constant temperature bath for 2 hours, and then the bacterial cell part was recovered by centrifugation and washed several times with an aqueous sodium chloride solution. Subsequently, a small amount of physiological saline was added to resuspend the contents, transferred to a glass container, sealed, and subjected to ultrasonic treatment to crush the cells. After adding a benzyl benzoate ethanol solution as an internal standard, the inhibitor was extracted with diethyl ether. The extract was dried over anhydrous magnesium sulfate, the solid matter was filtered off, and the filtrate was concentrated to obtain a measurement sample.
A gas chromatograph mass spectrometer was used for the measurement, and the detected amount of inhibitor from the cells was calculated as the peak area ratio relative to the internal standard. The results are shown in FIG.
以上の結果より、アルキルグリコシド型非イオン界面活性剤は、β-グルクロニダーゼ阻害剤の菌体への浸透又は吸着を促進させていることがわかる。 From the above results, it can be seen that the alkylglycoside type nonionic surfactant promotes the penetration or adsorption of the β-glucuronidase inhibitor into the cells.
実施例2-1、2-2、比較例2-1〜2-4 β-グルクロニダーゼ阻害剤と界面活性剤の併用による阻害効果の向上及び尿臭気の生成抑制効果
(1)菌液の調製
実施例1-1〜1-4及び比較例1-1〜1-3の(1)で得た尿臭産生菌をヒト尿サンプル(除菌済み、2名の等量混合物)中で培養し、遠心操作によって液部を除いた。残った菌体部分を生理食塩水に懸濁させ、再度、遠心操作によって液部を除き、この操作を2度行うことによって菌体部分の洗浄を行った。これを生理食塩水を用いて適宜希釈し、波長600nmにおける吸光度が2となるように調製した。
Examples 2-1 and 2-2, Comparative Examples 2-1 and 2-4 Improvement of inhibitory effect and suppression of urine odor production by combined use of β-glucuronidase inhibitor and surfactant (1) Preparation of bacterial solution The urine odor producing bacteria obtained in (1-1) of Examples 1-1 to 1-4 and Comparative Examples 1-1 to 1-3 were cultured in human urine samples (sterilized, mixture of two equivalents), The liquid part was removed by centrifugation. The remaining bacterial cell part was suspended in physiological saline, the liquid part was removed again by centrifugation, and this operation was performed twice to wash the bacterial cell part. This was appropriately diluted with physiological saline and prepared so that the absorbance at a wavelength of 600 nm was 2.
(2)尿臭産生菌細胞内β-グルクロニダーゼ活性の抑制効果測定
表6に示す組成(w/v%)のβ-グルクロニダーゼ阻害剤(8-シクロヘキサデセン-1-オン)及び/又は本発明のアルキルグリコシド型非イオン界面活性剤(ドデシルグルコシド:花王(株)製、マイドール12)を含有する実施例2-1、2-2及び比較例2-1から2-4の尿臭生成抑制用組成物を調製し、各組成物とヒト尿サンプル(除菌済み、2名の等量混合物)を体積比1対4で混合した。これら組成物添加尿に対して1mMとなるようにPNPGを溶解させ、更に本実施例(1)で調製した尿臭産生菌菌液を1vol%添加混合し、得られた各サンプルを30℃恒温槽中で4時間反応させた。反応液中での濃度はそれぞれ、β-グルクロニダーゼ阻害剤は0.01w/v%、界面活性剤は0.005w/v%又は0.1w/v%となる。
また、各サンプルについて、菌液に換えて生理食塩水を加えたものをブランクとして、同様に4時間反応を行った。
反応終了後、反応液の一部を0.2Mグリシン-水酸化ナトリウム緩衝液(pH10.4)を用いて希釈し、10000rpmで2分間遠心操作を行い、遠心後の上清を用いて波長400nmにおける吸光度を測定した。得られた測定値より、次式に従って各サンプルにおける尿臭産生菌細胞内β-グルクロニダーゼの相対活性を求め、結果を表6に示した。
(2) Measurement of inhibitory effect on intracellular β-glucuronidase activity of urine odor producing bacteria β-glucuronidase inhibitor (8-cyclohexadecen-1-one) having the composition (w / v%) shown in Table 6 and / or of the present invention For inhibiting urine odor production in Examples 2-1 and 2-2 and Comparative Examples 2-1 to 2-4 containing an alkylglycoside type nonionic surfactant (dodecylglucoside: manufactured by Kao Corporation, Mydol 12) Compositions were prepared, and each composition and human urine sample (sterilized, mixture of two equivalents) were mixed at a volume ratio of 1: 4. PNPG is dissolved so that it becomes 1 mM with respect to urine added with these compositions, and further, 1 vol% of the urine odor producing bacterial solution prepared in this Example (1) is added and mixed. The reaction was allowed to proceed for 4 hours in the bath. The concentration in the reaction solution is 0.01 w / v% for the β-glucuronidase inhibitor and 0.005 w / v% or 0.1 w / v% for the surfactant, respectively.
In addition, each sample was similarly reacted for 4 hours using a blank obtained by adding physiological saline instead of the bacterial solution.
After completion of the reaction, a part of the reaction solution is diluted with 0.2 M glycine-sodium hydroxide buffer (pH 10.4), centrifuged at 10,000 rpm for 2 minutes, and the centrifuged supernatant is used at a wavelength of 400 nm. Absorbance was measured. From the obtained measured values, the relative activity of β-glucuronidase in urine odor producing bacteria in each sample was determined according to the following formula, and the results are shown in Table 6.
(4)抗菌効果測定
表6に示した各サンプルについて、30℃、4時間反応後、その一部をLP希釈液(日本製薬(株)製)を用いて希釈し、SCDLP寒天平板培地に接種して生菌数の測定を行った。また比較例2-4と同じ組成のサンプルを別途調製し、菌液添加直後に同様の手法で生菌数の測定を行い、これを初期添加菌数とした。測定は同じサンプルについて3回行い、その平均値により、サンプルの生菌数が初期添加菌数の1/10未満となったものを抗菌効果有り(○と記載)、1/10以上であったものを抗菌効果無し(×と記載)と判定し、結果を表6に示した。
(4) Antibacterial effect measurement About each sample shown in Table 6, after reacting at 30 ° C for 4 hours, a part of it was diluted with LP diluent (manufactured by Nippon Pharmaceutical Co., Ltd.) and inoculated on SCDLP agar plate medium. Then, the number of viable bacteria was measured. A sample having the same composition as Comparative Example 2-4 was prepared separately, and immediately after the addition of the bacterial solution, the number of viable bacteria was measured by the same method, and this was used as the initial number of added bacteria. Measurement was performed three times for the same sample, and the average value of the sample was less than 1/10 of the initial number of bacteria added. The product was determined to have no antibacterial effect (denoted as x), and the results are shown in Table 6.
(5)臭気強度評価(臭気生成抑制効果測定)
表6に示した各サンプルについて、30℃、4時間反応させたものをそれぞれ等量、匂い紙先端に滴下し、これを臭気評価サンプルとした。臭気強度評価は臭気判定士の資格を有する2名の専門パネラーが携わり、0〜5の評価スコアによる6段階臭気強度表示法に準じて行った。即ち評価スコアは、「0」無臭、「1」やっと感知できるニオイ(検知閾値)、「2」尿臭であることわかるが弱いニオイ(認知閾値)、「3」楽に尿臭であると感じられるニオイ、「4」強い尿臭、「5」強烈な尿臭を示す。臭気強度の判定は0.5刻みで行い、2名の評価の平均値について、小数点以下の数値を0.25以上0.75未満は0.5とし、0.75以上は整数に切り上げ、0.25未満は整数に切り捨てた。得られた結果を表6に示した。
(5) Odor strength evaluation (measurement of odor generation suppression effect)
About each sample shown in Table 6, what was made to react at 30 degreeC for 4 hours was dripped at the odor paper tip equally, and this was made into the odor evaluation sample. Odor intensity evaluation was conducted in accordance with a 6-step odor intensity display method based on an evaluation score of 0 to 5 by two professional panelists who have qualifications as an odor judge. That is, the evaluation score is “0” odorless, “1” is finally perceivable odor (detection threshold), “2” urine odor is known, but weak odor (cognitive threshold), “3” feels urine odor easily. Odor, “4” strong urine odor, “5” intense urine odor. The odor intensity was determined in increments of 0.5, and the average value of the evaluation of the two persons was set to 0.5 when the numerical value after the decimal point was 0.25 or more and less than 0.75, rounded up to 0.75 or more and rounded down to less than 0.25. The results obtained are shown in Table 6.
以上の結果に示したとおり、界面活性剤のみでは抗菌効果の有無に関わらず尿臭産生菌に由来するβ-グルクロニダーゼの活性を抑制することができず、尿臭気の生成抑制効果も得られなかった。一方で本発明のβ-グルクロニダーゼ阻害剤とアルキルグリコシド型非イオン界面活性剤からなる尿臭生成抑制用組成物は、抗菌効果の有無に関わらずβ-グルクロニダーゼ阻害剤を単独で用いた場合よりも細胞内β-グルクロニダーゼに対して優れた阻害活性を示し、尿臭気の生成についても、これをより効果的に抑制した。 As shown in the above results, the surfactant alone cannot suppress the activity of β-glucuronidase derived from urine odor producing bacteria regardless of the antibacterial effect, and the urine odor production suppressing effect is not obtained. It was. On the other hand, the composition for suppressing urine odor production comprising the β-glucuronidase inhibitor and the alkylglycoside type nonionic surfactant of the present invention is more effective than the case where the β-glucuronidase inhibitor is used alone regardless of the antibacterial effect. It showed excellent inhibitory activity against intracellular β-glucuronidase, and more effectively suppressed urine odor production.
実施例3 スプレー型製品
表7に示す組成(重量%)のβ-グルクロニダーゼ阻害剤(8-シクロヘキサデセン-1-オン)及び各種界面活性剤を含有する尿臭生成抑制用組成物を調製し、これをトリガースプレー容器に入れて、スプレー型製品を作製した。組成物のpHは6.5〜7.5になるように調整した。
Example 3 Spray-type product A composition for suppressing urine odor production containing a β-glucuronidase inhibitor (8-cyclohexadecen-1-one) having a composition (% by weight) shown in Table 7 and various surfactants was prepared. This was put into a trigger spray container to produce a spray-type product. The pH of the composition was adjusted to 6.5-7.5.
<配合成分(界面活性剤)>
アルキルグリコシド型非イオン界面活性剤1:ドデシルグルコシド(花王(株)製、マイドール12、グルコース平均縮合度1.3)
アルキルグリコシド型非イオン界面活性剤2:デシルグルコシド(花王(株)製、マイドール10)
アルキルグリコシド型非イオン界面活性剤3:イソデシルガラクトシド
アルキルグリコシド型非イオン界面活性剤4:オクチルガラクトシド
非イオン界面活性剤1:N-ラウロイルアミノプロピル-N,N-ジメチルアミンオキシド
非イオン界面活性剤2:ポリオキシエチレン(平均8モル)ラウリルエーテル
両性界面活性剤1:N-ラウロイルアミノプロピル-N,N-ジメチル-N-(2-ヒドロキシスルホプロピル)アンモニウムベタイン
両性界面活性剤2:N-ラウロイルアミノプロピル-N,N-ジメチル-N-カルボシキメチルアンモニウムベタイン
カチオン界面活性剤1:ジデシルジメチルアンモニウムクロリド(花王(株)製、コータミンD-10E)
カチオン界面活性剤2:アルキルベンジルアンモニウムクロリド(花王(株)製、サニゾールC、アルキル基の炭素数は12)
アニオン界面活性剤1:アルキルベンゼンスルホン酸ナトリウム(アルキル基の炭素数は11〜15)
アニオン界面活性剤2:ラウリル硫酸ナトリウム
<Compounding ingredients (surfactant)>
Alkyl glycoside type nonionic surfactant 1: dodecyl glucoside (manufactured by Kao Corporation, Mydol 12, average degree of condensation of glucose 1.3)
Alkyl glycoside type nonionic surfactant 2: Decyl glucoside (manufactured by Kao Corporation, Mydol 10)
Alkyl glycoside type nonionic surfactant 3: Isodecyl galactoside Alkyl glycoside type nonionic surfactant 4: Octyl galactoside Nonionic surfactant 1: N-lauroylaminopropyl-N, N-dimethylamine oxide Nonionic surfactant 2: Polyoxyethylene (average 8 mol) lauryl ether Amphoteric surfactant 1: N-lauroylaminopropyl-N, N-dimethyl-N- (2-hydroxysulfopropyl) ammonium betaine Amphoteric surfactant 2: N-lauroyl Aminopropyl-N, N-dimethyl-N-carboxymethylammonium betaine Cationic surfactant 1: Didecyldimethylammonium chloride (manufactured by Kao Corporation, Coatamine D-10E)
Cationic surfactant 2: Alkylbenzylammonium chloride (manufactured by Kao Corporation, Sanizol C, carbon number of alkyl group is 12)
Anionic surfactant 1: Sodium alkylbenzene sulfonate (the alkyl group has 11 to 15 carbon atoms)
Anionic surfactant 2: Sodium lauryl sulfate
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R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |