JP4091498B2 - Antiseptic disinfectant and cosmetics, pharmaceuticals and foods containing the antiseptic disinfectant - Google Patents
Antiseptic disinfectant and cosmetics, pharmaceuticals and foods containing the antiseptic disinfectant Download PDFInfo
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- JP4091498B2 JP4091498B2 JP2003301851A JP2003301851A JP4091498B2 JP 4091498 B2 JP4091498 B2 JP 4091498B2 JP 2003301851 A JP2003301851 A JP 2003301851A JP 2003301851 A JP2003301851 A JP 2003301851A JP 4091498 B2 JP4091498 B2 JP 4091498B2
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- antiseptic disinfectant
- antiseptic
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- coconut oil
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- 239000000645 desinfectant Substances 0.000 title claims description 26
- 239000002537 cosmetic Substances 0.000 title claims description 18
- 235000013305 food Nutrition 0.000 title claims description 15
- 239000003814 drug Substances 0.000 title description 21
- 150000004665 fatty acids Chemical class 0.000 claims description 34
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- 235000014113 dietary fatty acids Nutrition 0.000 claims description 33
- 239000000194 fatty acid Substances 0.000 claims description 33
- 229930195729 fatty acid Natural products 0.000 claims description 33
- ZSUZUJSDKZPWHH-UHFFFAOYSA-N ethyl 2-oxopyrrolidine-1-carboxylate Chemical compound CCOC(=O)N1CCCC1=O ZSUZUJSDKZPWHH-UHFFFAOYSA-N 0.000 claims description 26
- 239000000126 substance Substances 0.000 claims description 18
- 229940031723 1,2-octanediol Drugs 0.000 claims description 16
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- PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 2
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- SVBBTCUNQJOQAA-UHFFFAOYSA-N 3-ethyl-2-oxopyrrolidine-1-carboxylic acid Chemical compound CCC1CCN(C(O)=O)C1=O SVBBTCUNQJOQAA-UHFFFAOYSA-N 0.000 description 1
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229930182558 Sterol Chemical class 0.000 description 1
- OMOVVBIIQSXZSZ-UHFFFAOYSA-N [6-(4-acetyloxy-5,9a-dimethyl-2,7-dioxo-4,5a,6,9-tetrahydro-3h-pyrano[3,4-b]oxepin-5-yl)-5-formyloxy-3-(furan-3-yl)-3a-methyl-7-methylidene-1a,2,3,4,5,6-hexahydroindeno[1,7a-b]oxiren-4-yl] 2-hydroxy-3-methylpentanoate Chemical compound CC12C(OC(=O)C(O)C(C)CC)C(OC=O)C(C3(C)C(CC(=O)OC4(C)COC(=O)CC43)OC(C)=O)C(=C)C32OC3CC1C=1C=COC=1 OMOVVBIIQSXZSZ-UHFFFAOYSA-N 0.000 description 1
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- 239000010775 animal oil Substances 0.000 description 1
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- CUBCNYWQJHBXIY-UHFFFAOYSA-N benzoic acid;2-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1O CUBCNYWQJHBXIY-UHFFFAOYSA-N 0.000 description 1
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- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Detergent Compositions (AREA)
- Non-Alcoholic Beverages (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
- Cosmetics (AREA)
Description
本発明は、防腐殺菌剤並びに該防腐殺菌剤を配合した化粧料、医薬品及び食品に関する。より具体的には、炭素数５〜１０の１，２−アルカンジオールとＮ−ヤシ油脂肪酸アシル−Ｌ−アルギニンエチルピロリドンカルボン酸塩とを共に有効成分として含有することにより、１，２−アルカンジオール及びＮ−ヤシ油脂肪酸アシル−Ｌ−アルギニンエチルピロリドンカルボン酸塩が本来有する抗菌力を相乗的に増強する防腐殺菌剤並びに該防腐殺菌剤を配合した化粧料、医薬品及び食品に関する。 The present invention relates to an antiseptic disinfectant and cosmetics, pharmaceuticals and foods containing the antiseptic disinfectant. More specifically, it contains 1,2-alkanediol having 5 to 10 carbon atoms and N-coconut oil fatty acid acyl-L-arginine ethylpyrrolidone carboxylate as active ingredients. The present invention relates to an antiseptic fungicide that synergistically enhances the antibacterial activity inherent in diol and N-coconut oil fatty acid acyl-L-arginine ethylpyrrolidone carboxylate, and a cosmetic, a pharmaceutical and a food containing the antiseptic fungicide.
化粧品（医薬部外品を含む）、医薬品及び食品などには、防腐殺菌剤として、パラベン、安息香酸類、サリチル酸類等が用いられている。しかしながら、上記した従来の防腐殺菌剤は皮膚刺激性が高いなど安全性が低いため、使用濃度範囲が制限されやすいといった欠点を有していた。例えば、パラベンや安息香酸塩の使用制限濃度は１％、安息香酸やサリチル酸の使用制限濃度は０．２％とされている。また、これら防腐殺菌剤はｐＨによる影響を受け易いため、防腐殺菌効果の安定性が悪く、界面活性剤などの他の配合成分との併用によりその防腐殺菌効果が著しく低下する場合があるといった問題も有していた。また、近年これらの防腐殺菌剤に対してアレルギー反応を起こす人が増えているために生活者の安全性に対する指向がより強まり、これら防腐殺菌剤を全く配合していないか、或いはその配合量を低減させた化粧料、医薬品及び食品の需要が高まっている。 Parabens, benzoic acids, salicylic acids, and the like are used as antiseptic fungicides in cosmetics (including quasi drugs), pharmaceuticals, and foods. However, the above-mentioned conventional antiseptic disinfectant has a drawback that the concentration range in use is easily limited because of low safety such as high skin irritation. For example, the use restriction concentration of paraben and benzoate is 1%, and the use restriction concentration of benzoic acid and salicylic acid is 0.2%. Moreover, since these antiseptic disinfectants are easily affected by pH, the stability of the antiseptic disinfecting effect is poor, and the antiseptic disinfecting effect may be remarkably lowered when used in combination with other compounding ingredients such as surfactants. Also had. In recent years, the number of people who cause allergic reactions to these antiseptics has increased, so the consumer safety has become stronger. There is an increasing demand for reduced cosmetics, pharmaceuticals and foods.
そこで、１，２−アルカンジオールを用いた防腐殺菌剤に関する技術として、１，２−アルカンジオールが大腸菌や黄色ブドウ状球菌等に対して抗菌力を有することが報告されている（特許文献１参照）。また、１，２−アルカンジオールと他の防腐殺菌力を有する物質とを併用した技術としては、１，２−ペンタンジオールと２−フェノキシエタノールからなる外用組成物（特許文献２参照）、１，２−アルカンジオールとパラベンからなる防腐殺菌剤（特許文献３参照）、１，２−アルカンジオールとヒノキチオールからなる外用組成物（特許文献４参照）等が開示されている。 Therefore, it has been reported that 1,2-alkanediol has antibacterial activity against Escherichia coli, Staphylococcus aureus and the like as a technique related to antiseptic fungicides using 1,2-alkanediol (see Patent Document 1). ). In addition, as a technique using a combination of 1,2-alkanediol and another substance having antiseptic sterilization power, an external composition composed of 1,2-pentanediol and 2-phenoxyethanol (see Patent Document 2), 1,2 -An antiseptic disinfectant composed of alkanediol and paraben (see Patent Document 3), an external composition composed of 1,2-alkanediol and hinokitiol (see Patent Document 4), and the like are disclosed.
一方、Ｎ−ヤシ油脂肪酸アシル−Ｌ−アルギニンエチルピロリドンカルボン酸塩も、抗菌力を有することが知られており、他の防腐殺菌力を有する物質と併用する技術としては、ヒノキチオールと併用した化粧品（特許文献５）が開示されている。 On the other hand, N-coconut oil fatty acid acyl-L-arginine ethylpyrrolidone carboxylate is also known to have antibacterial activity, and as a technique used in combination with other substances having antiseptic sterilization power, cosmetics used in combination with hinokitiol (Patent Document 5) is disclosed.
しかしながら、従来の１，２−アルカンジオールやＮ−ヤシ油脂肪酸アシル−Ｌ−アルギニンエチルピロリドンカルボン酸塩を用いた防腐殺菌剤に関する技術は、パラベンや安息香酸類等の防腐殺菌剤の配合量を低減又は排除させるために、１，２−アルカンジオールやＮ−ヤシ油脂肪酸アシル−Ｌ−アルギニンエチルピロリドンカルボン酸塩を併用するものであって、１，２−アルカンジオールやＮ−ヤシ油脂肪酸アシル−Ｌ−アルギニンエチルピロリドンカルボン酸塩が本来有する抗菌力をさらに増強させようとする試みは全くなされていなかった。 However, conventional technology related to antiseptics using 1,2-alkanediol and N-coconut oil fatty acid acyl-L-arginine ethylpyrrolidone carboxylate reduces the amount of antiseptics such as parabens and benzoic acids. Or in order to eliminate 1,2-alkanediol and N-coconut oil fatty acid acyl-L-arginine ethylpyrrolidone carboxylate, wherein 1,2-alkanediol and N-coconut oil fatty acid acyl- No attempt has been made to further enhance the antibacterial activity inherent to L-arginine ethylpyrrolidone carboxylate.
本発明は前記従来技術に鑑みてなされたものであって、１，２−アルカンジオールとＮ−ヤシ油脂肪酸アシル−Ｌ−アルギニンエチルピロリドンカルボン酸塩とを有効成分として共に用いると、１，２−アルカンジオール及びＮ−ヤシ油脂肪酸アシル−Ｌ−アルギニンエチルピロリドンカルボン酸塩が本来有する抗菌力を相乗的に増強することができる防腐殺菌剤並びに該防腐殺菌剤を配合した化粧料、医薬品及び食品を提供することを課題とする。 The present invention has been made in view of the above prior art, and when 1,2-alkanediol and N-coconut oil fatty acid acyl-L-arginine ethylpyrrolidone carboxylate are used together as active ingredients, -Antiseptic disinfectant capable of synergistically enhancing antibacterial activity inherent in alkanediol and N-coconut oil fatty acid acyl-L-arginine ethylpyrrolidone carboxylate, and cosmetics, pharmaceuticals and foods containing the antiseptic disinfectant It is an issue to provide.
即ち、請求項１に係る発明は、次式１（化１）に示される炭素数５〜１０の１，２−アルカンジオールと、次式２（化２）に示されるＮ−ヤシ油脂肪酸アシル−Ｌ−アルギニンエチルピロリドンカルボン酸塩とを含有することを特徴とする防腐殺菌剤に関する。 That is, the invention according to claim 1 includes a 1,2-alkanediol having 5 to 10 carbon atoms represented by the following formula 1 (chemical formula 1) and an N-coconut oil fatty acid acyl represented by the following formula 2 (chemical formula 2). The present invention relates to an antiseptic disinfectant characterized by containing -L-arginine ethylpyrrolidone carboxylate.
請求項２に係る発明は、前記１，２−アルカンジオールが、１，２−ヘキサンジオール及び／又は１，２−オクタンジオールであることを特徴とする請求項１に記載の防腐殺菌剤に関する。
請求項３に係る発明は、前記１，２−アルカンジオールが、１，２−オクタンジオールであることを特徴とする請求項１に記載の防腐殺菌剤に関する。
請求項４に係る発明は、請求項１乃至３のいずれかに記載の防腐殺菌剤を配合していることを特徴とする医薬品または食品に関する。
請求項５に係る発明は、請求項１乃至３のいずれかに記載の防腐殺菌剤を配合していることを特徴とする化粧品（但し、１，２−ペンタンジオール又は１，２−ヘキサンジオールを含有するものを除く）に関する。
The invention according to claim 2 relates to the antiseptic fungicide according to claim 1, wherein the 1,2-alkanediol is 1,2-hexanediol and / or 1,2-octanediol.
The invention according to claim 3 relates to the antiseptic fungicide according to claim 1, wherein the 1,2-alkanediol is 1,2-octanediol.
The invention according to claim 4 relates to a medicine or food characterized by containing the antiseptic disinfectant according to any one of claims 1 to 3 .
The invention according to
本発明によれば、１，２−アルカンジオール及びＮ−ヤシ油脂肪酸アシル−Ｌ−アルギニンエチルピロリドンカルボン酸塩の本来有する抗菌力が相乗的に増強された防腐殺菌剤並びに該防腐殺菌剤を配合した化粧料、医薬品及び食品を提供することができる。 According to the present invention, 1,2-alkanediol and N-coconut oil fatty acid acyl-L-arginine ethyl pyrrolidone carboxylate have a synergistically enhanced antibacterial activity and inherently contain the antiseptic disinfectant. Cosmetics, medicines and foods can be provided.
以下、本発明に係る防腐殺菌剤について詳述する。本発明に係る防腐殺菌剤は、１，２−アルカンジオールとＮ−ヤシ油脂肪酸アシル−Ｌ−アルギニンエチルピロリドンカルボン酸塩を有効成分として含有する。
本発明に係る防腐殺菌剤の第一の成分は、次式３（化３）に示される炭素数５〜１０の１，２−アルカンジオールであり、具体的には、１，２−ペンタンジオール、１，２−ヘキサンジオール、１，２−ヘプタンジオール、１，２−オクタンジオール、１，２−ノナンジオール、１，２−デカンジオールである。
Hereinafter, the antiseptic disinfectant according to the present invention will be described in detail. The antiseptic fungicide according to the present invention contains 1,2-alkanediol and N-coconut oil fatty acid acyl-L-arginine ethylpyrrolidone carboxylate as active ingredients.
The first component of the antiseptic fungicide according to the present invention is a 1,2-alkanediol having 5 to 10 carbon atoms represented by the following formula 3 (Chemical formula 3), specifically, 1,2-pentanediol. 1,2-hexanediol, 1,2-heptanediol, 1,2-octanediol, 1,2-nonanediol, 1,2-decanediol.
本発明では、前述の炭素数５〜１０の１，２−アルカンジオールのうちの一種を単独で使用することもでき、二種以上を混合して用いることもできる。
１，２−アルカンジオールはそれ自体優れた抗菌力を有しており、本発明に係る防腐殺菌剤の抗菌力を高める効果を奏する。特に本発明では、一般細菌、酵母などに対して優れた抗菌作用を示すことから、炭素数５〜１０の１，２−アルカンジオールのうち、１，２−ヘキサンジオール、１，２−オクタンジオールを用いることが好ましく、１，２−オクタンジオールを用いることがより好ましい。
In the present invention, one of the above-mentioned 1,5-alkanediols having 5 to 10 carbon atoms can be used alone, or two or more kinds can be mixed and used.
1,2-alkanediol itself has excellent antibacterial activity, and has the effect of increasing the antibacterial activity of the antiseptic disinfectant according to the present invention. In particular, in the present invention, since it exhibits an excellent antibacterial action against general bacteria, yeast and the like, among 1,2-alkanediols having 5 to 10 carbon atoms, 1,2-hexanediol, 1,2-octanediol It is preferable to use 1,2-octanediol.
本発明に係る防腐殺菌剤の第二の成分は、次式４（化４）に示されるＮ−ヤシ油脂肪酸アシル−Ｌ−アルギニンエチルピロリドンカルボン酸塩である。 The second component of the antiseptic fungicide according to the present invention is an N-coconut oil fatty acid acyl-L-arginine ethylpyrrolidone carboxylate represented by the following formula 4 (Chemical formula 4).
Ｎ−ヤシ油脂肪酸アシル−Ｌ−アルギニンエチルピロリドンカルボン酸塩は、Ｌ−アルギニンとヤシ油脂肪酸との縮合物をエタノールでエステル化し、ＤＬ−ピロリドンカルボン酸塩としたものである。このような市販のＮ−ヤシ油脂肪酸アシル−Ｌ−アルギニンエチルピロリドンカルボン酸塩としては、商品名ＣＡＥ（登録商標、味の素株式会社製）を例示することができる。
N-coconut oil fatty acid acyl-L-arginine ethylpyrrolidone carboxylate is obtained by esterifying a condensate of L-arginine and palm oil fatty acid with ethanol to form DL-pyrrolidone carboxylate. As such commercially available N-coconut oil fatty acid acyl-L-arginine ethylpyrrolidone carboxylate, trade name CAE (registered trademark, manufactured by Ajinomoto Co., Inc.) can be exemplified.
本発明に係る防腐殺菌剤において、第一の成分である炭素数５〜１０の１，２−アルカンジオールと第二の成分であるＮ−ヤシ油脂肪酸アシル−Ｌ−アルギニンエチルピロリドンカルボン酸塩の含有量は特に限定されないが、重量比で１：１０〜１０：１、好ましくは１：５〜５：１となるように配合する。１，２−アルカンジオールをＮ−ヤシ油脂肪酸アシル−Ｌ−アルギニンエチルピロリドンカルボン酸塩の配合量の１０重量倍を超えて配合すると、またＮ−ヤシ油脂肪酸アシル−Ｌ−アルギニンエチルピロリドンカルボン酸塩を１，２−アルカンジオールの配合量の１０重量倍を超えて配合すると、共に抗菌活性の増強効果が期待できなくなるために好ましくない。 In the antiseptic disinfectant according to the present invention, the first component of 1,2-alkanediol having 5 to 10 carbon atoms and the second component of N-coconut oil fatty acid acyl-L-arginine ethylpyrrolidonecarboxylate Although content is not specifically limited, It mix | blends so that it may become 1: 10-10: 1 by weight ratio, Preferably it is 1: 5-5: 1. When 1,2-alkanediol is added in an amount exceeding 10 times the amount of N-coconut oil fatty acid acyl-L-arginine ethylpyrrolidone carboxylate, N-coconut oil fatty acid acyl-L-arginine ethylpyrrolidonecarboxylic acid If the salt is added in an amount exceeding 10 times the amount of 1,2-alkanediol, it is not preferable because an antibacterial activity enhancing effect cannot be expected.
本発明に係る防腐殺菌剤は、第一の成分である１，２−アルカンジオールと、第二の成分であるＮ−ヤシ油脂肪酸アシル−Ｌ−アルギニンエチルピロリドンカルボン酸塩を含有するから、後述する試験に示されるように、第一の成分と第二の成分との相乗効果によって、一般細菌、カビなどの菌に対して相乗的に増強された防腐殺菌作用が発揮される。従って、パラベン、安息香酸、サリチル酸のような以前から用いられている防腐殺菌剤を低配合又は配合する必要がなくなり、極めて高い安全性を得ることもできる。 The antiseptic disinfectant according to the present invention contains 1,2-alkanediol as the first component and N-coconut oil fatty acid acyl-L-arginine ethylpyrrolidone carboxylate as the second component. As shown in the test, the synergistic effect of the first component and the second component exerts a synergistically enhanced antiseptic and bactericidal action against bacteria such as general bacteria and mold. Therefore, it is not necessary to blend or blend a preservative antibacterial agent such as paraben, benzoic acid or salicylic acid, which has been used before, and extremely high safety can be obtained.
上述した本発明に係る防腐殺菌剤は、化粧品、医薬品及び食品などに配合して使用することができる。
具体的には、洗顔料、化粧水、乳液、クリーム、ファンデーション、マスカラ、ネールエナメル、口紅などの皮膚用化粧料、シャンプー、ヘアトリートメント、養毛・育毛料、ヘアクリーム、ヘアローション、ヘアフォーム、パーマネントウェーブ剤などの頭髪用化粧料、しみやそばかすなどの特定の使用目的を有した薬用化粧料（医薬部外品）、にきび治療薬、うがい薬、トローチなどの医薬品、さらにはチューインガム、キャンディー、飲料などの食品に好適に用いることができる。
The antiseptic disinfectant according to the present invention described above can be used by blending it in cosmetics, pharmaceuticals, foods and the like.
Specifically, cosmetics for skin such as face wash, lotion, milky lotion, cream, foundation, mascara, nail enamel, lipstick, shampoo, hair treatment, hair nourishing and hair restorer, hair cream, hair lotion, hair foam, Hair cosmetics such as permanent wave agents, medicinal cosmetics (quasi-drugs) with specific uses such as stains and freckles, acne medicines, gargles, lozenges, chewing gum, candy, It can use suitably for foodstuffs, such as a drink.
本発明に係る防腐殺菌剤を用いて化粧品、医薬品又は食品を調製する場合、本発明の効果が損なわれない範囲内で化粧品、医薬品又は食品に通常用いられる成分を適宜任意に配合することができる。例えば、化粧品や医薬品（医薬部外品を含む）の場合、油脂、ロウ類、高級脂肪酸、低級アルコール、高級アルコール、ステロール、脂肪酸エステル、保湿剤、界面活性剤、高分子化合物、無機顔料、色素、香料、酸化防止剤、紫外線吸収剤、ビタミン類、収斂剤、美白剤、動植物抽出物、金属イオン封鎖剤、精製水などを例示することができる。
また食品の場合は、動植物油、多糖類、甘味料、着色料、ガムベースなどを例示することができる。
化粧品、医薬品又は食品を調製する場合、本発明に係る防腐殺菌剤の配合量は特に限定されないが、組成物中、０．０１〜２０重量％、好ましくは０．０５〜５重量％配合する。２０重量％を超えて配合したとしてもそれ以上の効果が望めない。また０．０１重量％未満の場合は、抗菌効果が劣るために好ましくない。
In the case of preparing cosmetics, pharmaceuticals or foods using the antiseptic disinfectant according to the present invention, components usually used in cosmetics, pharmaceuticals or foods can be arbitrarily arbitrarily blended within the range where the effects of the present invention are not impaired. . For example, in the case of cosmetics and pharmaceuticals (including quasi drugs), fats and oils, waxes, higher fatty acids, lower alcohols, higher alcohols, sterols, fatty acid esters, humectants, surfactants, polymer compounds, inorganic pigments, dyes , Fragrances, antioxidants, ultraviolet absorbers, vitamins, astringents, whitening agents, animal and plant extracts, sequestering agents, purified water, and the like.
In the case of foods, animal and vegetable oils, polysaccharides, sweeteners, colorants, gum bases and the like can be exemplified.
When preparing cosmetics, pharmaceuticals or foods, the amount of the antiseptic disinfectant according to the present invention is not particularly limited, but is 0.01 to 20% by weight, preferably 0.05 to 5% by weight in the composition. Even if it exceeds 20% by weight, no further effect can be expected. Moreover, when it is less than 0.01% by weight, the antibacterial effect is inferior, which is not preferable.
（殺菌力テスト）
供試菌は、黄色ブドウ状球菌（Staphylococcus aureus IFO13276）及びクロカビ（Aspergillus niger IFO9455）を用いた。
(Bactericidal test)
As test bacteria, Staphylococcus aureus IFO13276 and black mold (Aspergillus niger IFO9455) were used.
（接種用菌液の調製）
接種用菌液としては、黄色ブドウ状球菌の場合、寒天培地で、３５℃で培養後、更にブイヨン培地に移植して、３５℃で培養した。得られた培養液をブイヨン培地で約１０８個／ｍｌに希釈したものを接種用菌液とした。
また、クロカビの場合は、２５℃で培養後にTween 80（ポリオキシエチレン（２０）ソルビタンモノオレエート）０．２％加生理食塩水に胞子を懸濁させ約１０６個／ｍｌに調製したものを接種用菌液とした。
(Preparation of bacterial solution for inoculation)
In the case of Staphylococcus aureus, the bacterial solution for inoculation was cultured on an agar medium at 35 ° C., then transplanted to a bouillon medium, and cultured at 35 ° C. A solution obtained by diluting the obtained culture solution to about 10 8 cells / ml with a bouillon medium was used as a bacterial solution for inoculation.
In the case of Aspergillus niger, Tween 80 after incubated at 25 ° C. (polyoxyethylene (20) sorbitan monooleate) as prepared in about 10 6 cells / ml suspension of spores 0.2 percent pressurized saline Was used as an inoculum.
（被験物質の希釈系列の調製）
２０ｗ／ｗ％エチルセルソルブを希釈溶媒とし、５ｗ／ｖ％の１，２−オクタンジオール液（母液）を調製した。この母液を倍倍希釈して、１０段階希釈系列を調製した。
また、Ｎ−ヤシ油脂肪酸アシル−Ｌ−アルギニンエチルピロリドンカルボン酸塩（商品名ＣＡＥ、登録商標、味の素株式会社製）及び１，２−オクタンジオールとＮ−ヤシ油脂肪酸アシル−Ｌ−アルギニンエチルピロリドンカルボン酸塩の等重量混合物についても、同様にして、それぞれ１０段階希釈系列を調製した。
(Preparation of dilution series of test substance)
A 20 w / w% ethyl cellosolve was used as a diluent solvent to prepare a 5 w / v% 1,2-octanediol liquid (mother liquid). This mother liquor was diluted twice to prepare a 10-step dilution series.
Further, N-coconut oil fatty acid acyl-L-arginine ethylpyrrolidone carboxylate (trade name CAE, registered trademark, manufactured by Ajinomoto Co., Inc.) and 1,2-octanediol and N-coconut oil fatty acid acyl-L-arginine ethylpyrrolidone Similarly, a 10-step dilution series was prepared for each of the equal weight mixtures of carboxylates.
（最小発育阻止濃度（ＭＩＣ）の測定）
上記被研物質を含む希釈系列を加えた各寒天培地をシャーレに入れ、それぞれについて、上記接種用菌液を約１ｃｍの長さに画線した。
培養は、黄色ブドウ状球菌については、３５℃で培養を行い、２日後の菌の生育の有無を判定した。また、クロカビについては、２５℃で培養を行い、３日後の菌の生育の有無を判定した。このとき、生育の認められなかった最小濃度をＭＩＣとして求めた。その結果、黄色ブドウ状球菌については、１，２−オクタンジオールは２２５０μｇ／ｍｌ、Ｎ−ヤシ油脂肪酸アシル−Ｌ−アルギニンエチルピロリドンカルボン酸塩は１０μｇ／ｍｌ、両者の等量混合物は１０μｇ／ｍｌであった。また、クロカビについては、１，２オクタンジオールは１２５０μｇ／ｍｌ、Ｎ−ヤシ油脂肪酸アシル−Ｌ−アルギニンエチルピロリドンカルボン酸塩は６２５μｇ／ｍｌ、両者の等量混合物は６２５μｇ／ｍｌであった。
尚、最小発育阻止濃度（ＭＩＣ）によって、抗菌力を評価することができる。被験物質の濃度が薄いときには微生物への影響がないが、濃度を増していくと発育抑制が起こる。この程度は、濃度に依存して発育抑制が進み、ついには発育が停止する。そのときの濃度がＭＩＣとして表される。従って、ＭＩＣ以上の濃度になると、微生物は死滅していくことになる。
(Measurement of minimum inhibitory concentration (MIC))
Each agar medium to which the dilution series containing the substance to be studied was added was placed in a petri dish, and the inoculum for the inoculum was streaked to a length of about 1 cm.
The culture was performed at 35 ° C. for Staphylococcus aureus, and the presence or absence of the growth of the bacteria after 2 days was determined. Moreover, about black mold, it culture | cultivated at 25 degreeC and the presence or absence of the growth of a microbe after 3 days was determined. At this time, the minimum concentration at which no growth was observed was determined as MIC. As a result, as for Staphylococcus aureus, 1,2-octanediol was 2250 μg / ml, N-coconut oil fatty acid acyl-L-arginine ethylpyrrolidonecarboxylate was 10 μg / ml, and a mixture of both was 10 μg / ml. Met. As for black mold, 1,2 octanediol was 1250 μg / ml, N-coconut oil fatty acid acyl-L-arginine ethylpyrrolidone carboxylate was 625 μg / ml, and an equivalent mixture of both was 625 μg / ml.
The antibacterial activity can be evaluated by the minimum inhibitory concentration (MIC). There is no effect on microorganisms when the concentration of the test substance is low, but growth inhibition occurs when the concentration is increased. This degree of growth proceeds depending on the concentration, and finally the growth stops. The concentration at that time is expressed as MIC. Therefore, when the concentration is higher than MIC, the microorganisms are killed.
（二元最小発育阻止濃度）
得られた１，２−オクタンジオール、Ｎ−ヤシ油脂肪酸アシル−Ｌ−アルギニンエチルピロリドンカルボン酸塩及び１，２−オクタンジオールとＮ−ヤシ油脂肪酸アシル−Ｌ−アルギニンエチルピロリドンカルボン酸塩の等重量混合物の各ＭＩＣを、１，２−オクタンジオール及びＮ−ヤシ油脂肪酸アシル−Ｌ−アルギニンエチルピロリドンカルボン酸塩の配合量に対してプロットして、二元最小発育阻止濃度図を求めた。結果を図１〜２に示す。
尚、二元最小発育阻止濃度により、抗菌性を有する二種類の物質を配合した場合の作用効果を判定することができる。具体的には、抗菌性を有する二種類の物質を配合した場合、それにより生じる作用は、相乗作用、相加作用、拮抗作用に大別される。相乗作用とは、２薬剤が相乗的に作用し、本来有する抗菌力が更に増強される作用である。相加作用とは、各薬剤の抗菌力が合わさった作用である。拮抗作用とは、１薬剤が他剤の抗菌力を打ち消す場合の作用である。そして、二元最小発育阻止濃度による方法は、例えば図３に示すように、Ａ物質とＢ物質について、それぞれの割合を変えてＭＩＣを測定し、グラフから判定する方法である。これによると、Ａ物質のみにおけるＭＩＣ（点Ａ）とＢ物質のみにおけるＭＩＣ（点Ｂ）とをプロットした点を結び、両物質を併用したときのＭＩＣが、この線上より内側にある場合（点Ｃ）は、併用により抗菌力が増強された相乗作用であると、線上（点Ｄ）にある場合は、相加作用であると、線上より外側にある場合（点Ｅ）は、一方又は双方の抗菌力を打ち消し抗菌力を減少させる拮抗作用であると判定することができる。
(Dual minimum inhibitory concentration)
1,2-octanediol, N-coconut oil fatty acid acyl-L-arginine ethylpyrrolidone carboxylate obtained, 1,2-octanediol and N-coconut oil fatty acid acyl-L-arginine ethylpyrrolidonecarboxylate, etc. Each MIC of the weight mixture was plotted against the blending amount of 1,2-octanediol and N-coconut oil fatty acid acyl-L-arginine ethylpyrrolidone carboxylate to obtain a binary minimum inhibitory concentration diagram. The results are shown in FIGS.
In addition, the effect at the time of mix | blending two types of substances which have antimicrobial property can be determined with a binary minimum growth inhibitory density | concentration. Specifically, when two types of substances having antibacterial properties are blended, the resulting action is roughly classified into synergistic action, additive action, and antagonism. The synergistic action is an action in which two drugs act synergistically to further enhance the inherent antibacterial power. The additive action is an action in which the antibacterial powers of the respective drugs are combined. Antagonism is the action when one drug counteracts the antibacterial activity of another drug. Then, the method using the binary minimum growth inhibitory concentration is a method of determining from the graph by measuring the MIC for each of the A substance and the B substance while changing their ratios as shown in FIG. According to this, when MIC (point A) in only substance A and MIC (point B) only in substance B are connected, the MIC when both substances are used is on the inner side of this line (point C) is a synergistic effect in which antibacterial activity is enhanced by the combined use, when it is on the line (point D), when it is an additive action, when it is outside the line (point E), one or both It can be determined that the antibacterial activity is an antagonism that counteracts the antibacterial activity and decreases the antimicrobial activity.
（抗菌効果の評価）
図１及び図２の結果から、１，２−オクタンジオールとＮ−ヤシ油脂肪酸アシル−Ｌ−アルギニンエチルピロリドンカルボン酸塩とを組み合わせることにより、両者の抗菌力の相乗効果が認められることが分かる。
(Evaluation of antibacterial effect)
From the results of FIG. 1 and FIG. 2, it can be seen that by combining 1,2-octanediol and N-coconut oil fatty acid acyl-L-arginine ethylpyrrolidone carboxylate, a synergistic effect of the antibacterial activity of both is recognized. .
以下、本発明に係る防腐殺菌剤を配合した化粧品、医薬品及び食品の配合例を示す。
＜処方例１：保湿クリーム＞
モノラウリン酸デカグリセリル １．０
モノステアリン酸ＰＯＥ（１５）グリセリル １．０
水素添加大豆リン脂質 １．０
ステアリン酸 ４．０
セタノール ２．０
ベヘニルアルコール ２．０
パラフィン ３．０
スクワラン １２．０
ホホバ油 ４．０
メチルポリシロキサン ０．２
１，３−ブチレングリコール ３．０
Ｌ−アルギニン ０．１
キサンタンガム ０．００１
１，２−オクタンジオール ０．２５
Ｎ−ヤシ油脂肪酸アシル−Ｌ−アルギニン
エチルピロリドンカルボン酸塩 ０．１０
精製水 適 量
合計 １００．０重量％
Hereinafter, formulation examples of cosmetics, pharmaceuticals and foods containing the antiseptic disinfectant according to the present invention will be shown.
<Formulation Example 1: Moisturizing cream>
Decaglyceryl monolaurate 1.0
Monostearic acid POE (15) glyceryl 1.0
Hydrogenated soybean phospholipid 1.0
Stearic acid 4.0
Cetanol 2.0
Behenyl alcohol 2.0
Paraffin 3.0
Squalane 12.0
Jojoba oil 4.0
Methylpolysiloxane 0.2
1,3-butylene glycol 3.0
L-Arginine 0.1
Xanthan gum 0.001
1,2-octanediol 0.25
N-coconut oil fatty acid acyl-L-arginine
Ethylpyrrolidone carboxylate 0.10
Purified water
Total 100.0% by weight
＜処方例２：親水性軟膏＞
アスコルビン酸 ０．５
ポリオキシエチレンセチルエーテル ２．０
水素添加大豆リン脂質 １．０
ステアリン酸 ４．０
グリセリンモノステアレート １０．０
流動パラフィン １０．０
ワセリン ４．０
セタノール ５．０
プロピレングリコール ５．０
１，２−ヘキサンジオール ０．５
Ｎ−ヤシ油脂肪酸アシル−Ｌ−アルギニン
エチルピロリドンカルボン酸塩 ０．２
精製水 適 量
合計 １００．０重量％
<Formulation Example 2: Hydrophilic ointment>
Ascorbic acid 0.5
Polyoxyethylene cetyl ether 2.0
Hydrogenated soybean phospholipid 1.0
Stearic acid 4.0
Glycerol monostearate 10.0
Liquid paraffin 10.0
Vaseline 4.0
Cetanol 5.0
Propylene glycol 5.0
1,2-hexanediol 0.5
N-coconut oil fatty acid acyl-L-arginine
Ethylpyrrolidone carboxylate 0.2
Purified water
Total 100.0% by weight
＜処方例３：飲料＞
ブドウ糖液糖 ３３．０
グレープフルーツ果汁 ６４．０
１，２−ペンタンジオール ０．５
Ｎ−ヤシ油脂肪酸アシル−Ｌ−アルギニン
エチルピロリドンカルボン酸塩 ０．１
香料 ０．５
酸味料 適 量
合計 １００．０重量％
<Prescription Example 3: Beverage>
Glucose liquid sugar 33.0
Grapefruit juice 64.0
1,2-pentanediol 0.5
N-coconut oil fatty acid acyl-L-arginine
Ethylpyrrolidone carboxylate 0.1
Fragrance 0.5
Acidulant appropriate amount
Total 100.0% by weight
Claims (5)
Priority Applications (1)
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Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006070025A (en) * | 2004-08-06 | 2006-03-16 | Eisai Co Ltd | Antiseptic and mildewproofing agent-containing composition |
| EP1772055A1 (en) * | 2005-10-04 | 2007-04-11 | Rohm and Haas France SAS | Synergistic microbicidal compositions comprising a N-alkyl-1,2-benzoisothiazolin-3-one |
| GB0625069D0 (en) * | 2006-12-15 | 2007-01-24 | Givaudan Sa | Compositions |
| US20130053422A1 (en) * | 2010-03-23 | 2013-02-28 | Sarah L. Edmonds | Antimicrobial Compositions |
| WO2014077062A1 (en) * | 2012-11-16 | 2014-05-22 | ライオン株式会社 | Transparent gel-like skin-sterilizing agent |
| JP6773594B2 (en) * | 2017-03-28 | 2020-10-21 | 株式会社マンダム | Skin cosmetics |
| WO2018180315A1 (en) * | 2017-03-28 | 2018-10-04 | 株式会社マンダム | Skin cosmetic |
| JP6773595B2 (en) * | 2017-03-28 | 2020-10-21 | 株式会社マンダム | Skin cosmetics |
| JP6957432B2 (en) * | 2018-09-28 | 2021-11-02 | 株式会社マンダム | Skin cosmetics |
| KR102049844B1 (en) * | 2018-12-28 | 2019-11-28 | 주식회사 명진뉴텍 | Stable liquid composition for preserve of cosmetic comprising PCA ethyl cocoyl arginate |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3996215B2 (en) * | 1993-09-21 | 2007-10-24 | 株式会社資生堂 | Disinfecting composition |
| JPH08157322A (en) * | 1994-12-06 | 1996-06-18 | Rashiinu Kagaku Kk | Cosmetic containing neither antioxidant nor antiseptic specified by pharmaceutical affairs law |
| JPH1095725A (en) * | 1996-09-20 | 1998-04-14 | Noevir Co Ltd | Antibacterial low-stimulation cosmetic |
| JP5062708B2 (en) * | 1998-02-24 | 2012-10-31 | 株式会社マンダム | Antiseptic disinfectant and human body composition |
| JP2003081736A (en) * | 2001-09-14 | 2003-03-19 | Lion Corp | Skin care preparation composition |
| JP2003335621A (en) * | 2002-05-16 | 2003-11-25 | Noevir Co Ltd | Antifungal low irritative cosmetic |
| JP2004043336A (en) * | 2002-07-10 | 2004-02-12 | Naris Cosmetics Co Ltd | Antimicrobial agent and cosmetic incorporated with the same |
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