JP2005213174A - Antiseptic fungicide and cosmetic, medicine, and food compounded with the same - Google Patents
Antiseptic fungicide and cosmetic, medicine, and food compounded with the same Download PDFInfo
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- JP2005213174A JP2005213174A JP2004020635A JP2004020635A JP2005213174A JP 2005213174 A JP2005213174 A JP 2005213174A JP 2004020635 A JP2004020635 A JP 2004020635A JP 2004020635 A JP2004020635 A JP 2004020635A JP 2005213174 A JP2005213174 A JP 2005213174A
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- alkanediol
- antiseptic
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- diol
- cosmetic
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- 230000002421 anti-septic effect Effects 0.000 title claims abstract description 40
- 239000002537 cosmetic Substances 0.000 title claims abstract description 20
- 235000013305 food Nutrition 0.000 title claims abstract description 16
- 239000003814 drug Substances 0.000 title abstract description 22
- 239000000417 fungicide Substances 0.000 title abstract description 8
- 230000000855 fungicidal effect Effects 0.000 title abstract description 6
- 229940031723 1,2-octanediol Drugs 0.000 claims abstract description 15
- AEIJTFQOBWATKX-UHFFFAOYSA-N octane-1,2-diol Chemical compound CCCCCCC(O)CO AEIJTFQOBWATKX-UHFFFAOYSA-N 0.000 claims abstract description 15
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical class OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 claims abstract description 13
- NCZPCONIKBICGS-UHFFFAOYSA-N 3-(2-ethylhexoxy)propane-1,2-diol Chemical compound CCCCC(CC)COCC(O)CO NCZPCONIKBICGS-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 229940015975 1,2-hexanediol Drugs 0.000 claims abstract description 6
- FHKSXSQHXQEMOK-UHFFFAOYSA-N hexane-1,2-diol Chemical compound CCCCC(O)CO FHKSXSQHXQEMOK-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000000645 desinfectant Substances 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000004599 antimicrobial Substances 0.000 claims 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 229940127557 pharmaceutical product Drugs 0.000 claims 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 23
- 239000000203 mixture Substances 0.000 description 15
- 239000000126 substance Substances 0.000 description 11
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- 208000007027 Oral Candidiasis Diseases 0.000 description 4
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- JLPULHDHAOZNQI-ZTIMHPMXSA-N 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Chemical class CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC JLPULHDHAOZNQI-ZTIMHPMXSA-N 0.000 description 2
- JCYHHICXJAGYEL-UHFFFAOYSA-N 3-butoxypropane-1,2-diol Chemical compound CCCCOCC(O)CO JCYHHICXJAGYEL-UHFFFAOYSA-N 0.000 description 2
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- 239000003795 chemical substances by application Substances 0.000 description 2
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- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- NOPFSRXAKWQILS-UHFFFAOYSA-N docosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 description 2
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- 235000019441 ethanol Nutrition 0.000 description 2
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- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 239000002054 inoculum Substances 0.000 description 2
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- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
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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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- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- 229940058015 1,3-butylene glycol Drugs 0.000 description 1
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- SHQRLYGZJPBYGJ-UHFFFAOYSA-N 3-decoxypropane-1,2-diol Chemical compound CCCCCCCCCCOCC(O)CO SHQRLYGZJPBYGJ-UHFFFAOYSA-N 0.000 description 1
- MQVMITUCTLYRNV-UHFFFAOYSA-N 3-hexoxypropane-1,2-diol Chemical compound CCCCCCOCC(O)CO MQVMITUCTLYRNV-UHFFFAOYSA-N 0.000 description 1
- 208000002874 Acne Vulgaris Diseases 0.000 description 1
- 241000228245 Aspergillus niger Species 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
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- 206010014970 Ephelides Diseases 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 1
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- 235000014852 L-arginine Nutrition 0.000 description 1
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- 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
- 239000006096 absorbing agent Substances 0.000 description 1
- 206010000496 acne Diseases 0.000 description 1
- GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 229940064004 antiseptic throat preparations Drugs 0.000 description 1
- 239000003212 astringent agent Substances 0.000 description 1
- 239000000022 bacteriostatic agent Substances 0.000 description 1
- 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
- 235000013361 beverage Nutrition 0.000 description 1
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- 210000003298 dental enamel Anatomy 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
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- 150000004676 glycans Chemical class 0.000 description 1
- YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 1
- SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 1
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- Medicinal Preparation (AREA)
- Cosmetics (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
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、医薬品及び食品に係り、その目的は、１，２−アルカンジオールとグリセリルエーテル誘導体とを有効成分として含有することにより、１，２−アルカンジオールが本来有する抗菌力を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にある。 The present invention relates to an antiseptic disinfectant and cosmetics, pharmaceuticals and foods containing the antiseptic disinfectant. The object of the present invention is to contain 1,2-alkanediol and a glyceryl ether derivative as active ingredients. -It is providing the antiseptic disinfectant which can strengthen the antibacterial power which alkanediol originally has, and the cosmetics, the pharmaceutical, and the foodstuff which mix | blended this antiseptic disinfectant.
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抗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高まり、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%. In addition, since these antiseptic fungicides are easily affected by pH, the stability of the antiseptic disinfection effect is poor, and the antibacterial antibacterial effect may be significantly reduced when used in combination with other components such as surfactants. Also had. In recent years, the number of people who have allergic reactions to these antiseptic disinfectants has increased, so the consumer safety has become more and more important. There is an increasing demand for reduced cosmetics, pharmaceuticals and foods.
そこで、従来の防腐殺菌剤を低減できる技術として、１，２−ペンタンジオールと２−フェノキシエタノールを組み合わせて配合した外用組成物（特許文献１参照）や、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２参照）が開示されている。しかし、これらは、従来の防腐剤と１，２−アルカンジオールを併用して防腐剤の効果を向上させようとするものであって、従来の防腐剤自体を完全に排除しようとするものではなく、また、１，２−アルカンジオールが有する抗菌力を増強させようとするものでもなかった。 Therefore, as a technique capable of reducing the conventional antiseptic disinfectant, an external composition (see Patent Document 1) that is a combination of 1,2-pentanediol and 2-phenoxyethanol, or an antiseptic comprising 1,2-alkanediol and parabens. A disinfectant (see Patent Document 2) is disclosed. However, these are intended to improve the effect of the preservative by using a conventional preservative and 1,2-alkanediol together, and are not intended to completely eliminate the conventional preservative itself. Also, it was not intended to enhance the antibacterial activity of 1,2-alkanediol.
一方、従来の防腐殺菌剤を排除できる技術として、１，２−アルカンジオールからなる防腐殺菌剤（特許文献３参照）や、１，２−オクタンジオールからなる洗浄性又は非洗浄性化粧料用保湿静菌剤（特許文献４参照）などが開示されている。しかし、１，２−オクタンジオールなどの１，２−アルカンジオールを単独で防腐殺菌剤として用いた場合、充分な効果性を得るためには高配合量を必要とする場合があり、また、１，２−アルカンジオールは特有の原料臭を有することから、低配合量でも充分な防腐殺菌効果を発揮できる技術が望まれている。 On the other hand, as a technique that can eliminate the conventional antiseptic disinfectant, an antiseptic disinfectant composed of 1,2-alkanediol (see Patent Document 3) and a moisturizing agent for cleansing or non-detergency cosmetics composed of 1,2-octanediol. A bacteriostatic agent (see Patent Document 4) and the like are disclosed. However, when 1,2-alkanediol such as 1,2-octanediol is used alone as an antiseptic disinfectant, a high blending amount may be required to obtain sufficient effectiveness. Since 2-alkanediol has a peculiar raw material odor, a technology capable of exhibiting a sufficient antiseptic sterilization effect even at a low blending amount is desired.
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、グリセリルエーテル誘導体とを有効成分として共に用い、１，２−アルカンジオールが本来有する抗菌力を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 uses 1,2-alkanediol and a glyceryl ether derivative together as active ingredients to enhance the antibacterial activity inherent in 1,2-alkanediol. It is an object of the present invention to provide an antiseptic disinfectant that can be prepared, and cosmetics, pharmaceuticals, and foods containing the antiseptic disinfectant.
すなわち、請求項１に係る発明は、式（１）：
Ｒ１−ＣＨ（ＯＨ）−ＣＨ２−ＯＨ （１）
（式中、Ｒ１は炭素数３〜８のアルキル基を表す。）
で表される１，２−アルカンジオールと、式（２）：
Ｒ２−Ｏ−ＣＨ２−ＣＨ（ＯＨ）−ＣＨ２−ＯＨ （２）
（式中、Ｒ２は直鎖又は分枝鎖の炭素数３〜１４のアルキル基を表す。）
で表されるグリセリルエーテル誘導体とを含有することを特徴とする防腐殺菌剤に関する。
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、前記グリセリルエーテル誘導体が、３−（２−エチルヘキシルオキシ）プロパン−１，２−ジオールであることを特徴とする請求項１又は２に記載の防腐殺菌剤に関する。
請求項４に係る発明は、防腐殺菌剤として請求項１〜３のいずれかに記載の防腐殺菌剤を配合したことを特徴とする化粧料、医薬品又は食品に関する。
That is, the invention according to claim 1 provides the formula (1):
R 1 —CH (OH) —CH 2 —OH (1)
(In the formula, R 1 represents an alkyl group having 3 to 8 carbon atoms.)
1,2-alkanediol represented by the formula (2):
R 2 -O-CH 2 -CH ( OH) -CH 2 -OH (2)
(In the formula, R 2 represents a linear or branched alkyl group having 3 to 14 carbon atoms.)
And a glyceryl ether derivative represented by the formula:
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 disinfectant according to claim 1 or 2, wherein the glyceryl ether derivative is 3- (2-ethylhexyloxy) propane-1,2-diol.
The invention which concerns on Claim 4 is related with the cosmetics, the pharmaceutical, or the foodstuff which mix | blended the antiseptic disinfectant in any one of Claims 1-3 as an antiseptic disinfectant.
本発明の防腐殺菌剤は、１，２−アルカンジオールが本来有する抗菌力を増強させるという効果を奏する。また、本発明に係る防腐殺菌剤を配合した化粧料、医薬品及び食品は、サリチル酸、安息香酸、パラベンなどの従来の防腐殺菌剤を含有する必要がなく、しかも本発明に係る防腐殺菌剤は優れた抗菌活性を有しているので、防腐殺菌剤自体を低配合とすることができるという効果を奏する。 The antiseptic disinfectant of the present invention has the effect of enhancing the antibacterial activity inherent to 1,2-alkanediol. Further, cosmetics, pharmaceuticals and foods containing the antiseptic disinfectant according to the present invention do not need to contain conventional antiseptic disinfectants such as salicylic acid, benzoic acid and parabens, and the antiseptic disinfectant according to the present invention is excellent. Since the antibacterial activity is high, the preservative disinfectant itself can be made low.
本発明に係る防腐殺菌剤は、１，２−アルカンジオールとグリセリルエーテル誘導体を有効成分として含有する。 The antiseptic fungicide according to the present invention contains 1,2-alkanediol and a glyceryl ether derivative as active ingredients.
本発明に用いられる１，２−アルカンジオールとしては、下記式（１）：
Ｒ１−ＣＨ（ＯＨ）−ＣＨ２−ＯＨ （１）
（式中、Ｒ１は炭素数３〜８のアルキル基を表す。）
で表される１，２−アルカンジオールが用いられる。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−デカンジオールが挙げられ、これらのうち、１，２−ヘキサンジオール、１，２−オクタンジオールを用いるのが好ましく、１，２−オクタンジオールを用いるのがより好ましい。尚、本発明においては、これらの１種を単独で、又は２種以上を組み合わせて用いることもできる。
As the 1,2-alkanediol used in the present invention, the following formula (1):
R 1 —CH (OH) —CH 2 —OH (1)
(In the formula, R 1 represents an alkyl group having 3 to 8 carbon atoms.)
The 1,2-alkanediol represented by these is used. Specific examples include 1,2-pentanediol, 1,2-hexanediol, 1,2-heptanediol, 1,2-octanediol, 1,2-nonanediol, and 1,2-decanediol. Of these, 1,2-hexanediol and 1,2-octanediol are preferably used, and 1,2-octanediol is more preferably used. In addition, in this invention, these 1 type can also be used individually or in combination of 2 or more types.
本発明に用いられるグリセリルエーテル誘導体としては、下記式（２）：
Ｒ２−Ｏ−ＣＨ２−ＣＨ（ＯＨ）−ＣＨ２−ＯＨ （２）
（式中、Ｒ２は直鎖又は分枝鎖の炭素数３〜１４のアルキル基を表す。）
で表されるグリセリルエーテル誘導体が用いられる。具体的には、３−ｎ−ブトキシプロパン−１，２−ジオール、３−ｉ−ブトキシプロパン−１，２−ジオール、３−ｎ−ヘキシルオキシプロパン−１，２−ジオール、３−ｎ−オクチルオキシプロパン−１，２−ジオール、３−（２−エチルヘキシルオキシ）プロパン−１，２−ジオール、３−ｎ−デシルオキシプロパン−１，２−ジオール等を挙げることができ、３−（２−エチルヘキシルオキシ）プロパン−１，２−ジオールを用いるのが好ましい。尚、本発明においては、これらの１種を単独で、又は２種以上を組み合わせて用いることもできる。
As the glyceryl ether derivative used in the present invention, the following formula (2):
R 2 -O-CH 2 -CH ( OH) -CH 2 -OH (2)
(In the formula, R 2 represents a linear or branched alkyl group having 3 to 14 carbon atoms.)
The glyceryl ether derivative represented by these is used. Specifically, 3-n-butoxypropane-1,2-diol, 3-i-butoxypropane-1,2-diol, 3-n-hexyloxypropane-1,2-diol, 3-n-octyl Examples include oxypropane-1,2-diol, 3- (2-ethylhexyloxy) propane-1,2-diol, 3-n-decyloxypropane-1,2-diol, and the like. Ethylhexyloxy) propane-1,2-diol is preferably used. In addition, in this invention, these 1 type can also be used individually or in combination of 2 or more types.
本発明に係る防腐殺菌剤においては、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グリセリルエーテル誘導体の含有量は特に限定されないが、重量比で０．１：１〜１０：１、好ましくは０．２：１〜５：１となるように配合する。１，２−アルカンジオールをグリセリルエーテル誘導体の含有量の１０重量倍を超えて配合すると、また０．１重量倍未満の場合、抗菌力の増強効果が期待できないために好ましくない。 In the antiseptic fungicide according to the present invention, the content of the 1,2-alkanediol as the first component and the glyceryl ether derivative as the second component is not particularly limited, but is 0.1: 1 to 1 by weight. It mix | blends so that it may become 10: 1, preferably 0.2: 1-5: 1. If 1,2-alkanediol is added in an amount exceeding 10 times the content of the glyceryl ether derivative, and if it is less than 0.1 times, an antibacterial activity enhancing effect cannot be expected, such being undesirable.
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、第二の成分であるグリセリルエーテル誘導体とを含有するから、後述する実施例に示されるように、第一の成分と第二の成分との相乗効果によって、抗菌力の優れた増強作用が発揮される。したがって、パラベン、安息香酸類、サリチル酸類のような従来から用いられる防腐殺菌剤を低配合又は配合する必要がなく、極めて安全性の高い防腐殺菌剤を得ることができる。 Since the antiseptic disinfectant according to the present invention contains 1,2-alkanediol as the first component and the glyceryl ether derivative as the second component, as shown in the examples described later, Due to the synergistic effect of this component and the second component, an excellent antibacterial activity is exerted. Therefore, it is not necessary to blend or blend conventionally used antiseptics such as parabens, benzoic acids, and salicylic acids, and a highly safe antiseptic can be obtained.
本発明の防腐殺菌剤は、化粧料、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、洗顔剤、化粧水、乳液、スキンクリーム、ファンデーション、マスカラ、ネールエナメル、口紅等の皮膚用化粧料、シャンプー、ヘアトリートメント、育毛・養毛剤、ヘアクリーム、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、トローチ等の医薬品、チューインガム、キャンディー、飲料水等の食品に好適に用いることができる。 The antiseptic disinfectant of the present invention can be used by blending it in cosmetics, pharmaceuticals, foods and the like. Specifically, facial cleanser, lotion, milky lotion, skin cream, foundation, mascara, nail enamel, lipstick and other skin cosmetics, shampoo, hair treatment, hair growth / hair restorer, hair cream, hair foam, permanent wave agent, etc. Cosmetics for specific hair use such as hair cosmetics, stains and freckles (quasi-drugs), acne medicines, gargles, lozenges, and other foods such as chewing gum, candy, and drinking water It can be used suitably.
本発明の防腐殺菌剤を用いて化粧料、医薬品又は食品を調製する場合、本発明の効果を損なわない範囲内であれば、化粧料、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、化粧料（医薬部外品を含む）や医薬品の場合、油脂、ロウ類、高級脂肪酸、低級アルコール、高級アルコール、ステロール類、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、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、精製水等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、ガムベース等を例示することができる。 When preparing cosmetics, pharmaceuticals or foods using the antiseptic disinfectant of the present invention, the components usually used in cosmetics, pharmaceuticals or foods are optionally arbitrarily blended as long as the effects of the present invention are not impaired. be able to. For example, in the case of cosmetics (including quasi-drugs) and pharmaceuticals, fats and oils, waxes, higher fatty acids, lower alcohols, higher alcohols, sterols, fatty acid esters, humectants, surfactants, polymer compounds, inorganic pigments , Pigments, antioxidants, ultraviolet absorbers, vitamins, astringents, whitening agents, animal and plant extracts, sequestering agents, purified water, and the like. In the case of food, animal and vegetable oils, polysaccharides, sweeteners, colorants, gum bases and the like can be exemplified.
化粧料、医薬品又は食品に本発明の防腐殺菌剤を配合する場合、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％である。配合量が０．０１重量％未満の場合、抗菌効果に劣るために、また、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からである。 When the antiseptic disinfectant of the present invention is blended in cosmetics, pharmaceuticals or foods, the blending amount is not particularly limited, but is 0.01 to 20% by weight, preferably 0.05 to 5% by weight in the composition. This is because when the amount is less than 0.01% by weight, the antibacterial effect is inferior, and even if the amount exceeds 20% by weight, no further effect can be expected.
実施例１
（共試菌）
共試菌としてStaphylococcus aureus IFO13276（黄色ブドウ状球菌）、Candida albicans IFO1594（口腔カンジダ症菌）及びAspergillus niger IFO9455（クロカビ）を用いた。
Example 1
(Co-test)
Staphylococcus aureus IFO13276 (Staphylococcus aureus), Candida albicans IFO1594 (oral candidiasis) and Aspergillus niger IFO9455 (black mold) were used as co-test bacteria.
（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、口腔カンジダ症菌の場合、３０℃で同様に培養して約１０７個／ｍｌに希釈したものを、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）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)
As a bacterial solution for inoculation, in the case of Staphylococcus aureus, after culturing at 35 ° C. on an agar medium, it was further 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 oral candidiasis, the same culture at 30 ° C. and diluted to about 10 7 cells / ml are used. In the case of black mold, Tween 80 (polyoxyethylene (20) sorbitan mono) is cultured at 25 ° C. (Oleate) What was prepared by suspending spores in 2% physiological saline to prepare about 10 6 cells / ml was used as a bacterial solution for inoculation.
（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、５、４、３、２．５、２．２５、２、１．７５、１．５、１．２５、１ｗ／ｖ％の１，２−オクタンジオール液を調製した。
また、３−（２−エチルヘキシルオキシ）プロパン−１，２−ジオール（商品名 Sensiva SC50、成和化成社製）及び１，２−オクタンジオールと３−（２−エチルヘキシルオキシ）プロパン−１，２−ジオールの等量混合物については、５ｗ／ｖ％の液を倍倍希釈して希釈系列を調製した。
(Preparation of dilution series of test substance)
5, 4-, 3, 2.5, 2.25, 2, 1.75, 1.5, 1.25, 1 w / v% 1,2-octane using 20 w / w% ethyl cellosolve as a diluent solvent A diol solution was prepared.
Moreover, 3- (2-ethylhexyloxy) propane-1,2-diol (trade name Sensiva SC50, manufactured by Seiwa Kasei Co., Ltd.) and 1,2-octanediol and 3- (2-ethylhexyloxy) propane-1,2 -For an equal volume mixture of diols, a dilution series was prepared by doubling a 5 w / v% solution.
（最小発育阻止濃度（ＭＩＣ）の測定）
上記被験物質を含む希釈系列１ｍＬに対して各寒天培地９ｍＬ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℃で行い、２日後の菌の生育の有無を判定した。また、口腔カンジダ症菌及び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、生育が認められなかった最小の濃度をＭＩＣとして求めた。結果を表１に示す。
(Minimum inhibitory concentration (MIC) measurement)
For each 1 mL of the dilution series containing the test substance, 9 mL of each agar medium 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. In addition, oral candidiasis bacteria and black mold were cultured at 25 ° C., and the presence or absence of growth of the bacteria after 3 days was determined. At this time, the minimum concentration at which no growth was observed was determined as MIC. The results are shown in Table 1.
尚、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はないが、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。このときの濃度がＭＩＣとして表される。したがって、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。 In addition, antibacterial power can be evaluated by 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 this 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、３−（２−エチルヘキシルオキシ）プロパン−１，２−ジオール、及び１，２−オクタンジオールと３−（２−エチルヘキシルオキシ）プロパン−１，２−ジオールの等重量混合物の各ＭＩＣを、１，２−オクタンジオール及び３−（２−エチルヘキシルオキシ）プロパン−１，２−ジオールの配合量に対してプロットし、二元最小発育阻止濃度図を求めた。結果を図１〜図３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、それにより生ずる作用は、相乗作用、相加作用、拮抗作用に大別される。相乗作用とは、二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、一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図による方法は、例えば、図４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, 3- (2-ethylhexyloxy) propane-1,2-diol, and 1,2-octanediol and 3- (2-ethylhexyloxy) propane-1,2-diol obtained Each MIC of the equal weight mixture was plotted with respect to the blending amounts of 1,2-octanediol and 3- (2-ethylhexyloxy) propane-1,2-diol to obtain a binary minimum growth 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 action caused by the substances is roughly classified into a synergistic action, an additive action, and an antagonistic action. 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 an action when one drug counteracts the antibacterial activity of another drug. Then, the method based on the binary minimum growth inhibition concentration diagram is a method of determining from the graph by measuring the MIC for each of the A substance and B substance while changing their ratios as shown in FIG. According to this, when MIC (point A) only for substance A and MIC (point B) only for 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 the antibacterial activity is enhanced by the combined use, if it is on the line (point D), if it is an additive action, if it is outside the line (point E), one or both It can be determined that the antagonistic action counteracts the antibacterial activity and decreases the antibacterial activity.
（抗菌効果の評価）
図１〜図３の結果から、１，２−オクタンジオールと３−（２−エチルヘキシルオキシ）プロパン−１，２−ジオールとの組合せにより、抗菌力の相乗効果が認められた。
(Evaluation of antibacterial effect)
From the result of FIGS. 1-3, the synergistic effect of antibacterial activity was recognized by the combination of 1,2-octanediol and 3- (2-ethylhexyloxy) propane-1,2-diol.
以下、本発明の防腐殺菌剤を配合した化粧料、医薬品及び食品の配合例を示す。尚、配合量は重量％である。
（配合例１：保湿クリーム）
モノラウリン酸デカグリセリル 1.0
モノステアリン酸ポリオキシエチレン（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
３−（２−エチルヘキシルオキシ）プロパン−１，２−ジオール 0.1
精製水 残分
合 計 100.0
Hereinafter, formulation examples of cosmetics, pharmaceuticals and foods containing the antiseptic disinfectant of the present invention will be shown. In addition, a compounding quantity is weight%.
(Formulation example 1: moisturizing cream)
Decaglyceryl monolaurate 1.0
Polyoxyethylene (15) glyceryl monostearate 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
Methyl polysiloxane 0.2
1,3-butylene glycol 3.0
L-Arginine 0.1
Xanthan gum 0.001
1,2-octanediol 0.25
3- (2-Ethylhexyloxy) propane-1,2-diol 0.1
Purified water residue
Total 100.0
（配合例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
３−（２−エチルヘキシルオキシ）プロパン−１，２−ジオール 0.2
精製水 残分
合 計 100.0
(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
3- (2-Ethylhexyloxy) propane-1,2-diol 0.2
Purified water residue
Total 100.0
（配合例３：飲料）
アスコルビン酸 0.5
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
３−（２−エチルヘキシルオキシ）プロパン−１，２−ジオール 0.1
酸味料 適量
合 計 100.0
(Formulation Example 3: Beverage)
Ascorbic acid 0.5
Glucose liquid sugar 33.0
Grapefruit juice 64.0
1,2-pentanediol 0.5
3- (2-Ethylhexyloxy) propane-1,2-diol 0.1
Sour seasoning
Total 100.0
本発明の防腐殺菌剤は、１，２−アルカンジオールが本来有する抗菌力を増強して優れた抗菌活性を有するとともに、高い安全性を有しているので、化粧料、医薬品及び食品などの防腐殺菌剤として好適に用いることができる。 The antiseptic disinfectant of the present invention enhances the antibacterial activity inherent to 1,2-alkanediol and has an excellent antibacterial activity, as well as high safety. It can be suitably used as a disinfectant.
Claims (4)
Ｒ１−ＣＨ（ＯＨ）−ＣＨ２−ＯＨ （１）
（式中、Ｒ１は炭素数３〜８のアルキル基を表す。）
で表される１，２−アルカンジオールと、式（２）：
Ｒ２−Ｏ−ＣＨ２−ＣＨ（ＯＨ）−ＣＨ２−ＯＨ （２）
（式中、Ｒ２は直鎖又は分枝鎖の炭素数３〜１４のアルキル基を表す。）
で表されるグリセリルエーテル誘導体とを含有することを特徴とする防腐殺菌剤。 Formula (1):
R 1 —CH (OH) —CH 2 —OH (1)
(In the formula, R 1 represents an alkyl group having 3 to 8 carbon atoms.)
1,2-alkanediol represented by the formula (2):
R 2 -O-CH 2 -CH ( OH) -CH 2 -OH (2)
(In the formula, R 2 represents a linear or branched alkyl group having 3 to 14 carbon atoms.)
And a glyceryl ether derivative represented by the formula:
A cosmetic, pharmaceutical product or food comprising the antiseptic agent according to any one of claims 1 to 3 as an antiseptic agent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2004020635A JP4294505B2 (en) | 2004-01-29 | 2004-01-29 | Antiseptic disinfectant and cosmetics, pharmaceuticals and foods containing the antiseptic disinfectant |
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| Application Number | Priority Date | Filing Date | Title |
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| JP2004020635A JP4294505B2 (en) | 2004-01-29 | 2004-01-29 | Antiseptic disinfectant and cosmetics, pharmaceuticals and foods containing the antiseptic disinfectant |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005213174A true JP2005213174A (en) | 2005-08-11 |
| JP4294505B2 JP4294505B2 (en) | 2009-07-15 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
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| JP (1) | JP4294505B2 (en) |
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| JP2007131594A (en) * | 2005-11-11 | 2007-05-31 | Adeka Corp | Antibacterial composition and cosmetic and cleanser each containing the same |
| JP2007145748A (en) * | 2005-11-28 | 2007-06-14 | Mandom Corp | Antiseptic sterilizer, cosmetic or medicine containing the antiseptic sterilizer, and method for antiseptic sterilization |
| DE102007017851A1 (en) * | 2007-04-16 | 2008-10-23 | Schülke & Mayr GmbH | Composition based on glycerol ether / polyol mixtures |
| US8933134B2 (en) | 2010-06-09 | 2015-01-13 | L'oreal | Compositions containing agar and a softening agent |
| WO2015125392A1 (en) * | 2014-02-24 | 2015-08-27 | 株式会社Adeka | Skin cosmetic composition, antibacterial agent for skin cosmetic, and method for enhancing antibacterial effect of diol compound |
| KR101779131B1 (en) | 2015-06-25 | 2017-09-19 | 주식회사 엑티브온 | A preservative for skin external application, and a cosmetic composition and a pharmaceutical composition comprising the same |
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| WO2018221337A1 (en) * | 2017-05-30 | 2018-12-06 | 株式会社Adeka | Antimicrobial composition |
| KR20190143616A (en) * | 2018-06-21 | 2019-12-31 | 아데카코리아 주식회사 | Cosmetic compositions containing poly(butyl cyanoacrylate) |
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2004
- 2004-01-29 JP JP2004020635A patent/JP4294505B2/en not_active Expired - Lifetime
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007131594A (en) * | 2005-11-11 | 2007-05-31 | Adeka Corp | Antibacterial composition and cosmetic and cleanser each containing the same |
| JP2007145748A (en) * | 2005-11-28 | 2007-06-14 | Mandom Corp | Antiseptic sterilizer, cosmetic or medicine containing the antiseptic sterilizer, and method for antiseptic sterilization |
| DE102007017851A1 (en) * | 2007-04-16 | 2008-10-23 | Schülke & Mayr GmbH | Composition based on glycerol ether / polyol mixtures |
| JP2008266332A (en) * | 2007-04-16 | 2008-11-06 | L'air Liquide Sante Internatl | Composition based on glycerol ether/polyol mixtures |
| EP1992327A1 (en) * | 2007-04-16 | 2008-11-19 | Air Liquide Santé (International) | Composition based on glycerol ether/polyol mixtures |
| EP2316410A3 (en) * | 2007-04-16 | 2011-06-22 | Air Liquide Santé (International) | Composition based on glycerol ether/polyol mixtures |
| US8058218B2 (en) * | 2007-04-16 | 2011-11-15 | Air Liquide Sante (International) | Composition based on glycerol ether/polyol mixtures |
| US8093193B2 (en) * | 2007-04-16 | 2012-01-10 | Air Liquide Sante (International) | Composition based on glycerol ether/polyol mixtures |
| US8933134B2 (en) | 2010-06-09 | 2015-01-13 | L'oreal | Compositions containing agar and a softening agent |
| WO2015125392A1 (en) * | 2014-02-24 | 2015-08-27 | 株式会社Adeka | Skin cosmetic composition, antibacterial agent for skin cosmetic, and method for enhancing antibacterial effect of diol compound |
| JPWO2015125392A1 (en) * | 2014-02-24 | 2017-03-30 | 株式会社Adeka | Skin cosmetic composition, antibacterial agent for skin cosmetic and method for enhancing antibacterial effect of diol compound |
| KR101779131B1 (en) | 2015-06-25 | 2017-09-19 | 주식회사 엑티브온 | A preservative for skin external application, and a cosmetic composition and a pharmaceutical composition comprising the same |
| JP2017178787A (en) * | 2016-03-28 | 2017-10-05 | 株式会社マンダム | Emulsion cosmetic and sheet cosmetic |
| WO2018221337A1 (en) * | 2017-05-30 | 2018-12-06 | 株式会社Adeka | Antimicrobial composition |
| JPWO2018221337A1 (en) * | 2017-05-30 | 2020-04-02 | 株式会社Adeka | Antimicrobial composition |
| JP7178996B2 (en) | 2017-05-30 | 2022-11-28 | 株式会社Adeka | antibacterial composition |
| KR20190143616A (en) * | 2018-06-21 | 2019-12-31 | 아데카코리아 주식회사 | Cosmetic compositions containing poly(butyl cyanoacrylate) |
| KR102093827B1 (en) * | 2018-06-21 | 2020-03-26 | 아데카코리아 주식회사 | Cosmetic compositions containing poly(butyl cyanoacrylate) |
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