JP5587094B2 - マイコバクテリアを制御するための、芳香族アルコールとグリセロールエーテルの混合液に基づく相乗的製剤 - Google Patents
マイコバクテリアを制御するための、芳香族アルコールとグリセロールエーテルの混合液に基づく相乗的製剤 Download PDFInfo
- Publication number
- JP5587094B2 JP5587094B2 JP2010178007A JP2010178007A JP5587094B2 JP 5587094 B2 JP5587094 B2 JP 5587094B2 JP 2010178007 A JP2010178007 A JP 2010178007A JP 2010178007 A JP2010178007 A JP 2010178007A JP 5587094 B2 JP5587094 B2 JP 5587094B2
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- Prior art keywords
- fungicide
- component
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- glycerol ether
- weight
- Prior art date
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- Expired - Lifetime
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- 239000000203 mixture Substances 0.000 title claims description 36
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- 230000002195 synergetic effect Effects 0.000 title description 5
- RBNPOMFGQQGHHO-UHFFFAOYSA-N glyceric acid Chemical compound OCC(O)C(O)=O RBNPOMFGQQGHHO-UHFFFAOYSA-N 0.000 title description 2
- 239000000417 fungicide Substances 0.000 claims description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 28
- 230000000855 fungicidal effect Effects 0.000 claims description 18
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- OOWQBDFWEXAXPB-IBGZPJMESA-N 1-O-hexadecyl-sn-glycerol Chemical compound CCCCCCCCCCCCCCCCOC[C@@H](O)CO OOWQBDFWEXAXPB-IBGZPJMESA-N 0.000 description 1
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- UJTVNVOGXIDHEY-UHFFFAOYSA-N 2,3-dibromo-2,3-dimethylbutanedinitrile Chemical compound BrC(C(C)(C#N)Br)(C)C#N UJTVNVOGXIDHEY-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/02—Acyclic compounds
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- A—HUMAN NECESSITIES
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- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/04—Oxygen or sulfur attached to an aliphatic side-chain of a carbocyclic ring system
-
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- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
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- A61L2/00—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor
- A61L2/16—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor using chemical substances
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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Description
芳香族アルコールは、対応する作用を達成するために非常に大量に使用しなければならず、物質適合性において害をさらに増加させる。さらに、N,N-置換されたグリシン誘導体は、マイコバクテリア殺菌性の活性化合物として記載されているが(DE-A-19801821を参照)、これらの活性化合物は、泡を生じる傾向を有し、多量に適用することは望ましくない。
? 腐食をせず、または著しく腐食をせず、病院部門で使用される物質であり、殺菌しなければならず、および
? ヒト皮膚と接触しても刺激活性を有さず、且つ脱脂活性を有さない(すなわち、エタノールまたはイソプロパノールなどの低級アルコールを高含量で有する必要がない)。
-アルキルを有する1-モノアルキルグリセロールエーテルであり、特に好ましくは、飽和した、および枝分れしたC6-〜C12-アルキルである。特に非常に好ましくは、1-(2-エチルヘキシル)グリセロールエーテル(Sensiva(R) SC 50)である。
1)殺生物剤分散剤、農業部門における分散剤、殺虫剤製剤、ポリマー分散剤、接着剤、増粘剤、色素、塗料、色素拡散剤、写真感光材料(たとえば顕色液)などの原体、
2)たとえば、局所的適用のための、または太陽保護製品、湿性布、膜形成性の性質を有するポリマー製剤、ねり歯みがき、介護製品、メイキャップ、口紅、マニキュア液などの塗っておく製品もしくは洗い流せる製品(leave-onもしくはrinse-off製品)としての、皮膚病用および化粧用の製品、
3)等張液、薬剤およびワクチンなどの製剤、並びに
4)脱臭剤、足脱臭剤、アルコール性のスプレー殺菌剤およびマニュアルで機器クリーニングするための組成物などの殺菌剤製品。
i)皮膚、粘膜、傷、植物、植物部分などの生物物質、
ii)コンタクトレンズまたは創傷包帯などの、皮膚、粘膜または傷と接触する物質、
iii)医用器具、医療機器(たとえば内視鏡)などの表面、または床および手術台などの表面。
-該殺菌剤は、安価な成分から製造される。
以下の省略記号を使用した:
SC 50 1-(2-エチルヘキシル)グリセロールエーテル
Sensiva SC 50
水 脱塩水
エタノール エタノール、メチルエチルケトンで変性させた
POE フェノキシエタノール
明確に定めていなければ、全てのパーセンテージは、重量のパーセントである。
種々の水性の殺菌剤を、マイコバクテリウム・テラに対するそれらの活性に関し、1〜3×109の細胞数で、負荷のない定量的懸濁液試験において試験した。以下の減衰因子を測定した。減衰因子が>5では、充分なTb活性に対応する。試験のために、種々の量のエタノールを水性の活性化合物溶液に添加して、15、30および60分間暴露した後に試験した。結核菌撲滅性の活性を試験するために、1997年4月30日のDeutsche Gesellscaft fur Hygiene und Mikrobiologie [German Society for Hygiene and Microbiology](Hyg.med. 22、1997(isue6)、pages 278ff)に従って、定量的懸濁液試験マイコバクテリウム・テラ(ATCC15755)を使
用した。
B) 水中に0.1%のSC 50
C) 水中に1.5%のPOE
D) 水中に0.1%のSC 50 +1.5%のPOE
結果:
結核症細菌は危険性であるため、結核菌(Mycobacterium tuberculosis)における試験は実施しなかった。しかし、結核菌とマイコバクテリウム・テラは非常に構造上類似しているため、上記結果は、マイコバクテリウム・テラにおける活性試験は、結核菌に対する活性の情報を提供することができる。
Koko試験において、製品としてリンゲル液を使用し、以下の水性作用溶液を調査した:
分析原理
記載された方法を使用して、化粧製剤のためのパッケージ防腐剤に関し、化学物的な防腐剤の活性を試験した。試験では、種々の実験バッチ内で、種々の濃度の試験下において、防腐剤を保存加工していないサンプルに添加した。連続的な微生物の負荷は、実験バッチに周期的に接種することによって実施した。接種と平行して、それぞれの場合の直前に、個々のバッチの画線サンプルを得た。画線サンプルの微生物の増殖に基づいて評価を作製した。防腐剤の効果があるほど、微生物増殖が最初に出現する期間は長くなる。
CSA(カゼインペプトン−大豆ベプトンアガー)
SA(サブロー寒天培地)
SAスロープチューブ
CSA+TLSH(No.4)
SA−TLSH(No.10)
NaCl(生理食塩水、8.5%)
使用した試験生物は、以下の4つの試験生物群の混合懸濁液(5群)である。
細菌:CSアガーに無菌のガラス棒で画線。
細菌は、それぞれの場合において5mlのNaCl溶液に懸濁し、100mlのメスシリンダにガラスウールを含んでいるガラス漏斗を通して濾過し、NaClで100mlにする。細菌懸濁液は、約109CFU/mlの力価を有する。
3種のクロカビのスロープチューブを、Heldolph攪拌機においてそれぞれ3mlのNaCl溶液と共に振とうし、ガラスウールを含むガラス漏斗を通した。酵母鵞口瘡カンジダ(Candida albicans)は、5mlのNaC1と懸濁して、また、ガラス漏斗を通して注ぐ。5mlのペニシラム・フニクロサム(Penicillium funiculosum)懸濁液(菌類の懸濁液の標品のための解析手順番号22を参照)をこの混合液に添加して、混合液をNaClで100mlにする。真菌懸濁液は、約105-9CFU/mlの力価を有する。
実際に使用した接種溶液は、上記の通りに調製する(1〜4群)。懸濁後、これを混合して、NaClで100mlにするだけである。
別々のバッチに、それぞれの場合において、試験下の化粧品25gを、異なった濃度で試験下の防腐剤と混合する。保存加工されていない製品サンプルは、それぞれの場合において増殖のコントロールとして使用する。滅菌したガラス棒を使用して試験バッチをCSA/TLSHおよびSa/TLSHの上へ画線し、週に一度十分に攪拌した後、新たな接種の直前に最初の画線を行った。全てのサンプルに0.1mlの各微生物の懸濁液を接種して、十分に撹拌する。
本発明の殺菌剤は、Koko試験において成分(a)および(b)の相乗的作用を示す。
本発明の殺菌剤の胞子に対する活性は、H202の添加により増加させることができる。
細菌および酵母真菌に対する殺菌剤の活性。
4A 水中に0.1%のSC 50
4B 水中に1.5%のPOE
4C 水中に0.1%のSC 50の+ 1.5%のPOE
これらの製剤を使用して、以下の減衰因子を得た(SA=黄色ブドウ球菌(Staphylococcus aureus)、PS=緑膿菌(Pseudomonas aeruginosa)、EC =大腸菌(Escherichia coli)、PM =プロテウス・メラビリス(Proteus merabilis)およびCA=鵞口瘡カンジダ(Candida albicans))。この場合、水で50%および25%に希釈ものについても実験した(最初の細胞数0.8〜5×109/ml、CAでは2×107/ml(脱阻害(deinhibition) Tryp-NaCL TLSH(番号22))。
0.1mlのCSLの微生物懸濁液を、10mlの試験下(標準化された硬度(WSH)の水溶液)の殺菌剤希釈液と室温で十分に混合する。5、15、30および60分間暴露した後、それぞれの場合において、1mlを殺菌剤/微生物の混合液から取りだして、9mlの不活性化液(0.1%のトリプトン+0.85%のNaClの二回蒸留水+不活性化物質)に接種する。長くとも30分間不活性化液に接触させた後、希釈液(10-2および10-4の0.1%トリプトン溶液+0.85% NaClの二回蒸留水溶液)を作製する。次いで、0.1mlの各不活性化液および2種の希釈液をそれぞれ3つのCSAプレート上にまく。コントロールとして、殺菌剤の代わりにそれぞれの固形微生物懸濁液を10mlのWSHと混合する。対応する暴露時間と並行して、同様の方法でこのバッチからサブカルチャーを作成する。
基準溶液と比較して、本発明の組成物は、改良された活性を示す。30%の水だけを含む基準溶液と比較して、本発明の作用溶液(5d)は64%の水を含む。したがって、本発明の製剤は、皮膚に対してより適合性を有する。本発明によらない製剤5Bとの比較から、POEと組み合わせることにより、比較的高価なSC 50の一部を置換することができ、この組合せは、活性を改善する結果にさえなる。
Claims (6)
- 作用混合物の形態または濃縮物の形態の殺菌剤であって、
(a)1-(2-エチルヘキシル)グリセロールエーテル、および
(b)3-フェニルプロパン1-オル、フェニルエチルアルコール、ベラトリルアルコール、ベンジルアルコールまたは2-メチル-1-フェニール-2-プロパノールから選ばれる1または複数のアリールアルカノール
を含み、成分(b)に対する成分(a)の重量比xが0.15以下である殺菌剤。 - 請求項1に記載の殺菌剤であって、
成分(b)に対する成分(a)の重量比xが、0.09以下であることを特徴とする殺菌剤。 - 請求項1に記載の殺菌剤であって、
成分(b)に対する成分(a)の重量比xが、0.08〜0.03であることを特徴とする殺菌剤。 - 請求項1に記載の殺菌剤であって、
成分(b)に対する成分(a)の重量比xが、0.07〜0.04であることを特徴とする殺菌剤。 - 請求項1〜4のいずれか1項に記載の殺菌剤であって、さらに該殺菌剤が、水、エタノールおよび/またはH2O2を含むことを特徴とする殺菌剤。
- マイコバクテリアを制御するための方法で、請求項1〜5のいずれか1項に記載の殺菌剤を殺菌される表面に作用させることによる方法であって、前記殺菌される表面が、金属、ガラス、プラスチックまたはセラミックから製造されることを特徴とする方法。
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DE10224979A DE10224979B4 (de) | 2002-06-05 | 2002-06-05 | Verwendung von synergistischen Zubereitungen auf Basis von Gemischen von Glycerinether mit aromatischem Alkohol zur Bekämpfung von Mykobakterien |
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JP2010178007A Expired - Lifetime JP5587094B2 (ja) | 2002-06-05 | 2010-08-06 | マイコバクテリアを制御するための、芳香族アルコールとグリセロールエーテルの混合液に基づく相乗的製剤 |
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FR2755852B1 (fr) * | 1996-11-15 | 1998-12-24 | Oreal | Utilisation d'un alkylether de glycerol dans une composition cosmetique et/ou dermatologique comme actif pour le traitement de la seborrhee et de l'acne |
DE19749760A1 (de) | 1997-11-11 | 1999-05-12 | Henkel Kgaa | Mehrphasen-Stiftpräparat |
DE19801821B4 (de) * | 1998-01-15 | 2006-06-22 | Schülke & Mayr GmbH | Tuberkulozides Desinfektionsmittel |
DE10025124B4 (de) * | 2000-05-20 | 2015-07-16 | Beiersdorf Ag | Kombinationen von Glycerinmonoalkylethern und Aryl-substituierten Alkoholen |
DE10028638A1 (de) * | 2000-06-09 | 2001-12-20 | Schuelke & Mayr Gmbh | Lagerstabile Zusammensetzungen von Glycerinmonoalkylethern |
DE10224979B4 (de) | 2002-06-05 | 2004-07-15 | Schülke & Mayr GmbH | Verwendung von synergistischen Zubereitungen auf Basis von Gemischen von Glycerinether mit aromatischem Alkohol zur Bekämpfung von Mykobakterien |
-
2002
- 2002-06-05 DE DE10224979A patent/DE10224979B4/de not_active Expired - Lifetime
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2003
- 2003-05-07 EP EP18207021.9A patent/EP3479694A1/en active Pending
- 2003-05-07 EP EP12163167.5A patent/EP2505060B1/en not_active Revoked
- 2003-05-07 EP EP03291094.5A patent/EP1369037B2/en not_active Expired - Lifetime
- 2003-05-07 ES ES12163167.5T patent/ES2605444T3/es not_active Expired - Lifetime
- 2003-05-07 EP EP11183977A patent/EP2404501A3/en not_active Ceased
- 2003-05-07 ES ES03291094T patent/ES2402047T3/es not_active Expired - Lifetime
- 2003-05-27 US US10/445,715 patent/US20040059006A1/en not_active Abandoned
- 2003-05-29 JP JP2003151764A patent/JP5101786B2/ja not_active Expired - Lifetime
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2010
- 2010-07-01 US US12/828,713 patent/US8440725B2/en not_active Expired - Lifetime
- 2010-08-06 JP JP2010178007A patent/JP5587094B2/ja not_active Expired - Lifetime
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Also Published As
Publication number | Publication date |
---|---|
US8710103B2 (en) | 2014-04-29 |
DE10224979B4 (de) | 2004-07-15 |
DE10224979A1 (de) | 2003-12-24 |
EP2505060B1 (en) | 2016-09-14 |
EP2404501A3 (en) | 2013-04-03 |
EP1369037B1 (en) | 2012-12-26 |
US20040059006A1 (en) | 2004-03-25 |
US20130231397A1 (en) | 2013-09-05 |
US20100331426A1 (en) | 2010-12-30 |
ES2402047T3 (es) | 2013-04-26 |
EP2505060A3 (en) | 2013-04-03 |
JP2011006434A (ja) | 2011-01-13 |
EP2404501A2 (en) | 2012-01-11 |
US8440725B2 (en) | 2013-05-14 |
JP5101786B2 (ja) | 2012-12-19 |
EP1369037B2 (en) | 2024-07-17 |
JP2004099588A (ja) | 2004-04-02 |
EP2505060A2 (en) | 2012-10-03 |
EP3479694A1 (en) | 2019-05-08 |
ES2605444T3 (es) | 2017-03-14 |
EP1369037A1 (en) | 2003-12-10 |
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