JP4657715B2 - 抗菌性組成物 - Google Patents
抗菌性組成物 Download PDFInfo
- Publication number
- JP4657715B2 JP4657715B2 JP2004528017A JP2004528017A JP4657715B2 JP 4657715 B2 JP4657715 B2 JP 4657715B2 JP 2004528017 A JP2004528017 A JP 2004528017A JP 2004528017 A JP2004528017 A JP 2004528017A JP 4657715 B2 JP4657715 B2 JP 4657715B2
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- Prior art keywords
- product
- salt
- mixture
- cinnamaldehyde
- acid
- 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.)
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- 150000003839 salts Chemical class 0.000 claims description 52
- 229940117916 cinnamic aldehyde Drugs 0.000 claims description 51
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- UREZNYTWGJKWBI-UHFFFAOYSA-M benzethonium chloride Chemical compound [Cl-].C1=CC(C(C)(C)CC(C)(C)C)=CC=C1OCCOCC[N+](C)(C)CC1=CC=CC=C1 UREZNYTWGJKWBI-UHFFFAOYSA-M 0.000 description 1
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- 230000001680 brushing effect Effects 0.000 description 1
- 235000019282 butylated hydroxyanisole Nutrition 0.000 description 1
- 229940067596 butylparaben Drugs 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 229940081733 cetearyl alcohol Drugs 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 229960003260 chlorhexidine Drugs 0.000 description 1
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- DHNRXBZYEKSXIM-UHFFFAOYSA-N chloromethylisothiazolinone Chemical compound CN1SC(Cl)=CC1=O DHNRXBZYEKSXIM-UHFFFAOYSA-N 0.000 description 1
- 229960005443 chloroxylenol Drugs 0.000 description 1
- 235000017803 cinnamon Nutrition 0.000 description 1
- 229940017545 cinnamon bark Drugs 0.000 description 1
- 235000020230 cinnamon extract Nutrition 0.000 description 1
- QAIPRVGONGVQAS-UHFFFAOYSA-N cis-caffeic acid Natural products OC(=O)C=CC1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-UHFFFAOYSA-N 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000001332 colony forming effect Effects 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 235000019258 dehydroacetic acid Nutrition 0.000 description 1
- 229940061632 dehydroacetic acid Drugs 0.000 description 1
- PGRHXDWITVMQBC-UHFFFAOYSA-N dehydroacetic acid Natural products CC(=O)C1C(=O)OC(C)=CC1=O PGRHXDWITVMQBC-UHFFFAOYSA-N 0.000 description 1
- JEQRBTDTEKWZBW-UHFFFAOYSA-N dehydroacetic acid Chemical compound CC(=O)C1=C(O)OC(C)=CC1=O JEQRBTDTEKWZBW-UHFFFAOYSA-N 0.000 description 1
- 229940105990 diglycerin Drugs 0.000 description 1
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 229940088638 glycereth-7 Drugs 0.000 description 1
- UBHWBODXJBSFLH-UHFFFAOYSA-N hexadecan-1-ol;octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO.CCCCCCCCCCCCCCCCCCO UBHWBODXJBSFLH-UHFFFAOYSA-N 0.000 description 1
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 1
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
- 229940113094 isopropylparaben Drugs 0.000 description 1
- MGIYRDNGCNKGJU-UHFFFAOYSA-N isothiazolinone Chemical compound O=C1C=CSN1 MGIYRDNGCNKGJU-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000005555 metalworking Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- BEGLCMHJXHIJLR-UHFFFAOYSA-N methylisothiazolinone Chemical compound CN1SC=CC1=O BEGLCMHJXHIJLR-UHFFFAOYSA-N 0.000 description 1
- 229940078812 myristyl myristate Drugs 0.000 description 1
- 229940078555 myristyl propionate Drugs 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical class [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
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- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YRZGMTHQPGNLEK-UHFFFAOYSA-N tetradecyl propionate Chemical compound CCCCCCCCCCCCCCOC(=O)CC YRZGMTHQPGNLEK-UHFFFAOYSA-N 0.000 description 1
- DZKXJUASMGQEMA-UHFFFAOYSA-N tetradecyl tetradecanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCC DZKXJUASMGQEMA-UHFFFAOYSA-N 0.000 description 1
- ICUTUKXCWQYESQ-UHFFFAOYSA-N triclocarban Chemical compound C1=CC(Cl)=CC=C1NC(=O)NC1=CC=C(Cl)C(Cl)=C1 ICUTUKXCWQYESQ-UHFFFAOYSA-N 0.000 description 1
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- ICTZCAHDGHPRQR-UHFFFAOYSA-N usnic acid Natural products OC1=C(C)C(O)=C(C(C)=O)C2=C1C1(C)C(O)=C(C(=O)C)C(=O)C=C1O2 ICTZCAHDGHPRQR-UHFFFAOYSA-N 0.000 description 1
- 229940004858 usnic acid Drugs 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- 239000002888 zwitterionic surfactant Substances 0.000 description 1
Images
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Description
(a)レモングラス油;
(b)シンナムアルデヒド、シンナモン油、シンナモナムカッシア(cinnamomum cassia)、シンナモン抽出物、カッシア葉油、3,4-ジヒドロキシ桂皮酸もしくはその塩、またはこれらの混合物;
(c)ソルビン酸、またはその塩;
(d)エリソルビン酸、またはその塩;
(e)安息香酸、またはその塩;
(f)アラビノガラクタン、ガラクトアラビナン(galactoarabinan)、またはこれらの混合物;
(g)ヘキサヒドロ-イソ-α酸、テトラヒドロ-イソ-α酸、またはこれらの混合物;
(h)アキレア フラグランティシマ油(Achillea fragrantissima oil)、サントリーナ フラグランティシマ油(Santolina fragrantissima oil)、ホルススク油(Forssk oil)、ラベンダー コットン油(Lavender cotton oil);および
(i)グルコノ-δ-ラクトン
の少なくとも2つを含んでなる抗菌性組成物を提供する。好ましくは、本発明の混合物は、抗菌的(例えば、保存的、殺菌的、および/または殺真菌的)で相乗作用的な有効量の上述した成分を含む。
[32] 用語「微生物」は、細菌、真菌、酵母、藻、昆虫および害虫を含むがこれらに限定されない。
[38] あらゆる供給源由来のシンナムアルデヒドを、本発明中に使用することができる。例えば、シンナムアルデヒドは、シンナモンバーク抽出物(例えば、樹皮および葉由来のもの)、カッシア葉油、シンナモナムカッシア、シンナモン油、シンナマール(cinnamal)、桂皮アルコール、およびこれらの混合物から誘導されてもよい。
(i) シンナムアルデヒドと、ソルビン酸、エリソルビン酸、またはこれらの塩
[46] 好ましい混合物は、シンナムアルデヒドと、ソルビン酸またはその塩、例えばソルビン酸カリウムである。他の好ましい混合物は、シンナムアルデヒドと、エリソルビン酸またはその塩、例えばエリソルビン酸ナトリウムである。シンナムアルデヒドと(i)ソルビン酸もしくはその塩または(ii)エリソルビン酸もしくはその塩との重量比は、好ましくは約10:1〜約0.1:1、より好ましくは約5:1〜約0.2:1である。
[50] 他の好ましい混合物は、(a)エリソルビン酸もしくはその塩(例えばエリソルビン酸ナトリウム)と、(b)1以上の(i)クエン酸もしくはその塩、(ii)グルコノ-δ-ラクトン、(iii)安息香酸もしくはその塩(例えば、安息香酸ナトリウム)、(iv)ソルビン酸もしくはその塩、または(v)エチレンジアミン四酢酸(EDTA)もしくはその塩である。
[55] 本発明の抗菌性組成物は、抗菌的、殺真菌的、および殺菌的な薬剤(例えば、アレルゲン、樹木および植物真菌、植物および樹木細菌に対する薬剤)として有用であり、製紙業、織物業、農業、およびコーティング産業の保存剤として、パーソナルケア用、家庭用、産業用、および業務用の製品の保存剤として有用である。抗菌性組成物を、微生物が増殖し易い基体に組み込んでこれを保存してもよい。例えば、保存系は、パーソナルケア製品、例えばシャンプー、コンディショナー、クリーム、ローション(例えば、ボディーローション)、化粧品、もしくは石鹸;家庭用製品、例えば織物用柔軟仕上げ剤、洗濯用洗剤、もしくは硬質表面用クリーナー;または産業用製品、例えば塗料、コーティング、木材、織物、接着剤、シーラント、革、ロープ、紙、パルプ、厚紙、シートロック(sheet rock)、天井用タイル、プラスチック、燃料、石油、油、ゴム作動用流体、金属作動用流体、澱粉(例えばペットフード用澱粉)、もしくは鉱物スラリー、例えば粘土のスラリー、炭酸カルシウム、もしくは酸化チタン(TiO2)に組み込まれていてもよいし、あるいはそれ自体であってもよい。
[57] シンナムアルデヒドならびに(i)シンナムアルデヒドと(ii)アルカノールジアルキルヒダントイン、イソチアゾロン、およびベンズイソチアゾリノンの少なくとも1つとの混合物(以下、「保存系」という)は、抗菌的、殺真菌的、および殺菌的な薬剤(例えば、アレルゲン、樹木真菌、および樹木細菌に対する薬剤)として有用であり、製紙業、織物業、農業、およびコーティング産業の保存剤として、パーソナルケア用、家庭用、産業用、および業務用の製品の保存剤として有用である。保存系を、微生物が増殖し易い基体に組み込んでこれを保存してもよい。例えば、保存系は、パーソナルケア製品、例えばシャンプー、コンディショナー、クリーム、ローション(例えばボディーローション)、化粧品、もしくは石鹸;家庭用製品、例えば織物用柔軟仕上げ剤、洗濯用洗剤、もしくは硬質表面用クリーナー;または産業用製品、例えば塗料、コーティング、木材、織物、接着剤、シーラント、革、ロープ、紙、パルプ、厚紙、シートロック、天井用タイル、プラスチック、燃料、石油、油、ゴム作動用流体、金属作動用流体、澱粉(例えばペットフード用澱粉)、もしくは鉱物スラリー、例えば粘土のスラリー、炭酸カルシウム、もしくは酸化チタン(TiO2)に組み込まれていてもよいし、あるいはそれ自体であってもよい。
[71] 図1〜3の各陰イオン性シャンプーのサンプルについて次のように試験を行った。標準化された混合細菌溶液を、次の手順に従って調製した。黄色ブドウ球菌(ATCC♯6538)、緑濃菌(ATCC♯9027)、および大腸菌(ATCC♯8739)の3つの寒天スタッブ(agar stab)を約35℃で約24時間にわたり別々にインキュベートした。その後、各スタッブを3mLの無菌0.85%塩溶液で洗浄した。3つのスタッブの洗浄物を一緒にプールして生物体混合物を調製した。530nmでの生物体混合物の吸光度を、塩溶液を加えることによって約1.00に調整した。分光計を塩溶液ブランクで較正した。生物体混合物の5mLアリコートを一緒に混合して標準化された混合細菌溶液を調製した。その後、40gの各シャンプーのサンプルに、0.2 mLの標準化された混合細菌溶液を接種し混合した。無菌の20×150mmスクリューキャップの試験管にこの混合液を1 g加えた。
[76] 図4〜7の各陰イオン性シャンプーのサンプルについて次のように試験を行った。標準化された混合細菌溶液を、次の手順に従って調製した。カンジダ アルビカンスの2つの寒天スラント(agar slant)とアスペルギルス ニガーの4つの寒天スラントとを、約25℃で約48時間および7日間にわたりそれぞれ別々にインキュベートした。各スラントを3 mLの無菌0.85%塩溶液で洗浄し、組織粉砕機中に集めて細断した。十分な量の0.85%塩溶液を各スラントに加え、顕微鏡下でノイバウアー血球計算板を使ってカンジダ アルビカンスとアスペルギルス ニガーの各接種物(innoculum)の目視の数を得た。カンジダ アルビカンスとアスペルギルス ニガーの各標準化された接種物の等しい量を一緒に混合し、標準化された混合真菌溶液を調製した。
[81] 下記の表1に示された保存処方剤で、例1に記載された手順を繰り返した。シャンプーのpHを6.5に調整した。また、その結果を表1に示す。
[84] 下記の表3の各陰イオン性シャンプーのサンプルについて次のように試験を行った。標準化された混合細菌溶液を次の手順に従って調製した。黄色ブドウ球菌(S. aureus(ATCC♯6538)、緑濃菌(P. aeruginosa)(ATCC♯9027)、および大腸菌(E.coli)(ATCC♯8739)の3つの寒天スタッブ(agar stab)を約35℃で約24時間にわたり別々にインキュベートした。その後、各スタッブを3mLの無菌0.85%塩溶液で洗浄した。3つのスタッブの洗浄物を一緒にプールして生物体混合物を調製した。530nmでの生物体混合物の吸光度を、塩溶液を加えることによって約1.00に調整した。分光計を塩溶液ブランクで較正した。生物体混合物の5mLアリコートを一緒に混合して標準化された混合細菌溶液を生成した。その後、40gの各シャンプーのサンプルに、0.2 mLの標準化された混合細菌溶液を接種し混合した。無菌の20×150mmスクリューキャップの試験管にこの混合物を1 g加えた。
[90] 下記の表4の各陰イオン性シャンプーのサンプルについて以下のように試験を行った。標準化された混合細菌溶液を、以下の手順に従って調製した。カンジダ アルビカンスの2つの寒天スラントとアスペルギルス ニガーの4つの寒天スラントとを、約25℃で約48時間および7日間にわたりそれぞれ別々にインキュベートした。各スラントを3 mLの無菌0.85%塩溶液で洗浄し、組織粉砕機中に集めて細断した。十分な量の0.85%塩溶液を各スラントに加え、顕微鏡下でノイバウアー血球計算板を使ってカンジダ アルビカンスとアスペルギルス ニガーの各接種物(innoculum)の目視の数を得た。カンジダ アルビカンスとアスペルギルス ニガーの各標準化された接種物の等しい量を一緒に混合し、標準化された混合真菌溶液を調製した。
[94] 下記の表5の各クリームのサンプルについて例1に記載した手順に従って試験を行った。グリセリルモノステアレート(GMS)のクリームを、下記の表3に記載されたように以下のように調製した。ポリオキシエチレングリセリルモノステアレート、グリセリルモノステアレート、セテアリールアルコール、およびミリスチルプロピオン酸塩を、第1の容器内で混合し60℃まで加熱した。グリセリンと無菌の脱イオン水とを、第2の容器内で混合し60℃まで加熱した。第1の容器内の溶液を第2の容器内に注いだ。第2の容器を60℃で10分間維持した。第2の容器内の溶液を冷却しておいた。溶液のpHを水酸化ナトリウムでpH 7に調整し、GMSクリームを得た。
[97]下記の表8に示したシャンプーのサンプルについて例4の手順を繰り返した。結果を表8に示した。
[102] 保存剤混合物の最小阻害濃度(MIC)について試験を行った。MICとは、生物体の増殖を阻害するであろう成分の最低の濃度をいう。この研究は、ハミルトン ミクロ ラボ AT プラス自動希釈装置液体処理システムを使用して行われた。自動希釈装置のためのプログラムは、ロンザ社の標準適用方法SAPM♯412-01-1に基づいた。ハミルトン自動希釈装置を使用して保存剤組み合わせの開始濃度を、96ウェルマイクロタータプレート中においてブイヨンを使用して50%まで希釈し、試験サンプル中に微生物を接種した。
[107] 下記のシンナムアルデヒド/ソルビン酸カリウムの混合物の色彩安定性についてガードナー色彩試験で試験を行った。塩酸を添加して処方剤のpHを指定されたpHに調整した。結果を以下に示す。
Claims (10)
- 抗菌性組成物であって:
(a)シンナムアルデヒド;および
(b)ソルビン酸、またはその塩;
を含み、さらに
(c)レモングラス油;
(d)エリソルビン酸、またはその塩;
(e)安息香酸、またはその塩;
(f)アラビノガラクタン、ガラクトアラビナン、またはこれらの混合物;
(g)ホップス抽出物から得られるヘキサヒドロ-イソ-α酸、テトラヒドロ-イソ-α酸、またはこれらの混合物;
(h)アキレア フラグランティシマ(サントリーナ フラグランティシマ ホルススク、ラベンダー コットン)油;および
(i)δ-グルコノラクトン
のうち1以上を任意に含む抗菌的有効量の混合物を含んでなる抗菌性組成物。 - 前記成分(b)の塩が、ソルビン酸カリウムである請求項1の抗菌性組成物。
- 溶媒をさらに含んでなる請求項1の抗菌性組成物。
- 前記溶媒が、水、グリコール、アルコール、およびこれらの混合物から選択される請求項3の抗菌性組成物。
- 前記溶媒が、水とグリコールとの混合物である請求項4の抗菌性組成物。
- 前記グリコールがグリセリンである請求項5の抗菌性組成物。
- 前記溶媒が、水とアルコールとの混合物である請求項4の抗菌性組成物。
- 前記アルコールがエタノールである請求項7の抗菌性組成物。
- 前記組成物の混合物が、全組成物の100重量%に基づいて0.001〜2重量%の濃度で存在する請求項1の抗菌性組成物。
- 製品の内部または表面の微生物を殺傷および/またはその増殖を阻害する方法であって、請求項1の有効量の抗菌性組成物を前記製品に適用することを含んでなる方法。
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