JP4669683B2 - 抗菌剤組成物 - Google Patents
抗菌剤組成物 Download PDFInfo
- Publication number
- JP4669683B2 JP4669683B2 JP2004262903A JP2004262903A JP4669683B2 JP 4669683 B2 JP4669683 B2 JP 4669683B2 JP 2004262903 A JP2004262903 A JP 2004262903A JP 2004262903 A JP2004262903 A JP 2004262903A JP 4669683 B2 JP4669683 B2 JP 4669683B2
- Authority
- JP
- Japan
- Prior art keywords
- antibacterial
- agent composition
- antibacterial agent
- bacteria
- sodium
- 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.)
- Expired - Lifetime
Links
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Classifications
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- A—HUMAN NECESSITIES
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- A—HUMAN NECESSITIES
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
- A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
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- A—HUMAN NECESSITIES
- 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
- A01N49/00—Biocides, pest repellants or attractants, or plant growth regulators, containing compounds containing the group, wherein m+n>=1, both X together may also mean —Y— or a direct carbon-to-carbon bond, and the carbon atoms marked with an asterisk are not part of any ring system other than that which may be formed by the atoms X, the carbon atoms in square brackets being part of any acyclic or cyclic structure, or the group, wherein A means a carbon atom or Y, n>=0, and not more than one of these carbon atoms being a member of the same ring system, e.g. juvenile insect hormones or mimics thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
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Description
例えば、飲食品には、日持ち向上、食中毒防止を目的とし、防腐剤が添加される。また、口腔用品においては、虫歯、歯周病の原因となる虫歯原因菌、歯周病菌の増殖を防止、抑制する目的で、抗菌剤が添加されてきた。また、香粧品にはワキガ、フケ、ニキビの原因となるワキガ菌、フケ菌、ニキビ菌の増殖を抑制する等の目的で抗菌剤が製品に添加されてきた。
例えば、従来、香粧品などの防腐剤として多く使用されているパラベンは、抗菌スペクトルが狭い上に活性が弱く、必ずしも満足出来る抗菌剤ではなかった。また、強い抗菌活性、広い抗菌スペクトルを有する抗菌素材として知られるトリクロサン(Triclosan)は、分子内に塩素原子を含有しており、環境、人体への影響が危惧されることから、製品への使用が制限されている。
本発明における「抗菌剤組成物」とは、(a)9-(3',7'-ジメチル-2',6'-オクタジエニル)-4-ヒドロキシ-7H-フロ[3,2-γ][1]ベンゾピラン-7-オン(下記式(1))と、(b)8-(3',7'-ジメチル-2',6'-オクタジエニル)-5-ヒドロキシ-7-メトキシ-2H-1-ベンゾピラン-2-オン(下記式(2))との混合物を有効成分とする剤であり、防腐剤、殺菌剤の作用をあわせもつ性質を有した、優れた剤のことをいう。
虫歯原因菌;アクチノマイセス・ネスランディ(Actinomyces naeslundii)、アクチノマイセス・ビスコーサス(Actinomyces viscosus)、ストレプトコッカス・ミュータンス(Streptococcus mutans)
歯周病菌;フソバクテリウム・ナクレタム(Fusobacterium nucleatum)、プレボテラ・インテルメディア(Prevotella intermedia)、ポルフィロモナス・ジンジバリス(Porphyromonas gingivalis)
ニキビ菌;プロピオニバクテリウム・アクネス(Propionibacterium acnes)
膿瘍菌;バクテロイデス・フラジリス(Bacteroides fragilis)
ワキガ菌;コリネバクテリウム・ゼロシス(Corynebacterium xerosis)
フケ菌;マラセチア・フルフル(Malassezia furfur)
皮膚常在菌;スタフィロコッカス・エピデルミディス(Staphyrococcus epidermidis)、コリネバクテリウム・ミヌティシマム(Corynebacterium minutissimum)
腐敗菌;バシラス・サブティラス(Bacillus subtilis)
食中毒菌;腸炎ビブリオ菌(Vibrio parahaemoliticus)、カンピロバクター・ジェジェニ(Campylobactor jejuni)
胃潰瘍原因菌;ヘリコバクター・ピロリ(Helicobacter pylori)
黄色葡萄球菌:スタフィロコッカス・アウレウス(Staphyrococcus aureus)
耐熱性好酸性菌:アリシクロバシラス・アシドカルダリウス(Alicyclobacillus acidocaldarius(NCIMB))、アリシクロバシラス・アシドテレストリス(Alicyclobacillus acidoterrestris(NCIMB))など。
香料の配合量は、抗菌剤組成物の適用対象、使用方法などにより変動するが、通常抗菌剤組成物に対して0.001重量%〜50重量%とすることが好ましい。
本発明の用いられるフレグランスとしては、炭化水素類、アルコール類、フェノール類、アルデヒド類及び/又はアセタール類、ケトン類及び/又はケタール類、エーテル類、合成ムスク類、酸類、ラクトン類、エステル類、含ハロゲン化合物、天然香料などが挙げられる。
これら、フレーバーおよびフレグランスは、1種および2種以上を混合して使用しても良い。
これらは市販のものを使用することもできる。また単品は、合成品を使用してもよいし、植物などの天然起源から導入してもよい。精油、レジノイド、バルサム、アブソリュート、コンクリート、チンキなどは、公知の方法で調製することもできる。
上記基礎化粧品としては、スキンクリーム、クレンジングクリーム、化粧水、アフターシェーブローション、ファンデーション、口紅、タルカムパウダーなどを挙げることが出来る。
上記洗剤としては、衣類用粉末洗剤、衣類用液体洗剤、柔軟仕上げ剤、台所用洗剤、トイレ用洗剤、浴室用洗剤、ガラスクリーナー、カビ取剤などが挙げられる。
上記浴溶剤としては粉末入浴剤、固形入浴剤、固形発泡入浴剤、バスオイル、バブルバスなどを上げることができる。
上記芳香消臭剤としては、ゲル状芳香消臭剤、ミストタイプ芳香消臭剤、含浸型エアゾール芳香消臭剤等が挙げられる。
上記口腔用品としては洗口剤、歯磨き粉、オーラルケア用ガム、オーラルケア用キャンデー等が挙げられる。
食中毒菌などは、食品の腐敗劣化を導き、食品の商業的価値を大きく損ねる。更に、菌の増殖に伴い、製品内において毒素を生成し、それを食したものに対して重大な悪影響をもたらす。従って本発明における抗菌剤組成物を食品に含有せしめることにより、食品に対する日持ち向上効果や、食中毒防止が達成される。
特許第2864436号記載の方法で調製した9-(3',7'-ジメチル-2',6'-オクタジエニル)-4-ヒドロキシ-7H-フロ[3,2-γ][1]ベンゾピラン-7-オン(a)と、特許第2864436号記載の方法で調製した8-(3',7'-ジメチル-2',6'-オクタジエニル)-5-ヒドロキシ-7-メトキシ-2H-1-ベンゾピラン-2-オン(b)を以下の重量比で混合して各抗菌剤組成物を調製し、各抗菌剤組成物を0.2%エタノール溶液とした後に本実施例に用いた。
抗菌剤組成物(A) (a):(b)=1:8
抗菌剤組成物(B) (a):(b)=1:1
抗菌剤組成物(C) (a):(b)=8:1
抗菌剤組成物(D) (a):(b)=1:30
抗菌剤組成物(E) (a):(b)=30:1
抗菌剤組成物(F) (a):(b)=0:1
抗菌剤組成物(G) (a):(b)=1:0
特許第2864436号記載の方法で調製した9-(3',7'-ジメチル-2',6'-オクタジエニル)-4-ヒドロキシ-7H-フロ[3,2-γ][1]ベンゾピラン-7-オン(a)と、特許第2864436号記載の方法で調製した8-(3',7'-ジメチル-2',6'-オクタジエニル)-5-ヒドロキシ-7-メトキシ-2H-1-ベンゾピラン-2-オン(b)を以下の重量比で混合して抗菌剤組成物を調製し、各抗菌剤組成物を0.2%中鎖脂肪酸トリグリセリド(MCT)溶液とした。
抗菌剤組成物(H) (a):(b)=1:8
抗菌剤組成物(I) (a):(b)=8:1
抗菌剤組成物(J) (a):(b)=1:1
寒天培地希釈法(ADT;Agar Dilution Test)により最小生育阻止濃度(MIC)の測定を実施した。
実施例1で得られた各抗菌剤組成物をエタノール又は水(各抗菌剤組成物の溶解性による)に溶解して系列2倍希釈段階を作り、その100μlを10mlの滅菌寒天培地(皮膚関連、一般細菌はMueller Hinton Medium(Difco)、酵母、糸状菌はSabroud Medium(Difco)、嫌気性菌はTrypticase Soy agar(BBL))に加え、良く撹拌した後9cmφのシャーレに移し室温で固化させた。このシャーレに佐久間製作所のミクロプランターMIT-P27本用を用い、皮膚関連菌、一般細菌の試験菌については1×105cfu(colony forming unit:生菌数のこと)ずつスポットし、37℃で18時間培養した。嫌気性菌は37℃、72時間嫌気条件下(BBLのガスパック嫌気システムを使用)で培養する。培養終了後アルコールのみを加えたシャーレ(ブランク)とそれぞれの菌の生育を比較し、菌の生育の見られないサンプルの濃度を最小阻止濃度(MIC)とした。
比較物質として、ブチルパラベン(BPHB)およびトリクロサンも測定した。結果は以下のとおりである。
また(a)成分、(b)成分それぞれ単独よりなる抗菌剤組成物(F)、抗菌剤組成物(G)もそれなりの抗菌効果を示した。しかしながら、(a)成分、(b)成分を混合することにより作製した抗菌剤組成物(A)と比較すると、抗菌剤組成物(F)、抗菌剤組成物(G)は明らかに抗菌スペクトルが狭く、抗菌効果を示したとしても、抗菌剤組成物(A)よりも強い抗菌効果を示すことはなかった。このことから、抗菌剤組成物(F)、抗菌剤組成物(G)が十分な抗菌効果を有しているとはいい難い。抗菌剤組成物(A)の結果から確認できるように、(a)成分、(b)成分を混合して調製することにより、初めて実用可能な効果を有する抗菌剤組成物が得られることがわかる。
アリシクロバシラス・アシドカルダリウス(NCIMB)、アリシクロバシラス・アシドテレストリス(NCIMB)の芽胞を緩衝生理食塩水で100万〜200万個/100μlまで希釈し、80℃、10分間加熱した後、AAM(アリシクロバシラス アシドテレストリス用培地(Alicyclobacillus Acidoterrestris medium))液体培地5mlにつき100μlずつ添加した。以上のように準備した試験用培地に、以下の手順で実施例1で得られた抗菌剤組成物(A)を添加した。グレープフルーツフレーバー中に抗菌剤組成物(A)を20mg/ml、10mg/ml、5mg/ml、2.5mg/mlとなるように加えたフレーバーを、各培地に0.1%添加した(抗菌剤組成物(A)最終濃度20ppm、10ppm、5ppm、2.5ppm)。対照区として、グレープフルーツフレーバーを0.1%添加した培地と何も加えない培地を用意し、菌が問題なく生育することを確認した。以上のように調製した培地を50℃で10日間培養し、菌の増殖に伴う培地の濁りから菌の生育を判定し、生育抑制効果を確認した。各試験菌、各サンプルにつき5本の培地で実験を行い、全ての培地で菌の生育が阻止された濃度をもって、最小生育阻止濃度(MIC)とした。
比較物質として、ショ糖脂肪酸エステルも測定した。結果は以下のとおりである。
以下、実施例1で調製した抗菌剤組成物(A)を用いて、下記組成を有する香粧品、飲食品、口腔用品を調製した。
リン酸2カルシウム 10.0
ラウリル硫酸ナトリウム 2.0
カルボキシメチルセルロースナトリウム 0.5
サッカリンナトリウム 0.02
薄荷香味剤 1.0
抗菌剤組成物(A) 0.05%
グリセリン 適量
100.0
エチルアルコール 10.0
ポリオキシエチレン水素化ひまし油 2.0
薄荷香味剤 0.5
サッカリンナトリウム 0.02
グリセリン 10.0
色素 適量
抗菌剤組成物(C) 0.25
精製水 適量
100.0
砂糖粉末 50.0
水飴 33.0
クエン酸 1.0
抗菌剤組成物(C) 0.25
精製水 適量
100.0
ガム素地 21.0
砂糖粉末 63.9
とうもろこしでんぷん 12.5
レモン型香味剤 1.0
酸性化剤 0.6
抗菌剤組成物(A) 1.0
100.0
でんぷん 98.45
薄荷型粉末香味剤 0.8
スクロース脂肪酸エステル 0.5
抗菌剤組成物(B) 0.25
100.0
エタノール 20.0
抗菌剤組成物(C) 5.0
精製水 適量
100.0
ラウリン酸、ステアリン酸硫酸ナトリウム 15.0
炭酸ナトリウム 15.0
メタ珪酸ナトリウム 13.0
クエン酸ナトリウム 15.0
カルボキシメチルセルロース 2.0
硫酸ナトリウム 38.0
麝香樹木系芳香剤 1.0
抗菌剤組成物(A) 1.0
100.0
PEG-7 グリセリルココエート(GLYCERYL COCOATE) 2.0
水素化油脂(HYDROGENATED OIL) 5.0
ミリスチン酸ミリスチル(MYRISTYL MYRISTATE) 15.0
シクロメチコーン 33.5
ステアリルアルコール(STEARYL ALCOHOL) 20.0
ステアリルイソノネノエート(STEARYL ISONONENOATE) 3.0
クロルヒドロキシアルミニウム(AL- CHROLOHYDRATE) 20.0
制汗剤用香料 0.5
抗菌剤組成物(C) 1.0
100.0
セチルアルコール 5.0
ステアリン酸 3.0
ワセリン 5.0
スクワラン 10.0
グリセロールトリ2−エチルヘキサン酸エステル 7.0
ジプロピレングリコール 5.0
グリセリン 5.0
プロピレングリコールモノステアリン酸エステル 3.0
POE(20)セチルアルコールエーテル 3.0
トリエタノールアミン 1.0
パラベン 0.3
クリーム用香料 1.0
抗菌剤組成物(C) 1.0
精製水 適量
100.0
ラウレス硫酸ナトリウム(SODIUM LAURETH SULFATE) 40.0
ココアンホ酢酸ナトリウム(SODIUMU COCOAMPHOACETATE) 10.0
コカミドDEA(COCAMIDE DEA) 2.0
ブチレングリコール(BUTYLENE GLYCOL) 2.0
クエン酸(CITRIC ACID) 0.35
塩化ナトリウム(SODIUM CHLORIDE) 0.1
パラベン(PARABEN) 0.3
テトラナトリウムEDTA(TETRASODIUM EDTA) 0.1
シャンプー用香料 0.5
抗菌剤組成物(A) 1.0
精製水 適量
100.0
果糖ブドウ糖液糖 107.0
クエン酸 1.0
クエン酸ナトリウム 0.3
オレンジ濃縮果汁 51.8
水溶性オレンジフレーバー 1.0
抗菌剤組成物(B) 0.1
水 適量
1000.0
砂糖 31.0
ブドウ糖 15.7
クエン酸 1.0
乳酸カルシウム 0.679
クエン酸ナトリウム 0.3
塩化ナトリウム 0.28
塩化カリウム 0.22
ビタミンC 0.864
L-グルタミン酸ナトリウム 0.03
ナイアシン 0.013
パントテン酸カルシウム 0.007
ビタミンB6 0.0022
ビタミンB12 0.000006
レモンフレーバー 1.0
抗菌剤組成物(B) 0.1
精製水 適量
1000.0
レギュラーコーヒー 50.0
グラニュー糖 50.0
牛乳 150.0
乳化剤(脂肪酸エステル) 0.5
コーヒーフレーバー 1.0
ミルクフレーバー 0.8
抗菌剤組成物(A) 0.1
精製水 適量
1000.0
果糖ブドウ糖液糖 127.0
クエン酸 1.24
精製水 200.0
レモンフレーバー 0.12
抗菌剤組成物(B) 0.05
炭酸水 適量
1000.0
アップル果汁 6.0
水飴 3.5
グラニュー糖 13.0
りんご酸 0.21
ゲル化剤 0.9
クエン酸ナトリウム 0.05
カラメル色素 0.08
アップルフレーバー 0.2
抗菌剤組成物(C) 0.01
精製水 適量
100.0
紅茶葉抽出液(brix 1.0) 200.0g
グラニュー糖 60.0
レモン濃縮果汁 1.56
ビタミンC 0.1
抗菌剤組成物(A) 0.05
精製水 適量
1000.0
Claims (5)
- 9-(3',7'-ジメチル-2',6'-オクタジエニル)-4-ヒドロキシ-7H-フロ[3,2-γ][1]ベンゾピラン-7-オンと、8-(3',7'-ジメチル-2',6'-オクタジエニル)-5-ヒドロキシ-7-メトキシ-2H-1-ベンゾピラン-2-オンとを含む、抗菌剤組成物。
- 9-(3',7'-ジメチル-2',6'-オクタジエニル)-4-ヒドロキシ-7H-フロ[3,2-γ][1]ベンゾピラン-7-オンと、8-(3',7'-ジメチル-2',6'-オクタジエニル)-5-ヒドロキシ-7-メトキシ-2H-1-ベンゾピラン-2-オンとの重量比が、1:30〜30:1である、請求項1記載の抗菌剤組成物。
- 請求項1又は2に記載の抗菌剤組成物を含むことを特徴とする口腔用品。
- 請求項1又は2に記載の抗菌剤組成物を含むことを特徴とする香粧品。
- 請求項1又は2に記載の抗菌剤組成物を含むことを特徴とする医薬品。
Priority Applications (10)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2004262903A JP4669683B2 (ja) | 2004-09-09 | 2004-09-09 | 抗菌剤組成物 |
ES05777114T ES2314696T3 (es) | 2004-09-09 | 2005-08-30 | Composicion antibacterina. |
AT05777114T ATE410925T1 (de) | 2004-09-09 | 2005-08-30 | Antibakterielle zusammensetzung |
DE602005010453T DE602005010453D1 (de) | 2004-09-09 | 2005-08-30 | Antibakterielle zusammensetzung |
US11/661,755 US20080096958A1 (en) | 2004-09-09 | 2005-08-30 | Antibacterial Composition |
CNB2005800301830A CN100566571C (zh) | 2004-09-09 | 2005-08-30 | 抗菌组合物 |
PCT/JP2005/016181 WO2006028025A1 (en) | 2004-09-09 | 2005-08-30 | Antibacterial composition |
KR1020077005553A KR101222778B1 (ko) | 2004-09-09 | 2005-08-30 | 항균성 조성물 |
EP05777114A EP1788878B1 (en) | 2004-09-09 | 2005-08-30 | Antibacterial composition |
US12/564,602 US20100016419A1 (en) | 2004-09-09 | 2009-09-22 | Antibacterial composition |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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JP2004262903A JP4669683B2 (ja) | 2004-09-09 | 2004-09-09 | 抗菌剤組成物 |
Publications (2)
Publication Number | Publication Date |
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JP2006076923A JP2006076923A (ja) | 2006-03-23 |
JP4669683B2 true JP4669683B2 (ja) | 2011-04-13 |
Family
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Application Number | Title | Priority Date | Filing Date |
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JP2004262903A Expired - Lifetime JP4669683B2 (ja) | 2004-09-09 | 2004-09-09 | 抗菌剤組成物 |
Country Status (9)
Country | Link |
---|---|
US (2) | US20080096958A1 (ja) |
EP (1) | EP1788878B1 (ja) |
JP (1) | JP4669683B2 (ja) |
KR (1) | KR101222778B1 (ja) |
CN (1) | CN100566571C (ja) |
AT (1) | ATE410925T1 (ja) |
DE (1) | DE602005010453D1 (ja) |
ES (1) | ES2314696T3 (ja) |
WO (1) | WO2006028025A1 (ja) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
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JP5483820B2 (ja) * | 2007-11-29 | 2014-05-07 | 株式会社マンダム | 抗菌性組成物及びデオドラント剤 |
JP5275637B2 (ja) * | 2008-01-29 | 2013-08-28 | 株式会社マンダム | 皮膚外用剤 |
CN101856890B (zh) * | 2009-04-09 | 2014-07-02 | 丰田纺织株式会社 | 表皮材料 |
US10252409B2 (en) | 2010-12-27 | 2019-04-09 | Bissell Homecare, Inc. | Magnetically cleaning fabric surfaces |
BR112015029686A2 (pt) * | 2013-05-28 | 2017-07-25 | Procter & Gamble | composições para o tratamento de superfícies compreendendo corantes fotocrômicos |
DE102014107412A1 (de) * | 2014-05-26 | 2015-12-17 | Schülke & Mayr GmbH | Gefärbte desinfizierende Zubereitung auf Basis von Bispyridiniumalkan |
JP6580850B2 (ja) * | 2015-03-31 | 2019-09-25 | 大和ハウス工業株式会社 | 空気浄化用土壌およびこの空気浄化用土壌を用いた屋内用緑化兼空気浄化装置 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH07138250A (ja) * | 1991-11-27 | 1995-05-30 | Takasago Internatl Corp | クマリン誘導体およびそれを含有する抗酸化剤 |
Family Cites Families (1)
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KR20000016351A (ko) * | 1997-04-04 | 2000-03-25 | 기울리아니 데이비드 | 구강 위생물용 항균제 |
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2004
- 2004-09-09 JP JP2004262903A patent/JP4669683B2/ja not_active Expired - Lifetime
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2005
- 2005-08-30 KR KR1020077005553A patent/KR101222778B1/ko not_active IP Right Cessation
- 2005-08-30 ES ES05777114T patent/ES2314696T3/es active Active
- 2005-08-30 CN CNB2005800301830A patent/CN100566571C/zh not_active Expired - Fee Related
- 2005-08-30 AT AT05777114T patent/ATE410925T1/de not_active IP Right Cessation
- 2005-08-30 EP EP05777114A patent/EP1788878B1/en not_active Not-in-force
- 2005-08-30 WO PCT/JP2005/016181 patent/WO2006028025A1/en active Application Filing
- 2005-08-30 DE DE602005010453T patent/DE602005010453D1/de active Active
- 2005-08-30 US US11/661,755 patent/US20080096958A1/en not_active Abandoned
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2009
- 2009-09-22 US US12/564,602 patent/US20100016419A1/en not_active Abandoned
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
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JPH07138250A (ja) * | 1991-11-27 | 1995-05-30 | Takasago Internatl Corp | クマリン誘導体およびそれを含有する抗酸化剤 |
Also Published As
Publication number | Publication date |
---|---|
US20100016419A1 (en) | 2010-01-21 |
US20080096958A1 (en) | 2008-04-24 |
EP1788878A1 (en) | 2007-05-30 |
JP2006076923A (ja) | 2006-03-23 |
ATE410925T1 (de) | 2008-10-15 |
CN100566571C (zh) | 2009-12-09 |
CN101022732A (zh) | 2007-08-22 |
KR101222778B1 (ko) | 2013-01-15 |
KR20070050470A (ko) | 2007-05-15 |
WO2006028025A1 (en) | 2006-03-16 |
DE602005010453D1 (de) | 2008-11-27 |
EP1788878B1 (en) | 2008-10-15 |
ES2314696T3 (es) | 2009-03-16 |
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