JP2015524485A - 銀含有組成物 - Google Patents
銀含有組成物 Download PDFInfo
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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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/26—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests in coated particulate form
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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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
- A01N25/10—Macromolecular compounds
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/12—Powdering or granulating
- C08J3/126—Polymer particles coated by polymer, e.g. core shell structures
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- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/20—Compounding polymers with additives, e.g. colouring
- C08J3/22—Compounding polymers with additives, e.g. colouring using masterbatch techniques
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K9/00—Use of pretreated ingredients
- C08K9/12—Adsorbed ingredients, e.g. ingredients on carriers
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L39/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions of derivatives of such polymers
- C08L39/04—Homopolymers or copolymers of monomers containing heterocyclic rings having nitrogen as ring member
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D139/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Coating compositions based on derivatives of such polymers
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D201/00—Coating compositions based on unspecified macromolecular compounds
- C09D201/02—Coating compositions based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
- C09D201/025—Coating compositions based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups containing nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F226/06—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2323/00—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers
- C08J2323/02—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers not modified by chemical after treatment
- C08J2323/04—Homopolymers or copolymers of ethene
- C08J2323/06—Polyethene
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08J2400/00—Characterised by the use of unspecified polymers
- C08J2400/10—Polymers characterised by the presence of specified groups, e.g. terminal or pendant functional groups
- C08J2400/106—Polymers characterised by the presence of specified groups, e.g. terminal or pendant functional groups containing nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08J2433/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
- C08J2433/04—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters
- C08J2433/14—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
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- Pest Control & Pesticides (AREA)
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Abstract
Description
本発明の一態様は、(a)銀イオン、(b)ペンダント型不飽和または芳香族ヘテロ環を有するポリマー、および(c)2mm以下の中位径を有する固体粒子を含む銀含有組成物であり、一部または全部の前記粒子が前記銀イオンおよび前記ポリマー(b)を含むコーティングを有する。
本明細書で使用される下記の用語は、文脈上明白に他の意味に解すべき場合を除き、指定された定義を有する。
米国特許第7,846,856号に記載の方法を使って、ポリマー溶液PS1を作製した。溶媒は、溶媒の重量をベースにして、重量で、70%エタノールおよび30%水とした。ポリマー組成は、ポリマー固体の重量をベースにして、重量で、45%ビニルイミダゾール、40%n−ブチルアクリラート、および15%アクリル酸とした。ポリマー固体は、溶液の重量をベースにして、重量で22.5%であった。銀イオンの量は、溶液の重量をベースにして、重量で2.9%であった。また、溶液は、アンモニウム、硝酸塩、および水酸化物イオンを含んでいた。溶液の色は、淡黄色であった。
RTで1000rpmでの攪拌下(IKAスターラー)、72gのPEP1またはSGP1を100gのPS1中に少しずつ添加した。30分の混合後、得られた黄色粘性液体を取り出し、100℃の真空オーブン(DZF−6030A、Shanghai Yihen)中で72時間乾燥した。次に、乾燥混合物を乳鉢/乳棒を使って微粉末に粉砕した。PEP1で作製した乾燥混合物は、本明細書では、Conc−PEP1と呼び、SGP1で作製した乾燥混合物は、本明細書では、Conc−SGP1と呼ぶ。
各試験試料に対し、2個の20mlのフラスコを用意し、それぞれに100mgの試料を入れた。両方のフラスコをオイル浴で加熱した。片方は窒素で覆い、他方は空気に暴露した。RTから約250℃まで加熱の間、退色をモニターした。UC1、UC2、Conc−PEP1、およびConc−SBP1の試料をこのようにして試験した。特定量の3種の比較用無機市販抗菌粉末(Comp1、Comp2、およびComp3)に対しても、Conc−PEP1およびConc−SGP1と同じ適用量の銀イオンを使って、空気下で類似の実験の実験を行った。
調合は、HAAKE PolyLab(商標)Mixer(Thermo)中で行った。最初に、49.5gのLDPEペレットを1分当たり60回転(rpm)下で5分間溶融し、次に、続けて、濃縮物または超濃縮物または比較用市販抗菌粉末を添加後、さらに5分間調合した。調合試料中の理論的銀イオン含量は、調合試料の重量をベースにして、重量で、50ppmであった。調合温度は、120℃とした。その後、調合試料を同じ温度で3分間ホットプレスにより圧縮成形して、3mmの厚さの最終シートを得た。3種の比較用試料(Comp1、Comp2、およびComp3)およびAgNO3とLDPEの調合も120℃で合計10分間行った。
プラスチック試料から40×40mmの矩形小片を切り出した後、老化試験オーブン(GDWシリーズ、Wuxi Suwei)中に入れ、60℃で8週間保持した。所定の時間で、試料を取り出し、RTに冷却した。全体の色の変化をエプソンスキャナーでスキャンした。a*、b*およびL*値を比色計(HunterLab ColorQuest(商標)XE比色計)により測定し、データを各試験片の少なくとも3点の平均とした。計算黄色度指数を使って、試料の抗老化能力を評価した。比較として、ベンチマーク試料も同じ方法で測定した。
次に、ATCC6538P法を使って、老化試験前後のプラスチック試料の抗菌特性を試験した。簡単に説明すると、プラスチックシートを40×40mmの正方形の小片に切断した後、種菌(黄色ブドウ球菌)を30×30mmの正方形の範囲上に添加した。24時間後、培養片のコロニー形成単位(cfu)を調べた。銀を含まないブランクのプラスチック片も同様に試験した。抗菌効力(log Kill)を、log10((24時間後のブランク試験片上のcfu)/(24時間後の処理試験片のcfu))と定義した。全データに対し、2個の並行処理試験片の平均を取った。比較のためにベンチマーク試料も同様に試験した。
Comp1、Comp2、およびComp3は、試験を通して白色のままであった。他の試料は、次の色(退色順に)を示した:LY(淡黄色、最小の退色);Y(黄色);Br(褐色);dBr(濃褐色);vdBr(極濃褐色);Blk(黒色)。
マトリックスプラスチックはLDPEとした。銀化合物の量は、各試料中の銀イオンの理論的濃度が、試料重量をベースにして、重量で50ppmとなるように選択した。貯蔵温度は60℃とした。3以上のLog Kill値は、微生物の死滅を効果的に遂行することを示す。
マトリックスプラスチックはLDPEとした。銀化合物の量は、各試料中の銀イオンの理論的濃度が、試料重量をベースにして、重量で50ppmとなるように選択した。3以上のLog Kill値は、微生物の死滅を効果的に遂行することを示す。貯蔵温度は60℃とした。
マトリックスプラスチック中のConc−PEP1およびConc−SGP1の分布を、米国特許第7,846,856号で調製され、報告された試料中の抗菌化合物の分布と比較した。上述のように、120℃の調合温度を使って、Conc−PEP1およびConc−SGP1がLDPE中に調合された場合、試料は、同様に調合されたLDPE単独のシートの外観と類似の白色で半透明であった。この試料は、銀濃縮物が試料全体にわたり均等に分布していることを示す。米国特許第7,846,856号で報告の試料は、銀/ポリマー錯体を乾燥し、本発明の定義の外側にある超濃縮物を得ることにより作製された。次に、米国特許第7,846,856号に記載のように、その超濃縮物を粉末状ポリプロピレン樹脂と混合し、その後、押出成形された。得られたプラスチック物品は、不透明で、抗菌化合物が均等に分布していないことを示した。
Conc−PEP1およびConc−SGP1の試料を薄い炭素層でコートし、走査電子顕微鏡(Brucker Company)で観察した。Conc−PEP1粒子は、約500マイクロメートルの中位径を有することが観察された。Conc−PEP1上のコーティングは、固体LDPE粒子の表面上の離散粒子として存在するのが認められた。コーティング粒子は、1マイクロメートル未満の中位径を有することが認められた。代表的コーティング粒子をX線分光法により分析し、コーティング粒子中の銀の存在を確認した。Conc−SG1粒子は、約40マイクロメータの中位径であることが認められた。Conc−SGP1上のコーティングは、固体シリカゲル粒子表面上の離散粒子として存在することが認められた。コーティング粒子は、1マイクロメートル未満の中位径を有することが認められた。代表的コーティング粒子をX線分光法により分析し、コーティング粒子中の銀の存在を確認した。
Claims (3)
- 銀含有組成物であって、
(a)銀イオン、
(b)ペンダント型不飽和または芳香族ヘテロ環を有するポリマー、および
(c)2mm以下の中位径を有する固体粒子、
を含み、一部または全部の前記粒子が前記銀イオンおよび前記ポリマー(b)を含むコーティングを有する組成物。 - 前記コーティングが銀/ポリマー(b)錯体を含む請求項1に記載の組成物。
- ペンダント型不飽和または芳香族ヘテロ環がイミダゾールを含む請求項1に記載の組成物。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201210224352.6A CN103509364B (zh) | 2012-06-29 | 2012-06-29 | 含银组合物 |
CN201210224352.6 | 2012-06-29 | ||
PCT/CN2013/077949 WO2014000638A1 (en) | 2012-06-29 | 2013-06-26 | Silver-containing composition |
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JP2017239844A Division JP6404444B2 (ja) | 2012-06-29 | 2017-12-14 | 銀含有組成物 |
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JP2015524485A true JP2015524485A (ja) | 2015-08-24 |
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JP2015518811A Pending JP2015524485A (ja) | 2012-06-29 | 2013-06-26 | 銀含有組成物 |
JP2017239844A Expired - Fee Related JP6404444B2 (ja) | 2012-06-29 | 2017-12-14 | 銀含有組成物 |
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JP2017239844A Expired - Fee Related JP6404444B2 (ja) | 2012-06-29 | 2017-12-14 | 銀含有組成物 |
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US (1) | US20150335012A1 (ja) |
EP (1) | EP2867307A4 (ja) |
JP (2) | JP2015524485A (ja) |
CN (2) | CN103509364B (ja) |
BR (1) | BR112014031398A2 (ja) |
IN (1) | IN2014DN10307A (ja) |
WO (1) | WO2014000638A1 (ja) |
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Publication number | Priority date | Publication date | Assignee | Title |
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CN103509362B (zh) * | 2012-06-29 | 2016-08-31 | 罗门哈斯公司 | 含银浓缩物 |
US9840626B2 (en) * | 2015-07-23 | 2017-12-12 | Xerox Corporation | Anti-bacterial aqueous ink compositions comprising metal ion composite ionomer resins |
AU2015409857B2 (en) * | 2015-09-22 | 2020-10-08 | Rohm And Haas Company | Polymer emulsion and antimicrobial coating composition comprising the same |
US20180192652A1 (en) * | 2017-01-11 | 2018-07-12 | Frank Escobedo | Antimicrobial agricultural products, manufacturing methods and application thereof |
US11337421B2 (en) * | 2019-12-24 | 2022-05-24 | Hamed Ahari | Method for producing antimicrobial nanofilms packaging cover based on Titanium nano-dioxide through extrusion for extension of food shelf-life |
US11937653B2 (en) | 2020-07-09 | 2024-03-26 | Vitiprints, LLC | Smart mask |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH11222402A (ja) * | 1998-02-04 | 1999-08-17 | Osaka Gas Co Ltd | 抗菌性ポリマー粒子およびその製造方法 |
JP2005298507A (ja) * | 2004-04-08 | 2005-10-27 | Rohm & Haas Co | 抗菌組成物ならびにその製造および使用方法 |
JP2009084174A (ja) * | 2007-09-28 | 2009-04-23 | Nippon Chem Ind Co Ltd | 抗菌剤 |
JP2015522570A (ja) * | 2012-06-29 | 2015-08-06 | ローム アンド ハース カンパニーRohm And Haas Company | 銀含有濃縮物 |
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ATE366771T1 (de) * | 2001-05-11 | 2007-08-15 | Thomas Haering | Modifikation von verstreckten folien |
EP1622973A1 (en) * | 2003-05-12 | 2006-02-08 | LG Electronics Inc. | Anti-microbial plastic composition and washing machine comprising the parts manufactured by using the same |
US7335613B2 (en) * | 2004-04-08 | 2008-02-26 | Rohm And Haas Company | Fiber substrate with antibacterial finish and methods of making and using the same |
CN1300241C (zh) * | 2004-10-15 | 2007-02-14 | 中国科学院理化技术研究所 | 抗菌高吸水性聚合物复合材料及其制备方法 |
EP1741811B1 (en) | 2005-07-07 | 2007-08-22 | Rohm and Haas Company | Fiber containing an antimicrobial composition |
CN1298222C (zh) * | 2005-08-08 | 2007-02-07 | 深圳清华大学研究院 | 液态纳米单质银抗菌剂及制备方法 |
CN1292660C (zh) * | 2005-09-01 | 2007-01-03 | 云南大学 | 一种复合抗菌剂 |
AU2006222708A1 (en) * | 2005-10-07 | 2007-04-26 | Rohm And Haas Company | Method for disinfecting or sanitizing a surface |
ZA200709364B (en) * | 2006-11-14 | 2008-11-26 | Rohm & Haas | Microbicide combinations containing silver |
KR101135571B1 (ko) * | 2009-12-01 | 2012-04-17 | (주)에이씨티 | 항균성분이 코팅된 실리카 분말의 제조방법 및 이를 포함하는 피부 외용제 조성물 |
CN102206393B (zh) * | 2010-03-31 | 2014-02-12 | 罗门哈斯公司 | 抗菌聚合物乳液和涂料组合物 |
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2012
- 2012-06-29 CN CN201210224352.6A patent/CN103509364B/zh not_active Expired - Fee Related
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2013
- 2013-06-26 BR BR112014031398A patent/BR112014031398A2/pt not_active Application Discontinuation
- 2013-06-26 EP EP13810195.1A patent/EP2867307A4/en not_active Withdrawn
- 2013-06-26 JP JP2015518811A patent/JP2015524485A/ja active Pending
- 2013-06-26 IN IN10307DEN2014 patent/IN2014DN10307A/en unknown
- 2013-06-26 WO PCT/CN2013/077949 patent/WO2014000638A1/en active Application Filing
- 2013-06-26 US US14/410,612 patent/US20150335012A1/en not_active Abandoned
- 2013-06-26 CN CN201380031581.9A patent/CN104379676A/zh active Pending
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Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
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JPH11222402A (ja) * | 1998-02-04 | 1999-08-17 | Osaka Gas Co Ltd | 抗菌性ポリマー粒子およびその製造方法 |
JP2005298507A (ja) * | 2004-04-08 | 2005-10-27 | Rohm & Haas Co | 抗菌組成物ならびにその製造および使用方法 |
JP2010260874A (ja) * | 2004-04-08 | 2010-11-18 | Rohm & Haas Co | 抗菌組成物ならびにその製造および使用方法 |
JP2009084174A (ja) * | 2007-09-28 | 2009-04-23 | Nippon Chem Ind Co Ltd | 抗菌剤 |
JP2015522570A (ja) * | 2012-06-29 | 2015-08-06 | ローム アンド ハース カンパニーRohm And Haas Company | 銀含有濃縮物 |
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IN2014DN10307A (ja) | 2015-08-07 |
WO2014000638A1 (en) | 2014-01-03 |
CN104379676A (zh) | 2015-02-25 |
BR112014031398A2 (pt) | 2017-08-22 |
US20150335012A1 (en) | 2015-11-26 |
EP2867307A1 (en) | 2015-05-06 |
CN103509364A (zh) | 2014-01-15 |
EP2867307A4 (en) | 2016-01-20 |
JP2018076522A (ja) | 2018-05-17 |
JP6404444B2 (ja) | 2018-10-10 |
CN103509364B (zh) | 2016-08-03 |
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