JPH05229911A - Antimicrobial aluminum phosphate - Google Patents
Antimicrobial aluminum phosphateInfo
- Publication number
- JPH05229911A JPH05229911A JP7297592A JP7297592A JPH05229911A JP H05229911 A JPH05229911 A JP H05229911A JP 7297592 A JP7297592 A JP 7297592A JP 7297592 A JP7297592 A JP 7297592A JP H05229911 A JPH05229911 A JP H05229911A
- Authority
- JP
- Japan
- Prior art keywords
- aluminum phosphate
- metal
- antibacterial
- antimicrobial
- ion
- 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.)
- Pending
Links
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は抗菌性を有するリン酸ア
ルミニウム、詳しくは抗菌性を有する金属イオン及び／
又は金属を担持させてなる安全な抗菌性リン酸アルミニ
ウムに関するものである。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an aluminum phosphate having an antibacterial property, more specifically a metal ion having an antibacterial property and / or
Alternatively, the present invention relates to a safe antibacterial aluminum phosphate which carries a metal.
【０００２】[0002]
【従来の技術】従来から微量で強い抗菌作用を示す金属
イオンが存在することは知られており、硝酸銀等が消毒
剤として用いられてきた。しかしながら、水溶液という
限定された使用方法の為、用途が限定され、抗菌剤とし
てあまり検討が加えられていなかった。2. Description of the Related Art It has been conventionally known that a small amount of metal ions having a strong antibacterial action exists, and silver nitrate or the like has been used as a disinfectant. However, because of its limited use as an aqueous solution, its use is limited, and it has not been studied much as an antibacterial agent.
【０００３】近年それら金属の強い抗菌性、耐熱性に注
目され、それら金属又は金属イオンをゼオライト、ガラ
ス、リン酸カルシウム、リン酸チタン、リン酸ジルコニ
ウムなどの無機物に担持させた無機系抗菌剤が種々検
討、開発され、樹脂、繊維、フィルム、紙、セラミッ
ク、塗料などに添加されて抗菌性材料として使用され始
めている。In recent years, the strong antibacterial properties and heat resistance of these metals have attracted attention, and various inorganic antibacterial agents in which these metals or metal ions are supported on inorganic substances such as zeolite, glass, calcium phosphate, titanium phosphate, zirconium phosphate, etc. have been investigated. , Has been developed and added to resins, fibers, films, papers, ceramics, paints, etc. and has begun to be used as an antibacterial material.
【０００４】しかしながら、これらの金属を担持した抗
菌剤は使用した担体、使用する媒質によって溶出量は異
なるが、金属イオンを媒質中に放出するため、長期間の
抗菌剤自体の保存性や、これらの抗菌剤を添加した成形
物の変色に問題があった。又、樹脂などへ添加した際の
分散性や、担体自体の価格が高いなどの問題があった。However, although the elution amount of these antibacterial agents carrying a metal varies depending on the carrier used and the medium used, since metal ions are released into the medium, the antibacterial agent itself has a long-term storage stability, and There was a problem in discoloration of the molded article to which the antibacterial agent was added. In addition, there are problems such as dispersibility when added to resins and the like, and the cost of the carrier itself is high.
【０００５】[0005]
【発明が解決しようとする課題】上記したように、抗菌
性金属イオンを用いた従来の無機系の抗菌剤では、まだ
金属イオンの水への溶出、変色などの問題、樹脂への分
散性、価格など、なんらかの問題が残されており、使用
法、使用範囲が狭められている。このような無機系抗菌
剤の欠点を改善し、金属イオンの水への溶出、変色が無
く、樹脂への分散性が良く、しかも安価な無機系抗菌剤
を提供することを本発明は課題としている。As described above, in the conventional inorganic antibacterial agents using antibacterial metal ions, problems such as elution of metal ions in water, discoloration, dispersibility in resin, Some problems such as price remain, and usage and range of use are narrowed. It is an object of the present invention to provide an inorganic antibacterial agent that improves the drawbacks of such an inorganic antibacterial agent, does not dissolve metal ions in water, has no discoloration, has good dispersibility in a resin, and is inexpensive. There is.
【０００６】[0006]
【課題を解決するための手段】本発明者らは、前記した
ような課題を解決するために検討した結果、抗菌性金属
イオン又は金属を担持し、金属イオンの溶出が少なく、
変色が起こらず、樹脂への分散性が良く、安価な無機系
抗菌剤である、抗菌性リン酸アルミニウム組成物を開発
することができた。Means for Solving the Problems As a result of studies for solving the above-mentioned problems, the present inventors carried antibacterial metal ions or metals, and little elution of metal ions,
It has been possible to develop an antibacterial aluminum phosphate composition that is an inexpensive inorganic antibacterial agent that does not cause discoloration, has good dispersibility in a resin, and is inexpensive.
【０００７】リン酸アルミニウムは医薬品、歯科用セメ
ント、顔料、また耐火用材として樹脂、ボード、モルタ
ルなどに広く用いられている。本発明で提供する抗菌性
リン酸アルミニウムはAlPO4 、AlPO4 ・nH2Oで示される
オルトリン酸アルミニウムや、Al(PO3)3で示されるメタ
リン酸アルミニウムに、抗菌性金属及び／又は金属イオ
ンを担持させて得られた抗菌性リン酸アルミニウム組成
物である。Aluminum phosphate is widely used in medicines, dental cements, pigments, and as fireproofing materials in resins, boards, mortars and the like. The antibacterial aluminum phosphate provided by the present invention is AlPO 4 , aluminum orthophosphate represented by AlPO 4 .nH 2 O, or aluminum metaphosphate represented by Al (PO 3 ) 3 , an antibacterial metal and / or a metal ion. Is an antibacterial aluminum phosphate composition obtained by supporting.
【０００８】本発明で使用される金属、金属イオンは
銀、銅、亜鉛、錫、鉛、ヒ素及び、コバルト、カドミウ
ムから選ばれた少なくとも１種の金属及び／又は金属イ
オンであり、実用的に特に、銀、銅及び亜鉛の金属、金
属イオンの使用が好適である。The metal or metal ion used in the present invention is at least one metal and / or metal ion selected from silver, copper, zinc, tin, lead, arsenic, cobalt and cadmium, and is practically used. In particular, the use of silver, copper and zinc metals and metal ions is preferable.
【０００９】抗菌性金属イオンを担持したリン酸アルミ
ニウムは、リン酸アルミニウムを抗菌性金属イオンを含
有する水溶液中に浸漬することにより容易に得ることが
できる。即ち、抗菌性金属の硫酸塩、硝酸塩、あるいは
金属錯体を含有する溶液中にリン酸アルミニウムを懸濁
させて、常温ないし、加温下において接触処理を行な
い、生成物を常法により水洗、乾燥し、必要に応じて粉
砕して目的物を得ることができる。又、リン酸アルミニ
ウムの湿式合成時に水溶性の抗菌性金属塩、あるいは金
属錯体を添加することにより、抗菌性金属イオンを担持
したリン酸アルミニウムを得ることができる。The aluminum phosphate carrying the antibacterial metal ion can be easily obtained by immersing the aluminum phosphate in an aqueous solution containing the antibacterial metal ion. That is, aluminum phosphate is suspended in a solution containing an antibacterial metal sulfate, nitrate, or metal complex, and contact treatment is performed at room temperature or under heating, and the product is washed with water and dried by a conventional method. Then, the desired product can be obtained by pulverizing as necessary. Further, by adding a water-soluble antibacterial metal salt or a metal complex during wet synthesis of aluminum phosphate, aluminum phosphate carrying antibacterial metal ions can be obtained.
【００１０】抗菌性金属担持リン酸アルミニウムは、こ
れらの方法で得た抗菌性金属イオン担持リン酸アルミニ
ウムを抗菌性金属の融点以上で焼成するか、水素ガスで
還元することにより得ることができる。The antibacterial metal-supported aluminum phosphate can be obtained by firing the antibacterial metal ion-supported aluminum phosphate obtained by these methods at a temperature above the melting point of the antibacterial metal or by reducing with hydrogen gas.
【００１１】リン酸アルミニウムに担持させる金属イオ
ン、金属の量は飽和置換量、飽和吸着量以下であれば差
しつかえないが、多量に担持させると、金属イオンを多
量に溶出させる場合があり、また充分な抗菌性を得るた
め、経済性も考慮して0.００１〜１５％程度が良い。The amount of metal ions and metals supported on aluminum phosphate may be equal to or less than the saturated substitution amount and the saturated adsorption amount, but when a large amount is supported, a large amount of metal ions may be eluted, and In order to obtain sufficient antibacterial property, about 0.001 to 15% is preferable in consideration of economy.
【００１２】このようにして得られた抗菌性リン酸アル
ミニウムは金属イオンを安定に担持、又は金属を均質に
分散させているため、長期間変色もなく、安全に使用で
きる。本願の抗菌性組成物は、用途に応じて適便他の材
料に混合、複合することができ、特に使用方法、添加量
などの制限はない。例えば樹脂、紙、セラミック、ガラ
ス、粉末、液体、塗料、フィルム、繊維、フィルター、
等に分散性良く添加でき、高い抗菌力を発揮することが
できる。しかし、このように他材に添加することを考慮
すると、粒径は小さいほうが良く、１０μm 以下が望ま
しい。以下、実施例を示して本発明を具体的に説明す
る。The antibacterial aluminum phosphate thus obtained supports metal ions stably or disperses the metal homogeneously, and therefore can be safely used without discoloration for a long period of time. The antibacterial composition of the present application can be appropriately mixed and mixed with other materials depending on the application, and there are no particular restrictions on the method of use, the amount added, and the like. For example, resin, paper, ceramic, glass, powder, liquid, paint, film, fiber, filter,
Etc. can be added with good dispersibility, and can exhibit high antibacterial activity. However, in consideration of such addition to other materials, it is better that the particle size is smaller, and 10 μm or less is desirable. Hereinafter, the present invention will be specifically described with reference to examples.
【００１３】〔実施例１−１〕蒸留水５０ml中に硝酸銀
を0.２mg溶解した水溶液中にオルトリン酸アルミニウム
を１０ｇ加えて撹拌する。生成物を蒸留水で洗浄、ロ過
し、乾燥して銀イオンを約0.００１重量％担持した粉末
を得た。[Example 1-1] 10 g of aluminum orthophosphate was added to an aqueous solution prepared by dissolving 0.2 mg of silver nitrate in 50 ml of distilled water and stirred. The product was washed with distilled water, filtered, and dried to obtain a powder carrying about 0.001% by weight of silver ion.
【００１４】〔実施例２−１〕蒸留水５０ml中にヒ酸水
素二ナトリウムを５mg溶解した水溶液中に、メタリン酸
アルミニウムを１０ｇ加えて撹拌する。生成物を蒸留水
で洗浄、ロ過し、乾燥してヒ素イオンを約0.０１重量％
担持した粉末を得た。Example 2-1 10 g of aluminum metaphosphate was added to an aqueous solution prepared by dissolving 5 mg of disodium hydrogen arsenate in 50 ml of distilled water and stirred. The product is washed with distilled water, filtered, and dried to obtain about 0.01% by weight of arsenic ion.
A supported powder was obtained.
【００１５】〔実施例３−１〕蒸留水５０ml中に硫酸カ
ドミウムを２０mg溶解した水溶液中に、オルトリン酸ア
ルミニウムを１０ｇ加えて撹拌する。生成物を蒸留水で
洗浄、ロ過し、乾燥してカドミウムイオンを約0.１重量
％担持した粉末を得た。Example 3-1 10 g of aluminum orthophosphate is added to an aqueous solution prepared by dissolving 20 mg of cadmium sulfate in 50 ml of distilled water and stirred. The product was washed with distilled water, filtered, and dried to obtain a powder carrying about 0.1% by weight of cadmium ion.
【００１６】〔実施例４−１〕硫酸銅0.４ｇを蒸留水に
溶解させた溶液１００ml中に、リン酸ナトリウム１４ｇ
を溶解させた溶液と硝酸アルミニウム９水和物３８ｇを
溶解させた溶液を加えて、生成物を得る。この生成物を
蒸留水で洗浄、ロ過し、乾燥して銅イオンを約１重量％
担持したオルトリン酸アルミニウムを得た。Example 4-1 14 g of sodium phosphate was added to 100 ml of a solution prepared by dissolving 0.4 g of copper sulfate in distilled water.
And a solution in which 38 g of aluminum nitrate nonahydrate are dissolved are added to obtain a product. This product was washed with distilled water, filtered, and dried to contain about 1% by weight of copper ion.
The supported aluminum orthophosphate was obtained.
【００１７】〔実施例５−１〕蒸留水５０ml中に塩化第
一錫を0.３５ｇ溶解した水溶液中に、メタリン酸アルミ
ニウムを１０ｇ加えて撹拌する。生成物を蒸留水で洗
浄、ロ過し、乾燥して錫イオンを約２重量％担持した粉
末を得た。Example 5-1 10 g of aluminum metaphosphate was added to an aqueous solution prepared by dissolving 0.35 g of stannous chloride in 50 ml of distilled water and stirred. The product was washed with distilled water, filtered, and dried to obtain a powder carrying about 2% by weight of tin ions.
【００１８】〔実施例６−１〕硝酸アルミニウム９水和
物３８ｇを溶解した溶液にリン酸9.８ｇを加え、この混
合溶液に１０％アンモニア水をpHが７以上になるように
加えて生成物を得る。この生成物を蒸留水で洗浄後、蒸
留水を加えて５０mlとする。この溶液中に硝酸銀を0.７
５ｇ加えて撹拌する。再び生成物を蒸留水で洗浄、ロ過
し、乾燥して銀イオンを約３重量％担持したオルトリン
酸アルミニウムを得た。[Example 6-1] 9.8 g of phosphoric acid was added to a solution in which 38 g of aluminum nitrate nonahydrate was dissolved, and 10% aqueous ammonia was added to this mixed solution so that the pH became 7 or more. Get things. After washing this product with distilled water, distilled water is added to make up to 50 ml. Silver nitrate is added to 0.7 in this solution.
Add 5 g and stir. The product was washed again with distilled water, filtered, and dried to obtain aluminum orthophosphate carrying about 3% by weight of silver ion.
【００１９】〔実施例７−１〕蒸留水５０ml中に塩化コ
バルトを2.１ｇ溶解した水溶液中に、オルトリン酸アル
ミニウムを１０ｇ加えて撹拌する。生成物を蒸留水で洗
浄、ロ過し、乾燥してコバルトイオンを約５重量％担持
した粉末を得た。Example 7-1 10 g of aluminum orthophosphate is added to an aqueous solution in which 2.1 g of cobalt chloride is dissolved in 50 ml of distilled water, and the mixture is stirred. The product was washed with distilled water, filtered, and dried to obtain a powder carrying about 5% by weight of cobalt ion.
【００２０】〔実施例８−１〕蒸留水５０ml中に硝酸鉛
を1.７ｇ溶解した水溶液中に、メタリン酸アルミニウム
を１０ｇ加えて撹拌する。生成物を蒸留水で洗浄、ロ過
し、乾燥して鉛イオンを約１０重量％担持した粉末を得
た。Example 8-1 10 g of aluminum metaphosphate was added to an aqueous solution prepared by dissolving 1.7 g of lead nitrate in 50 ml of distilled water and stirred. The product was washed with distilled water, filtered, and dried to obtain a powder carrying about 10% by weight of lead ions.
【００２１】〔実施例９−１〕蒸留水５０ml中に硝酸亜
鉛を７ｇ溶解した水溶液中に、オルトリン酸アルミニウ
ムを１０ｇ加えて撹拌する。生成物を蒸留水で洗浄、ロ
過し、乾燥して亜鉛イオンを約１５重量％担持した粉末
を得た。Example 9-1 10 g of aluminum orthophosphate was added to an aqueous solution in which 7 g of zinc nitrate was dissolved in 50 ml of distilled water, and the mixture was stirred. The product was washed with distilled water, filtered, and dried to obtain a powder carrying about 15% by weight of zinc ion.
【００２２】〔実施例１０〕実施例１−１〜実施例９−
１で得た抗菌性粉末を焼成してそれぞれの金属を担持し
た抗菌性リン酸アルミニウムを得た。〔実施例１−２〕
〜〔実施例９−２〕 実施例１−２及び実施例６−２は、実施例１−１及び実
施例６−１でえられた粉末を1,000 ℃、実施例２−２及
び実施例９−２は、実施例２−１及び実施例９−１でえ
られた粉末を９００℃、実施例３−２、実施例５−２及
び実施例８−２は、実施例３−１、実施例５−１及び実
施例８−１でえられた粉末を５００℃、実施例４−２は
実施例４−１でえられた粉末を１２００℃、実施例７−
２は実施例７−１でえられた粉末を１５００℃で夫々焼
成した。[Embodiment 10] Embodiments 1-1 to 9-
The antibacterial powder obtained in 1 was fired to obtain antibacterial aluminum phosphate carrying each metal. [Example 1-2]
-[Example 9-2] In Example 1-2 and Example 6-2, the powder obtained in Example 1-1 and Example 6-1 was 1,000 ° C, Example 2-2 and Example 9 were used. -2, the powder obtained in Example 2-1 and Example 9-1 was 900 ° C., Example 3-2, Example 5-2 and Example 8-2 were Example 3-1 and Example 3-2. The powder obtained in Example 5-1 and Example 8-1 was 500 ° C., Example 4-2 was the powder obtained in Example 4-1 1200 ° C., Example 7-
In No. 2, the powder obtained in Example 7-1 was fired at 1500 ° C., respectively.
【００２３】〔実施例１１〕抗菌力試験 リン酸緩衝液で調整した、5.２×１０4 個／mlの大腸菌
液に、実施例１−１〜実施例９−２のそれぞれの試料を
１重量％添加して、大腸菌に対する抗菌力を測定した。
その結果、何れも２４時間で菌が検出されなかった。[Example 11] Antibacterial activity test One sample of each of Examples 1-1 to 9-2 was added to 5.2 × 10 4 cells / ml of Escherichia coli solution prepared with a phosphate buffer. The antibacterial activity against Escherichia coli was measured by adding the composition in a weight percentage.
As a result, no bacterium was detected in 24 hours.
【００２４】〔実施例１２〕金属溶出試験 実施例１−１〜実施例９−２で作成した粉末それぞれ１
ｇづつを蒸留水１００ml中に添加し、１時間撹拌したと
き、抗菌性金属の溶出量は何れも0.２ppm 以下であっ
た。[Example 12] Metal elution test [0024] 1 of each of the powders prepared in Examples 1-1 to 9-2
When each g was added to 100 ml of distilled water and stirred for 1 hour, the elution amount of the antibacterial metal was 0.2 ppm or less in all cases.
【００２５】[0025]
【発明の効果】本発明による抗菌性リン酸アルミニウム
は簡単な方法でえられ、水と処理しても担持された抗菌
性金属又は金属イオンが水に溶出することがないので安
全に使用でき、樹脂、繊維、セラミックなどの有機、無
機物質と容易に混合、分散するので、樹脂成型物、紙、
塗料、フィルム、フィルター、繊維などに分散性よく添
加でき、それら物質に高い抗菌性を付与できる。INDUSTRIAL APPLICABILITY The antibacterial aluminum phosphate according to the present invention can be obtained by a simple method and can be safely used because the supported antibacterial metal or metal ion does not elute in water even when treated with water. Easily mix and disperse with organic and inorganic substances such as resins, fibers and ceramics, so resin moldings, paper,
It can be added to paints, films, filters, fibers, etc. with good dispersibility and can impart high antibacterial properties to these substances.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.5 識別記号 庁内整理番号 ＦＩ 技術表示箇所 Ａ０１Ｎ 59/22 7106−4Ｈ 59/26 7106−4Ｈ ─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 5 Identification code Office reference number FI technical display location A01N 59/22 7106-4H 59/26 7106-4H
Claims (3)
酸アルミニウムに担持させたことを特徴とする抗菌性リ
ン酸アルミニウム。1. An antibacterial aluminum phosphate in which an antibacterial metal and / or a metal ion is supported on aluminum phosphate.
銅、亜鉛、錫、鉛、ヒ素、コバルト及びカドミウムから
選ばれた少くとも１種の金属及び／又は金属イオンであ
る請求項１の抗菌性リン酸アルミニウム。2. The antibacterial metal and / or metal ion is silver,
The antibacterial aluminum phosphate according to claim 1, which is at least one metal and / or metal ion selected from copper, zinc, tin, lead, arsenic, cobalt and cadmium.
量がリン酸アルミニウムに対し重量で0.００１〜１５％
である請求項１又は２の抗菌性リン酸アルミニウム。3. The amount of the antibacterial metal and / or metal ion supported is 0.001 to 15% by weight based on aluminum phosphate.
The antibacterial aluminum phosphate according to claim 1 or 2.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7297592A JPH05229911A (en) | 1992-02-26 | 1992-02-26 | Antimicrobial aluminum phosphate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7297592A JPH05229911A (en) | 1992-02-26 | 1992-02-26 | Antimicrobial aluminum phosphate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH05229911A true JPH05229911A (en) | 1993-09-07 |
Family
ID=13504906
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7297592A Pending JPH05229911A (en) | 1992-02-26 | 1992-02-26 | Antimicrobial aluminum phosphate |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH05229911A (en) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5961843A (en) * | 1994-10-05 | 1999-10-05 | Toto Ltd. | Antimicrobial solid material, process for producing the same, and method of utilizing the same |
| WO2005003033A3 (en) * | 2002-12-23 | 2005-04-28 | Applied Thin Films Inc | Aluminum phosphate coatings |
| KR100704010B1 (en) * | 2005-07-25 | 2007-04-04 | 주식회사 엘지화학 | Method for preparing ceramic filter and ceramic filter prepared by the same |
| WO2008055967A3 (en) * | 2006-11-09 | 2008-10-16 | Werner Zapletal | Powdery additives for the production of paper |
| US7678465B2 (en) | 2002-07-24 | 2010-03-16 | Applied Thin Films, Inc. | Aluminum phosphate compounds, compositions, materials and related metal coatings |
| US7682700B2 (en) | 2002-08-14 | 2010-03-23 | Applied Thin Films, Inc. | Aluminum phosphate compounds, compositions, materials and related composites |
| WO2013158575A1 (en) * | 2012-04-16 | 2013-10-24 | Bunge Amorphic Solutions Llc | Antimicrobial chemical compositions |
| US9078445B2 (en) | 2012-04-16 | 2015-07-14 | Bunge Amorphic Solutions Llc | Antimicrobial chemical compositions |
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1992
- 1992-02-26 JP JP7297592A patent/JPH05229911A/en active Pending
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5961843A (en) * | 1994-10-05 | 1999-10-05 | Toto Ltd. | Antimicrobial solid material, process for producing the same, and method of utilizing the same |
| US7678465B2 (en) | 2002-07-24 | 2010-03-16 | Applied Thin Films, Inc. | Aluminum phosphate compounds, compositions, materials and related metal coatings |
| US8124184B2 (en) | 2002-07-24 | 2012-02-28 | Applied Thin Films, Inc. | Aluminum phosphate compounds, compositions, materials and related metal coatings |
| US7682700B2 (en) | 2002-08-14 | 2010-03-23 | Applied Thin Films, Inc. | Aluminum phosphate compounds, compositions, materials and related composites |
| WO2005003033A3 (en) * | 2002-12-23 | 2005-04-28 | Applied Thin Films Inc | Aluminum phosphate coatings |
| US7311944B2 (en) | 2002-12-23 | 2007-12-25 | Applied Thin Films, Inc. | Aluminum phosphate coatings |
| KR100704010B1 (en) * | 2005-07-25 | 2007-04-04 | 주식회사 엘지화학 | Method for preparing ceramic filter and ceramic filter prepared by the same |
| WO2008055967A3 (en) * | 2006-11-09 | 2008-10-16 | Werner Zapletal | Powdery additives for the production of paper |
| WO2013158575A1 (en) * | 2012-04-16 | 2013-10-24 | Bunge Amorphic Solutions Llc | Antimicrobial chemical compositions |
| WO2013158509A1 (en) * | 2012-04-16 | 2013-10-24 | Bunge Amorphic Solutions Llc | Antimicrobial chemical compositions |
| US9078445B2 (en) | 2012-04-16 | 2015-07-14 | Bunge Amorphic Solutions Llc | Antimicrobial chemical compositions |
| US20150313239A1 (en) * | 2012-04-16 | 2015-11-05 | Bunge Amorphic Solutions Llc | Antimicrobial chemical compositions |
| EP3189732A1 (en) * | 2012-04-16 | 2017-07-12 | Bunge Amorphic Solutions LLC | Antimicrobial chemical compositions |
| US9801385B2 (en) | 2012-04-16 | 2017-10-31 | Bunge Amorphic Solutions Llc | Antimicrobial chemical compositions |
| US9155311B2 (en) | 2013-03-15 | 2015-10-13 | Bunge Amorphic Solutions Llc | Antimicrobial chemical compositions |
| US9955700B2 (en) | 2013-03-15 | 2018-05-01 | Bunge Amorphic Solutions Llc | Antimicrobial chemical compositions |
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