JP2002053412A - Microencapsulated preparation involving 2-n-octyl-4- isothiazolin-3-one - Google Patents
Microencapsulated preparation involving 2-n-octyl-4- isothiazolin-3-oneInfo
- Publication number
- JP2002053412A JP2002053412A JP2000275661A JP2000275661A JP2002053412A JP 2002053412 A JP2002053412 A JP 2002053412A JP 2000275661 A JP2000275661 A JP 2000275661A JP 2000275661 A JP2000275661 A JP 2000275661A JP 2002053412 A JP2002053412 A JP 2002053412A
- Authority
- JP
- Japan
- Prior art keywords
- oit
- resin
- added
- isothiazolin
- octyl
- 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
Classifications
-
- 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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/14—Paints containing biocides, e.g. fungicides, insecticides or pesticides
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、防カビ剤である２
−ｎ−オクチル−４−イソチアゾリン−３−オン（以
下、ＯＩＴと呼称）がマイクロカプセル化されてなる防
カビ組成物であって、該マイクロカプセルの被膜材がメ
ラミン樹脂、ポリウレタン樹脂、ポリウレア樹脂、ポリ
アミド樹脂、ポリエステル樹脂及びこれらの複合材料で
あることを特徴とするマイクロカプセル化された防カビ
組成物に関する。FIELD OF THE INVENTION The present invention relates to a fungicide,
-An antifungal composition in which -n-octyl-4-isothiazolin-3-one (hereinafter referred to as OIT) is microencapsulated, wherein the coating material of the microcapsule is a melamine resin, a polyurethane resin, a polyurea resin, The present invention relates to a microencapsulated antifungal composition characterized by being a polyamide resin, a polyester resin and a composite material thereof.
【０００２】[0002]
【従来の技術】水性塗料に対する防カビ剤ＯＩＴの使用
方法は、疏水性であるＯＩＴを乳化剤の作用により親水
化して添加する方法である。しかし、このような方法で
は塗料表面からＯＩＴが容易に溶出してしまうため、速
効性には優れているが持続性に欠け、特に屋外暴露試験
において長期間防カビ効果を持続することが困難であ
る。2. Description of the Related Art A method of using a fungicide OIT for a water-based paint is a method in which a hydrophobic OIT is hydrophilized by the action of an emulsifier and added. However, in such a method, the OIT is easily eluted from the paint surface, so that it is excellent in immediate effect but lacks sustainability, and it is difficult to maintain a long-term fungicidal effect especially in an outdoor exposure test. is there.
【０００３】[0003]
【発明が解決しようとする課題】水性塗料への防カビ加
工剤として、ＯＩＴを乳化剤の作用により親水化して添
加する方法では、長期間防カビ効果を持続することは期
待できない。これを解決する方法として、疏水性のＯＩ
Ｔをマイクロカプセル化して親水化し、水系塗料に添加
した例はまだ知られていない。また、このマイクロカプ
セル化により、ＯＩＴの皮膚刺激性が緩和するととも
に、様々な水系製品に添加可能なマイクロカプセル剤が
得られると期待される。In a method in which OIT is added as a fungicide processing agent to a water-based paint by making it hydrophilic by the action of an emulsifier, it is not expected that the fungicide-proof effect will be maintained for a long time. As a solution to this, a hydrophobic OI
There is no known example in which T is microencapsulated to make it hydrophilic and added to a water-based paint. The microencapsulation is expected to reduce the skin irritation of the OIT and provide a microcapsule that can be added to various water-based products.
【０００４】本発明では、防カビ剤ＯＩＴをマイクロカ
プセル化することにより、持続性に優れた防カビ効果を
有するマイクロカプセルを製造するために研究を行なっ
た。In the present invention, a study was conducted to produce a microcapsule having a long-lasting fungicide effect by microencapsulating the fungicide OIT.
【０００５】[0005]
【課題を解決するための手段】水性塗料への防カビ加工
剤として、ＯＩＴを乳化剤の作用により添加する方法で
は、長期間防カビ効果を持続することは期待できない。
これを解決するための手段としては、芯物質と芯物質の
周囲に形成された被膜材とからなるマイクロカプセルに
おいて、芯物質がＯＩＴであり、被膜材がメラミン樹
脂、ポリウレタン樹脂、ポリウレア樹脂、ポリアミド樹
脂、ポリエステル樹脂及びこれらの複合材料であること
を特徴とするマイクロカプセル化された防カビ組成物を
製造して、水性塗料に添加する方法が有効であることを
見い出した。SUMMARY OF THE INVENTION A method in which OIT is added as an antifungal agent to an aqueous paint by the action of an emulsifier cannot be expected to maintain the antifungal effect for a long time.
As means for solving this, in a microcapsule comprising a core material and a coating material formed around the core material, the core material is OIT, and the coating material is melamine resin, polyurethane resin, polyurea resin, polyamide. It has been found that a method of producing a microencapsulated antifungal composition characterized by being a resin, a polyester resin and a composite material thereof and adding the composition to a water-based paint is effective.
【０００６】本発明の製剤では芯物質としてのＯＩＴを
メラミン樹脂、ポリウレタン樹脂、ポリウレア樹脂、ポ
リアミド樹脂、ポリエステル樹脂及これらの複合材料で
周囲の環境から保護することにより、また、芯物質と被
膜材の割合を調節することにより、水性塗料中への芯物
質の溶出を抑制し、速効性及び持続性に優れた防カビ効
果を有するマイクロカプセル化防カビ製剤の提供が可能
となる。In the preparation of the present invention, OIT as a core substance is protected from the surrounding environment by a melamine resin, a polyurethane resin, a polyurea resin, a polyamide resin, a polyester resin and a composite material thereof, and the core substance and the coating material are protected. By controlling the proportion of the antimicrobial agent, it is possible to provide a microencapsulated antifungal preparation having an antifungal effect excellent in quick action and durability by suppressing elution of the core substance into the aqueous paint.
【０００７】ＯＩＴを芯物質とし、ＯＩＴの溶出速度を
調節可能な被膜材であって、しかも、その防カビ効果を
低下させることのない被膜材によりＯＩＴをマイクロカ
プセル化する方法としては、マイクロカプセル生成技術
において広く公知の界面重合法、ｉｎ−ｓｉｔｕ法、相
分離法、液中硬化被覆法、液中乾燥法及び噴霧・造粒法
等が利用できるが、中でも界面重合法は目的とするＯＩ
Ｔのマイクロカプセル化を効果的に可能にするので有用
である。[0007] As a method of microencapsulating OIT with a coating material that uses OIT as a core substance and that can control the elution rate of OIT and that does not reduce its antifungal effect, microcapsules are used. Widely known interfacial polymerization methods, in-situ methods, phase separation methods, in-liquid curing coating methods, in-liquid drying methods, spraying / granulation methods, and the like can be used in the production technology.
Useful because it effectively allows microencapsulation of T.
【０００８】本発明において用いられる被膜材として
は、ＯＩＴに対して徐放性を有する物質であればいずれ
も使用可能であるが、特にメラミン樹脂、ポリウレタン
樹脂、ポリウレア樹脂、ポリアミド樹脂、ポリエステル
樹脂及びこれらの複合材料が挙げられる。As the coating material used in the present invention, any substance can be used as long as it has a sustained release property to OIT. In particular, melamine resin, polyurethane resin, polyurea resin, polyamide resin, polyester resin and These composite materials are mentioned.
【０００９】本発明におけるＯＩＴを含む芯物質と被膜
材の好ましい割合については特に限定されないが、長期
間防カビ効果を持続させるためには被膜材は多いことが
好ましいが、速効性を考慮すると被膜材は少ないことが
好ましい。芯物質と被膜材の好ましい重量比は１：５〜
１：０．０１であるが、速効性及び持続性を考慮した場
合には１：２〜１：０．１であることが好ましい。The preferred ratio of the core material containing OIT and the coating material in the present invention is not particularly limited, but it is preferable that the coating material is large in order to maintain the antifungal effect for a long period of time. Preferably, the material is small. The preferred weight ratio between the core material and the coating material is 1: 5
The ratio is 1: 0.01, but is preferably from 1: 2 to 1: 0.1 in consideration of immediate action and sustainability.
【００１０】本発明のＯＩＴを内包したマイクロカプセ
ル化製剤は、長期間にわたって防カビ効果を必要とする
場合には、水性塗料及び水性製品に対してマイクロカプ
セル化製剤として０．０１％〜２０％添加して使用する
ことが好ましい。[0010] The microencapsulated preparation containing the OIT of the present invention can be used as a microencapsulated preparation in an amount of 0.01% to 20% with respect to an aqueous paint and an aqueous product when a fungicidal effect is required for a long period of time. It is preferable to use it by adding it.
【００１１】以下、実施例により詳細説明する。しか
し、本発明はこれらの実施例に限定されるものではな
い。Hereinafter, the present invention will be described in detail with reference to embodiments. However, the present invention is not limited to these examples.
【００１２】[0012]
【実施例】（実験例１）スチレン−無水マレイン酸樹脂
（サンモント社製 スクリプセット５２０）１０ｇを水
４８ｇに溶解した後、酢酸２ｇを加えてｐＨを４．５に
調節した。これにＯＩＴ（ローム・アンド・ハース株式
会社製 ケーソン８９３Ｔ）を２０ｇ加え、平均粒径が
５μｍになるまでホモミキサーで乳化を行なった。得ら
れた乳化物をゆっくり撹拌しながら、メラミン樹脂（住
友化学工業株式会社製 スミレッツレジン６１３）５０
％水溶液を少量ずつ２０ｇ加えた。これを６５℃で２時
間撹拌してメラミン樹脂被膜のマイクロカプセル分散液
を得た。 （実験例２）ＯＩＴ２０ｇに多価イソシアネート（日本
ポリウレタン工業株式会社製 ミリオネートＭＲ−２０
０）を８ｇ加えた後、２％ポリビニルアルコール（信越
化学工業株式会社製 ＭＡ−１７）水溶液５０ｇに添加
し、平均粒径が５μｍになるまでホモミキサーで乳化を
行なった。得られた乳化物をゆっくり撹拌しながら、エ
チレングリコール１０％水溶液を少量ずつ２２ｇ加え
た。これを６５℃で３時間撹拌してポリウレタン樹脂被
膜のマイクロカプセル分散液を得た。 （実験例３）ＯＩＴ２０ｇに多価イソシアネート８ｇ加
えた後、２％ポリビニルアルコール水溶液５０ｇに添加
し、平均粒径が５μｍになるまでホモミキサーで乳化を
行なった。得られた乳化物をゆっくり撹拌しながら、ヘ
キサメチレンジアミン１０％水溶液を少量ずつ２２ｇ加
えた。これを６５℃で３時間撹拌してポリウレア樹脂被
膜のマイクロカプセル分散液を得た。 （比較例１）ＯＩＴ２０ｇに乳化剤（三洋化成工業株式
会社製 ノニポール１００）を１５ｇを添加してよく撹
拌した後、ジエチレングリコールモノエチルエーテル６
５ｇに溶解してＯＩＴ自己乳化物を得た。EXAMPLES (Experimental Example 1) 10 g of styrene-maleic anhydride resin (Scripset 520 manufactured by Sunmont) was dissolved in 48 g of water, and 2 g of acetic acid was added to adjust the pH to 4.5. 20 g of OIT (Caisson 893T manufactured by Rohm and Haas Co., Ltd.) was added thereto, and the mixture was emulsified with a homomixer until the average particle size became 5 μm. While slowly stirring the obtained emulsion, melamine resin (Sumitetsu Chemical Co., Ltd. Sumiretz Resin 613) 50
A 20% aqueous solution was added in small portions. This was stirred at 65 ° C. for 2 hours to obtain a melamine resin coating microcapsule dispersion. (Experimental example 2) 20g of OIT and polyvalent isocyanate (Millionate MR-20 manufactured by Nippon Polyurethane Industry Co., Ltd.)
After adding 8 g of 0), the mixture was added to 50 g of a 2% aqueous solution of polyvinyl alcohol (MA-17, manufactured by Shin-Etsu Chemical Co., Ltd.), and emulsified with a homomixer until the average particle size became 5 μm. While slowly stirring the obtained emulsion, 22 g of a 10% aqueous solution of ethylene glycol was added little by little. This was stirred at 65 ° C. for 3 hours to obtain a microcapsule dispersion of a polyurethane resin film. (Experimental Example 3) 8 g of polyisocyanate was added to 20 g of OIT, and then added to 50 g of a 2% aqueous solution of polyvinyl alcohol, and emulsified by a homomixer until the average particle size became 5 μm. While slowly stirring the obtained emulsion, 22 g of a 10% aqueous solution of hexamethylenediamine was added little by little. This was stirred at 65 ° C for 3 hours to obtain a microcapsule dispersion of a polyurea resin film. (Comparative Example 1) To 20 g of OIT, 15 g of an emulsifier (Nonipol 100 manufactured by Sanyo Chemical Industry Co., Ltd.) was added, and the mixture was stirred well, and then diethylene glycol monoethyl ether 6 was added.
It was dissolved in 5 g to obtain an OIT self-emulsified product.
【００１３】（防カビ試験方法）実施例１から３で得ら
れたマイクロカプセル分散液及び比較例１で得られたＯ
ＩＴ自己乳化物の防カビ試験は、次に示す方法で行っ
た。マイクロカプセル分散液及びＯＩＴ自己乳化物をア
クリル系水性塗料に対して、それぞれ各１％添加し、こ
れをポリプロピレン板（縦２ｃｍ、横２ｃｍ、厚さ０．
１ｍｍ）に２０ｇ／ｍ２塗工したものを試験試料とし
た。防カビ試験結果は表１に示す。 防カビ試験・・ＪＩＳ Ｚ−２９１１による。 供試カビ Ａｓｐｅｒｇｉｌｌｕｓ ｎｉｇｅｒ ＦＥＲＭ Ｓ −１ Ｐｅｎｉｃｉｌｌｉｕｍ ｃｉｔｒｉｎｕｍ ＦＥＲ Ｍ Ｓ−５ Ｃｌａｄｏｓｐｏｒｉｕｍ ｃｌａｄｏｓｐｏｒｉｏ ｉｄｅｓ ＦＥＲＭ Ｓ−８ Ｇｌｉｏｃｌａｄｉｕｍ ｖｉｒｅｎｓ ＦＥＲＭ Ｓ−１０ Ａｕｒｅｏｂａｓｉｄｉｕｍ ｐｕｌｌｕｌａｎｓ ＦＥＲＭ Ｓ−９ 判定方法 次の表に示す表示方法による。 カビ抵抗性表示 カ ビ の 発 育 ３ 試料に接種したカビの発育が認められない。 ２ 試料に接種したカビの発育面積が１／３を超えない。 １ 試料に接種したカビの発育面積が１／３を超える。 （註）この表示方法において、表示３でさらに試料の周囲に阻止帯がある 場合には、その阻止帯の大きさをｍｍ数で右側に表示する。(Test method for antifungal test) The microcapsule dispersions obtained in Examples 1 to 3 and the O capsules obtained in Comparative Example 1
The antifungal test of the IT self-emulsified product was performed by the following method. The microcapsule dispersion and the OIT self-emulsifier were each added to an acrylic water-based paint at 1% each, and this was added to a polypropylene plate (length 2 cm, width 2 cm, thickness of 0.1 cm).
1 mm) was coated at 20 g / m 2 as a test sample. Table 1 shows the results of the antifungal test. Anti-mold test: According to JIS Z-2911. Test mold Aspergillus niger FERM S-1 Penicillium citrinum FER Ms-5 Method of cladosporium cladosporioides FERM S-8 Gli cladium virus Indication of mold resistance Mold growth 3 Mold growth inoculated on the sample was not observed. 2 The growth area of the mold inoculated on the sample does not exceed 1/3. 1 The growth area of the mold inoculated on the sample exceeds 1/3. (Note) In this display method, if there is a stop band around the sample in Display 3, the size of the stop band is displayed on the right side in mm.
【００１４】（屋外暴露試験）実施例１から３で得られ
たマイクロカプセル分散液及び比較例１で得られたＯＩ
Ｔ自己乳化物の屋外暴露性試験は、次に示す方法で行っ
た。マイクロカプセル分散液及びＯＩＴ自己乳化物をア
クリル系水性塗料に対して、それぞれ各２％添加し、こ
れをスレート板（縦５０ｃｍ、横１０ｃｍ、厚さ０．５
ｃｍ）に３００ｇ／ｍ２塗工したものを試験試料とし
た。この板を湿気の多い日陰地の土壌に垂直に半分まで
埋没させ放置し、試験期間後取り出して試験試料表面
（土壌に埋没していない部分）にカビによる変色が発生
しているか確認した。屋外暴露性試験の試験結果は表２
に示す。(Outdoor exposure test) The microcapsule dispersions obtained in Examples 1 to 3 and the OI obtained in Comparative Example 1
The outdoor exposure test of the T self-emulsified product was performed by the following method. The microcapsule dispersion and the OIT self-emulsifier were each added to the acrylic water-based paint at a rate of 2%, respectively, and the slate plate (50 cm long, 10 cm wide, 0.5 mm thick) was added.
what was 300 g / m 2 coated was tested samples cm). This plate was buried halfway vertically in a humid shaded soil and allowed to stand. After the test period, the plate was taken out and checked for discoloration due to mold on the surface of the test sample (portion not buried in the soil). Table 2 shows the results of the outdoor exposure test.
Shown in
【００１５】[0015]
【表１】 [Table 1]
【００１６】[0016]
【表２】 [Table 2]
【００１７】[0017]
【発明の効果】本発明のＯＩＴ内包マイクロカプセル化
製剤は、表１から明らかなように、水性塗料に添加した
場合に良好な防カビ効果を示し、その効果が速効性を有
する事が明らかとなった。また、表２に示されるよう
に、屋外暴露性試験においてＯＩＴ内包マイクロカプセ
ル化製剤を添加した水性塗料にカビの発生が確認されな
かった事から、ＯＩＴ内包マイクロカプセル化製剤の防
カビ効果が長期間持続する事も示された。As is clear from Table 1, the OIT-encapsulated microencapsulated preparation of the present invention shows a good antifungal effect when added to an aqueous paint, and has an immediate effect. became. In addition, as shown in Table 2, no mold was observed in the aqueous paint to which the OIT-encapsulated microencapsulated preparation was added in the outdoor exposure test, so that the fungicidal effect of the OIT-encapsulated microencapsulated preparation was long. It was also shown to last for a period.
───────────────────────────────────────────────────── フロントページの続き Ｆターム(参考） 4H011 AA03 BA01 BB10 BC03 BC04 BC06 BC18 BC19 DA06 DA15 DD07 DH02 DH04 DH05 DH19 ──────────────────────────────────────────────────続 き Continued on the front page F term (reference) 4H011 AA03 BA01 BB10 BC03 BC04 BC06 BC18 BC19 DA06 DA15 DD07 DH02 DH04 DH05 DH19
Claims (1)
イソチアゾリン−３−オンがマイクロカプセル化されて
なる防カビ組成物であって、該マイクロカプセルの被膜
材がメラミン樹脂、ポリウレタン樹脂、ポリウレア樹
脂、ポリアミド樹脂、ポリエステル樹脂及びこれらの複
合材料であることを特徴とするマイクロカプセル化され
た防カビ組成物。1. A fungicide, 2-n-octyl-4-
A fungicidal composition comprising microcapsules of isothiazolin-3-one, wherein the coating material of the microcapsules is a melamine resin, a polyurethane resin, a polyurea resin, a polyamide resin, a polyester resin, and a composite material thereof. A microencapsulated antifungal composition characterized by the following:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000275661A JP2002053412A (en) | 2000-08-09 | 2000-08-09 | Microencapsulated preparation involving 2-n-octyl-4- isothiazolin-3-one |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000275661A JP2002053412A (en) | 2000-08-09 | 2000-08-09 | Microencapsulated preparation involving 2-n-octyl-4- isothiazolin-3-one |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2002053412A true JP2002053412A (en) | 2002-02-19 |
Family
ID=18761249
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000275661A Pending JP2002053412A (en) | 2000-08-09 | 2000-08-09 | Microencapsulated preparation involving 2-n-octyl-4- isothiazolin-3-one |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2002053412A (en) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006032019A1 (en) | 2004-09-14 | 2006-03-23 | Microtek Laboratories, Inc. | Microencapsulation of biocides and antifouling agents |
| EP1698672A3 (en) * | 2002-06-19 | 2006-09-20 | THOR GmbH | Coating material with biocide microcapsules |
| US7377968B2 (en) * | 2006-03-16 | 2008-05-27 | Rohm And Haas Company | Blends of encapsulated biocides |
| DE102006061890A1 (en) | 2006-12-28 | 2008-07-03 | Thor Gmbh | Adhesives and sealants, e.g. for use in building or vehicle construction, containing active biocidal agents, especially 2-n-octyl-4-isothiazolin-3-one, encapsulated in resin-based microparticles |
| WO2008000797A3 (en) * | 2006-06-30 | 2009-01-22 | Thor Gmbh | Antimicrobial microparticles |
| EP2801256A1 (en) | 2013-05-08 | 2014-11-12 | LANXESS Deutschland GmbH | Microcapsules containing an algicide and a melamine-formaldehyde polymer |
| US10212935B2 (en) | 2014-02-27 | 2019-02-26 | Lanxess Deutschland Gmbh | Biocidic microcapsules |
| WO2020099567A1 (en) | 2018-11-16 | 2020-05-22 | Lonza Ltd | Encapsulated biocides |
| CN113845793A (en) * | 2021-10-08 | 2021-12-28 | 河北三棵树涂料有限公司 | Slow-release mildew-proof coating and preparation method thereof |
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2000
- 2000-08-09 JP JP2000275661A patent/JP2002053412A/en active Pending
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| EP1519995B1 (en) * | 2002-06-19 | 2016-02-24 | THOR GmbH | Coating material with biocide microcapsules |
| US7429392B2 (en) | 2002-06-19 | 2008-09-30 | Thor Gmbh | Coating material with biocide microcapsules |
| EP1698672A3 (en) * | 2002-06-19 | 2006-09-20 | THOR GmbH | Coating material with biocide microcapsules |
| EP2201836A3 (en) * | 2004-09-14 | 2013-03-20 | Microtek Laboratories, Inc. | Microencapsulation of biocides and antifouling agents |
| JP2008513475A (en) * | 2004-09-14 | 2008-05-01 | マイクロテック ラボラトリーズ インク | Microcapsule encapsulating biocide and coating composition |
| US7550200B2 (en) | 2004-09-14 | 2009-06-23 | Microtek Laboratories, Inc. | Microencapsulation of biocides and antifouling agents |
| US7938897B2 (en) * | 2004-09-14 | 2011-05-10 | Microtek Laboratories Inc. | Microencapsulation of biocides and antifouling agents |
| NO338168B1 (en) * | 2004-09-14 | 2016-08-01 | Microtek Laboratories Inc | Microencapsulation of biocides and anti-fouling agents |
| CN101137288B (en) * | 2004-09-14 | 2011-09-28 | 微技术实验室公司 | Microencapsulation of biocides and antifouling agents |
| WO2006032019A1 (en) | 2004-09-14 | 2006-03-23 | Microtek Laboratories, Inc. | Microencapsulation of biocides and antifouling agents |
| KR101253065B1 (en) * | 2004-09-14 | 2013-04-11 | 마이크로텍 라보라토리즈, 인코포레이티드 | Microencapsulation of biocides and antifouling agents |
| CN101037554B (en) * | 2006-03-16 | 2013-06-12 | 罗门哈斯公司 | Blends of encapsulated biocides |
| KR100869489B1 (en) | 2006-03-16 | 2008-11-19 | 롬 앤드 하아스 컴패니 | Blends of Encapsulated Biocides |
| US7377968B2 (en) * | 2006-03-16 | 2008-05-27 | Rohm And Haas Company | Blends of encapsulated biocides |
| WO2008000797A3 (en) * | 2006-06-30 | 2009-01-22 | Thor Gmbh | Antimicrobial microparticles |
| DE102006061890A1 (en) | 2006-12-28 | 2008-07-03 | Thor Gmbh | Adhesives and sealants, e.g. for use in building or vehicle construction, containing active biocidal agents, especially 2-n-octyl-4-isothiazolin-3-one, encapsulated in resin-based microparticles |
| EP2801256A1 (en) | 2013-05-08 | 2014-11-12 | LANXESS Deutschland GmbH | Microcapsules containing an algicide and a melamine-formaldehyde polymer |
| US10212935B2 (en) | 2014-02-27 | 2019-02-26 | Lanxess Deutschland Gmbh | Biocidic microcapsules |
| WO2020099567A1 (en) | 2018-11-16 | 2020-05-22 | Lonza Ltd | Encapsulated biocides |
| CN113845793A (en) * | 2021-10-08 | 2021-12-28 | 河北三棵树涂料有限公司 | Slow-release mildew-proof coating and preparation method thereof |
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