JPH073191A - Antifouling agent for coating material - Google Patents
Antifouling agent for coating materialInfo
- Publication number
- JPH073191A JPH073191A JP14898893A JP14898893A JPH073191A JP H073191 A JPH073191 A JP H073191A JP 14898893 A JP14898893 A JP 14898893A JP 14898893 A JP14898893 A JP 14898893A JP H073191 A JPH073191 A JP H073191A
- Authority
- JP
- Japan
- Prior art keywords
- antifouling
- compound
- compd
- isothiazolone
- agent
- 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
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Paints Or Removers (AREA)
Abstract
Description
【0001】[0001]
【産業上の利用分野】本発明は塗料用防汚剤に係り、特
に、船底又は魚網等の各種水中部材用塗料の防汚剤であ
って、有効成分の徐放性により、防汚効果を長期間維持
することができる塗料用防汚剤に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an antifouling agent for paints, and more particularly to an antifouling agent for paints for various underwater components such as ship bottoms and fishnets, which has a sustained release property of the active ingredient to provide an antifouling effect. The present invention relates to an antifouling agent for paint that can be maintained for a long period of time.
【0002】[0002]
【従来の技術】緑藻や褐藻等の植物類、フジツボ、セル
プラ、カサネカンザシ、ホヤ、イガイ、カキ等の動物
類、スライムと称される各種バクテリア、カビ、けい藻
などの水棲生物が船舶の船底部や漁業用網、その他の各
種水中部材に付着すると、当該部材に多大な悪影響をも
たらす。2. Description of the Related Art Plants such as green algae and brown algae, animals such as barnacles, serpra, magpie squirts, squirts, mussels, oysters, and various aquatic organisms such as bacteria called slime, mold and diatoms are the bottoms of ships. If it adheres to fishnets, fishing nets, or other various underwater members, it will have a great adverse effect on the members.
【0003】そこで、これらの部材に防汚剤を含む塗料
を塗布して水棲生物の付着を防止する対策がとられてお
り、従来、塗料用防汚剤としては、ビス−(トリブチル
スズ)オキサイド(TBTO)などの有機スズ化合物が
使用されていた。しかしながら、TBTOは魚類への蓄
積性などの面から規制されつつあることから、TBTO
に替わるものとして、2,4,5,6−テトラクロロイ
ソフタロニトリル,ジンクメチルジチオカーバメートな
どが検討されている。また、イソチアゾロン系化合物も
提案されている。Therefore, measures have been taken to prevent the adhesion of aquatic organisms by applying a paint containing an antifouling agent to these members. Conventionally, as an antifouling agent for paints, bis- (tributyltin) oxide ( Organotin compounds such as TBTO) have been used. However, TBTO is being regulated in terms of its accumulation in fish, etc.
As alternatives to 2,4,5,6-tetrachloroisophthalonitrile, zinc methyldithiocarbamate, etc. have been investigated. Also, isothiazolone compounds have been proposed.
【0004】[0004]
【発明が解決しようとする課題】しかしながら、2,
4,5,6−テトラクロロイソフタロニトリルやジンク
メチルジチオカーバメートは防汚効果が十分ではなく、
実用性に劣る。[Problems to be Solved by the Invention]
The antifouling effect of 4,5,6-tetrachloroisophthalonitrile and zinc methyldithiocarbamate is not sufficient,
Inferior in practicality.
【0005】イソチアゾロン系化合物は、良好な防汚作
用を示すが、水に対する溶解度が高く、塗料用防汚剤と
して使用すると、早期に溶解して効果の持続性が得られ
ないという欠点がある。The isothiazolone compounds have a good antifouling action, but they have a high solubility in water, and when they are used as antifouling agents for paints, they have the drawback that they dissolve early and the effect cannot be sustained.
【0006】この問題を解決するものとして、イソチア
ゾロン系化合物を1,1,6,6−テトラフェニル−
2,4−ヘキサジイン−1,6−ジオール(以下「TP
H」と略称する。)又は1,1−ジ(2,4−ジメチル
フェニル)−2−プロビン−1−オール(以下「DM
P」と略称する。)で包接してなる包接化合物を防汚剤
とする塗料が提案されているが(特開昭62−1150
72号公報)、この包接化合物であっても効果持続時間
が十分に長いとはいえず、より一層の改良が望まれてい
る。As a solution to this problem, an isothiazolone-based compound is added to 1,1,6,6-tetraphenyl-
2,4-hexadiyne-1,6-diol (hereinafter "TP
It is abbreviated as "H". ) Or 1,1-di (2,4-dimethylphenyl) -2-probin-1-ol (hereinafter “DM
It is abbreviated as "P". A coating composition has been proposed in which the clathrate compound obtained by clathration with (1) is used as an antifouling agent (JP-A-62-1150).
No. 72), it cannot be said that the effect duration is sufficiently long even with this clathrate compound, and further improvement is desired.
【0007】本発明は上記従来の問題点を解決し、防汚
効果の持続時間が著しく長く、特に、海洋有害生物の防
除剤として有効な塗料用防汚剤を提供することを目的と
する。It is an object of the present invention to solve the above-mentioned conventional problems and to provide an antifouling agent for paints, which has an extremely long antifouling effect and is particularly effective as a controlling agent for marine pests.
【0008】[0008]
【課題を解決するための手段】本発明の塗料用防汚剤
は、イソチアゾロン系化合物と5,5’−ジクロロ−
2,2’−ジヒドロキシジフェニルメタンとの包接化合
物を含むことを特徴とする。The antifouling agent for paint of the present invention comprises an isothiazolone compound and 5,5'-dichloro-.
It is characterized by containing an inclusion compound with 2,2'-dihydroxydiphenylmethane.
【0009】以下に本発明を詳細に説明する。The present invention will be described in detail below.
【0010】本発明で使用されるイソチアゾロン系化合
物は下記の一般式(I)で表される化合物である。The isothiazolone compound used in the present invention is a compound represented by the following general formula (I).
【0011】[0011]
【化1】 [Chemical 1]
【0012】本発明においては、このようなイソチアゾ
ロン系化合物のうち、特に下記構造式(II)で示される5
−クロロ−2−メチル−4−イソチアゾリン−3−オン
(以下「CMI」と略称する。)を用いるのがその優れ
た抗菌力から好適である。In the present invention, among such isothiazolone compounds, particularly 5 represented by the following structural formula (II):
It is preferable to use -chloro-2-methyl-4-isothiazolin-3-one (hereinafter abbreviated as "CMI") because of its excellent antibacterial activity.
【0013】[0013]
【化2】 [Chemical 2]
【0014】本発明においては、このようなイソチアゾ
ロン系化合物をゲスト化合物として、ホスト化合物であ
る下記構造式(III) で示される5,5’−ジクロロ−
2,2’−ジヒドロキシジフェニルメタン(以下「CH
PM」と略称する。)に包接化して包接化合物としたも
のを有効成分とする。In the present invention, such an isothiazolone compound is used as a guest compound, and 5,5'-dichloro- which is a host compound represented by the following structural formula (III).
2,2'-dihydroxydiphenylmethane (hereinafter "CH
It is abbreviated as "PM". ) Is included as an inclusion compound to be an active ingredient.
【0015】[0015]
【化3】 [Chemical 3]
【0016】本発明に係るこのような包接化合物は、溶
媒中もしくは無溶媒反応にて容易に製造することができ
る。Such an inclusion compound according to the present invention can be easily produced in a solvent or in a solventless reaction.
【0017】溶媒を用いる場合には、メタノール、エタ
ノール、アセトン等の通常の水可溶性溶媒にCHPMを
溶解させた溶液と、CMI等のイソチアゾロン系化合物
あるいはこれに更に不純物等を含む混合物とを混合して
反応させる。これにより、包接化合物が固形物として析
出するので、これを常法により濾過分離して目的とする
包接化合物を得る。When a solvent is used, a solution prepared by dissolving CHPM in an ordinary water-soluble solvent such as methanol, ethanol or acetone is mixed with an isothiazolone compound such as CMI or a mixture containing impurities. To react. As a result, the clathrate compound precipitates as a solid, and the clathrate compound is filtered and separated by a conventional method to obtain the target clathrate compound.
【0018】このような溶媒反応によって、本発明に係
る包接化合物を容易に得ることができるが、本発明にお
いては、無溶媒反応でも製造することができる。The clathrate compound according to the present invention can be easily obtained by such a solvent reaction, but in the present invention, the inclusion compound can also be produced by a solventless reaction.
【0019】この場合には、CHPMを直接ゲスト化合
物であるCMI等のイソチアゾロン系化合物を溶解した
水溶液中に添加して混合、撹拌する。用いる水溶液は、
必ずしもゲスト化合物となるイソチアゾロン系化合物の
みを含むものである必要はなく、前記溶媒反応の場合と
同様、イソチアゾロン系化合物と不純物等を含むもので
あっても良い。即ち、CMI等のイソチアゾロン系化合
物とCHPMとは極めて選択性良く反応するため、本発
明に係る包接化合物の製造にあたって、原料のイソチア
ゾロン系化合物として、副生成物等の不純物を含有する
ものをそのまま用いても、目的とするイソチアゾロン系
化合物のみを選択的に包接した包接化合物が得られる。In this case, CHPM is directly added to an aqueous solution in which an isothiazolone compound such as CMI which is a guest compound is dissolved and mixed and stirred. The aqueous solution used is
It is not always necessary to include only the isothiazolone compound serving as the guest compound, and as in the case of the solvent reaction, it may include the isothiazolone compound and impurities and the like. That is, since an isothiazolone compound such as CMI reacts with CHPM with extremely high selectivity, in the production of the inclusion compound according to the present invention, an isothiazolone compound as a raw material containing impurities such as by-products is used as it is. Even when used, an inclusion compound in which only the desired isothiazolone compound is selectively included is obtained.
【0020】なお、反応温度は0〜100℃の範囲にお
いて任意で良いが、通常の場合10〜30℃程度とす
る。反応時間は0.5〜24時間程度で十分である。The reaction temperature may be any temperature in the range of 0 to 100 ° C, but is usually about 10 to 30 ° C. A reaction time of about 0.5 to 24 hours is sufficient.
【0021】反応終了後、包接化合物は通常固形物とし
て得られるので、これを水層と分離し、水洗、乾燥し
て、目的とする包接化合物を得ることができる。After the completion of the reaction, the clathrate compound is usually obtained as a solid, and this can be separated from the aqueous layer, washed with water and dried to obtain the desired clathrate compound.
【0022】本発明に係る包接化合物は、塗料用防汚剤
として、塗料組成物全体に対して0.5〜50重量%程
度配合して使用するのが好ましい。この塗料組成物中に
は、その他の無機(亜酸化銅など)、有機(TBTO、
ダコニールなど)防汚剤を併用配合しても良い。The clathrate compound according to the present invention is preferably used as an antifouling agent for paints in an amount of about 0.5 to 50% by weight based on the total weight of the paint composition. In this coating composition, other inorganics (such as cuprous oxide), organics (TBTO,
An antifouling agent may be used in combination.
【0023】なお、本発明の塗料用防汚剤を配合する塗
料組成物の塗料ビヒクルとしては、通常使用される樹脂
ビヒクルを使用することができるが、好ましくは非水溶
性樹脂及びロジン系ビヒクルが用いられる。具体的に
は、塩化ビニル系樹脂、塩化ゴム系樹脂、塩素化ポリエ
チレン樹脂、塩素化ポリプロピレン樹脂、アクリル樹
脂、スチレン−ブタジエン系樹脂、ポリエステル系樹
脂、エポキシ系樹脂、石油系樹脂、油系樹脂、ロジンエ
ステル系樹脂、ロジン系石鹸、ロジン等が挙げられる。
また、防汚性を有するビヒクルとして、(メタ)アクリ
ル酸とビス(トリブチルスズ)オキサイド、トリフェニ
ルスズハイドロオキサイドのような有機スズ化合物の縮
合反応で得られる、α,β−不飽和モノもしくはジカル
ボン酸の有機スズ化合物塩を構成単位として含むアクリ
ル共重合体樹脂組成物を使用することもできる。As the paint vehicle of the paint composition containing the antifouling agent for paint of the present invention, a commonly used resin vehicle can be used, but a water-insoluble resin and a rosin-based vehicle are preferred. Used. Specifically, vinyl chloride resin, chlorinated rubber resin, chlorinated polyethylene resin, chlorinated polypropylene resin, acrylic resin, styrene-butadiene resin, polyester resin, epoxy resin, petroleum resin, oil resin, Examples thereof include rosin ester-based resin, rosin-based soap, and rosin.
Further, as a vehicle having an antifouling property, α, β-unsaturated mono- or dicarboxylic acid obtained by a condensation reaction of (meth) acrylic acid and an organic tin compound such as bis (tributyltin) oxide or triphenyltin hydroxide It is also possible to use an acrylic copolymer resin composition containing the organic tin compound salt of 1 as a constituent unit.
【0024】本発明の塗料用防汚剤を配合してなる塗料
組成物は、このような塗料ビヒクルに本発明の塗料用防
汚剤の所定量を配合し、更に必要に応じて、通常の塗料
組成物に使用される可塑剤、着色顔料、有機溶剤等を配
合して、常法に従って混合することにより容易に調製す
ることができる。A coating composition containing the antifouling agent for paints of the present invention is prepared by adding a predetermined amount of the antifouling agent for paints of the present invention to such a coating vehicle, and if necessary, a conventional composition. It can be easily prepared by blending a plasticizer, a coloring pigment, an organic solvent and the like used in the coating composition and mixing them according to a conventional method.
【0025】[0025]
【作用】本発明の塗料用防汚剤では、イソチアゾロン系
化合物がCHPMで包接化合物とされているために、水
中で包接化合物からゲスト分子であるイソチアゾロン系
化合物を水中に徐々に溶出する良好な徐放性を示すこと
から、防汚活性を極めて長時間維持することができる。In the antifouling agent for paints of the present invention, since the isothiazolone compound is the inclusion compound in CHPM, the isothiazolone compound, which is a guest molecule, is gradually eluted from the inclusion compound in water. The antifouling activity can be maintained for an extremely long period of time because it exhibits excellent sustained release properties.
【0026】理由の詳細は不明であるが、本発明の塗料
用防汚剤は、とりわけ海水中において、従来の包接化合
物による塗料用防汚剤に比べて徐放期間が顕著に長く、
船底用防汚塗料、魚網用防汚剤等の塗料用防汚剤として
スライムの防除に極めて有効である。Although the details of the reason are not clear, the antifouling agent for paints of the present invention has a markedly longer sustained release period than the conventional antifouling agents for paints using clathrate compounds, especially in seawater.
It is extremely effective in controlling slime as an antifouling agent for paints such as antifouling paints for ship bottoms and fishnets.
【0027】[0027]
【実施例】以下に製造例、実験例、実施例及び比較例を
挙げて更に具体的に説明するが、本発明はその要旨を超
えない限り以下の実施例に限定されるものではない。EXAMPLES The present invention will be more specifically described below with reference to production examples, experimental examples, examples and comparative examples, but the present invention is not limited to the following examples unless it exceeds the gist.
【0028】製造例1:CMIとCHPMとの包接化合
物の製造 CHPM0.2gとCMIを主成分として含む水溶性殺
菌剤水溶液1.5g(殺菌剤濃度10.4重量%)を混
合し、室温で撹拌しながら4時間反応させた。得られた
半固形物を水層と分離して乾燥した。Production Example 1: Production of inclusion compound of CMI and CHPM: 0.2 g of CHPM and 1.5 g of a water-soluble aqueous bactericide solution containing CMI as a main component (bactericide concentration 10.4% by weight) are mixed, and the mixture is allowed to stand at room temperature. The reaction was carried out for 4 hours with stirring. The resulting semi-solid was separated from the aqueous layer and dried.
【0029】生成物のNMRスペクトルの積分値より、
このものはCHPM:CMI=1:0.35(モル比)
の包接化合物であることが確認された。この包接化合物
を「CHPM−CMI包接化合物」と称す。From the integrated value of the NMR spectrum of the product,
This is CHPM: CMI = 1: 0.35 (molar ratio)
It was confirmed that the inclusion compound was This clathrate compound is referred to as "CHPM-CMI clathrate compound".
【0030】製造例2:CMIとTPHとの包接化合物
の製造 TPH0.5gをメタノール10mlに溶解したTPH
溶液に、CMIを主成分とする水溶性殺菌剤4.26g
(CMI含有量326mg)を添加して撹拌したとこ
ろ、白濁物が析出した。これを室温で3時間静置した
後、濾紙で濾過して析出物と溶液とを分離した。Production Example 2: Production of inclusion compound of CMI and TPH TPH prepared by dissolving 0.5 g of TPH in 10 ml of methanol
4.26 g of a water-soluble fungicide containing CMI as a main component in the solution
When (CMI content 326 mg) was added and stirred, a white turbid matter was deposited. This was allowed to stand at room temperature for 3 hours and then filtered through filter paper to separate the precipitate from the solution.
【0031】析出物のNMR分析の結果、この析出物は
TPH:CHI=1:2(モル比)の包接化合物である
ことが確認された。この包接化合物を「TPH−CMI
包接化合物」と称す。As a result of NMR analysis of the precipitate, it was confirmed that the precipitate was an inclusion compound of TPH: CHI = 1: 2 (molar ratio). This clathrate compound was labeled as "TPH-CMI.
It is referred to as "inclusion compound".
【0032】製造例3:CMIとDMPとの包接化合物
の製造 DMP0.5gメタノール10mlに溶解したDMP溶
液に、CMIを主成分とする水溶性殺菌剤3.32g
(CMI含有量283mg)を添加して撹拌したとこ
ろ、白濁物が析出した。この析出物を製造例2と同様に
して分離し、分析を行なったところ、この析出物はDM
P:CMI=2:1(モル比)の包接化合物であること
が確認された。この包接化合物を「DMP−CMI包接
化合物」と称す。Production Example 3: Production of inclusion compound of CMI and DMP DMP 0.5 g Water-soluble bactericide containing CMI as a main component 3.32 g in a DMP solution dissolved in 10 ml of methanol.
When (CMI content 283 mg) was added and stirred, a white turbid matter was deposited. When this precipitate was separated and analyzed in the same manner as in Production Example 2, the precipitate was found to be DM.
It was confirmed to be an inclusion compound with P: CMI = 2: 1 (molar ratio). This clathrate compound is referred to as "DMP-CMI clathrate compound".
【0033】実験例1 CHPM−CMI包接化合物を10gとり、0.8μメ
ンブレンフィルター袋に入れ、これを純水1リットル中
に浸漬し、スタラー撹拌しながら包接化合物からの有効
成分(CMI)の放出率を経時測定し、CMI単独の場
合と比較した結果を表1に示した。表1より、CMI単
独では直ちに全量が溶出するのに対し、CHPM−CM
I包接化合物ではCMIは徐々に溶出し、徐放性を示す
ことが明らかである。Experimental Example 1 10 g of the CHPM-CMI clathrate compound was placed in a 0.8 μ membrane filter bag, immersed in 1 liter of pure water, and the active ingredient (CMI) from the clathrate compound was stirred while stirring with a stirrer. The release rate was measured over time, and the results of comparison with the case of CMI alone are shown in Table 1. From Table 1, CMI alone elutes the entire amount immediately, whereas CHPM-CM
It is clear that in the inclusion compound I, CMI gradually elutes and exhibits sustained release.
【0034】[0034]
【表1】 [Table 1]
【0035】実施例1〜5,比較例1〜7 表2に示す配合にて、各成分をボールミルに仕込み、2
4時間分散を行ない、塗料組成物を調製した。Examples 1 to 5 and Comparative Examples 1 to 7 The ingredients shown in Table 2 were charged in a ball mill, and 2
Dispersion was carried out for 4 hours to prepare a coating composition.
【0036】なお、表2において、*1〜*5は次の通
りである。 *1 ラロフレックスMP−45:独国BASF社製塩
化ビニル−ビニルイソプロピルエーテル共重合体 *2 ブライオライトS−5B:米国グッドイヤー社製
スチレン−ブタジエン共重合体 *3 VACH:米国UCC社製ポリ塩化ビニル樹脂 *4 TBTアクリルコポリマー溶液:次のようにして
製造した。即ち、トリブチルスズメタクリレート65重
量部とメチルメタクリレート35重量部の混合物40重
量部を、加熱、冷却できる手段を備えた反応槽中のキシ
レン60重量部に溶解し、これに0.35重量部の過酸
化ベンゾイルを加えた。発熱による温度上昇を調節する
ため、冷却手段を用いて溶液の温度を10時間にわたっ
て最終温度110℃まで還流下に徐々に上昇させた。最
終的な溶液粘度は25℃において4.5ポイズになっ
た。In Table 2, * 1 to * 5 are as follows. * 1 Laroflex MP-45: Vinyl chloride-vinyl isopropyl ether copolymer manufactured by BASF, Germany * 2 Bryolite S-5B: Styrene-butadiene copolymer manufactured by Goodyear, USA * 3 VACH: Polychlorinated by UCC, USA Vinyl resin * 4 TBT acrylic copolymer solution: Produced as follows. That is, 40 parts by weight of a mixture of 65 parts by weight of tributyltin methacrylate and 35 parts by weight of methyl methacrylate was dissolved in 60 parts by weight of xylene in a reaction vessel equipped with a means capable of heating and cooling, and 0.35 parts by weight of peroxide was added thereto. Benzoyl was added. In order to control the temperature rise due to the exotherm, the temperature of the solution was gradually raised under reflux to a final temperature of 110 ° C. over 10 hours using cooling means. The final solution viscosity was 4.5 poise at 25 ° C.
【0037】*5 ZDMC:ビス−(ジメチルジチオ
カルバミン酸)亜鉛* 5 ZDMC: Bis- (dimethyldithiocarbamate) zinc
【0038】[0038]
【表2】 [Table 2]
【0039】得られた各塗料組成物について防汚試験を
行なった。防汚試験は各塗料組成物を予め防食塗装(コ
ールタール/塩化ビニル系樹脂をベースとした市販の船
底1号塗料)を施した100×300mmの大きさの試
験用鋼板に乾燥膜厚が60〜80ミクロンになるように
2回塗りし、4時間乾燥後、試験用いかだで海中1mの
深さに浸漬し、フジツボ、セルプラ等の動物及びアオ
サ、アオノリ等の植物の付着量を付着面積%として肉眼
観察により調べ、評価した。An antifouling test was conducted on each of the obtained coating compositions. The antifouling test was carried out by coating each coating composition with anticorrosion coating (commercial ship bottom No. 1 paint based on coal tar / vinyl chloride resin) having a dry film thickness of 60 on a 100 × 300 mm test steel plate. Approximately 80 μm, apply twice, dry for 4 hours, dip to a depth of 1 m in the sea with a test bar, and attach the amount of animals such as barnacles, cerpra and plants such as Ulva and Aonori to the area Was examined and evaluated by visual observation.
【0040】生物付着量の変化を表3に、スライム付着
量の変化を表4にそれぞれ示す。なおスライムとは、種
々の水中バクテリア類とバクテリア類の代謝産物の粘性
膜、ケイソウ類の総称であり、これが付着するとアオ
サ、アオノリの胞子、或いはフジツボの幼生が入り、汚
染生物の繁殖を助長するから、防汚塗料は耐スライム性
に優れていなければならない。Table 3 shows the changes in the amount of attached organisms, and Table 4 shows the changes in the amount of attached slime. Slime is a generic term for viscous membranes of various underwater bacteria and metabolites of bacteria, diatoms, and when they adhere, they will enter the spores of sea lettuce, Aonomori, or barnacle larvae and promote the propagation of contaminated organisms. Therefore, the antifouling paint must have excellent slime resistance.
【0041】[0041]
【表3】 [Table 3]
【0042】[0042]
【表4】 [Table 4]
【0043】表3,4より明らかなように、本発明の塗
料用防汚剤は比較例と比べて著しく良好な結果を示して
いる。とりわけスライム付着防止に関しては、著しく優
れた効果を発揮している。As is clear from Tables 3 and 4, the antifouling agent for paint of the present invention shows remarkably good results as compared with Comparative Examples. In particular, it is extremely effective in preventing slime adhesion.
【0044】[0044]
【発明の効果】以上詳述した通り、本発明の塗料用防汚
剤は、あらゆる水棲付着生物に対して良好な防汚効果を
示すと共に、その防汚活性の長期持続性に優れ、特に海
中でのスライムに対する防汚効果が著しく高く、工業的
に極めて有用である。As described in detail above, the antifouling agent for paints of the present invention exhibits a good antifouling effect against all aquatic adherent organisms and is excellent in long-term sustainability of its antifouling activity, especially in the sea. It has a very high antifouling effect against slime and is industrially extremely useful.
【0045】また、有効成分であるイソチアゾロン系化
合物はその皮膚刺激性から、取り扱い上、注意が必要で
あったが、包接化により、作業環境が改善され、安全性
が向上される。The isothiazolone compound, which is an active ingredient, requires caution in handling due to its skin irritation. However, the inclusion environment improves the working environment and enhances the safety.
【0046】しかも、本発明に係る包接化合物は、塗料
化に当たって塗料の増粘、変質等の塗料の貯蔵安定性に
悪影響がなく、安全性が高いので作業性が向上し、環境
汚染も少ない。更に、本発明の塗料用防汚剤を用いた防
汚塗料は材料に対する腐食性がないため、特に鋼鉄、軽
合金、コンクリート製の船舶や水中構造物に悪影響を及
ぼすことなく有効に使用することができる。Moreover, the clathrate compound according to the present invention has no adverse effect on the storage stability of the paint, such as viscosity increase and deterioration of the paint when it is made into a paint, and has high safety, thus improving workability and less environmental pollution. . Furthermore, since the antifouling paint using the antifouling agent for paints of the present invention is not corrosive to materials, it can be effectively used particularly without adversely affecting steel, light alloy, concrete vessels and underwater structures. You can
Claims (1)
クロロ−2,2’−ジヒドロキシジフェニルメタンとの
包接化合物を含むことを特徴とする塗料用防汚剤。1. An antifouling agent for paints, which comprises an inclusion compound of an isothiazolone compound and 5,5′-dichloro-2,2′-dihydroxydiphenylmethane.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP14898893A JPH073191A (en) | 1993-06-21 | 1993-06-21 | Antifouling agent for coating material |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP14898893A JPH073191A (en) | 1993-06-21 | 1993-06-21 | Antifouling agent for coating material |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH073191A true JPH073191A (en) | 1995-01-06 |
Family
ID=15465195
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP14898893A Pending JPH073191A (en) | 1993-06-21 | 1993-06-21 | Antifouling agent for coating material |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH073191A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6221374B1 (en) | 1997-05-28 | 2001-04-24 | Rohm And Haas Company | Controlled release compositions |
JP2018167654A (en) * | 2017-03-29 | 2018-11-01 | 国立研究開発法人 海上・港湾・航空技術研究所 | Antifouling performance evaluation method by quantitative analysis of attached matters, and antifouling performance evaluation system |
-
1993
- 1993-06-21 JP JP14898893A patent/JPH073191A/en active Pending
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6221374B1 (en) | 1997-05-28 | 2001-04-24 | Rohm And Haas Company | Controlled release compositions |
JP2018167654A (en) * | 2017-03-29 | 2018-11-01 | 国立研究開発法人 海上・港湾・航空技術研究所 | Antifouling performance evaluation method by quantitative analysis of attached matters, and antifouling performance evaluation system |
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