TWI394532B - 含吡啶硫酮及吡咯衍生物之殺生物劑組合物 - Google Patents
含吡啶硫酮及吡咯衍生物之殺生物劑組合物 Download PDFInfo
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Description
本發明係關於一種殺生物組合物。更特定言之,本發明係關於一種防止或抑制微生物生長之包含至少一種經選擇吡啶硫酮化合物及至少一種經選擇吡咯衍生物之摻和物的殺生物組合物及使用該殺生物組合物之方法。
在該項技術中已知用於防止、抑制及處理微生物生長或侵染之許多組合物及調配物。同樣,存在許多特定經調配用於防止、抑制及處理附著生物(fouling organism)之生長或侵染之組合物及塗料。
附著生物給暴露於水中之基材及物件帶來巨大問題。術語"附著生物”包括硬附著生物及軟附著生物兩者。硬附著生物包括藤壺、軟體動物及其類似物,而軟附著生物包括藻類、真菌及在以引用的方式併入本文中之美國專利第5,712,275號中列出之生物。該等生物給暴露於海水、淡水、半鹹水、污水、廢水、雨水及其類似物中之物件及基材帶來屢見的問題。
附著生物生長於暴露於任何類型水中之各種基材及物件上,侵染該等基材及物件,或黏附於其上。附著生物在表面上生長或侵染在視覺上無吸引力。另外,在使用附著生物已附著或侵染之基材及物件方面,生長可能引起一些問題。舉例而言,經常發生之一個問題為硬附著生物附著於船體上。該等生物使得船表面變得粗糙,由此降低船之速度。
另外,木材及木材製品經常經歷諸如附著生物、白蟻及其類似物之微生物之生長及侵染。該等微生物之生長及侵染導致木材及木材製品之翹曲、破裂及損壞。因此,木材及木材製品失去價值、視覺吸引力及有用性。
為防止此問題,已開發包含殺生物劑之塗料。已發現適用之殺生物劑之實例包括三丁基錫化合物、吡啶硫酮化合物、噁噻嗪(oxathiazine)化合物、吡咯化合物、三苯基硼化合物及terbutyn。
吡啶硫酮化合物及選擇吡咯化合物分別已知且係用作殺生物劑或防污劑(antifouling agent)。然而,其在該項技術中尚不清楚,組合兩種化合物亦不明顯。教示吡啶硫酮化合物及選擇吡咯化合物之用途之先前技術參考文獻之實例包括以下:Ruggiero之美國專利第5,057,153號係關於一種特徵為增強殺生物功效之改良油漆或底漆組合物。該油漆含有包含吡啶硫酮鹽及銅鹽之殺生物劑。另外,在Farmer Jr.等人之美國專利第5,246,489號中揭示一種用於在油漆調配物中就地產生吡啶硫酮銅殺生物劑之方法。此專利之油漆及底漆包含作為存在於調配物中之僅有殺生物劑之吡啶硫酮化合物。
Hani等人之美國專利第5,098,473號係關於油漆及底漆,且更特定言之係關於一種用於提供吡啶硫酮鋅加上氧化亞銅殺生物劑於油漆中之穩定無凝膠分散液之方法(亦參見美國專利第5,098,473號;第5,112,397號;第5,137,569號;第5,185,033號;第5,232,493號;第5,298,061號;第5,342,437號;PCT專利申請案第WO 95/10568號及第EP 0610251號)。
French等人之美國專利第4,957,658號係關於油漆及底漆,且更特定言之係關於一種用於提供降低變色之含有吡啶硫酮及鐵離子之油漆及底漆之方法及組合物。
Davidson等人之美國專利第4,399,130號描述一種使用有效量之吡啶-2-硫酮-N-氧化物之至少一種金屬鹽以處理或防止豬滲出性表皮炎(swine exudate epidermitis)之方法。
Henderson等人之美國專利第4,496,559號描述用作殺真菌劑及殺菌劑之2-硒吡啶-N-氧化物之經選擇衍生物。
Trotz等人之美國專利第4,565,856號係關於含有吡啶硫酮之聚合物。在此專利中描述之聚合物係用作油漆及木材防腐劑製品中之殺生物劑。
Wedy等人之美國專利第4,610,993號描述一種投與有效量之至少一種經選擇吡啶-N-氧化物二硫化物化合物以處理或防止牛乳腺炎之方法。
歐洲專利第EP 0746979號描述一種用於藉由使生物與防污有效量之2-芳基吡咯化合物接觸來控制或防止附著生物附著於水下表面之方法。
Kramer等人之美國專利第6,069,189號描述含有經選擇吡咯衍生物之防污油漆。併入防污油漆中之特定吡咯化合物包括2-三鹵甲基-3-鹵-4-氰基吡咯及其衍生物。Kramer等人發現此等化合物尤其有效抵抗藤壺侵染。另外,Kramer等人之此參考文獻發現儘管添加此等化合物,但可產生明亮或淡色防污油漆。
PCT專利申請案第WO 03/039256號描述一種防污組合物,其包含以該組合物之乾物質總重量計至少3.5重量%之量的4-溴-2-(4-氯苯基)-5-(三氟甲基)-1H-吡咯-3-甲腈或其鹽以及另一種殺生物劑。另一種殺生物劑係選自bethoxazin、甲苯氟磺胺(tolylfluanide)、二氯氟磺胺(dichlofuanide)或DCOIT。
儘管在該項技術中取得進步,但仍需要包含可能將有效抵抗大範圍微生物,亦及證明高耐久性及低毒性之殺生物組合物之塗料。理想地,將容易且經濟地製造該塗料及該組合物。咸信本發明為以上討論問題之答案。
因此,本發明之一態樣係針對一種包含一或多種吡啶硫酮化合物及一或多種式I之吡咯化合物之殺生物組合物:
其中X為鹵素、CN、NO2
或S(O)n
R1
;Y為氫、鹵素或S(O)n
R1
;Z為鹵素、C1
-C4
鹵烷基或S(O)n
R1
;n為0、1或2之整數;R1
為C1
-C4
鹵烷基;L為氫或鹵素;M及Q各自獨立地為氫、鹵素、C1
-C4
烷基、C1
-C4
鹵烷基、C1
-C4
烷氧基、C1
-C4
烷硫基、C1
-C4
烷基亞磺醯基、C1
-C4
烷基磺醯基、CN、NO2
、R2
CO或NR3
R4
,或當M及Q位於相鄰位置上且與其所連接之碳原子連在一起時,MQ表示結構OCH2
O-、-OCF2
O-或-CH=CH-CH=CH-;R為氫、C1
-C4
烷氧基烷基、C1
-C4
烷基硫烷基或R6
CO;R2
為C1
-C4
烷基、C1
-C4
鹵烷基、C1
-C4
烷氧基或NR3
R4
;R3
為氫或C1
-C4
烷基;R4
為氫、C1
-C4
烷基或R5
CO;R5
為氫或C1
-C4
烷基;且R6
為C1
-C4
烷基、C1
-C4
鹵烷基、C1
-C4
烷氧基、C2
-C6
烯基氧基、C1
-C4
鹵烷氧基、視情況經一至三個C1
-C4
烷基取代之苯基、苯甲基、苯氧基、苯甲氧基、C1
-C4
烷基羰基氧基、C3
-C6
環烷基、萘基、吡啶基、噻吩基或呋喃基,其中該殺生物組合物不含銅或具低銅含量。
如本文所定義,術語鹵素表示Cl、Br、I或F,且術語鹵烷基表示具有1個鹵素原子至2n+1個鹵素原子之任何烷基Cn
H2n+1
,其中該等鹵素原子相同或不同。
本發明之另一態樣係針對一種包含有效殺生物量之包含一或多種吡啶硫酮化合物及如上所述一或多種式(I)之吡咯化合物之殺生物組合物的塗料組合物,其中該殺生物組合物不含銅或具低銅含量。
本發明之另一態樣係針對一種塗覆一基材之方法,該方法包含將含有包含一或多種吡啶硫酮化合物及如上所述一或多種式(I)之吡咯化合物之殺生物組合物的塗料組合物塗覆於該基材上且使該基材上之塗料組合物乾燥。
本發明之又一態樣係針對一種包含含有本發明之殺生物組合物之塗料組合物及基材的經塗覆基材,其中該基材係選自由木材、塑膠、皮革、乙烯樹脂及金屬組成之群。
本發明之一個預期優勢包括提高抵抗大範圍微生物之保護。本發明之另一預期優勢包括木材及木材製品之防腐。另外,預期本發明將耐久、具有低毒性且製造容易並經濟。
如本說明書及申請專利範圍中所用之術語"有效殺生物量"係指對降低、消除或防止微生物附著或生長於基材上具有正效應之殺生物組合物之量。
如本說明書及申請專利範圍中所用之術語"微生物"包括藻類、真菌、生物膜、昆蟲、附著生物(包括硬附著生物及軟附著生物),或可能附著於、生長於諸如木材、混凝土、紙、塑膠及其類似物之材料上或損壞該等材料。
如本說明書及申請專利範圍中所用之術語"不含銅或低銅含量"意謂該等組合物不含有銅或含有以調配物之總重量計總重量百分比小於3重量%之銅。
如本說明書及申請專利範圍中所用之術語"木材製品"包括含有或源於包括(但不限於)粒子板、碎木片板、膠合板、晶圓板(wafer board)、木材層壓材料、壓製木材及其類似物之木材的材料。
如上所指示,本發明之一態樣為一種包含一或多種吡啶硫酮化合物及如上所述一或多種根據式(I)之吡咯化合物之殺生物組合物。以下更詳細討論此等組份之每一者。
吡啶硫酮通常普遍已知且經常用於包括油漆及個人護理產品之各種應用中。吡啶硫酮為優良殺生物劑且可見於防污船用油漆中。另外,包括錫、鎘及鋯之吡啶硫酮之金屬鹽適用於洗髮精中。
較佳地,殺生物組合物中之吡啶硫酮為具有以下基本結構之化合物:
適用於本發明之吡啶硫酮化合物包括吡啶硫酮鋅、吡啶硫酮銅、奧麥丁鈉(sodium Omadine)、吡啶-N-氧化物二硫化物、奧麥丁二硫化物(Omadinedisulfide)、2,2'-二硫-吡啶-1,1-二氧化物或吡啶-2-硫酮-N-氧化物。該等吡啶硫酮化合物具有優良殺生物效應。吡啶硫酮鋅及吡啶硫酮銅由於在鹽水中之低可溶性而最佳,因此使得其吡其他吡啶硫酮鹽更耐用。
吡啶硫酮鋅及吡啶硫酮銅化合物可由Berstein等人之美國專利第2,809,971號中描述之方法製備。揭示用於製造其之類似化合物及方法之其他專利包括美國專利第2,786,847號;第3,589,999號;及第3,773,770號。
另外,本發明之殺生物組合物包含如上所示之一或多種式(I)之吡咯化合物。較佳地,吡咯化合物為在5位及視情況在1位處經取代之2-三鹵甲基-3-鹵-4-氰基吡咯衍生物,在2位及3位處之鹵素係獨立地選自由氟、氯及溴組成之群,在5位處之取代基係選自由下列基團組成之群:C1-8烷基、C1-8單鹵烷基、C5-6環烷基、C5-6單鹵環烷基、苯甲基、苯基、單鹵苯甲基及二鹵苯甲基、單鹵苯基及二鹵苯基、單C1-4烷基苯甲基及二C1-4烷基苯甲基、單C1-4烷基苯基及二C1-4烷基苯基、單鹵單C1-4烷基苯甲基及單鹵單C1-4烷基苯基,在5位處之取代基上之任何鹵素係選自由氯及溴組成之群,在1位處之可選取代基係選自C1-4烷基及C1-4烷氧基C1-4烷基。在2-芳基吡咯化合物中,適用於本發明之方法及組合物的為:4,5-二氯-2-(α,α,α-三氟-對甲苯基)吡咯-3-甲腈;4-溴-5-氯-2-(對氯苯基)吡咯-3-甲腈;4-溴-2-(對氯苯基)-5-(三氟甲基)吡咯-3-甲腈;3,4-二氯-2-(3,4-二氯苯基)吡咯-5-甲腈;4-氯-2-(對氯苯基)-5-(三氟甲基)吡咯-3-甲腈;4,5-二溴-2-(對氯苯基)-3-(三氟甲基磺醯基)吡咯;4-溴-2-(3,5-二氯苯基)-5-(三氟甲基)吡咯-3-甲腈;2-(對氯苯基)-5-(三氟甲基)-4-(三氟甲基硫基)吡咯-3-甲腈;4-溴-2-(2,3,4-三氯苯基)-5-(三氟甲基)吡咯-3-甲腈;4-溴-2-(2,3,5-三氯苯基)-5-(三氟甲基)吡咯-3-甲腈;4-溴-2-(對氯苯基)-5-(α,α,β,β-四氟乙硫基)吡咯-3-甲腈;4-溴-2-(間氟苯基)-5-(三氟甲基)吡咯-3-甲腈;2-(3,5-二氯苯基)-5-(三氟甲基)-4-(三氟甲基硫基)吡咯-3-甲腈;及4-溴-2-(對氯苯基)-5-[(β-溴-β,α,α-三氟)-乙硫基]吡咯-3-甲腈。最佳地,式(I)為4-溴-2-(4-氯苯基)-5-(三氟甲基)-1H-吡咯-3-甲腈。
如上所討論之式(I)化合物可由美國專利第5,310,938號及第5,328,928號中描述之方法製備。
為確保殺生物有效性,吡啶硫酮化合物及式(I)化合物較佳以9:1至1:9之重量比存在於殺生物組合物中。更佳地,吡啶硫酮化合物及式(I)化合物係以3:2至2:3之重量比存在於殺生物組合物中。最佳地,吡啶硫酮化合物及式(I)化合物係以3:1至1:3之重量比存在於殺生物組合物中。
本發明之另一態樣包含一種含有以上殺生物組合物之塗料組合物。殺生物組合物係以有效殺生物量存在於該塗料組合物中。有效殺生物量係以塗料組合物之總重量計介於1重量%-15重量%之間。較佳地,殺生物組合物係以塗料組合物之總重量計以介於1重量%與15重量%之間的量存在。更佳地,殺生物組合物係以塗料組合物之總重量計以介於1重量%與10重量%之間的量存在。最佳地,殺生物組合物係以塗料組合物之總重量計以介於3重量%與8重量%之間的量存在。
除殺生物組合物外,塗料組合物亦可包括添加劑。該等添加劑可包括(但不限於)有機結合劑;加工添加劑;固定劑,諸如聚乙烯醇;增塑劑;UV穩定劑;染料;色素;防沉劑;消泡劑;其他殺昆蟲劑,諸如氯化烴、有機磷酸酯及其類似物;其他殺真菌劑及殺菌劑,諸如醇、醛、甲醛釋放化合物及其類似物;酚;有機酸,諸如丙酸、苯甲酸及其類似物;無機酸,諸如硼酸;醯胺;唑;雜環化合物;N-鹵烷硫基化合物;及其類似添加劑。亦可使用用於例如船用防污塗料中之自拋光型的聚合物,諸如丙烯酸系聚合物或丙烯酸系共聚物。較佳地,此等聚合物不含錫。可補充於本發明之組合物中之丙烯酸系聚合物及共聚物之實例包括丙烯酸銅聚合物或共聚物、丙烯酸鋅聚合物或共聚物、丙烯酸矽烷酯聚合物或共聚物及其類似物。在油漆及塗料技術中已知之其他聚合物亦可用於本發明之組合物中。存在於塗料組合物中之添加劑將視使用者或製造者之偏愛以及塗料組合物之最終用途而定。
藉由將殺生物組合物及添加劑組合於諸如船用底漆之底漆材料中而形成塗料組合物。該項技術中係熟知形成該塗料組合物之方法。該等方法之實例包括(但不限於)在摻合機構中組合殺生物組合物及添加劑。該摻合機構將使殺生物組合物均勻分散於整個添加劑中。如熟習該項技術者已知,可使用形成塗料組合物之其他方法。另外,適於船舶應用之包括水或溶劑基調配物之任何底漆材料可用於本發明之塗料組合物中。如例如美國專利第6,710,117號;第4,981,946號;第4,426,464號;第4,407,997號;及第4,021,392號中所示,在該項技術中係已知該等船用油漆。
塗料組合物可採取各種形式。彼等形式包括(但不限於)油漆(尤其防污油漆)、清漆、漆、洗滌劑、木材密封劑或可用以塗覆材料之任何形式。
本發明之另一態樣包含一種包含將以上所描述之塗料組合物塗覆於設法保護之材料的方法。塗料組合物可以各種方式塗覆,該等方式包括(但不限於)刷塗、噴塗、水拭、噴霧在材料上或將材料浸漬、浸沒或浸泡於其中。較佳地,將塗料組合物以均勻方式塗覆於材料上。將塗料組合物塗覆於材料上後,應使其乾燥以確保適當黏著於材料上。可藉由暴露於空氣中或藉由使用使其更快乾燥之機構,諸如加熱燈或熱空氣產生器達成乾燥。
可由塗料組合物保護之材料包括可暴露於微生物或含有該等微生物之水中之木材、皮革、乙烯樹脂、塑膠、混凝土、石膏、紙及任何其他材料。理想地,該材料應具有足以使得塗料組合物滲透且黏附於材料上之多孔性。
本發明之另一態樣包含一種經塗覆基材。該經塗覆基材包含已塗覆有塗料組合物之如上所述的材料。將自塗料組合物之塗覆受益最多之基材包括諸如船體之傳統船舶基材、船塢、橋墩、浮標、漁具、魚網、龍蝦籠、橋及橋樁。然而,塗覆有塗料組合物之基材亦可包括與水或微生物不斷或頻繁接觸之混凝土、壁板、甲板、板壁或任何其他基材。
當基材塗覆有塗料組合物時,預期該基材展現殺生物性質。殺生物性質將防止、抑制或處理微生物在基材上或基材內之附著或生長。防止或處理該等生長將使得該基材無微生物。除基材在視覺上具有吸引力外,無微生物將使其以意欲使用其之方式使用。
另外,預期塗覆有塗料組合物之木材或木材製品將展現抗微生物性。預期將塗料組合物塗覆於木材及木材製品上防止諸如真菌、藻類、白蟻及其類似物之微生物毀壞視覺吸引力及木材及木材製品之用途。將受益於該塗覆之商業及住宅產品及結構包括樓梯、地板、櫥櫃、甲板、橋墩、蓋頂板、橋樁、柵欄、傢具、信箱及其類似物。
以下實例進一步說明本發明。除非另有明確說明,否則所有份數及百分比係以重量計。除非另有明確說明,否則所有溫度為攝氏度。
由Beaufort之杜克大學(Duke University)於2004年在North Carolina海濱測試一系列含有4-溴-2-(4-氯苯基)-5-(三氟甲基)-1H
-吡咯-3-甲腈(在下表中稱為吡咯)及吡啶硫酮鋅(ZPT)之九種油漆其抵抗藤壺及其他附著生物之防污有效性。在實驗室中藉由將各種量之殺生物劑添加至樹脂基調配物(具有氧化鋅填充劑之乙烯樹脂/木松香)中來製造調配物。調配物包括單獨及與ZPT組合之4-溴-2-(4-氯苯基)-5-(三氟甲基)-1H
-吡咯-3-甲腈。將溶劑基氧化鋅塗料用作對照。將未塗底漆之玻璃纖維棒(直徑8 mm×長度11 cm)用每一種調配物浸漬塗覆(5棒/調配物)且自測試架懸掛於海洋中(表面以下一米)。每月評估棒之藤壺及苔蘚蟲數。最滿意之結果來自其中4-溴-2-(4-氯苯基)-5-(三氟甲基)-1H
-吡咯-3-甲腈與ZPT摻合之調配物(參見下表1)。
苔蘚蟲為由個別"個蟲"(所有經活組織連接)構成之高度複合群體動物。個蟲在鈣化殼質組織之杯形或盒形外骨骼內受保護。鈣化程度控制總體結構之剛性或可撓性。苔蘚蟲由諸如海膽及各種軟體動物之各種食草動物食用。
該研究證實4-溴-2-(4-氯苯基)-5-(三氟甲基)-1H
-吡咯-3-甲腈為用於諸如藤壺之硬附著生物之有效防污劑,其與ZPT相容,且其與ZPT作為共殺生物劑比其單獨表現好。
儘管本發明已參考其特定實施例在上文進行描述,但顯然可在不脫離本文中所揭示之本發明概念之情況下進行許多變化、修改及更改。因此,本發明意欲包括屬於附加申請專利範圍之精神及寬範疇中之所有該等變化、修改及更改。
Claims (16)
- 一種殺生物組合物,其包含:A.)吡啶硫酮鋅,及B.)4-溴-2-(4-氯苯基)-5-(三氟甲基)-1H-吡咯-3-甲腈,其中該吡啶硫酮鋅及該4-溴-2-(4-氯苯基)-5-(三氟甲基)-1H-吡咯-3-甲腈係以3:2至2:3之重量比存在;且其中該殺生物組合物係大體上不含銅。
- 如請求項1之殺生物組合物,其進一步包含至少一種選自由丙烯酸銅聚合物或共聚物、丙烯酸鋅聚合物或共聚物、丙烯酸矽烷酯聚合物或共聚物及其組合組成之群的丙烯酸系聚合物或共聚物。
- 一種包含有效殺生物量之殺生物組合物之塗料組合物,其包含:A)吡啶硫酮鋅;及B)4-溴-2-(4-氯苯基)-5-(三氟甲基)-1H-吡咯-3-甲腈,其中該吡啶硫酮鋅及該4-溴-2-(4-氯苯基)-5-(三氟甲基)-1H-吡咯-3-甲腈係以3:2至2:3之重量比存在;且其中該殺生物組合物係大體上不含銅。
- 如請求項3之塗料組合物,其中該有效殺生物量係以該塗料組合物之總重量計介於1重量%與15重量%之間。
- 如請求項4之塗料組合物,其中該有效殺生物量係以該塗料組合物之總重量計介於2重量%與10重量%之間。
- 如請求項5之塗料組合物,其中該有效殺生物量係以該塗料組合物之總重量計介於3重量%與8重量%之間。
- 如請求項3之塗料組合物,其中該塗料組合物為油漆。
- 如請求項3之塗料組合物,其中該塗料組合物為清漆。
- 如請求項3之塗料組合物,其中該塗料組合物為漆。
- 如請求項3之塗料組合物,其中該塗料組合物為木材密封劑。
- 如請求項3之塗料組合物,其進一步包含至少一種選自由丙烯酸銅聚合物或共聚物、丙烯酸鋅聚合物或共聚物、丙烯酸矽烷酯聚合物或共聚物及其組合組成之群的丙烯酸系聚合物或共聚物。
- 一種塗覆一基材之方法,其包含:將該如請求項3之塗料組合物塗覆於該基材上;及使該基材上之該塗料組合物乾燥。
- 如請求項12之方法,其中該基材係選自由木材、塑膠、皮革、乙烯樹脂及金屬組成之群。
- 如請求項12之方法,其中該基材係暴露於水中。
- 一種經塗覆基材,其包含:如請求項3之該塗料組合物;及一基材,其中該基材係選自由木材、塑膠、皮革、乙烯樹脂及金屬組成之群。
- 一種塗料組合物,其包含:殺生物組合物,其包含以該塗料組合物之總重量計約2重量%至約4重量%之吡啶硫酮鋅化合物,及以該塗料組合物之總重量計約2重量%至約5重量%之4-溴-2-(4-氯 苯基)-5-(三氟甲基)-1H-吡咯-3-甲腈;該殺生物組合物係大體上不含銅;及船用底漆;其中該吡啶硫酮鋅及該4-溴-2-(4-氯苯基)-5-(三氟甲基)-1H-吡咯-3-甲腈係以2.5:1至1:2之重量比於該塗料組合物中。
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- 2007-02-22 CN CNA200780007736XA patent/CN101400256A/zh active Pending
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- 2007-02-22 ES ES07751611.0T patent/ES2636810T3/es active Active
- 2007-02-22 KR KR1020077009121A patent/KR20070080261A/ko active Application Filing
- 2007-02-22 PT PT77516110T patent/PT1998619T/pt unknown
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- 2007-02-22 JP JP2008557319A patent/JP2009528356A/ja active Pending
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