CN101151291B - 聚合物组合物及其在制备活性或有效成分组合物中的用途 - Google Patents
聚合物组合物及其在制备活性或有效成分组合物中的用途 Download PDFInfo
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- CN101151291B CN101151291B CN2006800099434A CN200680009943A CN101151291B CN 101151291 B CN101151291 B CN 101151291B CN 2006800099434 A CN2006800099434 A CN 2006800099434A CN 200680009943 A CN200680009943 A CN 200680009943A CN 101151291 B CN101151291 B CN 101151291B
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Abstract
本发明涉及聚合物组合物、制备该聚合物组合物的方法和该聚合物组合物在生产水不溶性活性组分、特别是用于作物保护的活性成分的含水活性化合物组合物中的用途。
Description
本发明涉及一种新的聚合物组合物,涉及它们的制备方法,以及它们用于在水相中稳定水不溶性或水溶性差的活性化合物或有效物质的用途,和用于制备水不溶性的活性化合物或有效物质的活性化合物组合物的用途,特别是用于制备用于保护作物的活性化合物的用途。
活性化合物,即即使在低浓度下也能发挥生理作用的物质,通常以含水活性化合物组合物的形式使用或配制。因此,例如,在用于控制害虫的作物保护中使用的活性化合物,即杀虫剂、杀真菌剂和除草剂以及生长调节剂,通常作为浓缩物配制和销售,例如含水浓缩物,例如悬浮液或乳液,也可以作为固体浓缩物,例如粉末、粉剂或颗粒,它们在施用之前通过加入大量的水(“喷液”)而被稀释到所需要的施用浓度。已经证明含水活性化合物组合物本身可以用于药物和化妆品上的活性物质,和用于食品添加剂,例如维生素、微生物前体等。这同样适用于配制有效物质,即即使在低施用浓度下也能发挥规定的技术作用的低分子量化合物,例如着色剂和UV稳定剂。
在含水活性化合物组合物的情况下,通常的问题是活性化合物在水中的溶解性通常较差,通常在23℃/1013毫巴下小于10g/l。因此,这些活性化合物的含水配料以及含水的即用型制剂是多相体系,其中活性化合物作为被乳化和/或分散的相存在于连续水相中。为了稳定这些体系(这些体系本身是亚稳态的),通常使用乳化剂或分散剂。但是,它们的稳定作用通常是不令人满意的,使得活性化合物可以分离出例如乳油或沉淀物,特别是在含水配料在高温和/或在高度可变的温度或接近冰点的温度下储存较长时间的情况下。这一问题在活性化合物有结晶倾向时是特别显著的。当含有浓缩物形式的活性化合物的配料用水稀释时,也经常发生固体活性化合物颗粒的沉淀。
有机溶剂通常用于制备水不溶性活性化合物。因此水混溶性溶剂通常用作增溶剂,即增加活性化合物或有效物质在水相中的溶解性。水不混溶性溶剂进而用于将在施用温度下为固体的活性化合物转化成液相,该液相然后可以更容易地乳化。与固体活性化合物的悬浮液相比,在乳液中,活性化合物溶解在分子形式的溶剂液滴中,并进而更容易地获得,所以在施用时更有效。但是,由于VOC引起的公知问题,大量有机溶剂的使用不希望的,因为相关的操作卫生、环境因素和一些情况下也由于毒理性原因。
常规含水活性化合物组合物的另一个缺点是活性化合物颗粒以及悬浮和乳化的活性化合物液滴各自在水相中的较大颗粒尺寸,它们的尺寸通常在数微米的范围内。但是,所需要的是这样的配料,其中活性化合物以尽可能高程度分散的形式存在或在用水稀释时被转化成高度分散的形式,从而首先确保在配料中的均匀分布,进而具有更好的处理和计量性能,并同时增加活性化合物在配料中或在即用型组合物中的生物利用率。在这里,所需要的是这样的配料,其在用水稀释时能提供在含活性化合物的相中的平均粒径低于500nm和特别低于300nm的活性化合物组合物。
已经有许多建议使用两亲性嵌段共聚物在含水载体中增溶水不溶性活性化合物。术语“增溶”表示通过使用赋予溶解性的物质(助剂)来实现水不溶性活性化合物或有效物质在水相中的稳定均匀分布,而分散活性化合物相的颗粒通常小到使得它们难以分散可见光,所以该混合物表现为或多或少是透明的。在这里,两亲性嵌段共聚物通常含有至少一种亲水性聚合物嵌段和至少一种疏水性聚合物嵌段。
因此,例如,US2003/0009004为此目的建议了一种两亲性嵌段共聚物,其含有亲水性聚乙烯亚胺嵌段和可生物降解的脂族聚酯的疏水性嵌段。但是,该共聚物的缺点是基于活性化合物计,需要较大量的聚合物以实现稳定的含水活性化合物组合物。
US2003/0157170描述了不含水的活性化合物,其含有两亲性两嵌段共聚物和添加剂,其中两亲性两嵌段共聚物具有聚酯作为疏水性组分。在用水稀释时,该组合物形成了含有活性化合物的胶束。这些组合物的缺陷也是需要较大量的聚合物来稳定在水相中的活性化合物。
WO02/82900描述了两亲性嵌段共聚物用于制备水不溶性作物保护剂的水悬浮液的用途。所用的嵌段共聚物可以通过烯属不饱和单体的“活性”或“受控”自由基嵌段共聚反应来获得。除了这些方法比较复杂之外,含水活性化合物配料含有较大量的水溶性有机溶剂。此外,该方法要求使用有毒性的过渡金属催化剂,这些催化剂保留在产物中。此外,嵌段共聚物的颜色倾向于变成褐色。
总之,尽管嵌段共聚物提供了配制水不溶性活性化合物和有效物质的一般优点,但是现有技术公知的嵌段共聚物不能完全令人满意,不管是因为它们的制备方法非常复杂,还是因为含水活性化合物配料或活性化合物制剂的稳定性不令人满意,活性化合物的活性不利地受到影响,或者需要大量聚合物来稳定在水相中的活性化合物,这除了高成本之外,在使用这些制剂时也是不利的。
因此,本发明的目的是提供能有效增溶在含水介质中的水不溶性活性化合物的物质。这些物质应该适合用于制备允许有效稳定在水相中的活性化合物的配料。特别是,这些物质应该也适用于提供水不溶性活性化合物的含水活性化合物组合物,该组合物具有非常低含量(如果有的话)的挥发性有机化合物。此外,当加入电解质和在用水稀释期间,希望使用这些物质制备的含水活性化合物组合物具有对于在长期储存时破坏的高稳定性。
令人惊奇的是,该目的通过一种聚合物组合物来实现,该聚合物组合物通过使以下组分反应而获得:
a)至少一种聚合物P1,其带有对异氰酸酯基团有反应性的官能团R1,并且由烯属不饱和单体M1构成,其中单体M1含有基于单体M1总量计的多于20重量%的单体M1a,所述单体M1a具有选自以下的至少一个官能团FG:叔氨基、亚氨基、羧酰胺基、腈基、内酰胺基、酮基、醛基、脲基、聚醚基、羧基、磺酰基、羟基磺酰基和磺酰胺基,
b)至少一种聚C2-C4亚烷基醚P2,其带有对异氰酸酯基团有反应性的官能团R2,
c)至少一种化合物V,其带有异氰酸酯基团,并且关于异氰酸酯基团的官能度是至少1.5。
因此,本发明涉及所述的聚合物组合物和它们的制备方法。
在有利的方式中,本发明的聚合物组合物适用于稳定活性化合物和有效物质(它们在水中的溶解性差,如果有的话),从而使得有可能制备这些活性化合物和有效物质的含水配料,和在用于稀释时能获得活性化合物或有效物质在水相中的极高度分散的非水性配料制剂。与在现有技术中描述的嵌段共聚物相比,它们可以用于增溶基于聚合物的大量活性化合物,并且在水相中是稳定的。
因此,本发明还提供这里所述和下述聚合物组合物用于在含水介质中稳定活性化合物和/或有效物质的用途,所述稳定活性化合物和/或有效物质在水中的溶解性差或者不溶于水。
此外,本发明提供这里所述的聚合物组合物用于制备水不溶性或水溶性差的活性化合物和有效物质的配料的用途。在这方面,溶解性差是指在25℃和1013毫巴下,活性化合物或有效物质在水中的溶解度小于10g/l,通常小于5g/l,特别是小于1g/l,特别是小于0.1g/l。
本发明还提供活性化合物和有效物质组合物,其含有至少一种水溶性差或水不溶性的活性化合物和/或有效物质,和至少一种这里和下面所述的聚合物组合物。
本发明的活性化合物或有效物质组合物可以是固体或液体。这些组合物的优选实施方案涉及含水的(即液体的)活性化合物组合物,其具有水相作为连续相和至少一个分散相,所述分散相包含至少一种在25℃和1013毫巴下在水中的溶解度小于10g/l的活性化合物和/或有效物质,和至少一种根据本发明的聚合物组合物。
除了作为连续相的含水介质之外,使用本发明聚合物组合物制备的水不溶性活性化合物或有效物质的含水活性化合物组合物还含有至少一种含活性化合物和/或有效物质的相,其中活性化合物或有效物质以及两亲性聚合物组合物以聚集体的形式存在,该聚集体包含活性化合物或有效物质以及本发明聚合物组合物的聚合物组分。所以,这种含活性化合物或有效物质的相形成了包含活性化合物或有效物质和至少一种本发明聚合物组合物的分散相。
在连续水相中,活性化合物以极细分散的形式存在,其甚至可以是分子溶解的形式。认为在水相中,活性化合物与本发明的两亲性聚合物组合物形成了聚集体。通常,这些聚集体的平均粒径小于1微米,通常小于500nm,特别是小于400nm,尤其小于300nm,非常特别是小于200nm。根据聚合物和活性化合物或有效物质的性质和根据浓度比例,聚集体可以甚至如此小,以致它们不再以可检测的离散颗粒的形式存在,而是以溶解的形式存 在(粒径小于20nm或小于5nm)。如果聚集体以离散颗粒的形式存在,则颗粒的平均粒径通常为5-400nm,特别是10-300nm,特别优选是20-200nm。
本发明的进一步优选实施方案涉及一种非水性的、通常固体或半固体的活性化合物组合物,其含有至少一种在25℃/1013毫巴下在水中的溶解度小于10g/l的活性化合物和/或有效物质,和至少一种两亲性聚合物组合物,并且基本不含水或仅仅含有少量水,也就是说<10重量%的水。这些组合物可以含有在相应应用目的中常用的助剂和添加剂作为其它组分。
本发明的组合物(也就是说含水和非水性的组合物)提供了活性化合物或有效物质的制剂,它们在稀释时是含水的,包含连续的水相和含至少一种活性化合物或有效物质的相,所述含至少一种活性化合物或有效物质的相的平均粒径通常小于1微米,一般不大于500nm,经常不大于300nm,特别是不大于200nm或150nm,尤其不大于100nm,例如在10-300nm范围内,优选10-250nm,特别是20-200nm或20-150nm,和特别优选是30-100nm。
所述的粒径是重均粒径,可以通过动态光散射测定。本领域技术人员对于此测定方法是熟知的,例如参见H.Wiese在D.Distler,WassrigePolymerdispersionen[聚合物水分散液],Wiley-VCH1999,第4.2.1章,40页起,和其中引用的文献,以及H.Auweter,D.Horn,J.Colloid Interf.Sci.105(1985)399,D.Lilge,D.Horn,Colloid Polym.Sci.269(1991)704或H.Wiese,D.Horn,J.Chem.Phys.94(1991)6429。
在这里和以下,术语“含水介质”和“水相”包括水,水与基于混合物计最多10重量%的水混溶性有机溶剂的含水混合物,以及固体在水或在含水混合物中的溶液。水混溶性溶剂的例子包括C3-C4酮,例如丙酮和甲乙酮;环醚,例如二烷和四氢呋喃;C1-C4-链烷醇,例如甲醇、乙醇、正丙醇、异丙醇、正丁醇、叔丁醇;多元醇和它们的单-和二甲基醚,例如乙二醇、丙二醇、乙二醇单甲醚、二甘醇、二甘醇单甲醚、二甘醇二甲醚、甘油;以及C2-C3腈,例如乙腈和丙腈;二甲基亚砜,二甲基甲酰胺,甲酰胺,乙酰胺,二甲基乙酰胺,丁内酯,2-吡咯烷酮和N-甲基吡咯烷酮。
在这里和以下,术语“官能度”表示每分子或每个聚合物链中的相应官能团R1或R2的平均数目。
在这里和以下,术语“活性化合物组合物”是术语配料和制剂的同义词,也就是说在组合物中,其含有浓缩形式的活性化合物,和如果合适的话被稀释到所需的使用浓度以与水或含水液体一起使用。
本发明的含水活性化合物组合物,以及通过用水稀释含水或非水性的活性化合物组合物所获得的本发明活性化合物组合物,具有极高的抗破坏稳定性。在不出现分解的情况下,它们可以在数月的较长时间内储存,即使在高温和/或高度可变的温度下。因此,不存在任何问题地,浓度更高的制剂也可以用水稀释,且不存在破坏现象,例如凝聚、结晶、絮化或沉淀。此外,这些组合物的耐电解质能力强。另外,由于极细的分布,和由于活性化合物/有效物质的非常小的表观粒径聚集,活性化合物或有效物质的活性与常规配料相比得到增加。本发明活性化合物组合物的另一个优点是它们也可以作为低溶剂组合物配制(挥发性溶剂的含量<10重量%,基于活性化合物组合物的重量计)或甚至作为无溶剂的组合物配制(挥发性溶剂的含量<1重量%,基于活性化合物组合物的重量计)。
本发明聚合物组合物的另一个优点是活性化合物可以以固体形式配制。例如,本发明的液体活性化合物组合物,例如含水活性化合物组合物以及活性化合物或有效物质和聚合物组合物在有机溶剂中的溶液可以进行干燥,得到可再分散的固体物质,例如粉末或颗粒。这表示通过在干燥期间根据干燥条件除去水相或有机溶剂,获得了细分散的粉末或粗颗粒,它们可以毫无问题地溶解或分散在水中,且不会出现任何值得注意的粒径增加。
两亲性聚合物的另一个优点是根据聚合物组合物的性质,增溶性能可以经由pH控制。例如,如果聚合物P1具有羧基,则可以通过提高pH来降低增溶作用,这可以导致自发地释放活性化合物。进而,如果聚合物含有碱性基团,则增溶可以通过降低pH来降低。
用于制备本发明聚合物组合物的聚合物P1和聚C2-C4亚烷基醚P2分别具有对异氰酸酯基团有反应性的官能团R1和R2,并且与化合物V的异氰酸酯基团反应,形成键。合适的官能团的例子是羟基、巯基(SH)和伯氨基和仲氨基。优选的官能团是羟基,特别是与脂族或脂环族碳原子连接的羟基。
因为含异氰酸酯基团的化合物V具有平均至少1.5个异氰酸酯基团/每个分子,所以在V与聚合物P1和聚C2-C4亚烷基醚P2的反应中,形成了至少一些嵌段共聚物,其包含至少一种衍生自聚合物P1的聚合物嵌段和至少一种与之不同的衍生自聚C2-C4亚烷基醚P2的亲水性聚合物嵌段。与现有技术的两亲性嵌段共聚物相比,这些嵌段不是彼此直接连接,而是经由具有至少两个氨酯和/或脲基的连接剂连接。与现有技术的嵌段共聚物相比,所获得的聚合物组合物通常还含有少量的未反应的聚合物P1和/或P2,以及具有完全由聚合物P1衍生的聚合物嵌段或完全由聚C2-C4亚烷基醚P2衍生的聚合物嵌段的对称反应产物。但是,聚合物组合物的有利性能得到确保。
认为通过在聚合物嵌段P1中存在的官能团FG对活性化合物或有效物质的亲合性,在本发明聚合物组合物中的嵌段共聚物在水相中与活性化合物形成了聚集体。也认为聚合物嵌段P1与活性化合物一起形成了这些聚集体的中心,而亲水性聚醚链P2形成了聚集体的外部区域,因此稳定了在含水介质中的聚集体。官能团FG对要配制的活性化合物的亲合性可以例如基于离子性相互作用,基于偶极-偶极相互作用,基于氢键,基于π体系的相互作用,或基于这些相互作用的混合形式。
合适的聚合物P1原则上是由烯属不饱和单体M1构成的所有聚合物,该聚合物含有所需数目的反应性基团R1,其构成单体M1含有多于20重量%、特别是至少25重量%、特别优选至少30重量%和非常特别优选至少35重量%的官能化单体M1a。
单体M1a在单体M1中的比例可以是最多100重量%,并且有利地在25-90重量%的范围内,特别是30-80重量%,特别优选30-70重量%,非常特别优选35-60重量%。
根据本发明,除了烯属不饱和双键之外,单体M1a具有一个或多个、例如一个或两个官能团FG。通常,它们提高了单体M1a在水中的溶解度。因此,在25℃和1013毫巴下,单体M1a在水中的溶解度通常是至少50g/l,特别是至少80g/l。
单体M1a可以是酸性或阴离子性或碱性或中性的。
在第一个优选实施方案中,单体M1a含有基本上仅仅中性单体M1a。
在第二个优选实施方案中,单体M1a含有基本上仅仅碱性单体M1a。
在第三个优选实施方案中,单体M1a含有基本上仅仅酸性单体M1a。
在第四个优选实施方案中,单体M1a含有基本上中性和碱性单体M1a的混合物。在该实施方案中,中性单体对碱性单体的重量比优选是1∶10至10∶1,特别是5∶1至1∶2。
在第五个优选实施方案中,单体M1a含有基本上中性和酸性单体M1a的混合物。在该实施方案中,中性单体对酸性单体的重量比优选是1∶10至10∶1,特别是5∶1至1∶2。
在实施方案1-5中,特别优选实施方案1、2和4。
在这里,“基本上”表示至少90重量%、特别是至少95重量%,基于单体M1a的重量计。
中性单体M1a包括例如:
-单烯属不饱和C3-C8单羧酸的酰胺和C1-C4烷氧基烷基酰胺,例如丙烯酰胺、甲基丙烯酰胺、N-(甲氧基甲基)(甲基)丙烯酰胺、N-(乙氧基甲基)(甲基)丙烯酰胺、N-(2-甲氧基乙基)(甲基)丙烯酰胺、N-(2-乙氧基乙基)(甲基)丙烯酰胺等;
-单烯属不饱和腈,例如丙烯腈和甲基丙烯腈;
-脂族、脂环族或芳族羧酸的N-乙烯基酰胺,特别是具有1-4个碳原子的脂族羧酸的N-乙烯基酰胺,例如N-乙烯基甲酰胺、N-乙烯基乙酰胺、N-乙烯基丙酰胺和N-乙烯基丁酰胺;
-具有5-7个环原子的N-乙烯基内酰胺,例如N-乙烯基吡咯烷酮、N-乙烯基哌啶酮、N-乙烯基吗啉酮和N-乙烯基己内酰胺;
-带有脲基的单烯属不饱和单体,例如N-乙烯基-和N-烯丙基脲,以及咪唑啉-2-酮的衍生物,例如N-乙烯基-和N-烯丙基咪唑啉-2-酮、N-乙烯基氧基乙基咪唑啉-2-酮、N-烯丙基氧基乙基咪唑啉-2-酮、N-(2-丙烯酰氨基乙基)-咪唑啉-2-酮、N-(2-丙烯酰氧基乙基)-咪唑啉-2-酮、N-(2-甲基丙烯酰氨基乙基)-咪唑啉-2-酮、N-(2-甲基丙烯酰氧基乙基)-咪唑啉-2-酮(=甲基丙烯酸脲基酯)、N-[2-(丙烯酰氧基乙酰氨基)乙基]-咪唑啉-2-酮、N-[2-(2-甲基丙烯酰氧基乙酰氨基)乙基]-咪唑啉-2-酮、N-[2-(2-丙烯酰氧基乙酰氨基)乙基]-咪唑啉-2-酮;
-具有醛基或酮基的单烯属不饱和单体,例如3-(丙烯酰氨基)-3-甲基丁-2-酮(二丙酮丙烯酰胺)、3-(甲基丙烯酰氨基)-3-甲基丁-2-酮、丙烯酸2,4-二氧杂戊基酯和甲基丙烯酸2,4-二氧杂戊基酯。
优选的中性单体是N-乙烯基内酰胺,特别是N-乙烯基吡咯烷酮,以及带有脲基的单体,特别是N-(2-丙烯酰氨基乙基)-咪唑啉-2-酮和N-(2-甲基丙烯酰氨基乙基)-咪唑啉-2-酮。
碱性单体M1a包括例如:
-乙烯基取代的氮杂芳族化合物,例如2-、3-和4-乙烯基吡啶,N-乙烯基咪唑;和
-具有伯、仲或叔氨基的单烯属不饱和单体,特别是式I的单体:
其中
X是氧或基团N-R4a,
A是C2-C8亚烷基,例如1,2-乙二基、1,2-或l,3-丙二基,1,4-丁二基或2-甲基-1,2-丙二基,它们如果合适的话可以被1、2或3个不相邻的氧原子间隔,例如3-氧杂戊烷-1,5-二基;
R1a、R1b彼此独立地是氢、C1-C10烷基、C5-C10环烷基、苯基或苯基-C1-C4烷基,特别都是C1-C4烷基;
R2a是氢或C1-C4烷基,特别是氢或甲基;
R3a是氢或C1-C4烷基,特别是氢;和
R4a是氢或C1-C4烷基,特别是氢。
式I单体的例子是丙烯酸2-(N,N-二甲基氨基)乙基酯、甲基丙烯酸2-(N,N-二甲基氨基)乙基酯、2-(N,N-二甲基氨基)乙基丙烯酰胺、丙烯酸3-(N,N-二甲基氨基)丙基酯、甲基丙烯酸3-(N,N-二甲基氨基)丙基酯、3-(N,N-二甲基氨基)丙基丙烯酰胺、3-(N,N-二甲基氨基)丙基甲基丙烯酰胺和2-(N,N-二甲基氨基)乙基甲基丙烯酰胺,其中特别优选甲基丙烯酸3-(N,N-二甲基氨基)丙基酯。
优选的碱性单体M1a是通式I的单体。
此外,单体M1a还包括阴离子或酸性的单烯属不饱和单体。它们的例子是:
-具有磺酸基团的单烯属不饱和单体,以及这些单体的盐,特别是碱金属盐,例如是钠盐或钾盐,以及铵盐。这些包括烯属不饱和磺酸,特别是乙烯基磺酸,2-丙烯酰氨基-2-甲基丙磺酸、2-丙烯酰氧基乙磺酸和2-甲基丙烯酰氧基乙磺酸,3-丙烯酰氧基-和3-甲基丙烯酰氧基丙磺酸,乙烯基苯磺酸以及它们的盐;
-烯属不饱和膦酸,例如乙烯基膦酸和乙烯基膦酸二甲基酯以及它们的盐;和
-带有一个或两个羧基的单烯属不饱和单体,例如α,β-烯属不饱和C3-C8单-和C4-C8二-羧酸,特别是丙烯酸、甲基丙烯酸、巴豆酸、马来酸、富马酸和衣康酸。
优选的酸性单体M1a是上述具有一个或两个羧基的单烯属不饱和单体。
除了单体M1a之外,所述聚合物还可以含有最多<80重量%的与单体M1a不同的烯属不饱和单体。这些优选是中性的单烯属不饱和单体M1b,其在25℃和1巴下具有优选不大于30g/l、特别不大于25g/l的在水中的有限溶解度。认为通过疏水相互作用,这些单体促进了形成活性化合物/聚合物聚集体。因此,基于单体M1的重量计,聚合物P1含有最多10-75重量%、特别最多20-70重量%、特别优选30-70重量%、尤其40-65重量%的单体M1b。
单体M1b特别包括式II的单体:
其中
X是氧或基团N-R4a,
R1是C1-C20烷基、C5-C10环烷基、苯基、苯基-C1-C4烷基或苯氧基-C1-C4烷基;
R2是氢或C1-C4烷基;
R3是氢或C1-C4烷基;和
R4是氢或C1-C4烷基。
优选的通式II单体是其中式II中的R3是氢的那些。在式II中,R2优选是氢或甲基。式II中的X优选是O、NH、NCH3或NC2H5,特别优选是O。
式II中的R1优选是:
-C1-C20烷基,特别是C1-C10烷基,例如乙基、正丙基、异丙基、正丁基、2-丁基、异丁基、叔丁基、1-戊基、2-戊基、新戊基、正己基、2-己基、正辛基、2-乙基己基、2-丙基庚基、正癸基、月桂基或硬脂基,
-C5-C10环烷基,例如环戊基、环己基或甲基环己基,
-苯基-C1-C4烷基,例如苄基、1-或2-苯基乙基、1-、2-或3-苯基丙基,或
-苯氧基-C2-C4烷基,例如2-苯氧基乙基。
R1特别是C2-C10烷基。同样,R1优选是甲基或2-苯氧基乙基。
特别优选的式II单体是丙烯酸与C2-C10链烷醇形成的酯(=丙烯酸C2-C10烷基酯),例如丙烯酸乙酯、丙烯酸正丁酯、丙烯酸异丁酯、丙烯酸叔丁酯、丙烯酸正己酯、丙烯酸2-乙基己基酯和丙烯酸3-丙基庚基酯;甲基丙烯酸与C2-C10链烷醇形成的酯,例如甲基丙烯酸甲酯、甲基丙烯酸乙酯、甲基丙烯酸正丁酯、甲基丙烯酸异丁酯、甲基丙烯酸叔丁酯和甲基丙烯酸正己酯。此外,优选的单体M1b是丙烯酸和甲基丙烯酸与2-苯氧基乙醇形成的酯,例如丙烯酸2-苯氧基乙酯。此外,优选的单体M1b是丙烯酸和甲基丙烯酸的N-(C2-C10烷基)酰胺,以及丙烯酸和甲基丙烯酸的N-(C1-C2烷基)-N-(C2-C10烷基)酰胺,例如N-乙基丙烯酰胺、N,N-二乙基丙烯酰胺、N-丁基丙烯酰胺、N-甲基-N-丙基丙烯酰胺、N-(正己基)-丙烯酰胺、N-(正辛基)-丙烯酰胺和相应的甲基丙烯酰胺。单体M1b特别含有至少50重量%、特别是至少70重量%的至少一种甲基丙烯酸C1-C4烷基酯(R1=C1-C4烷基,R2=CH3,R3=H),基于单体M1a的总量计,其中特别优选甲基丙烯酸甲酯和甲基丙烯酸叔丁酯。
此外,单体M1b包括:
-乙烯基芳族单体,例如苯乙烯、α-甲基苯乙烯、乙烯基甲苯等,
-具有2-20个碳原子的烯烃,优选具有3-10个碳原子的α-烯烃,例如丙烯、1-丁烯、1-戊烯、1-己烯、1-辛烯、二异丁烯和1-癸烯,
-脂族羧酸的乙烯基酯,例如乙酸乙烯酯、丙酸乙烯酯、月桂酸乙烯酯、壬酸乙烯酯、癸酸乙烯酯、月桂酸乙烯酯和硬脂酸乙烯酯,
-卤代烯烃,例如氯乙烯,
-具有优选3-6个碳原子的单烯属不饱和单羧酸的C11-C20烷基酯,例如丙烯酸C11-C20烷基酯和甲基丙烯酸C11-C20烷基酯,例如丙烯酸月桂基酯、甲基丙烯酸月桂基酯、丙烯酸异十三烷基酯、甲基丙烯酸异十三烷基酯、丙烯酸硬脂基酯、甲基丙烯酸硬脂基酯,
-具有优选4-8个碳原子的烯属不饱和二羧酸的二-C1-C20烷基酯,例如富马酸和马来酸的二-C1-C20烷基酯,例如富马酸二甲酯、马来酸二甲酯、富马酸二丁酯和马来酸二丁酯,
-具有优选3-6个碳原子的单烯属不饱和单羧酸的缩水甘油酯,例如丙烯酸缩水甘油酯和甲基丙烯酸缩水甘油酯。
优选的单体M1b是式II的单体和另外乙烯基芳族单体,其中特别优选苯乙烯。优选的单体M1b也是上述单体M1b的混合物,包含主要特别是至少60重量%、特别优选70重量%、例如60-99重量%或70-99重量%的式II单体或式II单体与苯乙烯和至少一种与之不同的单体M1b的混合物,基于单体M1b的总量计。
除了单体M1a和M1b之外,聚合物P1可以含有最多20重量%、特别不大于10重量%的与单体M1a和M1b不同的烯属不饱和单体M1c,基于单体M1的总量计。
单体M1c包括具有至少一个阳离子基团的单烯属不饱和单体M1c.k。单体M1c.k特别包括具有季铵基团或季化亚氨基的那些。具有季化亚氨基的单体的例子是N-烷基乙烯基吡啶盐和N-烷基-N'-乙烯基咪唑盐,例如N-甲基-N'-乙烯基咪唑氯化物或甲基硫酸盐。这些单体M1c.k中,特被优选式III的单体:
其中
R5是氢或C1-C4烷基,特别是氢或甲基,
R6、R7和R8彼此独立地是C1-C4烷基,特别是甲基,和
Y是氧、NH或NR9,其中R9是C1-C4烷基,
A是C2-C8亚烷基,例如1,2-乙二基、1,2-或1,3-丙二基、1,4-丁二基或2-甲基-1,2-丙二基,其任选地被1、2或3个不相邻的氧原子间隔,例如在3-氧杂戊烷-1,5-二基中,和
Z-是阴离子等价物,例如Cl-、HSO4 -、1/2SO4 2-或CH3OSO3 -等。
这些单体M1c.k的例子是:
2-(N,N,N-三甲基铵)乙基丙烯酸酯氯化物,
2-(N,N,N-三甲基铵)乙基甲基丙烯酸酯氯化物,
2-(N,N,N-三甲基铵)乙基甲基丙烯酰胺氯化物,
3-(N,N,N-三甲基铵)丙基丙烯酸酯氯化物,
3-(N,N,N-三甲基铵)丙基甲基丙烯酸酯氯化物,
3-(N,N,N-三甲基铵)丙基丙烯酰胺氯化物,
3-(N,N,N-三甲基铵)丙基甲基丙烯酰胺氯化物,
2-(N,N,N-三甲基铵)乙基丙烯酰胺氯化物,和相应的甲基硫酸盐和硫酸盐。
单体M1c.k在单体M1中的比例有利地不超过20重量%,例如0.1-20重量%,特别是0.5-15重量%,特别是1-10重量%。在优选实施方案中,聚合物P1不含单体M1c.k或含有不超过0.1重量%的单体M1c.k。
单体M1c也包括具有两个或更多个非共轭烯属不饱和双键的单体M1c.v。单体M1c.v的比例通常不超过2重量%,特别不超过0.5重量%,基于单体M1的总量计。单体M1c.v的例子是单烯属不饱和羧酸的乙烯基和烯丙基酯,例如丙烯酸烯丙酯和甲基丙烯酸烯丙酯,二或多元醇的二-和聚丙烯酸酯,例如乙二醇二丙烯酸酯、乙二醇二甲基丙烯酸酯、丁二醇二丙烯酸酯、丁二醇二甲基丙烯酸酯、己二醇二丙烯酸酯、己二醇二甲基丙烯酸酯、三甘醇二丙烯酸酯、三甘醇三甲基丙烯酸酯、三(羟基甲基)乙烷三丙烯酸酯和三(羟基甲基)乙烷三甲基丙烯酸酯、季戊四醇三丙烯酸酯和季戊四醇三甲基丙烯酸酯,另外还有多官能羧酸的烯丙酯和甲代烯丙酯,例如马来酸二烯丙酯、富马酸二烯丙酯、邻苯二甲酸二烯丙酯。典型的单体M1c.3也是化合物例如二乙烯基苯、二乙烯基脲、二烯丙基脲、氰脲酸三烯丙酯、N,N'-二乙烯基-和N,N’-二烯丙基-咪唑啉-2-酮,以及亚甲基二丙烯酰胺和亚甲基二甲基丙烯酰胺。
在特别优选的实施方案2a中,基于单体M1的总量计,聚合物P1包含20-80重量%、特别是25-60重量%的碱性单体M1a和20-80重量%、特别是40-75重量%的单体M1b。
在实施方案2a中,优选的单体M1a是乙烯基取代的氮杂芳族化合物,特别是上述乙烯基吡啶和式I单体。特别优选的单体M1a是式I的单体。
在实施方案2a中,优选的单体M1b是式II单体和乙烯基芳族单体,其中特别优选苯乙烯。优选的单体M1b也是上述单体M1b的混合物,包含主要特别是至少60重量%、特别优选70重量%、例如60-99重量%或70-99重量%的式II单体的混合物或式II单体与苯乙烯和至少一种与之不同的单体M1b的混合物,基于单体M1b的总量计。单体M1b特别完全或基本完全包含通式II的单体(>95重量%),特别是两种或多种不同的丙烯酸或甲基丙烯酸的酯的混合物(R2=H或甲基,R3=H,X=O)。
在优选的实施方案中,单体M1b是甲基丙烯酸C1-C4烷基酯(例如甲基丙烯酸甲酯)与(甲基)丙烯酸苯基-C1-C4烷基酯或(甲基)丙烯酸苯氧基-C1-C4烷基酯(例如甲基丙烯酸2-苯氧基乙基酯)的混合物。
在进一步特别优选的实施方案3a中,基于单体M1的总量计,聚合物P1包含20-80重量%、特别是25-60重量%的带有羧基的单体M1a和20-80重量%、特别是40-75重量%的单体M1b。
在实施方案3a中,优选的单体M1a是单烯属不饱和的单羧酸和二羧酸,特别是丙烯酸、甲基丙烯酸、衣康酸、马来酸和富马酸。
在实施方案3a中,优选的单体M1b是式II单体、C2-C10烯烃和乙烯基芳族单体,特别是苯乙烯、甲基丙烯酸C2-C8烷基酯,例如甲基丙烯酸甲酯、甲基丙烯酸正丁酯、甲基丙烯酸叔丁酯、甲基丙烯酸正己酯和甲基丙烯酸2-乙基己基酯。
根据本发明,聚合物P1可以带有反应性官能团R1,其与异氰酸酯基团反应形成键。这些基团/每个聚合物分子的平均数(官能度)通常不超过3,经常不超过2,例如是0.3-3,一般是0.5-2,或优选是0.3-1.8,特别是0.5-1.5,尤其是0.6-1.4。官能团R1可以位于聚合物链中,优选处于聚合物链的末端。
考虑到本发明聚合物组合物用于配制活性化合物的用途,疏水性聚合物P1优选具有500-20000道尔顿的数均分子量,特别是1500-15000道尔顿。
一般而言,聚合物P1是现有技术公知的,例如US5,556,918和EP-A742238。它们通常通过单体M1在引发剂存在下和任选地在调节剂存在下进行自由基引发的溶液聚合来制备,前提是该引发剂在分解时产生羟基自由基(OH)或具有羟基的链段和/或该调节剂含有OH基团或NH2基团。合适的引发剂是有机氢过氧化物,例如氢过氧化叔丁基、四氢呋喃氢过氧化物、枯烯氢过氧化物;或带有羟基的偶氮引发剂,例如2,2’-偶氮二(2-甲基-N-(2-羟乙基)丙酰胺)。合适的调节剂是氨基醇、氨基硫醇、氨基酚和特别是硫代醇,例如3-羟基丙硫醇、2-羟基乙基-2-巯基丙酸酯,特别是2-羟基乙硫醇(巯基乙醇)和巯基甘油,以及氨基硫醇,例如半胱胺(=2-氨基乙硫醇)。如果使用这种调节剂,则聚合反应也可以在常规引发剂的存在下进行,例如常规的偶氮引发剂或有机过氧化物,例如偶氮二异丁腈、二叔丁基过氧化物、过氧化二癸酰、过氧化二苯甲酰、过乙酸叔丁酯或2-甲基过丙酸叔丁酯。如果聚合在上述一种调节剂的存在下进行,则调节剂的用量通常是0.1-5重量%,通常是0.2-4重量%,特别是0.5-3重量%,基于单体M1的总量计。引发剂的用量通常是0.05-5重量%,通常是0.1-4重量%,特别是0.2-3重量%,基于要聚合的单体M1的总量计。
对于单体M1的聚合反应而言合适的溶剂例如是链烷醇,例如甲醇、乙醇、正丙醇、异丙醇;脂族酮,例如丙酮、甲乙酮、环己酮;羧酸的烷基酯,例如乙酸甲酯、乙酸乙酯、丙酸甲酯、丙酸乙酯、乙酸正丁酯;脂环和环状的醚,例如乙醚、二异丙醚、甲基叔丁基醚、四氢呋喃;芳族、脂族和脂环族的烃,例如甲苯、二甲苯、己烷、环己烷;腈,例如乙腈;以及N-烷基内酰胺,例如N-甲基吡咯烷酮、N-乙基吡咯烷酮,以及这些溶剂的混合物。
进一步细节可以参考EP742 238的第3页,其公开内容引入本文供参考。
根据本发明,聚合物P2是直链或支化的聚C2-C4亚烷基醚,即基本(基于聚合物P2重量计的至少90重量%)由式IV重复单元构成的聚合物:
其中A是C2-C4亚烷基,例如乙烷-1,2-二基、丙烷-1,2-二基、丙烷-1,3-二基、丁烷-1,2-二基或丁烷-1,3-二基。在聚合物P2中,优选由至少50重量%、优选至少70重量%、特别是至少80重量%和特别是至少90重量%的氧化乙烯单元构成的那些,即式IV的基团,其中A是1,2-乙烷二基。另外,脂族聚醚可以具有衍生自氧化C3-C4亚烷基的结构单元。
在聚合物P2中,优选具有关于官能团R2的官能度F2为0.5-3、特别是0.6-2.5的那些。
聚合物P2的数均分子量按照常规方法由GPC测定,优选是500-20000道尔顿,特别是800-15000道尔顿。
特别优选的聚醚P2是式V的那些:
Ra-X-(CHRb-CH2-O)p-H (V)
其中
Ra是氢、C1-C20烷基或苄基,
X是氧或NH,
Rb是氢或甲基,其中至少50摩尔%、特别至少70摩尔%和优选至少90摩尔%的基团Rb是氢,
p是平均值在10-500、优选20-250和特别是25-100范围内的整数(数均)。
在本发明的聚合物组合物中,聚合物P1的总比例(即反应的和未反应的聚合物P1的总量)优选是基于聚合物P1、聚合物P2和化合物V的总重量计的9-90重量%,特别是20-68重量%。
在本发明的聚合物组合物中,聚醚P2的总比例(即反应的和未反应的聚合物P2的总量)优选是基于聚合物P1、聚醚P2和化合物V的总重量计的9-90重量%,特别是30-78重量%。
在本发明的聚合物组合物中,化合物V的总比例(即所用的化合物V的总量)优选是基于聚合物P1、聚醚P2和化合物V的总重量计的1-20重量%,特别是2-15重量%。
在本发明的聚合物组合物中,聚合物P1对聚醚P2的重量比,在每种情况下按照用于制备的聚合物的总量计,优选是1∶10至10∶1,特别是1∶4至2.2∶1。
具有关于异氰酸酯基的官能度为至少1.5、特别是1.5-4.5、尤其1.8-3.5的合适的化合物V包括脂族、脂环族和芳族的二异氰酸酯和多异氰酸酯,以及脂族、脂环族和芳族二异氰酸酯的异氰脲酸酯、脲基甲酸酯、脲二酮和缩二脲。
化合物V优选具有平均1.8-3.5个异氰酸酯基/每个分子。合适的化合物V例如是芳族二异氰酸酯,例如甲苯2,4-二异氰酸酯,甲苯2,6-二异氰酸酯,甲苯2,4-和2,6-二异氰酸酯的商业混合物(TDI),n-亚苯基二异氰酸酯,3,3’-二苯基-4,4'-二亚苯基二异氰酸酯,4,4’-二亚苯基二异氰酸酯,4,4’-二苯基甲烷二异氰酸酯,3,3'-二氯-4,4'-二亚苯基二异氰酸酯,枯烯2,4-二异氰酸酯,1,5-萘二异氰酸酯,p-苯二甲撑二异氰酸酯,p-亚苯基二异氰酸酯,4-甲氧基-1,3-亚苯基二异氰酸酯,4-氯-1,3-亚苯基二异氰酸酯,4-乙氧基-1,3-亚苯基二异氰酸酯,2,4-二亚甲基-1,3-亚苯基二异氰酸酯,5,6-二甲基-1,3-亚苯基二异氰酸酯,2,4-二异氰酸酯基二苯基醚;脂族二异氰酸酯,例如亚乙基二异氰酸酯、乙叉基二异氰酸酯、亚丙基1,2-二异氰酸酯、1,6-六亚甲基二异氰酸酯、1,4-四亚甲基二异氰酸酯、1,10-十亚甲基二异氰酸酯;和脂环族二异氰酸酯,例如异佛尔酮二异氰酸酯(IPDI)、亚环己基1,2-二异氰酸酯、亚环己基1,4-二异氰酸酯和二(4,4’-二异氰酸酯基环己基)甲烷。在这些二异氰酸酯中,优选其异氰酸酯基的活性不同的那些,例如甲苯2,4-二异氰酸酯,甲苯2,6-二异氰酸酯,以及顺-和反-异佛尔酮二异氰酸酯的混合物。
在本发明的另一个优选实施方案中,脂族或脂环族二异氰酸酯化合物的缩二脲或异氰脲酸酯,例如四亚甲基二异氰酸酯或六亚甲基二异氰酸酯的氰脲酸酯,用于制备本发明的聚合物组合物。
为了制备本发明的聚合物组合物,疏水性聚合物P1和亲水性聚醚P2接连或同时与化合物V反应,反应条件使得基团R1和/或R2与异氰酸酯基团反应形成键。
该反应在不存在或存在少量能促进形成聚氨酯或脲的常规催化剂的情况下进行。合适的催化剂是例如叔胺,例如三乙胺、三正丙基胺、N-甲基吡咯烷、N-甲基哌啶和二氮杂双环辛烷(DABCO);有机锡化合物,特别是脂族羧酸的二烷基锡(IV)盐,例如二月桂酸二丁锡和二辛酸二丁锡;二链烷酸锡(II),例如二辛酸锡;正钛酸四烷基酯,例如正钛酸四丁基酯;和铯盐,例如乙酸铯。如果需要,催化剂的用量不超过基于化合物V计的0.1重量%,例如是0.01-0.1重量%,特别是最多0.05重量%。
所需的反应温度当然取决于官能团R1或R2的反应活性和取决于异氰酸酯化合物V,和若使用的话,取决于催化剂的类型和用量。该温度通常是10-120℃,特别是15-85℃。
显然,聚合物P1和P2与化合物V之间的反应在不存在水分的情况下进行(水含量优选<10000ppm,特别是<2000ppm)。
P1和P2与化合物V之间的反应可以在本体中进行,或在对化合物V的异氰酸酯基呈惰性的有机溶剂中进行。合适溶剂的例子是脂族酮,例如丙酮、甲乙酮、环己酮;脂族羧酸的烷基酯,例如乙酸甲酯、乙酸乙酯、丙酸甲酯、丙酸乙酯、乙酸正丁酯;脂环和环状的醚,例如乙醚、二异丙醚、甲基叔丁基醚、四氢呋喃;芳族、脂族和脂环族的烃,例如甲苯、二甲苯、己烷、环己烷;腈,例如乙腈;以及N-烷基内酰胺,例如N-甲基吡咯烷酮、N-乙基吡咯烷酮,以及这些溶剂的混合物。
聚合物P1和P2与化合物V之间的反应可以接连或同时进行,即聚合物P1和P2可以接连地或同时地与化合物V反应。
如果聚合物P1和P2接连地与化合物V接连反应,则可以都先使聚合物P1与化合物V反应,然后使聚醚P2与化合物V反应,或者相反。
如果聚合物P1和P2接连地与化合物V反应,则反应优选进行使得在与第一种聚合物P1或P2反应之后,化合物V中的至少10摩尔%至90摩尔%、特别是20-80摩尔%的异氰酸酯基团已经与官能团R1和/或R2反应,并且所存在的10-90摩尔%、特别是20-80摩尔%的异氰酸酯基团仍然可用。然后是与第二种聚合物P1或P2反应。因此,第一种聚合物P1或P2的用量优选使得反应性基团R1和/或R2与每个分子V中的异氰酸酯数目之间的比率是0.1∶1至0.9∶1,特别是0.2∶1至0.8∶1。以此方式获得的产物然后与第二种聚合物反应,第二种聚合物P1或P2的用量优选使得反应性基团R1+R2的总量对应于至少化合物V的异氰酸酯基团数目。优选,R1+R2与异氰酸酯基团总量之比不超过1.2∶1。
如果聚合物P1和P2同时与异氰酸酯化合物V反应,则聚合物P1和P2的用量优选使得反应性基团R1+R2与异氰酸酯基团之间的摩尔比是至少1∶1。优选R1+R2与异氰酸酯基团总量之比不超过1.2∶1。
在该反应中,异氰酸酯化合物V可以原样使用。但是,也可以使用这样形式的异氰酸酯化合物V,其中一部分异氰酸酯基团被保护基团可逆地封闭。许多能封闭(封端或保护)异氰酸酯基团的化合物已经描述在文献中(参见例如Z.W.Wicks,Prog.Org.Coat.3(1975)73-99和9(1981)3-28或Houben-Weyl,Methoden der Organischen Chemie[有机化学的方法],第XIV/2卷,第61页起,Georg Thieme Verlag,Stuttgart1963)。可以提到的异氰酸酯基团封闭剂的例子是苯酚、己内酰胺、咪唑、吡唑、吡唑烷酮、1,2,4-三唑、二酮基哌嗪、丙二酸酯和肟。但是,为了成功地达到本发明的结果,不是必须使用以可逆方式被部分封闭的异氰酸酯。
在本发明的一个特别优选的实施方案中,在第一反应步骤中,疏水性聚合物P1按照上述方式通过自由基溶液聚合制备,而且与异氰酸酯化合物V的反应在所得液体反应混合物中按照这里描述的方式进行,不需要预先分离聚合物P1。所得的反应混合物然后与聚合物P2反应,优选与聚醚反应。或者,所需量的聚醚P2可以加入以此方式制得的聚合物P1中,然后与化合物V反应。
为了制备所述含水活性化合物配料,根据本发明获得的聚合物组合物可以从反应混合物中分离出来。但是,也可以原样使用反应混合物。
在本发明的一个优选实施方案中,用于制备聚合物组合物的溶剂被水部分或全部代替,这得到聚合物组合物的水分散液。这可以例如通过先通过蒸馏除去溶剂、然后将残余物分散在水或含水介质中来实现。也可以向聚合物组合物的溶液中加入水并在添加水之后除去溶剂,或者同时进行。
本发明的活性化合物组合物可以通过不同的方式制备。本发明的活性化合物或有效物质组合物的制备通常包括制备或提供含有本发明聚合物组合物和至少一种活性化合物和/或有效物质组合物的均匀的非水性混合物。
在本发明的第一个实施方案中,含水活性化合物组合物如下制备:先制备含有本发明聚合物组合物和活性化合物和/或有效物质组合物的均匀的非水性混合物,然后将所得的混合物分散在水或含水介质中。为了制备均匀的非水性混合物,通常将活性化合物引入液体形式的聚合物组合物中,例如熔体或优选在有机溶剂中的溶液。如果使用溶剂,则溶剂随后尽可能地除去,优选完全除去,得到活性化合物在聚合物组合物中的固溶体。适用于此目的的溶剂一般是能溶解活性化合物和聚合物的那些溶剂,例如脂族腈,例如乙腈和丙腈;脂族羧酸的N,N-二烷基酰胺,例如二甲基甲酰胺和二甲基乙酰胺;N-烷基内酰胺,例如N-甲基吡咯烷酮;上述脂族和脂环族醚,例如四氢呋喃;卤代烃,例如二氯甲烷、二氯乙烷,以及上述溶剂的混合物。为了制备本发明的含水组合物,所得的活性化合物在聚合物组合物中的固溶体随后通过在含水介质中搅拌而分散。搅拌可以在室温或高温下进行,例如10-80℃,特别是20-50℃。
在本发明的第二个实施方案中,含水活性化合物组合物如下制备:将活性化合物和/或有效物质引入聚合物组合物的水溶液/水分散液中。这通常通过在比活性化合物或有效物质的熔点更高的温度下进行,优选在活性化合物或有效物质具有低粘度的温度下进行,即1-1000mPa.s的粘度(根据DIN53019-2于25℃检测)。引入操作优选使用强剪切力进行,例如在Ultraturrax中。
在本发明的第三个实施方案中,含水活性化合物组合物通过包括以下步骤a-c的方法制备:
a)制备活性化合物和/或有效物质和如果合适的聚合物组合物在沸点低于水的有机溶剂中的溶液,和
b)将活性化合物和/或有效物质的溶液与水或含两亲性共聚物的水溶液混合,和
c)除去溶剂。
或者,这可以按以下方式进行:活性化合物的溶液包含聚合物组合物并将该溶液与水混合;或活性化合物的溶液不包含或包含仅仅部分聚合物组合物,并将该溶液与聚合物组合物的水溶液或分散液混合。混合可以在适合的搅拌容器中进行,可以先加入水或聚合物组合物的水溶液、然后加入活性化合物或有效物质的溶液,或者先加入活性化合物或有效物质的溶液、然后加入水或聚合物组合物的水溶液。然后除去有机溶剂,例如通过蒸馏进行,其中在合适时加入水。
在该实施方案的优选变形中,活性化合物溶液和水或聚合物组合物的水溶液被连续加入混合区中,然后从混合区连续地除去混合物,要从该混合物中除去溶剂。混合区可以按照需要设计。一般而言,能允许连续混合液体料流的所有装置适用于此目的。这些装置例如从Continuous Mixing ofFluids(J.-H.Henzler),Ullmann’s Encyclopedia第5版,CD-Rom,Wiley-VCH中得知。混合区可以设计成静态或动态混合器或其混合形式。合适的混合区特别也是喷射混合器或相应的具有喷嘴的混合器。在优选的实施方案中,混合区是“Handbook of Industrial Crystallization”(A.S.Myerson,1993 Butterworth-Heinemann,第139页,ISBN 0-7506-9155-7)中所描述的设备,或相应的设备。
活性化合物溶液与水或本发明聚合物组合物的水溶液之间的体积比可以在宽范围内变化,优选在10∶1至1∶20的范围内,特别是5∶1至1∶10。
溶剂的性质应当使得本发明的聚合物组合物和活性化合物按照所需的比例溶解。通过标准实验,本领域技术人员能确定合适的溶剂。合适溶剂的例子是C2-C4链烷醇,例如乙醇、正丙醇、正丁醇、异丁醇;上述脂族和脂环族的醚,例如乙醚、二异丙醚、甲基叔丁基醚、二烷、四氢呋喃;酮,例如丙酮、甲乙酮;内酯,例如γ-丁内酯;碳酸酯,例如碳酸二乙酯、碳酸亚乙酯、碳酸亚丙酯;内酰胺,例如吡咯烷酮、N-甲基吡咯烷酮、N-乙基吡咯烷酮、己内酰胺;脂族羧酸的酰胺,例如乙酰胺、N,N-二甲基乙酰胺、N,N-二甲基甲酰胺;腈,例如乙腈和丙腈等。
在本发明的另一个实施方案中,非水性的活性化合物组合物通过制备本发明聚合物组合物和活性化合物和/或有效物质的均匀的非水性混合物来制备。除非该组合物包含液体组分,它通常是固体的。关于这些组合物的制备,类似地适用上述在制备包含两亲性聚合物组合物和活性化合物和/或有效物质的均匀的非水性混合物的第一实施方案中的描述;但是,在这点上,如果合适的话,可以按照本身公知的方式向该组合物中引入所需要的添加剂和助剂。这种方案特别适用于制备无溶剂的不含水的固体组合物,也用于制备含溶剂的配料。
已经发现有利的是在本发明的含水活性化合物组合物中,活性化合物和/或有效物质对聚合物组合物的重量比是1∶10至3∶1,特别是1∶5至2∶1。
活性化合物和/或有效物质的含量可以在宽范围内变化。特别是使用聚合物组合物时,可以制备活性化合物浓缩物,其含有至少5重量%的活性化合物,例如5-50重量%,特别是5-20重量%,基于组合物的总重量计。
有利的是,本发明的组合物、特别是含水活性化合物组合物可以作为无溶剂或溶剂含量低的组合物配制,即挥发性组分在含水活性化合物组合物中的比例通常不超过10重量%,特别是不超过5重量%,特别不超过1重量%,基于组合物的总重量计。这里,挥发性组分是在大气压下的沸点低于200℃的组分。
在本发明的含水组合物中可以配制许多不同的活性化合物和有效物质。本发明的聚合物组合物特别适用于有机活性化合物、特别是分子量低于500道尔顿的低分子量活性化合物的配料。本发明的特别优选实施方案涉及用于保护作物的活性化合物配料,即除草剂、杀菌剂、杀线虫剂、杀螨剂、杀虫剂以及调节植物生长的活性化合物。
可以作为含水活性化合物组合物配制的本发明杀菌活性化合物的例子包括以下有机化合物:
-胺衍生物,例如杀螟丹、多果定、十二环吗啉、芬普福、苯锈啶、双辛胍胺、克热净、葚孢菌素、十三吗啉;
-苯胺基嘧啶,例如嘧霉胺、嘧菌胺或嘧菌环胺;
-抗菌素,例如环己酰亚胺、灰黄霉素、春雷霉素、纳他霉素、多抗霉素和链霉素和井岗霉素A;
-唑类,例如双苯三唑醇、糠菌唑、氰霜唑、环唑醇、苯醚甲环唑、二硝基康唑、氟环唑、嘧硫磷、腈苯唑、氟喹唑、氟硅唑、粉唑醇、麦穗宁、已唑醇、霉灵、imizalil、种菌唑、亚胺唑、叶菌唑、腈菌唑、戊菌唑、perfuazorate、丙环唑、咪鲜安、丙硫菌唑、硅氟唑、戊唑醇、氟醚唑、噻菌灵、三泰芬、三唑乙醇、特富灵、灭菌唑和2-丁氧基-6-碘-3-丙基苯并吡喃-4-酮、N,N-二甲基-3-(3-溴-6-氟-2-甲基吲哚-1-磺酰基)-[1,2,4]三唑-1-磺酰胺;
-2-甲氧基二苯酮,例如EP-A897 904中的式I,例如苯菌酮;
-二碳酰亚胺,例如异菌脲、甲菌利、腐霉利、乙烯菌核利;
-二硫代氨基甲酸酯,例如福美铁、代森钠、代森锰、代森锰锌、威百亩、代森联、丙森锌、代森福美锌、福美双、福美锌、代森锌;
-杂环化合物,例如敌菌灵、苯菌灵、啶酰菌胺、多菌灵、萎锈灵、氧化萎锈灵、氰霜唑、棉隆、二噻农、乙嘧酚、二甲嘧酚、唑酮菌、咪唑菌酮、氯苯嘧啶醇、麦穗宁、氟担菌宁、呋吡菌胺、稻瘟灵、灭锈胺、氟苯嘧啶醇、辛噻酮、氟吡菌胺、烯丙异噻唑、丙氧喹啉、啶斑肟、咯喹酮、喹氧灵、硅噻菌胺、噻菌灵、噻呋酰胺、甲基硫菌灵、噻酰菌胺、三环唑、嗪氨灵、3-[5-(4-氯苯基)-2,3-二甲基异唑烷-3-基]吡啶、和乙嘧酚磺酸酯;
-硝基苯基衍生物,例如乐杀螨、敌螨普、消螨通、硝基邻苯-异丙基(nitrophthal-isopropyl);
-苯基吡咯,例如拌种咯和咯菌腈;
-不属于任何其它类别的杀菌剂,例如噻二唑素-S-甲基、苯噻菌胺、氯环丙酰胺、百菌清、环氟菌胺、霜脲氰、哒菌清、双氯氰苗胺、万霉灵、敌瘟磷、噻唑菌胺、环酰菌胺、三苯基锡醋酸盐、氰菌胺、嘧菌腙、氟啶胺、福赛得、三乙膦酸铝、丙森锌、六氯苯、苯菌酮、宾得克利、霜霉威、四氯苯酞、toloclofos-methyl、无氯硝基苯、z草酰胺、稻瘟灵、氟吡菌胺(picobenzamid);氯环丙酰胺、双炔酰菌胺、N-(2-{4-[3-(4-氯苯基)丙-2-炔基氧基]-3-甲氧基苯基}乙基)-2-甲烷磺基氨基-3-甲基丁酰胺、N-(2-{4-[3-(4-氯苯基)丙-2-炔基氧基]-3-甲氧基苯基}乙基)-2-乙烷磺基氨基-3-甲基丁酰胺;呋吡菌胺、噻氟菌胺、吡噻菌胺、环酰菌胺、N-(2-氰基苯基)-3,4-二氯异噻唑-5-碳酰胺、flubenthiavalicarb、3-(4-氯苯基)-3-(2-异丙氧基羰基氨基-3-甲基丁酰基氨基)丙酸甲酯、{2-氯-5-[1-(6-甲基吡啶-2-基甲氧基亚氨基)乙基]苄基}氨基甲酸甲酯、甲基{2-氯-5-[1-(3-甲基苄基氧基亚氨基)乙基]苄基}氨基甲酸甲酯、磺菌胺、下式的酰胺:
其中
X是CHF2或CH3;和
R1、R2彼此独立地是卤素、甲基或卤代甲基,例如CF3;
●甲氧基丙烯酸酯类(strobilurins),如WO03/075663中的通式I、例如:嘧菌酯、醚菌胺、氟嘧菌酯、醚菌酯、苯氧菌胺、醚菌胺、啶氧菌酯、吡唑醚菌酯和肟菌酯;
●次磺酸衍生物,例如敌菌丹、克菌丹、苯氟磺胺、灭菌丹、甲苯氟磺胺;
●肉桂酰胺及其类似物,例如烯酰吗啉、flumetover、氟吗啉;
●6-芳基[1,2,4]三唑并[1,5-a]嘧啶,例如描述在WO98/46608、WO99/41255或WO03/004465中的式I化合物,例如5-氯-7-(4-甲基哌啶-1-基)-6-(2,4,6-三氟苯基)[1,2,4]三唑并[1,5-a]嘧啶;
●酰胺杀菌剂,例如cyclofenamid、和(Z)-N-[α-(环丙基甲氧基亚氨基)-2,3-二氟-6-(二氟甲氧基)苄基]-2-苯基乙酰胺。
可以作为本发明含水活性化合物组合物配制的除草剂的例子包括:
●1,3,4-噻二唑,例如丁噻咪草酮和三环噻草胺;
●酰胺,例如二丙烯草胺、新燕灵、溴丁酰草胺、草克乐、哌草丹、甲酚噻草胺、双苯酰草胺、乙氧苯草胺、草吡唑、蔓草磷、异噁草胺、吡唑草胺、庚酰草胺、萘草胺、戊炔草胺、敌稗;
●氨基磷酸,例如双丙氨膦、特克草、草铵膦、草甘膦、草硫膦;
●氨基三唑,例如杀草强、苯胺类、例如莎稗磷、苯噻草胺;
●N-酰苯胺,例如莎稗磷、苯噻草胺;
●芳基氧基链烷醇酸,例如2,4-D、2,4-DB、稗草胺、滴丙酸、2,4-滴丙酸、2,4,5-涕丙酸、氟草烟、MCPA、MCPB、2-甲-4-氯丙酸、2-甲-4-氯丙酸、敌草胺、敌草胺、绿草定;
●苯甲酸化合物,例如草灭平、麦草畏;
●苯并噻二嗪酮,例如灭草松;
●氨基甲酸酯,例如卡草胺、稗蓼灵、氯苯胺灵、甜安宁、甜菜宁、灭草猛;
●喹啉酸,例如二氯喹啉酸、喹草酸;
●二氯丙酸,例如茅草枯;
●二氢苯并呋喃,例如乙呋草黄;
●二氢呋喃-3-酮,例如呋草酮;
●二硝基苯胺,例如氟草胺、双丁乐灵、氨基乙氟灵、烯氟灵、氯氟灵、异丙乐灵、磺乐灵、安磺灵、二甲戊乐灵、氨基氟乐灵、环丙氟灵、氟乐灵、
●二硝基苯酚,例如溴酚肟、地乐酚、地乐酯、特乐酯、DNOC、minoterb-acetate;
●二苯基醚,例如三氟羧草醚、苯草醚、甲羧除草醚、草枯醚、枯莠隆、氯氟苯醚、氟甲消草醚、乙羧氟草醚、氟磺胺草醚、呋氧草醚、乳氟禾草灵、除草醚、三氟甲草醚、乙氧氟草醚;
●联吡啶,例如牧草快、野燕枯硫酸甲酯、敌草快、百草枯;
●咪唑,例如草特灵;
●咪唑烷酮,例如灭草唑、灭草烟、灭草喹、imazethabenz-methyl、咪唑乙烟酸、甲咪唑烟酸、甲氧咪草烟;
●环氧乙烷,例如灭草环;
●酚类,例如溴苯睛、辛酰碘苯腈;
●苯基乙酸,例如伐草克;
●苯基丙酸,例如燕麦酯;
●ppi-活性化合物、例如吡草酮、氟烯草酸、丙炔氟草胺、2-[4-氯-2-氟-5-[(1-甲基-2-丙炔基)氧基]苯基]-4,5,6,7-四氢-1H-异吲哚-1,3(2H)-二酮(flumipropyn)、1-异丙基-2-氯-5-(3,6-二氢-3-甲基-2,6-二氧代-4-三氟甲基-1(2H)-嘧啶基)苯甲酸酯(flupropacil)、苄草唑、磺酰唑草酮、噻二唑草胺;
●吡唑,例如吡氯草胺;
●哒嗪,例如杀草敏、马来酰肼、氟草敏、哒草特;
●吡啶羧酸,例如二氯吡啶酸、氟硫草定、百草枯、噻草定;
●嘧啶基醚,例如嘧啶苯甲酸、嘧草硫醚、KIH-2023、KIH-6127;
●磺酰胺,例如阔草清、磺草唑胺;
●三唑羧酰胺,例如1-(3-甲基苯基)-5-苯基-1H-1,2,4-三唑-3-甲酰胺(triazofenamide);
●尿嘧啶,例如除草定、环草定、特草定;
●另外,阔草克、呋草黄、地散灵、氟草黄、苯达松、抑草磷、唑草胺、氯酞酸二甲酯、环庚草醚、敌草腈、菌多杀、fluorbentranil、伏草胺、黄草伏、哌草磷、topramezone和调环酸;
●磺基脲,例如氨基嘧黄隆、四唑嘧磺隆、苄嘧磺隆、氯嘧磺隆、绿黄隆、醚磺隆、环丙嘧磺隆、胺苯磺隆、啶嘧磺隆、氯吡嘧磺隆、咪唑磺隆、甲磺隆、烟嘧磺隆、氟嘧磺隆、氟磺隆、吡嘧磺隆、砜嘧磺隆、甲嘧磺隆、噻吩磺隆、醚苯磺隆、苯磺隆、氟胺磺隆、三氟甲磺隆;
●环己烯酮类型的作物保护剂,例如禾草灭、烯草酮、环己烯草酮、环杀草、稀禾定和苯肟草酮。非常特别优选的环己烯酮类型的除草活性化合物是:徐草杀(参见AGROW、No.243、11.3.95、第21页、醌肟草)和2-(1-[2-{4-氯苯氧基}丙氧基亚氨基]丁基)-3-羟基-5-(2H-四氢硫代吡喃-3-基)-2-环己烯-1-酮、和磺酰基脲类型的除草活性化合物是:N-(((4-甲氧基-6-[三氟甲基]-1,3,5-三嗪-2-基)氨基)羰基)-2-(三氟甲基)苯磺酰胺。
可以作为本发明含水活性化合物组合物配制的杀虫剂的例子包括:
●有机(硫代)磷酸酯,例如乙酰甲胺磷、甲基吡噁磷、甲基谷硫磷、氯蜱硫磷、甲基毒死蜱、杀螟威、二嗪农、敌敌畏、甲基毒虫畏、水杨硫磷、百治磷、乐戈、乙拌磷、乙硫磷、EPN、杀螟松、倍硫磷、唑磷、马拉息昂、甲胺磷、杀扑磷、硫磷、速灭磷、久效磷、乙酰甲胺磷、对氧磷、对硫磷、稻丰散、伏杀硫磷、亚胺硫磷、大灭虫、甲拌磷、肟硫磷、甲基嘧啶磷、丙溴磷、普硫松、甲基嘧啶磷、吡唑硫磷、哒嗪硫磷、硫丙磷、三唑磷、三氯磷酸酯、杀虫畏、完灭硫磷;
●氨基甲酸酯,例如棉铃成、丙硫威、虫威、胺甲萘、克百威、丁硫克百威、双氧威、呋喃硫威、茚虫威、灭梭威、灭多威、杀线威、抗芽威、残杀威、硫双威、唑蚜威;
●拟除虫菊酯,例如丙烯菊酯、联苯菊酯、氟氯氰菊酯、乙氰菊酯、氢氯菊、苯氰菊酯、溴氰菊酯、氰戊菊酯、醚菊酯、甲氰菊酯、戊酸氰醚酯、氯氟氰菊酯、imoprothrin、高效氯氟氰菊酯、氯菊酯、丙炔菊酯、除虫菊素I、除虫菊素II、氟硅菊酯、氟胺氰菊酯、七氟菊酯、四溴菊酯、四氟苯菊酯、顺式氯氰菊酯、Z-氯氰菊酯、氯菊酯;
●节肢动物生长调节剂:a)甲壳质合成抑制剂,例如苯甲酰基脲、例如氟啶脲、灭蝇胺、除虫脲、氟螨脲、氟虫脲、氟铃脲、虱螨脲、双苯氟脲、氟苯脲、杀铃脲;噻嗪酮、苯虫醚、噻螨酮、环氧乙烷、布赐芬螨;b)蜕皮素拮抗剂,例如氯虫酰肼、甲氧虫酰肼、虫酰肼;c)保幼激素,例如吡丙醚、烯虫酯、双氧威;d)脂生物合成抑制剂,例如螺螨酯;
●新烟碱,例如氟啶虫酰胺、可尼丁、呋虫胺、吡虫啉、噻虫嗪、烯啶虫胺、硝虫噻嗪、啶虫脒、噻虫啉;
●不属于上述类别的其它杀虫剂,例如阿维菌素、灭螨醌、啶虫脒、双甲脒、印楝素、杀虫磺、联苯肼酯、杀螟丹、溴虫腈、杀螨脒、环丙氨嗪、杀螨隆、dinetofuran、苯虫醚、甲胺基阿维菌素、硫丹、乙虫清、喹螨醚、氟虫腈、伐虫脒、伐虫脒盐酸盐、γ-HCH、氟蚁腙、吡虫啉、茚虫成、异丙成、速灭威、达螨酮、吡蚜酮、多杀菌素、吡螨胺、噻虫嗪、杀虫环、啶虫丙醚、氟啶虫酰胺、fluacypyrim、密灭汀、螺甲螨酯、吡氟硫磷、NC512、唑虫酰胺、氟虫酰胺、双三氟虫脲、benclothiaz、pyrafluprole、pyriprole、磺酰苯胺、flufenerim、丁氟螨酯、灭螨醌、lepimectin、丙氟菊酯、四氟甲醚菊酯、脒腙、metaflumizone、N-R'-2,2-二卤-1-R”-环丙烷羧酰胺-2-(2,6-二氯-α,α,α-三氟-p-甲苯基)腙、N-R'-2,2-二(R)丙酰胺-2-(2,6-二氯-α,α,α-三氟-p-甲苯基)腙,其中卤素是氯或溴,R’是甲基或乙基,R”是氢或甲基,R是甲基或乙基,XMC和灭杀威,以及下式的化合物:
下式的氨基异噻唑:
其中
R=-CH2O-CH3或H,和
R’=-CF2CF2CF3;
下式的邻氨基苯甲酰胺:
其中R是C1-C4-烷基,例如甲基、乙基、异丙基或正丁基,
以及下式的化合物:
●N-苯基半咔唑,如EP-A462 456中的式I化合物,特别是下式V的化合物:
其中R11和R12彼此独立地是氢、卤素、CN、C1-C4-烷基、C1-C4-烷氧基、C1-C4-卤代烷基或C1-C4-卤代烷氧基,R13是C1-C4-烷氧基、C1-C4-卤代烷基或C1-C4-卤代烷氧基,例如式IV化合物,其中R11是3-CF3,R12是4-CN和R13是4-OCF3(氰氟虫胺)。
有用的生长调节剂例如是稻麦立、缩节胺、调环酸或赤霉素类。它们包括例如赤霉素GA1、GA3、GA4、GA5和GA7等,以及相应的外-16,17-二氢赤霉素,和它们的衍生物,例如与C1-C4-羧酸形成的酯。根据本发明优选外-16,17-二氢-GA513-乙酸酯,以及1-萘基乙酰胺、1-萘基乙酸、2-萘氧基乙酸、3-CPA、4-CPA、嘧啶醇、蒽醌、BAP、脱叶亚磷;脱叶磷、仲丁灵、整形醇、苯哒嗪钾、环丙酰胺酸、丁酰肼、麦草畏、敌草克、噻节因、杀螨醇、乙烯硅、乙烯磷、吲熟酯、涕丙酸、2,4,5-TP、增糖胺、呋嘧醇、粉唑醇、克热净、烯菌灵、吲哚丁酸、吲哚乙酸、karetazan、激动素、lactidichlor-ethyl、马来酰肼、伏草胺、萘草胺、多效唑、喹草酸、杀雄啉、特效烯、噻苯隆、三碘苯甲酸、抑芽唑、triazethan、脱叶磷、抗倒酯和优康唑。
本发明的优选实施方案涉及本发明聚合物组合物用于制备活性化合物组合物的用途,特别是杀菌剂的含水活性组合物,特别是甲氧基丙烯酸酯类、唑类和6-芳基三唑并[1,5a]嘧啶,如WO98/46608、WO99/41255或WO03/004465中所述的式I化合物,特别是对于式VI的活性化合物:
其中
Rx是基团NR14R15或直链或支化的C1-C8-烷基,其任选地被卤素、OH、C1-C4-烷氧基、苯基或C3-C6-环烷基取代;是C2-C6-链烯基、C3-C6-环烷基、C3-C6-环烯基、苯基或萘基,其中最后4种基团可以具有1、2、3或4个选自以下的取代基:卤素、OH、C1-C4-烷基、C1-C4-卤代烷氧基、C1-C4-烷氧基和C1-C4-卤代烷基;
R14、R15彼此独立地是氢、C1-C8-烷基、C1-C8-卤代烷基、C3-C10-环烷基、C3-C6-卤代环烷基、C2-C8-链烯基、C4-C10-烷二烯基、C2-C8-卤代链烯基、C3-C6-环烯基、C2-C8-卤代环烯基、C2-C8-炔基、C2-C8-卤代炔基或C3-C6-环炔基、
R14和R15与和它们连接的氮原子一起是5-8元杂环基,其经由N连接,并可以含有1、2或3个选自O、N和S的其它杂原子作为环成员,和/或可以携带一个或多个选自以下的取代基:卤素,C1-C6-烷基、C1-C6-卤代烷基、C2-C6-链烯基、C2-C6-卤代链烯基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C3-C6-链烯基氧基、C3-C6-卤代链烯基氧基、(外)-C1-C6-亚烷基和氧基-C1-C3-亚烷基氧基;
L选自卤素、氰基、C1-C6-烷基、C1-C4-卤代烷基、C1-C6-烷氧基、C1-C4-卤代烷氧基和C1-C6-烷氧基羰基;
L1是卤素、C1-C6-烷基或C1-C6-卤代烷基,特别是氟或氯;
X是卤素、C1-C4-烷基、氰基、C1-C4-烷氧基或C1-C4-卤代烷基,优选是卤素或甲基,特别是氯。
式VI化合物的例子是:
5-氯-7-(4-甲基哌啶-1-基)-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-a]嘧啶、
5-氯-7-(4-甲基哌嗪-1-基)-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-a]嘧啶、
5-氯-7-(吗啉-1-基)-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-a]嘧啶、
5-氯-7-(哌啶-1-基)-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-a]嘧啶、
5-氯-7-(吗啉-1-基)-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-a]嘧啶、
5-氯-7-(异丙基氨基)-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-a]嘧啶、
5-氯-7-(环戊基氨基)-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-a]嘧啶、
5-氯-7-(2,2,2-三氟乙基氨基)-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-a]嘧啶、
5-氯-7-(1,1,1-三氟丙烷-2-基氨基)-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-a]嘧啶、
5-氯-7-(3,3-二甲基丁烷-2-基氨基)-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-a]-嘧啶、
5-氯-7-(环己基甲基)-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-a]嘧啶、
5-氯-7-(环己基)-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-a]嘧啶、
5-氯-7-(2-甲基丁烷-3-基)-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-a]嘧啶、
5-氯-7-(3-甲基丙-1-基)-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-a]嘧啶,
5-氯-7-(4-甲基环己-1-基)-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-a]嘧啶、
5-氯-7-(己-3-基)-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-a]嘧啶、
5-氯-7-(2-甲基丁-1-基)-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-a]嘧啶、
5-氯-7-(3-甲基丁-1-基)-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-a]嘧啶、
5-氯-7-(1-甲基丙-1-基)-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-a]嘧啶、
5-甲基-7-(4-甲基哌啶-1-基)-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-a]嘧啶、
5-甲基-7-(4-甲基哌嗪-1-基)-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-a]嘧啶、
5-甲基-7-(吗啉-1-基)-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-a]嘧啶、
5-甲基-7-(哌啶-1-基)-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-a]嘧啶、
5-甲基-7-(吗啉-1-基)-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-a]嘧啶、
5-甲基-7-(异丙基氨基)-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-a]嘧啶、
5-甲基-7-(环戊基氨基)-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-a]嘧啶、
5-甲基-7-(2,2,2-三氟乙基氨基)-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-a]嘧啶、
5-甲基-7-(1,1,1-三氟丙-2-基氨基)-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-a]嘧啶、
5-甲基-7-(3,3-二甲基丁-2-基氨基)-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-a]-嘧啶、
5-甲基-7-(环己基甲基)-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-a]嘧啶、
5-甲基-7-(环己基)-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-a]嘧啶、
5-甲基-7-(2-甲基丁-3-基)-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-a]嘧啶,
5-甲基-7-(3-甲基丙-1-基)-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-a]嘧啶、
5-甲基-7-(4-甲基环己-1-基)-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-a]嘧啶、
5-甲基-7-(己-3-基)-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-a]嘧啶、
5-甲基-7-(2-甲基丁-1-基)-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-a]嘧啶,
5-甲基-7-(3-甲基丁-1-基)-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-a]嘧啶,和
5-甲基-7-(1-甲基丙-1-基)-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-a]嘧啶。
因此,本发明的优选实施方案也涉及本发明的聚合物组合物用于在水相中稳定或增溶杀菌剂的用途,所述杀菌剂特别是甲氧基丙烯酸酯类、唑类和6-芳基三唑并[1,5a]嘧啶,如WO98/46608、WO99/41255或WO03/004465的通式I所述,特别是通式VI的化合物。
本发明的另一个优选实施方案涉及本发明的聚合物组合物用于制备活性化合物组合物、特别是用于制备杀虫剂的活性化合物组合物的用途,所述杀虫剂特别是芳基吡咯,例如溴虫腈;拟除虫菊酯,例如联苯菊酯、氟氯氰菊酯、乙氰菊酯、氯氰菊酯、溴氰菊酯、氰戊菊酯、醚菊酯、甲氰菊酯、氰戊菊酯、氯氟氰菊酯、高效氯氟氰菊酯、氯菊酯、氟硅菊酯、氟胺氰菊酯、七氟菊酯、四溴菊酯、顺式氯氰菊酯、Z-氯氰菊酯和氯菊酯;新烟碱、和式V的半咔唑。
本发明的的优选实施方案因此还涉及本发明的聚合物组合物用于在水相中稳定或增溶杀虫剂的用途,所述杀虫剂特别是芳基吡咯、拟除虫菊酯、新烟碱和式V的半咔唑。
本发明的组合物还适用于制备活性化合物组合物,特别是药物活性化合物和前药的含水活性化合物组合物。这些包括苯二氮平、抗高血压药、维生素、细胞生长抑制剂-特别是泰素、麻醉药、抗精神病药、抗抑郁药、抗菌药、抗真菌素、杀菌剂、化疗药物、泌尿学用药、血小板聚集抑制剂、磺酰胺、解痉药、激素、免疫球蛋白、血清、甲状腺用药、精神药物、帕金森病治疗剂和其它抗多动症药、眼科用药、神经病用药、钙代谢调节剂、肌肉松弛剂、麻醉剂、降脂剂、抗胃肠病药、心血管药物、强心药、免疫治疗用药、调节肽和它们的抑制剂、催眠药、镇静剂、妇产科用药、抗痛风药物、纤维蛋白溶解药、酶产品和输送蛋白、酶抑制剂、呕吐药、血流刺激剂、利尿剂、诊断助剂、肾上腺皮质激素、胆素性药物、胆道治疗药、抗气喘药、抗支气管炎药、β受体阻断药、钙通道阻滞剂、ACE抑制剂、抗动脉硬化药、抗炎剂、抗聚集剂、抗低血压药、抗II型糖尿病药、抗高血压药、抗纤溶药、抗癫痫药、抗呕吐药、解毒剂、抗糖尿病药、抗心律失常药、抗贫血药、抗过敏药、驱绦药、镇痛药、催醒药、醛固酮拮抗药和减肥药。合适的药物活性化合物的例子特别是US2003/0157170的0105-0131段所提到的活性化合物。
本发明的聚合物组合物还适用于制备制剂,特别是化妆品活性化合物的含水制剂,尤其是化装油和脂肪的含水制剂,例如花生油、霍霍巴油、椰子油、杏仁油、橄榄油、棕榈油、蓖麻油、豆油或麦芽油;精油,例如矮松针油、熏衣草油、迷迭香油、冷杉油、松针油、桉油、椒样薄荷油、鼠尾草油、佛手柑油、松节油、香蜂草油、香紫苏油、杜松子油、柠檬油、茴香油、小豆蔻油、椒样薄荷油、樟脑油等,或这些油的混合物。
此外,本发明的聚合物组合物还适用于制备制剂,特别是食品添加剂的含水制剂,例如水不溶性维生素和前维生素,例如维生素A、乙酸维生素A、维生素D、维生素E;生育酚衍生物,例如乙酸生育酚酯,和维生素K。
因此,本发明的聚合物组合物也适用于在水相中稳定上述活性化合物。
可以作为本发明含水活性化合物组合物配制的有效物质的例子是:
染料:例如DE-A102 45 209中所述的染料,以及根据Color Index归类为分散染料和溶剂染料的化合物,它们也称为分散染料。合适的分散染料的综述可以在Ullmanns Enzyklopdie der technischen Chemie[Ullmann's工业化学百科全书]、第4版、第10卷、155-165页中找到(也参见第7卷第585页起.-蒽醌染料;第8卷第244页起-偶氮染料;第9卷第313页起-喹酞酮染料)。该文献和其中提到的化合物引入本文供参考。根据本发明合适的分散染料和溶剂染料包括具有不同发色团的不同类型的染料,例如蒽醌染料、单偶氮和二偶氮染料、喹酞酮、次甲基和氮杂次甲基染料、萘二酰胺染料、萘醌染料和硝基染料。根据本发明合适的分散染料的例子是以下ColorIndex列表的分散染料:C.I.分散黄1-228、C.I.分散橙1-148、C.I.分散红1-349、C.I.分散紫1-97、C.I.分散蓝1-349、C.I.分散绿1-9、C.I.分散棕1-21、C.I.分散黑1-36。根据本发明合适的溶剂染料的例子是以下Color Index列表的化合物:C.I.溶剂黄2-191、C.I.溶剂橙1-113、C.I.溶剂红1-248、C.I.溶剂紫2-61、C.I.溶剂蓝2-143、C.I.溶剂绿1-35、C.I.溶剂棕1-63、C.I.溶剂黑3-50。根据本发明合适的其它染料的例子是萘、蒽、苝、三并苯、四并苯,以及二酮基吡咯并吡咯染料,紫环酮染料,香豆素染料,异吲哚啉和异吲哚烷酮染料,卟啉染料,酞菁染料和萘菁染料;和
UV吸收剂:特别是下述a至g类化合物:
a)4,4-二芳基丁二烯,
b)肉桂酸酯,
c)苯并三唑
d)羟基二苯酮,
e)二苯基氰基丙烯酸酯,
f)草酰胺,
g)2-苯基-1,3,5-三嗪。
组a)的4,4-二芳基丁二烯例如包括式A的化合物:
这些化合物从EP-A-916 335得知。取代基R10和/或R11优选是C1-C8-烷基和C5-C8-环烷基。
组b)的肉桂酸酯包括例如4-甲氧基肉桂酸2-异戊基酯、4-甲氧基肉桂酸2-乙基己基酯、α-甲氧基羰基肉桂酸甲基酯、α-氰基-β-甲基-p-甲氧基肉桂酸甲基酯,α-氰基-β-甲基-p-甲氧基肉桂酸丁基酯,和α-甲氧基羰基-p-甲氧基肉桂酸甲基酯。
组c)的苯并三唑包括例如2-(2’-羟基苯基)苯并三唑、例如2-(2’-羟基-5’-甲基苯基)苯并三唑、2-(3’,5’-二叔丁基-2’-羟基苯基)苯并三唑、2-(5’-叔丁基-2’-羟基苯基)苯并三唑、2-(2’-羟基-5’-(1,1,3,3-四甲基丁基)苯基)苯并三唑、2-(3’,5’-二叔丁基-2’-羟基苯基)-5-氯苯并三唑、2-(3’-叔丁基-2’-羟基-5’-甲基苯基)-5-氯苯并三唑、2-(3’-仲-丁基-5’-叔丁基-2’-羟基苯基)苯并三唑、2-(2’-羟基-4’-辛基氧基苯基)苯并三唑、2’-(3’,5'-二叔戊基-2’-羟基苯基)苯并三唑、2-(3’,5’-二(α,α-二甲基苄基)-2’-羟基苯基)苯并三唑、2-(3’-叔丁基-2’-羟基-5’-(2-辛氧基羰基乙基)苯基)-5-氯苯并三唑、2-(3’-叔丁基-5’-[2-(2-乙基己氧基)羰基乙基]-2’-羟基苯基)-5-氯苯并三唑、2-(3’-叔丁基-2’-羟基-5’-(2-甲氧基羰基乙基)苯基)-5-氯苯并三唑、2-(3’-叔丁基-2’-羟基-5’-(2-甲氧基羰基乙基)苯基)苯并三唑、2-(3’-叔丁基-2’-羟基-5’-(2-辛氧基羰基乙基)苯基)苯并三唑、2-(3’-叔丁基-5’-[2-(2-乙基己氧基)羰基乙基]-2’-羟基苯基)苯并三唑、2-(3’-十二烷基-2’-羟基-5’-甲基苯基)苯并三唑和2-(3’-叔丁基-2’-羟基-5’-(2-异辛氧基羰基乙基)苯基苯并三唑、2,2’-亚甲基二[4-(1,1,3,3-四甲基丁基)-6-苯并三唑-2-基苯酚];2-[3’-叔丁基-5’-(2-甲氧基羰基乙基)-2’-羟基苯基]-2H-苯并三唑与聚乙二醇300的酯化产物;[R-CH2CH2-COO(CH2)3]2,其中R=3’-叔丁基-4’-羟基-5'-2H-苯并三唑-2-基苯基以及它们的混合物。
组d)的羟基二苯酮包括例如2-羟基二苯酮,例如2-羟基-4-甲氧基二苯酮、2,2’-二羟基-4-甲氧基二苯酮、2,4-二羟基二苯酮、2,2’,4,4’-四羟基二苯酮、2,2’-二羟基-4,4'-二甲氧基二苯酮、2-羟基-4-(2-乙基己氧基)二苯酮、2-羟基-4-(正辛氧基)二苯酮、2-羟基-4-甲氧基-4’-甲基二苯酮、2-羟基-3-羧基二苯酮、2-羟基-4-甲氧基二苯酮-5-磺酸及其钙盐、2,2’-二羟基-4,4’-二甲氧基二苯酮-5,5’-二磺酸及其钙盐。
组e)的二苯基氰基丙烯酸酯包括例如2-氰基-3,3-二苯基丙烯酸乙基酯,其例如从商业以商品名Uvinul3035从BASF AG、Ludwigshafen获得;2-氰基-3,3-二苯基丙烯酸2-乙基己基酯,其例如从商业作为Uvinul3039从BASF AG、Ludwigshafen获得,和1,3-二[(2’-氰基-3’,3’-二苯基丙烯酰氧基)氧基]-2,2-二{[2’-氰基-3’,3’-二苯基丙烯酰氧基]氧基}甲基}丙烷,其可以从商业以商品名Uvinul3030从BASF AG、Ludwigshafen获得。
组f)的草酰胺包括例如4,4'-二辛氧基N,N'-草酰二苯胺、2,2’-二乙氧基草酰二苯胺、2,2’-二辛氧基-5,5’-二叔丁草酰二苯胺、2,2’-双十二烷氧基-5,5’-二叔丁草酰二苯胺、2-乙氧基-2’-乙基草酰二苯胺、N,N'-二(3-二甲基氨基丙基)草酰胺、2-乙氧基-5-叔丁基-2’-乙草酰二苯胺及其与2-乙氧基-2’-乙基-5,4’-二叔丁草酰二苯胺的混合物,以及邻-、对-甲氧基-二取代的草酰二苯胺,以及邻-和对-乙氧基-二取代的草酰二苯胺的混合物。
组g)的2-苯基-1,3,5-三嗪包括例如2-(2-羟基苯基)-1,3,5-三嗪,例如2,4,6-三(2-羟基-4-辛氧基苯基)-1,3,5-三嗪、2-(2-羟基-4-辛氧基苯基)-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪、2-(2,4-二羟基苯基)-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪、2,4-二(2-羟基-4-丙氧基苯基)-6-(2,4-二甲基苯基)-1,3,5-三嗪、2-(2-羟基-4-辛氧基苯基)-4,6-二(4-甲基苯基)-1,3,5-三嗪、2-(2-羟基-4-十二烷氧基苯基)-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪、2-(2-羟基-4-十三烷氧基苯基)-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪、2-[2-羟基-4-(2-羟基-3-丁氧基丙氧基)苯基]-4,6-二(2,4-二甲基)-1,3,5-三嗪、2-[2-羟基-4-(2-羟基-3-辛氧基丙氧基)苯基]-4,6-二(2,4-二甲基)-1,3,5-三嗪、2-[4-(十二烷氧基/十三烷氧基-2-羟基丙氧基)-2-羟基苯基]-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪、2-[2-羟基-4-(2-羟基-3-十二烷氧基丙氧基)苯基]-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪、2-(2-羟基-4-己氧基苯基)-4,6-二苯基-1,3,5-三嗪、2-(2-羟基-4-甲氧基苯基)-4,6-二苯基-1,3,5-三嗪、2,4,6-三[2-羟基-4-(3-丁氧基-2-羟基丙氧基)苯基]-1,3,5-三嗪和2-(2-羟基苯基)-4-(4-甲氧基苯基)-6-苯基-1,3,5-三嗪。
除了上述组分之外,本发明的含水活性化合物组合物也可以含有常规的表面活性物质和其它添加剂。表面活性物质包括表面活性剂、分散剂和湿润剂。其它添加剂包括特别是增稠剂、消泡剂、防腐剂、防冻剂、稳定剂等。
阴离子、阳离子、非离子和两亲性表面活性剂一般是合适的,其包括聚合物表面活性剂和在疏水基团中具有杂原子的表面活性剂。
阴离子表面活性剂包括例如羧酸盐、特别是脂肪酸的碱金属、碱土金属和铵盐,例如硬脂酸钾,它们通常称为皂;谷氨酸酰基酯,例如月桂酰基肌氨酸钠;酒石酸盐;甲基纤维素;磷酸烷基酯、特别是单-和二磷酸的烷基酯;硫酸盐、特别是烷基硫酸盐和烷基醚硫酸盐;磺酸盐、以及烷基磺酸盐和烷基芳基磺酸盐、特别是芳基磺酸和烷基取代的芳基磺酸、烷基苯磺酸的碱金属、碱土金属和铵盐、例如木素-和苯酚磺酸、萘-和二丁基萘磺酸、或十二烷基苯磺酸盐、烷基萘磺酸盐、烷基甲基酯磺酸盐、磺化萘及其衍生物与甲醛的缩合物,萘磺酸、苯酚-和/或苯酚磺酸与甲醛或与甲醛和脲的缩合物,单-或二烷基磺基琥珀酸盐;以及蛋白水解物和木质素亚硫酸盐废液。上述磺酸有利地以其中性形式或合适的话以碱性盐的形式使用。
非离子表面活性剂包括例如:
-脂肪醇聚氧乙烯酯,例如月桂醇聚氧乙烯醚乙酸酯,
-烷基聚氧乙烯醚和烷基聚氧丙烯醚,例如异十三烷基醇和脂肪醇和脂肪醇聚氧乙烯醚,
-烷基芳基醇聚氧乙烯醚,例如辛基酚聚氧乙烯醚,
-烷氧基化的动物和/或植物脂肪和/或油,例如玉米油乙氧基化物、蓖麻油乙氧基化物、牛油脂肪乙氧基化物,
-甘油酯,例如甘油单硬脂酸酯,
-脂肪醇烷氧基化物和羰基合成醇烷氧基化物、特别是以下类型RO-(R18O)r(R19O)sR20,其中R18和R19彼此独立地=C2H4、C3H6、C4H8,R20=H或C1-C12-烷基,R=C3-C30-烷基或C6-C30-链烯基,r和s彼此独立地是0-50,其中之一不是0,例如异十三烷醇和油基醇聚氧乙烯醚,
-烷基酚烷氧基化物,例如乙氧基化异辛基酚、辛基苯酚或壬基苯酚、三丁基苯酚聚氧乙烯醚,
-脂肪胺烷氧基化物、脂肪酸酰胺烷氧基化物和脂肪酸二乙醇酰胺烷氧基化物,特别是它们的乙氧基化物、
-糖表面活性剂,山梨醇酯,例如脂肪酸失水山梨醇酯(单油酸失水山梨醇酯,三硬脂酸失水山梨醇酯)、聚氧乙烯失水山梨醇脂肪酸酯,烷基聚苷、N-烷基葡糖酰胺,
-烷基甲基亚砜,
-烷基二甲基氧化膦,例如四癸基二甲基氧化膦。
两亲性表面活性剂包括例如磺基甜菜碱、羧基甜菜碱和烷基二甲基氧化胺,例如四癸基二甲基氧化胺。
可以提到的其它表面活性剂例如是全氟表面活性剂,有机硅表面活性剂,磷脂,例如卵磷脂或化学改性的卵磷脂,氨基酸表面活性剂,例如N-月桂酰基谷氨酸酯。
除非另有说明,上述表面活性剂的烷基链是具有通常8-20个碳原子的直链或支化基团。
在一个实施方案中,本发明的含水活性化合物组合物含有不超过10重量%、优选不超过5重量%、特别不超过3重量%、例如0.01-5重量%或0.1-3重量%的常规表面活性物质,在每种情况下基于活性化合物和聚合物组合物的总量计。在这种情况下,常规表面活性物质优选是基于该组合物总重量计的不超过5重量%、特别是不超过3重量%、例如0.01-5重量%或0.1-3重量%。
但是,根据应用,可以有利地将本发明的活性化合物组合物与表面活性物质一起配制。在这种情况下,常规表面活性物质的比例一般是0.5-30重量%,特别是1-20重量%,基于活性化合物和聚合物组合物的总量计;或是0.2-20重量%,特别是0.5-15重量%,基于配制的组合物的总重量计。
尽管本发明组合物的一个优点是挥发性有机化合物的含量低,但是一些应用可能希望本发明组合物与有机溶剂、油和脂肪、优选溶剂或油和脂肪一起使用,它们是环境友好的或可生物降解的,例如上述水混溶性溶剂或仅仅在非常有限的程度上与水混溶的溶剂、油或脂肪,或不能与水混溶,例如与一种或多种下述物质混溶:
-石蜡油、芳烃以及芳烃的混合物,例如二甲苯,Solvesso100、150或200等,
-酚和烷基酚,例如苯酚、氢醌、壬基酚等,
-具有不超过4个碳原子的酮,例如环己酮、异佛尔酮、紫环酮、乙酰苯、乙酰萘,
-具有不超过4个碳原子的醇,例如乙酰基化羊毛脂醇、鲸醋醇、1-癸醇、1-庚醇、1-己醇、异十八醇、异丙醇、油醇、苯甲醇,
-羧酸酯,例如己二酸二烷基酯,例如己二酸二(2-乙基己基)酯;邻苯二甲酸二烷基酯,例如邻苯二甲酸二(2-乙基己基)酯;乙酸烷基酯(也包括支化烷基)、例如乙酸乙基酯和乙酰乙酸乙基酯;硬脂酸酯,例如硬脂酸丁基酯、甘油单硬脂酸酯;柠檬酸酯,例如柠檬酸乙酰基三丁基酯;还有辛酸鲸醋基酯、油酸甲基酯、对羟基苯甲酸甲酯、四癸酸甲酯、对-羟基苯甲酸丙基酯、苯甲酸甲酯;乳酸酯,例如乳酸异丙基酯、乳酸丁基酯和乳酸2-乙基己基酯,
-植物油,例如棕榈油、蓖麻子油、蓖麻油及其衍生物,例如氧化的叶子油、鳕鱼肝油、玉米油、豆油、亚麻子油、橄榄油、花生油、红花油、芝麻油、葡萄油、丁香罗勒油、杏仁油、姜油、除萜香叶油、橙油、迷迭香油、澳洲坚果油、洋葱油、橘子油、松油、向日葵油,
-氢化植物油,例如氢化棕榈油、氢化蓖麻子油、氢化豆油,
-动物油,例如猪油、鱼油,
-中链至长链脂肪酸的二烷基酰胺,例如Hallcomides,和
-植物油酯,例如蓖麻子油甲基酯。
合适的增稠剂是能向配料赋予假塑性流动行为的化合物,即在静态下的高粘度和在搅拌状态下的低粘度。在这方面,可以提到例如多糖或有机片状矿物,例如Xanthan Gum(Kelzan,来自Kelco)、Rhodopol23(Rhone Poulenc)或Veegum(来自R.T.Vanderbilt)或Attaclay(来自Engelhardt)、其中优选的是Xanthan Gum。
合适的防冻剂是有机多元醇,例如乙二醇、丙二醇或甘油。它们通常的用量是不超过10重量%,基于活性化合物组合物的总重量计,使得不超过所需含量的挥发性化合物。在本发明的一个实施方案中,与之不同的挥发性化合物的比例是优选不超过1重量%,特别不超过1000ppm。
如果合适的话,本发明的活性化合物组合物可以含有1-5重量%的缓冲剂,基于制备的配料的总量计,从而调节pH,所用的缓冲剂的用量和类型取决于一种或多种活性化合物的化学性质。缓冲剂的例子是弱的无机或有机酸的碱金属盐,例如磷酸、硼酸、乙酸、丙酸、柠檬酸、富马酸、酒石酸、草酸和琥珀酸。
本发明还提供固体活性化合物组合物,其含有至少一种上述两亲性聚合物组合物和至少一种活性化合物和/或有效物质,所述活性化合物和/或有效物质细分在聚合物组合物中,在25℃/1013毫巴下在水中的溶解度小于10g/l,并且通常选自上述活性化合物。本发明的固体活性化合物组合物可以分散在水中,得到本发明的含水活性化合物组合物。惊奇的是,以此方式获得的含水活性化合物组合物的特征也在于所述活性化合物非常细地分散在连续水相中,其中得到上述给出的粒径,且基本不超过该粒径。
所述固体活性化合物组合物中,活性化合物和/或有效物质与两亲性聚合物组合物的重量比通常是1∶10至3∶1,特别是1∶5至2∶1。
本发明的固体活性化合物组合物可以例如通过将本发明的含水活性化合物组合物干燥、通过将活性化合物溶解在活性化合物熔体中或通过将活性化合物和两亲性聚合物组合物溶解在溶剂中并除去溶剂而获得。
优选通过干燥含水活性化合物组合物而获得的固体活性化合物组合物。它们是通常以颗粒形式获得的固体材料。根据干燥方法的类型,获得粉末或颗粒。
对于干燥,通过常规方法除去挥发性组分,即水和任何溶剂或挥发性基质。可以提到的方法特别是常规的对流干燥方法,例如喷雾干燥、流化床干燥、气动干燥、研磨干燥、带式干燥以及这些干燥方法的混合形式;接触干燥方法,例如鼓干燥、腔室或小室干燥、薄层干燥,在桨式干燥器或在旋转干燥器中干燥,冷冻干燥和辐射干燥。这些方法是本领域技术人员熟知的,例如来自C.M.van′t Land″Industrial Drying Equipment″Marcel Decker,Inc.1991;O.Kriseher、W.Kast、K.Krll,″Trocknungstechnik″[干燥技术],1-3卷,Springer-Verlag1978、1959和1989;K.Masters、“Spraydrying Handbook”,Longman Scientific andTechnical;H.Uhlmann/Lothar Mrl,“Wirbelschicht/Sprühgranulat”[流化床/喷雾颗粒],Springer-Verlag2000。含水活性化合物组合物优选在低于聚合物玻璃化温度的温度下干燥,特别是-20至100℃。
根据存在的活性化合物或有效物质的性质,本发明的活性化合物或有效物质可以按照本身与常规配料中相应活性化合物或有效物质相当的方式使用。例如,含有至少一种杀虫、杀螨或杀线虫活性化合物的活性化合物组合物可以用于控制有害的昆虫、螨或线虫。如果本发明的活性化合物组合物含有至少一种杀菌活性化合物,它们可以用于控制有害的真菌。如果本发明的活性化合物组合物含有除草活性化合物,它们可以用于控制杂草等。
根据活性化合物的性质,本发明的组合物特别用于保护植物抵抗有害有机体的攻击,例如昆虫、螨、线虫,或用于保护植物抵抗病原真菌等的攻击,用于处理种子,或用于保护材料,例如用于保护木素纤维素材料(例如木材)抵抗害虫的攻击,例如破坏木材的甲虫、白蚁、蚂蚁等,或抵抗使木材脱色或破坏木材的真菌的攻击。
当然,本发明的组合物也可以用于化妆品或药物或工业应用中。
下面通过实施例详细描述本发明。
I.聚合物组合物的制备:
I.1制备实施例1
a)将4000g的甲基封端的聚氧乙烯(数均分子量为2000道尔顿,KOH值为33mg/g固体物质)和573g的可商业获得的六亚甲基二异氰酸酯的缩二脲(NCO含量为22%,在23℃下的粘度为4.0Pa.s)溶解在4573g的四氢呋喃中,将该溶液在60℃加热。加入0.08g的二月桂酸二丁锡,并将该反应混合物在相同温度下搅拌直到混合物的NCO含量降低到0.46%。
b)将1500g四氢呋喃进行回流加热。在2小时内,同时加入含有1400.1g甲基丙烯酸2-(二甲基氨基)乙基酯、850.6g甲基丙烯酸甲酯和632.3g甲基丙烯酸正丁酯的进料1a和含有1500g四氢呋喃(THF)、15.59g偶氮二异丁腈(AIBN)和58.42g巯基乙醇的进料1b,并将该混合物保持在回流下直到单体的量降低到小于初始量的3重量%(通过气相色谱检测)。然后加入来自步骤a的6859g反应混合物,并将该混合物于65℃搅拌,直到NCO含量降低到0%。该混合物然后用8573g四氢呋喃稀释。
c)在30分钟内向来自步骤b的聚合物溶液中加入15kg水,然后减压蒸馏出四氢呋喃。这得到30重量%的聚合物组合物的水分散液,平均粒径为244nm(通过动态光散射在pH=7下检测)。
I.2制备实施例2:
a)将1500g四氢呋喃进行回流加热。在2小时内,同时加入含有1112g2-乙烯基吡啶、1059.1g甲基丙烯酸甲酯和751.9g甲基丙烯酸正丁酯的进料1a和含有1500g四氢呋喃(THF)、18.59g偶氮二异丁腈(AIBN)和58.42g巯基乙醇的进料1b,并将该混合物保持在回流下直到单体的量降低到小于初始量的3重量%(通过气相色谱检测)。然后加入来自实施例1步骤a的6859g反应混合物,并将该混合物于65℃搅拌,直到NCO含量降低到0%。该混合物然后用8573g四氢呋喃稀释。
b)在30分钟内向以此方式制备的聚合物溶液中加入15kg水,然后减压蒸馏出四氢呋喃。这得到30重量%的聚合物组合物的水分散液,平均粒径为196nm(通过动态光散射在pH=7下检测)。
I.3制备实施例3:
a)将1444g四氢呋喃(THF)进行回流加热。在2小时内,同时加入含有1631.6g甲基丙烯酸3-(N,N-二甲基氨基)丙基酯(DMAPMA)、719.8g的甲基丙烯酸甲酯(MMA)和460.7g的丙烯酸2-苯氧基乙基酯(POEA)的进料1a和含有1444gTHF、18.57g偶氮二异丁腈(AIBN)和58.36g巯基乙醇的进料1b,并将该混合物保持在回流下直到单体的量降低到小于初始量的3重量%(通过气相色谱检测)。然后加入来自实施例1步骤a的6859g反应混合物,并将该混合物于65℃搅拌,直到NCO含量降低到0%。该混合物然后用7760gTHF稀释。
b)在30分钟内向以此方式制备的聚合物溶液中加入15kg水,然后减压蒸馏出四氢呋喃。这得到30重量%的聚合物组合物的水分散液,平均粒径为<20nm(通过动态光散射在pH=7下检测)。
II.制备本发明的含水活性化合物制剂
II.1分析:
这里所述的粘度是按照DIN53019-2在旋转粘度计中测定的。
平均粒径是通过静态光散射法使用含水活性化合物配料的稀释样品在20℃检测的。
为了检测储存稳定性,将含水活性化合物组合物在室温下储存2周,于54℃储存2周和于5℃储存2周。此外,活性化合物组合物被冷冻和融化。如果在这些条件都没有观察到沉积或乳化液分层,则样品是储存稳定的。
II.2一般制备工序:
1.增溶方法(液体活性化合物和活性化合物熔体):
将10g活性化合物搅拌入90g的含有30g聚合物的聚合物组合物水分散液中,温度是活性化合物作为低粘度熔体存在的温度(例如60-80℃)。根据聚合物溶液和活性化合物熔体的粘度,使用磁力搅拌器或Ultraturrax进行搅拌。达到增溶平衡所需要的时间取决于聚合物组合物和活性化合物,并可以是数秒,也可以是数小时。当活性化合物均匀分布在混合物中并且即使当引入更多能量时也没有观察到粒径变化时,达到增溶平衡。
2.转相方法:
将13.33g的15%浓度的液体或固体活性化合物在THF中的溶液与20g在四氢呋喃中的30%聚合物溶液混合。然后在搅拌下加入水,随后通过蒸馏除去有机溶剂。水的添加量使得所得的含水配料含有10重量%的活性化合物和30重量%的聚合物。
3.固溶体的方法:
将0.g聚合物组合物(聚合物含量>95重量%)和0.1g活性化合物溶解在约20ml有机溶剂(优选四氢呋喃、二甲基甲酰胺)中。然后完全除去溶剂(例如在旋转蒸发器上),使得疏水活性化合物和聚合物组合物的固溶体保留下来。加入缓冲的水溶液(100ml,pH6.8),并将混合物搅拌24小时。在过滤之后,该溶液用HPLC(UV检测器)分析,并确定活性化合物的浓度。
4.喷嘴沉淀:
使用两个泵,在混合装置中经由混合喷嘴混合30%聚合物水分散液和40%的活性化合物/THF溶液。聚合物分散液的流速是12kg/h,THF溶液的流速是3kg/h,使得总流速是15kg/h。混合装置相当于在“Handbook ofIndustrial Crystallization”(A.S.Myerson、1993 Butterworth-Heinemann、第139页、ISBN 0-7506-9155-7)中描述的装置。这得到浅黄色的乳状悬浮液,其含有8%活性化合物和24%聚合物。随后通过蒸馏除去THF和一部分水,从而形成含有10%活性化合物和30%聚合物的含水纳米颗粒配料。
II.3配料实施例1:通过转相方法(一般工序2)用制备实施例1b的聚合物组合物增溶唑菌胺酯
将唑菌胺酯在THF中的13.33g的15%浓度溶液与来自实施例1g的在THF中的20g聚合物溶液(30%浓度)混合。在搅拌下,然后加入水,在减压下除去THF。选择水的量,使得所得的含水配料含有10重量%的活性化合物和30重量%的聚合物组合物。
所得的活性化合物组合物是均匀的,目测基本透明的,并能用水稀释(去离子水和10°d[德国硬度]的水)且不会发生活性化合物的任何沉降或结晶。
在表1中列出的其它活性化合物也可以按照类似的方式配制。
表1
活性化合物 | 在蒸馏水中的溶解度[mg/l] |
氧唑菌 | 6.63 |
啶酰菌胺 | 4.6 |
唑菌胺酯 | 2.4 |
叶菌唑 | 15 |
α-氯氰菊酯 | 0.01 |
II.4配料实施例2:来自配料实施例1的固体活性化合物配料的再分散
将唑菌胺酯的40%浓度的含水液体配料(配料实施例2)进行冷冻干燥。所得的固体配料在数月内是稳定的(目测,没有观察到活性化合物晶体),并能用水稀释(去离子水和10°d的水)且不会发生活性化合物的任何沉降或结晶。
II.5配料实施例3:通过固溶体方法(一般工序3)用制备实施例1b的聚合物组合物增溶唑菌胺酯
使用固溶体方法,用来自制备实施例1b的聚合物组合物配制唑菌胺酯。形成的固溶体能稳定至少几个月(目测,没有观察到活性化合物晶体),并能用水稀释(去离子水和10°d的水)且不会发生活性化合物的任何沉降或结晶。
II.6配料实施例4:通过增溶方法(一般工序1)用制备实施例1b的聚合物组合物增溶唑菌胺酯
所得的活性化合物组合物是均匀的,目测基本透明的,至少几个月内对沉降稳定的,并能用水稀释(去离子水和10°d的水)且不会发生活性化合物的任何沉降或结晶。
II.7配料实施例5:通过转相方法(一般工序2)用制备实施例2b的聚合物组合物增溶叶菌唑
将叶菌唑在THF中的13.33g的15%浓度溶液与来自实施例1b的在THF中的20g聚合物溶液(30%浓度)混合。在搅拌下,然后加入水,在减压下除去THF。选择水的量,使得所得的含水配料含有10重量%的活性化合物和30重量%的聚合物组合物。
所得的活性化合物组合物是均匀的,目测基本透明的,并能用水稀释(去离子水和10°d的水)且不会发生活性化合物的任何沉降或结晶。
在表1中列出的其它活性化合物也可以按照类似的方式配制。
II.8配料实施例6:从配料实施例5制备的固体配料的再分散
将唑菌胺酯的40%浓度的液体配料(配料实施例5)进行冷冻干燥。所得的固体配料在数月内是稳定的,并能用水稀释(去离子水和10°d的水)且不会发生活性化合物的任何沉降或结晶。
II.9配料实施例7:通过固溶体方法(一般工序3)用制备实施例2b的聚合物组合物增溶唑菌胺酯
使用固溶体方法,用来自制备实施例2b的聚合物组合物配制唑菌胺酯。形成的固溶体能稳定至少几个月(目测,没有观察到活性化合物晶体),并能用水稀释(去离子水和10°d的水)且不会发生活性化合物的任何沉降或结晶。
II.10配料实施例8:通过增溶方法(一般工序1)用制备实施例2b的聚合物组合物增溶唑菌胺酯
所得的活性化合物组合物是均匀的,目测基本透明的,至少几个月内对沉降稳定的,并能用水稀释(去离子水和10°d的水)且不会发生活性化合物的任何沉降或结晶。
II.11配料实施例9:通过转相方法(一般工序2)用制备实施例2b的聚合物组合物增溶叶菌唑
将叶菌唑在THF中的13.33g的15%浓度溶液与来自实施例1b的在TH中的20g聚合物溶液F(30%浓度)和非离子表面活性剂(参见表3)混合。在搅拌下,然后加入水,在减压下除去THF。选择水的量,使得所得的含水配料含有10重量%的活性化合物和30重量%的聚合物组合物。
表3
配料 | 表面活性剂 | 表面活性剂的量[g] |
9a | A | 1g |
9b | A | 6g |
9c | B | 1g |
9d | B | 6g |
A:乙氧基化异十三醇,乙氧基度为8
B:乙氧基化C9-C11-链烷醇,乙氧基度为3
所得的活性化合物组合物是均匀的,目测基本透明的,并能用水稀释(去离子水和10°d的水)且不会发生活性化合物的任何沉降或结晶。
III.应用实验
III.1评价杀菌活性
根据以下工序在温室中比较来自配料实施例5(叶菌唑)的含水活性化合物组合物和含有相同活性化合物(叶菌唑)的商业配料在抵抗小麦植物上的褐锈病(Puccinia recondita)方面的活性:
抵抗由褐锈病引起的小麦褐锈病的治疗活性
活性化合物叶菌唑作为64ppm活性化合物浓度的原料溶液制备,然后用水稀释到下面的活性化合物浓度(表4)。
栽培品种″Kanzler″的盆载麦种子的叶子用褐锈病的孢子悬浮液培育。然后将盆在具有高大气湿度(90-95%)和20-22℃的室中放置24小时。在此期间,孢子发芽,芽管穿入叶子组织中。第二天,用具有上述活性化合物浓度的水悬浮液喷到被感染的植物的流出点上。所述悬浮液已经如上所述制备。在已经干燥喷涂涂层之后,将实验植物在温室中在20-22℃的温度和65-70%相对湿度下培育7天。然后检测在叶子上锈菌的发展程度。
生物实验结果列在表4中。结果显示聚合物稳定的活性化合物具有与商业产品相同水平的杀菌活性。
表4
感染[%] | 感染[%] | 感染[%] | 感染[%] | |
施用率[ppm] | 配料实施例5 | 配料实施例9c | 配料实施例9d | 常规配料1) |
64 | 0 | 0 | 0 | 0 |
32 | 0 | 0 | 0 | 3 |
16 | 6 | 6 | 0 | 10 |
8 | 15 | 37 | 14 | 35 |
4 | 77 | 63 | 63 | 70 |
1)常规配料的组成:
在1l的含水配料中:
200g/l的叶菌唑
70g/l的防冻剂
30g/l的非离子分散剂
20g/l的阴离子分散剂
2g/l的增稠剂
2g/l的抗微生物剂
Claims (32)
1.一种聚合物组合物,通过使以下组分反应而获得:
a)至少一种聚合物P1,其带有对异氰酸酯基团有反应性的官能团R1,并且由烯属不饱和单体M1构成,其中单体M1含有基于单体M1总量计的多于20重量%的单体M1a,所述单体M1a具有选自以下的至少一个官能团FG:叔氨基、亚氨基、羧酰胺基、腈基、内酰胺基、酮基、醛基、脲基、聚醚基、羧基、磺酰基、羟基磺酰基和磺酰胺基,
b)至少一种聚C2-C4亚烷基醚P2,其带有对异氰酸酯基团有反应性的官能团R2,
c)至少一种化合物V,其带有异氰酸酯基团,并且关于异氰酸酯基团的官能度是至少1.5,
其中聚合物P1与聚C2-C4亚烷基醚P2的重量比P1∶P2是在1∶10至10∶1的范围内,
其中聚合物P1包含:
a1)基于单体M1的总量计,>20重量%至90重量%的单烯属不饱和单体M1a;
a2)基于单体M1的总量计,10重量%至<80重量%的单体M1b,其于25℃在水中的溶解度小于30g/l,并且不同于单体M1a;和
a3)基于单体M1的总量计,0-20重量%的烯属不饱和单体M1c,其与单体M1a和M1b不同,
其中单体M1b选自式I的单体:
其中
X是氧或基团N-R4,
R1是C1-C20烷基、C5-C10环烷基、苯基、苯基-C1-C4烷基或苯氧基-C1-C4烷基;
R2是氢或C1-C4烷基;
R3是氢或C1-C4烷基;和
R4是氢或C1-C4烷基。
2.根据权利要求1的聚合物组合物,其中聚合物P1具有关于官能团R1的官能度F1为0.3-3。
3.根据权利要求1的聚合物组合物,其中单体M1a选自以下物质:
-单烯属不饱和C3-C8单羧酸的酰胺和C1-C4烷氧基烷基酰胺;
-单烯属不饱和腈;
-脂族或芳族羧酸的N-乙烯基酰胺;
-具有5-7个环原子的N-乙烯基内酰胺;
-乙烯基取代的氮杂芳族化合物;
-带有脲基的单烯属不饱和单体;
-具有醛基或酮基的单烯属不饱和单体;和
-具有伯、仲或叔氨基的单烯属不饱和单体。
4.根据权利要求3的聚合物组合物,其中单体M1a选自脂环族羧酸的N-乙烯基酰胺。
5.根据权利要求1的聚合物组合物,其中聚合物P1的数均分子量是500-20000道尔顿。
6.根据权利要求1的聚合物组合物,其中聚C2-C4亚烷基醚P2具有至少70重量%的环氧乙烷基团。
7.根据权利要求1的聚合物组合物,其中聚C2-C4亚烷基醚P2具有关于官能团R2的官能度F2为0.5-3.0。
8.根据权利要求1的聚合物组合物,其中聚C2-C4亚烷基醚P2的数均分子量是500-20000道尔顿。
9.一种制备根据权利要求1的聚合物组合物的方法,该方法包括使以下组分反应:
i)至少一种聚合物P1和
ii)至少一种聚C2-C4亚烷基醚P2与
iii)至少一种化合物V,其含有异氰酸酯基团,并具有关于异氰酸酯基团的官能度是至少1.5。
10.根据权利要求9的方法,其中聚合物P1和聚C2-C4亚烷基醚P2接连与化合物V反应。
11.根据权利要求9的方法,其中聚合物P1和聚C2-C4亚烷基醚P2在一个步骤中与化合物V反应。
12.根据权利要求1的聚合物组合物用于在含水介质中稳定活性化合物和/或有效物质的用途,所述活性化合物和/或有效物质在水中于25℃/1013毫巴下的溶解度小于10g/l,其中活性化合物是选自除草剂、杀菌剂、杀虫剂、调节植物生长的化合物、药物和化妆品上的活性物质,其中有效物质是选自染料和UV吸收剂。
13.根据权利要求12的用途,其中杀虫剂是选自杀线虫剂和杀螨剂。
14.根据权利要求1的聚合物组合物用于制备活性化合物和/或有效物质的配料的用途,所述活性化合物和/或有效物质在水中于25℃/1013毫巴下的溶解度小于10g/l,其中活性化合物是选自除草剂、杀菌剂、杀虫剂、调节植物生长的化合物、药物和化妆品上的活性物质,其中有效物质是选自染料和UV吸收剂。
15.根据权利要求14的用途,其中杀虫剂是选自杀线虫剂和杀螨剂。
16.根据权利要求1的聚合物组合物用于制备活性化合物和有效物质的含水配料的用途,所述活性化合物和/或有效物质在水中于25℃/1013毫巴下的溶解度小于10g/l,其中活性化合物是选自除草剂、杀菌剂、杀虫剂、调节植物生长的化合物、药物和化妆品上的活性物质,其中有效物质是选自染料和UV吸收剂。
17.根据权利要求16的用途,其中杀虫剂是选自杀线虫剂和杀螨剂。
18.一种活性化合物组合物,其含有:至少一种活性化合物和/或有效物质,其在水中于25℃/1013毫巴下的溶解度小于10g/l;和至少一种根据权利要求1的聚合物组合物,其中活性化合物是选自除草剂、杀菌剂、杀虫剂、调节植物生长的化合物、药物和化妆品上的活性物质,其中有效物质是选自染料和UV吸收剂。
19.根据权利要求18的活性化合物组合物,其中杀虫剂是选自杀线虫剂、杀螨剂。
20.一种含水的活性化合物组合物,其含有作为连续相的含水介质、溶解或分散在连续相中的至少一种活性化合物和/或有效物质以及至少一种根据权利要求1的聚合物组合物,所述活性化合物和/或有效物质在水中于25℃/1013毫巴下的溶解度小于10g/l,其中活性化合物是选自除草剂、杀菌剂、杀虫剂、调节植物生长的化合物、药物和化妆品上的活性物质,其中有效物质是选自染料和UV吸收剂。
21.根据权利要求20的活性化合物组合物,其中杀虫剂是选自杀线虫剂和杀螨剂。
22.根据权利要求20的活性化合物组合物,其中在水相中所含的活性化合物和有效物质形成聚集体或颗粒,其平均粒径通过动态光散射检测为不超过300nm。
23.根据权利要求18的活性化合物组合物,其含有重量比为1∶10至3∶1的活性化合物和/或有效物质和聚合物组合物。
24.根据权利要求18的活性化合物组合物,其中所述组合物具有含量小于10重量%的挥发性有机化合物,基于该组合物的总重量计。
25.一种制备根据权利要求18的活性化合物组合物的方法,该方法包括制备含有聚合物组合物和至少一种活性化合物和/或有效物质的均匀的非水性混合物。
26.一种制备根据权利要求20的含水活性化合物组合物的方法,该方法包括:
a)制备含有聚合物组合物和活性化合物和/或有效物质的均匀的非水性混合物,和
b)用水分散所得的混合物。
27.一种制备根据权利要求20的含水活性化合物组合物的方法,该方法包括:
a)制备活性化合物和/或有效物质和如果合适的聚合物组合物在沸点低于水的有机溶剂中的溶液,和
b)将活性化合物和/或有效物质的溶液与水或含共聚物的水溶液混合,和
c)除去有机溶剂。
28.一种制备根据权利要求20的含水活性化合物组合物的方法,该方法包括在比活性化合物的熔点高的温度下将活性化合物和/或有效物质引入聚合物组合物的水溶液中。
29.一种固体活性化合物组合物,其含有至少一种根据权利要求1的聚合物组合物和至少一种活性化合物和/或有效物质,所述活性化合物和/或有效物质细分散在聚合物组合物中,并具有在25℃和1013毫巴下在水中的溶解度小于10g/l,其中活性化合物是选自除草剂、杀菌剂、杀虫剂、调节植物生长的化合物、药物和化妆品上的活性物质,其中有效物质是选自染料和UV吸收剂。
30.根据权利要求29的固体活性化合物组合物,其中杀虫剂是选自杀线虫剂和杀螨剂。
31.根据权利要求29的固体活性化合物组合物,其含有重量比为1∶10至3∶1的活性化合物和/或有效物质和聚合物组合物。
32.一种固体活性化合物组合物,其通过将根据权利要求20的液体含水活性化合物组合物干燥而获得。
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DE102005005931 | 2005-02-09 | ||
DE102005005931.7 | 2005-02-09 | ||
PCT/EP2006/001106 WO2006084680A1 (de) | 2005-02-09 | 2006-02-08 | Polymerzusammensetzungen und ihre verwendung zur herstellung von wirk- oder effektstoffzusammensetzungen |
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US (1) | US20080167189A1 (zh) |
EP (1) | EP1851262A1 (zh) |
JP (1) | JP4635056B2 (zh) |
KR (1) | KR20070110288A (zh) |
CN (1) | CN101151291B (zh) |
AR (1) | AR053126A1 (zh) |
AU (1) | AU2006212414A1 (zh) |
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EA (1) | EA014939B1 (zh) |
IL (1) | IL185096A0 (zh) |
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AR049208A1 (es) * | 2004-06-08 | 2006-07-05 | Basf Ag | Composiciones polimericas anfifilicas y su uso |
JP5507455B2 (ja) * | 2007-07-09 | 2014-05-28 | ビーエーエスエフ ソシエタス・ヨーロピア | 油溶性有機uv吸収剤の濃縮水性製品形態 |
US7655597B1 (en) | 2009-08-03 | 2010-02-02 | Specialty Fertilizer Products, Llc | Pesticide compositions including polymeric adjuvants |
TR201901665T4 (tr) * | 2015-03-09 | 2019-02-21 | Basf Se | Soğuk ortamda mükemmel esnekli̇k gösteren poli̇üretan döküm parçalar. |
CN111602658A (zh) * | 2020-05-18 | 2020-09-01 | 安徽启威生物科技有限公司 | 一种可降解的杀菌剂及其制备方法 |
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EP0742238A1 (de) * | 1995-05-11 | 1996-11-13 | BASF Magnetics GmbH | Als Dispergierharze geeignete polymere Massen |
EP0790265A1 (en) * | 1996-02-15 | 1997-08-20 | SANYO CHEMICAL INDUSTRIES, Ltd. | Sealing material for cable and cable using the same |
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CR9289A (es) | 2007-10-01 |
IL185096A0 (en) | 2007-12-03 |
BRPI0606926A2 (pt) | 2009-12-01 |
US20080167189A1 (en) | 2008-07-10 |
JP4635056B2 (ja) | 2011-02-16 |
CA2596818A1 (en) | 2006-08-17 |
AU2006212414A1 (en) | 2006-08-17 |
CN101151291A (zh) | 2008-03-26 |
WO2006084680A1 (de) | 2006-08-17 |
AR053126A1 (es) | 2007-04-25 |
EA200701622A1 (ru) | 2008-02-28 |
MX2007009076A (es) | 2007-09-11 |
EP1851262A1 (de) | 2007-11-07 |
JP2008530259A (ja) | 2008-08-07 |
KR20070110288A (ko) | 2007-11-16 |
EA014939B1 (ru) | 2011-04-29 |
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