CN102264464A - 制备含有有效物质的微粒的方法 - Google Patents
制备含有有效物质的微粒的方法 Download PDFInfo
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- CN102264464A CN102264464A CN2009801521770A CN200980152177A CN102264464A CN 102264464 A CN102264464 A CN 102264464A CN 2009801521770 A CN2009801521770 A CN 2009801521770A CN 200980152177 A CN200980152177 A CN 200980152177A CN 102264464 A CN102264464 A CN 102264464A
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- polyisocyanates
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Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
- B01J13/02—Making microcapsules or microballoons
- B01J13/06—Making microcapsules or microballoons by phase separation
- B01J13/14—Polymerisation; cross-linking
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Cosmetics (AREA)
- Detergent Compositions (AREA)
- Medicinal Preparation (AREA)
- Graft Or Block Polymers (AREA)
- Polyurethanes Or Polyureas (AREA)
- Pretreatment Of Seeds And Plants (AREA)
- General Preparation And Processing Of Foods (AREA)
- Manufacturing Of Micro-Capsules (AREA)
- Fertilizers (AREA)
- Polymerisation Methods In General (AREA)
Abstract
本发明涉及一种制备含有有效物质的微粒M的方法,所述方法包括:A)在含有酶、有效物质和聚酯单体的反相微乳液中通过酶催聚酯合成形成微粒A的粗悬浮液;和B)使选自烯属不饱和单体、多异氰酸酯和/或多环氧化物的壁单体在微粒A的粗悬浮液中聚合。此外,本发明涉及微粒M,其是通过本发明方法获得的,还涉及含有微粒M的农业化学配料。本发明还涉及根据本发明制备的微粒M作为组分用于以下物质中的用途:着色剂、化妆品、药物、杀微生物剂、农药、肥料,用于食品或动物饲料的添加剂,或用于聚合物、纸、织物、皮革、洗涤剂和清洁剂中的助剂。最后,本发明还涉及一种抵抗不需要的植物生长的方法,涉及抵抗不需要的昆虫或螨虫对植物的侵害的方法和/或抵抗植物病菌的方法,以及涉及用所述农业化学配料处理的种子。
Description
本发明涉及一种制备含有有效化合物的微粒M的方法,包括:A)在含有酶、有效化合物和聚酯单体的反相微乳液中通过酶催聚酯合成形成微粒A的粗悬浮液;和B)使选自烯属不饱和单体、多异氰酸酯和多环氧化物的壁单体在微粒A的粗悬浮液中聚合。此外,本发明涉及微粒M,其可以通过本发明方法获得,还涉及含有微粒M的农业化学配料。另外,本发明涉及根据本发明制备的微粒M作为组分用于以下物质中的用途:着色剂、化妆品、药物、杀微生物剂、植物保护剂、肥料,用于食品或动物饲料的添加剂,或用于聚合物、纸、织物、皮革、洗涤剂或清洁剂中的助剂。最后,本发明还涉及一种抵抗不需要的植物生长的方法,涉及抵抗在植物上的不需要的昆虫或螨虫的方法和/或抵抗植物病菌的方法,以及涉及用所述农业化学配料处理的种子。
优选特征与其它优选特征的组合也包含在本发明范围内。
微粒是在大多数不同的方案中已知的,根据胶囊壁的不可透过性而用于非常不同的目的。例如,它们用于保护芯材料,这些芯材料仅仅通过胶囊包裹层的有选择性机械破坏而释放,例如用于复印纸的着色剂前体或用于包封的芳族物质。基于明胶、聚氨酯树脂、蜜胺/甲醛树脂和聚丙烯酸酯树脂的胶囊包裹层材料在这些应用领域中是已知的。对用于植物的壁材料或作为芯材料的药物活性化合物有其它要求,其中重要的是胶囊包裹层具有空隙率,这使得有可能控制释放和有目的地输送活性化合物。除了通过化学方法制备的胶囊之外,在这里也知道机械/物理制备方法。
已经知道化学或物理方法一般用于制备微粒。采用物理方法,已溶解的聚合物通常被施用到要包封的材料上,并通过物理方法被转化成固体胶囊壁,例如喷雾干燥或溶剂去除。采用化学方法,固体胶囊壁是通过化学反应在要包封的材料上形成的,例如通过单体的聚合。用于形成固体微粒的另外的物理阶段是不必要的。
含有聚酯的微粒和它们的制备方法是一般已知的。这些微粒可以从用于胶囊包裹层的聚合物进料制备。因此,EP 1421990描述了一种制备微粒的方法,其中分散在多元醇中的聚酯用作为有效化合物的分散在多元醇中的酶乳化。US 4,637,905描述了一种制备尺寸为1-2000微米的微粒的方法,其中制备了具有作为有效化合物的蛋白质的聚乳酸分散体,蒸发一部分溶剂并且最后将浓缩的分散体加入用于包封有效化合物的第三溶剂中。WO 2002/069922描述了具有含有氧化还原酶的含水芯和含有聚酯的包裹层的微粒。此制备是如下进行的:用溶解在有机溶剂中的聚酯乳化酶的水溶液,然后将初级乳液引入含水溶剂中并随后除去有机溶剂。DE102005007374描述了芯-壳型的纳米粒子。疏水性和生物相容性的聚合物定义为壳。此聚合物是例如聚丙烯酸酯、聚环氧化物、聚氨酯或聚酯。被壳层聚合物包封的活性化合物定义为芯。制备是通过自由基聚合、加成聚合、缩聚或者酶催或阴离子聚合进行的。没有描述方法的细节或实施例。
PCT/EP2008/054702描述了一种制备微胶囊的方法,所述微胶囊含有含有效化合物的胶囊芯和含聚合物的胶囊包裹层,所述方法包括通过在反相微乳液中的单体的酶催聚合反应形成胶囊包裹层。
这些已知方法的缺点是例如形成微粒的聚合物是单独地通过聚合制备的,微粒不足够稳定,或者有效化合物的释放速率不能控制。
本发明的目的是提供一种改进的制备含有有效化合物的微粒的方法。尤其是,本发明的目的是提供一种这样的方法,其中含聚酯的微粒可以具有胶囊结构的改进稳定性。本发明的另一个方面是在温和反应条件下制备上述微粒,从而即使敏感的有效化合物也能被包封。另一个方面是有效化合物的随后释放能通过制备方法和单体组成来控制。
此目的是通过一种制备含有有效化合物的微粒M的方法实现的,此方法包括:A)在含有酶、有效化合物和聚酯单体的反相微乳液中通过酶催聚酯合成形成微粒A的粗悬浮液;和B)使选自烯属不饱和单体、多异氰酸酯和多环氧化物的壁单体在微粒A的粗悬浮液中聚合。
微粒M的总体一般是通过本发明方法制备的。本发明方法通常获得相同或相似形状的微粒。根据本发明制备的微粒可以具有任何形状。优选,它们是基本上球形结构的,例如优选是球形的。
根据本发明制备的含有有效化合物的微粒M通常具有胶囊或基质粒子的结构,优选具有胶囊的结构。胶囊一般是从含有聚合物的胶囊包裹层和含有有效化合物的胶囊芯形成的。基质粒子一般是从含有聚合物的粒子芯形成的,其中有效化合物以最终分布的形式存在。
根据本发明,也应当获得含有至少一种胶囊包裹层和至少一种胶囊芯的胶囊。因此,胶囊可以例如显示出一种胶囊芯和两种胶囊包裹层。相似地,胶囊可以例如显示数种胶囊芯,例如两种胶囊芯,它们中的一种接着另一种,或者一种在另一种之内;和一种胶囊包裹层,例如两种胶囊包裹层,它们中的一种接着另一种,或者一种在另一种之内。优选,胶囊含有一种胶囊包裹层和一种胶囊芯。胶囊包裹层的厚度可以在宽范围内变化。此厚度一般是胶囊半径的0.1-90%,优选0.5-20%(通过光/电子显微镜或光散射检测)。
微粒M的平均直径(作为Z均值通过对微粒的1重量%水分散液进行光散射来检测,所述水分散液是通过用水稀释微粒悬浮液并且在合适时分离有机相而获得的)可以在宽范围内变化。此平均直径一般大于0.1微米,优选大于0.6微米,特别优选大于0.8微米。直径优选在0.1-2000微米的范围内,优选0.6-1000微米,尤其是0.8-800微米。如果对于微粒需要较高的机械稳定性,则在较低范围内的直径是优选的。在较高范围内的直径是优选的,从而在尽量少的壁材料中包装尽可能多的胶囊内容物。
微粒M通常含有至少一种有效化合物。有效化合物在这方面通常以固体、已溶解、已乳化或已分散的形式存在于粒子芯中或存在于胶囊芯中。在一个优选实施方案中,胶囊芯含有至少一种有效化合物和至少一种惰性化合物,其优选是液体。在本发明方法中存在的所有化合物例如适合作为惰性化合物:分散剂,极性和/或非极性液体,水或具有催化作用的酶。胶囊芯尤其含有至少一种有效化合物和至少一种极性溶剂。粒子芯或胶囊芯也可以含有不完全聚合的单体。根据一个优选实施方案,胶囊芯含有至少极性液体,这形成反相微乳液的分散相。
根据本发明,在本发明制备微粒M的方法中使用能催化聚酯单体聚合的酶。对于酶的描述,使用由“生物化学和分子生物学国际联合命名委员会(NC-IUBMB)”开发的EC类的酶。显然可以使用单独的水解酶或不同水解酶的混合物。也可以以游离和/或固定的形式使用水解酶。
合适的水解酶[EC 3.x.x.x]的例子是酯酶(EC 3.1.x.x),蛋白酶(EC.3.4.x.x),能与除肽键之外的其它C-N键反应的水解酶(EC.3.5.x.x)或能与酸酐反应的(EC.3.6.x.x)。根据本发明,有利地尤其使用羧基酯酶[EC3.1.1.1]、脂酶[3.1.1.3]或角质酶[EC3.1.1.47]。例子是来自以下的脂酶:无色杆菌属(Achromobacter sp.),曲霉菌属(Aspergillus sp.),假丝酵母菌属(Candida sp.),南极洲假丝酵母(Candida antarctica),毛霉菌属(Mucor sp.),青霉菌属(Penicillium sp.),林生地霉菌属(Geotricum sp.),根霉菌属(Rhizopus sp.),伯克霍尔德氏菌属(Burkholderia sp.),假单胞菌属(Pseudomonas sp.),洋葱假单胞菌(Pseudomonas cepacia),嗜热真菌属(Thermomyces sp.),猪胰腺或麦芽;以及来自以下的羧基酯酶:芽孢杆菌属(Bacillus sp.),假单胞菌属(Pseudomonas sp.),伯克霍尔德氏菌属(Burkholderia sp.),毛霉菌属(Mucor sp.),酵母菌属(Saccharomyces sp.),根霉菌属(Rhizopus sp.),热厌氧菌属(Thermoanaerobium sp.),猪肝或马肝。优选使用来自以下的游离或固定形式的脂酶:洋葱假单胞菌(Pseudomonas cepacia),伯克霍尔德氏菌(Burkholderia platarii)或南极洲假丝酵母类型B(Candida antarcticatype B)(例如435,来自Novozymes A/S,丹麦)。
酶的总用量一般是0.001-40重量%,经常是0.1-15重量%,通常是0.5-10重量%,在每种情况下基于聚酯单体的总量计。此量取决于所用酶的纯度。工业或固定化的酶的用量一般高于经提纯的酶的用量。本领域技术人员也将根据催化剂的量而知道反应怎样快地达到终点。
合适的聚酯单体是例如羟基羧酸单体、二醇化合物或二酸化合物,尤其是羟基羧酸化合物。在前单体的组合也是可能的,二醇化合物和二酸化合物的组合是优选的。
在一个优选实施方案中,聚酯单体与引发剂单体组合,引发剂单体是氢酸化合物,例如羟基官能或氨基官能的化合物或水。合适的引发剂单体是羟基羧酸化合物、二醇化合物或二酸化合物。引发剂单体优选是下述二醇化合物,尤其是乙二醇、1,4-丁二醇、甘油、山梨醇、单糖、二糖、多糖或羟基官能的树枝状聚酯,其基于2,2-二羟甲基丙酸(产品,从Perstorp获得)。
作为羟基羧酸化合物,可以使用具有至少一个游离醇羟基和至少一个游离羧酸基的游离羟基羧酸,它们的C1-C5烷基酯和/或它们的内酯。可以提到例如乙醇酸,D-、L-或D,L-乳酸,6-羟基己烷酸(6-羟基己酸)、3-羟基丁酸、3-羟基戊酸、3-羟基己酸,或它们的环状衍生物,例如乙交酯(1,4-二烷-2,5-二酮),D-、L-或D,L-丙交酯(3,6-二甲基-1,4-二烷-2,5-二酮),ε-己内酯,β-丁内酯,γ-丁内酯,ω-十二烷交酯(氧杂环十三烷-2-酮)、ω-十一烷交酯(氧杂环十二烷-2-酮)或ω-十五烷交酯(氧杂环十六烷-2-酮)。双内酯或三内酯也适合作为内酯,其含有两个或三个内酯基团。例如,可以使用(2,2’-二(ε-己内酯-4-基)丙烷。双内酯可以例如是根据Palmgren等在Journal of Polymer Science A,1997,35,1635-1649中所述合成。碳酸的酯(碳酸酯)也是合适的,尤其是直链和环状的脂族碳酸酯,优选碳酸的C1-C8烷基酯,特别是碳酸三亚甲基酯。不能与相应酶反应的碳酸酯不适合作为单体,例如碳酸亚丙酯。作为羟基羧酸化合物,也可以使用硫代羧酸及其酯,以及与上述羟基羧酸化合物类似的硫代内酯。显然,也可以使用不同羟基羧酸化合物的混合物。优选的羟基羧酸化合物是内酯,尤其是C2-C18亚烷基内酯,非常特别优选ε-己内酯。
原则上,作为二羧酸化合物,可以使用所有的C2-C40脂族的、C3-C20脂环族的、芳族或杂芳族的化合物,其具有至少两个羧酸基团(羧基;-COOH)或其衍生物。上述二羧酸的C1-C10烷基酯,优选甲基酯、乙基酯、正丙基酯或异丙基酯、单酯或二酯,以及相应的二羧酸酐,尤其适合作为衍生物。二羧酸化合物的例子是乙烷二酸(草酸)、丙烷二酸(丙二酸)、丁烷二酸(琥珀酸)、戊烷二酸(戊二酸)、己烷二酸(己二酸)、庚烷二酸(庚二酸)、辛烷二酸(辛二酸)、壬烷二酸(壬二酸)、癸烷二酸(癸二酸)、十一烷二酸、十二烷二酸、十三烷二酸(巴西基酸)、C32二聚脂肪酸、苯-1,2-二羧酸(邻苯二甲酸)、苯-1,3-二羧酸(间苯二甲酸)或苯-1,4-二羧酸(对苯二甲酸),它们的甲基酯,例如乙二酸二甲酯,戊二酸二甲酯,丁二酸二甲酯,戊二酸二甲酯,己二酸二甲酯,庚二酸二甲酯,辛二酸二甲酯,壬二酸二甲酯,癸二酸二甲酯,十一烷二酸二甲酯,十二烷二酸二甲酯,十三烷二酸二甲酯,C32二聚脂肪酸二甲酯,邻苯二甲酸二甲酯,间苯二甲酸二甲酯,或对苯二甲酸二甲酯,以及它们的酸酐,例如丁烷二羧酸酐、戊烷二羧酸酐或邻苯二甲酸酐。显然,也可以使用上述二羧酸化合物的混合物。具有至少两个游离羧基的低聚酯和聚酯,尤其是被羧基封端的低聚酯和聚酯,也可以用做二羧酸组分。也可以使用多羧酸的酯,例如柠檬酸和丁四羧酸。优选使用游离的二羧酸,尤其是C4-C36脂族二羧酸,尤其是丁二酸、己二酸、癸二酸或十二烷二酸或它们的相应的二甲基酯和二乙基酯。
作为二醇化合物,可以使用具有2-18个、优选4-14个碳原子的支化或直链烷烃,具有5-20个碳原子的环烷烃,或含有至少两个醇基团的芳族化合物。合适的烷二醇的例子是乙二醇、1,2-丙二醇、1,3-丙二醇、1,2-丁二醇、1,4-丁二醇、1,5-戊二醇、1,6-己二醇、1,7-庚二醇、1,8-辛二醇、1,9-壬二醇、1,10-癸二醇、1,11-十一烷二醇、1,12-十二烷二醇、1,13-十三烷二醇、2,4-二甲基-2-乙基-1,3-己二醇、2,2-二甲基-1,3-丙二醇(新戊二醇)、2-乙基-2-丁基-1,3-丙二醇、2-乙基-2-异丁基-1,3-丙二醇或2,2,4-三甲基-1,6-己二醇。尤其合适的是乙二醇、1,3-丙二醇、1,4-丁二醇、2,2-二甲基-1,3-丙二醇、1,6-己二醇或1,12-十二烷二醇。环烷二醇的例子是1,2-环戊二醇、1,3-环戊二醇、1,2-环己二醇、1,3-环己二醇、1,4-环己二醇、1,2-环己烷二甲醇(1,2-二羟甲基环己烷)、1,3-环己烷二甲醇(1,3-二羟甲基环己烷)、1,4-环己烷二甲醇(1,4-二羟甲基环己烷)或2,2,4,4-四甲基-1,3-环丁烷二醇。合适的芳族二醇的例子是1,4-二羟基苯、1,3-二羟基苯、1,2-二羟基苯、双酚A(2,2-二(4-羟基苯基)丙烷)、1,3-二羟基萘、1,5-二羟基萘或1,7-二羟基萘。但是,作为二醇化合物,也可以使用例如聚醚二醇,例如二甘醇、三甘醇、聚乙二醇(具有多于4个环氧乙烷单元)、丙二醇、双丙甘醇、三丙甘醇、聚丙二醇(具有多于4个环氧丙烷单元)以及聚四氢呋喃(poly-THF),尤其是二甘醇、三甘醇和聚乙二醇(具有多于4个环氧乙烷单元)。具有通常在200-10000g/mol、优选600-5000g/mol范围内的数均分子量(Mn)的化合物用做聚四氢呋喃、聚乙二醇或聚丙二醇。具有至少两个游离醇基的低聚酯和聚酯、优选被二羟基封端的低聚酯和聚酯,也是合适的。也合适的是树枝状体,其显示至少两个游离的伯醇基或仲醇基。也合适的是聚碳酸酯,其显示至少两个游离的伯醇基或仲醇基。合适的具有多于两个醇基的二醇化合物的其它例子是甘油、山梨醇、三羟甲基丙烷、季戊四醇、单糖,例如果糖、葡萄糖或甘露糖,二糖例如蔗糖,低聚糖以及它们的取代产物,或纤维素衍生物,例如乙酸酯。也可以使用与上述二醇化合物类似的二硫醇作为二醇化合物。当然也可以使用上述二醇化合物或二硫醇的混合物。优选的二醇是脂族链烷二醇和聚醚二醇,特别优选具有2-18个碳原子的直链和支化的脂族链烷二醇,尤其是乙二醇、1,4-丁二醇、1,6-己二醇、山梨醇和新戊二醇。
直链、支化或交联的聚酯可以从上述单体制备,这取决于是否使用双官能单体或更高级的官能单体。
聚酯单体一般在阶段A)中在反应混合物中的存在量是0.1-20重量%,优选0.5-10重量%,尤其是1-5重量%,基于总物料计。在一个优选实施方案中,至少一种内酯的存在量是0.1-20重量%,优选0.5-10重量%,尤其是1-5重量%,基于在阶段A)中的总物料计。
分散剂可以根据本发明方法使用。这些可以原则上是保护胶体、乳化剂或它们的混合物。在此方面,显然选择乳化剂和/或保护胶体,使得它们尤其与所用的酶相容且不会使酶失活。
聚合可以在保护胶体的存在下进行,如果合适的话可以除了乳化剂之外使用。它们一般具有大于500g/mol的平均摩尔质量Mw,优选大于1000g/mol。保护胶体的例子是聚乙烯醇、纤维素衍生物,例如羧甲基纤维素,聚乙烯基吡咯烷酮,聚乙二醇,乙酸乙烯酯和/或丙酸乙烯酯在聚乙二醇上的接枝聚合物,在一端或两端被烷基、羧基或氨基封端的聚乙二醇,聚(二烯丙基二甲基氯化铵)和/或多糖,例如尤其是水溶性淀粉或淀粉衍生物。
通常完全使用乳化剂作为分散剂。通常使用具有一般小于1000g/mol相对分子量的乳化剂,与保护胶体不同。它们可以是阴离子性、阳离子性或非离子性的。在使用表面活性物质的混合物的情况下,各组分必须显然彼此相容,这在有疑问的情况下可以从一些初级实验确定。一般,阴离子乳化剂是彼此相容的,并且与非离子乳化剂相容的。这也适用于阳离子乳化剂,而阴离子和阳离子乳化剂一般是彼此不相容的。
聚合反应可以在合适时也在细分的水不溶性无机乳化剂的存在下进行(“拣选乳化剂”),例如硫酸钡。
常规的非离子乳化剂是例如乙氧基化的单-、二-和三-烷基酚(乙氧基化度是3-50,烷基是C4-C12)和乙氧基化脂肪醇(乙氧基化度是3-80,烷基是C8-C36)。例子是来自BASF SE的A品牌(C12-C14脂肪醇乙氧基化物,乙氧基化度是3-8),AO品牌(C13-C15羰基合成醇乙氧基化物,乙氧基化度是3-30),AT品牌(C16-C18脂肪醇乙氧基化物,乙氧基化度是11-80),ON品牌(C10羰基合成醇乙氧基化物,乙氧基化度是3-11)和TO品牌(C13羰基合成醇乙氧基化物,乙氧基化度是3-20)。
常规的阴离子乳化剂是例如硫酸烷基酯的碱金属盐和铵盐(烷基是C8-C12),乙氧基化链烷醇的硫酸单酯的碱金属盐和铵盐(乙氧基化度是4-30,烷基是C12-C18),和乙氧基化烷基酚的碱金属盐和铵盐(乙氧基化度是3-50,烷基是C4-C12),烷基磺酸的碱金属盐和铵盐(烷基是C12-C18),以及烷基芳基磺酸的碱金属盐和铵盐(烷基是C9-C18)。此外,已经证明通式(I)化合物是额外的阴离子乳化剂:
其中R1和R2表示氢原子或C4-C24烷基,并且不同时是氢原子,M1和M2可以是碱金属离子和/或铵离子。在通式(I)中,R1和R2优选表示具有6-18个碳原子的直链或支化烷基,尤其是具有6、12和16个碳原子,或氢,R1和R2不同时是氢原子。M1和M2优选是钠、钾或铵,特别优选钠。特别有利的化合物(I)是其中M1和M2是钠,R1是具有12个碳原子的支化烷基,R2是氢原子或R1。通常使用具有50-90重量%比例的单烷基化产物的工业混合物,例如2A1(Dow Chemical Company的品牌)。
合适的阳离子乳化剂一般是具有C6-C18烷基、C6-C18烷基芳基或杂环基的阳离子盐,例如伯、仲、叔或季铵盐,链烷醇铵盐,吡啶盐,咪唑盐、唑盐、吗啉盐、噻唑盐和氧化胺的盐,喹啉盐,异喹啉盐,卓盐,锍盐和盐。例如可以提到十二烷基乙酸铵或相应的硫酸盐,各种2-(N,N,N-三甲基铵)乙基链烷酸酯的硫酸盐或乙酸盐,N-十六烷基硫酸吡啶N-月桂基硫酸吡啶N-十六烷基-N,N,N-三甲基硫酸铵,N-十二烷基-N,N,N-三甲基硫酸铵,N-辛基-N,N,N-三甲基硫酸铵、N,N-二硬脂基-N,N-二甲基硫酸铵,Gemini表面活性剂N,N’-二月桂基-N,N,N’,N’-四甲基乙二胺二硫酸盐,乙氧基化(牛油脂肪烷基)-N-甲基硫酸铵和乙氧基化油胺(例如AC,来自BASF Aktiengesellschaft,约12个环氧乙烷单元)。对于阴离子抗衡基团而言必要的是具有最低可能的亲核性,例如高氯酸盐、硫酸盐、磷酸盐、硝酸盐和羧酸盐,例如乙酸盐、三氟乙酸盐、三氯乙酸盐、丙酸盐、草酸盐、柠檬酸盐或苯甲酸盐,以及有机磺酸的共轭阴离子,例如甲基磺酸盐、三氟甲基磺酸盐和链烷甲苯磺酸盐,以及四氟硼酸盐、四苯基硼酸盐、四(五氟苯基)硼酸盐、四[二(3,5-三氟甲基)苯基]硼酸盐,六氟磷酸盐,六氟砷酸盐,或六氟锑酸盐。
优选的乳化剂是非离子乳化剂,尤其是乙氧基化醇和脱水山梨醇酯,特别优选乙氧基化脂肪醇和脱水山梨醇脂肪酸酯。非常特别优选的混合物含有乙氧基化醇和脱水山梨醇酯。在一个优选实施方案中,此混合物含有乙氧基化醇和脱水山梨醇酯。
在另一个优选实施方案中,基于聚异丁烯和马来酸酐的最终反应产物(PIBSA)和二(烷基)乙醇胺的聚合物是合适的。在一个另外的优选实施方案中,嵌段共聚物是合适的,例如参见Macromolecules 38(16),6882-6887;基于异戊二烯和甲基丙烯酸甲酯的嵌段共聚物例如参见WO2008/009424,或聚(乙烯/丁烯-嵌段-环氧乙烷)。
优选用做分散剂的乳化剂的总用量有利地是0.005-20重量%,优选0.01-15重量%,尤其是0.1-10重量%,在每种情况下基于在阶段A)中的总物料计。除了乳化剂或代替乳化剂用做分散剂的保护胶体的总量通常是0.1-10重量%,一般是0.2-7重量%,在每种情况下基于在阶段A)中的总物料计。
本发明的其中聚酯单体作为大部分存在的微乳液含有连续的非极性相和不连续的极性相。极性相含有极性液体,非极性相含有非极性液体。有效化合物基本上以固体、溶解的、乳化的或分散的形式存在于不连续相中。聚酯单体、分散剂或酶可以既同时分布在两相中的仅仅一相中,也可以分布在两相中,或处于两相的界面处。在一个优选实施方案中,聚酯单体在极性相中的存在量是至少70重量%,优选至少80重量%,尤其是至少90重量%,在每种情况下基于在阶段A)中的聚酯单体的总量计。在另一个优选实施方案中,极性液体是由至少一种聚酯单体和至少一种有效化合物组成的。
本发明的反相微乳液的不连续相的液滴的平均尺寸可以优选根据准弹性动态光散射在1重量%微乳液上检测,所述微乳液是通过用相应的连续相稀释反相微乳液、并且如果合适的话分离有机相获得的(这称为自关联功能的单模态分析的Z均液滴直径dZ)。另外的检测方法是光或电子显微光谱,以及场流分级。如此对于反相微乳液检测的dZ的值是根据本发明一般小于10,000nm,经常小于1000nm,一般是小于500nm。本发明的dZ范围方便地是2000-1000nm。一般,要根据本发明使用的反相微乳液的dZ是大于40nm。
合适的极性液体是在连续非极性相中在反应条件下具有小于40重量%、优选小于10重量%、尤其小于1重量%的溶解度的那些极性液体(在每种情况下基于连续相的总量计),从而存在单独的不连续极性相。在一个优选实施方案中,极性液体在20℃下溶解了聚酯单体至至多10重量%,优选至多3重量%,尤其是至多0.5重量%,在每种情况下基于聚酯单体的总重量计。
合适的极性液体是例如一元醇,例如C3-C6链烷醇,尤其是叔丁醇和叔戊醇,吡啶,聚C1-C4亚烷基二醇二C1-C4烷基醚,尤其是聚乙二醇二C1-C4烷基醚,例如二甲氧基乙烷、二甘醇二甲醚或聚乙二醇二甲醚500,C2-C4亚烷基碳酸酯,尤其是碳酸亚丙基酯,乙酸C3-C6烷基酯,尤其是乙酸叔丁酯,丙酮,1,4-二恶烷,1,3-二氧戊环,四氢呋喃,二甲氧基甲烷,二甲氧基乙烷,含水缓冲剂或水。显然也可以使用上述溶剂的混合物。上述聚酯单体或它们的混合物也是合适的极性液体。
极性液体可以例如还包含所用的有效化合物,或可以由其组成。碳酸亚丙酯和包含碳酸亚丙酯的混合物是优选的极性液体。在另一个优选实施方案中,聚酯单体是极性液体。
如果内酯用做聚酯单体,则极性液体含有小于5重量%、优选小于1重量%和尤其小于0.1重量%的水。如果极性液体含有水,则有利的是含水反应介质显示在环境温度(20-25℃)下的pH是2-11,经常是3-9,通常是6-8。尤其是,在含水反应介质中,pH被调节到酶能显示高催化活性和高使用寿命的值。调节pH的合适措施,即添加合适量的以下物质是本领域技术人员熟知的:酸,例如硫酸;碱,例如碱金属氢氧化物水溶液,尤其是氢氧化钠或氢氧化钾;或缓冲剂,例如磷酸二氢钾/磷酸氢二钠,乙酸/乙酸钠,氢氧化铵/氯化铵,磷酸二氢钾/氢氧化钠,硼砂/盐酸,硼砂/氢氧化钠或三(羟基甲基)氨基甲烷/盐酸。
为了进一步提高极性相的极性,可以另外含有“亲水化剂”。合适的亲水化剂是例如有机或无机的盐,或高极性中性化合物。无机盐的例子是硝酸钠、氯化钠、氯化钾、氯化锂或氯化铷。有机盐的例子是三烷基铵盐,离子液体,例如乙基甲基咪唑翁盐,或在主链或侧链中具有化学计算量比例的阴离子基团和阳离子基团的低聚物。优选不会降低酶的催化活性的亲水化剂。
合适的非极性液体是在不连续极性相中在反应条件下具有小于10重量%、优选小于1重量%和尤其小于0.1重量%的溶解度的那些(在每种情况下基于连续相的总量计),从而存在单独的连续极性相。
合适的非极性液体是例如脂族或芳族的具有5-30个碳原子的液体烃,例如正戊烷和异构体,环戊烷,正己烷和异构体,环己烷,正庚烷和异构体,正辛烷和异构体,正壬烷和异构体,正癸烷和异构体,正十二烷和异构体,正十四烷和异构体,正十六烷和异构体,正十八烷和异构体,苯,甲苯,乙苯,枯烯,邻二甲苯,间二甲苯,或对二甲苯,或1,3,5-三甲基苯。也合适的是沸点范围为30-250℃的烃混合物,例如部分氢化的矿物油馏出物(例如品牌,来自Exxon Mobil)。烯烃也是合适的,例如聚异丁烯或C6-C30α-烯烃。也可以使用羟基化合物,例如饱和和不饱和的具有10-28个碳原子的脂肪醇,例如正十二醇、正十四醇、正十六醇以及它们的异构体或鲸蜡醇,或酯,例如在酸部分中具有10-28个碳原子且在醇部分中具有1-10个碳原子的脂肪酸酯,或在羧酸部分中具有1-10个碳原子且在醇部分中具有10-28个碳原子的羧酸和脂肪醇的酯。其它合适的非极性液体是液体石蜡(直链烃混合物)、硅油(聚硅氧烷)、全氟化烃、氟硅油、全氟化聚醚、氟硅烷或硅氧烷,例如二甲基硅氧烷。优选的非极性液体是脂族和芳族的具有5-30个碳原子的液体烃,尤其是部分氢化的矿物油馏出物。在另一个实施方案中,非极性液体是液体石蜡。显然也可以使用上述溶剂的混合物。
极性和非极性液体的总量的选择使得在阶段A)中的总物料达到100重量%。其一般是10-90重量%,优选40-70重量%,基于总物料计。
在这方面,选择极性液体和非极性液体之间的重量比,使得产生不连续相,其基本上含有极性液体。在一个优选实施方案中,使用20-80重量%、优选40-70重量%的非极性液体,在每种情况下基于总物料计。在另一个优选实施方案中,使用20-80重量%、优选30-60重量%的极性液体,在每种情况下基于总物料计。在另一个优选实施方案中,使用20-80重量%、优选35-55重量%的烃混合物和20-70重量%、优选30-60重量%的碳酸亚丙酯,在每种情况下基于总物料计。在这方面需要注意的是,微乳液不会发生相反转,即疏水连续相不会成为分散相。
术语“有效化合物”应当理解为在本发明中表示能引起在本发明产品的工业应用中使用者所希望的效果的那些化合物。有效化合物是例如着色剂、化妆品、药物、杀微生物剂、植物保护剂、农业化学助剂、肥料,用于食品或动物饲料的添加剂,或用于聚合物、纸、织物、皮革、洗涤剂或清洁剂的助剂。本领域技术人员能根据所需的应用领域在常识基础上选择合适的有效化合物。
着色剂的例子是染料、印刷油墨、颜料、UV吸收剂、荧光增白剂或IR染料。有机染料具有在400-850nm波长范围内的最大吸收值,荧光增白剂具有在250-400nm范围内的一个或多个吸收最大值。已经知道荧光增白剂能在用UV光辐射时释放出在可见光区域内的荧光。荧光增白剂的例子是以下类别的化合物:二苯乙烯基苯,1,2-二苯乙烯,苯并唑,香豆素,苝,以及萘。用于液体的标记化合物也是合适的,例如矿物油标记化合物。术语“UV吸收剂”理解为一般表示能吸收UV辐射的化合物,其用非辐射方式使被吸收的辐射惰化。这些化合物例如用于防晒和用于稳定有机聚合物。
化妆品是额外的合适有效化合物。化妆品是化合物或化合物的组合物,它们是完全或主要用于在外部施用到人体上或人口腔中用于清洁、护理、保护、保持良好状况、香味或改变外观,或施用以影响体味。驱虫剂也是合适的,例如或N,N-二乙基-间-甲苯甲酰胺
另外,所有药物也可以用做有效化合物。
以下物质可以用做杀微生物剂:含有重金属的杀微生物剂,例如(N-环己基二氮杂烯翁二氧基)三丁锡或二(N-环己基二氮杂烯翁二氧基)铜(CuHDO);金属皂,例如锡、铜或锌的环烷酸盐、辛酸盐、2-乙基己酸盐、油酸盐、磷酸盐或苯甲酸盐;金属盐,例如碱性碳酸铜、二氯酸钠、二氯酸钾、氯酸钾、硫酸铜、氯化铜、硼酸铜、氟硅酸锌、氟硅酸铜或2-吡啶硫醇1-氧化物的铜盐;氧化物,例如氧化二丁基锡,Cu2O,CuO或ZnO;或含有Ag、Zn或Cu的沸石,其单独地存在或包含在聚合物活性化合物中。合适的杀微生物剂优选是杀藻剂,例如敌草隆、双氯酚、草藻灭、三苯基乙酸锡或灭藻醌;灭螺剂,例如三苯基乙酸锡、四聚乙醛、灭虫威、贝螺杀、硫双灭多威和三甲威;杀真菌剂,例如二噻农、溴硝醇、苯氟磺胺、甲苯氟磺胺、碘代炔丙基丁基氨基甲酸酯、N-邻苯二甲酰亚胺;以及唑类,例如戊唑醇;或常规防污活性化合物,例如2-(N,N-二甲基硫代氨基甲酰基硫)-5-硝基噻唑,四丁基二锡烷,2-(叔丁基)氨基-4-环丙基氨基-6-甲基硫代-1,3,5-三嗪,4,5-二氯-2-(n-辛基)-4-异噻唑啉-3-酮,2,4,5,6-四氯间苯二甲酰基二甲腈,二硫化四甲基秋兰姆,2,4,6-三氯苯基马来酰亚胺,2,3,5,6-四氯-4-(甲基磺酰基)吡啶,二碘甲基对-甲苯基砜,噻唑,四苯基硼酸吡啶翁,或2-吡啶硫醇1-氧化物的钠盐。另外的例子是亚氯酸钠(NaClO2)或2,4-二氯苄基醇(DCBA)。优选的杀微生物剂是二(N-环己基二氮杂烯翁二氧基)铜、二噻农、溴硝醇、亚氯酸钠(NaClO2)或2,4-二氯苄基醇。
本发明的含有杀微生物剂的微胶囊可以使用,不论表面是否含有细菌、藻和真菌,即微生物表面,或这些表面应当具有不粘性能。它们可以用于以下领域中:
-海洋:船体,甲板,浮标,钻井平台,压载水舱;
-房屋:屋顶,地下室,壁,表面,温室,防晒保护,花园栅栏,木材防护;
-卫生:公共厕所,浴室,淋浴幕帘,化妆品,游泳池,桑拿房,关节,连接化合物;
-食品:机械,厨房,厨房用品,海绵,玩具,食品包装,牛奶加工,饮水系统,化妆品;
-机器部件:空调系统,离子交换器,工艺水,太阳能装置,换热器,生物反应器,膜,冷却水处理;
-医疗工程:接触透镜,尿布,膜,植入物;
-物品:汽车坐椅,布(长筒袜,运动服装),医院设备,门把手,电话机座,公共运输,动物笼子,点验钞机,地毯,壁纸。
植物保护剂和肥料也可以用做有效化合物。杀螨剂、杀藻剂、杀蚜剂、杀细菌剂、杀真菌剂、除草剂、杀虫剂、灭螺剂、杀线虫剂、萌芽抑制剂、安全剂或生长调节剂是合适的植物保护剂。杀真菌剂是能破坏真菌和它们的孢子或抑制它们生长的化合物。杀虫剂是在它们的效果中尤其涉及抵抗昆虫和它们的发展形式的化合物。术语“除草剂”理解为表示对一般在相应位置处不需要的所有野生植物和作物(有害植物)有抵抗活性的化合物。
肥料的例子是无机的单或多成核剂肥料,有机和有机/无机的肥料,或具有微量元素的肥料。
在一个优选实施方案中,有效化合物是植物保护剂或植物保护剂的混合物。在另一个优选实施方案中,植物保护剂优选是除草剂、生长调节剂、杀虫剂或杀真菌剂。一般知道为了抵抗不需要的植物、昆虫或真菌,可以有利地使用植物保护剂。下列植物保护剂证明了可能的活性化合物,但是不限于此。
可以使用例如以下物质作为杀真菌剂:
A)甲氧基丙烯酸酯类:
嘧菌酯,醚菌胺,烯肟菌酯,氟嘧菌酯,醚菌酯,苯氧菌胺,肟醚菌胺,啶氧菌酯,吡唑嘧菌酯,吡菌苯威(pyribencarb),肟菌酯,2-(2-(6-(3-氯-2-甲基苯氧基)-5-氟嘧啶-4-基氧基)苯基)-2-甲氧基亚氨基-N-甲基乙酰胺,甲基2-(邻-((2,5-二甲基苯基)氧基亚甲基)苯基)-3-甲氧基丙烯酸酯,甲基3-甲氧基-2-(2-(N-(4-甲氧基苯基)环丙烷羧酰亚氨基硫烷基甲基)苯基)丙烯酸酯,2-(2-(3-(2,6-二氯苯基)-1-甲基亚烯丙基氨基氧基甲基)苯基)-2-甲氧基亚氨基-N-甲基乙酰胺;
B)羧酰胺:
-甲酰苯胺类:苯霜灵,精苯霜灵,麦锈灵,联苯吡菌胺(bixafen),啶酰菌胺,萎锈灵,甲呋酰胺,环酰菌胺,氟酰胺,呋吡菌胺,萘吡菌胺(isopyrazam),异噻菌胺,高效苯霜灵(kiralaxyl),灭锈胺,甲霜灵,精甲霜灵(mefenoxam),甲呋酰胺,恶霜灵,氧化萎锈灵,吡噻菌胺,叶枯酞,噻氟菌胺,噻酰菌胺,2-氨基-4-甲基噻唑-5-甲酰苯胺,2-氯-N-(1,1,3-三甲基二氢化茚-4-基)烟酰胺,N-(2′,4′-二氟联苯基-2-基)-3-二氟甲基-1-甲基-1H-吡唑-4-羧酰胺,N-(2′,4′-二氯联苯基-2-基)-3-二氟甲基-1-甲基-1H-吡唑-4-羧酰胺,N-(2′,5′-二氟联苯基-2-基)-3-二氟甲基-1-甲基-1H-吡唑-4-羧酰胺,N-(2′,5′-二氯联苯基-2-基)-3-二氟甲基-1-甲基-1H-吡唑-4-羧酰胺,N-(3′,5′-二氟联苯基-2-基)-3-二氟甲基-1-甲基-1H-吡唑-4-羧酰胺,N-(3′,5′-二氯联苯基-2-基)-3-二氟甲基-1-甲基-1H-吡唑-4-羧酰胺,N-(3′-氟联苯基-2-基)-3-二氟甲基-1-甲基-1H-吡唑-4-羧酰胺,N-(3′-氯联苯基-2-基)-3-二氟甲基-1-甲基-1H-吡唑-4-羧酰胺,N-(2′-氟联苯基-2-基)-3-二氟甲基-1-甲基-1H-吡唑-4-羧酰胺,N-(2′-氯联苯基-2-基)-3-二氟甲基-1-甲基-1H-吡唑-4-羧酰胺,N-(3′,4′,5′-三氟联苯基-2-基)-3-二氟甲基-1-甲基-1H-吡唑-4-羧酰胺,N-(2′,4′,5′-三氟联苯基-2-基)-3-二氟甲基-1-甲基-1H-吡唑-4-羧酰胺,N-[2-(1,1,2,3,3,3-六氟丙氧基)苯基]-3-二氟甲基-1-甲基-1H-吡唑-4-羧酰胺,N-[2-(1,1,2,2-四氟乙氧基)苯基]-3-二氟甲基-1-甲基-1H-吡唑-4-羧酰胺,N-(4′-三氟甲基硫代联苯基-2-基)-3-二氟甲基-1-甲基-1H-吡唑-4-羧酰胺,N-(2-(1,3-二甲基丁基)苯基)-1,3-二甲基-5-氟-1H-吡唑-4-羧酰胺,N-(2-(1,3,3-三甲基丁基)苯基)-1,3-二甲基-5-氟-1H-吡唑-4-羧酰胺,N-(4′-氯-3′,5′-二氟联苯基-2-基)-3-二氟甲基-1-甲基-1H-吡唑-4-羧酰胺,N-(4′-氯-3′,5′-二氟联苯基-2-基)-3-三氟甲基-1-甲基-1H-吡唑-4-羧酰胺,N-(3′,4′-二氯-5′-氟联苯基-2-基)-3-三氟甲基-1-甲基-1H-吡唑-4-羧酰胺,N-(3′,5′-二氟-4′-甲基联苯基-2-基)-3-二氟甲基-1-甲基-1H-吡唑-4-羧酰胺,N-(3′,5′-二氟-4′-甲基联苯基-2-基)-3-三氟甲基-1-甲基-1H-吡唑-4-羧酰胺,N-[2-(双环丙基-2-基)苯基]-3-二氟甲基-1-甲基
-1H-吡唑-4-羧酰胺,N-[2-(顺-双环丙基-2-基)苯基}-3-二氟甲基-1-甲基
-1H-吡唑-4-羧酰胺,N-[2-(反-双环丙基-2-基)苯基]-3-二氟甲基-1-甲基
-1H-吡唑-4-羧酰胺,N-[1,2,3,4-四氢-9-(1-甲基乙基)-1,4-甲烷萘-5-基]-3-二氟甲基-1-甲基-1H-吡唑-4-羧酰胺;
-羧酸酰吗啉类:烯酰吗啉,氟吗啉;
-苯并酰胺:氟酰菌胺,氟吡菌胺,氟吡菌酰胺,苯酰菌胺,N-(3-乙基-3,5,5-三甲基环己基)-3-甲酰基氨基-2-羟基苯甲酰胺;
-其它羧酰胺:环丙酰菌胺,双氯氰菌胺,双炔酰菌胺,土霉素,硅噻菌胺,N-(6-甲氧基吡啶-3-基)环丙烷羧酰胺;
C)唑类:
-三唑:戊环唑,联苯三唑醇,糠菌唑,环唑醇,恶醚唑,烯唑醇,烯唑醇-M,氟环唑,腈苯唑,氟喹唑,氟硅唑,粉唑醇,己唑醇,酰胺唑,种菌唑,叶菌唑,腈菌唑,恶咪唑,多效唑,戊菌唑,丙环唑,丙硫菌唑,硅氟唑,戊唑醇,氟咪唑,三唑酮,三唑醇,灭菌唑,烯效唑,1-(4-氯苯基)-2-(1,2,4-三唑-1-基)环庚醇;
-咪唑:氟唑磺菌胺,抑霉唑,硫酸抑霉唑,稻瘟酯,咪鲜安,氟菌唑;
-苯并咪唑:苯菌灵,多菌灵,麦穗宁,噻菌灵;
-其它:噻唑菌胺,土菌灵,恶霉灵,2-(4-氯苯基)-N-[4-(3,4-二甲氧基苯基)异恶唑-5-基]-2-(丙-2-炔氧基)乙酰胺;
D)含氮的杂环化合物
-吡啶:氟啶胺,啶斑肟,3-[5-(4-氯苯基)-2,3-二甲基异恶唑烷-3-基]吡啶,3-[5-(4-甲基苯基)-2,3-二甲基异恶唑烷-3-基]吡啶,2,3,5,6-四氯-4-(甲烷磺酰基)吡啶,3,4,5-三氯吡啶-2,6-二甲腈,N-(1-(5-溴-3-氯吡啶-2-基)乙基)-2,4-二氯烟酰胺,N-((5-溴-3-氯吡啶-2-基)甲基)-2,4-二氯烟酰胺;
-嘧啶类:乙嘧酚磺酸酯,嘧菌环胺,二氟林,氯苯嘧啶醇,嘧菌腙,嘧菌胺,氯甲基吡啶,噻菌醇,嘧霉胺;
-哌嗪类:嗪氨灵;
-吡咯类:咯菌腈,拌种咯;
-吗啉类:十二吗啉(aldimorph),吗菌灵,乙酸吗菌灵,丁苯吗啉,十三吗啉;
-哌啶类:苯锈啶;
-二羧酰亚胺类:氟菌利(Fluorimid),异菌脲,杀菌利,乙烯菌核利;
-非芳族的5元杂环:恶唑菌酮,咪唑菌酮,噻菌净(flutianil),辛噻酮,烯丙异噻唑,5-氨基-2-异丙基-3-氧-4-(邻甲苯基)-2,3-二氢吡唑-1-硫代羧酸S-烯丙基酯;
-其它:阿拉酸式苯-S-甲基,安美速,敌菌灵,灭瘟素,敌菌丹,克菌丹,喹菌酮,棉隆,咪菌威,哒菌酮,野燕枯,燕麦清(difenzoquat-metilsulfate),氰菌胺,灭菌丹,恶喹酸,粉病灵,丙氧喹啉,咯喹酮,喹氧灵,咪唑嗪,三环唑,2-丁氧基-6-碘-3-丙基苯并吡喃-4-酮,5-氯-1-(4,6-二甲氧基嘧啶-2-基)-2-甲基-1H-苯并咪唑,5-氯-7-(4-甲基哌啶-1-基)-6-(2,4,6-三氟苯基)-[1,2,4]三唑[1,5-a]嘧啶,6-(3,4-二氯苯基)-5-甲基-[1,2,4]三唑[1,5-a]嘧啶-7-基胺,6-(4-叔丁基苯基)-5-甲基-[1,2,4]三唑[1,5-a]嘧啶-7-基胺,5-甲基-6-(3,5,5-三甲基己基)-[1,2,4]三唑[1,5-a]嘧啶-7-基胺,5-甲基-6-辛基-[1,2,4]三唑[1,5-a]嘧啶-7-基胺,6-甲基-5-辛基-[1,2,4]三唑[1,5-a]嘧啶-7-基胺,6-乙基-5-辛基-[1,2,4]三唑[1,5-a]嘧啶-7-基胺,5-乙基-6-辛基-[1,2,4]三唑[1,5-a]嘧啶-7-基胺,5-乙基-6-(3,5,5-三甲基己基)-[1,2,4]三唑[1,5-a]嘧啶-7-基胺,6-辛基-5-丙基-[1,2,4]三唑[1,5-a]嘧啶-7-基胺,5-甲氧基甲基-6-辛基-[1,2,4]三唑[1,5-a]嘧啶-7-基胺,6-辛基-5-三氟甲基-[1,2,4]三唑[1,5-a]嘧啶-7-基胺和5-三氟甲基-6-(3,5,5-三甲基己基)-[1,2,4]三唑[1,5-a]嘧啶-7-基胺;
E)氨基甲酸酯和二硫代氨基甲酸酯
-硫代-和二硫代氨基甲酸酯:福美铁,代森锰锌,代森锰,威百亩,磺菌威,代森联,丙森锌,福美双,代森锌,福美锌;
-氨基甲酸酯:乙霉威,苯噻菌胺,丙森锌,霜霉威,霜霉威盐酸盐,霜霉灭,4-氟苯基N-(1-(1-(4-氰基苯基)乙基磺酰基)丁-2-基)氨基甲酸酯;
F)其它杀真菌剂
-胍:多果定,多果定自由碱(dodine free base),双胍辛胺,乙酸双胍辛胺,双胍辛胺(iminoctadine),三乙酸双胍辛胺,双胍三辛胺烷基苯磺酸盐;
-抗菌素:春雷霉素,春雷霉素盐酸盐水合物,多氧霉素,链霉素,井冈霉素A;
-硝基苯基衍生物:乐杀螨,氯硝胺,敌螨通,敌螨普,菌酞酯,四氯硝基苯;
-有机金属化合物:三苯基锡盐,例如三苯基乙酸锡、三苯基氯化锡、三苯基氢氧化锡;
-含硫的杂环化合物:二腈蒽醌,稻瘟灵;
-有机磷化合物:敌瘟磷,三乙膦酸,三乙膦酸铝,异稻瘟净,亚磷酸及其盐,吡菌磷,甲基立枯磷;
-有机氯化合物:百菌清,苯氟磺胺,双氯酚,磺菌胺,六氯苯,戊菌隆,五氯苯酚及其盐,丁基酞内酯,五氯硝基苯,甲基硫菌灵,对甲抑菌灵,N-(4-氯-2-硝基苯基)-N-乙基-4-甲基苯磺酰胺;
-无机活性化合物:磷酸及其盐,波尔多(Bordeaux)混合物,铜盐,例如乙酸铜、氢氧化铜、氧基氯化铜、碱性硫酸铜,硫;
-其它:联苯,溴硝醇,环氟菌胺,霜脲氰,二苯基胺,苯酮菌,灭粉霉素,羟基喹啉铜,调环酸钙,螺环菌胺,对甲抑菌灵,N-(环丙基甲氧基亚氨基(6-二氟甲氧基-2,3-二氟苯基)甲基)-2-苯基乙酰胺,N′-(4-(4-氯-3-三氟甲基苯氧基)-2,5-二甲基苯基)-N-乙基-N-甲基甲脒,N′-(4-(4-氟-3-三氟甲基)苯氧基)-2,5-二甲基苯基)-N-乙基-N-甲基甲脒,N′-(2-甲基-5-三氟甲基-4-(3-(三甲基硅烷基)丙氧基)苯基)-N-乙基-N-甲基甲脒,N′-(5-二氟甲基-2-甲基-4-(3-三甲基硅烷基)丙氧基)苯基)-N-乙基-N-甲基甲脒,2-{1-[2-(5-甲基-3-三氟甲基)吡唑-1-基)乙酰基]-哌啶-4-基}噻唑-4-羧酸甲基(1,2,3,4-四氢萘-1-基)酰胺,2-{1-[2-(5-甲基-3-(三氟甲基)吡唑-1-基)乙酰基]哌啶-4-基}噻唑-4-羧酸甲基(R)-1,2,3,4-四氢萘-1-基)酰胺,6-(叔丁基)-8-氟-2,3-二甲基喹啉-4-基乙酸酯,6-(叔丁基)-8-氟-2,3-二甲基喹啉-4-基甲氧基乙酸酯。
作为生长调节剂,可以使用例如:
脱落酸,呋喃丹,环丙嘧啶醇,6-苄基氨基嘌呤,芸苔素内酯,丁乐灵,矮壮素(chlormequat chloride),氯化胆碱,环丙酸酰胺,丁酰肼,调呋酸,噻节因,2,6-二甲基嘌呤,乙烯利,氟节胺,呋嘧醇,氟噻草酯,氯吡苯脲,赤霉素,抗倒胺,吲哚-3-乙酸,马来酰肼,氟磺酰草胺,甲哌啶(氯化甲哌啶),叶菌唑,萘基乙酸,N6-苄基腺嘌呤,多效唑,调环酸(调环酸钙),茉莉酮,噻苯隆,抑芽唑,三丁基三硫磷酸酯,2,3,5-三碘苯甲酸,抗倒酯和烯效唑。
作为除草剂,可以使用例如:
-乙酰胺:乙草胺,甲草胺,丁草胺,二甲草胺,二甲吩草胺,氟噻草胺,苯噻草胺,异丙草胺,吡草胺,敌草胺,萘丙胺,烯草胺,丙草胺,毒草胺,噻吩草胺;
-氨基酸类似物:双丙氨磷,草甘膦,草丁膦,草硫膦;
-芳氧基苯氧基丙酸酯:炔草酯,氰氟草酯,精恶唑禾草灵,吡氟禾草灵,吡氟氯禾灵,恶唑酰草胺,喔草酯,精喹禾灵,喹禾糠酯;
-联吡啶:敌草快,百草枯;
-氨基甲酸酯和硫代氨基甲酸酯:磺草灵,丁酸酯,卡草胺,甜安宁,哌草丹,扑草灭(EPTC),戊草丹,禾草特,坪草丹,甜安宁,苄草丹,稗草畏,禾草丹,野麦畏;
-环己烷二酮:丁氧环酮,烯草酮,噻草酮,环苯草酮,稀禾定,快捕净,肟草酮;
-二硝基苯胺:氟草胺,丁氟消草,安磺灵,二甲戊乐灵,氨基丙氟灵,氟乐灵;
-二苯基醚:三氟羧草醚,苯草醚,甲羧除草醚,禾草灵,氯氟草醚乙酯,氟黄胺草醚,乳氟禾草灵,乙氧氟草醚;
-羟基苯并腈:溴苯腈,敌草腈,碘苯腈;
-咪唑啉酮:咪草酸,甲氧咪草烟,甲咪唑烟酸,灭草烟,灭草喹,咪草烟;
-苯氧基乙酸:氯甲酰草胺,2,4-二氯苯氧基乙酸(2,4-D),2,4-DB,2,4-滴丙酸,MCPA,MCPA-硫乙基,MCPB,2-甲-4-氯丙酸;
-吡嗪:氯草敏,氟哒嗪草酯,氟噻草酯,哒草伏,哒草特;
-吡啶:氯氨吡啶酸,二氯吡啶甲酸,吡氟草胺,氟硫草定,氟啶酮,氟草烟,毒莠定,氟吡酰草胺,噻草啶;
-磺酰基脲:酰嘧磺隆,四唑嘧磺隆,苄嘧磺隆,氯嘧磺隆,氯磺隆,醚磺隆,环丙嘧磺隆,乙氧嘧磺隆,啶嘧磺隆,氟吡磺隆,氟啶嘧磺隆,甲酰胺磺隆,氯吡嘧磺隆,咪唑磺隆,碘钾磺隆,甲磺胺磺隆,甲磺隆,烟嘧磺隆,环氧嘧磺隆,氟嘧磺隆,氟磺隆,吡嘧黄隆,砜嘧磺隆,甲嘧磺隆,磺酰磺隆,噻磺隆,醚苯磺隆,苯磺隆,三氟啶磺隆,氟胺磺隆,三氟甲磺隆,1-((2-氯-6-丙基咪唑[1,2-b]哒嗪-3-基)磺酰基)-3-(4,6-二甲氧基嘧啶-2-基)脲;
-三嗪:莠灭净,莠去津,氰草津,排草净,乙嗪草酮,环嗪酮,苯嗪草酮,嗪草酮,扑草净,西玛津,草净津,特丁净,吡嘧磺隆;
-脲:氟草隆(fluorotoluron),杀草隆,敌草隆,伏草隆,异丙隆,利谷隆,甲基苯噻隆,特丁噻草隆;
-其它乙酰基乳酸酯合成酶抑制剂:双草醚,氯酯磺草胺,双氯磺草胺,双氟磺草胺,氟酮磺隆,唑嘧磺草胺,磺草唑胺,嘧苯胺磺隆,五氟磺草胺,丙苯磺隆,丙酯草醚,嘧啶肟草醚,环酯草醚,嘧草醚甲基,嘧啶硫蕃,嘧草硫醚,派罗克杀草砜(pyroxasulfone),甲氧磺草胺;
-其它:胺唑草酮,氨基三唑,莎稗磷,氟丁酰草胺,草除灵,苯并卡巴腙(benzocarbazone),呋草黄,吡草酮,灭草松,苯并双环酮,溴丙酮,溴丁酰草胺,氟丙嘧草酯,克蔓磷,唑草胺,氟酮唑草,吲哚酮草酯,敌草索,环庚草醚,异噁草酮,苄草隆,环丙磺酰胺,麦草畏,燕麦枯,氟吡草腙,稗内脐蠕孢菌,草藻灭,乙呋草黄,乙氧苯草胺,四唑草胺,氟烯草酸,丙炔氟草胺,胺草唑,氟咯草酮,呋草酮,茚草酮,异噁草胺,异恶唑草酮,环草定,敌稗,戊炔草胺,二氯喹啉酸,喹草酸,甲基磺草酮,甲基砷酸,抑草生,炔恶草酮,恶草酮,噁嗪草酮,恶嗪酮,唑啉草酯,双唑草腈,吡草醚,苯甲酰吡唑类除草剂(Pyrasulfotole),苄草唑,吡唑特,灭藻醌,嘧啶肟草醚,磺草酮,磺酰唑草酮,特草定,苯甲酰环己二酮类除草剂(Tefuryltrione),三酮类玉米田除草剂(Tembotrione),酮脲磺草吩酯,苯吡唑草酮,4-羟基-3-[2-(2-甲氧基乙氧基甲基)-6-(三氟甲基)吡啶-3-羰基]双环[3.2.1]辛-3-烯-2-酮,乙基(3-[2-氯-4-氟-5-(3-甲基-2,6-二氧-4-三氟甲基-3,6-二氢-2H-嘧啶-1-基)苯氧基]吡啶-2-基氧基)乙酸酯,6-氨基-5-氯-2-环丙基嘧啶-4-羧酸酯,6-氯-3-(2-环丙基-6-甲基苯氧基)哒嗪-4-醇,4-氨基-3-氯-6-(4-氯苯基)-5-氟吡啶-2-羧酸,甲基4-氨基-3-氯-6-(4-氯-2-氟-3-甲氧基苯基)吡啶-2-羧酸酯和甲基4-氨基-3-氯-6-(4-氯-3-二甲基氨基-2-氟苯基)吡啶-2-羧酸酯。
作为杀虫剂,可以使用例如:
-有机(硫代)磷酸酯:乙酰甲胺磷,甲基吡啶磷,谷硫磷,毒死蜱,甲基毒死蜱,杀螟威,二嗪磷,敌敌畏,百治磷,乐果,乙拌磷,乙硫磷,杀螟硫磷,倍硫磷,异恶唑磷,马拉硫磷,甲胺磷,杀扑磷,甲基对硫磷,速灭磷,久效磷,砜吸磷,对氧磷,对硫磷,稻丰散,伏杀硫磷,亚胺硫磷,磷胺,甲拌磷,辛硫磷,甲基嘧啶磷,溴磷松,普硫松,硫丙磷,杀虫畏,甲基异柳磷,三唑磷,敌百虫;
-氨基甲酸酯:涕灭威,铁灭克,噁虫威,丙硫克百威,甲萘威,克百威,丁硫克百威,苯氧威,呋线威,灭虫威,灭多虫,杀线威,抗蚜威,残杀威,硫双灭多威,唑蚜威;
-拟除虫菊酯:烯丙菊酯,联苯菊酯,氟氯氰菊酯,氯氟氰菊酯,苯醚氰菊酯,氯氰菊酯,顺式氯氰菊酯,乙体氯氰菊酯,Z-氯氰菊酯,溴氰菊酯,高效氰戊菊酯,醚菊酯,甲氰菊酯,氰戊菊酯,炔咪菊酯,高三氟氯氰菊酯,氯菊酯,右旋炔丙菊酯,除虫菊酯I和II,苄氟菊酯,氟硅菊酯,氟胺氰菊酯,七氟菊酯,胺菊酯,四溴菊酸,四氟苯菊酯,丙氟菊酯,四氟甲醚菊酯;
-昆虫生长抑制剂:a)几丁质合成抑制剂:苯甲酰脲:定虫隆,灭蝇胺,除虫脲,氟螨脲,氟虫脲,氟铃脲,氟丙氧脲,双苯氟脲,伏虫隆,杀铃脲,噻嗪酮,苯虫醚,噻螨酮,乙螨唑,四螨嗪;b)蜕皮激素拮抗剂:氯虫酰肼,甲氧虫酰肼,虫酰肼,印楝素;c)保幼激素类似物:吡丙醚,甲氧普烯,苯氧威;d)脂类生化合成抑制剂:螺螨酯,螺甲螨酯,螺虫乙酯;
-烟碱型受体激动剂/拮抗剂:可尼丁,呋虫胺,吡虫啉,噻虫嗪,烯虫灵,啶虫脒,噻虫啉,1-(2-氯噻唑-5-基甲基)-2-硝基亚氨基-3,5-二甲基-1,3,5-三嗪烷;
-GABA拮抗剂:硫丹,乙虫腈,氟虫腈,甲烯氟虫腈,吡嗪氟虫腈,氟虫腈(pyriprole),5-氨基-1-(2,6-二氯-4-甲基苯基)-4-亚磺酰氨基-1H-吡唑-3-硫代羧酰胺;
-大环内酯:伊维菌素,富表甲氨基阿维菌素,弥拜菌素,杀螨菌素,多杀菌素,多杀菌素类杀虫剂(spinetoram);
-线粒体电子输送抑制剂(mitochondrial electron transport inhibitor)(METI)I杀螨剂:喹螨醚,达蟥酮,吡螨胺,唑虫酰胺,嘧虫胺;
-METI II和III物质:灭螨醌,嘧螨酯,伏蚁腙;
-解偶联剂:溴虫腈;
-氧化磷酸化抑制剂:三环锡,丁醚脲,苯丁锡,炔螨特;
-昆虫蜕皮抑制剂:灭蝇胺;
-混合官能氧化酶的抑制剂:增效醚;
-钠通道封闭剂:茚虫威,氰氟虫腙;
-其它:硫线磷,联苯肼酯,杀螟丹,氟尼胺,啶虫丙醚,吡蚜酮,硫,杀虫环,氟虫酰胺,氯虫酰胺(chlorantraniliprole),溴氰虫酰胺(HGW86),唑螨氰,吡氟硫磷,丁氟螨酯,磺胺螨酯,新烟碱类(imicyafos),双三氟虫脲和新喹唑啉(pyrifluquinazon)。
在一个优选实施方案中,植物保护剂优选是除草剂。在另一个优选实施方案中,植物保护剂优选是杀虫剂。在另一个优选实施方案中,植物保护剂优选是杀真菌剂。在另一个优选实施方案中,杀真菌剂优选是唑化合物。在另一个优选实施方案中,唑化合物优选是灭菌唑、氟环唑、氟喹唑或叶菌唑。
农业化学助剂是另外合适的有效化合物。助剂是它们本身没有农药作用但能提高农药效力的化合物或化合物混合物。渗透促进剂是例子。所有能常规用于改进农药活性化合物向植物中的渗透的物质适合作为渗透促进剂。渗透促进剂在这方面是以此方式定义的,即它们从含水喷洒混合物和/或从喷洒涂料渗透入植物表皮中,并经由此可以提高活性化合物在表皮中的活动性。在文献中描述的单侧解吸的方法(Baur等,1997,PesticideScience 51,131-152)可以用于检测此性能。另外合适的方法包括在叶子上留下一滴要研究的混合物并检测在数天后在叶子上的残余物。
用于食品或动物饲料的添加剂,例如食品着色剂、氨基酸、维生素、防腐剂、抗氧化剂、香料或调料是其它合适的有效化合物。
用于聚合物的助剂的例子是阻燃剂、粘度改进剂或极性液体,例如可以用于不连续相中。用于纸的助剂的例子是链烯基琥珀酸酐或二烷基二烯酮。用于洗涤剂和清洁剂的助剂的例子是表面活性剂或乳化剂,例如也可以用做反相微乳液中的分散剂。酶例如水解酶或酰胺酶也可以用做助剂。
杀微生物剂、植物保护剂和肥料是优选的有效化合物。在一个实施方案中,有效化合物是植物保护剂。在另一个实施方案中,有效化合物是杀微生物剂。在另一个实施方案中,有效化合物是农业化学助剂。
有效化合物可以以纯形式、工业级别、作为提取物或作为与其它有效化合物的混合物使用。有效化合物以溶解的或以固体的形式存在于分散相中。有效化合物的总量是0.1-90重量%,优选5-50重量%,基于在阶段A)中的总物料计。
有效化合物可以通过从微粒扩散或通过微粒的崩解而从微粒释放出来。释放速率可以通过能影响扩散或崩解的内部和外部作用来选择性地控制。
额外的添加剂是本领域技术人员熟知的,例如防腐剂、增稠剂、分离剂或保护胶体和乳化剂,例如也可以用于本发明方法中的那些,,并且按照常规量根据在生产微粒之后的预期用途加入。
壁单体是选自烯属不饱和单体、多异氰酸酯和/或多环氧化物。多异氰酸酯优选与额外的壁单体一起使用,例如烯属不饱和单体和多异氰酸酯,多异氰酸酯和多元醇,或者多异氰酸酯和多胺。作为壁单体,优选烯属不饱和单体,烯属不饱和单体和多异氰酸酯,烯属单-和多-不饱和单体,多异氰酸酯和多元醇,多异氰酸酯和多胺,以及多环氧化物和多胺。特别优选作为壁单体的是烯属不饱和单体,以及烯属不饱和单体和多异氰酸酯。特别优选作为壁单体的是烯属不饱和单体。
合适的烯属不饱和单体是可自由基聚合的单体,其具有至少一个、优选一个碳-碳双键。优选的烯属不饱和单体是(甲基)丙烯酸、(甲基)丙烯酸酯、(甲基)丙烯酰胺或乙烯基内酰胺,尤其是(甲基)丙烯酸、(甲基)丙烯酸酯或(甲基)丙烯酰胺。可以提到例如:丙烯酸及其酯,甲基丙烯酸及其酯,马来酸及其酯,苯乙烯,丁二烯,异戊二烯,乙酸乙烯酯,丙酸乙烯酯,乙烯基吡啶,氯乙烯,偏二氯乙烯,丙烯腈,甲基丙烯酰胺,衣康酸,马来酸酐,N-乙烯基吡咯烷酮,丙烯酰氨基-2-甲基丙磺酸,N-羟甲基丙烯酰胺,N-羟甲基甲基丙烯酰胺,甲基丙烯酸二甲基氨基乙基酯和甲基丙烯酸二乙基氨基乙基酯。优选的丙烯酸酯或甲基丙烯酸的酯是C1-C24-烷基酯,尤其是羟基官能的烷基酯,尤其是羟基官能的C2-C6-烷基酯,例如丙烯酸2-羟基乙基酯,甲基丙烯酸2-羟基乙基酯,丙烯酸4-羟基丁基酯,甲基丙烯酸4-羟基丁基酯,丙烯酸2-羟基丙基酯,甲基丙烯酸2-羟基丙基酯,丙烯酸3-羟基丙基酯,甲基丙烯酸3-羟基丙基酯。
在一个优选实施方案中,在水中溶解度为至少5重量%的水溶性烯属不饱和单体是合适的。例子是丙烯酰胺,甲基丙烯酰胺,丙烯酸,甲基丙烯酸,丙烯酰氨基-2-甲基丙磺酸的盐,丙烯酸2-羟基乙基酯,甲基丙烯酸2-羟基乙基酯,丙烯酸4-羟基丁基酯,甲基丙烯酸4-羟基丁基酯,丙烯酸2-羟基丙基酯,甲基丙烯酸2-羟基丙基酯,丙烯酸3-羟基丙基酯或甲基丙烯酸3-羟基丙基酯。非常特别优选的烯属不饱和单体是羟基官能的丙烯酸或甲基丙烯酸C2-C6-烷基酯,以及乙烯基吡咯烷酮,尤其是丙烯酸2-羟基乙基酯,甲基丙烯酸2-羟基乙基酯,丙烯酸4-羟基丁基酯,甲基丙烯酸4-羟基丁基酯,丙烯酸2-羟基丙基酯,甲基丙烯酸2-羟基丙基酯,丙烯酸3-羟基丙基酯或甲基丙烯酸3-羟基丙基酯。
合适的多异氰酸酯是具有至少两个、优选2-4个、特别优选2-3个异氰酸酯基团的脂族和芳族异氰酸酯。多异氰酸酯的例子是芳族异氰酸酯,例如2,4-甲苯二异氰酸酯(2,4-TDI),2,4′-二苯基甲烷二异氰酸酯(2,4′-MDI)和″TDI-混合物″(2,4-甲苯二异氰酸酯和2,6-甲苯二异氰酸酯的混合物)。作为脂族异氰酸酯,可以提到例如:1,4-亚丁基二异氰酸酯,六亚甲基二异氰酸酯(HDI),1,12-十二亚甲基二异氰酸酯,1,10-十亚甲基二异氰酸酯,2-丁基-2-乙基五亚甲基二异氰酸酯,2,4,4-或2,2,4-三甲基六亚甲基二异氰酸酯,异佛尔酮二异氰酸酯(IPDI),2-异氰酸酯基丙基环己基异氰酸酯,2,4′-亚甲基二环己基二异氰酸酯和4-甲基环己烷1,3-二异氰酸酯(H-TDI)。其它合适的多异氰酸酯是低聚异氰酸酯以及它们的混合物。对于低聚异氰酸酯,异氰酸酯基团的数目通常通过NCO含量测定,并且由此计算异氰酸酯基团的平均数。异氰酸酯基团的平均数通常是至少2,优选2-4,特别优选2-3。优选的低聚异氰酸酯是基于上述芳族和/或脂族的多异氰酸酯,尤其是基于二苯基甲烷二异氰酸酯和/或六亚甲基二异氰酸酯。这些低聚异氰酸酯例如可以作为M20S从BASF SE获得。优选的多异氰酸酯是甲苯二异氰酸酯(2,4-TDI),2,4′-二苯基甲烷二异氰酸酯(2,4′-MDI),六亚甲基二异氰酸酯(HDI),异佛尔酮二异氰酸酯(IPDI),以及低聚异氰酸酯。低聚异氰酸酯是特别优选的。
多异氰酸酯可以在不存在或优选在存在至少一种聚氨酯催化剂的情况下制备。在聚氨酯化学中常规使用的所有催化剂例如适合作为聚氨酯催化剂,例如有机胺,尤其是脂族、脂环族或芳族的叔胺,以及路易斯酸有机金属化合物。锡化合物例如是可能作为路易斯酸有机金属化合物的,例如有机羧酸的锡(II)盐,例如乙酸锡(II)、辛酸锡(II)、乙基己酸锡(II)和月桂酸锡(II),以及有机羧酸的二烷基锡(IV)衍生物,例如二乙酸二甲基锡,二乙酸二丁基锡,二丁酸二丁锡,二(2-乙基己酸)二丁锡,二月桂酸二丁锡,马来酸二丁锡,二月桂酸二辛锡和二乙酸二辛锡。也可以使用金属配合物,例如铁、钛、锌、铝、锆、锰、镍和钴的乙酰丙酮酸盐。
合适的多环氧化物是具有至少两个、优选2-3个环氧基团的化合物。这些的例子是衍生自双酚A的环氧化物,例如双酚A-二缩水甘油醚,或被表氯醇取代的双酚或多酚类型的环氧化物(聚合度为1-2的环氧化物,可以作为Epikote E828从Shell公司获得),或四缩水甘油基亚甲基二苯胺(例如LY 1802,来自Ciba)。
此外,含有烯属不饱和单体和多异氰酸酯的组合是优选作为壁单体的。合适的烯属不饱和单体和多异氰酸酯如上所述。优选的用于与多异氰酸酯组合的烯属单不饱和单体是羟基官能的烯属不饱和单体,例如丙烯酸或甲基丙烯酸的羟基官能C2-C6-烷基酯,尤其是丙烯酸2-羟基乙基酯,甲基丙烯酸2-羟基乙基酯,丙烯酸4-羟基丁基酯,甲基丙烯酸4-羟基丁基酯,丙烯酸2-羟基丙基酯,甲基丙烯酸2-羟基丙基酯,丙烯酸3-羟基丙基酯或甲基丙烯酸3-羟基丙基酯。
此外,含有烯属单和多不饱和单体的组合是优选作为壁单体的。术语“烯属单不饱和单体”应当理解为表示具有实际一个可自由基聚合的碳-碳双键的单体。术语“烯属多不饱和单体”应当理解为表示具有至少两个、优选2-3个、尤其2个可自由基聚合的碳-碳双键的单体,这些双键优选是非共轭的。
合适的烯属单不饱和单体是上述在烯属不饱和单体中列出的那些。优选的烯属单不饱和单体是丙烯酸或甲基丙烯酸的羟基官能C2-C6-烷基酯,以及乙烯基吡咯烷酮,尤其是丙烯酸2-羟基乙基酯,甲基丙烯酸2-羟基乙基酯,丙烯酸4-羟基丁基酯,甲基丙烯酸4-羟基丁基酯,丙烯酸2-羟基丙基酯,甲基丙烯酸2-羟基丙基酯,丙烯酸3-羟基丙基酯或甲基丙烯酸3-羟基丙基酯。
合适的烯属多不饱和单体是二醇与丙烯酸或甲基丙烯酸形成的二酯,以及这些二醇的二烯丙基醚和二乙烯基醚。可以提到例如乙二醇二丙烯酸酯,乙二醇二甲基丙烯酸酯,聚亚烷基二醇二(甲基)丙烯酸酯(一般亚乙基和/或亚丙基用做亚烷基),1,3-丁二醇二甲基丙烯酸酯,甲代烯丙基甲基丙烯酰胺,丙烯酸烯丙基酯和甲基丙烯酸烯丙基酯。也合适的是二乙烯基苯,三乙烯基苯和二乙烯基环己烷和三乙烯基环己烷,多元醇与丙烯酸和/或甲基丙烯酸的聚酯,以及这些多元醇的聚烯丙基醚和聚乙烯基醚。优选丙二醇、丁二醇、戊二醇和己二醇的二丙烯酸酯,以及相应的甲基丙烯酸酯,三羟甲基丙烷三丙烯酸酯和三甲基丙烯酸酯,季戊四醇三烯丙基醚,季戊四醇四烯丙基醚,季戊四醇三丙烯酸酯和季戊四醇四丙烯酸酯,或相应的甲基丙烯酸酯,以及它们的工业混合物。特别优选丙二醇、丁二醇、戊二醇和己二醇的二丙烯酸酯和相应的甲基丙烯酸酯。
优选的含有烯属单和多不饱和单体的组合是(甲基)丙烯酸2-羟基乙基酯和季戊四醇三丙烯酸酯;(甲基)丙烯酸2-羟基乙基酯和丁二醇二(甲基)丙烯酸酯;以及(甲基)丙烯酸2-羟基乙基酯和聚亚烷基二醇二(甲基)丙烯酸酯。
此外,含有多异氰酸酯和多元醇的组合优选作为壁单体。合适的多异氰酸酯如上所述。合适的多元醇是具有至少两个醇基团的醇,例如乙二醇、二甘醇,1,2-或1,3-丙二醇,双丙甘醇,1,4-丁二醇,1,5-戊二醇,1,6-己二醇,1,10-癸二醇,甘油和三羟甲基丙烷,此外还有二醇,其含有芳族或脂族环体系,例如1,4-双二羟基甲基苯或1,4-双二羟基乙基苯。另外可以使用来自内酯的聚酯多元醇,例如己内酯,或羟基羧酸,例如羟基己酸。也可以使用具有至少两个醇基团的聚合物,例如聚乙烯醇或部分水解的聚乙酸乙烯酯。上述多元醇的混合物也是可能的。优选的多元醇是二甘醇、1,4-丁二醇、1,5-戊二醇和1,6-己二醇。
此外,含有多异氰酸酯和多胺的组合优选作为壁单体。合适的多异氰酸酯如上所述。具有至少两个、优选2-4个、尤其是2-3个氨基的化合物可以用做多胺。可能的多胺优选是脂族的伯多胺和仲多胺。可以提到例如:1,2-亚乙基二胺,二亚乙基三胺,三亚乙基四胺,二(3-氨基丙基)胺,二(2-甲基氨基乙基)甲基胺,1,4-二氨基环己烷,3-氨基甲基氨基丙烷,N-甲基-二(3-氨基丙基)胺,1,4-二氨基正丁烷,1,6-二氨基正己烷,聚乙烯基胺或氨基封端的聚醚。优选的多胺是1,2-亚乙基二胺、二亚乙基三胺和三亚乙基四胺。
此外,含有多环氧化物和多胺的组合优选用做壁单体。合适的多环氧化物和多胺如上所述。
壁单体的用量一般按照壁单体与聚酯单体之间的重量比为1∶5至10∶1使用,优选1∶3至7∶1,特别优选1∶1至4∶l。
本发明制备含有有效化合物的微粒M的方法包括A)在含有酶、有效化合物和聚酯单体的反相微乳液中通过酶催聚酯合成形成微粒A的粗悬浮液;和B)使选自烯属不饱和单体、多异氰酸酯和/或多环氧化物的壁单体在微粒A的粗悬浮液中聚合。阶段A)和B)通常按照所述顺序进行。
在阶段A)中,微粒A的粗悬浮液是通过在含有酶、有效化合物和聚酯单体的反相微乳液中通过酶催聚酯合成形成的。一般而言,在此方面,至少一种分散剂、至少一种非极性液体、至少一种极性液体、至少一种聚酯单体、至少一种能催化聚合反应的酶和至少一种有效化合物按照任何顺序混合在一起并由其制备反相微乳液。也可以制备各组分的预混物。优选,至少一种能能催化聚酯单体的聚合反应的酶被引入预先制备的反相微乳液中。
本发明方法优选进行使得至少一种分散剂被引入至少一部分液体和至少一部分聚酯单体中。有效化合物和一部分聚酯单体被单独地引入至少一部分液体中。两种混合物混合在一起并制备反相微乳液。随后,聚酯单体的部分以及酶被引入微乳液中。术语“聚酯单体的部分”表示在反应物料中存在的全部聚酯单体的0-100%。术语“至少一部分”表示在总物料中存在多于0%的量。在一个优选实施方案中,聚酯单体的一部分被引入微乳液中,此部分是多于1%,优选多于10%。
额外的添加剂,例如防腐剂,可以在任何工艺阶段中引入。
本发明方法一般在5-100℃的反应温度下进行,通常是20-80℃,经常是30-65℃。通常,此方法在一般0.8-10巴的压力(绝对值)下进行,优选0.9-2巴,尤其是1巴(大气压)。本领域技术人员根据微粒的所需性能选择反应时间,例如聚合度。在所需的反应时间之后,酶可以被破坏或再利用,微粒可以分离或反应混合物可以分离或再加工。优选,微粒A的粗悬浮液直接用于阶段B)。
根据本发明必须存在的反相微乳液可以按照现有技术制备。为此,粗乳液是通过将能量引入各阶段的混合物中制备的,这通过以下措施进行:通过振动、击打、搅拌或湍流混合;通过将一种液体注射入另一种液体中;通过在混合物中振动和空穴化(例如超声波);通过乳化离心;通过胶体磨和均化器;或通过排料喷嘴,例如参见WO2006/053712。粗乳液是通过均化被转化成液滴尺寸小于1000nm的微乳液。均化优选在0-100℃下通过使用超声波、高压均化器或其它高能均化设备进行,例如排料喷嘴。
通常,固体微粒是从聚酯单体在反应时间期间在酶的催化下在反相微乳液中形成的。通过形成固体微粒,从反相微乳液形成微粒A的粗悬浮液。
在阶段B)中,选自烯属不饱和单体、多异氰酸酯和/或多环氧化物的壁单体是在微粒A的粗悬浮液中聚合的。优选,至少一种壁单体被引入预先制备的微粒A的粗悬浮液中,然后聚合。特别优选,至少一种壁单体和至少一种分散剂被加入粗悬浮液中。壁单体可以按照常规方式聚合,例如通过聚合催化剂或物理方法。如果壁单体含有烯属不饱和单体,则通常加入自由基引发剂作为聚合催化剂和/或提高反应温度。如果壁单体含有多异氰酸酯,则通常上述聚氨酯催化剂作为聚合催化剂加入。
阶段B)优选进行使得来自阶段A)的粗悬浮液用至少一种分散剂和至少一种壁单体处理。优选,粗悬浮液用含有壁单体和分散剂的乳液处理。优选,在此方面,壁单体的乳液是在微粒A的粗悬浮液中形成的。随后,加入至少一种聚合催化剂。壁单体、分散剂和聚合催化剂可以一次加入、分多份加入或连续地加入。壁单体、分散剂和聚合催化剂可以在加入粗悬浮液之前溶解或分散在极性或非极性溶剂中。
在另一个优选实施方案中,至少一种壁单体已经加入阶段A)中,并仅仅在阶段B)期间聚合。优选,为此目的使用不带任何伯羟基或仲羟基的壁单体。不带任何伯羟基或仲羟基的烯属不饱和单体是特别合适的。
本发明方法一般在20-120℃的反应温度下进行,通常是40-90℃,经常是50-80℃。一般,此方法在通常0.8-10巴的压力(绝对值)下进行,优选0.9-2巴,尤其是1巴(大气压)。本领域技术人员将根据微粒的所需性能来选择反应时间,例如聚合度。反应物料通常例如通过连续搅拌来混合。
通常,在阶段B)中,含有有效化合物的微粒M是从微粒A和已聚合的壁单体形成的。另外,在阶段B)中,基于所有微粒的总量计,小比例、优选小于20重量%、尤其小于5重量%的非本发明的微粒可以仅仅从聚合的壁单体制备。这种二次成核是扩展的副反应,本领域技术人员能通过常规措施减少这种副反应,例如通过缓慢计量加入壁单体,或降低壁单体在连续相中的浓度。
在没有进一步再加工的情况下进一步使用微粒M是可能的。在根据本发明制备微粒之后,需要时可以分离它们,使其脱除溶剂。合适的方法是例如蒸发、喷雾干燥、冷冻干燥、离心、过滤或真空干燥。在一个优选实施方案中,微粒在制备后是不分离的。
此外,微粒M可以被转化成本发明的分散体,其中微粒分散在水或水溶液中,例如通过相转移方法或与冲洗类似的转移方法,或优选通过将粒子干燥成粉末,这随后再分散。
根据本发明制备的含有微粒M的分散体或其它再加工产物可以在以下物质中用做组分:着色剂、化妆品、药物、植物保护剂、肥料,用于食品或动物饲料的添加剂,或用于聚合物、纸、织物、皮革、涂料、洗涤剂或清洁剂的助剂。有利的是,有效化合物能选择性地再释放,尤其在生物界中,其中聚酯分解酶是普遍存在的。
在一个优选实施方案中,本发明涉及一种农业化学配料,其含有本发明的微粒M或根据本发明制备的微粒M。
农业化学配料可以包含额外的配制助剂。术语“配制助剂”在本发明内表示适用于配制农业化学活性化合物的助剂,例如溶剂、载体、表面活性剂(离子性或非离子性的表面活性剂、助剂、分散剂),防腐剂,防泡剂,和/或防冻剂。用于种子处理的助剂可以任选地也是染料、粘合剂、胶凝剂和/或增稠剂。
一般,农业化学配料可以含有0-90重量%、优选1-85重量%、特别优选5-80重量%和尤其是5-65重量%的配制助剂。
此外,本发明涉及一种抵抗不需要的植物生长的方法,其中不需要的植物、其中生长不需要的植物的土壤或它们的种子用本发明的农业化学配料处理。
另外,本发明涉及一种抵抗不需要的昆虫或螨虫对植物的侵害的方法和/或抵抗植物病菌的方法,其中用根据本发明的配料处理真菌/昆虫、它们的栖息地或要防止真菌或昆虫感染的植物或土壤、或植物、其中生长所述植物的土壤或它们的种子。
另外,本发明涉及一种用本发明农业化学配料处理种子的方法,以及涉及用本发明配料处理的种子。
总之,本发明的方法与常规制备微粒的方法相比具有许多优点:较低的反应温度和大部分中性的pH允许使用对温度和pH敏感的有效化合物;微粒的聚合物可以直接在现场制备且不需要进行昂贵的储存。
同样,根据本发明制备的微粒具有以下优点:所述微粒比其它制备方法中更稠密。尤其是,微粒在机械上比仅仅酶催制备的微粒更稳定。微粒可以含有易受温度影响或其它敏感性的有效化合物;它们也可以含有溶解在极性液体中的有效化合物。此外,有效化合物从微粒释放的速率可以用壁单体的类型和/或用量控制。与仅仅从聚酯制备的粒子相比,释放速率有利地通过壁单体的聚合减慢。
以下实施例用于说明本发明,但不限制它。
实施例
部分氢化的石油馏出物:沸点为260-280℃的部分氢化的石油馏出物,例
酶:南极洲假丝酵母类型B(Candida antarctica type B)的脂酶,固定在
分散剂:聚酯/聚氧化乙烯/聚酯嵌段共聚物,具有>1000g/mol的摩尔质量,从缩合的12-羟基硬脂酸与聚氧化乙烯的反应按照EP 424B1的教导
制备(作为B-246从Croda获得)。
己内酯:ε-己内酯,纯度>99%.
HEMA:甲基丙烯酸2-羟基乙基酯,从BASF SE获得。
AIBN:偶氮二异丁腈
DBTL:二月桂酸二丁锡
异氰酸酯A:低聚的4,4′-二苯基甲烷二异氰酸酯,NCO含量为31.8g/100g(ASTM D 5155-96A),酸度为150mg/kg(作为HCl,ASTM D 1638-74),并且粘度为210mPa.s(DIN 53018),例如作为M20S从BASF SE获得。
作为有效化合物,使用杀菌植物保护剂,例如灭菌唑。或者,着色剂用做有效化合物,例如蓝756(C.I.酸性蓝9,三苯基甲烷染料,例如从BASF SE获得)。Basacid蓝756不溶于V中,但能溶解在碳酸亚丙酯和己内酯中。作为另外的选择,碳酸亚丙酯用做有效化合物。
实施例1(不是根据本发明)
以下量用于制备反相微乳液:
120g的部分氢化的石油馏出物
24.0g的碳酸亚丙酯
6.0g的ε-己内酯
19.2mg的D-山梨醇
1.65g的灭菌唑
3.0g的分散剂
0.6g的酶
将分散剂引入样品容器中,并在搅拌下溶解在部分氢化的石油馏出物中。灭菌唑和D-山梨醇在另外的容器中溶解于己内酯和碳酸亚丙酯的混合物中。这些均匀溶液然后彼此混合,并通过用磁力搅拌器在环境温度下搅拌60分钟来预先乳化。由此使用超声波制备反相微乳液(超声波处理器UP400S,来自Hielscher),同时用冰浴冷却(5分钟,100%,具有SonotrodeH7),并且在加入100mg酶之后,在60℃下聚合48小时。获得了微粒的粗悬浮液。
完整的球形粒子显示在光谱照片(1000倍放大)中(图1)。
为了准备SEM(扫描电子显微镜)照片,所获得的产物进行离心,固体用异丁醇和己烷洗涤,并在空气中干燥。在5.00kV下的SEM照片显示大部分分解的微粒(图2)。
实施例2:用300%甲基丙烯酸羟基乙基酯(HEMA)聚合
微粒的粗悬浮液先如实施例1所述制备。然后加入3.6g分散剂,并将此混合物搅拌15分钟。在分散剂完全溶解在油相中之后,加入18.0gHEMA并将混合物再搅拌30分钟。聚合反应随后通过加入72g Isopar V和0.36gAIBN的混合物来引发。为了保证完全的转化,在60℃下反应6小时之后再次加入在24g Isopar V中的相同量的AIBN,并且聚合继续进行直到转化完全。
为了准备SEM(扫描电子显微镜)照片,如此获得的产物如实施例1所述进行离心,如此获得的固体用异丁醇和己烷洗涤,并在空气中干燥。干燥的固体随后在研钵中精细研磨得到粉末。SEM照片显示完整的球形微粒(图3)。
为了另外监控粒子的稳定性,使用超声波(1分钟,使用冰冷却,100%具有Sonotrode H7)将粉末再分散在1重量%SDS水溶液中。在光谱照片中显示完整的球形粒子(1000倍放大)。
实验研究显示了高的机械稳定性,尤其是与实施例1的粒子相比。
实施例3:用200%甲基丙烯酸羟基乙基酯聚合
微粒的粗悬浮液先如实施例1所述制备。然后加入2.4g分散剂,并将此混合物搅拌15分钟。在分散剂完全溶解在油相中之后,加入12.0gHEMA并将混合物再搅拌30分钟。聚合反应随后通过加入24g部分氢化的石油馏出物和0.24g AIBN的混合物来引发。为了保证完全的转化,在60℃下反应6小时之后再次加入在24g部分氢化的石油馏出物中的相同量的AIBN,并且聚合继续进行直到转化完全。为了准备SEM照片,如此获得的产物如实施例2所述准备。SEM照片显示完整的球形微粒。
实施例4:用3次100%甲基丙烯酸羟基乙基酯聚合
微粒的粗悬浮液先如实施例1所述制备。然后加入1.2g分散剂,并将此混合物搅拌15分钟。在分散剂完全溶解在油相中之后,加入6.0gHEMA并将混合物再搅拌30分钟。聚合反应随后通过加入24g部分氢化的石油馏出物和0.12g AIBN的混合物来引发。在60℃下反应6小时之后,加入6.0g的HEMA,在另外20小时之后加入另外6.0g的HEMA,在每种情况下与1.2g分散剂和在24g Isopar V中的0.12g AIBN的添加一起进行。在最后一次HEMA添加之后,聚合在60℃下继续12小时,直到转化完全。为了准备SEM照片,如此获得的产物如实施例2所述准备。SEM照片显示完整的球形微粒。
实施例5:不含碳酸亚丙酯的粒子,用300%HEMA聚合
以下量用于制备反相微乳液:
114.0g的部分氢化的石油馏出物
30.0g的ε-己内酯
96mg的D-山梨醇
0.82g的灭菌唑
6.0g的分散剂
3.0g的Novozym 435
将分散剂引入样品容器中,并在搅拌下溶解在部分氢化的石油馏出物中。灭菌唑在另外的容器中溶解于己内酯和山梨醇的混合物中。这些均匀溶液然后彼此混合,并通过用磁力搅拌器(在环境温度下搅拌60分钟)搅拌来预先乳化。由此使用超声波制备反相微乳液(超声波处理器UP400S,来自Hielscher),同时用冰浴冷却(5分钟,100%,具有Sonotrode H7),并且在加入酶之后,在60℃下聚合48小时。
所获得的93.0g产物随后用10.8g分散剂处理,并将此混合物搅拌15分钟。在分散剂完全溶解在油相中之后,加入54.0g的HEMA并将混合物再搅拌30分钟。聚合反应随后通过添加50g Isopar V和1.1g AIBN的混合物来引发。为了保证完全的转化,在60℃下反应6小时之后再次加入在50gIsopar V中的相同量的AIBN,并且聚合继续进行12小时直到转化完全。为了准备SEM照片,如此获得的产物如实施例2所述准备。SEM照片显示完整的球形微粒。
实施例6:用300%HEMA和异氰酸酯A聚合
将在实施例5中获得的237.5g最终产物在搅拌下用13.7g异氰酸酯A处理。在添加作为催化剂的DBTL之后,将反应混合物于60℃搅拌4小时,直到转化完全(通过FTIR监控反应)。为了准备SEM照片,如此获得的产物如实施例2所述准备。SEM照片显示完整的球形微粒。
实施例7:用HEMA和异氰酸酯A聚合-NCO/OH比率
在此实施例中,HEMA的OH基团用异氰酸酯A按照不同的OH/NCO比率交联。
将在实施例2中获得的30.0g最终产物用异氰酸酯A处理,并在用磁力搅拌器搅拌的同时加热到60℃。在添加作为催化剂的0.01g DBTL之后,将反应混合物搅拌过夜,直到NCO转化完全。
异氰酸酯A的用量:
a)0.5g(对应于NCO/OH=0.25)
b)1.02g(对应于NCO/OH=0.5)
c)1.52g(对应于NCO/OH=0.75)
b)2.03g(对应于NCO/OH=1.0)
为了准备SEM照片,如此获得的产物在每种情况下如实施例2所述准备。SEM照片显示完整的球形微粒。
Claims (14)
1.一种制备含有有效化合物的微粒M的方法,此方法包括:
A)在含有酶、有效化合物和聚酯单体的反相微乳液中通过酶催聚酯合成形成微粒A的粗悬浮液;和
B)使选自烯属不饱和单体、多异氰酸酯和多环氧化物的壁单体在微粒A的粗悬浮液中聚合。
2.权利要求1的方法,其中作为壁单体使用:
烯属不饱和单体;
烯属不饱和单体和多异氰酸酯;
烯属单不饱和单体和烯属多不饱和单体;
多异氰酸酯和多元醇;
多异氰酸酯和多胺;或
多环氧化物和多胺。
3.权利要求1或2的方法,其中作为壁单体使用:
烯属不饱和单体;或
烯属不饱和单体和多异氰酸酯。
4.权利要求1-3中任一项的方法,其中作为烯属不饱和单体,使用(甲基)丙烯酸、(甲基)丙烯酸酯或(甲基)丙烯酰胺。
5.权利要求1-4中任一项的方法,其中作为多异氰酸酯,使用芳族或脂族的具有2-3.5平均官能度的多异氰酸酯。
6.权利要求1-5中任一项的方法,其中作为聚酯单体,使用羟基酸。
7.权利要求1-6中任一项的方法,其中有效化合物是着色剂,化妆品,药物,杀微生物剂,植物保护剂,农业化学助剂,肥料,用于食品或动物饲料的添加剂,或者用于聚合物、纸、织物、皮革、洗涤剂或清洁剂的助剂。
8.权利要求1-7中任一项的方法,其中有效化合物是植物保护剂或肥料。
9.一种微粒M,其可以通过权利要求1-8中任一项的方法获得。
10.可以通过权利要求1-10中任一项的方法获得的微粒M作为组分用于以下物质中的用途:着色剂,化妆品,药物,植物保护剂,肥料,用于食品或动物饲料的添加剂,或者用于聚合物、纸、织物、皮革、洗涤剂或清洁剂的助剂。
11.一种农业化学配料,其含有根据权利要求9的或根据权利要求1-8中任一项的方法制备的微粒M。
12.一种抵抗不需要的植物生长的方法,其中不需要的植物、其中生长不需要的植物的土壤或它们的种子用根据权利要求11的配料处理。
13.一种抵抗不需要的昆虫或螨虫对植物的侵害的方法和/或抵抗植物病菌的方法,其中用根据权利要求11的配料处理真菌/昆虫、它们的栖息地或要防止真菌或昆虫侵害的植物或土壤、或植物、其中生长所述植物的土壤或它们的种子。
14.一种种子,其经过用根据权利要求11的配料处理。
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- 2009-10-14 EP EP09821620A patent/EP2352580A1/de not_active Withdrawn
- 2009-10-14 JP JP2011532593A patent/JP2012508090A/ja active Pending
- 2009-10-14 CN CN2009801521770A patent/CN102264464A/zh active Pending
- 2009-10-14 WO PCT/EP2009/063379 patent/WO2010046286A1/de active Application Filing
- 2009-10-14 BR BRPI0919589A patent/BRPI0919589A2/pt not_active IP Right Cessation
- 2009-10-14 US US13/125,388 patent/US20110230343A1/en not_active Abandoned
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CN1150764A (zh) * | 1994-06-06 | 1997-05-28 | 拜奥波尔公司 | 聚合物微球及其制造方法 |
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CN1396841A (zh) * | 2000-01-27 | 2003-02-12 | 西巴特殊化学水处理有限公司 | 微粒组合物及其制造方法 |
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113164897A (zh) * | 2018-10-30 | 2021-07-23 | 巴斯夫欧洲公司 | 制备被活性材料填充的微粒的方法 |
CN111454959A (zh) * | 2020-03-31 | 2020-07-28 | 山西大学 | 一种飞蝗Spinless基因dsRNA及其应用 |
CN111454959B (zh) * | 2020-03-31 | 2021-09-28 | 山西大学 | 一种飞蝗Spinless基因dsRNA及其应用 |
CN115024339A (zh) * | 2022-05-16 | 2022-09-09 | 江苏大学 | 一种植物源纳米农药微胶囊制备方法 |
Also Published As
Publication number | Publication date |
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WO2010046286A1 (de) | 2010-04-29 |
EP2352580A1 (de) | 2011-08-10 |
US20110230343A1 (en) | 2011-09-22 |
BRPI0919589A2 (pt) | 2015-12-08 |
JP2012508090A (ja) | 2012-04-05 |
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