CN102753601A - 用于使难溶性活性成分加溶的烷氧基化超支化聚碳酸酯 - Google Patents
用于使难溶性活性成分加溶的烷氧基化超支化聚碳酸酯 Download PDFInfo
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- CN102753601A CN102753601A CN2010800630665A CN201080063066A CN102753601A CN 102753601 A CN102753601 A CN 102753601A CN 2010800630665 A CN2010800630665 A CN 2010800630665A CN 201080063066 A CN201080063066 A CN 201080063066A CN 102753601 A CN102753601 A CN 102753601A
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- oxyalkylene
- amphiphile
- alkoxylate
- polycarbonate
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Abstract
本发明涉及一种包含在20°C下在水中的溶解度不超过10g/L的活性成分和包含烷氧基化超支化聚碳酸酯的两亲分子的组合物,其中所述聚碳酸酯包含如下醇,所述醇为基于C3-C12氧化烯和具有至少三个OH基团的醇的三官能或高级多官能聚醚醇。本发明进一步涉及一种包含所述聚碳酸酯的两亲分子以及一种生产所述两亲分子的方法。本发明进一步涉及所述两亲分子在水溶液中加溶在20°C下在水中的溶解度不超过10g/L的活性成分的用途以及一种防治植物病原性真菌和/或不希望的植物生长和/或不希望的昆虫或螨虫侵染和/或调节植物生长的方法。
Description
本发明提供了一种包含在20°C下在水中的溶解度不超过10g/L的活性成分和包含烷氧基化超支化聚碳酸酯的两亲分子的组合物,其中所述聚碳酸酯包含醇(B1),所述醇(B1)为基于C3-C12氧化烯和具有至少三个OH基团的醇的三官能或高级多官能聚醚醇(polyetherol)。同样提供了一种包含所述聚碳酸酯的两亲分子以及一种制备所述两亲分子的方法。本发明进一步涉及所述两亲分子在水溶液中加溶在20°C下在水中的溶解度不超过10g/L的活性成分的用途以及一种防治植物病原性真菌和/或不希望的植物生长和/或不希望的昆虫或螨虫侵染和/或调节植物生长的方法。本发明包括优选特征与其他优选特征的组合。
许多情形要求在水中加溶疏水性活性成分而不对所述活性成分本身引起任何化学变化。为此,例如可以制备乳液,其中所述活性成分位于该乳液的油相中。然而,对于许多药物活性成分或作物保护剂,尤其是要随体液输送或在植物汁液中输送的那些,这类程序是不可能的。在高剪切力的作用下,乳液可能破乳。此外,在维持该乳液的同时灭菌在许多情况下是不可能的。
包含两亲分子和微溶性活性成分的组合物是公知常识:
WO 2007/125028公开了一种使用作为助剂的超支化聚合物在含水介质中加溶疏水性活性成分的方法,该聚合物可以通过制备基于二羧酸、三羧酸或四羧酸和二醇或三醇的超支化聚酯并使该聚酯与聚氧化烯单元反应而得到。
WO 2009/021986公开了一种包含活性成分和超支化聚合物的种子包衣剂,所述聚合物例如可以为超支化聚碳酸酯。
用于在含水介质中加溶疏水性活性成分的已知两亲分子的缺点是它们仅能加溶少量活性成分。此外,两亲分子本身通常不是水溶性的或水分散性的并且因此不适合在含水介质中加溶。此外,含有聚酯的两亲分子具有的缺点是它们本身在一些情况下对水解敏感,特别是由于存在的酸端基。
聚碳酸酯通常由醇或酚与光气的反应或者醇或酚与碳酸二烷基或二芳基酯的反应得到。工业上重要的是例如由双酚制备的芳族聚碳酸酯;就市场量而言,脂族聚碳酸酯在当前仅占小部分。文献中所述芳族或脂族聚碳酸酯通常具有线性结构或者仅以低支化度构成。然而,超支化聚碳酸酯也是公知常识:WO 2006/089940公开了可水乳化的超支化聚碳酸酯,其至少部分直接与单官能聚氧化烯聚醚醇反应。
本发明的目的是找到适合在含水介质中加溶微溶性活性成分的替代两亲分子。另一目的是找到一种能够加溶非常大量的活性成分,尤其是农业化学活性成分的两亲分子。此外,该两亲分子本身应是水溶性的或水分散性的。最后,另一目的是找到一种与聚酯相比对水解不太敏感的两亲分子。
该目的借助包含在20°C下在水中的溶解度不超过10g/L的活性成分和包含烷氧基化超支化聚碳酸酯的两亲分子的组合物实现,其中所述聚碳酸酯包含醇(B1),所述醇(B1)为基于C3-C12氧化烯和具有至少三个OH基团的醇的三官能或高级多官能聚醚醇。
活性成分在20°C下在水中的溶解度不超过10g/L,优选不超过2g/l,更优选不超过0.5g/l,尤其不超过0.1g/l。该组合物可以包含一种或多种不同的活性成分。活性成分的实例是农业化学活性成分、化妆品活性成分、药物活性成分或营养增补剂(如维生素和类胡萝卜素)。优选的活性成分为农业化学活性成分。
化妆品活性成分的实例是化妆品用油、增味剂和香料、维生素或UV吸收剂。化妆品用油包括花生油、霍霍巴油、椰子油、杏仁油、橄榄油、棕榈油、蓖麻油、大豆油、小麦胚芽油或精油如矮松油、薰衣草油、迷迭香油、云杉针叶油、松针油、桉树油、薄荷油、鼠尾草油、香柠檬油、松节油、蜂花油、刺柏油、柠檬油、茴香油、小豆蔻油、樟脑油等,或它们的混合物。UV吸收剂包括2-羟基-4-甲氧基二苯甲酮、2,2',4,4'-四羟基二苯甲酮、2,2'-二羟基-4,4'-二甲氧基二苯甲酮、2,4-二羟基二苯甲酮、2-氰基-3,3-二苯基丙烯酸2'-乙基己基酯、2,4,6-三苯胺基-对-(2'-乙基己基-1'-氧羰基)-1,3,5-三嗪、3-(4-甲氧基亚苄基)樟脑、N,N-二甲基-4-氨基苯甲酸2-乙基己基酯、水杨酸3,3,5-三甲基环己基酯、4-异丙基二苯甲酰基甲烷、对甲氧基肉桂酸2-乙基己基酯和对甲氧基肉桂酸2-异戊基酯,以及它们的混合物。
增味剂和香料的实例如在本文作为参考引入的WO 01/49817或“Flavors and Fragrances”,Ullmann's Encyclopedia of IndustrialChemistry,Wiley-VCH,2002中所述。
维生素的实例是A、C、E和F组维生素、维生素原和维生素前体,更具体为3,4-脱氢维生素A,β-胡萝卜素(维生素A的维生素原)、抗坏血酸(维生素C),以及抗坏血酸的棕榈酸酯、葡糖苷或磷酸酯,生育酚,更具体为α-生育酚及其酯,如乙酸酯、烟酸酯、磷酸酯和琥珀酸酯;以及还有维生素F,其应理解为指必需脂肪酸,特别是亚油酸、亚麻酸和花生四烯酸。
药物活性成分的实例包括下列:苯并二氮杂类,抗高血压药,维生素,细胞抑制剂,尤其是紫杉酚,麻醉药,抗精神病药,抗抑郁药,抗病毒药,如抗HIV药,抗生素,抗真菌药,抗痴呆药,杀真菌剂,化疗药,泌尿用药,血小板聚集抑制剂,磺酰胺类,解痉药,激素,免疫球蛋白,血清,甲状腺治疗药,精神活性药物,抗帕金森药和其他抗运动机能亢进药,眼科用药,神经病变用药,钙代谢调节剂,肌肉松弛剂,麻醉药,降脂药,肝病治疗药,冠心病药,强心药,免疫治疗药,调节肽及其抑制剂,催眠药,镇静药,妇科用药,痛风治疗药,纤维蛋白溶解药,酶制剂和转运蛋白,酶抑制剂,催吐药,血流刺激药,利尿药,诊断助剂,皮质激素类,胆碱能药,胆道治疗药,抗哮喘药,支气管扩张药,β受体阻断剂,钙拮抗剂,ACE抑制剂,动脉硬化治疗药,抗炎药,抗凝血药,抗低血压药,抗低血糖药,抗高血压药,抗纤溶药,抗癫痫药,止吐药,解毒药,抗糖尿病药,抗心律失常药,抗贫血药,抗过敏药,驱肠虫药,镇痛药,回苏剂,醛固酮拮抗剂,减肥药。
术语“农业化学活性成分”(下文也称为农药)是指至少一种选自杀真菌剂、杀虫剂、杀线虫剂、除草剂、安全剂和/或生长调节剂的活性成分。优选的农药是杀真菌剂、杀虫剂和除草剂,尤其是杀虫剂。还可以使用两种或更多种上述种类农药的混合物。熟练技术人员熟知该类农药,例如可以在Pesticide Manual,第14版(2006),The British Crop ProtectionCouncil,London中找到。合适的杀虫剂是选自如下类别的杀虫剂:氨基甲酸酯类、有机磷酸酯类、有机氯杀虫剂、苯基吡唑类、合成除虫菊酯类、新类烟碱类、斯皮诺素类(spinosins)、阿维菌素类(avermectins)、米尔霉素类(milbemycins)、保幼激素类似物、烷基卤、有机锡化合物、沙蚕毒素类似物、苯甲酰脲类、二酰基肼类、METI杀螨剂以及杀虫剂如氯化苦(chloropicrin)、拒嗪酮(pymetrozine)、氟啶虫酰胺(flonicamid)、四螨嗪(clofentezine)、噻螨酮(hexythiazox)、特苯唑(etoxazole)、杀螨硫隆(diafenthiuron)、克螨特(propargite)、三氯杀螨砜(tetradifon)、氟唑虫清(chlorfenapyr)、二硝酚(DNOC)、噻嗪酮(buprofezine)、灭蝇胺(cyromazine)、双甲脒(amitraz)、灭蚁腙(hydramethylnon)、灭螨醌(acequinocyl)、fluacrypyrim、鱼藤酮(rotenone)或其衍生物。合适的杀真菌剂是选自如下类别的杀真菌剂:二硝基苯胺类、烯丙基胺类、苯胺基嘧啶类、抗生素类、芳族烃类、苯磺酰胺类、苯并咪唑类、苯并异噻唑类、二苯甲酮类、苯并噻二唑类、苯并三嗪类、苄基氨基甲酸酯类、氨基甲酸酯类、羧酰胺类、羧酸酰胺类、氯代腈类、氰基乙酰胺肟类、氰基咪唑类、环丙烷羧酰胺类、二羧酰亚胺类、二氢二嗪类、二硝基苯基巴豆酸酯类、二硫代氨基甲酸酯类、二硫戊环类、乙基膦酸酯类、乙基氨基噻唑羧酰胺类、胍类、羟基-(2-氨基-)嘧啶类、羟基酰替苯胺类、咪唑类、咪唑啉酮类、无机物质、异苯并呋喃酮类、甲氧基丙烯酸酯类、甲氧基氨基甲酸酯类、吗啉类、N-苯基氨基甲酸酯类、唑烷二酮类、肟基乙酸酯类、肟基乙酰胺类、肽基嘧啶核苷、苯基乙酰胺类、苯基酰胺类、苯基吡咯类、苯基脲类、膦酸酯类、硫代磷酸酯类、邻氨甲酰苯甲酸类、苯邻二甲酰亚胺类、哌嗪类、哌啶类、丙酰胺类、哒嗪酮类、吡啶类、吡啶基甲基苯甲酰胺类、嘧啶胺类、嘧啶类、嘧啶酮腙类、吡咯并喹啉酮类、喹唑啉酮类、喹啉类、醌类、磺酰胺类、氨磺酰三唑类、噻唑羧酰胺类、硫代氨基甲酸酯类、托布津类(thiophanates)、噻吩羧酰胺类、甲苯甲酰胺类、三苯基锡化合物、三嗪类、三唑类。合适的除草剂是选自如下类别的除草剂:乙酰胺类、酰胺类、芳氧基苯氧基丙酸酯类、苯甲酰胺类、苯并呋喃、苯甲酸类、苯并噻二嗪酮类、联吡啶氨基甲酸酯类、氯代乙酰胺类、氯代羧酸、环己烷二酮类、二硝基苯胺类、二硝基苯酚类、二苯基醚类、甘氨酸类、咪唑啉酮类、异唑类、异唑烷酮类、腈类、N-苯基苯邻二甲酰亚胺类、二唑类、唑烷二酮类、羟乙酰胺类、苯氧基羧酸类、苯基氨基甲酸酯类、苯基吡唑类、苯基吡唑啉类、苯基哒嗪类、次膦酸类、氨基磷酸酯类、二硫代磷酸酯类、邻氨甲酰苯甲酸酯类、吡唑类、哒嗪酮类、吡啶类、吡啶羧酸类、吡啶羧酰胺类、嘧啶二酮类、嘧啶基(硫代)苯甲酸酯类、喹啉羧酸类、缩氨基脲类、磺酰氨基羰基三唑啉酮类、磺酰脲类、四唑啉酮类、噻二唑类、硫代氨基甲酸酯类、三嗪类、三嗪酮类、三唑类、三唑啉酮类、三唑并羧酰胺类、三唑并嘧啶类、三酮类、尿嘧啶类、脲类。
在一个实施方案中,该农药包括杀虫剂,优选该农药由至少一种杀虫剂构成。优选的杀虫剂是锐劲特(fipronil)、丙烯除虫菊(allethrin)、甲体氯氰菊酯(α-cypermethrin)、高效氟氯氰菊酯(β-cyfluthrin)、氟氯菊酯(bifenthrin)、生物烯丙菊酯(bioallethrin)、4-氯-2-(2-氯-2-甲基丙基)-5-[(6-碘-3-吡啶基)甲氧基]-3(2H)-哒嗪酮(CAS RN:120955-77-3)、氟唑虫清、毒死蜱(chlorpyrifos)、氟氯氰菊酯(cyfluthrin)、(RS)氯氟氰菊酯(cyhalothrin)、氯氰菊酯(cypermethrin)、溴氰菊酯(deltamethrin)、醚菊酯(etofenprox)、双氧威(fenoxycarb)、氟虫脲(flufenoxuron)、灭蚁腙、氰氟虫胺(metaflumizone)、氯菊酯(permethrin)、吡丙醚(pyriproxifen)、灭虫硅醚(silafluofen)、虫酰肼(tebufenocide)和四溴菊酯(tralomethrin)。特别优选的杀虫剂是锐劲特、甲体氯氰菊酯、氟氯菊酯、氟唑虫清、氟氯氰菊酯、氯氰菊酯、溴氰菊酯、醚菊酯、灭蚁腙、氰氟虫胺、氯菊酯。尤其优选的杀虫剂是锐劲特、甲体氯氰菊酯、溴氰菊酯、氟唑虫清、灭蚁腙和氰氟虫胺。尤其优选的杀虫剂是锐劲特。在另一实施方案中,该农药包括杀真菌剂,优选该农药由至少一种杀真菌剂构成。优选的杀真菌剂是唑菌胺酯(pyraclostrobin)、环戊唑菌(metconazole)和氧唑菌(epoxiconazole)。在另一实施方案中,该农药包括除草剂,优选该农药由至少一种除草剂构成。在另一实施方案中,该农药包括生长调节剂,优选该农药由至少一种生长调节剂构成。
本发明组合物基于该组合物通常包含0.1-70重量%,优选1-50重量%,更具体3-30重量%的活性成分。
两亲分子通常包含至少一个极性(亲水性)结构部分和至少一个非极性(疏水性)结构部分。典型的两亲分子是脂肪酸、表面活性剂和磷脂类。该组合物可以包含一种或多种不同的两亲分子。该两亲分子优选为烷氧基化超支化聚碳酸酯,其中该聚碳酸酯包含醇(B1),所述醇(B1)为基于C3-C12氧化烯和具有至少三个OH基团的醇的三官能或高级多官能聚醚醇。
超支化聚碳酸酯对本发明而言是指具有羟基和碳酸酯或氨基甲酰氯基团的非交联大分子,其可以在结构和分子二者上不均匀。一方面它们可以以与树枝状聚合物相同的方式由中心分子开始合成,但与后者相反的是具有不均匀链长的支链。因此,超支化聚合物有别于树枝状聚合物(US6,399,048)。对本发明而言,超支化聚合物不包括树枝状聚合物。另一方面,超支化聚合物也可以具有线性结构,具有支化的官能侧基或者作为这两种极端情况的结合可以包括线性和支化的分子结构部分。对于树枝状聚合物和超支化聚合物的定义,还参见P.J.Flory,J.Am.Chem.Soc.1952,74,2718和H.Frey等,Chem.Eur.J.2000,6,2499。
“超支化”就本发明而言是指支化度(DB),换言之每分子中树枝状连接的平均数加上端基平均数的总和与树枝状和线性连接的平均数加上端基平均数的总和之比乘以100为10-99.9%,优选20-99%,更优选20-95%。“树枝状聚合物”就本发而言是指支化度为99.9-100%。对于支化度的定义,参见H.Frey等,Acta Polym.1997,48,30。
本发明的优点是本发明的聚碳酸酯未交联。“未交联”对本说明书而言是指存在的交联度小于15重量%,优选小于10重量%,这经由该聚合物的不溶性部分测定。该聚合物的不溶性部分通过用与测定聚合物的分子量分布的凝胶渗透色谱所用相同的溶剂,即四氢呋喃、二甲基乙酰胺或六氟异丙醇根据何种溶剂对该聚合物具有更好溶解性而在Soxhlet设备中萃取4小时并在将残余物干燥至恒重之后称量剩余的残余物而测定。
该超支化聚碳酸酯通常可以通过如下方式得到:
a)通过使有机碳酸酯(A)或光气衍生物与具有至少三个羟基的醇(B1)反应而制备缩合产物(K),和
b)以分子间方式将K转化成超支化聚碳酸酯,
选择OH基团与碳酸酯或光气基团的定量比以使得K平均具有i)一个碳酸酯或氨基甲酰氯基团和不止一个OH基团或ii)一个OH基团和不止一个碳酸酯基团或氨基甲酰基。该聚碳酸酯优选以此方式得到。
缩合产物(K)可以使用有机碳酸酯(A)或光气衍生物制备。合适的光气衍生物实例是光气、双光气或三光气,优选光气。优选使用有机碳酸酯。
在用作原料的通式RO[(CO)O]nR的有机碳酸酯(A)中的基团R各自相互独立地为具有1-20个碳原子的直链或支化脂族、芳族/脂族(芳脂族)或芳族烃基。这两个基团R还可以相互连接形成环。这两个基团R可以相同或不同;它们优选相同。所述基团优选为脂族烃基,更优选具有1-5个碳原子的直链或支化烷基,或取代或未取代的苯基。此时R为具有1-20个,优选1-12个,更优选1-6个,非常优选1-4个碳原子的直链或支化的,优选直链的(环)脂族、芳族/脂族或芳族烃基,优选(环)脂族或芳族烃基,更优选脂族烃基。该类基团的实例是甲基、乙基、异丙基、正丙基、正丁基、异丁基、仲丁基、叔丁基、正己基、正庚基、正辛基、正癸基、正十二烷基、正十四烷基、正十六烷基、正十八烷基、正二十烷基、2-乙基己基、环戊基、环己基、环辛基、环十二烷基、苯基、邻-或对甲苯基或萘基。优选甲基、乙基、正丁基和苯基。这些基团R可以相同或不同;它们优选相同。基团R还可以相互连接形成环。这类二价基团R的实例是1,2-亚乙基、1,2-亚丙基和1,3-亚丙基。一般来讲,n为1-5,优选1-3,更优选1-2的整数。碳酸酯可以优选为通式RO(CO)OR的简单碳酸酯,即此时n为1。
合适碳酸酯的实例包括脂族、芳族/脂族或芳族碳酸酯,如碳酸亚乙酯、碳酸1,2-或1,3-亚丙酯、碳酸二苯酯、碳酸二-甲苯基酯、碳酸二-二甲苯基酯、碳酸二萘酯、碳酸乙基·苯基酯、碳酸二苄酯、碳酸二甲酯、碳酸二乙酯、碳酸二正丙酯、碳酸二正丁酯、碳酸二异丁酯、碳酸二戊酯、碳酸二己酯、碳酸二环己酯、碳酸二庚酯、碳酸二辛酯、碳酸二癸酯或碳酸二-十二烷基酯。其中n大于1的碳酸酯实例包括二碳酸二烷基酯如二碳酸二叔丁酯,或三碳酸二烷基酯如三碳酸二叔丁酯。一种优选的芳族碳酸酯是碳酸二苯酯。优选脂族碳酸酯,更特别的是其中基团包含1-5个碳原子的那些,如碳酸二甲酯、碳酸二乙酯、碳酸二正丙酯、碳酸二正丁酯或碳酸二异丁酯。尤其优选碳酸二乙酯。
超支化聚碳酸酯通常包含为基于C3-C12氧化烯和具有至少三个OH基团的醇的三官能或更高官能度聚醚醇的醇(B1)。具有至少三个OH基团的合适醇可以是支化或未支化的,取代或未取代的且具有3-26个碳原子。优选脂族醇。具有至少三个OH基团的化合物实例包括甘油、三羟甲基甲烷、三羟甲基乙烷、三羟甲基丙烷(TMP)、二-TMP、三羟甲基丁烷、1,2,4-丁三醇、1,2,3-己三醇、1,2,4-己三醇、三(羟基甲基)胺、三(羟基乙基)胺、(羟基丙基)胺、季戊四醇、二季戊四醇、二甘油、三甘油、聚甘油、异氰脲酸三(羟基甲基)酯、异氰脲酸三(羟基乙基)酯、间苯三酚、三羟基甲苯、三羟基二甲基苯、2,3',4,5',6-五羟基联苯(phloroglucides)、六羟基苯、1,3,5-苯三甲醇、1,1,1-三(4’-羟基苯基)甲烷、1,1,1-三(4’-羟基苯基)乙烷,糖类,如葡萄糖,糖衍生物,如山梨醇、甘露糖醇、二甘油、苏糖醇、赤藓醇、阿东醇(核糖醇)、阿拉伯糖醇(阿糖醇)、木糖醇、卫矛醇(半乳糖醇)、麦芽糖醇、异麦芽酮糖醇或聚酯醇。具有至少三个OH基团的优选醇为甘油、三羟甲基乙烷、三羟甲基丙烷、1,2,4-丁三醇、1,2,3-己三醇、1,2,4-己三醇、季戊四醇,更优选甘油或三羟甲基丙烷。优选的C3-C12氧化烯包括氧化丙烯、氧化丁烯、氧化戊烯及其混合物,更优选氧化丙烯。该三官能或更高官能度聚醚醇通常以聚合形式包含至少3个,优选3-30个,更优选3-20个C3-C12氧化烯分子。特别优选的醇(B1)为基于甘油、三羟甲基乙烷、三羟甲基丙烷、1,2,4-丁三醇和/或季戊四醇和氧化丙烯的三官能聚醚醇,其中该聚醚醇以聚合形式包含至少3个,优选3-30个,更优选3-20个氧化丙烯分子。
以聚合形式存在于该聚醚醇中的C3-C12氧化烯分子可以经由该聚醚醇的一个或多个醇基连接于该聚醚醇。该C3-C12氧化烯分子可以形成一个或多个聚合C3-C12氧化烯分子链。该醇(B1)通常可以通过在该聚醚醇上聚合C3-C12氧化烯分子而得到。结果,C3-C12氧化烯分子通过聚合通常以统计分布连接于该聚醚分子上。
除了醇(B1)外,该聚碳酸酯可以具有二官能醇(B2)作为形成组分,条件是所有一起使用的醇B的平均OH官能度大于2。醇(B1)和(B2)在本文一起称为(B)。合适的二官能醇B2包括二甘醇,三甘醇,1,2-和1,3-丙二醇,二丙二醇,三丙二醇,新戊二醇,1,2-、1,3-和1,4-丁二醇,1,2-、1,3-和1,5-戊二醇,1,6-己二醇,1,2-或1,3-环戊烷二醇,1,2-、1,3-或1,4-环己二醇,1,1-、1,2-、1,3-或1,4-环己烷二甲醇,二(4-羟基环己基)甲烷,二(4-羟基环己基)乙烷,2,2-二(4-羟基环己基)丙烷,1,1’-二(4-羟基苯基)-3,3,5-三甲基环己烷,间苯二酚,氢醌,4,4’-二羟基联苯,二(4-羟基苯基)硫化物,二(4-羟基苯基)砜,二(羟基甲基)苯,二(羟基甲基)甲苯,二(对羟基苯基)甲烷,二(对羟基苯基)乙烷,2,2-二(对羟基苯基)丙烷,1,1-二(对羟基苯基)环己烷,二羟基二苯甲酮,基于氧化乙烯、氧化丙烯、氧化丁烯、氧化戊烯或其混合物的二官能聚醚多元醇,摩尔质量为162-2000的聚四氢呋喃,聚己内酯或基于二醇和二羧酸的聚酯醇。优选的二官能醇(B2)是基于氧化乙烯、氧化丙烯、氧化丁烯、氧化戊烯或其混合物的二官能聚醚多元醇以及基于二醇和二羧酸的聚酯醇。
二醇用于微调聚碳酸酯的性能。若使用二官能醇,则二官能醇(B2)与至少三官能醇(B1)的比例由本领域熟练技术人员根据聚碳酸酯的所需性能确定。醇(B2)的量基于所有醇(B1)和(B2)一起的总量通常为0-50mol%。该量优选为0-35mol%,更优选0-25mol%,最优选0-10mol%。
光气、双光气或三光气与醇或醇混合物的反应通常在消除氯化氢下进行;由碳酸酯与醇或醇混合物得到高官能度超支化聚碳酸酯的反应在从碳酸酯分子消除单官能醇或酚下进行。
在该反应之后,即没有任何进一步改性,该超支化聚碳酸酯具有高官能度的羟基和碳酸酯基团或氨基甲酰氯基团封端。高官能度聚碳酸酯就本发明而言应理解为指除了形成聚合物骨架的碳酸酯基团外额外在端或侧位具有至少3个,优选至少4个,更优选至少6个官能基团的产物。官能基团为碳酸酯基团或氨基甲酰氯基团和/或OH基团。端或侧官能基团数目原则上没有上限,但具有非常高数目的官能基团的产物可能具有不希望的性能,例如高粘度或不良溶解性。本发明的高官能度聚碳酸酯通常具有不超过500个端或侧官能基团,优选不超过100个端或侧官能基团。
在高官能度聚碳酸酯的制备中,必须调节包含OH基团的化合物与光气或碳酸酯(A)的比例以使所得最简单缩合产物(下文已知为缩合产物(K))平均包含i)一个碳酸酯或氨基甲酰氯基团和不止一个OH基团或ii)一个OH基团和不止一个碳酸酯或氨基甲酰氯基团,优选平均包含i)一个碳酸酯或氨基甲酰氯基团和至少两个OH基团或ii)一个OH基团和至少两个碳酸酯或氨基甲酰氯基团。
为了微调聚碳酸酯的性能,额外可能合适的是使用至少一种二官能羰基反应性化合物(A1)。这应理解为指具有两个碳酸酯基团和/或羧基的那些化合物。羧基可以是羧酸、碳酰氯、羧酸酐或羧酸酯,优选羧酸酐或羧酸酯,更优选羧酸酯。若使用该类二官能化合物(A1),则(A1)与碳酸酯或光气(A)的比例由本领域熟练技术人员根据聚碳酸酯的所需性能确定。二官能化合物(A1)的量基于所有碳酸酯/光气(A)和化合物(A1)一起的总量通常为0-40mol%。优选该量为0-35mol%,更优选0-25mol%,非常优选0-10mol%。化合物(A1)的实例是二醇的二碳酸酯或二氨基甲酰氯,二醇的实例是乙二醇,1,2-丙二醇,1,3-丙二醇,1,1-二甲基-1,2-乙二醇,2-丁基-2-乙基-1,3-丙二醇,2-乙基-1,3-丙二醇,2-甲基-1,3-丙二醇,新戊二醇,新戊二醇羟基新戊酸酯,1,2-、1,3-或1,4-丁二醇,1,6-己二醇,1,10-癸二醇,异亚丙基二(4-羟基环己烷),四甲基环丁二醇,1,2-、1,3-或1,4-环己二醇,环辛二醇,降冰片烷二醇,蒎烷二醇,萘烷二醇,2-乙基-1,3-己二醇,2,4-二乙基辛烷-1,3-二醇,氢醌,双酚A,双酚F,双酚B,双酚S,2,2-二(4-羟基环己基)丙烷,1,1-、1,2-、1,3-和1,4-环己烷二甲醇以及1,2-、1,3-或1,4-环己二醇。这些化合物例如可以通过使所述二醇与过量的例如上述碳酸酯RO(CO)OR或氯代碳酸酯反应而制备,从而使如此得到的二碳酸酯在两侧被基团RO(CO)-取代。另一可能性是使二醇首先与光气反应得到二醇的相应氯代碳酸酯,然后使这些酯与醇反应。
其他化合物(A1)为二羧酸,二羧酸的酯,优选甲基、乙基、异丙基、正丙基、正丁基、异丁基、仲丁基或叔丁基酯,更优选甲基、乙基或正丁基酯。这类二羧酸的实例是草酸、马来酸、富马酸、琥珀酸、戊二酸、己二酸、癸二酸、十二烷二酸、邻苯二甲酸、间苯二甲酸、对苯二甲酸、壬二酸、1,4-环己烷二甲酸或四氢邻苯二甲酸、辛二酸、邻苯二甲酸酐、四氢邻苯二甲酸酐、六氢邻苯二甲酸酐、四氯邻苯二甲酸酐、桥亚甲基四氢邻苯二甲酸酐、戊二酸酐、二聚脂肪酸、其异构体及其氢化产物。
例如使用碳酸酯(A)与二醇或多元醇(B)的反应作为实例说明的缩合产物(K)的最简单结构产生排列XYm或YmX,其中X为碳酸酯基团或氨基甲酰基,Y为羟基且m通常为大于1至6,优选大于1至4,更优选大于1至3的整数。作为单一基团得到的反应性基团在下文通常称为“焦点基团(focal group)”。
例如当在由碳酸酯和二元醇制备最简单的缩合产物(K)中反应摩尔比为1:1时,如通式(I)所示,平均结果是XY类型的分子。
在以1:1的反应摩尔比由碳酸酯和三元醇制备缩合产物(K)的情况下,如通式(II)所示,平均结果是XY2类型的分子。此时焦点基团为碳酸酯基团。
在由碳酸酯和四元醇再次以1:1的反应摩尔比制备缩合产物(K)中,如通式(III)所示,平均结果是XY3类型的分子。此时焦点基团为碳酸酯基团。
在式(I)-(III)中,R如在开头所定义且R1为脂族或芳族基团。
缩合产物(K)例如还可以如通式(IV)所示由碳酸酯和三元醇制备,其中基于摩尔的反应比为2:1。此时平均结果是X2Y类型的分子,此时焦点基团为OH基团。在式(IV)中,R和R1的定义与上面在式(I)-(III)中的相同。
当额外将二官能化合物如二碳酸酯或二醇加入各组分中时,这产生链增长,例如如通式(V)所示。平均结果再次为XY2类型的分子,其中焦点基团为碳酸酯基团。
在式(V)中,R2为脂族或芳族基团,而R和R1如上所述定义。
还可以将两种或更多种缩合产物(K)用于该合成。此时一方面可以使用两种或更多种醇和/或两种或更多种碳酸酯。此外,通过选择所用醇与碳酸酯或光气的比例,可以获得具有不同结构的不同缩合产物的混合物。这可以通过将碳酸酯与三元醇的反应作为实例举例说明。若起始产物如(II)所示以1:1的比例使用,则得到分子XY2。若如(IV)中所示以2:1的比例使用起始产物,则结果得到分子X2Y。比例为1:1-2:1时得到分子XY2和X2Y的混合物。
(A)与(B)反应形成缩合产物(K)的典型反应条件如下所述:
通常选择组分(A)和(B)的化学计量比以使所得缩合产物(K)含有一个碳酸酯或氨基甲酰氯基团和不止一个OH基团或一个OH基团和不止一个碳酸酯或氨基甲酰氯基团。这在第一种情况下通过1mol碳酸酯基团:>2mol OH基团的化学计量比,例如1:2.1-8,优选1:2.2-6,更优选1:2.5-4,非常优选1:2.8-3.5的化学计量比实现。在第二种情况下,这通过大于1mol碳酸酯基团:<1mol OH基团的化学计量比,例如1:0.1-0.48,优选1:0.15-0.45,更优选1:0.25-0.4,非常优选1:0.28-0.35的化学计量比实现。
温度应对该醇与对应羰基组分的反应足够。对于与光气的反应,足够的温度通常为-20°C至120°C,优选0-100°C,更优选20-80°C。当使用碳酸酯时,温度应为60-280°C,优选80-250°C,更优选100-250°C,非常优选120-250°C。
制备通常在0.1毫巴至20巴,优选1毫巴至5巴的压力范围内在分批、半分批或连续操作的反应器或反应器级联中进行。
所用溶剂包括芳族和/或(环)脂族烃及其混合物、卤代烃、酮类、酯类和醚类,优选乙酸丁酯、二甲基甲酰胺、二甲基乙酰胺、二甲亚砜、乙酸甲氧基丙酯、异丁基甲基酮、2-丁酮、芳族烃类(如产品)、环己烷、氯苯和二甲苯。优选实施方案是在无溶剂下进行该反应。
各组分加入的顺序通常不太重要。通常而言,合理的是首先引入这两种反应配对的过量组分,并加入缺乏组分。或者同样可以在反应开始之前将这两种组分相互混合,然后将该混合物加热至所需反应温度。
在式(I)-(V)中示例描述的简单缩合产物(K)按照本发明优选立即发生分子间的进一步反应,形成高官能度缩聚产物,这在下文称为缩聚产物(P)。得到缩合产物(K)以及得到缩聚产物(P)的反应通常在0-300°C,优选0-250°C,更优选60-250°C,非常优选80-250°C的温度下在本体中(无溶剂)或在溶液中进行。就此而言通常可以使用任何对相应反应物呈惰性的溶剂。优选使用有机溶剂,如上面所述那些,例如更优选癸烷、十二烷、环己烷、苯、甲苯、氯苯、二甲苯、二甲基甲酰胺、二甲基乙酰胺、二甲亚砜或溶剂石脑油。在一个优选实施方案中,缩合反应在本体中进行。在反应过程中释放的单官能醇或酚ROH可以从反应平衡中除去以加速该反应,该除去例如通过蒸馏手段进行,任选在减压下蒸馏。
该醇或酚的分离也可以通过使在反应条件下基本呈惰性的气体料流如氮气、蒸汽、二氧化碳料流通过反应混合物(即汽提)或者例如使含氧气体如大气空气或贫空气通过该混合物而进行。若想要蒸馏除去,则通常合适的是使用在反应过程中释放出在盛行的压力下沸点小于140°C的醇或酚ROH的碳酸酯。或者释放的醇可以通过使用共沸物形成剂(例如甲苯、二甲苯、氯苯、环己烷)的共沸蒸馏或者通过施加真空而除去,该除去支持缩聚物的形成。
为了加速该反应,还可以加入催化剂或催化剂混合物。合适的催化剂是催化酯化或酯交换反应的化合物,实例是碱金属氢氧化物、碱金属碳酸盐、碱金属碳酸氢盐,优选钠、钾或铯的氢氧化物、碳酸盐、碳酸氢盐,叔胺,胍类,铵化合物,化合物,有机铝,有机锡,有机锌,有机钛、有机锆或有机铋化合物,以及还有已知为双金属氰化物(DMC)催化剂的那类催化剂,例如如DE 10138216或DE 10147712所述。优选使用氢氧化钾、碳酸钾、碳酸氢钾、二氮杂双环辛烷(DABCO)、二氮杂双环壬烯(DBN)、二氮杂双环十一碳烯(DBU),咪唑类如咪唑、1-甲基咪唑或1,2-二甲基咪唑,四丁醇钛,四异丙醇钛,氧化二丁基锡,二月桂酸二丁基锡,二辛酸锡,乙酰丙酮锆或其混合物。基于所用醇或醇混合物的量,该催化剂的加入量通常为50-10000重量ppm,优选100-5000重量ppm。可能任选需要将该催化剂预溶于少量合适溶剂中。
此外,还可以通过加入合适的催化剂和/或通过选择合适的温度而控制分子间缩聚反应。此外,聚合物(P)的平均分子量可以经由起始组分的组成以及经由停留时间而调节。
已经在升高的温度下制备的缩合产物(K)和缩聚产物(P)在室温下在较长时间内通常是稳定的,例如至少稳定6周,而不显示出浑浊、沉淀和/或任何粘度增加。考虑到缩合产物(K)的性质,可能的是缩合反应可能得到具有不同结构的缩聚产物(P),其具有支链但没有交联。此外,在理想情况下缩聚产物(P)含有一个碳酸酯或氨基甲酰氯焦点基团和不止两个OH基团,或者一个OH焦点基团和不止两个碳酸酯或氨基甲酰氯基团。反应性基团的数量取决于所用缩合产物(K)的性质和缩聚程度。
例如,通式(II)的缩合产物(K)可以通过三重分子间缩合反应形成两种不同的缩聚产物(P),其以通式(VI)和(VII)表示。
在式(VI)和(VII)中的R和R1如上所定义。
为了终止分子间缩聚反应,存在多种可能性。例如可以将温度降至其中该反应停止且产物(K)或缩聚产物(P)储存稳定的范围。这通常在低于60°C,优选低于50°C,更优选低于40°C,非常优选室温下实现。此外,可以钝化该催化剂:例如在碱性催化剂的情况下通过加入酸性组分,例如路易斯酸,或有机或无机质子酸。另一可能性是通过用预冷溶剂稀释而抑制该反应。这在必须通过加入溶剂调节反应混合物的粘度时是特别优选的。
在另一实施方案中,一旦缩合产物(K)的分子间反应得到具有所需缩聚程度的缩聚产物(P),则可以通过向产物(P)中加入具有对(P)的焦点基团呈反应性的基团的产物而抑制该反应。例如,在碳酸酯或氨基甲酰基焦点基团的情况下,例如可以加入单-、二-或多胺。在羟基焦点基团的情况下,产物(P)中例如可能已经加有单-、二-或多异氰酸酯,包含环氧化物基团的化合物或对OH基团呈反应性的酸衍生物。
作为如上所述设定反应条件的结果以及任选作为选择合适溶剂的结果,本发明产物可以在制备之后进一步加工,而不额外提纯。需要的话,可以将反应混合物脱色,例如通过用活性炭或金属氧化物如氧化铝、二氧化硅、氧化镁、氧化锆、氧化硼或其混合物以例如0.1-50重量%,优选0.5-25重量%,更优选1-10重量%的量在例如10-100°C,优选20-80°C,更优选30-60°C的温度下处理。还任选可以过滤反应混合物以除去任何存在的沉淀物。在另一优选实施方案中,将产物汽提,即除去低分子量的挥发性化合物。为此,在达到所需转化度之后,可以任选使催化剂钝化并可以通过蒸馏除去低分子量的挥发性成分,如一元醇、酚类、碳酸酯、氯化氢或挥发性低聚或环状化合物,任选伴随引入气体,优选氮气、二氧化碳或空气,任选在减压下蒸馏。
可以如上所述得到的超支化聚碳酸酯通常具有小于50°C,优选小于30°C,更优选小于10°C的玻璃化转变温度。OH值通常为至少30mgKOH/g,优选50-250mg/g。重均分子量Mw通常为1000-150000g/mol,优选1500-100000g/mol,数均分子量Mn为500-50000g/mol,优选1000-40000g/mol。该超支化聚碳酸酯通常在水中呈不溶性或不可分散性,即不能制备透明(即没有裸眼可见颗粒)水溶液或水分散体。
该两亲分子优选包含烷氧基化超支化聚碳酸酯。术语“烷氧基化”是指超支化聚碳酸酯已经与氧化烯反应。结果该聚碳酸酯包含至少一个线性聚氧化烯基团。可以存在单体的无规混合物或嵌段,优选嵌段。该烷氧基化聚碳酸酯优选仅用氧化乙烯烷氧基化或用氧化乙烯和C3-C5氧化烯的混合物烷氧基化。更优选仅用氧化乙烯烷氧基化。合适的C3-C5氧化烯是氧化丙烯、氧化丁烯或氧化戊烯及其混合物。优选的C3-C5氧化烯是氧化丙烯。氧化乙烯和C3-C5氧化烯的混合物优选包含至少40mol%,更优选至少60mol%,尤其是至少80mol%氧化乙烯,在每种情况下基于该混合物中氧化乙烯和C3-C5氧化烯的总摩尔数。该烷氧基化聚碳酸酯更优选用氧化乙烯和C3-C5氧化烯的混合物烷氧基化,得到氧化乙烯嵌段和C3-C5氧化烯嵌段。
在另一优选实施方案中,该聚碳酸酯包含至少一个通过烷氧基化制备的聚氧化烯基团。该聚氧化烯基团更优选包含至少一个聚氧化乙烯嵌段和至少一个聚(C3-C5氧化烯)嵌段,后者优选为聚氧化丙烯。该聚(C3-C5氧化烯)嵌段尤其优选直接键于该超支化聚碳酸酯。该聚氧化乙烯嵌段尤其优选不直接键于该聚碳酸酯,而是仅键于该聚(C3-C5氧化烯)。适合该聚(C3-C5氧化烯)的C3-C5氧化烯如上所述。嵌段结构可以通过首先用C3-C5氧化烯烷氧基化该超支化聚碳酸酯并随后用氧化乙烯烷氧基化如此得到的反应产物而得到。
C3-C12氧化烯(来自该至少三官能或高级多官能聚醚醇)和C3-C5氧化烯(来自该超支化聚碳酸酯的烷氧基化)的总和与氧化乙烯的重量比通常为3:1-1:3,优选2.5:1-1:2.5,尤其是2:1-1:2。该聚碳酸酯的烷氧基化可以通过用于制备该两亲分子的本发明方法进行。
烷氧基化超支化聚碳酸酯优选为水溶性的。这意味着它在20°C下在水中至少以2重量%,优选8重量%,尤其是至少15重量%的程度可溶。
在另一实施方案中,该烷氧基化超支化聚碳酸酯通常为水分散性的。这意味着它在20°C下在水中至少以2重量%,优选8重量%,尤其是至少15重量%的程度可分散。
烷氧基化超支化聚碳酸酯通常具有1-150mg KOH/g聚合物,优选10-120mg KOH/g,尤其是20-100mg KOH/g的OH值。
本发明组合物通常包含0.01-40重量%,优选0.05-30重量%,更优选0.1-20重量%的两亲分子。
本发明组合物可以通过使该两亲分子和在20°C下在水中的溶解度不超过10g/L的活性成分接触而得到。各组分可以通过为公知常识的方法如混合、乳化或悬浮而接触。
活性成分与两亲分子的重量比通常为100:1-1:100,优选10:1-1:50,更优选2:1-1:25。该活性成分可以呈溶解形式或者呈固体颗粒状形式。活性成分颗粒可以是结晶或者无定形的。粒度可以为1nm至10μm。该组合物可以是活性成分的溶液、乳液、悬浮液或悬浮乳液。本发明组合物优选为含水组合物。优选它包含至少40重量%,更优选至少60重量%,更具体至少80重量%的水。该组合物通常包含不超过99重量%的水。
本发明组合物可以包含配制助剂,助剂的选择通常由特定施用形式和/或活性成分决定。合适的配制助剂实例是溶剂、固体载体、表面活性物质(如表面活性剂、保护性胶体、润湿剂和粘着剂)、有机和无机增稠剂、杀菌剂、防冻剂、消泡剂、任选还有着色剂和粘合剂(例如用于种子处理)。
所用表面活性物质(辅助剂、润湿剂、粘着剂、分散剂或乳化剂)包括芳族磺酸的碱金属、碱土金属和铵盐,例如木素磺酸(产品,挪威Borregaard)、苯酚磺酸、萘磺酸(产品,Akzo Nobel,USA)和二丁基萘磺酸(产品,德国BASF)的那些,以及还有脂肪酸、烷基-和烷基芳基磺酸、烷基月桂基醚和脂肪醇硫酸的那些,还有硫酸化十六、十七和十八烷醇的盐以及脂肪醇二醇醚的盐,磺化萘及其衍生物与甲醛的缩合产物,萘或萘磺酸与苯酚和甲醛的缩合产物,聚氧乙烯辛基酚醚,乙氧基化异辛基酚、辛基酚或壬基酚,烷基苯基和三丁基苯基聚乙二醇醚,烷基芳基聚醚醇,异十三烷醇,脂肪醇氧化乙烯缩合物,乙氧基化蓖麻油,聚氧乙烯或聚氧丙烯烷基醚,月桂醇聚乙二醇醚乙酸酯,山梨醇酯,木素亚硫酸盐废液,还有蛋白质,变性蛋白,多糖(例如甲基纤维素),疏水改性淀粉,聚乙烯醇(产品,瑞士Clariant),聚羧酸酯(产品,德国BASF),聚烷氧基化物,聚乙烯基胺(产品,德国BASF),聚乙烯亚胺(产品,德国BASF),聚乙烯基吡咯烷酮及其共聚物。
合适的表面活性剂尤其包括阴离子、阳离子、非离子和两性表面活性剂,嵌段聚合物和聚电解质。合适的阴离子表面活性剂是磺酸、硫酸、磷酸或羧酸的碱金属、碱土金属或铵盐。磺酸盐的实例是烷基芳基磺酸盐、二苯基磺酸盐、α-烯烃磺酸盐、脂肪酸和油的磺酸盐、乙氧基化烷基酚的磺酸盐、缩合萘的磺酸盐、十二烷基和十三烷基苯的磺酸盐、萘和烷基萘的磺酸盐、磺基琥珀酸盐或磺基琥珀酰胺酸盐。硫酸盐的实例是脂肪酸和油、乙氧基化烷基酚、醇、乙氧基化醇或脂肪酸酯的硫酸盐。磷酸化物的实例是磷酸酯。羧酸酯的实例是烷基羧酸盐和羧化醇或烷基酚乙氧基化物。
合适的非离子表面活性剂是烷氧基化物,N-烷基化脂肪酸酰胺,胺氧化物,酯或糖基表面活性剂。烷氧基化物的实例是已经烷氧基化的化合物,如醇、烷基酚、胺、酰胺、芳基酚、脂肪酸或脂肪酸酯。对于烷氧基化,可以使用氧化乙烯和/或氧化丙烯,优选氧化乙烯。N-烷基化脂肪酸酰胺的实例是脂肪酸葡糖酰胺或脂肪酸链烷醇酰胺。酯的实例是脂肪酸酯、甘油酯或甘油单酯。糖基表面活性剂的实例是脱水山梨糖醇、乙氧基化脱水山梨糖醇、蔗糖酯和葡萄糖酯,或烷基聚葡糖苷。合适的阳离子表面活性剂是季铵型表面活性剂,实例是具有1或2个疏水性基团的季铵化合物,或长链伯胺的盐。合适的两性表面活性剂是烷基甜菜碱和咪唑啉类。合适的嵌段聚合物是包含聚氧化乙烯和聚氧化丙烯的嵌段的A-B或A-B-A型嵌段聚合物,或包含链烷醇、聚氧化乙烯和聚氧化丙烯的A-B-C型嵌段聚合物。合适的聚电解质是多酸或多碱。多酸的实例是聚丙烯酸的碱金属盐。多碱的实例是聚乙烯基胺或聚乙烯胺。
本发明组合物可以包含大量表面活性物质和表面活性剂。它基于该组合物的总量可以包含0.1-40%,优选1-30%,更具体为2-20重量%的表面活性物质和表面活性剂的总量。
辅助剂的实例是有机改性的聚硅氧烷,例如BreakThruS醇烷氧基化物,例如245、MBA 1303、LF和ON;EO/PO嵌段聚合物,例如RPE 2035和B;醇乙氧基化物,例如XP 80;以及磺基琥珀酸二辛酯钠,例如RA。
增稠剂(即赋予组合物以改性的流动性能,即静止状态下的高粘度和运动状态下的低粘度的化合物)的实例是多糖以及有机和无机层状矿物如黄原胶(CP Kelco),23(Rhodia)或(R.T.Vanderbilt)或(Engelhard Corp.)。
在一个实施方案中,活性化合物为农药且本发明组合物呈农业化学配制剂形式。合适的农业化学配制剂是水溶性浓缩物(SL、LS),可再分散浓缩物(DC),可乳化浓缩物(EC),乳液(EW、EO、ES、ME)、悬浮液(SC、OD、FS)或悬浮乳液(SE)。该组合物优选呈可乳化浓缩物(EC)、悬浮浓缩物(SC)、水溶性浓缩物(SL)、种子处理用溶液(LS)或可再分散浓缩物(DC)形式。
通常在施用前稀释农业化学配制剂,以制备已知的桶混物。适合稀释的试剂包括中至高沸点的矿物油馏分,如煤油或柴油,还有煤焦油以及植物或动物来源的油,脂族、环状和芳族烃类,例如甲苯、二甲苯、石蜡、四氢化萘、烷基化萘或其衍生物,甲醇,乙醇,丙醇,丁醇,环己醇,环己酮,异佛尔酮,强极性溶剂,例如二甲亚砜、N-甲基吡咯烷酮或水。优选使用水。还可以仅将该两亲分子加入实际桶混物中。在该实施方案中,本发明组合物呈桶混物形式。
稀释的组合物通常通过喷雾或雾化施用。可以在紧临施用之前向桶混物中加入各种类型的油、润湿剂、辅助剂、除草剂、杀菌剂或杀真菌剂(桶混)。这些试剂可以以1:100-100:1,优选1:10-10:1的重量比混入本发明组合物中。农药在桶混物中的浓度可以在较宽范围内变化。浓度通常为0.0001-10%,优选0.01-1%。在作物保护中施用的情况下,施用率取决于所需效果的性质为0.01-2.0kg活性成分/ha。
农业化学配制剂可以用于防治植物病原性真菌和/或不希望的植物生长和/或不希望的昆虫或螨虫侵染和/或调节植物生长,此时使该组合物作用于相应害虫、其栖息地或要防止相应害虫的植物、土壤和/或不希望的植物和/或农作物和/或其生长场所。农业化学配制剂还可以用于在植物上防治不希望的昆虫或螨虫侵染和/或防治植物病原性真菌和/或防止不希望的植物生长,其中用该组合物处理农作物的种子。
本发明还提供了一种包含烷氧基化超支化聚碳酸酯的两亲分子,其中该聚碳酸酯包含醇(B1),所述醇(B1)为基于C3-C12氧化烯和具有至少三个OH基团的醇的三官能或高级多官能聚醚醇。该两亲分子可以由并且优选由如下所述的本发明制备方法得到。该聚醚醇优选以聚合形式包含至少三个C3-C12氧化烯分子。烷氧基化聚碳酸酯优选用氧化乙烯或氧化乙烯与C3-C5氧化烯的混合物烷氧基化。其他合适且优选的实施方案已经如上所述。
本发明还涉及一种通过将超支化聚碳酸酯烷氧基化而制备本发明两亲分子的方法,其中该聚碳酸酯包含醇(B1),所述醇(B1)为基于C3-C12氧化烯和具有至少三个OH基团的醇的三官能或高级多官能聚醚醇。聚碳酸酯优选使用氧化乙烯或氧化乙烯与C3-C5氧化烯的混合物烷氧基化。C3-C12氧化烯和C3-C5氧化烯的总和与氧化乙烯的重量比通常为3:1-1:3。聚碳酸酯更优选首先用C3-C5氧化烯烷氧基化,然后用氧化乙烯烷氧基化。
烷氧基化可以通过常规反应方法进行,例如在高压釜中进行。烷氧基化可以通过强碱如碱金属氢氧化物和碱土金属氢氧化物,布朗斯台德酸或路易斯酸如AlCl3、BF3等催化。对于窄分布的烷氧基化物,可以使用催化剂如水滑石或DMC。烷氧基化优选在约80-250°C,优选约100-220°C的温度下进行。压力优选介于环境压力和600巴之间。需要的话,氧化烯可以包含加入的惰性气体,例如约5-60%。烷氧基化的粗产物可以在没有进一步后处理下用于本发明组合物中。可以任选将它过滤,例如以除去催化剂残余物。
本发明额外提供本发明两亲分子在水溶液中加溶在20°C下在水中的溶解度不超过10g/L的活性成分的用途。
本发明进一步涉及一种防治植物病原性真菌和/或不希望的植物生长和/或不希望的昆虫或螨虫侵染和/或调节植物生长的方法,其中使本发明组合物作用于相应害虫、其栖息地或要防止相应害虫的植物、土壤和/或不希望的植物和/或农作物和/或其生长场所。本发明还涉及本发明组合物防治植物病原性真菌和/或不希望的植物生长和/或不希望的昆虫或螨虫侵染和/或调节植物生长中的用途。
本发明的优点是可以将高浓度的活性成分制成溶液;可以非常容易地工业实现该两亲分子由工业上易得单体的制备,任选甚至以单釜方法。另一优点是该两亲分子本身为水溶性的或水分散性的并且与许多聚酯相比对水解不太敏感。其他优点是活性成分的生物利用率增加,农业化学活性成分的内吸效果在叶面吸收时提高,甚至微溶性农业化学活性成分现在可以配制在溶液中,例如作为SL(水溶性浓缩物)或LS(种子处理用溶液),农业化学活性成分在喷雾溶液中的分布得到改善以及可以更有效地用水清洁活性成分的多次使用的包装和施用设备(例如农药用喷雾设备)。
下列实施例说明但不限制本发明。
实施例
未改性超支化聚碳酸酯和烷氧基化聚碳酸酯二者通过使用折射计作为检测器的凝胶渗透色谱法分析。所用移动相为二甲基乙酰胺,而用于测定分子量的标样为聚甲基丙烯酸甲酯(PMMA)。OH值按照DIN 53240第2部分测定。
实施例1A:合成具有羟基端基的超支化聚碳酸酯核
首先加入2000g TMP×15.7PO(三羟甲基丙烷与15.7摩尔过量的氧化丙烯的反应产物)、247g碳酸二乙酯和1.7g二月桂酸二正丁基锡催化剂。将反应混合物加热至165°C并在搅拌下保持沸腾13小时,直到反应混合物的温度因释放的乙醇蒸发性冷却而降至143°C的恒定温度。然后将回流冷凝器用具有收集容器的下行冷凝器(descending condenser)替代,并蒸除在该反应中形成的乙醇,在此期间反应混合物的温度升至230°C。将乙醇收集在冷却的圆底烧瓶中并称重,由此以与理论上可能的完全转化率相比的百分数确定转化率。在达到89%的转化率之后,使干氮气在160°C的温度下通过反应混合物3小时以除去仍存在的残留量单体。然后将该混合物冷却至室温。以水不溶性的高粘度黄色液体形式得到聚合物(Mn=3000g/mol;Mw=6200g/mol;OH值:87mg KOH/g聚合物)。
实施例1B:合成具有羟基端基的超支化聚碳酸酯核
首先加入4010g TMP×15.7PO(三羟甲基丙烷与15.7摩尔过量的氧化丙烯的反应产物)和502g碳酸二乙酯并与2g氢氧化钾在10g乙醇中的新制溶液混合。将反应混合物加热至155°C并在搅拌下保持沸腾3.5小时,直到反应混合物的温度因释放的乙醇蒸发性冷却而降至130°C的恒定温度。然后将回流冷凝器用具有收集容器的下行冷凝器替代,并蒸除在该反应中形成的乙醇,在此期间温度升至200°C。将乙醇收集在冷却的圆底烧瓶中并称重,由此以与理论上可能的完全转化率相比的百分数确定转化率。在达到80%的转化率之后,将该反应冷却至100°C并与4g作为终止剂的80%磷酸混合。然后在搅拌下将该混合物加热至135°C并使干氮气在该温度下通过反应混合物5小时以除去仍存在的残留量单体。然后将该混合物冷却至室温。以水不溶性的高粘度黄色液体形式得到聚合物(Mn=2450g/mol;Mw=5330g/mol;OH值:92mg KOH/g聚合物)。
实施例1C:来自实施例1A的超支化聚碳酸酯核的乙氧基化
首先将100g来自实施例1A的聚合物加入高压釜中并与1.35g 50%KOH水溶液混合。一旦用氮气惰性化反应混合物,就在120°C和减压下从该混合物中除去水残余物。然后在120°C下以0.5ml/min的计量速率将100g氧化乙烯加入反应混合物中。在氧化乙烯的计量加料结束并且达到恒定的反应器压力之后,在减压下蒸除未转化的氧化乙烯和其他挥发性成分并将乙氧基化聚合物从聚合反应器中取出。然后将粗产物在分开的反应设备中与5%(PQ Corp.;用于除去碱残余物的硅酸镁)和2%水混合,加热至80°C并保持1小时,然后再次在减压下将加入的水从反应混合物中蒸除。过滤粗产物而以完全水溶性的高粘度浅黄色液体形式得到190g乙氧基化聚合物(Mn=4860g/mol;Mw=12980g/mol;OH值:47mg KOH/g聚合物)。
实施例2:
加溶活性成分
将100mg聚合物称入50mL玻璃烧杯中并溶于9.900g蒸馏水中。然后将100mg各活性成分称入该批料中得到过饱和溶液。然后使用鼓式混合机将该混合物在室温下搅拌24小时。在静置1小时之后,通过离心除去未加溶的活性成分。然后借助UV光谱法分析所得透明溶液的活性成分含量。在下列波长下分析活性成分:芘334nm,唑菌胺酯277nm,锐劲特280nm。
表1:
a)非本发明;b)100mg聚合物不溶于9.9g水中。
Claims (15)
1.一种包含在20°C下在水中的溶解度不超过10g/L的活性成分和包含烷氧基化超支化聚碳酸酯的两亲分子的组合物,其中所述聚碳酸酯包含醇(B1),所述醇(B1)为基于C3-C12氧化烯和具有至少三个OH基团的醇的三官能或高级多官能聚醚醇。
2.根据权利要求1的组合物,其中所述聚醚醇以聚合形式包含至少三个C3-C12氧化烯分子。
3.根据权利要求1或2的组合物,其中所述C3-C12氧化烯为氧化丙烯。
4.根据权利要求1-3中任一项的组合物,其中所述具有至少三个OH基团的醇为甘油、三羟甲基乙烷、三羟甲基丙烷、1,2,4-丁三醇、1,2,3-己三醇、1,2,4-己三醇或季戊四醇。
5.根据权利要求1-4中任一项的组合物,其中所述烷氧基化聚碳酸酯用氧化乙烯或氧化乙烯与C3-C5氧化烯的混合物烷氧基化。
6.根据权利要求5的组合物,其中C3-C12氧化烯和C3-C5氧化烯的总和与氧化乙烯的重量比为3:1-1:3。
7.根据权利要求1-6中任一项的组合物,其中所述活性成分为农业化学活性成分。
8.一种包含烷氧基化超支化聚碳酸酯的两亲分子,其中所述聚碳酸酯包含醇(B1),所述醇(B1)为基于C3-C12氧化烯和具有至少三个OH基团的醇的三官能或高级多官能聚醚醇。
9.根据权利要求8的两亲分子,其中所述聚醚醇以聚合形式包含至少三个C3-C12氧化烯分子。
10.根据权利要求8或9的两亲分子,其中所述烷氧基化聚碳酸酯用氧化乙烯或氧化乙烯与C3-C5氧化烯的混合物烷氧基化。
11.一种通过将超支化聚碳酸酯烷氧基化而制备根据权利要求8-10中任一项的两亲分子的方法,其中所述聚碳酸酯包含醇(B1),所述醇(B1)为基于C3-C12氧化烯和具有至少三个OH基团的醇的三官能或高级多官能聚醚醇。
12.根据权利要求11的方法,其中使用氧化乙烯或氧化乙烯与C3-C5氧化烯的混合物烷氧基化所述聚碳酸酯。
13.根据权利要求12的方法,其中C3-C12氧化烯和C3-C5氧化烯的总和与氧化乙烯的重量比为3:1-1:3。
14.根据权利要求8-10中任一项的两亲分子在水溶液中加溶在20°C下在水中的溶解度不超过10g/L的活性成分的用途。
15.一种防治植物病原性真菌和/或不希望的植物生长和/或不希望的昆虫或螨虫侵染和/或调节植物生长的方法,其中使根据权利要求1-7中任一项的组合物作用于相应害虫、其栖息地或要防止相应害虫的植物、土壤和/或不希望的植物和/或农作物和/或其生长场所。
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CN109561679A (zh) * | 2016-07-29 | 2019-04-02 | 巴斯夫欧洲公司 | 其中将烷氧基化甘油施用于土壤而控制昆虫的方法 |
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KR101388683B1 (ko) | 2012-04-30 | 2014-04-24 | 한국교통대학교산학협력단 | 제거가 용이한 화합물을 이용한 가용성 그라핀 용액의 제조방법 |
WO2016102203A1 (en) | 2014-12-23 | 2016-06-30 | Basf Se | Hyperbranched polymer modified with isocyanate linker and mix of short and long chain alkyl polyether |
CN107151316B (zh) * | 2017-06-20 | 2019-04-19 | 西北工业大学 | 能发射明亮荧光的羰基封端的超支化聚碳酸酯及制备方法 |
BR112022020134A2 (pt) | 2020-04-06 | 2022-11-22 | Basf Corp | Composição agroquímica aquosa, métodos para produzir a composição agroquímica, para controlar vegetação indesejada e para reduzir a deriva de pulverização e composição adjuvante |
CN115299445B (zh) * | 2022-10-08 | 2023-02-03 | 云南省烟草公司昆明市公司 | 提升香菇多糖对植物诱导抗病性的复合溶液和配制方法、方法及植物田间防治病毒方法 |
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