CN101959403A - 阻止跨水-油界面相互作用的稳定乳液制剂 - Google Patents
阻止跨水-油界面相互作用的稳定乳液制剂 Download PDFInfo
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- CN101959403A CN101959403A CN2008801043007A CN200880104300A CN101959403A CN 101959403 A CN101959403 A CN 101959403A CN 2008801043007 A CN2008801043007 A CN 2008801043007A CN 200880104300 A CN200880104300 A CN 200880104300A CN 101959403 A CN101959403 A CN 101959403A
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- A01N25/10—Macromolecular compounds
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Abstract
水包油乳液的内部油相各成分和连续水相各成分之间的相互作用会通过加入聚合物表面活性剂混合物而被阻止,这减少了化学和/或物理不稳定性,并改善了制剂中各成分的相容性。
Description
本申请要求于2007年8月30日递交的美国临时申请60/966,793的优先权。
技术领域
本发明涉及新型稳定乳液组合物,其阻止油相各成分和水相各成分之间跨油-水界面(across the oil-water interface)的相互作用。
背景技术
为了设计农用制剂产品,要解决的最重要的问题是其稳定性。如果不能满足一组稳定性要求(稳定性要求通常取决于具体的市场、应用和规则),那么必然会导致其商业化的失败。制剂不稳定性有许多成因,例如a)由于各成分(活性物质和/或惰性物质等)之间的反应、光降解作用和氧化作用等导致的化学不稳定性,b)由相分离(奥斯瓦尔德熟化(Oswald ripening)、结晶、沉降、乳状液分层(creaming)等)导致的物理不稳定性,以及c)环境因素(温度、湿度/湿气等)。在如今的农用化学品市场中,越来越普遍的是设计含有多种活性成分以及它们所需的溶剂、安全剂(safener)和/或辅料等的制剂以实现最佳的控制谱(spectrum)、功效和递送效率,结果这些导致制剂的稳定性越来越具有挑战性。因此,能够有效地分离、阻止或消除不相容成分之间的不利反应或相互作用的技术对于成功的产品常常是关键的。
水包油(正相(normal))或油包水(反相/逆相(reverse/inverse))乳液是许多农用产品中最常见的制剂类型的一种,其中通过表面活性剂乳化剂稳定的油滴或水滴作为分散相均匀地分散在作为连续相的水或油介质中。然而,当油成分或油溶性成分可能会水解、或与水相中各成分反应、或在水中具有足够高的溶解性而导致奥斯瓦尔德熟化时,或者相反地,当水溶性或水分散性成分可能会与油成分反应或具有足够高的油溶性而导致油相中发生奥斯瓦尔德熟化时,就会存在许多挑战。例如,已经发现含有三氯吡氧乙酸丁氧乙酯(triclopyr butoxyethyl ester)和氯氨吡啶酸(aminopyralid)钾盐的组合物非常适用于控制牧场(range)和草地(pasture)和工业植被管理应用区的灌木丛和木本植物。然而,在典型的含油溶性酯除草剂和水溶性盐除草剂的乳液制剂中,三氯吡氧乙酸丁氧乙酯易于水解为相应的酸。因为酸形成的原因,乳液由于三氯吡氧乙酸(triclopyr)和氯氨吡啶酸两者的晶体形成而变质。另一个实例是含有五氟磺草胺(penoxsulam)和吡氟草胺(diflufenican)和甲基化的种子油性辅料(methylated seed oil adjuvant)的水性分散体的组合物,发现该组合物非常有用于谷类除草性应用,但是吡氟草胺在油中的溶解性足够导致因奥斯瓦尔德熟化造成的晶体快速生长,这导致了乳液失去稳定性。在该两种实例中,期望的是具有稳定的乳液制剂,提供屏障以阻止或防止内部油相和连续水相之间不期望的相互作用。
发明内容
本发明涉及稳定的水包油乳液,其含有:
a)分散(discrete)油相,包含油性活性成分、油溶性活性成分、油性辅料或油性溶剂,其能与连续水相中的各成分反应或相互作用以引起化学或物理上的不稳定性;
b)连续水相,包含水和水溶性或水分散性成分;
c)量为1g/L至200g/L的第一聚合物表面活性剂和量为1g/L至200g/L的第二聚合物表面活性剂,所述第一聚合物表面活性剂包含具有聚氧化乙烯(PEG)亲水部分和12-羟基硬脂酸疏水部分的ABA嵌段共聚物,所述第二聚合物表面活性剂包含聚亚烷基二醇醚;以及
d)任选地,其他惰性制剂成分。
本发明的另一个方面涉及使用稳定的水包油乳液和任选将其稀释在水性喷雾混合物中用于农业应用的方法,所述农业应用如杂草管理、植物疾病管理或虫害管理。
图1是比较现有技术制剂A和本发明稳定制剂B的三氯吡氧乙酸丁氧乙酯水解的示意图。在54℃加速稳定性测试时,三氯吡氧乙酸在制剂A中的水解显著大于在制剂B中的水解。
本发明提供了通过聚合物表面活性剂稳定的水包油乳液,该聚合物表面活性剂阻止或防止分散油相各成分和连续水相各成分之间的不利的相互作用和反应,这种相互作用和反应会导致组合物的化学或物理不稳定性。
油相含有水混溶性成分,例如溶剂、液体活性物、油溶性活性物、辅料或基本水可混溶的其他所需成分。在典型的水包油乳液中,油相形成了由乳化剂稳定的分散液滴,液滴悬浮在连续水相中。油相中各成分与水相中各成分的相互作用和反应包括但不限于:油相中成分的水解、由于水相中存在的其他成分所导致的油相中成分的降解,或者油相中成分由于其较高的水溶性而在水相中形成晶体和生长(奥斯瓦尔德熟化)。
有可能发生水解的油混溶性、油溶性或油可分散性的农用活性物包括但不限于羧化物的酯(esters of carboxylate)、磷酸酯(phosphate)、或硫酸酯(sulfate)杀虫剂,包括:苯甲酸除草剂,例如二氯甲氧苯酸酯类,苯氧基链烷酸除草剂如2,4-滴(2,4-D)、MCPA或2,4-滴丁酸(2,4-DB)酯类;芳氧苯氧基丙酸除草剂,如炔草酯(clodinafop)、氰氟草酯(cyhalofop)、噁唑禾草灵(fenoxaprop)、吡氟禾草灵(fluazfop)、吡氟氯禾灵(haloxyfop)和喹禾灵酯类(quizalofop esters);和吡啶羧酸类除草剂,如氟草烟(fluroxypyr)和三氯吡氧乙酸酯类;和杀虫剂,如毒死蜱(chlorpyrfos)、甲基毒死蜱(chlorpyrfos-methyl);以及杀真菌剂,如敌螨普(dinocap)、亚胺菌(kresoxim-methyl)等。
具有足够高水溶性(约>60ppm)的、熔点足够高以至在环境条件下为固体以及可能导致水相中因奥斯瓦尔德熟化引起的晶体形成和生长的油混溶性、油溶性或油可分散性的农用活性物,包括但不限于艾克敌105(spinosad)、多杀霉素(spinetoram)、吡虫啉(imidacloprid)、敌稗(propanil)、环唑醇(cyproconazole)、吡虫清(acetamiprid)、氨唑草酮(amicarbazone)、酰氨磺隆(amidosulfuron)、磺草灵(asulam)、噻草平(bentazone)、甲萘威(carbaryl)、清菌脲(cymoxanil)、麦草畏(dicamba)、双氟磺草胺(florasulam)、腈菌唑(myclobutanil)、氯定(nitrapyrin)、毒莠定(picloram)、丙环唑(propiconazole)、氟丙黄隆(prosulfuron)、丙硫菌唑(prothioconazole)、拒嗪酮(pymetrozine)、乙黄磺隆(sulfosulfuron)、三氯吡氧乙酸、三环唑(tricyclazole)、马拉硫磷(malathion)、二氟吡隆(diflufenzopyr),等。
任选地,用于溶剂、稀释剂或辅料目的的油包括但不限于:各石油馏分或烃类,如矿物油、芳香族溶剂、二甲苯、石蜡基油等;植物油,如大豆油、菜籽油、橄榄油、蓖麻油、葵花籽油、椰子油、玉米油、棉籽油、亚麻子油、棕榈油、花生油、红花油、芝麻油、桐油等;上述植物油的酯;一元醇或二元醇、三元醇或其他低级多元醇(含有4-6个羟基)的酯,例如硬脂酸2-乙基己酯、油酸正丁酯、肉豆蔻酸异丙酯、二油酸丙二醇酯、琥珀酸二辛酯、己二酸二丁酯、邻苯二甲酸二辛酯等;一元羧酸、二元羧酸和多元羧酸的酯,等等。
对于在使用时可能要进一步稀释的制剂浓缩物而言,分散油相可为总组合物的1g/L至800g/L,优选为10g/L至500g/L。通常已知的是,这种浓缩的制剂在使用时,根据农业实践,可以稀释1至2000倍。
水相含有水作为溶剂介质和任选的水溶性或水可分散性活性成分。通常,乳液制剂水相中的水用于平衡最终组合物。水相中的成分与油相中的一种或多种成分的相互作用或反应包括但不限于:由于油相中的水分散性成分的奥斯瓦尔德熟化引起的晶体形成和生长,或者由油相中存在的成分引起的水相中成分的降解。
在油相中具有足够高溶解性(约>60ppm)、熔点足够高以至在环境条件下为固体的水可分散性或水溶性活性物可能导致油相中因奥斯瓦尔德熟化引起的晶体形成和生长。与水相不同,油相可以包括油性溶剂、油性活性物和/或油溶性活性物或辅料的任何组合,其中水性成分的溶解性可以依据具体情况有较大不同。例如,吡氟草胺具有在甲基化的种子油(methylatedseed oils)中>10000ppm的溶解性,艾克敌105或多杀霉素具有在石油基油中>10000ppm的溶解性,双苯三唑醇(bitertanol)具有在石蜡基油或芳香族油中>1000ppm的溶解性,五氟磺草胺具有在刈草胺(acetochlor)中>1000ppm的溶解性,等等。对于给定的常常设计用来满足具体市场、客户或应用目的的油相而言,水相中的活性物或其他成分会由于溶解性高和奥斯瓦尔德熟化而在油相中形成并长出大晶体,并导致乳液失去稳定性。
油相或水相中成分由于其相对的水相或油相中成分的存在所引起的降解也可能取决于具体的组合物视情况而不同。例如当水相中存在艾克敌105或多杀霉素时,油相中的甲基毒死蜱会降解。当水相中存在艾克敌105或多杀霉素时,油相中的γ-氯氟氰菊酯(γ-Cyhalothrin)会降解。油相或水相中的双氟磺草胺会在相对相中存在胺或碱性官能团时发生降解。当水相中存在三唑化合物或碱性化学品时,油相中的敌螨普或二硝巴豆酸酯(meptyl-dinocap)会降解。
第一聚合物表面活性剂由具有聚氧化乙烯(PEG)亲水部分和12-羟基硬脂酸疏水部分的ABA嵌段共聚物构成。这种聚合物表面活性剂的优选实例为市售的表面活性剂AtloxTM 4912(Uniqema的商标),分子量为5000。这种聚合物表面活性剂的另一个实例为市售表面活性剂TermulTM 2510(Huntsman的商标)。第一聚合物表面活性剂的量为1g/L至200g/L,优选为10g/L至100g/L。
第二聚合物表面活性剂由聚亚烷基二醇醚构成。这种聚合物表面活性剂的优选实例为市售表面活性剂AtlasTM G-5000(EO-PO嵌段共聚物;Uniqema的商标)。这种聚合物表面活性剂的另一个实例为市售表面活性TermulTM 5429(醇的烷氧基化物(alcohol alkoxylate);Huntsman的商标)。第二聚合物表面活性剂的量为1g/L至200g/L,优选为10g/L至100g/L。
在制备本发明水包油乳液的典型方法中,通过混合水与水溶性或水可分散性成分来制备水相,水溶性或水可分散性成分包括但不限于:活性物(actives)、表面活性剂(聚亚烷基二醇醚,如Atlas G-5000)和任选其他惰性成分如增稠剂、pH缓冲剂、分散剂、湿润剂、杀生物剂(biocide)等。在水不溶性固体活性物(如吡氟草胺、五氟磺草胺)的情况下,可以将固体材料研磨至所需的尺寸范围(如0.1-10μm)并优选借助湿润剂或分散剂来预分散在浓缩的水分散体中。有许多市售可得的研磨或分散工艺和设备可用于该目的,本领域技术人员对此是熟知的。油相通过将具有聚氧化乙烯(PEG)亲水部分和12-羟基硬脂酸疏水部分(如Atlox 4912)的油溶性ABA嵌段共聚物与油混溶性或油溶性成分混合而制备,油混溶性或油溶性成分包括但不限于:油性溶剂、油性活性物、油溶性活性物、油性辅料、油性安全剂等。最终的乳液制剂如下制备:在高剪切力均化下将油相缓慢加入水相直到获得所需乳液液滴尺寸(0.1-10μm)。
化学不稳定性为油溶性杀虫性酯通过与水相的相互作用而发生水解的乳液的实例包含:
a)不连续油相,其含有1g/L至700g/L的三氯吡氧乙酸丁氧乙酯;
b)连续水相,其含有100g/L至990g/L的水和1g/L至300g/L的氯氨吡啶酸的盐;
c)1g/L至200g/L的第一聚合物表面活性剂和1g/L至200g/L的第二表面活性剂,所述第一聚合物表面活性剂包含具有聚氧化乙烯(PEG)亲水部分和12-羟基硬脂酸疏水部分的ABA嵌段共聚物,所述第二聚合物表面活性剂包含聚亚烷基二醇醚;以及
d)任选地,其他惰性制剂成分。
物理不稳定性为由于奥斯瓦尔德熟化引起的晶体生长的乳液的实例包含:
a)不连续油相,其含有1g/L至700g/L的豆油脂肪酸甲酯(methylsoyate);
b)连续水相,其含有包含1g/L至500g/L的五氟磺草胺、1g/L至500g/L的吡氟草胺和200g/L至990g/L水的分散体;
c)1g/L至200g/L的第一聚合物表面活性剂和1g/L至200g/L的第二表面活性剂,所述第一聚合物表面活性剂包含具有聚氧化乙烯(PEG)亲水部分和12-羟基硬脂酸疏水部分的ABA嵌段共聚物,所述第二聚合物表面活性剂包含聚亚烷基二醇醚;以及
d)任选地,其他惰性制剂成分。
除了上述组合物及其用途之外,本发明还包括这些乳液与一种或多种附加相容性成分组合的组合物或用途。其他附加成分可能包括,例如:一种或多种杀虫剂、染料和任何其他提供功能实用性的附加成分,例如稳定剂、香料、粘度调节剂、悬浮助剂和防冻剂(freeze-point depressant)。
具体实施方式
下列实施例解释了本发明。
实施例1:在54℃储存的三氯吡氧乙酸丁氧乙酯的水解
制剂A为对比制剂,其含有30.7wt%三氯吡氧乙酸丁氧乙酯、3.3wt%氯氨吡啶酸钾盐、9.65wt%Synperonic A2(C12-C15脂肪醇乙氧基化物3EO)、6.4wt%Tensiofix 96DB08(非离子型EO-PO嵌段共聚物)以及构成成分的余量(balance of the ingredient)的水和Dowanol DPM;制剂B为本发明的制剂,其含有29.4wt%三氯吡氧乙酸丁氧乙酯、3.1wt%氯氨吡啶酸钾盐、2.9wt%Atlox 4912(聚羟基硬脂酸与聚乙二醇共聚的ABA嵌段共聚物)、2.9wt%Atlas G-5000(EO-PO嵌段共聚物)、4.4wt%丙二醇和水,以及少量成分如甲基纤维素(增稠剂)、黄胞胶(增稠剂)、消泡剂、proxel GXL(杀生物剂)、磷酸二氢钾和磷酸氢二钾(pH缓冲剂)构成成分的余量,将制剂A和制剂B在54℃储存并且监控三氯吡氧乙酸丁氧乙酯的水解。图1比较了54℃时两种制剂中三氯吡氧乙酸丁氧乙酯水解为三氯吡氧乙酸的情况。三氯吡氧乙酸在制剂A中的生成比在制剂B中快3倍(The generation of triclopyr acid was3-fold slower in Formulation B than that in Formulation A),这表明聚合物表面活性剂、Atlox 4912和Atlas G-5000的组合形成了更致密更紧凑或更坚固的界面,阻止了三氯吡氧乙酸丁氧乙酯和水之间的相互作用和水解反应。因此,制剂B在环境温度下保持稳定超过24个月,在54℃时保持稳定超过6个月,而制剂A在环境温度下约8个月后或在54℃2个月后会形成三氯吡氧乙酸的晶体和氯氨吡啶酸的晶体。
实施例2:存在豆油脂肪酸甲酯时吡氟草胺的稳定性
制备七种水包油乳液,其含有如表1中列出的5wt%的吡氟草胺、0.75wt%的水性分散体中的五氟磺草胺、5wt%丙二醇、37.5wt%豆油脂肪酸甲酯(在油相中作为五氟磺草胺辅料)和表面活性剂,并测试在24小时的-10℃/40℃循环下储存后的冷冻-融化(freeze-thaw stability)稳定性。由于吡氟草胺在豆油脂肪酸甲酯中的溶解性较高(>1wt%),吡氟草胺严重倾向于进行奥斯瓦尔德熟化,引起结晶和晶体生长,这最终使制剂失去稳定性。稳定性结果总结于表1中。显示在储存条件下样品5的稳定性显著好于其他6种样品,这表明聚合物表面活性剂、Atlox 4912和Atlas G-5000的组合形成了更致密更紧凑更坚固的界面,阻止吡氟草胺跨过界面的输送和扩散,并限制会导致结晶和晶体生长的奥斯瓦尔德熟化。因此,样品5在加速储存条件下保持稳定超过6周,而其他6种制剂在两周内就失去稳定性并发生晶体生长。
表1:存在豆油脂肪酸甲酯时吡氟草胺的稳定性
所有样品含有:37.5%的豆油脂肪酸甲酯、5%的丙二醇、5%的吡氟草胺(DFF)、075%的五氟磺草胺、余量的水和其他常规惰性成分。
*FT指冷冻-融化,-10℃和40℃之间的24小时循环
Claims (5)
1.稳定的水包油乳液,其含有:
a)分散油相,包含油性活性成分、油溶性活性成分、油性辅料或油性溶剂,这些成分能与连续水相中的各成分反应或相互作用,从而引起化学或物理上的不稳定性;
b)连续水相,其包含水和水溶性或水分散性成分;
c)量为1g/L至200g/L的第一聚合物表面活性剂和量为1g/L至200g/L的第二聚合物表面活性剂,所述第一聚合物表面活性剂包含具有聚氧化乙烯(PEG)亲水部分和12-羟基硬脂酸疏水部分的ABA嵌段共聚物,所述第二聚合物表面活性剂包含聚亚烷基二醇醚;以及
d)任选地,其他惰性制剂成分。
2.权利要求1的乳液,其中所述化学不稳定性为油溶性酯除草剂通过与水相相互作用而发生水解。
3.权利要求2的乳液,其含有:
a)不连续油相,其含有1g/L至700g/L的三氯吡氧乙酸丁氧乙酯;
b)连续水相,其含有100g/L至990g/L的水和1g/L至300g/L的氯氨吡啶酸的盐;
c)1g/L至200g/L的第一聚合物表面活性剂和1g/L至200g/L的第二表面活性剂,所述第一聚合物表面活性剂包含具有聚氧化乙烯(PEG)亲水部分和12-羟基硬脂酸疏水部分的ABA嵌段共聚物,所述第二聚合物表面活性剂包含聚亚烷基二醇醚;以及
d)任选地,其他惰性制剂成分。
4.权利要求1的乳液,其中所述物理不稳定性为由于奥斯瓦尔德熟化引起的晶体生长。
5.权利要求4的乳液,其含有:
a)不连续油相,其含有1g/L至700g/L的豆油脂肪酸甲酯;
b)连续水相,其含有包含1g/L至500g/L的五氟磺草胺、1g/L至500g/L的吡氟草胺和200g/L至990g/L水的分散体;
c)1g/L至200g/L的第一聚合物表面活性剂和1g/L至200g/L的第二表面活性剂,所述第一聚合物表面活性剂包含具有聚氧化乙烯(PEG)亲水部分和12-羟基硬脂酸疏水部分的ABA嵌段共聚物,所述第二聚合物表面活性剂包含聚亚烷基二醇醚;以及
d)任选地,其他惰性制剂成分。
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CN104519743A (zh) * | 2012-06-06 | 2015-04-15 | 美国陶氏益农公司 | 高浓度农药悬浮剂 |
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UA109416C2 (xx) * | 2009-10-06 | 2015-08-25 | Стабільні емульсії типу "масло в воді" | |
BR112013006341A2 (pt) * | 2010-09-17 | 2016-06-21 | Dow Agrosciences Llc | formulações agrícolas líquidas com estabilidade aperfeiçoada |
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UY39627A (es) | 2011-10-26 | 2022-03-31 | Monsanto Technology Llc | Sales de herbicidas de ácido carboxílico |
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US9717246B1 (en) | 2016-05-24 | 2017-08-01 | Kop-Coat, Inc. | Method and related solution for protecting wood through enhanced penetration of wood preservatives employing buffered amine oxides and alkoxylated oils |
EP3572439A4 (en) * | 2017-01-23 | 2020-10-28 | Techno-Umg Co., Ltd. | RUBBER POLYMER, GRAFT COPOLYMER, THERMOPLASTIC RESIN COMPOSITION |
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- 2008-08-11 CN CN201610957938.1A patent/CN107006493B/zh active Active
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Cited By (8)
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CN103501602A (zh) * | 2011-06-10 | 2014-01-08 | 胡茨曼澳大利亚股份有限公司 | 用于农业油基于配制剂的结构化剂和乳化剂 |
CN103501602B (zh) * | 2011-06-10 | 2016-08-17 | 胡茨曼澳大利亚股份有限公司 | 用于农业油基于配制剂的结构化剂和乳化剂 |
CN104519743A (zh) * | 2012-06-06 | 2015-04-15 | 美国陶氏益农公司 | 高浓度农药悬浮剂 |
TWI586273B (zh) * | 2012-06-06 | 2017-06-11 | 陶氏農業科學公司 | 高強度除草劑懸浮濃縮液 |
CN104519743B (zh) * | 2012-06-06 | 2020-07-17 | 美国陶氏益农公司 | 高浓度农药悬浮剂 |
CN111316982A (zh) * | 2013-11-08 | 2020-06-23 | 美国陶氏益农公司 | 包含天然或石油衍生的油的农药乳液浓缩物及使用方法 |
CN107660122A (zh) * | 2015-05-12 | 2018-02-02 | 禾大公司 | 农业化学乳液 |
CN114190388A (zh) * | 2021-12-29 | 2022-03-18 | 浙江龙游东方阿纳萨克作物科技有限公司 | 一种以吡氟酰草胺与五氟磺草胺复配为活性成分的除草剂及其应用 |
Also Published As
Publication number | Publication date |
---|---|
JP5444225B2 (ja) | 2014-03-19 |
CN107006493B (zh) | 2020-09-22 |
WO2009032481A2 (en) | 2009-03-12 |
ATE500729T1 (de) | 2011-03-15 |
MY158318A (en) | 2016-09-30 |
EP2340710A3 (en) | 2011-09-07 |
MX2010002340A (es) | 2010-05-14 |
CA2694662A1 (en) | 2009-03-12 |
EP2340710A2 (en) | 2011-07-06 |
ES2358234T5 (es) | 2019-12-23 |
ES2358234T3 (es) | 2011-05-06 |
EP2180784B2 (en) | 2019-05-29 |
US20090062127A1 (en) | 2009-03-05 |
EP2180784A2 (en) | 2010-05-05 |
EP2340710B1 (en) | 2013-03-20 |
JP2010537992A (ja) | 2010-12-09 |
CA2694662C (en) | 2014-04-29 |
ES2413283T3 (es) | 2013-07-16 |
DE602008005464D1 (de) | 2011-04-21 |
AU2008296737A1 (en) | 2009-03-12 |
EP2180784B1 (en) | 2011-03-09 |
WO2009032481A3 (en) | 2010-05-27 |
CO6260006A2 (es) | 2011-03-22 |
BRPI0815828A2 (pt) | 2014-10-07 |
US20160192641A1 (en) | 2016-07-07 |
AU2008296737B2 (en) | 2014-01-09 |
CN107006493A (zh) | 2017-08-04 |
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