CN106492706A - 一种梳型高分子分散剂及其制备方法与应用 - Google Patents
一种梳型高分子分散剂及其制备方法与应用 Download PDFInfo
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- CN106492706A CN106492706A CN201610799419.7A CN201610799419A CN106492706A CN 106492706 A CN106492706 A CN 106492706A CN 201610799419 A CN201610799419 A CN 201610799419A CN 106492706 A CN106492706 A CN 106492706A
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- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims abstract description 8
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/14—Derivatives of phosphoric acid
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
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- A—HUMAN NECESSITIES
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- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
- A01N31/14—Ethers
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
- A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
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- A—HUMAN NECESSITIES
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
-
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Abstract
本发明公开了一种“梳型”高分子分散剂及其制备方法与应用。高分子分散剂结构式为:
Description
技术领域
本发明公开了可控聚合“梳型”高分子分散剂的制备方法以及在农药展膜油剂中的应用。
背景技术
传统的自由基共聚技术为快引发、快增长、高转移、快终止,无法获取指定结构的高分子化合物,产品分子量分布宽,对原料和催化剂选择性宽。活性离子聚合技术快引发、慢增长、慢转移、无终止,可有效获取指定结构的高分子化合物,产品分子量分布窄对原料和反应条件苛刻。可逆加成-断裂链转移活性自由基聚合技术(RAFT技术)通过对链转移剂(双硫酯或三硫代碳酸酯)的可逆加成断裂平衡机理来调控体系活性自由基的浓度,以达到控制聚合的目的,具有分子结构的可设计性、产品分子量分布窄、反应条件相对温和。采用RAFT聚合制备嵌段型和梳形结构的高分子表面活性剂在水性和溶剂型颜料分散领域已经引起人们的关注。张连兵等用RAFT聚合制备了苯乙烯与马来酸酐的共聚物,作为高分子分散剂,相对于常规的小分子表面活性,在水性有机颜料的分散上有无法比拟的优势(张连兵,房宽峻,付少海等.可聚合型高分子分散剂的合成及应用[J].印染,2010,11,1-4.)。刘长春以二硫代苯甲酸苄酯为链转移剂,偶氮二异丁腈AIBN为引发剂,控制苯乙烯和丙烯酸的共聚得到双亲性嵌段共聚物,作为超分散剂对二氧化硅粉体具有优良的分散性能(刘长春.RAFT法合成超分散剂PS-b-PAA及其分散性能研究[J].浙江化工,2005,36(12):15-18.)。CN102308798A公开了RAFT可控聚合嵌段高分子表面活性剂的制备及其在农药水分散粒剂和水悬浮剂中的应用。就目前而言,还未发现RAFT可控聚合梳型高分子分散剂在省力化剂型-展膜油剂中的应用。
国内外研究的农药展膜油剂作为省力化剂型的一种,大多以有机溶剂作载体溶解原药,有机溶剂的使用污染环境,同时伴随着溶剂的挥发,制剂中的活性组分会因难溶于水而造成农药结晶聚集,形成固体微粒并析出,从而很难保持其在水中的有效浓度均匀度。展膜油剂急需解决的问题之一为溶剂的选择,冯超等人已经报道过采用环保型生物酯类有机溶剂在5%醚菊酯SO中的应用(冯超,杨代斌,袁会珠.5%醚菊酯展膜油剂配制及其对稻飞虱的防治效果[J].农药学学报2010,12(1):67-72);CN201310316135.4公开了绿色生物溶剂在吡蚜酮SO中的应用。文献中报道的SO制备工艺大都是采用溶剂将原药溶解得到透明溶液,加入至混合好的表面活性剂和扩展剂,搅拌得到展膜油剂。还未见文献报道采用湿法砂磨工艺制备油可分散体,再加入扩散剂的方法制备SO。
发明内容
本发明在前人工作的基础上,提供一种“梳型”高分子分散剂及其制备方法与应用,采用RAFT活性聚合技术,以十二烷硫基硫代羰基硫基丙酸为链转移剂,偶氮二异丁腈为引发剂,不饱和单体之间的接枝共聚获得“梳型”高分子分散剂,将其应用于展膜油剂体系,以油酸甲酯等环保型溶剂为有机载体,通过湿法砂磨工艺得到油可分散体系,并加入扩散剂得到不同常规工艺的展膜油剂。
本发明的第一个目的是通过以下技术方案实现的,梳型高分子分散剂结构式为:
其中,R1为RAFT试剂R基团、C2-C20直链或支链烷基、C3-C20支链或直链脂肪酸;R2为任选的H、C4-C20直链、C4-C20支链长碳链、C4-C20长链聚醚链中的任意一种或任意两种或两种以上的混合;R3为苯基、-COOH、丙烯酰胺残基中的任意一种或任意两种或两种以上的混合物;R4为氢或甲基。m和n为0-100的整数,m、n不同时为0。
所述的“梳型”高分子分散剂的相对分子量为6000~60000,优选8000~40000。
本发明的第二个目的是通过以下技术方案实现的,RAFT可控聚合梳型高分子分散剂的合成方法如下所述:
向带有搅拌器、恒压滴液槽、温度计和冷凝器的四口烧瓶内加入一定量的亲水单体1、RAFT试剂和溶剂,搅拌加热使物料溶解,当达到40~120℃时,分别滴加一定量的不饱和疏水单体2和引发剂的溶液,控制滴加时间与反应时间,反应完毕用油酸甲酯置换溶剂,得到溶于油酸甲酯的聚羧酸盐分散剂。
所示亲水单体1为马来酸酐月桂醇聚氧乙烯醚单酯、(甲基)烯丙基聚氧乙烯醚、异戊烯醇聚氧乙烯醚、丙烯酸、马来酸酐、丙烯酰胺、N,N-二甲基丙烯酰胺、N-异丙基丙烯酰胺NIPAM或N-丙烯酰基吗啉等中的任意一种或任意两种或两种以上的组合物。
所述不饱和疏水单体2包括:苯乙烯、丙烯酸异辛酯、丙烯酸丁酯、丙烯酸十二酯、甲基丙烯酸甲酯以及烯丙基聚氧丙烯醚等中的任意一种或任意两种或两种以上的组合物。
所述RAFT试剂优选十二烷硫基硫代羰基硫基丙酸。
所述的引发剂为热分解型过氧化物引发剂,优选K2S2O8、H2O2、(NH4)2S2O8、BPO、TBPB(过氧化苯甲酰叔丁酯)或MEKP(过氧化甲乙酮);或为偶氮化合物引发剂如AIBN、ABVN或ACC;或为氧化还原分解型引发剂如过硫酸铵/亚硫酸氢钠体系等。
聚合反应采用溶液聚合的方法,溶剂质量占聚合反应体系总质量的10~70%,溶剂可以为水、丙酮、乙酸乙酯、丁酮、甲苯、DMF、异丙醇等。聚合温度为40~120℃,优选50~90℃,滴加时间在30min~2h,反应时间为4~8h。所述亲油性单体与亲水性单体的摩尔比为0.1~10:1,优选0.2~5:1。所述RAFT试剂的用量为总有效物不饱和疏水单体与亲水单体摩尔量的0~5%,优选0.1%~2%;所述RAFT试剂用量与引发剂的摩尔比为0.1~20:1,优选1~10:1。
本发明的第三个目的是通过以下技术方案实现的,梳型高分子分散剂用于以植物油、油酸甲酯环保型溶剂为载体的农药展膜油剂SO中。
与现有技术相比,本发明具有以下有益效果:
“梳型”高分子分散剂结构中包含聚氧乙烯醚链、苯环和羧酸基团等基团重复单元,在湿法砂磨过程中,苯环与农药杂环结构类似,同一分子中多个苯环与农药粒子色散力作用,以及大分子链节侧链Lewis酸与含氮杂环的氢键作用,实现多点吸附,侧链聚氧乙烯醚和RAFT试剂末端长链与油相具有良好的相容性,在砂磨过程中犹如包在微粒表面一层可摆动的膜,提高颗粒间润滑作用,大分子主链空间位阻减少了颗粒间碰撞机率,提高了砂磨效率。
将本发明公开的可控梳型高分子分散剂首次应用于农药展膜油剂应用中,采用湿法砂磨新工艺制备展膜油剂,分散剂的梳型结构在砂磨过程中犹如包在微粒表面一层可摆动的膜,提高颗粒间润滑作用,大分子主链空间位阻减少了颗粒间碰撞机率,提高了砂磨效率。同传统SO的制备工艺相比,本发明减少了有毒溶剂的大量使用,分散剂与扩散剂协同作用,降低扩散剂的使用量,所得SO能够在水面上迅速分散,长时间保持药膜不破裂,无沉淀。此外,本发明公开的湿法砂磨SO的制备方法可在功能性(扩散性)油悬浮剂中有着非常广泛的应用前景。
具体实施方式
实施例1
单体摩尔比:烯丙基聚氧乙烯醚XPEG400/苯乙烯St/丙烯酸异辛酯EHA=1:2:1
RAFT试剂(十二烷硫基硫代羰基硫基丙酸)用量占总有效物摩尔比的0.5%
引发剂用量为总有效物摩尔比的0.1%
溶剂:异丙醇
向带有搅拌器、恒压滴液槽、温度计和冷凝器的四口烧瓶内加入XPEG1000、RAFT试剂和异丙醇,搅拌加热使物料溶解,当温度达到70℃,分别滴加苯乙烯和丙烯酸异辛酯的混合溶液和引发剂偶氮二异丁腈(AIBN)的异丙醇溶液,0.5-1h滴加完毕,保温4h。反应完毕用油酸甲酯置换溶剂,用乙醇胺中和pH至4-6。产品记为PC1,分子量为25000,分子量分布为1.28。
实施例2
单体摩尔比:异戊烯醇聚氧乙烯醚TPEG2400/苯乙烯/甲基丙烯酸十二酯=0.5:2:1
RAFT试剂(十二烷硫基硫代羰基硫基丙酸)用量占总有效物摩尔比的0.5%
引发剂用量为总有效物摩尔比的0.1%
溶剂:丙酮
工艺同实施例1。产品记为PC2,分子量为31000,分子量分布为1.36。
实施例3
单体摩尔比:马来酸酐脂肪醇聚醚单酯(马来酸酐与AEO-5以1:1摩尔酯化)/苯乙烯/丙烯酸丁酯=0.5:1:1
RAFT试剂(十二烷硫基硫代羰基硫基丙酸)用量占总有效物摩尔比的0.5%
引发剂BPO用量为总有效物摩尔比的0.1%
溶剂:丁酮
工艺同实施例1。产品记为PC3,分子量为28000,分子量分布为1.19。
实施例4
本发明高分子分散剂搭配扩散剂使用,湿法砂磨方法制备1%五氟磺草胺·5%氰氟草酯SO。
五氟磺草胺在溶剂中溶解性较差,采用加入分散剂湿法砂磨的方法,可以得到分散稳定性较好均匀制剂。用微量点滴器移取1.25ul制剂滴入水中,迅速扩散,分散剂与扩散剂协同作用,可增大扩散距离以及提高扩散速度。
实施例5
采用湿法砂磨制备2%嘧菌酯·2%噻呋酰胺SO。
实施例6
5%醚菊酯SO结果:
结论:本发明公开的可控梳型高分子分散剂应用在农药展膜油剂中,采用环保型植物油作为溶剂,制备的1%五氟磺草胺·5%氰氟草酯SO、2%嘧菌酯·2%噻呋酰胺SO以及5%醚菊酯SO都具有很好的存储稳定性,相对于不加分散剂或者国外相应分散而言,制剂在水中的扩散速度更快,扩散距离更远,搅动后薄膜不破裂,重新聚集成连续膜。
Claims (10)
1.一种梳型高分子分散剂,其特征在于,所述高分子分散剂结构式为:
式中:
R1为RAFT试剂R基团、C2-C20直链或支链烷基、C3-C20支链或直链脂肪酸;R2为H、C4-C20直链、C4-C20支链长碳链、C4-C20长链聚醚链中的任选一种或两种及以上的混合;R3为苯基、-COOH以及丙烯酰胺残基中的任选一种或两种及以上混合物;R4为氢或甲基;m和n为0-100的整数,m、n不同时为0。
2.根据权利要求1所述高分子分散剂,其特征是,所述高分子分散剂的相对分子量为6000-60000。
3.根据权利要求2所述“梳型”高分子分散剂,其特征是,所述高分子分散剂的相对分子量为8000-40000。
4.权利要求1-3所述高分子分散剂的制备方法,其特征在于,所述制备方法采用RAFT活性自由基技术制备得到,具体按照以下步骤进行:向带有搅拌器、恒压滴液槽、温度计和冷凝器的四口烧瓶内加入亲水单体、RAFT试剂和溶剂,搅拌加热使物料溶解,当达到40~120℃时,分别滴加不饱和疏水单体和引发剂的溶液,控制滴加时间与反应时间,反应完毕用油酸甲酯置换溶剂,得到溶于油酸甲酯的聚羧酸盐分散剂。
5.根据权利要求3所述高分子分散剂的制备方法,其特征是,所述亲水单体为马来酸酐月桂醇聚氧乙烯醚单酯、(甲基)烯丙基聚氧乙烯醚、异戊烯醇聚氧乙烯醚、丙烯酸、马来酸酐、丙烯酰胺、N,N-二甲基丙烯酰胺、N-异丙基丙烯酰胺NIPAM、N-丙烯酰基吗啉中的任意一种或任意两种或两种以上的组合物。
6.根据权利要求3所述高分子分散剂的制备方法,其特征是,所述不饱和疏水单体为苯乙烯、丙烯酸异辛酯、丙烯酸丁酯、丙烯酸十二酯、甲基丙烯酸甲酯以及烯丙基聚氧丙烯醚中的任意一种或任意两种或两种以上的组合物。
7.根据权利要求3所述高分子分散剂的制备方法,其特征是,所述的引发剂为热分解型过氧化物引发剂或偶氮化合物引发剂或氧化还原分解型引发剂,所述热分解型过氧化物引发剂为K2S2O8、H2O2、(NH4)2S2O8、BPO、TBPB(过氧化苯甲酰叔丁酯)或MEKP(过氧化甲乙酮);所述偶氮化合物引发剂为AIBN、ABVN或ACC;所述氧化还原分解型引发剂为过硫酸铵/亚硫酸氢钠体系。
8.根据权利要求3所述高分子分散剂的制备方法,其特征是,所述聚合反应溶剂质量占聚合反应体系总质量的10~70%,为水、丙酮、乙酸乙酯、丁酮、甲苯、DMF、异丙醇中的任意一种或任意两种或两种以上的混合物。
9.根据权利要求3所述高分子分散剂的制备方法,其特征是,所述不饱和疏水单体与亲水单体的摩尔比为0.1~10:1,所述RAFT试剂的用量为不饱和疏水单体与亲水单体总摩尔量的0~5%;所述RAFT试剂用量与引发剂的摩尔比为0.1~20:1;聚合温度为40~120℃,滴加时间30min~2h,反应时间为4~8h。
10.权利要求1-11所述的一种高分子分散剂的应用,其特征在于,所述高分子分散剂用于以植物油、油酸甲酯环保型溶剂为载体的农药展膜油剂SO中。
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