CN113817100A - 一种***醇分子印迹聚合物微球的制备方法 - Google Patents
一种***醇分子印迹聚合物微球的制备方法 Download PDFInfo
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Abstract
本发明提供了一种***醇分子印迹聚合物微球的制备方法，该方法是将***醇与功能单体溶于溶剂中，超声混合均匀后，在无氧条件下进行预聚合；预聚合完成后，向其中添加交联剂和引发剂进行加热诱导聚合；本发明采用沉淀聚合的聚合方式，得到分子印迹聚合物；分子印迹聚合物经过碾磨、洗脱、干燥后得到***醇分子印迹聚合物微球；本发明制备的***醇分子印迹聚合物微球分布均匀，对目标物质***醇的吸附效果良好。
Description
技术领域
本发明属于分子印迹聚合物领域，具体涉及到一种***醇分子印迹聚合物微球的制备工艺。
背景技术
***醇，别名羟锈宁、三泰隆、1-（4-氯苯氧基）-3,3-二甲基-1-(1H-1,2,4***-l-基)-2-丁醇；是一种内吸型***类杀菌剂，近年来在水稻、玉米、小麦农作物的黑穗病、斑病、锈病的防治中广泛应用；***醇具有三氮杂环结构，物化性质比较稳定，在自然环境中不易自动降解，会长期存在于环境中，会对人类和动物的生命安全造成不良影响。
分子印迹技术作为一种特殊的抗原抗体人工合成技术，能够对目标物质进行选择性识别，达到富集、净化的目的。相对于生物识别，分子印迹技术可以根据实际需求选择制备的原料和制备条件，制备出耐用且符合实际需求的分子印迹材料，用于对目标物质的吸附。目前对于***醇分子印迹聚合物多采用本体聚合的方法，分子印迹聚合物的外貌多呈现不规则形状，印迹空腔存在较少。
发明内容
针对现有技术存在的问题，本发明提供了一种***醇分子印迹聚合物微球的制备方法，本发明方法制得的分子印迹聚合物微球粒径分布均匀，吸附效果也较好。
本发明***醇分子印迹聚合物微球的制备方法如下：
（1）将模板分子***醇和功能单体置于溶剂中，超声混和均匀后，混合物中通N2 10~20min，然后置于15~45℃恒温气浴振荡器中进行预聚合5~12h，即得到预聚合溶液；
所述溶剂为甲醇、乙腈、甲苯、二氯甲烷或氯仿；功能单体为α-甲基丙烯酸、丙烯酸、三氟甲基丙烯酸或丙烯酰胺；其中功能单体与***醇的摩尔比为1~8:1；
（2）向步骤（1）得到的预聚合溶液中加入交联剂和引发剂，通N2 10~20min后，置于35~65℃的恒温气浴振荡器中热聚合12~24h，离心，固体干燥后得到聚合物；
所述交联剂为环氧氯丙烷、乙二醇二甲基丙烯酸酯或二乙烯基苯；引发剂为过氧化苯甲酰、偶氮二异丁腈或偶氮二甲基异戊腈；交联剂和引发剂的摩尔比为5~30:1，引发剂与***醇的摩尔比为1~5:1；干燥温度为30~45℃；
（3）将步骤（2）得到的聚合物进行碾磨、洗脱、干燥后得到***醇分子印迹聚合物微球。
所述洗脱溶剂为甲醇和乙酸按体积比7~9:1的比例混合制得的混合溶剂，干燥温度在30~45℃。
本发明采用热引发沉淀聚合法经过预聚合、热聚合过程得到***醇分子印迹聚合物微球。本发明制备的分子印迹聚合物微球粒径分布比较均匀且形貌明显可观，聚合物平均粒径在78~116nm。本发明制备简捷、成本低且效果稳定。
附图说明
图1为***醇分子印迹聚合物扫描电镜图；
图2为***醇分子印迹聚合物的红外光谱图；
图3为空白分子印迹聚合物的红外光谱图；
图4为测定MIPs材料吸附后上清液***醇含量的液质色谱图。
具体实施方式
为了使本发明的优点和目的更加清晰，结合实际实施例对本发明作更进一步解释阐述。针对本发明的保护范围，并不限定于以下所述实施例。
实施例1：
（1）按***醇与α-甲基丙烯酸摩尔比为1:2的比例，将***醇和α-甲基丙烯酸溶于甲醇中，超声混匀后，混合物中通N2 15min，然后混合物置于30℃恒温气浴振荡器中进行预聚合反应12h，得到预聚合溶液；
（2）按交联剂和引发剂的摩尔比为8:1的比例，向步骤（1）得到的预聚合溶液中添加交联剂乙二醇二甲基丙烯酸酯和引发剂偶氮二甲基异戊腈，通N2 15min后，置于55℃的恒温气浴振荡器中热聚合24h，离心，固体35℃干燥后得到聚合物；其中偶氮二甲基异戊腈与***醇的摩尔比为1:1；同时设置空白对照，即不添加***醇，其它制备条件与上；
（3）将步骤（2）得到的聚合物进行碾磨，用甲醇-乙酸混合液洗脱***醇，40℃干燥后得到***醇分子印迹聚合物微球（MIPs）和空白分子印迹聚合物（NIPs）；其中甲醇-乙酸混合液甲醇和乙酸按体积比7:1的比例混合制得，MIPs的形貌如图1所示，从图中可以看出本实施例制得的聚合物呈球形，分布比较均匀；MIPs和NIPs的红外光谱图如图2、图3所示，从图中看出在666.7nm附近明显出峰不同，说明有***醇聚合在聚合物上。
将制备的MIPs、NIPs分别称取30mg置于20mL玻璃瓶中，加入6mL 10mg/L的***醇溶液，在25℃下进行吸附试验，吸附完成后取玻璃瓶中的上清液，滤膜过滤后，采用液相色谱-串联质谱进行检测，MIPs材料吸附后上清液的色谱图如图4所示，计算其吸附效果的数据如表1所示，由表1可知MIPs的印迹因子为2.21；
表1：MIPs、NIPs的吸附效果
实施例2
（1）按***醇与α-甲基丙烯酸摩尔比为1:4的比例，将***醇和功能单体α-甲基丙烯酸溶于乙腈中，超声混匀后，混合物中通N2 19min，置于25℃恒温气浴振荡器中进行预聚合10h，得到预聚合溶液；
（2）按交联剂和引发剂的摩尔比为20:1的比例，向步骤（1）得到的预聚合溶液中添加交联剂乙二醇二甲基丙烯酸酯和引发剂偶氮二异丁腈，通N2 10min后，置于60℃的恒温气浴振荡器中热聚合15h，离心，固体40℃干燥后得到聚合物；其中偶氮二异丁腈与***醇的摩尔比为2:1；同时设置空白对照，即不添加***醇，其它制备条件与上；
（3）将步骤（2）得到的聚合物进行碾磨，用甲醇-乙酸混合液洗脱***醇，35℃干燥后得到***醇分子印迹聚合物微球（MIPs）和空白分子印迹聚合物（NIPs）；其中甲醇-乙酸混合液甲醇和乙酸按体积比9:1的比例混合制得；
将制备的MIPs、NIPs称取30mg置于20mL玻璃瓶中，加入6mL 12mg/L的***醇溶液，在25℃下进行吸附试验，吸附完成后取玻璃瓶中的上清液，滤膜过滤后，采用液相色谱-串联质谱进行检测，计算其吸附效果的数据如表2所示，由表2可知MIPs的印迹因子为2.51；
表2：MIPs、NIPs的吸附效果
实施例3
（1）按***醇与三氟甲基丙烯酸摩尔比为1:2的比例，将***醇和三氟甲基丙烯酸溶于乙腈中，超声混匀后，混合物中通N2 20min，然后置于22℃恒温气浴振荡器中进行预聚合9h，得到预聚合溶液；
（2）按交联剂和引发剂的摩尔比为30:1的比例，向步骤（1）得到的预聚合溶液中添加交联剂二乙烯基苯和引发剂偶氮二异丁腈，通N2 20min后，置于40℃的恒温气浴振荡器中热聚合24h，离心，固体45℃干燥后得到聚合物；其中偶氮二异丁腈与***醇的摩尔比为4:1；同时设置空白对照，即不添加***醇，其它制备条件与上；
（3）将步骤（2）得到的聚合物进行碾磨，用甲醇-乙酸混合液洗脱***醇，45℃干燥后得到***醇分子印迹聚合物微球（MIPs）和空白分子印迹聚合物（NIPs）；其中甲醇-乙酸混合液甲醇和乙酸按体积比8:1的比例混合制得；
将制备的MIPs、NIPs称取30mg置于20mL玻璃瓶中，加入6mL 15mg/L的***醇溶液，在25℃下进行吸附试验，吸附完成后取玻璃瓶中的上清液，进行滤膜过滤后，采用液相色谱-串联质谱进行检测，计算其吸附效果的数据如表3所示，由表3可知MIPs的印迹因子为2.35；
表3：MIPs、NIPs的吸附效果
实施例4：
（1）按***醇与丙烯酸摩尔比为1:6的比例，将***醇和丙烯酸溶于氯仿中，超声混匀后，混合物中通N2 18min，然后置于30℃恒温气浴振荡器中进行预聚合11h，得到预聚合溶液；
（2）按交联剂和引发剂的摩尔比为15:1的比例，向步骤（1）得到的预聚合溶液中添加交联剂环氧氯丙烷和引发剂偶氮二异丁腈，通N2 18min后，置于50℃的恒温气浴振荡器中热聚合20h，离心，固体35℃干燥后得到聚合物；其中偶氮二异丁腈与***醇的摩尔比为3:1；同时设置空白对照，即不添加***醇，其它制备条件与上；
（3）将步骤（2）得到的聚合物进行碾磨，用甲醇-乙酸混合液洗脱***醇，35℃干燥后得到***醇分子印迹聚合物微球（MIPs）和空白分子印迹聚合物（NIPs）；其中甲醇-乙酸混合液甲醇和乙酸按体积比9:1的比例混合制得；
将制备的MIPs、NIPs称取30mg置于20mL玻璃瓶中，加入6mL 25mg/L的***醇溶液，在25℃下进行吸附试验，吸附完成后取玻璃瓶中的上清液，进行滤膜过滤后，采用液相色谱-串联质谱进行检测，计算其吸附效果的数据如表4所示，由表4可知MIPs的印迹因子为2.34；
表4：MIPs、NIPs的吸附效果
Claims (8)
1.一种***醇分子印迹聚合物微球的制备方法，其特征在于，步骤如下：
（1）将***醇和功能单体置于溶剂中，超声混匀后，通N2 10~20min，然后置于恒温气浴振荡器中进行预聚合，得到预聚合溶液；
（2）向步骤（1）预聚合溶液中加入交联剂和引发剂，通N2 10~20min后，置于35~65℃的恒温气浴振荡器中热聚合12~24h，离心，固体干燥后得到聚合物；
（3）将步骤（2）得到的聚合物进行碾磨、洗脱、干燥后得到***醇分子印迹聚合物微球。
2.根据权利要求1所述的***醇分子印迹聚合物微球的制备方法，其特征在于：步骤（1）中溶剂为甲醇、乙腈、二氯甲烷、甲苯或氯仿。
3.根据权利要求1所述的***醇分子印迹聚合物微球的制备方法，其特征在于：步骤（1）中预聚合温度为15~45℃，预聚合时间为5~12h。
4.根据权利要求1所述的***醇分子印迹聚合物微球的制备方法，其特征在于：步骤（1）中功能单体为α-甲基丙烯酸、丙烯酸、三氟甲基丙烯酸或丙烯酰胺；其中功能单体与***醇的摩尔比为1~8:1。
5.根据权利要求1所述的***醇分子印迹聚合物微球的制备方法，其特征在于：步骤（2）中交联剂为环氧氯丙烷、乙二醇二甲基丙烯酸酯或二乙烯基苯。
6.根据权利要求5所述的***醇分子印迹聚合物微球的制备方法，其特征在于：步骤（2）中引发剂为过氧化苯甲酰、偶氮二异丁腈或偶氮二甲基异戊腈；交联剂和引发剂的摩尔比为5~30:1，引发剂与***醇的摩尔比为1~5:1。
7.根据权利要求1所述的***醇分子印迹聚合物微球的制备方法，其特征在于：步骤（3）洗脱溶剂为甲醇和乙酸按体积比7~9:1的比例混合制得的混合溶剂。
8.根据权利要求1所述的***醇分子印迹聚合物微球的制备方法，其特征在于：步骤（2）、步骤（3）中干燥温度为30~45℃。
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| US20100227761A1 (en) * | 2006-01-12 | 2010-09-09 | Basf Se | Agrochemical Formulations Based on Molecularly Imprinted Acrylates |
| CN108084341A (zh) * | 2017-11-03 | 2018-05-29 | 仲恺农业工程学院 | 结晶紫分子印迹微球的合成方法及应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US20100227761A1 (en) * | 2006-01-12 | 2010-09-09 | Basf Se | Agrochemical Formulations Based on Molecularly Imprinted Acrylates |
| CN108084341A (zh) * | 2017-11-03 | 2018-05-29 | 仲恺农业工程学院 | 结晶紫分子印迹微球的合成方法及应用 |
Non-Patent Citations (4)
| Title |
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| 刘丽梅等: "***醇分子印迹整体柱用于结构类似物的分离与分析", 《农药》 * |
| 彭畅等: "识别***类农药的片段印迹聚合物的合成及在固相萃取中的应用", 《高等学校化学学报》 * |
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